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WO2011069916A1 - Composés triazoles, leur utilisation comme fongicides et agents les contenant - Google Patents

Composés triazoles, leur utilisation comme fongicides et agents les contenant Download PDF

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Publication number
WO2011069916A1
WO2011069916A1 PCT/EP2010/068853 EP2010068853W WO2011069916A1 WO 2011069916 A1 WO2011069916 A1 WO 2011069916A1 EP 2010068853 W EP2010068853 W EP 2010068853W WO 2011069916 A1 WO2011069916 A1 WO 2011069916A1
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WIPO (PCT)
Prior art keywords
compounds
individualized compound
methyl
chlorophenyl
phenyl
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PCT/EP2010/068853
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German (de)
English (en)
Inventor
Jochen Dietz
Thomas Grote
Egon Haden
Bernd Müller
Jan Klaas Lohmann
Jens Renner
Richard Riggs
Alice GLÄTTLI
Marianna Vrettou-Schultes
Wassilios Grammenos
Original Assignee
Basf Se
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Publication of WO2011069916A1 publication Critical patent/WO2011069916A1/fr

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    • 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
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • the present invention relates Triazolylmethyloxirane of formula I.
  • variables have the following meanings: A, B independently of one another are phenyl which is unsubstituted or one, two, three or four independently selected substituents L, where L is
  • L is halogen, cyano, nitro, cyanato (OCN), Ci-C4-alkyl, Ci-C 4 -Halo- genalkyl, phenyl-Ci-C4-alkyloxy, C2-C4 alkenyl, C2-C4 haloalkenyl , C2-C4 alkynyl, C2-C4 haloalkynyl, Ci-C 4 alkoxy, Ci-C4-haloalkoxy, C1-
  • a 1 is hydrogen, hydroxy, Ci-C4-alkyl, Ci-C 4 haloalkyl, amino, Ci-C 4 alkylamino or di-Ci-C 4 alkylamino,
  • a 2 A 1 wherein one of said groups or C2-C4 alkenyl, C2-C 4 - haloalkenyl, Ci-C 4 alkoxy, Ci-C4-haloalkoxy, C3-C6 cycloalkyl or C3-C6-halocycloalkyl, ;
  • a 3, A 4 are independently hydrogen, Ci-C 4 alkyl, Ci-C 4 -Halo- genalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C3-C6 cycloalkyl or C3-C6-halocycloalkyl ; where the aliphatic and / or alicyclic and / or aromatic groups of the radical definitions of L can themselves carry one, two, three or four identical or different groups R L :
  • R L is halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C 4 - alkoxy,
  • R 1 is Cs or C 5 alkyl; and their agriculturally acceptable salts.
  • the invention relates to the preparation of the compounds I, the intermediates for the preparation of the compounds I and their preparation and the use of the compounds according to the invention for controlling phytopathogenic fungi and agents containing them.
  • Triazolylmethyloxiranes having substituted triazole group e.g. from WO 96/38440, WO 97/41 107, WO 97/42178, WO 97/43269, WO 97/44331, WO 97/443332, WO 99/05149 and WO 99/21853.
  • WO 2009/077471 PCT / EP2008 / 067483
  • WO 2009/077443 PCT / EP2008 / 067394
  • WO 2009/077500 PCT / EP2008 / 067545
  • WO 2009/077497 PCT / EP2008 / 067539
  • triazolo compounds are known in which the triazole ring carries an S-methyl or S-ethyl group.
  • the fungicidal action of the compounds known from the prior art can be desired in some cases, in particular at low application rates left. It is an object of the present invention to provide novel compounds which preferably have improved properties, such as a better fungicidal action and / or better toxicological properties. Because of the general problem that fungicidal compounds often lead to resistances in practice, it is also an object to provide new alternative compounds which can be effectively used as agricultural fungicides. This object has surprisingly been achieved with the compounds of the formula I described herein.
  • 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 are hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, carbonic acid, sulfuric acid, phosphoric acid and nitric acid.
  • Suitable organic acids are, for example, formic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid and other arylcarboxylic acids, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals having 1 to 20 Carbon atoms), arylsulfonic acids or disulfonic acids (aromatic radicals such as phenyl and naphthyl which carry one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids with straight-chain or branched
  • the metal ions are, in particular, the ions of the elements of the second main group, in particular calcium and magnesium, the third and fourth main groups, in particular aluminum, tin and lead, and the first to eighth transition groups, in particular chromium, manganese, iron, cobalt, nickel, copper, Zinc and others into consideration. Particularly preferred are the metal ions of the elements of the subgroups of the fourth period.
  • the metals can be present in the various valences that belong to them.
  • the compounds of the formula I according to the invention can be prepared, for example, by the syntheses shown in the following Schemes.
  • Suitable oxidizing agents are, for example, hydrogen peroxide, if appropriate in the presence of (organic) acids such as acetic acid or trifluoroacetic acid, hydrogen peroxide-urea complexes, peroxometallates such as peroxo-toluate, peroxovanadates and peroxotungstates, oxones (potassium peroxomonosulfate), MCPBA (meta-chloroperbenzoic acid), peracetic acid , Sodium periodate or also bromine, N-bromosuccinimide, N-chlorosuccinimide or dibromohydantoin in aqueous solution.
  • organic acids such as acetic acid or trifluoroacetic acid
  • peroxometallates such as peroxo-toluate, peroxovanadates and peroxotungstates
  • oxones potassium peroxomonosulfate
  • MCPBA metal-chloroperbenzoic acid
  • peracetic acid
  • a and B are defined as herein described, or as herein preferred, by reaction with the corresponding derivative YR 1 , wherein Y is a leaving group, such as halogen (eg, Cl or Br) or OSO 2 R ', where R 'is Ci-C6-alkyl, Ci-C6-haloalkyl, aryl or substituted aryl, are prepared.
  • Y is a leaving group, such as halogen (eg, Cl or Br) or OSO 2 R ', where R 'is Ci-C6-alkyl, Ci-C6-haloalkyl, aryl or substituted aryl, are prepared.
  • Suitable conditions for alkylation reactions are known to those skilled in the art.
  • Compounds of the formula II are known from the prior art, see for example WO 96/38440, WO 97/41 107, WO 97/42178, WO 97/43269, WO 97/44331, WO 97/443332, WO 99/05149 and WO 99/21853, WO 2009/077471 (PCT / EP2008 / 067483), WO 2009/077443 (PCT / EP2008 / 067394) WO 2009/077500 (PCT / EP2008 / 067545).
  • the synthesis of the compounds of the formula II can be carried out in accordance with the cited prior art.
  • a and B are defined as described herein by reaction with a strong base and sulfur powder.
  • 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 (TM EDA).
  • 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, optionally in the presence of an organic or inorganic acid, e.g. Acetic acid, dilute sulfuric acid or dilute hydrochloric acid. The reaction temperature is preferably between -70 ° C and + 20 ° C, in particular between -70 ° C and 0 ° C. The reaction is generally carried out under normal pressure.
  • 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
  • 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.
  • the reaction mixture is extracted with a suitable organic solvent and the residue is optionally purified by recrystallization and / or chromatography.
  • Another possibility, starting from compounds III compounds II is to prepare compounds III with sulfur in the presence of an aprotic, polar solvent such as an amide (such as dimethylformamide (DMF)) or N-alkylpyrrolidone (such as N-octylpyrrolidone, N-dodecylpyrrolidone or N-methylpyrrolidone (NMP)) implement.
  • an aprotic, polar solvent such as an amide (such as dimethylformamide (DMF)) or N-alkylpyrrolidone (such as N-octylpyrrolidone, N-dodecylpyrrolidone or N-methylpyrrolidone (NMP)) implement.
