EP2451784A1 - Dérivés de phényl(oxy/thio)alcanol - Google Patents

Dérivés de phényl(oxy/thio)alcanol

Info

Publication number
EP2451784A1
EP2451784A1 EP10729808A EP10729808A EP2451784A1 EP 2451784 A1 EP2451784 A1 EP 2451784A1 EP 10729808 A EP10729808 A EP 10729808A EP 10729808 A EP10729808 A EP 10729808A EP 2451784 A1 EP2451784 A1 EP 2451784A1
Authority
EP
European Patent Office
Prior art keywords
formula
plants
thio
compounds
oxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP10729808A
Other languages
German (de)
English (en)
Inventor
Carl Friedrich Nising
Klaus Kunz
Jörg Nico GREUL
Hendrik Helmke
Gorka Peris
Jürgen BENTING
Peter Dahmen
Isolde HÄUSER-HAHN
Ines Heinemann
Christian Paulitz
Dirk Schmutzler
Ulrike Wachendorff-Neumann
Tomoki Tsuchiya
Christoph Andreas Braun
Ruth Meissner
Thomas Knobloch
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Intellectual Property GmbH
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP10729808A priority Critical patent/EP2451784A1/fr
Publication of EP2451784A1 publication Critical patent/EP2451784A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur atoms
    • C07D213/34—Sulfur atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/34—Compounds containing oxirane rings with hydrocarbon radicals, substituted by sulphur, selenium or tellurium atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
    • 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

Definitions

  • the present invention relates to novel phenyl (oxy / thio) alkanol derivatives, processes for preparing these compounds, compositions containing these compounds, and their use as biologically active compounds, in particular for controlling harmful microorganisms in crop protection and material protection and as plant growth regulators.
  • X is 5-pyrimidinyl, 1H-1, 2,4-triazol-1-ylmethyl, 3-pyridinyl, 1H-1,3-imidazolylmethyl or
  • Y is O, S, SO, SO 2 or CH 2 ,
  • Z is bromine or iodine
  • R is tert-butyl, isopropyl, 1-halogenocyclopropyl, 1- (C 1 -C 4 -alkyl) cyclopropyl, 1 - (C 1 -C 4 -alkoxy) -cyclopropyl and 1 - (C 1 -C 4 -alkylthio) cyclopropyl,
  • the salts thus obtainable also have fungicidal and / or plant growth regulatory properties.
  • the phenyl (oxy / thio) alkanol derivatives which can be used according to the invention are generally defined by the formula (I).
  • Preferred radical definitions of the above and below formulas are given in the following. These definitions apply equally to the end products of formula (I) as well as to all intermediates (see also below under “Explanatory Notes on Processes and Intermediates”).
  • X preferably represents 5-pyrimidinyl, 1H-1, 2,4-triazol-1-ylmethyl, 3-pyridinyl or 2,4-dihydroxyethyl
  • X is more preferably 5-pyrimidinyl.
  • X is also particularly preferred for 1H-1,2,4-triazole-1-methylmethane.
  • X is also particularly preferably 2,4-dihydro-3H-1, 2,4-triazole-3-thion-1-ylmethyl.
  • X is most preferably 5-pyrimidinyl.
  • X is also most preferably LH-l, 2,4-triazol-1-ylmethyl.
  • Y is preferably O, S or CH 2 .
  • Y is particularly preferably O or CH 2 .
  • Y is most preferably O.
  • Z is preferably bromine.
  • Z is also preferably iodine.
  • Z is particularly preferably bromine, which is in the 4-position.
  • Z is also particularly preferably bromine, which is in the 3-position.
  • Z is also particularly preferably bromine, which is in the 2-position.
  • Z is also particularly preferably iodine, which is in the 4-position.
  • Z is also particularly preferably iodine, which is in the 3-position.
  • Z is also particularly preferably iodine, which is in the 2-position.
  • R preferably represents tert-butyl, isopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-methylcyclopropyl, 1-methoxycyclopropyl and 1-methylthiocyclopropyl.
