EP1788877A1 - Melanges synergiques fongicides composes de derives de triazolopyrmidine - Google Patents

Melanges synergiques fongicides composes de derives de triazolopyrmidine

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Publication number
EP1788877A1
EP1788877A1 EP05773888A EP05773888A EP1788877A1 EP 1788877 A1 EP1788877 A1 EP 1788877A1 EP 05773888 A EP05773888 A EP 05773888A EP 05773888 A EP05773888 A EP 05773888A EP 1788877 A1 EP1788877 A1 EP 1788877A1
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EP
European Patent Office
Prior art keywords
formula
compounds
methyl
alkyl
groups
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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EP05773888A
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German (de)
English (en)
Inventor
Carsten Blettner
Jochen Dietz
Wassilios Grammenos
Thomas Grote
Udo HÜNGER
Bernd Müller
Matthias NIEDENBRÜCK
Joachim Rheinheimer
Peter Schäfer
Frank Schieweck
Anja Schwögler
Barbara Nave
Maria Scherer
Siegfried Strathmann
Ulrich Schöfl
Reinhard Stierl
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BASF SE
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BASF SE
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Publication of EP1788877A1 publication Critical patent/EP1788877A1/fr
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to fungicidal mixtures containing as active Kompo ⁇ components
  • D together with the nitrogen atom forms a pyrrolidine, piperidine or azepin ring, which rings are unsubstituted or substituted by one or two methyl groups or by an ethyl, propyl or butyl group; and L is methyl, fluorine or chlorine;
  • Azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, flutriafol, hexaconazole, imazalil, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prochlorazone, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, Triadimol, triflumizole, triticonazole;
  • strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoximethyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin or 2- (ortho- (2,5-dimethylphenyloxymethylene) phenyl) -3-methoxy-acrylic acid methyl ester;
  • acylalanines such as benalaxyl, metalaxyl, mefenoxam, ofurace, oxadixyl;
  • dicarboximides such as iprodione, myclozoline, procymidone, vinclozolin;
  • G cinnamic acid amides and analogs such as dimethomorph, flumetover or fluorom;
  • antibiotics such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxine or streptomycin;
  • K) dithiocarbamates such as Ferbam, Nabam, Maneb, Mancozeb, Metam, Metiram, Propineb, Polycarbamate, Thiram, Ziram, Zineb;
  • heterocyclic compounds selected from anilazine, benomyl, boscalid,
  • Carbendazim Carboxin, Oxycarboxin, Cyazofamide, Dazomet, Dithianon, Famoxadone, Fenamidon, Fenarimol, Fuberidazole, Flutolanil, Furametpyr, Isoprothiolane, Mepronil, Nuarimol, Picobenzamide, Probenazole, Proquinazide, Pyrifenox, Pyroquilon, Quinoxyfen, Silthiofam, Thiabendazole, Thifluzamide, Thiophanate methyl, tiadinil, tricyclazole, triforine, 3- [5- (4-chlorophenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyridine, (2-chloro-5- [1- (3-methyl-benzyloyimino ethyl (ethyl) benzyl) carbamate, (methyl 2-chloro-5- [1- (6-methyl-pyridin-2-
  • Y is chlorine or bromine
  • R 31 is hydrogen, halogen, cyano, C 1 -C 4 -AIRyI, CrC 2 -HalogenalkyI,
  • R 311 is hydrogen, C r C 4 alkyl, CiC 4 -AlkyIcarbonyl;
  • R 32 is hydrogen, halogen, cyano, C r C 4 alkyl, CRCA haloalkyl,
  • Ar is phenyl or a five- or six-membered aromatic heterocycle containing one to four heteroatoms from the group O, N or S, where the rings are unsubstituted or may be substituted by one to three groups R 41 : R 41 is halogen, C 1 -C 4 -alkyl or C r C 4 haloalkyl;
  • R is phenyl, C r C 8 alkyl, C r C 8 haloalkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -HaIo- genalkoxy;
  • Q is hydrogen, C 1 -C 8 -alkyl, C r C 8 haloalkyl, C r C 8 alkoxy,
  • N) nitrophenyl derivatives such as binapacryl, dinocap, dinobutone, nitrophthalic isopropyl;
  • phenylpyrroles such as fenpiclonil or fludioxonil