  • an aprotic, polar solvent such as an amide (such as dimethylformamide (DMF)) or N-alkylpyrrolidone (such as N-octylpyrrolidone, N-dodecylpyrrolidone
  • Z is a leaving group Y (see below) or OH and A and B are as defined herein, represent important starting compounds.
  • Z is a leaving group Y, such as, for example, halogen (eg Cl or Br) or OSO 2 R ', where R' is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, aryl or substituted aryl.
  • OSO 2 R ' is a mesylate, triflate, phenyl or toluenesulfonate group.
  • compounds of the formula IV are reacted with 1, 2,4-triazole and a base such as, for example, sodium hydride in, for example, DMF. See also eg EP 0 421 125 A2.
  • Z is a leaving group Y (see above) and A and B are as defined or preferably defined for formula I.
  • Suitable epoxidation processes are known to the person skilled in the art. For example, hydrogen peroxide / maleic anhydride can be used for this purpose.
  • the double bond may be in both (E) and (Z) configurations. This is represented by the jagged bond between B and the double bond.
  • Compounds V can be obtained from compounds VI
  • VI by reacting compounds VI with, for example, acetic acid / h SC in a suitable organic solvent such as an ether such as Et20 or dioxane to form the double bond. Suitable methods are known to the person skilled in the art.
  • Z is as defined for formula V and A and B are as defined for formula I.
  • 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 preferred to react in the presence of an additive such as e.g. Tetramethylethylenediamine (TMEDA) to perform.
  • TEDA Tetramethylethylenediamine
  • the disulfides are commercially available or synthesized by known manufacturing methods.
  • 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.
  • the reaction temperature is preferably between -70 ° C and + 20 ° C, in particular between -70 ° C and 0 ° C.
  • the reaction is generally carried out under normal pressure.
  • 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.
  • the reaction mixture is extracted with a suitable organic solvent and the residue is optionally purified by recrystallization and / or chromatography.
  • An advantage of the synthesis of the compounds I using disulfides (VIII) is that in the reaction in addition to the desired product I, the sulfide R 1 R 2 R 3 C-SH (IX) is formed and this by oxidation with a suitable Oxidatinsstoff in a organic solvent can be converted back into the disulfide (VIII).
  • Suitable oxidizing agents for this purpose are, for example, H 2 O 2, air, O 2, I 2, NaOCl, NaOBr, NaBrO 3, tert-butyl hydroperoxide and the like.
  • the person skilled in suitable reactions for the conversion of a sulfide into the disulfide and corresponding reaction conditions are known.
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl and the alkyl moieties of composite groups such as Alkylamino: saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, 6, 8 or 12 carbon atoms, for example C 1 -C 6 -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methyl- butyl butyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,
  • 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-bromethyl, 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-trifluoroprop
  • alkenyl groups such as (C 2 -C 4) alkenyl
  • larger alkenyl groups such as (C 5 -C 8) alkenyl.
  • alkenyl groups are e.g.
  • C2-C6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1 - Methyl 2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 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-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3 butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-prop
  • 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
  • Haloalkynyl alkynyl, 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;
  • 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, e.g. C3-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;
  • Cycloalkenyl monocyclic, monounsaturated hydrocarbon groups having preferably 3 to 8 or 4 to 6, in particular 5 to 6 carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, Cyclohexene-4-yl and the like;
  • Halocycloalkenyl cycloalkenyl 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 for are OCH 2 F, OCHF 2, OCF 3, OCH 2 Cl, OCHC, OCCl 3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy , 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC 2 F 5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2 Difluoropropoxy, 2,3
  • novel compounds of this invention contain chiral centers and are generally obtained in the form of racemates or as diastereomeric mixtures of erythro and threo forms.
  • the erythro and threo diastereomers can be separated in the compounds of the invention, for example, due to their different solubility or by column chromatography and isolated in pure form. From such uniform pairs of diastereomers can be obtained by known methods uniform enantiomers.
  • antimicrobial agents it is possible to use both the uniform diastereomers or enantiomers and also their mixtures obtained in the synthesis. The same applies to the fungicides.
  • the invention therefore relates both to the pure enantiomers or diastereomers and to mixtures thereof.
  • Suitable compounds according to the invention also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.
  • the compounds of the invention may be present in various crystal modifications whose biological activity may be different. These are included in the scope of the present invention.
  • the following meanings of the substituents, in each case alone or in combination, are particularly preferred.
  • A is phenyl which is unsubstituted or contains one, two, three or four independently selected substituents L, wherein L is as herein defined or preferably defined.
  • A is unsubstituted phenyl.
  • A represents phenyl containing one, two, three, or four, especially one or two, independently selected substituents L, wherein L is as defined herein or preferred.
  • one of the substituents is in the 4-position of the phenyl ring.
  • each L is independently selected from F, Cl, Br, nitro, phenyl, phenoxy, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, difluoromethyl, difluorochloromethyl, trifluoromethoxy, Difluoromethoxy and trifluorochloromethyl.
  • L is in each case independently selected from F, Cl and Br, in particular F and Cl.
  • A is monosubstituted phenyl containing a substituent L, wherein L is as defined herein or preferably defined. According to one embodiment of this embodiment, the substituent is in the para position.
  • A is 3-fluorophenyl.
  • A is phenyl which contains two or three independently selected substituents L.
  • A is phenyl substituted with an F and containing another substituent L, wherein the phenyl may additionally contain one or two independently selected substituents L.
  • A is according to a preferred embodiment for a group A-1
  • # represents the point of attachment of the phenyl ring to the oxirane ring
  • L 2 is selected from F, Cl, NO 2 , phenyl, halophenyl, phenoxy, halophenyl, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy and C 1 -C 4 -haloalkylthio ;
  • L 3 is independently selected from F, Cl, Br, NO 2, phenyl, halophenyl, phenoxy,
  • Halophenoxy C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy
  • n 0, 1 or 2.
  • L 2 is selected according to a specific embodiment from F, Cl, methyl, methoxy, CF 3, CHF 2, OCF 3, OCF 3 and OCHF 2. According to a more specific embodiment, L 2 is F or Cl. L 3 is independently selected from F, Cl, methyl, methoxy, CF 3, CHF 2, OCF 3, OCF 3 or OCHF 2 according to a specific embodiment. According to an even more specific embodiment, L 3 is independently F or Cl.
  • the fluoro substituent is in the 4-position according to a preferred embodiment.
  • A is disubstituted phenyl containing exactly two independently selected substituents L, wherein L is as herein defined or preferably defined.
  • L is each independently preferably selected from F, Cl, Br, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl and C 1 -C 4 -alkoxy, in particular selected from F, Cl, C 1 -C 4 -alkyl, C 1 -C 4 Haloalkyl and C 1 -C 4 alkoxy, especially selected from F, Cl, methyl, trifluoromethyl and methoxy.
  • the second Substituenet L is selected from methyl, methoxy and chlorine.
  • one of the substituents is in the 4-position of the phenyl ring.
  • A is phenyl which contains an F and exactly one further substituent L as defined herein or preferably defined.
  • the phenyl ring A is disubstituted in the 2,4-position. According to yet another specific embodiment, the phenyl ring A is disubstituted in the 2,3-position. According to yet another specific embodiment, the phenyl ring A is disubstituted in the 2,5-position. According to yet another specific embodiment, the phenyl ring A is disubstituted in the 2,6-position. According to yet another specific embodiment, the phenyl ring A is disubstituted in the 3,4-position. According to yet another specific embodiment, the phenyl ring A is disubstituted in the 3,5-position.
  • A is phenyl which is substituted by exactly two F.
  • A is 2,3-difluoro substituted.
  • A is 2,4-difluoro-substituted.
  • A 2,5-difluoro-substituted.
