EP2442653A2 - Fungizide mischungen - Google Patents

Fungizide mischungen

Info

Publication number
EP2442653A2
EP2442653A2 EP10725155A EP10725155A EP2442653A2 EP 2442653 A2 EP2442653 A2 EP 2442653A2 EP 10725155 A EP10725155 A EP 10725155A EP 10725155 A EP10725155 A EP 10725155A EP 2442653 A2 EP2442653 A2 EP 2442653A2
Authority
EP
European Patent Office
Prior art keywords
methyl
chlorophenyl
fluorophenyl
phenyl
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP10725155A
Other languages
German (de)
English (en)
French (fr)
Inventor
Jochen Dietz
Egon Haden
Jens Renner
Sarah Ulmschneider
Alice GLÄTTLI
Marianna Vrettou-Schultes
Silke Stolz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP10725155A priority Critical patent/EP2442653A2/de
Publication of EP2442653A2 publication Critical patent/EP2442653A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • A01N37/34—Nitriles
    • 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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Definitions

  • the present invention relates to pesticidal compositions, especially fungicidal compositions comprising as active components
  • A is phenyl, 2-fluorophenyl, 2-chlorophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-
  • R is hydrogen, C -C -alkyl 8 -alkyl, Ci-C 8 haloalkyl, C 2 -C 8 alkenyl,
  • Each phenyl group is unsubstituted or substituted by one, two or three groups independently selected from halogen and C 1 -C 4 alkyl;
  • a and B are as defined above; - a group of Dil where # is the point of attachment to the triazolyl ring and Q, R 1 and R 2 are
  • R 1, R 2 independently of one another Ci -Ce-Al kyl, d-Cs-haloalkyl, Cr Cs-alkoxy, Ci-C8-alkoxy-CrC 8 alkoxy, Ci-C8-haloalkoxy, CrC 8 -
  • M is an alkali metal cation, one equivalent of an alkaline earth metal cation, one equivalent of a copper, zinc, iron or nickel cation or an ammonium cation of the formula (E)
  • Z 1 and Z 2 are independently hydrogen or C 1 -C 8 alkyl
  • Z 3 and Z 4 are independently hydrogen, C 1 -C 8 alkyl, benzyl or phenyl; wherein the phenyl groups are each unsubstituted or substituted by one, two or three groups independently selected from halogen and C 1 -C 4 alkyl;
  • A) strobilurins azoxystrobin, dimoxystrobin, coumoxystrobin, coumethoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, 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- methyl methoxyacrylate, methyl 3-methoxy-2- (2- (N- (4-methoxy-phenyl) -cyclopropanecarboximidoylsulfanylmethyl
  • Carboxylic acid amides - carboxylic anilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid,
  • Carboxin Fenfuram, Fenhexamide, Flutolanil, Furametpyr, Isopyrazam, Isotianil, Kiralaxyl, Mepronil, Metalaxyl, Metalaxyl-M (Mefenoxam), Ofurace, Oxadixyl, Oxycarboxine, Penthiopyrad, Sedaxane, Tecloftalam, Thifluzamide, Tiadinil, 2-Amino-4 -methyl-thiazole-5-carboxanilide, 2-chloro-N- (1,1,3-trimethyl-indan-4-yl) nicotinamide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,
  • 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; C) Azoles:
  • Triazoles azaconazole, bitertanol, bromobonazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole , Tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1- (4-chlorophenyl) -2 - ([1, 2,4] triazol-1-yl) -cycloheptanol;
  • - imidazoles cyazofamide, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizole;
  • Benzimidazoles benomyl, carbendazim, fuberidazole, thiabendazole;
  • - Pyrroles fludioxonil, fenpiclonil
  • - morpholines aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph
  • Dicarboximides fluorimide, iprodione, procymidone, vinclozolin;
  • non-aromatic 5-membered heterocycles famoxadone, fenamidone, flutianil, octhilinone, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydropyrazole-1-thiocarboxylic acid allyl ester;
  • acibenzolar-S-methyl acibenzolar-S-methyl, amisulbrom, anilazine, blasticidin-S, captafol, captan, quinomethionate, dazomet, debacarb, diclomethine, difenzoquat, difenzoate methyl sulfate, fenoxanil, folpet, oxolinic acid, piperaline, proquinazide, pyroquilone, quinoxyfen , Triazoxide, tricyclazole, 2-butoxy-6-iodo-3-propyl-chromen-4-one, 5-chloro-1- (4,6-dimethoxypyrimidin-2-yl) -2-methyl-1 H- benzoimidazole, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyr
  • Fungicides - Guanidines Dodine, Dodine Free Base, Guazatin, Guazatin Acetate, Iminoctadine, Iminoctadine Triacetate, Iminoctadin Tris (Albesilat);
  • Nitrophenyl derivatives binapacryl, diclorane, dinobutone, dinocap, nitrothal-isopropyl, tecnazene;
  • fentin salts such as fentin acetate, fentin chloride, fentin hydroxide
  • Sulfur-containing heterocyclyl compounds dithianone, isoprothiolanes
  • Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, phosphorous acid and its salts, pyrazophos, tolclofos-methyl;
  • Organochlorine compounds chlorothalonil, dichlofluanid, dichlorophene, flusulphamide, Hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phthalide, quintozene, thiophanate-methyl, tolylfluanid, N- (4-chloro-2-nitro-phenyl) -N-ethyl-4-methyl-benzenesulfonamide;
  • Inorganic active ingredients phosphorous acid and its salts, Bordeaux broth, copper salts such as copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
  • 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, cyhalofopbutyl, 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,
  • Dinitroanilines Benfluralin, Ethalfluralin, Oryzalin, Pendimethalin, Prodiamine, Trifluralin; Diphenyl ether: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;
  • Hydroxybenzonitriles bromoxynil, dichlobenil, loxynil;
  • Imidazolinones 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, picloram, picolinafen, thiazopyr;
  • Sulfonylureas amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl,
  • Triazines ametryn, atrazine, cyanazine, dimethametryn, ethiozine, hexazinone, metachronon, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam;
  • Ureas chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron, tebuthiuron;
  • acetolactate synthase bispyribac sodium, cloransulam methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, orthosulphamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxime, pyriftalid, pyriminobac-methyl, pyrimisulphane, pyrithiobac, pyroxasulphone, pyroxsulam;
  • Carbamates alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamates; Pyrethroids: allethrin, betacyfluthrin, bifenthrin, cyfluthrin, cyhalothrin,
  • Insect growth inhibitors a) chitin synthesis inhibitors: benzoylureas: chlorofluorazuron, cyramazine, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; Buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozid, methoxyfenozide, tebufenozide, azadirachtin; c) Juvenoids: Pyriproxyfen,
  • Nicotine receptor agonists / antagonists clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1- (2-chlorothiazol-5-ylmethyl) -2-nitrimino-3,5-dimethyl- [1, 3 , 5] triazinane;
  • 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;
  • METI II and III substances Acequinocyl, Fluacyprim, Hydramethylnon;
  • Inhibitors of oxidative phosphorylation cyhexatin, diafenthiuron, fenbutatin oxide, propargite;
  • Inhibitors of the sloughing of insects Cryomazine; Inhibitors of mixed function oxidases: piperonyl butoxide;
  • Cyenopyrafen Flupyrazofos, Cyflumetofen, Amidoflumet, Imicyafos, Bistrifluron and Pyrifluquinazone, [(3S, 4R, 4aR, 6S, 6aS, 12R, 12aS, 12bS) -3-
  • component 2 is defined as follows:
  • Biological fungicides, plant strengtheners Ampelomyces quis- qualis (. Eg the product AQ 10 ® from Intrachem Bio GmbH & Co. KG Germany,), Aspergillus flavus (. Eg the product AFLAGUARD ® from Syngenta, Switzerland), Aureobasidium pullulans (eg the product BOTECTOR ® from. bio-ferm GmbH, Germany), Bacillus pumilus (eg strain NRRL no. B-30087 ® in SONATA ®, and BALLAD Plus from. AgraQuest Inc., USA), Bacillus subtilis (eg master NRRL no.