  • P) sulfenic acid derivatives such as captafol, captan, dichlofluanid, folpet, tolylfluanide;
  • fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamide, chlorothalonil, cyflufenamid, cymoxanil, dazomet, diclomezine, diclock cymet, diclofluanid, diethofencarb, edifenphos, ethaboxam, fenhexamide, fentin acetate, fenoxanil, ferimzone, fluazinam, fosetyl, fosetyl-aluminum, phosphorous acid, iprovalicarb, hexachlorobenzene, mandipropamide, metrafenone, pencycuron, propamocarb, phthalide, tol-clofos- methyl , Quintozene, Zoxamide,
  • n 0, 1, 2 or 3
  • R is halogen, C 1 -C 4 -alkyl, Ci-C 4 haloalkyl, C 1 -C 4 -alkoxy, or halo- genalkoxy;
  • R 61 is hydrogen, C r C 8 alkyl, C 2 -C 8 alkenyl or C 2 -C 8 -alkynyl which are unsubstituted or may be substituted by one to three groups R a:
  • Phenyl which may be substituted by halogen, CrC ⁇ alkyl, C r C 8 haloalkyl, C 1 -C 8 -alkoxy, CRCS Halo ⁇ genalkoxy or C r C 8 alkylthio;
  • R 62 , R 63 may be the same or different and may be hydrogen, cyano,
  • R a is hydrogen, C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl or C 2 -C 8 -alkynyl, which are unsubstituted or may be substituted by one to three groups R b :
  • R b is one of the groups mentioned under R a , cyano, C (OO) R C , C (SS) R C or S (O) P R C ,
  • Ci-C may be substituted by halogen, Cn-Ca-alkyl, 8 haloalkyl, C 1 -C 8 -alkoxy, dC 8 -haloalkoxy or C r C 8 alkylthio; m is 0 or 1;
  • R 65 is one of the groups mentioned in R 64 ;
  • A is a direct bond, -O-, -S-, NR d , CHR e or -O-CHR e ;
  • R d , R e is one of the groups mentioned in R a ;
  • R 66 is phenyl or five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one to four heteroatoms from the group O, N or S, where the groups R 66 are unsubstituted or by one to three R f R f is one of the groups mentioned for R b or
  • variables have the following meaning: A 'O or N; GC or N; BN, or a direct bond;
  • R 72 is C 1 -C 4 -alkoxy; and
  • R 73 halogen;
  • growth retardants such as prohexadione and its salts, trinexapacethyl, chlormequat, mepiquat chloride and diflufenzopyr;
  • the invention relates to novel fungicidal triazolopyrimidines, a method for controlling harmful fungi with mixtures of a compound I with an active compound of groups A) to R) and the use of the compounds I with the active compounds of groups A) to R) for the preparation of such mixtures and Means containing these mixtures.
  • component 1 The compounds I referred to above as component 1, their preparation and their action against harmful fungi are generally proposed in the literature (US Pat. No. 5,593,996). Individual compounds of the formula I are known from US Pat. No. 5,593,996; WO 02/02563; WO 02/94020).
  • the present invention was based on new active substances or mixtures which show an improved action against harmful fungi with a reduced total amount of active substances applied.
  • compounds I are also preferred in which L is chlorine and D has one of the following meanings: -CH (CH 3 ) -CH (CH 3 ) -CH 2 -CH 2 -; -CH 2 -CH (CHs) -CH 2 -CH 2 -;
  • the new compounds can be obtained in various ways. They are advantageously prepared by reacting dichlorotriazolopyrimidines of the formula II 'in which L is methyl, fluorine or chlorine, with amines of the formula III' in which D is as defined for formula I under conditions generally known from WO 98/46608 receive.
  • reaction of II 'with amines III' is advantageously carried out at 0 0 C to 7O 0 C, preferably 1O 0 C to 35 0 C, preferably in the presence of an inert solvent such as ethers, eg. As dioxane, diethyl ether or especially tetrahydrofuran, halogenated hydrocarbons, such as dichloromethane and aromatic hydrocarbons, such as spielmud toluene.
  • ethers eg. As dioxane, diethyl ether or especially tetrahydrofuran, halogenated hydrocarbons, such as dichloromethane and aromatic hydrocarbons, such as spielmud toluene.
  • a base such as tertiary amines, for example triethylamine or inorganic bases, such as potassium carbonate, is preferred; Excess amine of the formula III 'can also serve as a base.