  • R is particularly preferably tert-butyl, isopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl or
  • R very particularly preferably represents tert-butyl
  • R is also most preferably isopropyl.
  • R is also very particularly preferably 1-chlorocyclopropyl.
  • R is also very particularly preferably 1-fluorocyclopropyl.
  • R is also very particularly preferably 1-methylcyclopropyl.
  • a further embodiment of the present invention relates to compounds of the formula (Ia)
  • a further embodiment of the present invention relates to compounds of the formula (Ib)
  • Another embodiment of the present invention relates to compounds of the formula (Ic)
  • Z is preferably iodine.
  • a further embodiment of the present invention relates to compounds of the formula (Id)
  • Z is preferably iodine.
  • Another embodiment of the present invention relates to compounds of the formula (Ie) in which Y, Z and R have the meanings given above.
  • Another embodiment of the present invention relates to compounds of the formula (If) in which Y, Z and R have the meanings given above.
  • Another embodiment of the present invention are compounds of formula (I) wherein Z is bromo and R is tert -butyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which Z is bromine and R is isopropyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which Z is bromine and R is 1-chlorocyclopropyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which Z is bromine and R is 1-fluorocyclopropyl.
  • Another embodiment of the present invention are compounds of formula (I) wherein Z is bromo and R is 1-methylcyclopropyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which
  • Z is iodine and R is tert-butyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which
  • Z is iodine and R is isopropyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which
  • Z is iodine and R is 1-chlorocyclopropyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which
  • Z is iodine and R is 1-fluorocyclopropyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which Z is iodine and R is 1-methylcyclopropyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which Z is bromine, R is tert-butyl and X is 5-pyrimidinyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which Z is bromine, R is tert-butyl and X is 1H-1,2,4-triazol-1-ylmethyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which Z is bromine, R is tert-butyl and X is 3-pyridinyl.
  • a further embodiment of the present invention are compounds of the formula (I) in which Z is bromine, R is tert-butyl and X is 2,4-dihydro-3H-1, 2,4-triazole-3-thione-1 ylmethyl stands.
  • Another embodiment of the present invention are compounds of the formula (I) in which Z is bromine, R is isopropyl and X is 5-pyrimidinyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which
  • Z is bromine, R is isopropyl and X is 1H-l, 2,4-triazol-1-ylmethyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which
  • Z is bromine, R is isopropyl and X is 3-pyridinyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which
  • Z is bromine, R is isopropyl and X is 2,4-dihydro-3H-1, 2,4-triazole-3-thion-1-ynethyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which Z is bromine, R is 1-chlorocyclopropyl and X is 5-pyrimidinyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which Z is bromine, R is 1-chlorocyclopropyl and X is 1H-l, 2,4-triazol-1-ynethyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which Z is bromine, R is 1-chlorocyclopropyl and X is 3-pyridinyl.
  • a further embodiment of the present invention are compounds of the formula (I) in which Z is bromine, R is 1-chlorocyclopropyl and X is 2,4-dihydro-3H-1, 2,4-triazole-3-thione-1 ylmethyl stands.
  • Another embodiment of the present invention are compounds of the formula (I) in which Z is bromine, R is 1-fluorocyclopropyl and X is 5-pyrimidinyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which
  • Z is bromine, R is 1-fluorocyclopropyl and X is 1H-1-triazol-1-ylmethyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which
  • Z is bromine, R is 1-fluorocyclopropyl and X is 3-pyridinyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which
  • Z is bromine, R is 1-fluorocyclopropyl and X is 2,4-dihydro-3H-1, 2,4-triazole-3-thion-1-ynethyl.
  • Another embodiment of the present invention are compounds of formula (I) in which Z is iodo, R is tert -butyl and X is 5-pyrimidinyl.
  • Another embodiment of the present invention are compounds of formula (I) in which Z is iodo, R is tert -butyl and X is 1H-l, 2,4-triazol-1-ylmethyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which Z is iodine, R is tert-butyl and X is 3-pyridinyl.