  • Candida saitoana eg the products BIOCURE ® (mixed with lysozyme) and BIOCOAT ® Micro Flo Company USA (BASF SE) companies, and Arysta
  • chitosan eg ARMOR-ZEN from BotriZen Ltd., New Zealand
  • Clonostachys rosea f. catenulata also called Gliocladium catenulatum (eg strain J1446. PresTop ® from Verdera, Finland), Coniothyrium minitans (.
  • Pseudozyma flocculosa eg the product SPORODEX ® from. Plant Products Co. Ltd., Canada
  • Pythium oligandrum DV74 eg the product POLYVERSUM ® from. Remeslo SSRO, Biopreparaty, Czech Republic
  • Reynoutria sachlinensis eg the product REGALIA ® from Marrone Biolnnovations, USA
  • Talaromyces flavus V117b eg the product protus ® of Fa. Prophyta, Germany
  • Trichoderma asperellum SKT-1 eg, the product ECO-HOPE ® from. Kumiai Chemical Industry Co., Ltd., Japan
  • Atroviride LC52 (eg the product SENTINEL ® from. Agrimm Technologies Ltd., New Zealand), T. harzianum T-22 (eg the product PLANT SHIELD ® from BioWorks Inc., USA), T. harzianum TH 35 (eg the product ROOT PRO ® from MyControl Ltd., Israel), T. harzianum T-39 (for example, the products TRICHODEX ® and TRICHODERMA 2000 ® from. MyControl Ltd., Israelites l and Makhteshim Ltd., Israel), T. harzianum and T. viride (eg the product TRICHOPEL the company Agrimm Technologies Ltd, New Zealand), T. harzianum and T.
  • viride ICC012 ICC080 (eg the product restageer ® WP Fa. Isagro ricerca, Italy), T. polysporum and T. harzianum (eg the product Binab ® from. Binab Bio-innovation AB, Sweden), T. stromaticum (eg the product TRICOVAB ® from Ceplac, Brazil), T. virens GL- 21 (eg the product SOILGARD ® from Certis LLC, USA), T. viride (eg the products TRIECO ® from Ecosense Labs. (India) Pvt. Ltd., India and BIO-CURE ® F from. T. Stanes & Co. Ltd., India), T.
  • viride TV1 eg the product T. viride TV1 company Agribiotec srl, Italy
  • Ulocladium oudemansii HRU3 eg the product BOTRY- ZEN ® of Botry-Zen Ltd Company, New Zealand
  • components 1) and 2) are present in a synergistically effective amount.
  • the invention relates to the use of the fungicidal mixtures for controlling phytopathogenic fungi and agents or compositions containing them. Furthermore, the invention also relates to seed containing the fungicidal mixtures. Furthermore, the invention also relates to methods for controlling phytopathogenic fungi, characterized in that the fungi, or to be protected against fungal attack materials, plants, the soil or seeds treated with an effective amount of a fungicidal mixture according to the invention. Furthermore, the invention also relates to processes for the preparation of the mixtures according to the invention.
  • mixtures comprising at least one compound of the formula I (component 1) and at least one further active compound II (component 2 and optional component 3) are mixtures according to the invention.
  • Mixtures according to the invention are furthermore mixtures comprising at least one compound of the formula I (component 1) and three further independently selected, different active compounds II (components 2, 3 and 4).
  • Particularly preferred are the binary mixtures according to the invention.
  • ternary mixtures according to the invention are preferred.
  • mixtures according to the invention may also contain at least one further compound II as additional
  • Components include, wherein the compound II of the additional components (eg, component 4 or components 4 or 5) is selected from the above compounds of groups A) to I), provided that in that all components are different from each other.
  • the present invention relates to synergistic mixtures which, in addition to the above-defined 3 components, also contain a further compound II as the 4th component, this component 4 being selected from the above-defined compounds of groups A) to I), under which
  • the invention relates to fungicidal mixtures comprising 1) Azolylmethyloxirane of the general formula I as described above, and
  • the invention also relates to fungicidal mixtures comprising 1) Azolylmethyloxirane of the general formula I as described above, and
  • the present invention furthermore relates to the use of the compounds I-A for controlling phytopathogenic fungi and to compositions or compositions containing them. Furthermore, the invention also relates to seed containing the compounds of the formula I-A according to the invention. Furthermore, the invention also relates to methods for controlling phytopathogenic fungi, which comprises treating the fungi or the materials, plants, the soil or seeds to be protected from fungal attack with an effective amount of a compound of the formula I-A according to the invention. Furthermore, the invention also relates to processes for the preparation of the compounds of the formula I-A according to the invention.
  • the invention also relates to processes for the preparation of the compounds of the formula I.
  • the preparation of the compositions containing certain compounds of the formula I is carried out in a known manner as indicated for the preparation of the compositions of the mixtures according to the invention, in the form of compositions containing in addition to the active ingredient or the active ingredients, a solvent or solid carrier.
  • a solvent or solid carrier With regard to the usual ingredients of such compositions, reference is made to the comments on the compositions comprising the mixtures according to the invention.
  • compositions for mixtures of active substances are suitable as fungicides for controlling harmful fungi.
  • fungicides plant diseases to be treated, plants to be treated, mode of application, effects
  • component 2 (and optional further component 3 and
  • Component 4 or as "further active ingredient” (compounds II)) mentioned active ingredients, their preparation and their action against harmful fungi are known (see: 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 mixtures were the object, which show an improved action against harmful fungi, especially for certain indications with reduced total amount of applied drugs.
  • the fungicidal action of the compounds known from the prior art leaves something to be desired in some cases. It is an object of the present invention to provide novel compounds which preferably have improved properties as having a better fungicidal action and / or better toxicological properties. Due to the general problem that fungicidal compounds often lead to resistance in practice after some time, it is a further object of the present invention to provide new alternative compounds which can be used effectively as fungicides in agriculture. This object has surprisingly been achieved with the novel compounds described herein.
  • 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 active ingredient (component 2 and optional component 3), eg. One or more, e.g. 1 or 2 active ingredients of the abovementioned groups A to I and optionally one or more agriculturally suitable carriers. Furthermore, the present invention also relates to fungicidal compositions containing at least one compound of the general formula I and at least three further active ingredients (components 2, 3 and 4), the abovementioned groups A to I and optionally one or more agriculturally suitable carriers.
  • Common application in the context of this application means that at least one compound I and the at least one other active ingredient II at the same time at the site of action (ie the fungi to be controlled and their habitat such as infested plants, plant propagation materials, insebesondere seed, soil, materials or rooms and the before Fungal attack on plants to be protected, plant propagation materials, in particular seeds, soil, materials or spaces) in an amount sufficient for effective control of fungal growth.
  • the site of action ie the fungi to be controlled and their habitat such as infested plants, plant propagation materials, insebesondere seed, soil, materials or rooms and the before Fungal attack on plants to be protected, plant propagation materials, in particular seeds, soil, materials or spaces
  • the temporal Order of application of the active ingredients is of minor importance.
  • compositions according to the invention comprising a compound I and another active ingredient II (component 2), e.g. contain an active ingredient from groups A) to I).
  • component 2 e.g. contain an active ingredient from groups A) to I.
  • the weight ratio of compound I to further active ingredient II depends on the properties of the respective active ingredients, usually in the range from 1: 100 to 100: 1, frequently in the range from 1:50 to 50: 1, preferably in the range from 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. It may be preferred if the weight ratio is in the range of 1: 2 to 2: 1.
  • compositions according to the invention comprising an active substance I and a further active ingredient (component 2) and a second further active ingredient (component 3), eg. B. contain two different agents from groups A) to I).
  • the weight ratio of compound I to the first further active ingredient (component 2) depends on the properties of the respective active ingredients, preferably in the range from 1: 100 to 100: 1, preferably in the range from 1:50 to 50: 1 and in particular in the range from 1:20 to 20: 1, in particular from 1:10 to 10: 1. It may be preferred if the weight ratio is in the range from 1: 3 to 3: 1, in particular 1: 2 to 2: 1.
  • the weight ratio of compound I to the second further active ingredient (component 3) is preferably in the range from 1: 100 to 100: 1, preferably in the range from 1:50 to 50: 1, in particular in the range from 1:20 to 20: 1 , in particular 1:10 to 10: 1. It may be preferred if the weight ratio is in the range from 1: 3 to 3: 1, in particular 1: 2 to 2: 1.