  • Amines of the formula III ' are commercially available.
  • Penconazole 1- [2- (2,4-dichloro-phenyl) -pentyl] -1 H- [1,2,4] triazole (Pesticide Manual, 12th
  • Prothioconazole 2- [2- (1-Chloro-cyclopropyl) -3- (2-chloro-phenyl) -2-hydroxypropyl] -2,4-dihydro- [1,2,4] triazole-3-thione (WO 96/16048);
  • Triflumizole (4-chloro-2-trifluoromethyl-phenyl) - (2-propoxy-1- [1,2,4] triazol-1-yl-ethylidene) -amine (JP-A 79/119 462);
  • Triticonazole 5- (4-chloro-benzylidene) -2,2-dimethyl-1- [1,2,4] triazol-1-ylmethylcyclopentanol (EP-A 378 953);
  • Azoxystrobin 2- ⁇ 2- [6- (2-cyano-1-vinyl-penta-1,3-dienyloxy) -pyrimidin-4-yloxy] -phenyl ⁇ -
  • Mefenoxam methyl N- (methoxyacetyl) -N- (2,6-xylyl) -D-alaninate (WO 96/01559);
  • 2,5 (or 2,6) -dimethylmorpholine and "alkyl” may also be octyl, decyl, tetradecyl or hexadecyl, and wherein the cis / trans ratio is 1: 1;
  • Dodemorph 4-cyclododecyl-2,6-dimethylmorpholine (DE 11 98 125); Fenpropimorph, 4- [3- (4-tert-butylphenyl) -2-methyl-propyl] -2,6-dimethyl-morpholine (DE 11 98 125);
  • Tridemorph a mixture of N-alkylmorpholine derivatives containing 2,6-
  • Dimethyl-4-tridecylmorpholine contains (DE-AS 11 64 152);
  • Mepanipyrim (4-methyl-6-prop-1-ynyl-pyrimidin-2-yl) -phenyl-amine (EP-A 224 339); Cyprodinil, (4-cyclopropyl-6-methyl-pyrimidin-2-yl) -phenyl-amine (EP-A 310550);
  • Maneb manganese ethylene bis (dithiocarbamate) (US 2 504 404); Mancozeb, manganese ethylene bis (dithiocarbamate) zinc complex (U.S. 3,379,610);
  • Metiram zinc ammonium ethylenebis (dithiocarbamate) (U.S. 3,248,400);
  • Propineb, zinc propylene bis (dithiocarbamate) polymer (BE 611 960);
  • Zineb zinc ethylene bis (dithiocarbamate) (US 2 457 674);
  • Mepronil 3'-isopropoxy-o-toluanilide (U.S. 3,937,840); Nuarimol, ⁇ - (2-chlorophenyl) - ⁇ - (4-fluorophenyl) -5-pyrimidinemethanol (GB 12 18 623);
  • Benthiavalicarb ⁇ (S) -1 - [(1R) -1- (6-fluoro-benzothiazol-2-yl) -ethylcarbamoyl] -2-methyl-propyl ⁇ -carbamic acid isopropyl ester (JP-A 09/323 984); Carpropamide, 2,2-dichloro- ⁇ / - [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide;
  • Chlorothalonil, 2,4,5,6-tetrachloroisophthalonitrile (US 3,290,353);
  • Iprovalicarb [(1S) -2-methyl-1- (1-p-tolyl-ethylcarbamoyl-O-propyl] -carbamic acid isopropyl ester (EP-A 472 996); hexachlorobenzene; Mandipropamide, 4-chloro-N- [2- [3-methoxy-4- (2-propynyloxy) phenyl] ethyl] - ⁇ - (2-propynyloxy) benzylacetamide (WO 03/042166);
  • Metrafenone 3-bromo-2,3,4,6'-tetramethoxy-2 ', 6-dimethylbenzophenone (U.S. 5,945,567);
  • Chlormoquat 2-chloroethyltrimethylammonium salt (US 3,395,009);
  • Mepiquat chloride 1, 1-dimethylpiperidinium chloride (DE 22 07 575); Diflufenzopyr, 2- ⁇ 1- [4- (3,5-difluorophenyl) semicarbazono] ethyl ⁇ nicotinic acid;
  • Benzoimidazolderivate of formula IIA (see EP-A 10 17 671); Sulfamoyl compounds of the formula III (cf., EP-A 10 31 571, JP-A 2001-192 381); Thiophene derivatives of formula IV (see JP 10130268); Oxime ether derivatives of the formula V (see WO 99/14188);
  • Phenylamidine derivatives of the formula VI (cf., WO 00/46184);
  • the mixtures of the compounds I and the active compounds from groups A) to R) or the simultaneous joint or separate use of the compounds I and the active compounds from the groups A) to R) are distinguished by an outstanding activity against a broad spectrum Spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Oomycetes and Basiliomycetes. They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides.