  • A is 2,6-difluoro-substituted.
  • A is 3,4-difluoro-substituted.
  • a 3, 5 is difluoro-substituted.
  • A is trisubstituted phenyl containing three independently selected substituents L, wherein L is as herein is defined or preferably defined.
  • A is phenyl which is substituted by exactly three F.
  • A is 2,3,4-trisubstituted, in particular 2,3,4-trifluoro-substituted.
  • A is 2,3,5-trisubstituted, in particular 2,3,5-trifluoro-substituted.
  • A is 2,3,6-trisubstituted, in particular 2,3,6-trifluoro-substituted.
  • A is 2,4,6-trisubstituted, in particular 2,4,6-trifluoro-substituted.
  • A is 3,4,5-trisubstituted, in particular 3,4,5-trifluoro-substituted.
  • A is 2,4,5-trifluoro-substituted, in particular 2,4,5-trifluoro-substituted.
  • B is phenyl which is unsubstituted or contains one, two, three or four identical or different substituents L, where L is as herein defined or preferably defined.
  • B is unsubstituted phenyl.
  • B represents phenyl containing one, two, three, or four independently selected substituents L, wherein L is as herein defined or preferably defined.
  • B represents phenyl which contains one, two or three, preferably one or two, independently selected substituents L as defined or preferred herein.
  • each L is independently selected from F, Cl, Br, methyl, methoxy and trifluoromethyl.
  • B is phenyl which is substituted by one, two or three, preferably one or two, halogen atoms.
  • B denotes phenyl which contains one, two, three or four substituents L, where L is independently selected from F, Cl, Br, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, Trichloromethyl, difluoromethyl, difluorochloromethyl, trifluoromethoxy, difluoromethoxy and trifluorochloromethyl.
  • L is each independently selected from F, Cl and Br.
  • B is phenyl which is unsubstituted or substituted by one, two or three substituents independently selected from halogen, NO 2 , amino, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 4 haloalkyl, Ci-C 4 - haloalkoxy, Ci-C 4 alkylamino, Ci-C 4 dialkylamino, thio, and Ci-C 4 alkylthio.
  • the phenyl ring in B is monosubstituted with exactly one substituent L, wherein L according to a special embodiment This embodiment is in ortho position to the point of attachment of the phenyl ring with the oxirane ring.
  • L is defined as herin or preferably defined.
  • B is monosubstituted phenyl by Cl, in particular 2-chlorophenyl.
  • B represents phenyl containing two or three, especially two, independently selected substituents L, wherein L is as herein defined or preferably defined.
  • B is a phenyl ring which contains a substituent L in the ortho position and also has exactly one further independently selected substituent L.
  • the phenyl ring is 2,3-disubstituted.
  • the phenyl ring is 2,4-disubstituted.
  • the phenyl ring is 2,5-disubstituted.
  • the phenyl ring is 2,6-disubstituted.
  • B is a phenyl ring which contains a substituent L in the ortho position and also contains exactly two further independently selected substituents L.
  • the phenyl ring is 2,3,5-trisubstituted.
  • the phenyl ring is 2,3,4-trisubstituted.
  • the phenyl ring is 2,4,5-trisubstituted.
  • B is phenyl which contains a substituent L in the 2-position and one, two or three further independently selected substituents L.
  • B is according to a preferred embodiment for a
  • # represents the point of attachment of the phenyl ring to the oxirane ring
  • L 1 is selected from halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy and C 1 -C 4 -haloalkylthio, preferably selected from F, Cl, methyl, ethyl, methoxy, ethoxy, CF 3, CHF 2, OCF 3, OCHF 2 and SCF 3;
  • L 2 is selected from halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy and C 1 -C 4 -haloalkylthio, preferably selected from F,
  • L 3 is independently selected from halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy and C 1 -C 4 -haloalkylthio, preferably selects from F, Cl, methyl, ethyl, methoxy, ethoxy, CF 3 , CHF 2 , OCF 3 , OCHF 2 and SCF 3 ; and
  • L 1 is F.
  • L 1 is Cl.
  • L 1 is methyl.
  • L 1 is methoxy.
  • L 1 represents CF 3 .
  • L 1 is OCF 3 or OCHF 2.
  • B is phenyl which in the 2-position is a substituent selected from F, Cl, CH 3 , OCH 3 , CF 3 , CHF 2 , OCF 3 and OCHF 2 , and one or two further independently selected substituents L.
  • L 2 is F.
  • L 2 is Cl. According to a further preferred embodiment, L 2 is methyl. According to yet another preferred embodiment, L 2 is methoxy. In yet another preferred embodiment, L 2 is CF 3 . According to yet another preferred embodiment, L 2 is OCF 3 or OCHF 2 .
  • L 3 is F. According to another preferred embodiment, L 3 is Cl. According to a further preferred embodiment, L 3 is methyl. In yet another preferred embodiment, L 3 is methoxy. In yet another preferred embodiment, L 3 is CF 3 . According to yet another preferred embodiment, L 3 is OCF 3 or OCHF 2 .
  • B thus represents a disubstituted phenyl ring B-1.
  • B is a 2,3-disubstituted phenyl ring.
  • the phenyl ring B-1 is 2,4-disubstituted.
  • the phenyl ring B-1 is 2,5-disubstituted.
  • the phenyl ring is 2,6-disubstituted.
  • the phenyl ring B-1 is 2,3,5-trisubstituted.
  • the phenyl ring B-1 is 2,3,4-trisubstituted.
  • the phenyl ring B is 2,4,5-trisubstituted.
  • L is independently halogen, cyano, nitro, cyanato (OCN), C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, phenyl-C 1 -C 4 -alkyloxy, C 2 -C 4 -alkenyl, C 2 -C 4 -halogenoalkenyl , C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylcarbonyloxy, C 1 -C 4 -alkylsulfonyloxy, C 2 -C 4 -alkenyloxy, C 2 -C 4 -haloalkenyl-oxy , C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6
  • a 2 is one of the groups mentioned under A 1 or C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl or C 3 -C 6 -halocycloalkyl,
  • a 3 , A 4 are each independently hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 3 -C 6 -cycloalkyl or C 3 -C 6 -halocycloalkyl; in which the aliphatic and / or alicyclic and / or aromatic groups of the radical definitions of L can themselves carry one, two, three or four identical or different groups R L : R L is halogen, cyano, nitro, C 1 -C 4 -alkyl, ci C 4 -haloalkyl, C 1 -C 4 -alkoxy, ci
  • a 1 is hydrogen, hydroxy, Ci-C4-alkyl, Ci-C4-haloalkyl;
  • a 2 is one of the groups mentioned under A 1 or C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl;
  • a 3 , A 4 are independently hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl; where the aliphatic and / or alicyclic groups of the radical definitions of L can themselves carry one, two, three or four identical or different groups R L :
  • R L is halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4 alkoxy, Ci-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, amino, C C 4 alkylamino, di-C 1 -C 4 alkylamino.
  • L is independently selected from halogen, NO2, amino, C1-C4 alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4 alkylamino, di- Ci C 4 alkylamino, thio and C 1 -C 4 alkylthio.
  • L is independently selected from halogen, Ci-C4 alkyl, C1-C4 haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 haloalkoxy and Ci-C4-haloalkylthio, in particular halogen, Ci-C 4 Alkyl and C 1 -C 4 -haloalkyl.
  • L is independently selected from F, Cl, Br, CH 3, C 2 H 5, iC 3 H 7, tC 4 H 9, OCH 3, OC 2 H 5, CF 3, CCl 3, CHF 2 , CCIF 2 , OCF 3 , OCHF 2 and SCF 3 , in particular selected from F, Cl, CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , CF 3 , CHF 2 , OCF 3 , OCHF 2 and SCF 3 .