  • the weight ratio of further active ingredient (component 2) to the second further active ingredient (component 3) is preferably in the range from 1: 100 to 100: 1, preferably in the range from 1:50 to 50: 1, in particular in the range from 1 : 20 to 20: 1, more preferably 1:10 to 10: 1. It may be preferred if the weight ratio is in the range from 1: 3 to 3: 1, in particular 1: 2 to 2: 1.
  • these are quaternary mixtures, ie compositions according to the invention which contain an active substance I and a further active ingredient II (component 2), a second further active ingredient II (component 3) and a third further active ingredient II ( Component 4), these three active substances II being different active substances which are selected independently from groups A) to I).
  • the weight ratio of compound I to the first further active ingredient (component 2) depends on the properties of the respective active ingredients, preferably in the range from 1: 100 to 100: 1, preferably in the range from 1:50 to 50: 1 and in particular in the range from 1:20 to 20: 1, in particular from 1:10 to 10: 1.
  • the weight ratio is in the range from 1: 3 to 3: 1, in particular 1: 2 to 2: 1.
  • the weight ratio of compound I to 2. further active ingredient (component 3) is preferably in the range from 1: 100 to 100: 1, preferably in the range from 1:50 to 50: 1, in particular in the range from 1:20 to 20: 1, in particular from 1:10 to 10 :1. It may be preferred if the weight ratio is in the range from 1: 3 to 3: 1, in particular 1: 2 to 2: 1.
  • the weight ratio of compound I to the third further active ingredient (component 4) is preferably in the range from 1: 100 to 100: 1, preferably in the range from 1:50 to 50: 1, in particular in the range from 1:20 to 20: 1 , in particular 1:10 to 10: 1. It may be preferred if the weight ratio is in the range from 1: 3 to 3: 1, in particular 1: 2 to 2: 1.
  • the weight ratio of further active ingredient (component 2) to the second further active ingredient (component 3) is preferably in the range from 1: 100 to 100: 1, preferably in the range from 1:50 to 50: 1, in particular in the range from 1 : 20 to 20: 1, more preferably 1:10 to 10: 1.
  • the weight ratio is in the range of 1: 3 to 3: 1, especially 1: 2 to 2: 1.
  • the weight ratio of further active ingredient (component 2) to the third further active ingredient (component 4) is preferably in the range from 1: 100 to 100: 1, preferably in the range from 1:50 to 50: 1, in particular in the range from 1 : 20 to 20: 1, more preferably 1:10 to 10: 1. It may be preferred if the weight ratio is in the range from 1: 3 to 3: 1, in particular 1: 2 to 2: 1.
  • the weight ratio of the second further active ingredient (component 2) to the third further active ingredient (component 4) is preferably in the range from 1: 100 to 100: 1, preferably in the range from 1:50 to 50: 1, in particular in the range from 1 : 20 to 20: 1, more preferably 1:10 to 10: 1. It may be preferred if the weight ratio is in the range from 1: 3 to 3: 1, in particular 1: 2 to 2: 1.
  • 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 may contain one or more, even all, components which can be used to prepare an agrochemical composition according to 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
  • adjuvant component fungicidal component
  • insecticidal component / or a growth regulator component and / or a herbicide.
  • a growth regulator component / or a herbicide
  • Kits may contain one or more separate containers such as jars, bottles, cans, bags, sacks or canisters, each container being a separate component of the agrochemical Composition contains.
  • 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.
  • kit mix Mix parts of a kit or a mixture of two or three 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 A) to I), 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 A) to I), together (for example as tank mix) or in succession.
  • the compounds of the formula I can be present in the "thiol" form of the formula Ia or in the "thiono" form of the formula Ib:
  • D * represents : - R, wherein R has the meaning defined above; - a group DN * where # is the point of attachment with the sulfur atom in formula Ia or azolyl ring in formula Ib and Q, R 1 and R 2 have the meaning defined above; or
  • the compounds I 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 contained in them. This also applies to most of the precursors for compounds I described herein, of which the salts and adducts are also subject of the present invention.
  • inorganic acids examples include 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, for example, formic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid and other arylcarboxylic acids, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids with straight-chain or branched alkyl radicals having 1 to 20 carbon atoms).
  • ArylsulfonTalkren or -disulfonklaren aromatic radicals such as phenyl and naphthyl, which carry one or two sulfonic acid groups
  • alkylphosphonic acids phosphonic acids having straight-chain or branched alkyl radicals having 1 to 20
  • aryl phosphonic acids or diphosphonic acids aromatic radicals such as phenyl and naphthyl bearing one or two phosphoric acid residues
  • alkyl or aryl radicals may carry further substituents, e.g. p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.
  • 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 Subgroups of the fourth period.
  • the metals can be present in the various valences that belong to them.
  • the compounds I contain chiral centers, with the trans configuration being preferred.
  • the compounds I are generally in the form of racemates or as
  • Diastereomer mixtures of erythro and threo forms 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. From such uniform pairs of diastereomers can be obtained by known methods uniform enantiomers. As antimicrobial agents can be used both the uniform diastereomers or enantiomers as well as their resulting in the synthesis of mixtures. The same applies to the fungicides.
  • the invention therefore relates both to mixtures in which compound I are the pure enantiomers or diastereomers as well as mixtures thereof.
  • the scope of the present invention includes the mixtures of the (R) and (S) isomers and the racemates of the compounds I which have chiral centers.
  • Suitable compounds I also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.
  • the compounds of the formula I according to the invention can be prepared as described in DE19520097, WO97 / 41 107, WO97 / 42178, WO97 / 43269, WO97 / 44331, WO97 / 44332 or WO99 / 05149, or in various ways in analogy to processes known per se of the prior art (see, for example, the cited prior art and crop protection news Bayer 57/2004, 2, pages 145-162) are produced.
  • the preparation of the compound I-A can be carried out as follows starting from compounds I-A.1, wherein A and B are defined as described for I-A:
  • a compound IA.1 is reacted with C 2 H 5X, where X is a leaving group such as, for example, halogen, such as Cl, Br or I, or trifluoro-C 1 -C 6 -alkyl sulfonate.
  • X is a leaving group such as, for example, halogen, such as Cl, Br or I, or trifluoro-C 1 -C 6 -alkyl sulfonate.
  • a compound IA.1 is reacted with an ethyl halide (see also WO 96/38440).
  • a compound IA.1 the corresponding unsulphured triazole NA reacted with a strong base and sulfur powder. This produces compounds of the formula IA.1.
  • Suitable bases are all suitable bases known to those skilled in the art for such reactions.
  • strong alkali metal bases such as n-butyl lithium, lithium diisopropylamide, sodium hydride, sodium amide or potassium tert-butoxide are used. It may be preferable to carry out the reaction in the presence of an additive such as tetramethylethylenediamide (TMEDA).
  • TMEDA tetramethylethylenediamide
  • Suitable solvents are all customary for such reactions inert organic solvents, preferably ethers such as tetrahydrofuran, dioxane, diethyl ether and 1, 2-dimethoxyethane or liquid
  • Ammonia or strongly polar solvents such as dimethyl sulfoxide can be used.
  • Sulfur is preferably used as a powder.
  • Hydrolysis is carried out using water, if appropriate in the presence of an organic or inorganic acid such as, for example, acetic acid, dilute sulfuric acid or dilute hydrochloric acid.
  • the reaction temperature is preferably between -70 0 C and + 20 0 C, in particular between -70 0 C and 0 0 C.
  • the reaction is generally carried out under atmospheric pressure. In general, 1 to 3 equivalents, preferably 1 to 2.5 equivalents, of strong base and then an equivalent amount or an excess of sulfur are used per 1 mole of the compound of formula NA.
  • the reaction can be carried out under a protective gas atmosphere, for example under nitrogen or argon.
  • the workup is carried out according to methods generally known to the person skilled in the art. Usually, the reaction mixture is extracted with a suitable organic solvent and the residue is optionally purified by recrystallization and / or
  • Suitable bases are all suitable bases known to those skilled in the art for such reactions.
  • strong alkali metal bases such as n-butyl lithium, lithium diisopropylamide, sodium hydride, sodium amide or potassium tert-butoxide are used. It may be preferable to carry out the reaction in the presence of an additive such as tetramethylethylenediamine (TMEDA).