  • fungi are suitable for controlling the following phytopathogenic fungi: Blumeria graminis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphae- rotheca fuliginea on cucurbits, Podosphaera leucot ⁇ cha on apples, Uncinula necator on vines, Pucc / n / a species of cereals, Rhizoctonia acai on cotton, rice and turf, Ustilago acai on cereals and sugarcane, Venturia inaequalis on apples, Bipolaris and Drechslera aries on cereals, rice and turf, Sepfor / a species on wheat, Botrytis cinerea on strawberries, vegetables, ornamental plants and vines, Mycosphaerel / a species on bananas, peanuts and cereals, Pseudocercosporella herpotrichoides on wheat and barley, Pyricularia oryzae on rice, P ⁇ a /
  • the compound I and the active compounds from groups A) to R) can be applied simultaneously together or separately or in succession, the sequence generally not having any effect on the control result when applied separately.
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, 6, 8 or 10 carbon atoms, for example C 1 -C 6 -AlkVl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl , 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1 Methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3 Dimethylbutyl, 1-ethylbutyl,
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 2, 4 or 6 carbon atoms (as mentioned above), in which groups the hydrogen atoms may be partially or completely replaced by halogen atoms as mentioned above: in particular C 1 -C 2 Haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoro ethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2- Trichloroethyl
  • Alkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 6, 8 or 10 carbon atoms and one or two double bonds in any position, for example C 2 -C 6 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, 2 Pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl , 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butyl-, 1, 1-dimethyl-2-propenyl,
  • Haloalkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and one or two double bonds in any Positi ⁇ on (as mentioned above), wherein in these groups, the hydrogen atoms partially or completely against halogen atoms as mentioned above, in particular fluorine, chlorine and bromine , can be replaced;
  • Alkynyl straight-chain or branched hydrocarbon groups having 2 to 4, 6, 8 or 10 carbon atoms and one or two triple bonds in any position, for example C 2 -C 6 alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2 Butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl 3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl , 1-methyl-2-pentynyl
  • Cycloalkyl mono- or bicyclic, saturated hydrocarbon groups having 3 to 6 or 8 carbon ring members, for example C 3 -C 8 -cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;
  • 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom 5-membered heteroaryl groups which contain, in addition to carbon atoms, one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members can, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, and 1, 3,4-triazol-2-yl;
  • 6-membered heteroaryl containing one to three or one to four nitrogen atoms 6-membered ring heteroaryl groups, which in addition to carbon atoms may contain one to three or one to four nitrogen atoms as ring members, e.g. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl;
  • Alkylene divalent linear chains of 3 to 5 CH 2 groups, eg CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 and CH 2 CH 2 CH 2 CH 2 CH 2 ;
  • Oxyalkylene divalent unbranched chains of 2 to 4 CH 2 groups, wherein a Va ⁇ lenz is bound via an oxygen atom to the skeleton, for example OCH 2 CH 2 , OCH 2 CH 2 CH 2 and OCH 2 CH 2 CH 2 CH 2 ;
  • Oxyalkylenoxy divalent unbranched chains of 1 to 3 CH 2 groups, both valences being bonded to the skeleton via an oxygen atom, eg OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O;
  • Formula IIA represents compounds in which Y is bromo (11-1) or chloro (II-2).
  • formula III represents compounds in which the subscript n is 0, 1 or 2, preferably O or 1.
  • the group R 33 is preferably in the 5- or 6-position. These compounds are particularly suitable for use in the mixtures according to the invention.
  • R 31 is hydrogen, methyl, ethyl, n- or iso-propyl, fluorine, chlorine, bromine, iodine, methylthio, ethylthio, trifluoromethyl, pentafluoroethyl, cyano, phenyl or formyl.
  • R 32 is hydrogen, fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl or n-butoxycarbonyl.
  • R 33 is fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl, in particular fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl or methoxy.