  • a further embodiment of the present invention are compounds of the formula (I) in which Z is iodine, R is tert-butyl and X is 2,4-dihydro-3H-1, 2,4-triazole-3-thione-1 yhnethyl stands.
  • Another embodiment of the present invention are compounds of the formula (I) in which
  • Z is iodo
  • R is isopropyl
  • X is 5-pyrimidinyl
  • Another embodiment of the present invention are compounds of the formula (I) in which
  • Z is iodine, R is isopropyl and X is 1H-l, 2,4-triazol-1-ylmethyl.
  • Another embodiment of the present invention are compounds of formula (I) in which Z is iodo, R is isopropyl and X is 3-pyridinyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which
  • Z is iodine, R is isopropyl and X is 2,4-dihydro-3H-1, 2,4-triazole-3-thion-1-ylmethyl.
  • Another embodiment of the present invention are compounds of formula (I) wherein Z is iodo, R is 1-chlorocyclopropyl and X is 5-pyrimidinyl.
  • Another embodiment of the present invention are compounds of formula (I) in which Z is iodo, R is 1-chlorocyclopropyl and X is 1H-l, 2,4-triazol-1-ylmethyl.
  • a further embodiment of the present invention are compounds of the formula (I) in which Z is iodine, R is 1-chlorocyclopropyl and X is 3-pyridinyl.
  • a further embodiment of the present invention are compounds of the formula (I) in which Z is iodine, R is 1-chlorocyclopropyl and X is 2,4-dihydro-3H-1, 2,4-triazole-3-thione-1 ylmethyl stands.
  • Another embodiment of the present invention are compounds of formula (I) wherein Z is iodo, R is 1-fluorocyclopropyl and X is 5-pyrimidinyl.
  • a further embodiment of the present invention are compounds of the formula (I) in which Z is iodine, R is 1-fluorocyclopropyl and X is 1H-1,2,4-triazol-1-ylmethyl.
  • Another embodiment of the present invention are compounds of formula (I) wherein Z is iodo, R is 1-fluorocyclopropyl and X is 3-pyridinyl.
  • a further embodiment of the present invention are compounds of the formula (I) in which Z is iodine, R is 1-fluorocyclopropyl and X is 2,4-dihydro-3H-1, 2,4-triazole-3-thione-1 ylmethyl stands.
  • Another embodiment of the present invention are compounds of the formula (I) in which
  • Z is bromine, R is 1-methylcyclopropyl and X is 5-pyrimidinyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which
  • Z is bromine, R is 1-methylcyclopropyl and X is 1H-l, 2,4-triazol-1-ylmethyl.
  • Another embodiment of the present invention are compounds of the formula (I) in which
  • Z is bromine, R is 1-methylcyclopropyl and X is 3-pyridinyl.
  • a further embodiment of the present invention are compounds of the formula (I) in which Z is bromine, R is 1-methylcyclopropyl and X is 2,4-dihydro-3H-1, 2,4-triazole-3-thione-1 ymiethyl stands.
  • A is CH or N
  • oxirane derivatives of the formula (II) required as starting materials for carrying out process A according to the invention are novel, the compound 2- [2- (4-bromophenyl) ethyl] -2- (1-methylcyclopropyl ) oxirane is excluded. They can be prepared by known processes from the phenyloxy (thio) ketones of the formula (VI) (cf., EP-A 0 040 345).
  • Process A according to the invention is carried out in the presence of a diluent and if appropriate in the presence of a base.
  • a base optionally, an acid or a metal salt is added to the resulting compound of formula (I-g) (see below).
  • Suitable diluents for the erf ⁇ ndungshiele reaction all inert organic solvents. These include, preferably, alcohols, e.g. Ethanol and methoxyethanol; Ketones, e.g. 2-butanone; Nitriles, e.g. acetonitrile; Esters, e.g. Essigester; Ethers, e.g. dioxane; aromatic hydrocarbons, e.g. benzene and toluene; or amides, e.g. Dimethylformamide.