  • TEDA tetramethylethylenediamine
  • the disulfides are commercially available or synthesized by known manufacturing methods.
  • reaction temperature is preferably between -70 0 C and + 20 0 C, in particular between -70 ° C and 0 0 C.
  • the reaction is in
  • reaction Generally carried out under normal pressure. In general, 1 to 3 equivalents, preferably 1 to 2.5 equivalents, of strong base and then an equivalent amount or an excess of disulfide are used per mole of the compound of the formula N-A.
  • the reaction may be carried out under a protective gas atmosphere, e.g. under nitrogen or argon.
  • the workup is carried out according to methods generally known to the person skilled in the art. Usually, the reaction mixture is extracted with a suitable organic solvent and the residue is optionally purified by recrystallization and / or chromatography.
  • 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; 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-fluoroethyl, 2,2-difluoroethyl , 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1, 1 , 1-
  • alkenyl groups such as (C 2 -C 4) alkenyl
  • larger alkenyl groups such as (C 5 -C 8) alkenyl
  • alkenyl groups are, 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-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1
  • Haloalkenyl alkenyl 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;
  • Alkynyl and the alkynyl moieties in assembled 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 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-
  • Cycloalkyl and the cycloalkyl moieties in assembled groups mono- or bicyclic, saturated hydrocarbon groups having 3 to 8, in particular 3 to 6 carbon ring members, for example C 3 -C6 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl;
  • Halogencycloalkyl cycloalkyl 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;
  • Alkoxy for an oxygen-bonded alkyl group as defined above, 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; as well as e.g.
  • 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-ethylbutoxy, 2-ethylbutoxy, 1 , 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;
  • 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. Examples of these are OCH 2 F, OCHF 2 , OCF 3 , OCH 2 Cl, OCHCl 2 , OCCl 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2
  • Alkylene divalent unbranched chains of CH 2 groups.
  • (C 1 -C 6) -alkylene more preferred is (C 2 -C 4) -alkylene, furthermore it may be preferable to use (C 1 -C 3) -alkylene groups.
  • preferred alkylene radicals are CH 2, CH 2 CH 2, CH 2 CH 2 CH 2, CH 2 (CH 2) 2 CH 2, CH 2 (CH 2) 3 CH 2 and CH 2 (CH 2) 4 CH 2;
  • A is phenyl, 2-fluorophenyl, 2-chlorophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 3-chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 4 Methylphenyl or 4-tert-butylphenyl.
  • A is phenyl, 4-fluorophenyl, 2-chlorophenyl or 4-chlorophenyl.
  • A is phenyl. In a further preferred embodiment, A is 4-fluorophenyl. In a further preferred embodiment, A is 2-chlorophenyl. In a further preferred embodiment, A is 4-chlorophenyl.
  • B is 2-fluorophenyl, 2-chlorophenyl or 2-bromophenyl.
  • B is 2-chlorophenyl
  • D is a group SR, where R is hydrogen (compounds I-SH).
  • R is hydrogen
  • the present invention therefore relates to mixtures of the compounds of the formula I, in which D denotes SH.
  • D is a group SR, where R is C 1 -C 4 -alkyl, in particular methyl or ethyl, preferably methyl.
  • R 3 is hydrogen.
  • R 3 is Ci-C 4 -AlkVl, in particular methyl or ethyl, preferably methyl.
  • R 3 is C 1 -C 4 -haloalkyl, in particular trifluoromethyl.
  • R 3 is C 1 -C 4 -alkoxy, in particular methoxy or ethoxy.
  • R 3 is methylamino, dimethylamino, ethylamino, diethylamino or phenylamino.
  • D is a group SR, where R is CN.
  • D is a group SR, where R is SO 2 R 4 and R 4 is C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkyl or phenyl, where the phenyl groups are each unsubstituted or are substituted by one, two or three groups independently selected from halogen and C 1 -C 4 -alkyl.
  • D is a group SM wherein M is an alkali metal cation, one equivalent of an alkaline earth metal cation
  • Z 1 and Z 2 are independently hydrogen or C 1 -C 4 -alkyl; and Z 3 and Z 4 are independently hydrogen, C 1 -C 4 alkyl, benzyl or phenyl.
  • M represents Na, 1 ⁇ 2Cu, 3Fe, HN (CH 3 ) S, HN (C 2 H 5 ) S, N (CHs) 4 or H 2 N (C 3 HT) 2 , in particular Na, 1/2 Cu, HN (CHs) 3 or HN (C 2 Hs) 3 , especially Na, 1/2 Cu, HN (CHs) 3 or HN (C 2 Hs) 3 .
  • D stands for a group D1
  • both A or both B in the compounds l-dimer have the same meaning.
  • D is a group Dil, where # is the point of attachment to the triazolyl ring and Q, R 1 and R 2 are as defined herein or preferably defined:
  • the present invention also provides the following individualized in Table I-A
  • the invention also relates to mixtures which comprise as component 1 at least one of the compounds of the formula I-A according to the invention, as listed in the individual rows of the preceding Table I-A.
  • the invention also relates in particular to mixtures of the compounds of the formula I according to the invention, as listed in the individual rows of Table C.
  • R 3 is C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy,
  • R 4 is d-C ⁇ -alkyl.
  • M is an alkali metal cation, one equivalent of an alkaline earth metal cation, one equivalent of a copper, zinc, iron or nickel cation or an ammonium cation of the formula (E)
  • Z 1 and Z 2 are independently hydrogen or Ci-Cs-alkyl
  • Z 3 and Z 4 are independently hydrogen, C 1 -C 8 alkyl, benzyl or phenyl; wherein the phenyl groups are each unsubstituted or substituted by one, two or three groups independently selected from halogen and C 1 -C 4 -alkyl;
  • A is phenyl, 4-fluorophenyl or 4-phenyl, 4-fluorophenyl, 2-chlorophenyl or 4-chlorophenyl,
  • R 3 is Ci-Cs-alkyl, Ci-Cs-alkoxy, R 4 Ci-Cs-alkyl.
  • A is phenyl, 4-fluorophenyl or 4-phenyl, 4-fluorophenyl, 2-chlorophenyl or 4-chlorophenyl,
  • R 3 is methyl or methoxy
  • R 4 is methyl
  • A is phenyl, 4-fluorophenyl, 2-chlorophenyl or 4-chlorophenyl, B 2-chlorophenyl.
  • R 3 is methyl or methoxy
  • R 4 is methyl
  • mixtures of the compounds of formula I (or IA) (component 1) wherein the variables have the following meanings: A phenyl, 4-fluorophenyl, 2-chlorophenyl or 4-chlorophenyl, B 2-chlorophenyl. D -SC 2 H 5 .
  • the most preferred compounds of the formula I are the following compounds 1-1 to 1-18, wherein in each case in particular enantiomer pairs or enantiomers with trans arrangement of ring A and ring B are preferred: 1-1 trans-2- [3- ( 2-chlorophenyl) -2- (4-fluorophenyl) -oxiranylmethyl] -2,4-dihydro-
  • the invention relates to a compound of formula I wherein A is 4-fluorophenyl, B is 2-chlorophenyl and D is S-CN.
  • the invention relates to the compound I-6 trans-1- [3- (2-chlorophenyl) -2- (4-fluorophenyl) -oxiranylmethyl] -5-thiocyanato-1 H- [1,2,4] triazole, as well as their use for controlling phytopathogenic fungi and agents or compositions containing them.
  • the invention also relates to seed containing the compound I-6.
  • the invention also relates to methods for controlling phytopathogenic fungi, characterized in that treating the fungi, or to be protected against fungal attack materials, plants, the soil or seeds with an effective amount of the compound I-6. Furthermore, the invention also relates to processes for the preparation of the compound I-6. In a further preferred embodiment, the invention relates to a compound IA (ie a compound I, wherein D stands for SC2H5), in particular the compound 1-18, as well as their use for controlling phytopathogenic fungi and agents or compositions containing them. Furthermore, the invention also relates to seed containing the compound IA, in particular 1-18. Furthermore, the concerns
  • the invention also relates to a method for controlling phytopathogenic fungi, which comprises treating the fungi or the materials, plants, the soil or seeds to be protected from fungal attack with an effective amount of a compound I-A, in particular 1-18.