  • mixtures of a compound I with at least one compound of the formula IV are present.
  • Ar is preferably phenyl or a five-membered aromatic heterocycle, in particular a five-membered heteroaryl radical, which is unsubstituted or substituted by one or two groups R 41 .
  • Ar preferably represents the following groups: phenyl, pyridine, pyrazine, furan, thiophene, pyrazole and thiazole.
  • Particularly preferred groups Ar are: 3-pyridinyl, pyrazinyl, 3-furyl, 3-thiophenyl, 4-pyrazolyl, 5-thiazolyl.
  • a group R 41 is ortho to the amide moiety.
  • Preferred groups R 41 are halogen, in particular chlorine, alkyl, in particular methyl, and halomethyl, in particular fluoromethyl, difluoromethyl or trifluoromethyl.
  • Preferred groups R are alkyl groups, in particular branched C 3 -C 8 -alkyl groups, in particular 4-methyl-pent-2-yl.
  • compounds IV.A in particular compounds of the formulas IV.A.1 and IV.B.1, in which R 41 can be identical or different and is methyl and halomethyl and R is alkyl, such as branched C 3 -C 8 -alkyl, in particular 4-methyl-pent-2-yl:
  • Particularly preferred compounds V are in particular the compounds listed in Table V below:
  • mixtures of a compound I are present with at least one compound of the formula VI.
  • FT 1 is hydrogen
  • R 62 is C 1 -C 6 -alkyl, such as methyl and ethyl, in particular methyl,
  • R 63 is C 1 -C 6 alkyl, such as methyl and ethyl, in particular ethyl;
  • R 64 is C 1 -C 6 -alkyl, in particular methyl
  • R 65 is C 1 -C 6 -alkyl, in particular methyl; m is 1, wherein R 65 is para to R 4 ;
  • A is oxygen (-O-);
  • R is phenyl, which is preferably unsubstituted or substituted by one to three groups R f , in particular by one or two groups R f ;
  • R f is halogen, in particular fluorine or chlorine, alkyl, in particular methyl, ethyl, n- and iso-propyl and tert. Butyl and haloalkyl, especially thfluoromethyl.
  • the groups R f are preferably in the 3- or 3,4-position.
  • mixtures of a compound I with at least one compound of formula VII are mixtures of a compound I with at least one compound of formula VII.
  • R 71 is n-propyl or n-butyl, in particular n-propyl.
  • R 73 is iodine or bromine, in particular iodine.
  • formula VII represents compounds of formulas VII.1, VII.2 and VI 1.3:
  • the compound of the formula VII.1 in which R 71 is n-propyl, R 72 is n-propoxy and R 73 is iodine, is also known under the common name proquinazide (compound VII.1-1). Mixtures of a compound of the formula I and proquinazide are a preferred embodiment of the invention.
  • a further preferred embodiment of the invention relates to mixtures of a compound I and one of the following compounds of the formula VII.3:
  • active compounds of the groups A) to R) selected from one of the following groups are preferred:
  • A) azoles such as bromoconazole, cyproconazole, difenoconazole, dinitroconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, flutriafol, hexaconazole, ipazanolazole, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothio-conazole, simeconazole, tebuconazole, tetraconazole, Triflumizole, triticonazole;
  • strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin;
  • C) acylalanines such as metalaxyl, mefenoxam;
  • D) amine derivatives such as dodine, fenpropimorph, fenpropidin, spiroxamine, tridemorph;
  • anilinopyrimidines such as pyrimethanil, mepanipyrim or cyprodinil
  • dicarboximides such as iprodione, procymidone, vinclozolin;
  • heterocyclic compounds selected from benomyl, boscalid, carbendazim, carboxin, cyazofamide, dithianone, fenarimol, flutolanil, penthiopyrad, picobenzamide, proquinazide, pyrifenox, quinoxyfen, thiophanate-methyl, benzoimidazole derivatives of the formula II, Sulfamoyl compounds of the formula III, M) sulfur and copper fungicides such as Bordeaux broth, copper acetate, copper oxychloride, basic copper sulfate; N) nitrophenyl derivatives such as dinocap; O) phenylpyrroles such as fenpiclonil or fludioxonil;
  • P) sulfenic acid derivatives such as captan, folpet, tolylfluanid
  • fungicides selected from benthiavalicarb, chlorothalonil, cyflufenamide, diclofluanide, fenhexamide, fluazinam, fosetyl, fosetyl-aluminum, phosphorous acid, iprovalicarb, metrafenone, pencycuron, oxime ether derivatives of formula V,
  • growth retardants such as Prohexadion calcium, Trinexapac-ethyl, Chlorme- quat, mepiquat chloride and Diflufenzopyr.