  • L is independently selected from F, Cl, CH3, OCH3, CF3, OCF3 and OCHF2. It may be preferred that L is independently F or Cl.
  • Trifluoromethoxyphenyl and B is 2-chlorophenyl.
  • A is 4-fluorophenyl and B is 2-chlorophenyl.
  • A is 2,4-difluorophenyl and B is 2-chlorophenyl.
  • A is 4-fluorophenyl and B is in each case 2-difluoromethoxyphenyl.
  • the compounds IA are phenyl, 4-chlorophenyl, 2,4-chlorophenyl, 2-chlorophenyl, 2-fluorophenyl, 4-methylphenyl, 4-fluorophenyl, 3-bromo-4-fluorophenyl, 4- Bromophenyl, 3,4-dichlorophenyl, 4-tert-butylphenyl, 3-chlorophenyl, 3,5-dichlorophenyl or 4-trifluoromethoxyphenyl and B is each 2-fluorophenyl.
  • phenyl 4-chlorophenyl, 2,4-chlorophenyl, 2-chlorophenyl, 2-fluorophenyl, 4-methylphenyl, 4-fluorophenyl, 3-bromo-4-fluorophenyl, 4 - Bromphenyl, 3,4-dichlorophenyl, 4-tert-butylphenyl, 3-chlorophenyl, 3,5-dichlorophenyl or 4-trifluoromethoxyphenyl and B is 2-bromophenyl.
  • R 1 is C3 or Cs-alkyl
  • R 1 is CH (CH 3 ) 2 or CH 2 CH 2 CH 2 , especially CH (CH 3 ) 2 .
  • R 1 is Cs-alkyl, ie for
  • R is preferably CH 2 CH 2 CH 2 CH 3, CH (CH 3) CH 2 CH 2 CH 3, CH 2 CH 2 CH (CH 3) 2, CH (CH 3) CH ( CH 3 ) 2 , C (CH 3 ) 2 CH 2 CH 3 or CH 2 C (CH 3 ) 3 .
  • R is preferably CH 2 CH 2 CH 2 CH 3 CH (CH 3) CH 2 CH 2 CH 3, CH 2 CH 2 CH (CH 3) 2,
  • R 1 is preferably
  • R 1 is CH 2 R 2 and R 2 is n-butyl, sec-butyl, isobutyl or tert-butyl.
  • the compounds according to the invention can be used as pure enantiomers or as
  • Enantiomeric ratio are present. According to one embodiment is a
  • Both "trans” isomers are also 5-n-propylsulfanyl-1 - [[rel- (2S, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl ] -1, 2,4-triazole (or 5-n-propylsulfanyl-1 - [[- rel- (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane] 2-yl] methyl] -1, 2,4-triazole)
  • Stereoisomers of compound I.3 (p 0) in which A is 4-fluorophenyl, B is 2-chlorophenyl and R 1 is n-pentyl): isomer l.3-a1): 5-n-pentylsulfanyl-1 - [[(2S, 3S) -3- (2-chlorophenyl) -2- (2-fluorophenyl) oxirane
  • Both "trans” isomers are also 5-n-pentylsulfanyl-1 - [[rel- (2S, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] - 1,2,4-triazole (or 5-n-pentylsulfanyl-1 - [[- rel- (2R, 3S) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] - 1, 2,4-triazole)
  • Both “cis” isomers are also 5-n-propylsulfanyl-1 - [[rel- (2S, 3S) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] - 1,2,4-triazole (or 5-n-propylsulfanyl-1 - [[rel- (2R, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl ] -1, 2,4-triazole)
  • Both "trans” isomers are also 5-n-propylsulfanyl-1 - [[rel- (2S, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] - 1,2,4-triazole (or 5-n-propylsulfanyl-1 - [[- rel- (2R, 3S) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] - 1, 2,4-triazole)
  • Both "cis” isomers are also 5-n-pentylsulfanyl-1 - [[rel- (2S, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl ] -1, 2,4-triazole (or 5-n-pentylsulfanyl-1 - [[rel- (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane-2 -yl] methyl] -1, 2,4-triazole)
  • Both "trans” isomers are also 5-iso-propylsulfanyl-1 - [[rel- (2S, 3R) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] - 1,2,4-triazole (or 5-iso-propylsulfanyl-1 - [[- rel- (2R, 3S) -3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-yl] methyl] - 1, 2,4-triazole).
  • R 1 corresponds in each case to one row of Table A (compounds 1-1 .63aA-1 to I-
  • A-240 4-chlorophenyl CH (CH 3 ) CH 2 CH 2 CH 3
  • A-243 4-fluorophenyl CH (CH 3 ) CH 2 CH 2 CH 3
  • connection names for the individual connections are derived as follows: eg. is the "compound / -l3aA-10" (tags added) the compound of the formula wherein A is 2,5-difluorophenyl (as indicated in Table 3a) and B is 4-methylphenyl and R 1 is CH (CH 3) 2 (as indicated in line 10 of Table A).
  • the compounds of the formula I or the compositions according to the invention 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 partially systemically effective and can be used in crop protection 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.
  • the compounds I and the compositions according to the invention for combating a multiplicity of pathogenic fungi on various crop plants, 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
  • 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; Sweet herb (Stevia rebaudania); 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.
  • the compounds I or the inventive composition Compositions for combating a variety of fungal pathogens in crops eg. Potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugarcane; 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 compounds I or the compositions according to the invention is used for combating 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 have been modified by breeding, mutagenesis or genetic engineering, including biotechnological agricultural products currently on the market or under development (see for example http://www.bio.org/speeches/pubs/er/agri_products .asp).
  • Genetically engineered plants are plants whose genetic material has been altered in a manner that does not occur under natural conditions by crossing, mutations or natural recombination (i.e., rearrangement of genetic information). As a rule, one or more genes are integrated into the genome of the plant in order to improve the properties of the plant.
  • Such genetic engineering also includes post-translational modifications of proteins, oligo- or polypeptides, e.g. by glycolylation or binding of polymers such as e.g. prenylated, acetylated or farnelysierter residues or PEG residues.
  • plants may be mentioned which, by means of breeding and genetic engineering measures, tolerate certain types of herbicides, such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as, for example, As sulfonylureas (EP-A 257 993, US 5,013,659) or imidazolinones (eg.
  • herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as, for example, As sulfonylureas (EP-A 257 993, US 5,013,659) or imidazolinones (eg.
  • EPSPS Enolpyruvylshikimat-3-phosphate synthase
  • Glyphosate see, for example, WO 92/00377
  • glutamine synthetase (GS) inhibitors such as. Glufosinate (see eg EP-A 242 236, EP-A 242 246) or oxynil herbicides (see eg US 5,559,024).
  • Crop plants such as soybean, cotton, maize, beets and oilseed rape produced, which are resistant to glyphosate or glufosinate, produced under the trade names RoudupReady ® (glyphosate-resistant, Monsanto, USA) and Liberty Link ® (glufosinate-resistant , Bayer CropScience, Germany).
  • toxins eg. B. those from the bacterial strain Bacillus produce.
  • Toxins produced by such genetically engineered plants include e.g. B. Insecticidal proteins of Bacillus spp., In particular of B. thuringiensis, such as the endotoxins CrylAb, CrylAc, Cryl F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs), e.g. Eg VIP1,
  • VIP2, VIP3, or VIP3A Insecticidal proteins of nematode-colonizing bacteria, e.g. B. Photorhabdus spp. or Xenorhabdus spp .; Toxins from animal organisms, eg. B. Wepsen, spider or scorpion toxins; fungal toxins, e.g. Eg from Streptomyces; 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
  • Steroid metabolizing enzymes e.g. 3-hydroxy steroid oxidase, ecdysteroid IDP glycosyltransferase, cholesterol oxidase, ecdysone inhibitors, or HMG-CoA reductase
  • ion channel blocker
  • toxins can also be produced in the plants as proteoxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a novel combination of different protein domains (see, for example, WO 2002/015701).