  • compositions of a compound I (component 1) with at least one active compound from group A) (component 2 and / or 3 and or component 4) of strobilurins, and more particularly selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin.
  • compositions of a compound I with at least one active compound selected from the group B) (component 2 and / or 3 and / or component 4) of the carboxamides and especially selected from bixafen, boscalid, isopyrazam, fluopyram, penflufen, Penthiopyrad, sedaxane, fenhexamide, metalaxyl, mefenoxam, ofurace, dimethomorph, flumorph, fluopicolide (picobenzamide), zoxamide, carpropamide, mandipropamide and N- (3 ', 4', 5'-trifluorophenyl-2-yl) -3- difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide.
  • compositions of a compound I with at least one active compound selected from the group C) (component 2 and / or 3 and / or component 4) of the azoles and especially selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, Flutriafol, metconazole,
  • Myclobutanil penconazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamide, benomyl, carbendazim and ethaboxam.
  • compositions of a compound I with at least one active ingredient selected from group D) (component 2 and / or 3 and / or component 4) 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, proquinazid, acibenzolar-S-methyl, captafol, folpet, fenoxanil, quinoxyfen and 5-ethyl-6-octyl- [1, 2,4] triazolo [1,5-a] pyrimidin-7-ylamine.
  • compositions of a compound I with at least one active ingredient selected from the group E) (component 2 and / or 3 and / or component 4) of the carbamates and especially selected from mancozeb, metiram, propineb, thiram, iprovalicarb, Benthiavalicarb and Propamocarb.
  • compositions of a compound I with at least one active ingredient selected from the fungicides of group F) (component 2 and / or 3 and / or component 4) and especially selected from dithianone, fentin salts, such as fentin acetate, fosetyl , Fosetyl-aluminum, H3PO3 and its salts, chlorothalonil, dichlofluanid, thiophanate-methyl, copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, cymoxanil, metrafenone, spiroxamine and N-methyl-2- ⁇ 1 - [(5-methyl-3 -trifluoromethyl-1H-pyrazol-1-yl) -acetyl] -piperidin-4-yl ⁇ -N - [(1R) -1, 2,3,4-tetrahydronaphthalen-1-yl] -4-thiazolecarboxamide.
  • compositions according to the invention comprise a compound I (component 1), and a component 2, wherein the component 2 is an insecticide selected from group I).
  • component 1 component 1
  • component 2 is an insecticide selected from group I
  • these are binary mixtures comprising as active ingredients a component 1) and a component 2) which is selected from group I).
  • the insecticide of component 2) is selected from the group of organo (thio) phosphates, in particular selected from acephate, chlorpyrifos, diazinon, dichlorvos, dimethoate, fenitrothion, methamidophos, methidathion, methyl parathion, monocrotophos, phorates, profenofos and terbufos.
  • organo (thio) phosphates in particular selected from acephate, chlorpyrifos, diazinon, dichlorvos, dimethoate, fenitrothion, methamidophos, methidathion, methyl parathion, monocrotophos, phorates, profenofos and terbufos.
  • the insecticide of component 2) is selected from the group of carbamates, in particular selected from aldicarb, carbaryl, carbofuran, carbosulfan, methomyl and thiodicarb.
  • the insecticide of component 2) is selected from the group of pyrethroids, in particular selected from: bifenthrin, cyfluthrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, lambda-cyhalothrin and tefluthrin.
  • the insecticide of component 2) is selected from the group of inhibitors of insect growth, in particular selected from lufenuron and spirotetramat.
  • the insecticide of component 2) is selected from the group of nicotine receptor agonists / antagonists, in particular selected from: clothianidin, imidacloprid, thiamethoxam and thiacloprid.
  • the insecticide of component 2) is selected from the group of GABA antagonists, in particular selected from: endosulfan and fipronil.
  • the insecticide of component 2) is selected from the group of macrocyclic lactones, in particular selected from: abamectin, emamectin, spinosad and spinetoram.
  • the insecticide of component 2) is hydramethylnone.
  • the insecticide of component 2) is fenbutatin oxide.
  • the insecticide of component 2) is selected from chlorfenapyr, cyazypyr (HGW86), cyflumetofen, flonicamid, flubendiamide, indoxacarb and metaflumizone.
  • these are ternary mixtures which, in addition to the components mentioned, comprise a component 3) which is selected from the above-mentioned active compounds II of group I).
  • these are ternary mixtures which, in addition to the two components mentioned, comprise a component 3) which is selected from the active compounds II of groups A) to G).
  • Pesticidal action is disclosed in WO2006 / 129714 and WO2009 / 081851.
  • component 2 is a fungicide selected from groups A to F.
  • a component 3 is present, in a further preferred embodiment it is an independently selected fungicide selected from groups A to F. In a further preferred embodiment, components 2 and 3 are two fungicides selected from groups A to F.
  • a component 4 is present, in a further preferred embodiment it is an independently selected fungicide selected from groups A to F. In a further preferred embodiment, components 2, 3 and 4 are three fungicides independently selected from groups A to F. ,
  • the present invention further relates to compositions of a compound I (component 1) with a further active ingredient (component 2), the latter selected from lines A-1 to A-359 in the column "component 2" of Table A.
  • a further embodiment of The invention relates to the compositions A-1 to A-359 listed in Table A, wherein in each case one row of Table A corresponds to an agrochemical composition comprising an individualized in the present specification compound of formula I (component 1) and in each case in the respective Line indicated further active ingredient from groups A) to I) (component 2).
  • the active ingredients in the described compositions are each preferably present in synergistically effective amounts.
  • Particularly preferred components 2 are compounds II which are selected from the group of the following compounds:
  • Particularly preferred mixtures are the binary mixtures of Table B, wherein each line corresponds to one embodiment of the mixtures according to the invention.
  • Table B Binary mixtures comprising a component 1 selected from compounds of the formula I and a component 2 selected from the groups A to
  • composition II which are selected from the group of the following compounds:
  • Table B1 Binary mixtures comprising a component 1 selected from compounds of the formula I and a component 2 selected from the groups A to
  • composition II which are selected from the group of the following compounds:
  • Table B2 Binary mixtures comprising a component 1 selected from
  • composition II which are selected from the group of the following compounds:
  • particularly preferred components 2 are compounds II which are selected from the group of the following compounds:
  • Particularly preferred mixtures are the binary mixtures of Table B3, each line corresponding to one embodiment of the mixtures according to the invention.
  • Table B3 Binary mixtures comprising a component 1 selected from preferred compounds of the formula I and a component 2 selected from the group I)
  • particularly preferred components 2 are compounds II selected from the group of the following compounds: II-32a clothianidin II-33a dinotefuran II-34a Imidacloprid II-35a Thiamethoxam II-36a Nitenpyram II-37a Acetamiprid II-38a Thiacloprid
  • Particularly preferred mixtures are the binary mixtures of Table B4, each line corresponding to one embodiment of the mixtures according to the invention.
  • Table B4 Binary mixtures comprising a component 1 selected from preferred compounds of formula I and a component 2 selected from group I.
  • particularly preferred components 2 are compounds II which are selected from the active ingredients of group H).
  • the active compounds according to this embodiment are selected from the group of the following compounds of group H):
  • Particularly preferred mixtures are the binary mixtures of Table B5, each line corresponding to one embodiment of the mixtures according to the invention.
  • Table B5 Binary mixtures comprising a component 1 selected from preferred compounds of the formula I and a component 2 selected from the group H.
  • the invention relates to fungicidal mixtures comprising a component 1, as well as component 2 (compound II) and a further component 3 (further component 3), with the proviso that component 2 and component 3 are not the same.
  • the present invention further relates to compositions of a compound I (component 1) with two further active compounds selected from the compounds II (component 2 and component 3).
  • the present invention relates to compositions of the mixtures of the compounds I and II described as being preferred with a further active compound II. Particularly preferred are ternary mixtures.
  • a further embodiment of the invention relates to the compositions T-1 to T-359 listed in Table T, wherein in each case one row of Table T corresponds to an agrochemical composition comprising a mixture of the compounds of the formula I and the compounds II individualized in the present specification (Component 1 and 2) and the further active ingredient in each case from the groups A) to I) (component 3).