  • the compounds I and the active compounds of groups A) to R) are able to form salts or adducts with inorganic or organic acids or with metal ions because of the basic character of the nitrogen atoms or carboxylate groups contained in them.
  • inorganic acids examples include hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid.
  • suitable organic acids are formic acid, carbonic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid and 2-acetoxybenzoic acid into consideration.
  • acetic acid trifluoroacetic acid
  • glycolic acid lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid and 2-acetoxybenzoic acid into consideration.
  • the metal ions are in particular the ions of the elements of the first to eighth subgroup, in particular chromium, manganese, iron, cobalt, nickel, copper, zinc, the first main group, in particular lithium, sodium and potassium and the second main group, in particular calcium and magnesium third and fourth main group, in particular aluminum, tin and lead into consideration. If appropriate, the metal ions can be present in various valences.
  • the mixtures according to the invention may contain as active components further active components from compounds of the formula I and active compounds from groups A) to R).
  • One embodiment of the mixtures contains, in addition to a compound of the formula I and an active compound from the groups A) to R) as active components one or two, in particular an active compound from group A) to R).
  • the compound I and the active compound from groups A) to R) are usually employed in a weight ratio of from 100: 1 to 1: 100, preferably from 20: 1 to 1:20, in particular from 10: 1 to 1:10.
  • a weight ratio of from 100: 1 to 1: 100 preferably from 20: 1 to 1:20, in particular from 10: 1 to 1:10.
  • mixing ratios of 1000: 1 to 1: 1 come into question.
  • the further active components are added to compound I in a ratio of from 20: 1 to 1:20.
  • the application rates of the mixtures according to the invention are from 5 g / ha to 2000 g / ha, preferably from 50 to 900 g / ha, in particular from 50 to 750 g / 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 from groups A) to R) are correspondingly generally 1 to 2000 g / ha, preferably 10 to 900 g / ha, in particular 40 to 750 g / ha.
  • the application rates for Diflufenzopyr are usually 0.01 to 50 g / ha, preferably 0.1 to 10 g / ha
  • the method for controlling harmful fungi is carried out by the separate or common application of the compound I and the active compound from groups A) to R) or the mixtures of the compound I and the active compound from groups A) to R) by spraying or Dusting the seeds, plants or soils before or after sowing the plants or before or after emergence of the plants.
  • the mixtures according to the invention or the active components can be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the application form depends on the respective purpose; In any case, it should ensure a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, e.g. by stretching the active compound with solvents and / or excipients, if desired with use of emulsifiers and dispersants.
  • Suitable solvents / auxiliaries are essentially:
  • Fatty acid ester In principle, solvent mixtures can also be used
  • Excipients such as ground natural minerals (e.g., kaolins, clays, talc, chalk) and ground synthetic minerals (e.g., fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
  • ground natural minerals e.g., kaolins, clays, talc, chalk
  • ground synthetic minerals e.g., fumed silica, silicates
  • Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
  • the surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde , Condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl
  • mineral oil fractions of medium to high boiling point such as kerosine 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 derivatives thereof, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water.
  • mineral oil fractions of medium to high boiling point such as kerosine 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 derivatives thereof, methanol, ethanol
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics, fertilizers, such as e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as wheat flour, bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • Mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground
  • the formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredients.
  • the active compounds are employed in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • formulations according to the invention are: 1. Products for dilution in water
  • a Water-soluble concentrates (SL) 10 parts by weight of the active ingredients are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a formulation with an active substance content of 10% by weight.
  • the formulation has an active ingredient content of 15% by weight.
  • the active compounds 25 parts by weight of the active compounds 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 to water by means of an emulsifying machine (e.g., Ultraturax) in 30 parts by weight and made into a homogeneous emulsion. Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 25% by weight.
  • E Suspensions 20 parts by weight of the active compounds are comminuted to a fine suspension of active substance in an agitating ball mill with the addition of 10 parts by weight of dispersing and wetting agents and 70 parts by weight of water or an organic solvent. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • Water-dispersible and water-soluble granules 50 parts by weight of the active compounds are finely ground with the addition of 50 parts by weight of dispersing and wetting agents and prepared by means of industrial equipment (for example extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the formulation has an active ingredient content of 50% by weight.