  • alcohols e.g. Ethanol and methoxyethanol
  • Ketones e.g. 2-butanone
  • Nitriles e.g. acetonitrile
  • Esters e.g. Essigester
  • Ethers e.g. dioxane
  • aromatic hydrocarbons e.g. benzene and toluene
  • amides e.g. Di
  • Suitable bases for the reaction according to the invention are all customary organic and inorganic bases. These include, preferably, alkali carbonates, e.g. Sodium or potassium carbonate; Alkali hydroxides, e.g. sodium hydroxide; Alkali alcoholates, e.g. Sodium and potassium methylate and ethylate; Alkali hydrides, e.g. sodium hydride; as well as lower tertiary alkylamines, cycloalkylamines and aralkylamines, in particular triethylamine.
  • alkali carbonates e.g. Sodium or potassium carbonate
  • Alkali hydroxides e.g. sodium hydroxide
  • Alkali alcoholates e.g. Sodium and potassium methylate and ethylate
  • Alkali hydrides e.g. sodium hydride
  • the reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, one works at temperatures between 0 0 C and 200 0 C, preferably between 60 0 C and 150 0 C.
  • the reaction of the invention may optionally be carried out under elevated pressure. In general, one works between 1 and 50 bar, preferably between 1 and 25 bar.
  • oxirane derivatives of the formula (IV) required as starting materials when carrying out the process B according to the invention are partially new. They can be prepared by known processes from the corresponding triazolyl ketones (cf., DE-A 31 11 238, EP-A 0 157 712). New are oxirane derivatives of the formula (IV-a)
  • R a represents isopropyl, L-halogenocyclopropyl, C 1 -C 4 -alkyl) cyclopropyl, C 1 -C 4 -alkoxycyclopropyl and C 1 -C 4 -alkylthio) cyclopropyl,
  • A is CH or N
  • R a is preferably isopropyl, 1-chlorocyclopropyl, 1-methylcyclopropyl, 1-methoxycyclopropyl and 1-methylthiocyclopropyl.
  • R a is particularly preferably isopropyl, 1-chlorocyclopropyl or 1-methylcyclopropyl.
  • R a is very particularly preferably isopropyl. Also new are oxirane derivatives of the formula (FV-b)
  • A is CH or N
  • R is not tert-butyl when A is CH.
  • R is preferably, more preferably or very particularly preferably of the abovementioned meanings, R in each case not being tert-butyl, when A is CH.
  • Process B according to the invention is carried out in the presence of a diluent and if appropriate in the presence of a base.
  • a diluent e.g., a diluent
  • a base e.g., a diluent
  • an acid or a metal salt is added to the resulting compound of formula (I-h) (see below).
  • Suitable diluents for the reaction according to the invention are all inert organic solvents. These include, preferably, alcohols, such as ethanol and methoxyethanol; ketones, such as 2-butanone; Nitriles, such as acetonitrile; Esters, such as ethyl acetate; Ethers, such as dioxane; aromatic hydrocarbons, such as benzene and toluene; or amides, such as dimethylformamide.
  • alcohols such as ethanol and methoxyethanol
  • ketones such as 2-butanone
  • Nitriles such as acetonitrile
  • Esters such as ethyl acetate
  • Ethers such as dioxane
  • aromatic hydrocarbons such as benzene and toluene
  • amides such as dimethylformamide.
  • Suitable bases for the reaction according to the invention are all customary organic and inorganic bases. These include, preferably, alkali carbonates, e.g. Sodium or potassium carbonate; Alkali hydroxides, e.g. sodium hydroxide; Alkali alcoholates, e.g. Sodium and potassium methylate and ethylate; Alkali hydrides, e.g. sodium hydride; as well as lower tertiary alkylamines, cycloalkylamines and aralkylamines, in particular triethylamine. Particular preference is given to using sodium hydride.