  • the active ingredients in the described compositions are each preferably present in synergistically effective amounts.
  • the invention relates to the composition of the mixtures B-1 to B-359 with a further compound II, which is selected from the lines T-1 to T-359 in the column "component 3" of Table T, particularly preferably selected from Compounds 11-1 to II-29.
  • components 2 and 3 are not the same.
  • Table T Ternary mixtures comprising an individualized mixture of component 1 and component 2 (mixture B), and a component 3 selected from groups A to I:
  • Component 3 is a compound II which is selected from the group of the following compounds:
  • component 2 and component 3 are not the same.
  • Table T1 The following ternary mixtures T1-1 to T1-1881, comprising as component 1 the compound I, a component 2 selected from the group 2 to group I active compounds preferred for component 2 and a component 3 selected from those for component
  • component 1 the compound I
  • component 2 selected from the group 2 to group I active compounds preferred for component 2
  • component 3 selected from those for component
  • T1 The following ternary mixtures T1-1882 to T1-3036 comprising, as component 1, a compound I, a component 2 selected from the group 2 to group I active compounds preferred for component 2, and a component 3 selected from those for Component 3 preferred active ingredients of groups A to I.
  • component 1 a compound I
  • component 2 selected from the group 2 to group I active compounds preferred for component 2
  • component 3 selected from those for Component 3 preferred active ingredients of groups A to I.
  • K stands for "component”
  • M stands for" mixture ".
  • component 3 is a compound II which is selected from the group of the following compounds:
  • Table T2 The following ternary mixtures T2-1 to T2-825 comprising, as component 1, the compound I, a component 2 selected from the active ingredients preferred for component 2 and a component 3 selected from active ingredients preferred for component 3.
  • component 1 the compound I
  • component 2 selected from the active ingredients preferred for component 2
  • component 3 selected from active ingredients preferred for component 3.
  • K stands for "component”
  • M stands for" mixture ".
  • component 2 is a compound II which is selected from the group of the following compounds:
  • component 3 is a compound II selected from the group of the following compounds: II-30a fipronil II-32a Clothianidin II-34a Imidacloprid II-35a Thiamethoxam
  • Table T3 The following ternary mixtures T3-1 to T3-396 comprising as component 1 a preferred compound I, a component 2 selected from component 2 preferred active ingredients and a component 3 selected from component 3 preferred active ingredients.
  • component 1 a preferred compound I
  • component 2 selected from component 2 preferred active ingredients
  • component 3 selected from component 3 preferred active ingredients.
  • K stands for "component”
  • M stands for" mixture ".
  • component 2 is a compound II which is selected from the group of the following compounds: II-32a clothianidin II-34a imidacloprid II-35a thiamethoxam, and component 3 fipronil (compound ll-30a).
  • Table T4 The following ternary mixtures T4-1 to T4-33, comprising as component 1 a preferred compound I, and component selected from preferred active compounds II of group I) and fipronil as third component.
  • component 1 a preferred compound I
  • component selected from preferred active compounds II of group I preferred active compounds II of group I
  • fipronil preferred active compounds II of group I
  • component 2 is a compound II which is selected from the group of the following compounds:
  • 11-51 is penthiopyrad and component 3 is fipronil (Compound ll-30a).
  • Table T5 The following ternary mixtures T5-1 to T5-99, comprising as component 1 a preferred compound I, and component selected from the preferred active compounds II of group I) and fipronil as the third component.
  • component 1 a preferred compound I
  • component selected from the preferred active compounds II of group I a preferred active compounds II of group I
  • fipronil a preferred active compounds II of group I
  • Particularly preferred components 4 are compounds II which are selected from the group of the following compounds:
  • Penflufen provided that components 2, 3 and 4 are different active substances.
  • Table Q The following quaternary mixtures Q-1 to Q-2244 comprising as component 1 a compound I, a component 2 selected from preferred active compounds of groups A to I, a component 3 selected from preferred active compounds of groups A to I. and one component 4, selected from the group A to component I preferred components for component 4.
  • component 1 a compound I
  • component 2 selected from preferred active compounds of groups A to I
  • component 3 selected from preferred active compounds of groups A to I
  • component 4 selected from the group A to component I preferred components for component 4.
  • K stands for " Component
  • M stands for "mixture”.
  • component 3 is a compound II selected from among
  • Table Q1 The following quaternary mixtures Q1-1 to Q1-297 comprising, as component 1, a preferred compound I, a component 2 selected from preferred active compounds of groups A to F, a component 3 selected from preferred active substances of groups I) and fipronil as component 4.
  • component 1 a preferred compound I
  • component 2 selected from preferred active compounds of groups A to F
  • component 3 selected from preferred active substances of groups I
  • fipronil as component 4.
  • one row of a quaternary mixture according to the invention corresponds to the respective mixing components 1 to 4 in the row in question.
  • K stands for "component”
  • M stands for" mixture ".
  • the mixtures of compounds I and II are suitable as fungicides for controlling harmful fungi. They are distinguished by outstanding activity against a broad spectrum of phytopathogenic fungi, including soil-borne pathogens, which in particular originate from the classes of the Plasmodiophoromycetes, Peronosporomycetes (Syn. Oomycetes), Chytriomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (Syn. Fungi imperfecti). They are sometimes systemically effective and can be used in the Crop protection can be used as foliar, pickling and soil fungicides. In addition, they are suitable for controlling fungi that attack, among other things, the wood or the roots of plants.
  • mixtures according to the invention and the compositions of the invention for combating a variety of pathogenic fungi on various crops such as cereals, eg. Wheat, rye, barley, triticale, oats or rice; Beets, z. Sugar or fodder beets; Kernel, stone and berry fruits, z. Apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, currants or gooseberries; Legumes, z. Beans, lentils, peas, alfalfa or soybeans; Oil plants, e.g.
  • 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, grapefruit or mandarins
  • Vegetables, z. Spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, squash or paprika;
  • Laurel family z. Avocados, cinnamon or camphor; 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.
  • 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.
  • flowers, shrubs, deciduous and coniferous trees and on the propagation material for. B. seeds, and the crop of these plants.
  • the mixtures or compositions of the invention for controlling a variety of fungal pathogens in crops, z.
  • 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.
  • the treatment of plant propagating materials with mixtures or compositions of the invention is used to combat a variety of fungal pathogens in cereal crops, e.g. 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 those on the market or in development biotechnological agricultural products (see for example http://www.bio.org/speeches/pubs/ er / agri_products.asp).
  • Genetically modified plants are plants whose genetic material has been altered in a way that does not occur under natural conditions by crossing, mutations or natural recombination (ie recomposition 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 modifications also include post-translational modifications of proteins, oligo- or polypeptides, for example by means of glycolsylation or binding of polymers such as prenylated, acetylated or farnelysed residues or PEG residues.
  • plants may be mentioned which, by breeding and genetic engineering measures, tolerate certain herbicide classes, such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as eg. As sulfonylureas (EP-A 257 993, US 5,013,659) or
  • Imidazolinones eg US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073), enolpyruvylshikimate-3-phosphate synthase (EPSPS) -nnhibitorsen such. Glyphosate (see, for example, WO 92/00377), glutamine synthetase (GS) inhibitors such as.
  • EPSPS enolpyruvylshikimate-3-phosphate synthase
  • 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 RoudupReady ® (glyphosate-resistant, Monsanto, USA) and Liberty Link ® ( Glufosinate-resistant, Bayer CropScience, Germany).
  • RoudupReady ® glyphosate-resistant, Monsanto, USA
  • Liberty Link ® Glufosinate-resistant, Bayer CropScience, Germany.
  • 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. Insecticidal proteins of Bacillus spp., In particular B. thuringiensis such as the endotoxins CrylAb, CrylAc, CrylF, Cry1Fe2, 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.
  • VIP1, VIP2, VIP3, or VIP3A insecticidal proteins of nematode-colonizing bacteria
  • Photorhabdus spp. or Xenorhabdus spp . Toxins from animal organisms, eg. B. Wepsen, spider or scorpion toxins; fungal toxins, e.g. B. from streptomycetes; herbal lectins, e.g. From pea or barley; agglutinins; Proteinase inhibitors, e.g. Trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; Ribosome Inactivating Proteins (RIPs), e.g.