  • WP, SP Water-dispersible and water-soluble powders 75 parts by weight of the active compounds are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • 0.5 parts by weight of the active ingredients are finely ground and combined with 99.5 parts by weight of carrier. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with an active ingredient content of 0.5 wt .-%.
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, misting, dusting, scattering or pouring.
  • the forms of application depend entirely on the intended use; In any case, they should ensure as far as possible the finest distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by addition of water.
  • 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.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • the compounds I and II or the mixtures or the corresponding formulations ⁇ K - approximations are applied by treating the harmful fungi or the of plants, seeds, soils, areas, materials or spaces with a fungicidally wirksa ⁇ amount of the mixture , or the compounds I and Ii with separate application treated.
  • the application can take place before or after infestation by the harmful fungi.
  • novel compounds of the formula I can be prepared analogously to the process known from US Pat. No. 5,593,996.
  • the instructions reproduced in the synthesis example below were used to obtain further compounds I with a corresponding modification of the starting compounds.
  • the compounds obtained in this way are listed in the following table with physical data.
  • aqueous active ingredient preparation which was prepared with a stock solution of 5% active ingredient, 94% acetone and 1% emulsifier (Tween 20). After the spray coating had dried (3-5 h), the leaves were inoculated with an aqueous spore suspension of Venturia inequalis. The test plants were then placed in climatic chambers at 22-24 ° C. and 95-99% relative atmospheric humidity for 2 days and then cultivated in the greenhouse at 21-23 ° C. and approximately 95% relative humidity for a further 2 weeks. Then the extent of infestation development on the leaves was visually determined.
  • test plants in Klima ⁇ chambers at 22 - 24 0 C and 96 - 99% relative humidity were set up for 36 hours and then cultivated in the greenhouse at 21 - 23 ° C and about 95% relative humidity for a further 2 to 3 days , Then the extent of infestation on the leaves was visually determined In this test, the plants treated with 200 ppm of the active ingredients 1-1, 1-2, 1-5, 1-6, 1-7, 1-9, and 1-11 showed a maximum of 15% infestation, while the untreated plants 90% were affected.
  • the active compounds were prepared separately or together as a stock solution with 0.25% by weight of active compound in acetone or DMSO. To this solution was added 1% by weight of emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and diluted with water according to the desired concentration.
  • emulsifier Uniperol® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • the active ingredients fosetyl-Al, epoxiconazole, triticonazole and pyraclostrobin were applied in their commercial formulation.
  • Leaves of potted plants of the "golden queen" variety were sprayed to drip point with an aqueous suspension in the concentration of active compound stated below. The following day, the leaves were infected with an aqueous spore suspension of Alternaria solani in 2% biomalt solution with a density of 0.17 x 10 6 spores / ml. Subsequently, the plants were placed in a water vapor-saturated chamber at temperatures between 20 and 22 ° C. After 5 days, the disease on the untreated, but infected control plants had developed so strongly that the infestation could be determined visually in%.
  • 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 those of the untreated control plants; at an efficiency of 100, the treated plants have no infestation.
  • Leaves of potted tomato plants were sprayed to drip point with an aqueous suspension in the drug concentration below. The following day, the leaves were infected with an aqueous sporangia suspension of Phytophthora infestans. Subsequently, the plants were placed in a water vapor-saturated chamber at temperatures between 18 and 20 0 C. After 6 days, the late blight on the untreated but infected control plants developed so strongly that the infestation could be determined visually in%.