  • Further examples of such toxins or genetically modified plants which produce these toxins are described in EP-A 374 753, WO 93/07278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 and WO 03/52073 discloses.
  • the methods for producing these genetically modified plants are known in the art and z. B. in the publications mentioned above. Numerous of the aforementioned toxins confer on the plants that produce them tolerance to pests of all taxonomic arthropod classes, in particular to beetles (Coeleropta), diptera (Diptera) and
  • 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 varieties which toxin is
  • Agrisure ® CB and Bt176 from Syngenta Seeds SAS, France corn varieties which the toxin CrylAb and the PAT Produce enzyme
  • MIR604 from Syngenta Seeds SAS, France maize varieties that produce a modified version of the toxin Cry3A, see WO 03/018810)
  • MON 863 from Monsanto Europe SA, Belgium maize varieties that produce the toxin Cry3Bb1
  • IPC 531 from Monsanto Europe SA, Belgium
  • cotton varieties that produce a modified version of the toxin CrylAc 1507 from Pioneer Overseas Corporation, Belgium (maize varieties that produce the Toxin Cry1 F and the PAT enzyme).
  • plants which produce by genetic engineering measures one or more proteins that cause increased resistance or resistance to bacterial, viral or fungal pathogens, such as.
  • proteins that cause increased resistance or resistance to bacterial, viral or fungal pathogens
  • pathogenesis-related proteins PR proteins, see EP-A 0 392 225
  • resistance proteins for example potato varieties which produce two resistance genes against Phytophthora infestans from the Mexican wild potato Solanum bulbocastanum
  • T4 lyso - zym eg, potato varieties that are resistant to bacteria such as Erwinia amylvora due to the production of this protein.
  • plants are included whose productivity has been improved by genetic engineering methods by z.
  • 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 may be increased.
  • plants are also included whose ingredients have been modified, in particular to improve human or animal nutrition, with the aid of genetic engineering methods.
  • As oil plants producing health long-chain omega-3 fatty acids or monounsaturated omega-9 fatty acids eg Nexera ® - rape, DOW Agro Sciences, Canada.) Produce.
  • plants are included, which have been modified for the improved production of raw materials by means of genetic engineering methods by z.
  • the compounds I or the compositions according to the invention are suitable for controlling the following plant diseases:
  • Albugo spp. White rust on ornamental plants, vegetable crops (eg A. Candida) and sunflowers (eg BA tragopogonis); Alternaria spp. (Blackness, black spotiness) on vegetables, oilseed rape (for example BA brassicola or A brassicae), sugar beet (for example BA tenuis), fruit, rice, soya beans and on potatoes (eg BA solani or A. alternata) and tomatoes (eg. BA solani or A. alternata) and Alternaria spp. (Earwires) on wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, eg.
  • Botrytis cinerea Botryotina fuckeliana: gray mold, gray mold) on berry and pome fruit (including strawberries), vegetables (including lettuce, carrots, celery and cabbage), oilseed rape, flowers, vines, forestry crops and wheat (ear fungus); Bremia lactucae (downy mildew) on salad; Ceratocystis (Syn. Ophiostoma) spp. (Bläuepilz) on deciduous and coniferous trees, z.
  • Botrytis cinerea Triomorph: Botryotina fuckeliana: gray mold, gray mold) on berry and pome fruit (including strawberries), vegetables (including lettuce, carrots, celery and cabbage), oilseed rape, flowers, vines, forestry crops and wheat (ear fungus); Bremia lactucae (downy mildew) on salad; Ceratocystis (Syn. Ophiostoma) spp. (Bläuepilz)
  • BC ulmi elm dying, Dutch elm disease
  • Cercospora spp. Cercospora leaf spot
  • maize eg BC zeae-maydis
  • sugar beets eg BC beticola
  • sugarcane vegetables
  • coffee soybeans
  • soybeans eg BC sojina or C. kikuchii
  • Cladosporium spp. on tomato eg BC fulvum: velvet spot disease
  • cereals eg.
  • BC herbarum (earwax) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (Anamorph: Helminthosporium or Bipolaris) spp. (Leaf spot) on maize (for example BC carbonum), cereals (for example B. sativus, anamorph: B. sorokinia-na: brown spot) and rice (for example BC miyabeanus, anamorph: H. oryzae); 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 (£ betae), vegetables (eg BE pisi), such as cucumber (for example BE cichoracearum) and cabbage plants, such as rapeseed (for example, B. cruciferarum); Eutypa lata (Eutypa crab or extinction, anamorphic Cytosporina lata, Syn. Libertella blepharis) on fruit trees, vines and many ornamental shrubs; Exserohilum (Syn.
  • Helminthosporium) spp. on maize eg BE turcicum
  • Fusarium (Teleomorph: Gibberella) spp. Wang, root and stem rot
  • BF graminearum or F. culmorum root rot and Tauboder whiteness
  • F. culmorum root rot and Tauboder whiteness
  • F. oxysporum on tomatoes
  • F. solani on soybeans
  • F. verticillioides on maize
  • Gaeumannomyces graminis Blackleg
  • cereals eg wheat or barley
  • maize Gibberella spp.
  • cereals eg BG zeae
  • rice eg BG fujikuror, Bakanae disease
  • Gloinstaining complex of rice Guignardia bidwellii (black rot) on grapevine
  • Helminthosporium spp. Syn. Drechslera, Tele
  • BH vastatrix (coffee leaf rust) of coffee; Isariopsis clavispora (Syn. Cladosporium vitis) on grapevine; Macrophomina phasolina (Syn. Phaseoli) (root / stem rot) on soybeans and cotton; Microsium (Syn. Fusarium) nivale (snow mold) on cereals (eg wheat or
  • Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., Z. M. laxa, M. fructicola and M. fructigena (flower and lace drought) on stone fruits and other pinks; Mycosphaerella spp. on cereals, bananas, berry fruits and peanuts, such as. M. graminicola (anamorph: Septoria tritici, Septoria leaf drought) on wheat or M. fijiensis (black sigatoka disease) on bananas; Peronospora spp. (Downy mildew) on cabbage (eg BP brassicae), oilseed rape (for example P.
  • viticola black spot disease
  • soybeans eg stalk rot: P. phaseoli, Teleomorph: Diaporthe phaseolorum
  • Physoderma maydis brown spot
  • Phytophthora spp. Wild, root, leaf, stem and fruit rot
  • peppers and cucurbits eg BP capsici
  • soybeans eg BP megasperma, Syn. P. sojae
  • potatoes and tomatoes eg. BP infestans: herbaceous and brown rot
  • deciduous trees for example, P.
  • Plasmodiophora brassicae cabbage hernia
  • Plasmopara spp. E.g. B. P. viticola (vine peronospora, downy mildew) on vines and P. halstedii on sunflowers
  • Podosphaera spp. Pandery mildew of rosaceae, hops, kernels and berries, eg. B. P. leucotricha to apple
  • Polymyxa spp. Z.
  • To cereals such as barley and wheat (P. graminis) and sugar beet (P.
  • Pseudocercosporella herpotrichoides straw break, teleomorph: Tapesia yallundae
  • Pseudoperonospora downy mildew
  • Pseudo-pezicula tracheiphila red burner, anamorph: Phialophora
  • Puccinia spp. Rust disease
  • Asparagus eg BP asparagi
  • Pyrenophora anamorph: Drechslera
  • tritici-repentis leaf drought
  • P. teres net stains
  • Pyricularia spp. E.g. BP ory zae (teleomorph: Magnaporthe grisea, rice leaf brandy) on rice and P. grisea on lawn and cereals
  • Pythium spp. Tronip disease
  • turf rice, corn, wheat, cotton, oilseed rape, sunflower, sugar beets, vegetables and other plants
  • Ramularia spp. Z.