  • RIPs Ribosome Inactivating Proteins
  • 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). Other examples of such toxins or genetically engineered plants producing these toxins are described in EP-A
  • 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 toxins which Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin N-acetyltransferase [PAT] produce); 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); VIPCOT ® (cotton varieties that produce a VIP toxin); NewLeaf ® (potato cultivars producing the Cry3A toxin); Bt-Xtra ®, NatureGard® ®, KnockOut ®, Bit
  • 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. B. so-called pathogenesis-related proteins (PR proteins, see EP-A 0 392 225), Resistance proteins (eg, potato varieties that produce two resistance genes against Phytophthora infestans from the Mexican wild potato Solanum bulbocastanum) or T4 lysozyme (eg, potato varieties that are resistant to bacteria such as Erwinia amylvora as a result of the production of this protein). Furthermore, plants are included whose productivity with the help of genetic engineering
  • yield eg biomass, grain yield, starch, oil or protein content
  • tolerance to drought e.g., drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens
  • plants are also included whose ingredients are used in particular for
  • the mixtures or compositions according to the invention are particularly suitable for controlling the following plant diseases:
  • Albugo spp. White rust on ornamental plants, vegetable crops (e.g., A. candida) and sunflowers (e.g., A. 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. (Earhogs)
  • Botrytis cinerea teleomorph: Botryotinia 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 Ophiostoma
  • spp. Bläuepilz
  • deciduous and coniferous trees z. C. ulmi (elm dying, Dutch elm disease) on elms
  • Cercospora spp. Cercospora leaf spot) on maize (e.g., C. zeae mayans), rice, sugar beets (e.g., C. beticola), sugar cane, vegetables, coffee, soybeans (e.g., C. sojina or C. kikuchii), and rice
  • Cladosporium spp. on tomato eg C. fulvum:
  • Velvet spot disease and cereals, e.g. BC herbarum (earwax) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (Anamorph: Helminthosporium or Bipolaris) spp. (Leaf spot) on corn (e.g., BC carbonum), cereals (e.g., BC sativus, anamorph: B. sorokiniana: brown spot) and rice (e.g., BC miyabeanus, anamorph: H. oryzae); Colletotrichum (Teleomorph: Glomerella) spp.
  • ampelina burning 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, Anamorph: Cytosporina lata, Syn. Libertella blepharis) on fruit trees, vines and many ornamental shrubs; Exserohilum (Syn.
  • Helminthosporium) spp. on maize eg BE turcicum
  • Fusarium (Teleomorph: Gibberella) spp. Wild, root and stalk rot
  • BF graminearum or F. culmorum root rot and pigeon or whitish sprout
  • F. oxysporum on tomatoes
  • F. solani on soybeans
  • F. verticillioides on maize
  • Gaeumannomyces graminis blackleg
  • cereals eg BG zeae
  • rice eg BG fujikuroi: Bakanae disease
  • BH vastatrix (coffee leaf rust) of coffee; Isariopsis clavispora (Syn. Cladosporium vitis) on grapevine; Macrophomina phaseolina (Syn. Phaseoli) (root / stem rot) on soybeans and cotton; Microdochium (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
  • bulbous plants for example BP destructor
  • tobacco for example P. tabacina
  • soybeans for example P. manshurica
  • 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 (culm shift, 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 Pseudopezicula 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 (net stains) on barley; Pyricularia spp., E.g. BP oryzae (teleomorph: Magnaporthe grisea, rice leaf-fire) on rice and P. grisea on lawn and cereals; Pythium spp. (Turnip disease) on turf, rice, corn, wheat, cotton, oilseed rape, sunflower, sugar beets, vegetables and other plants (eg BP ultimum or P.
  • Pyrenophora anamorph: Drechslera
  • tritici-repentis leaf drought
  • P. teres net stains
  • Pyricularia spp. E.g. BP oryzae (teleomorph: Magnaporthe grisea, rice leaf-fire) on rice and P. grisea on lawn and cereals
  • BR solani root / stem rot
  • R. solani leaf-sheathing
  • 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) on vegetables and crops such as oilseed rape, sunflowers (eg Sclerotinia sclerotiorum) 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; Setospaeria spp. (Leaf spot) on maize (e.g., 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, maydis: corn buckthorn brandy) and sugarcane; Venturia spp. (Scab) on apples (eg BV inaequalis) and pears; and Verticillium spp. (Deciduous and cloudy) on various plants, such as fruit and ornamental trees, vines, soft fruit, vegetables and
  • Cultivated crops such as. B. V. dahliae on strawberries, rape, potatoes and tomatoes.
  • the mixtures or compositions according to the invention are also suitable for controlling harmful fungi in the storage protection (also of crops) and in the protection of materials and buildings.
  • material and building protection covers the protection of technical and non-living materials such. As adhesives, glues, wood, paper and cardboard, textiles, leather, color dispersions, plastics, coolants, fibers and tissues, against the infestation and destruction by unwanted microorganisms such as fungi and bacteria.
  • 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.
  • the compounds of the formula I, and also those of the formula II, can be present in various crystal modifications whose biological activity may be different. Their mixtures are included in the scope of the present invention.
  • the mixtures or compositions according to the invention are suitable for
  • the invention relates to a method for enhancing plant health by treating the plants, the plant propagating material and / or the place where the plants are to grow or grow with an effective amount of the compounds I or the compositions according to the invention.
  • 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 application can be both before and after the infection of plants, plant propagating materials, eg. As seeds, the soil, surfaces, materials or spaces treated with a fungicidally effective amount of the mixture according to the invention.
  • the application can be both before and after the infection of plants, plant
  • Propagating materials eg. As seeds, the soil, the surfaces, materials or spaces made by the fungi.
  • Plant propagating materials may be used prophylactically together with or already before sowing or together with or even before transplanting with the mixtures according to the invention as such or with a composition of them (composition containing at least one compound I and at least one compound II, preferably one or two compounds II).
  • the invention relates to agrochemical compositions containing a solvent or solid carrier and the mixture according to the invention and their use for controlling harmful fungi.
  • An agrochemical composition contains a fungicidally effective amount of the mixture according to the invention.
  • the expression "effective amount” means an amount of the agrochemical composition or mixture according to the invention 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 vary widely and are influenced by numerous factors, such as the harmful fungus to be controlled, the particular crop or material being treated, climatic conditions and compounds.
  • the compounds I and the one or more compounds 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 of controlling harmful fungi is by the separate or combined application of the compound I and the compound (s) II or the mixtures of the compound I and the compound (s) II by spraying or dusting the seeds, the plants or the soil or after sowing the plants or before or after emergence of the plants.
  • the compounds I and II may 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 compounds I and the compounds II and their N-oxides and salts or mixtures thereof can be converted into the types customary for agrochemical compositions, eg. As solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the type of composition depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compounds of the mixtures according to the invention.
  • composition types are suspensions (SC, OD, FS), emulsifiable concentrates (EC), emulsions (EW, EO, ES), pastes, pastilles, wettable powders or dusts (WP, SP, SS, WS, DP, DS) or granules (GR, FG, GG, MG) which may be either soluble or dispersible in water or gels for the treatment of plant propagating materials such as seeds (GF).
  • composition types eg EC, SC, OD, FS, WG, SG, WP, SP, SS, WS, GF
  • composition types such as DP, DS, GR, FG, GG and MG are generally used undiluted.
  • 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. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th ed., McGraw-Hill , New York, 1963, 8-57 and et seq., WO 91/13546, US 4,172,714, US 4,144,050, US 3,920,442, US 5,180,587, US 5,232,701, US 5,208,030, GB 2,095,558, US 3,299,566, Klingman: Weed Control as a Science ( John Wiley & Sons, New York, 1961), Hance et al .: Weed Control Handbook (8th Ed., Blackwell Scientific Publications, Oxford, 1989), and Mollet, H.
  • compositions may furthermore also comprise auxiliaries customary for crop protection agents, the choice of auxiliaries being directed at the specific application form or the active ingredient.
  • 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 medium to high boiling point mineral oil fractions such as kerosene and diesel oil, coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives,
  • Alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, gycols, ketones such as cyclohexanone, gamma-butyrolactone, dimethyl fatty acid amides, fatty acids and fatty acid esters, and strong polar solvents, e.g. Amines such as N-methylpyrrolidone, into consideration.