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

Abstract

La présente invention concerne des mélanges fongicides contenant comme composantes actives : 1) une 5-chlor-6-phényl-7-hétérocyclylamino-triazolopyrimidine de formule (I) dans laquelle D forme avec l'atome d'azote, un noyau pyrrolidine, pipéridine ou azépine, ces noyaux étant non substitués ou substitués par un ou deux groupes méthyle ou par un groupe éthyle, propyle ou butyle, et L représente méthyle, fluor ou chlore ; et 2) au moins un principe actif II choisi dans les groupes A) azoles, B) strobilurines, C) acylalanines, D) dérivés d'amine, E) anilinopyrimidines, F) dicarboximides, G) amides d'acide cinamique et analogues, H) antibiotiques K) dithiocarbamates, L) composés hétérocyliques tels que définis dans le descriptif, M) fongicides au soufre ou au cuivre, N) dérivés de nitrophényle, O) phénylpyrroles, P) dérivés d'acide sulfénique, Q) autres fongicides tels que définis dans le descriptif ou R) retardateurs de croissance ; en une quantité synergiquement active. L'invention a également pour objet les nouvelles triazolopyrimidines, un procédé pour lutter contre les champignons nocifs au moyen des composés de formule (I) ou de mélanges d'un composé de formule (I) avec un principe actif des groupes A) à R), ainsi que l'utilisation des composés de formule (I) avec les principes actifs des groupes A) à R), pour préparer des mélanges de ce type, et des agents qui contiennent ces composés ou ces mélanges.
EP05773888A 2004-08-03 2005-07-28 Melanges synergiques fongicides composes de derives de triazolopyrmidine Withdrawn EP1788877A1 (fr)

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PCT/EP2005/008192 WO2006015728A1 (fr) 2004-08-03 2005-07-28 Melanges synergiques fongicides composes de derives de triazolopyrmidine

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EP (1) EP1788877A1 (fr)
KR (1) KR20070047819A (fr)
CN (1) CN1993050A (fr)
AR (1) AR050093A1 (fr)
AU (1) AU2005270459A1 (fr)
BR (1) BRPI0514067A (fr)
CA (1) CA2573929A1 (fr)
EA (1) EA200700383A1 (fr)
IL (1) IL180368A0 (fr)
MX (1) MX2007000061A (fr)
WO (1) WO2006015728A1 (fr)

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US7598206B2 (en) 2004-12-23 2009-10-06 Basf Aktiengesellschaft Fungicidal mixtures
GB0508993D0 (en) 2005-05-03 2005-06-08 Syngenta Participations Ag Pesticidal compositions
EP1980150A1 (fr) * 2007-04-13 2008-10-15 Basf Se Mélanges fongicides basés sur des composés de triazolopyrimidines
CN101743973B (zh) * 2010-01-05 2013-03-13 陕西美邦农资贸易有限公司 一种含戊菌唑与百菌清的杀菌组合物

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Publication number Priority date Publication date Assignee Title
US5593996A (en) * 1991-12-30 1997-01-14 American Cyanamid Company Triazolopyrimidine derivatives
DE59702388D1 (de) * 1997-05-14 2000-10-26 Basf Ag Verfahren zur herstellung graphitpartikel enthaltender expandierbarer styrolpolymerisate
WO1998051735A1 (fr) * 1997-05-14 1998-11-19 Basf Aktiengesellschaft Polymerisats de styrene expansibles contenant des particules de graphite
PT988790E (pt) * 1998-09-25 2003-10-31 Basf Ag Misturas fungicidas
DE19908183A1 (de) * 1999-02-25 2000-08-31 Basf Ag Wässrige Polymerdispersionen
DE10124208A1 (de) * 2001-05-18 2002-11-21 Bayer Ag Verwendung von Triazolopyrimidin-Derivaten als Mikrobizide
WO2004045288A2 (fr) * 2002-11-15 2004-06-03 Basf Aktiengesellschaft Melanges fongicides pour lutter contre des pathogenes du riz
MXPA05004369A (es) * 2002-11-15 2005-07-05 Basf Ag Mezclas fungicidas.
WO2004045282A2 (fr) * 2002-11-15 2004-06-03 Basf Aktiengesellschaft Melanges fongicides
CN1316886C (zh) * 2002-11-15 2007-05-23 巴斯福股份公司 基于咪唑衍生物的杀真菌混合物
CN1711022A (zh) * 2002-11-15 2005-12-21 巴斯福股份公司 用于防治稻病原体的杀真菌混合物

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IL180368A0 (en) 2007-07-04
MX2007000061A (es) 2007-03-28
BRPI0514067A (pt) 2008-05-27
KR20070047819A (ko) 2007-05-07
AU2005270459A1 (en) 2006-02-16
WO2006015728A1 (fr) 2006-02-16
CA2573929A1 (fr) 2006-02-16
US20080249113A1 (en) 2008-10-09
EA200700383A1 (ru) 2007-08-31
AR050093A1 (es) 2006-09-27
CN1993050A (zh) 2007-07-04

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