  • BR collo-cygni (speckled disease / sunburn complex / Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, oilseed rape, potatoes, sugar beets, vegetables and various other plants, eg. BR solani (root / stem rot) on soybeans, R. solani (leaf-sheathing) on rice or R.
  • cerealis pointed eye-spot on wheat or barley; Rhizopus stolonifer (soft rot) on strawberries, carrots, cabbage, grapevine and tomato; Rhynchosporium secalis (leaf spot) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (Stem or white rot) 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 spice tan) on cereals; Uncinula (Syn. Erysiphe) necator (powdery mildew, anamorphic: Oidium tuckeri) on grapevine; Sexspaeria spp. (Leaf spot) on corn (for example, S. turcicum, Syn. Helminthosporium turcicum) and turf; Sphacelotheca spp.
  • BT deformans curling disease
  • T. pruni pocket disease
  • Thielaviopsis spp. Black root rot
  • tobacco, pome fruit, vegetable crops, soybeans and cotton eg. BT basicola (Syn: Chalara elegans); Tilletia spp. (Stone or Stinkbrand) of cereals, such.
  • BT tritici Syn. T. caries, Weizensteinbrand
  • T. controversa Zwergsteinbrand
  • Typhula incarnata snow rot
  • 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 wilt) on various plants, such as fruit and ornamental trees, vines, soft fruit, vegetables and crops, such. BV dahliae on strawberries, rapeseed, potatoes and tomatoes.
  • the compounds I and the 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.
  • adhesives, glues, wood, paper and cardboard, textiles, leather, color dispersions, plastic, cooling lubricant medium, fibers and tissues against 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., Altemaria spp., Paecilomyces spp. and Zygomycetes such as / Wu corp spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.
  • the compounds of the formula I can be present in various crystal modifications whose biological activity can be different. These are included in the scope of the present invention.
  • the compounds I and the compositions according to the invention are suitable for increasing plant health. Moreover, 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 compounds I are used as such or in the form of a composition by the harmful fungi, their habitat or the plants to be protected against fungal attack, plant propagation materials, eg. As seeds, the soil, surfaces, materials or spaces treated with a fungicidally effective amount of the compounds I.
  • plant propagation materials eg. As seeds, the soil, surfaces, materials or spaces treated with a fungicidally effective amount of the compounds I.
  • the application may be both before and after the infection of the plants, plant propagation materials, eg. As seeds, the soil, the surfaces, materials or spaces made by the fungi.
  • Plant propagating materials may be treated preventively together with or even before sowing or together with or even before transplanting with compounds I as such or with a composition containing at least one compound I.
  • the invention relates to agrochemical compositions containing a solvent or solid carrier and at least one compound I and their use for controlling harmful fungi.
  • An agrochemical composition contains a fungicidally effective amount of a compound I.
  • the term "effective amount" means an amount of the agrochemical composition or compound I which is sufficient to control harmful fungi on crop plants or in material and building protection and not to a considerable extent Such an amount may vary within a wide range and is influenced by numerous factors such as the fungus to be controlled, the particular crop or material being treated, the climatic conditions and compounds.
  • the compounds I, their N-oxides and their salts can be converted into the types customary for agrochemical compositions, e.g. 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 compound 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 either be soluble (soluble) or dispersible (wettable) in water, as well as 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 Engineers Handbook, 4th ed., McGraw-Hill, New York, 1963, 8-57 and et seq., WO 91/13546,
  • the agrochemical compositions can furthermore also contain auxiliaries customary for crop protection agents, the choice of auxiliaries being based on the specific application form or the active substance.
  • auxiliaries are solvents, solid carriers, surface-active substances (such as further solubilizers, protective colloids, wetting agents and adhesives), organic and inorganic thickeners, bactericides, antifreeze agents, defoamers, if appropriate dyes and adhesives (for example for seed treatment).
  • Suitable solvents include water, organic solvents such as mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg paraffins, tetrahydronaphthalene, alkylated naphtha 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 strongly polar solvents, for example amines such as N-methylpyrrolidone, into consideration.
  • organic solvents such as mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cycl
  • Solid carriers are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour
  • alkali alkaline earth
  • ammonium salts of aromatic sulfonic acids eg. B. of lignin (Borresperse ® grades, Borregaard, Norway), phenol, naphtha lin (Morwet ® types, Akzo Nobel, USA) and dibutyl (nekal ® - types, BASF, Germany), and of fatty acids , Alkyl and alkylaryl sulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of na
  • thickeners ie, compounds that give the composition a modified flow properties, ie high viscosity at rest and low viscosity in motion
  • thickeners are polysaccharides and organic and inorganic sheet minerals, such as xanthan gum (Kelzan ®, CP Kelco, U.S.A.), Rhodopol ® 23 (Rhodia, France) or Veegum ® (RT Vanderbilt, USA) or attaclay ® (Engelhard Corp., NJ, USA).
  • Bactericides may be added to stabilize the composition.
  • bactericides are those based on dichlorophen and benzyl alcohol hemiformal (Proxel ®.. Of Messrs. ICI or Acetide ® RS from Thor Chemie and Kathon ® MK from Rohm & Haas) and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acetide ® MBS Fa. Thor Chemie).
  • Suitable antifreeze agents are ethylene glycol, propylene glycol, urea fabric 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 Dyes and pigments.
  • adhesives examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and cellulose ethers (Tylose ®, Shin-Etsu, Japan).
  • emulsions, pastes or oil dispersions come mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water into consideration.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthal
  • Powders, dispersants and dusts can be prepared by mixing or jointly grinding the compounds I and, where present, further active compounds with at least one solid carrier.
  • Granules for. As coated, impregnated and homogeneous granules can be prepared by binding the active 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 cereal flour, bark, wood and nutshell flour, cellulose powders and other solid carriers.
  • composition types are:
  • composition 15 parts by weight of the active compounds are dissolved in 75 parts by weight of xylene with the addition of Ca dodecylbenzenesulfonate and castor oil (in each case 5 parts by weight). Dilution in water results in an emulsion.
  • the composition has 15% by weight active ingredient content.
  • Emulsions (EW, EO, ES)
  • the active compounds 25 parts by weight of the active compounds are dissolved in 35 parts by weight of xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • This mixture is added by means of an emulsifying machine (eg 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 .-%.
  • the active ingredients 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.
  • the active compounds are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and prepared by means of industrial equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the composition has an active substance content of 50% by weight. vii) Water-dispersible and water-soluble powders (WP, SP, SS, WS)
  • the active ingredients 75 parts by weight of the active ingredients are ground with the addition of 25 parts by weight of dispersing and wetting agents and silica gel in a rotor-Strator mill. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the composition is 75% by weight.
  • composition types for direct application 20 parts by weight of the active ingredients, 10 parts by weight of dispersant, 1 part by weight of swelling agent ("gelling agent”) and 70 parts by weight of water or an organic solvent are ground to a fine suspension Dilution with water results in a stable suspension with 20% by weight of active substance content 2.
  • Granules 0.5 part by weight of the active ingredients are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content.
  • compositions of the compounds 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.
  • the compounds are preferably present in a purity of from 90% to 100%, preferably 95% used up to 100%.
  • 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
  • These compositions can be applied to the propagating materials, in particular seeds, undiluted or, preferably, diluted.