  • solvent mixtures and mixtures of the abovementioned solvents and water can also be used.
  • Solid carriers are mineral soils 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.
  • mineral soils 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
  • surfactants are the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, eg. B. of lignin (Borresperse ® grades, Borregaard, Norway), phenol, naphthalene (Morwet ® types, Akzo Nobel, USA) and dibutyl (nekal ® types, BASF, Germany), and of fatty acids, alkyl - And alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols and of Fettalkoholglykolethern, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or the
  • Naphthalenesulfonic acids with phenol and formaldehyde polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, Tributylphenylpolyglykolether, Alkylarylpolyetheralkohole, Isotridecylalkohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene or Polyoxypropylenalkylether, Laurylalkoholpolyglykoletheracetat, sorbitol esters, lignin sulfite liquors and proteins, denatured proteins, polysaccharides (eg
  • Methylcellulose hydrophobically modified starches, polyvinyl alcohol (Mowiol ® types, Clariant, Switzerland), polycarboxylates (Sokalan ® types, BASF, Germany), polyalkoxylates, polyvinylamine (Lupamin ® types, BASF, Germany), polyethyleneimine (Lupasol ® - Types, BASF, Germany), polyvinylpyrrolidone and copolymers thereof.
  • 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 (Proxel ® from. Messrs. ICI or Acetide ® RS from Thor Chemie and Kathon ® MK from. Rohm & Haas), and isothiazolinone derivatives such as
  • 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 designations Rhodamine B, CI Pigment Red 1 12 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 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 are 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, XyIoI, 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 into consideration. Powders, litter and dusts can be mixed or mixed
  • Milling the compounds I and the other active ingredients II are prepared with at least one solid carrier.
  • Granules for. As coated, impregnated and homogeneous granules can be prepared by binding the active ingredients 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, 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 cornmeal, tree bark, wood and nut shell meal, 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 sulfate, magnesium oxide, ground plastics
  • composition types are: 1. Compositions for dilution in water i) Water-soluble concentrates (SL, LS) 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 composition with 10 wt .-% active ingredient content. ii) Dispersible Concentrates (DC) 20 parts by weight of the active compounds are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant z. B. dissolved polyvinylpyrrolidone. Dilution in water gives a dispersion. The active ingredient content is 20% by weight iii) Emulsifiable Concentrates (EC) 15 parts by weight of the active compounds are dissolved in 75 parts by weight of xylene with the addition of
  • Dodecylbenzenesulfonate and castor oil ethoxylate (each 5 parts by weight) dissolved. 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 .-%.
  • suspensions (SC, OD, FS) 20 parts by weight of the active ingredients are comminuted with the addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the composition is 20% by weight.
  • 50 parts by weight of the active ingredients are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and prepared by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or
  • the composition has an active ingredient content of 50% by weight.
  • WP Water-dispersible and water-soluble powders (WP, SP, SS, WS)
  • composition types for direct application ix dusts (DP, DS)
  • compositions of the mixtures according to the invention generally contain from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the compounds I and II or mixtures thereof.
  • the compounds I and II are preferred in a purity of 90% to 100%, preferably 95% to 100% used (NMR spectrum).
  • compositions 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
  • DS dusts
  • WS water-dispersible and water-soluble powders
  • ES emulsions
  • EC emulsifiable concentrates
  • gels GF
  • Wt .-% active ingredient are present.
  • 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 compounds I and II or their mixtures can be used as such or in the form of their compositions, for. B. in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules by spraying, atomizing, dusting, scattering, coating, dipping or pouring.
  • the composition types 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 (wettable powders, oil dispersions) by adding water.
  • the substances for the preparation of emulsions, pastes or oil dispersions, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be successfully used in the ultra-low-volume (ULV) process. It being possible to dispense compositions containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • the application rates in the application in crop protection depending on the nature of the desired effect between 0.001 and 2.0 kg of active ingredient 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.
  • ⁇ In the treatment of plant propagation materials, eg. B. state, are generally drug amounts (or drug mixing amounts) of 0.1 to 1000 g / 100 kg of propagating material or seed, preferably 1 to 1000 g / 100 kg, more preferably 1 to 100 g / 100 kg, in particular 5 bis 100 g / 100 kg used.
  • the application rate of active ingredient or active ingredient mixture depends on the type of application and the desired effect. Usual application rates are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated in the material protection.
  • As adjuvants in this sense are in particular: organically modified polysiloxanes, eg. B. Break Thru S 240® ; Alcohol alkoxylates, eg. B. Atplus 245 ®, Atplus MBA ® 1303 Plurafac ® LF 300 ® and Lutensol ON 30; EO-PO
  • Block polymers z. B. Pluronic RPE 2035 ® and Genapol B ®; Alcohol ethoxylates, eg. B. Lutensol ® XP 80; and sodium dioctylsulfosuccinate, e.g. B. Leophen ® RA.
  • the starting product 1 - [(2S, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-ylmethyl] -1H- [1,2,4] triazole can be prepared as described, for example, in US Pat in the cited prior art or in WO 2007/147841 (PCT / EP2007 / 056124), WO 2007/147769 (PCT / EP2007 / 055870) and WO 2007/147778 (PCT / EP2007 / 055932) or analogously thereto.
  • the active ingredients were formulated separately or together as stock solution with a concentration of 10,000 ppm in DMSO.
  • the active ingredient orysastrobin was used as a commercial formulation and diluted with respect to the active ingredient with water.
  • the determined values (measured parameters) for the percentage infestation on the leaves were compared with the growth of the active ingredient-free control variant and the fungus-free and active ingredient-free blank value in order to determine the relative growth in% of the
  • 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.
  • E x + y - xy / 100 expected efficiency, expressed as% of untreated control, using the mixture of active substances A and B at concentrations a and b, expressed as% of untreated control, using active substance A at concentration a, efficiency in% of the untreated control, when using the active substance B in the concentration b
  • 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.
  • 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 Pyrenophora teres.
  • 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 was measured at 405 nm on the 7th day after inoculation of the MTPs. The measured parameters were compared with the growth of the drug-free control variant (100%) and the fungus-free and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.
  • Compound 1-18 showed 11% growth at 31 ppm.
  • the active ingredients were prepared separately or together with a stock solution
  • Example of application G1 - activity against the gray mold on pepper leaves caused by Botrytis cinerea in protective application (Botrci P1)
  • paprika seedlings were sprayed to drip point with an aqueous suspension in the concentration of active compound specified below.
  • the treated plants were inoculated with a spore suspension of Botrytis cinerea in 2% biomalt solution.
  • the test plants were placed in a climatic chamber at 22 to 24 ° C, darkness and high humidity. After 5 days, the extent of fungal attack on the leaves could be determined visually in%.
  • Leaf spot disease of wheat caused by Septoria tritici Leaves of potted wheat seedlings were sprayed to drip point with aqueous suspension in the concentration of active compound given below. 24 hours after the spray coating had dried on, they were inoculated with an aqueous spore suspension of Septoria tritici. The test plants were then placed in the greenhouse for 4 days at temperatures between 18 and 22 ° C and a relative humidity near 100%, then at temperatures between 18 and 22 0 C and a relative humidity of about 70%. After 21 days, the extent of disease development was determined visually as% of total leaf area. The compound I-6 (diastereomer mixture "trans”) showed an infection of 0% at 150 ppm, whereas the untreated control was 60% affected.
  • the active ingredients were formulated separately as stock solution with a concentration of
  • 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.
  • the plates were 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 measured parameters were compared with the growth of the drug-free control variant (100%) and the fungus-free and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.

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PE20120625A1 (es) 2012-05-20
KR20120046175A (ko) 2012-05-09
CA2764541A1 (en) 2010-12-23
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US20120088662A1 (en) 2012-04-12
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ZA201200305B (en) 2013-03-27
JP2012530101A (ja) 2012-11-29
EA201200020A1 (ru) 2012-07-30
AR077150A1 (es) 2011-08-03
BRPI1009688A2 (pt) 2015-10-27
WO2010146006A2 (de) 2010-12-23
UY32722A (es) 2010-12-31

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