  • the corresponding composition can be diluted 2 to 10 times, so that 0.01 to 60% by weight, preferably 0.1 to 40% by weight of active compound are present in the compositions to be used for the stain.
  • the application can be done before or during sowing.
  • the treatment of plant propagation material in particular the treatment of seed, are known to the person skilled in the art and are carried out by dusting, coating, pelleting, dipping or impregnating the plant propagation material, wherein the treatment preferably takes place by pelleting, coating and dusting or by furrow treatment, so that z. B. premature germination of the seed is prevented.
  • suspensions are preferably used.
  • Such compositions usually contain 1 to 800 g / l of active ingredient, 1 to 200 g / l of surfactants, 0 to 200 g / l of antifreeze, 0 to 400 g / l of binder, 0 to 200 g / l of dyes and solvents, preferably water.
  • the compounds may be used as such or in the form of their compositions, e.g. 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.
  • composition types depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • emulsions, pastes or oil dispersions the Substances as such or dissolved in an oil or solvent, are homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers.
  • concentrates which are active substance, adhesion, dispersant or emulsifier and, if appropriate, 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 compounds 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 crop protection range 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 especially between 0.1 and 0.75 kg per ha.
  • the application rate of active ingredient 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.
  • Oils of various types, wetting agents, adjuvants, herbicides, bactericides, other fungicides and / or pesticides may also be added to the active substances or the compositions containing them, if appropriate also immediately before use (tank mix). These agents can be added to the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
  • 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, eg. B. Pluronic RPE 2035 ® and Genapol B ®; Alcohol ethoxylates, eg. B. Lutensol ® XP 80; and sodium dioctylsulfosuccinate, e.g. B. Leophen ® RA.
  • 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
  • compositions of the invention may also be present in the application form as fungicides together with other active ingredients, for.
  • fungicides As with herbicides, insecticides, growth regulators, fungicides or with fertilizers, as a pre-mix or possibly only immediately before use (tank mix).
  • the activity spectrum can be broadened or resistance developments can be prevented. In many cases, one obtains synergistic see effects.
  • Azoxystrobin Dimoxystrobin, Coumoxystrobin, Coumethoxystrobin, Enestroburin, Fenaminstrobin, Fenoxystrobin / Flufenoxystrobin, Fluoxastrobin, Kresoxim-methyl, Metominostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Pyrametostrobin, Pyraoxystrobin, Pyribencarb, Triclopyricarb / Chlorodincarb, Trifloxystrobin, 2- [2- (2- 2,5-dimethylphenoxymethyl) phenyl) -3-methoxy-acrylic acid methyl ester, 2- (2- (3- (2,6-dichlorophenyl) -1-methyl-allylideneaminooxymethyl) -phenyl) -2-methoxyimino-N-methyl acetamides;
  • carboxylic acid anilides benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carbo-xin, fenfuram, fenhexamide, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl,
  • Benzoic acid amides flumetover, fluopicolide, fluopyram, zoxamide;
  • carboxamides carpropamide, diclocymet, mandipropamide, oxytetracycline, silthiofam, N- (6-methoxypyridin-3-yl) cyclopropanecarboxamide;
  • Triazoles azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole , Prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole;
  • - imidazoles cyazofamide, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizole;
  • Benzimidazoles benomyl, carbendazim, fuberidazole, thiabendazole;
  • Pyridines fluazinam, pyrifenox, 3- [5- (4-chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyridine, 3- [5- (4-methyl-phenyl) -2, 3-dimethyl-isoxazolidin-3-yl] -pyridine (pyrisoxazole); Pyrimidines: Bupirimat, Cyprodinil, Diflumetorim, Fenarimol, Ferimzone, Mepanipyrim, Nitrapyrin, Nuarimol, Pyrimethanil;
  • - piperazines triforins
  • - Pyrroles fludioxonil, fenpiclonil
  • 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 (fenpyrazine) ;
  • Guanidines dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadin tris (albesilat);
  • antibiotics kasugamycin, kasugamycin hydrochloride hydrate, polyoxines, streptomycin, validamycin A;
  • 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;
  • Bacillus subtilis strain NRRL no. B-21661 for example, the products Rhapsody ®, SERENADE ® MAX and SERENADE ® ASO of Fa. AgraQuest, Inc., USA.
  • Bacillus pum / '/ us strain NRRL no. B- 30087 eg SONATA ® and BALLAD ® Plus from. AgraQuest, Inc., USA
  • BotriZen Ltd. for example BOTRY ZEN Fa, New Zealand
  • Ulocladi- to oudemansii chitosan (eg ARMOR ZEN Fa. BotriZen Ltd. ., New Zealand).
  • Acetamides acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamide, pretilachlor, propachlor, thenylchloro;
  • Amino acid analogues bilanafos, glyphosate, glufosinate, sulfosate;
  • Aryloxyphenoxypropionates Clodinafop, Cyhalofop-butyl, Fenoxaprop, Fluazifop, Haloxyfop, Metamifop, Propaquizafop, Quizalofop, Quizalofop-P-tefuryl;
  • Bipyridyls diquat, paraquat;
  • Carbamates and thiocarbamates asulam, butylates, carbamides, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinates, orbencarb, phenmedipham, prosulphocarb, pyributicarb, thiobencarb, triallates;
  • - cyclohexanediones butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim; - Dinitroanilines: Benfluralin, Ethalfluralin, Oryzalin, Pendimethalin, Prodiamine, Trifluralin;
  • Diphenyl ether acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;
  • Hydroxybenzonitriles bromoxynil, dichlobenil, loxynil;
  • Imidazolinone imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr;
  • Phenoxyacetic acids clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, mecoprop;
  • - pyridines aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, pilinoram, picolinafen, thiazopyr;
  • Sulfonylureas amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, lodosulfuron, mesosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosul furon, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1 - ((2-chloro-6-prop
  • Triazines ametryn, atrazine, cyanazine, dimethametryn, ethiozine, hexazinone, metachronon, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam;
  • acetolactate synthase bispyribac sodium, cloransulam methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, orthosulphamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxime, pyriftalid, pyriminobac-methyl, pyrimisulphane, pyrithiobac, pyroxasulphone, pyroxsulam;
  • Organo (thio) phosphates acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfone, ethion, fenitrothion, fenthione, isoxathione, malathion, methamidophosphate, methidathion , Methyl parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidone, phorates, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorinophos, terbufos, triazophos, trichlorfon;
  • Carbamates alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb,
  • - pyrethroids allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin,
  • 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: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) Juvenoids: Pyriproxyfen, Methoprene, Fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spinotetramat;
  • 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-methyl-phenyl) -4-sulfinamoyl-1H-pyrazole-3-thiocarbon acid amide;
  • Macrocyclic lactones Abamectin, Emamectin, Milbemectin, Lepimectin, Spinosid, Spinetoram;
  • Inhibitors of mixed function oxidases piperonyl butoxide
  • the present invention also relates, in particular, to fungicidal compositions which comprise at least one compound of the general formula I and at least one further crop protection active ingredient, in particular at least one fungicidal active ingredient, eg. One or more, e.g. 1 or 2 active compounds of the abovementioned groups A) to F) and optionally one or more agriculturally suitable carriers.
  • fungicidal active ingredient eg. One or more, e.g. 1 or 2 active compounds of the abovementioned groups A) to F
  • agriculturally suitable carriers optionally one or more agriculturally suitable carriers.
  • the time sequence of the application of the active ingredients is of minor importance.
  • the weight ratio of compound I to the further active ingredient depends on the weight ratio of compound I to 1.
  • further active ingredient from the properties of the respective active ingredients it is usually in the range of 1: 100 to 100: 1, often in the range of 1:50 to 50: 1, preferably in the range of 1:20 to 20: 1, particularly preferred in the range of 1:10 to 10: 1, especially in the range of 1: 3 to 3: 1.
  • ie compositions according to the invention which contain an active substance I and a further active ingredient and a further active ingredient, eg. B.
  • the weight ratio of compound I to the first further active ingredient depends on the properties of the respective active ingredients, preferably in the range of 1: 50 to 50: 1 and in particular in the range from 1:10 to 10: 1.
  • the weight ratio of compound I to the second further active ingredient is preferably in the range from 1:50 to 50: 1, in particular in the range from 1:10 to 10: 1.
  • the weight ratio of further active ingredient to second active ingredient is preferably in the range from 1:50 to 50: 1, in particular in the range from 1:10 to 10: 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 that can be used to prepare an agrochemical composition of the invention.
  • these kits may contain one or more fungicidal component (s) and / or an adjuvant component and / or an insecticidal component and / or a growth regulator component and / or a herbicide.
  • fungicidal component s
  • an adjuvant component / or an insecticidal component and / or a growth regulator component and / or a herbicide.
  • One or more components may be combined or pre-formulated.
  • the components may be combined together and packaged in a single container such as a vessel, bottle, can, bag, sack or canister.
  • two or more components of a kit may be packaged separately, i. H. not pre-formulated or mixed.
  • Kits may contain one or more separate containers such as containers, bottles, cans, bags, sacks or canisters, each container containing a separate component of the agrochemical composition.
  • the components of the composition according to the invention can be mixed individually or already mixed or packaged as parts according to the modular principle ("kit of parts") and reused. In both forms, one component can be used separately or together with the other components or as part of a kit of parts according to the invention for the preparation of the mixture according to the invention.
  • the user usually uses the composition according to the invention for use in a pre-metering device, in the back splash, in the spray tank or in the spray plane.
  • the agrochemical composition with water and / or buffer is brought to the desired application concentration, optionally further adjuvants are added, and thus the ready-spray mixture or the agrochemical composition according to the invention is obtained.
  • 50 to 500 liters of ready-spray mixture per hectare of agricultural land preferably 100 to 400 liters.
  • the user may include individual components such as B. parts of a kit or a two or three-mixture of the invention. mix it yourself in the spray tank and, if necessary, add further auxiliaries (tank mix).
  • individual components such as B. parts of a kit or a two or three-mixture of the invention. mix it yourself in the spray tank and, if necessary, 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 a tank mix) or in succession apply.
  • compositions of a compound I with at least one active ingredient from group A) (component 2) of strobilurins and especially selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin.
  • compositions of a compound I having at least one active compound selected from group B) (component 2) of the carboxamides and especially selected from bixafen, boscalid, isopyrazam, fluopyram, penflufen, penthiopyrad, sedaxanes, fenhexamide, metalaxyl , Mefenoxam, ofurace, dimethomorph, flumorph, fluopicolide (picobenzamide), zoxamide, carpropamide, man- dipropamide and N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide.
  • compositions of a compound I having at least one active compound selected from the group E) (component 2) of the carambamates and especially selected from mancozeb, metiram, propineb, thiram, iprovalacarb, benthiavalicarb and propamocarb.
  • compositions of a compound I having at least one active substance selected from the fungicides of group F) (composite component 2) and especially selected from dithianone, fentin salts such as fentin acetate, fosetyl, fosetyl-aluminum, H3PO3 and its salts, chlorothalonil, dichlofluanid, thiophosphate-methyl, copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, cymoxanil, metrafenone , Spiroxamine and A / methyl 2- ⁇ 1 - [(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl) -acetyl] -piperidin-4-yl ⁇ -A / - [(1R ) -1,2,3,4-tetrahydronaphthalene-1-yl] -4-thiazolecarboxamide.
  • fentin salts such as fent
  • compositions of a compound I with at least one active ingredient selected from the fungicides of the biological fungicides (component 2) and especially selected from Bacillus subtilis strain NRRL no. B-21661, Bacillus pum / ' / us strain NRRL no. B-30087 and U-locladium oudemansii.
  • biological fungicides, plant tonics are:
  • Ampelomyces quisqualis 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. Fa. AgraQuest Inc., USA
  • Bacillus subtilis eg strain NRRL No. B-21661 in Rhapsody ®, SERENADE ® MAX and SERENADE ® ASO of. Fa.
  • Bacillus subtilis var amyloliquefaciens FZB24 eg the product TAEGRO ® from. Novozyme Biologicals, Inc., USA
  • Candida oleophila I-82 eg the product ASPIRE ® from. Ecogen Inc., USA
  • Candida saitoana eg the products BIOCURE ® (mixed with lysozyme) (and BIOCOAT ® of Micro Flo Company, Company, USA (BASF SE) and Arysta) chitosan eg .
  • Clonostachys rosea catenulata also called Gliocladium catenulatum (eg strain J1446: presTop ® from. Verdera, Finland), Coniothynum minitans (eg the product Contans ® from. Prophyta, Germany), Cryphonectna parasitica (eg the product Endothia parasitica the company CNICM, France), Cryptoworks tococcus albidus (eg the product YIELD PLUS ® from. Anchor Bio-Technologies, South Africa), Fusarium oxysporum (eg the products biofox ® from. Siapa, Italy, and FUSACLEAN ® from.
  • Gliocladium catenulatum also called Gliocladium catenulatum
  • Coniothynum minitans eg the product Contans ® from. Prophyta, Germany
  • Cryphonectna parasitica eg the product Endothia parasitica the company CNICM, France
  • REGALIA from Marrone Biolnnovations, United States
  • Talaromyces flavus V1 17b eg the P roduct protus ® from. Prophyta, Germany
  • T. harzianum JH 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., Israel 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 repurposeer ® WP Fa. Isagro Ricerca, Italy), T. polysporum and T. harzianum (eg the product Binab ® from.
  • 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., 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 oudeman- S // HRU3 eg the product BOTRY ZEN ® of Botry-Zen Ltd Company, New Zealand.
  • the present invention further relates to compositions of a compound I (component 1) with a further active ingredient (component 2), the latter selected from the lines B-1 to B-344 in the column "component 2" of Table B.
  • a further embodiment of the invention relates to the compositions B-1 to B-344 listed in Table B, wherein in each case one row of Table B corresponds to an agrochemical composition comprising an individualized in the present specification compounds of formula I (component 1) and the each further active compound from groups A) to I) (component 2) indicated in the respective line.
  • component 1 corresponds to a compound I which is individualized in Tables 1a to 257a.
  • the active compounds in the described compositions are each preferably present in synergistically effective amounts.
  • Table B Active ingredient composition comprising an individualized compound I and a further active compound from groups A) to I)
  • B-2 is an individualized compound I dimoxystrobin
  • B-15 is an individualized compound I idenaminooxymethyl) -phenyl) -2-methoxy-imino-N-methyl-acetamide
  • B-41 is an individualized compound I 2-amino-4-methylthiazole-5-carboxanilide
  • B-42 is an individualized compound I methyl-1-methyl-1H-pyrazole-4-carboxamide
  • B-43 is an individualized compound I 3-difluoromethyl-1-methyl-1H-pyrazole

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Abstract

La présente invention concerne des triazolylméthyloxiranes de formule I, dans laquelle R1 représente alkyle en C3 ou alkyle en C5 et les variables restantes sont telles que définies dans les revendications ou dans la description.
PCT/EP2010/068853 2009-12-08 2010-12-03 Composés triazoles, leur utilisation comme fongicides et agents les contenant WO2011069916A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2465350A1 (fr) * 2010-12-15 2012-06-20 Basf Se Mélanges de pesticides
US8729272B2 (en) 2010-03-16 2014-05-20 Basf Se Process using grignard reagents

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