  • alkali carbonates e.g. Sodium or potassium carbonate
  • Alkali hydroxides e.g. sodium hydroxide
  • Alkali alcoholates e.g. Sodium and potassium methylate and ethylate
  • Alkali hydrides e.g. sodium hydride
  • Particular preference is given to using sodium hydride.
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, one works at temperatures between 0 0 C and 200 0 C, preferably between 60 0 C and 150 0 C.
  • the reaction according to the invention may optionally be carried out under elevated pressure.
  • oxirane of the general formula (IV) is preferably 1 to 2 moles (thio) phenol of the formula (V) and optionally 1 to 2 moles of base.
  • the isolation of the end products takes place in a generally customary manner.
  • the phenyl (oxy / thio) ketones of the formula (VI) required as starting materials in carrying out the process C according to the invention are novel, Y not being O or CH 2 when Z is bromine. They can be prepared in a known manner (cf EP-A 0040 345, EP-A 0 001 399).
  • Hal is preferably chlorine or bromine.
  • Suitable inert diluents for the reaction according to the invention are preferably inert organic solvents. These preferably include those which have a low fixed point, in particular ethers, such as diethyl ether or tetrahydrofuran. Preferably, one works with mixtures of these two ethers.
  • Alkali metal-organic compounds used in the reaction according to the invention are preferably alkali metal alkyls, in particular n-butyl lithium; However, it is also possible to use alkali metal aryls, such as phenyl-lithium.
  • the reaction temperatures can be varied within a certain range in the process according to the invention. In general, it is carried out between -150 0 C and -50 0 C, preferably between -120 ° C and -80 0 C.
  • the reaction according to the invention is preferably carried out under inert gas, in particular nitrogen or argon.
  • the phenyloxy (thio) ketones of the formula (VI) and the halides of the formula (VII) are added in approximately equimolar amounts, but under or overshoots of up to about 20 mole percent are possible.
  • the alkali metal-organic compound is advantageously used in excess of from 5 to 75 mole percent, preferably from 10 to 50 mole percent.
  • the phenyl (oxy / thio) ketones of the formula (EX) occurring as intermediates in carrying out the process D according to the invention are novel, where Z is not bromine, if X 4 is 3-pyridinyl. They can be prepared in a known manner (cf JP-A 62-084061, WO 01/87878).
  • organometallic compounds of the formula (X) are known, where M in the formula (X) is preferably lithium or magnesium.
  • Process D according to the invention (step 1) is carried out in the presence of a diluent and, if appropriate, in the presence of a base.
  • Suitable diluents for the reaction according to the invention are all inert organic solvents. These include, preferably, alcohols, such as ethanol and methoxyethanol; Ketones such as 2-butanone; Nitriles, such as acetonitrile; Esters, such as ethyl acetate; Ethers, such as dioxane; aromatic hydrocarbons, such as, for example, benzene and toluene; or amides, such as dimethylformamide.
  • Suitable bases for the reaction according to the invention are all customary organic and inorganic bases.
  • alkali metal carbonates such as sodium or potassium carbonate
  • Alkali hydroxides such as sodium hydroxide
  • Alkali alcoholates such as sodium and potassium methylate and ethylate
  • Alkali metal hydrides such as sodium hydride
  • alkali metal carbonates such as sodium or potassium carbonate
  • Alkali hydroxides such as sodium hydroxide
  • Alkali alcoholates such as sodium and potassium methylate and ethylate
  • Alkali metal hydrides such as sodium hydride
  • lower tertiary alkylamines, cycloalkylamines and aralkylamines in particular triethylamine.
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, one works at temperatures between 0 0 C and 200 0 C, preferably between 20 0 C and 100 0 C.
  • the erf ⁇ ndungshiele reaction may optionally be carried out under elevated pressure. In general, one works between 1 and 50 bar, preferably between 1 and 25 bar.
  • step 1 When carrying out the process D according to the invention (step 1), 1 to 2 mol of (thio) phenol of the formula (V) and, if appropriate, 1 to 3 mol of base are used per mole of bromoketone of the general formula (VIII).
  • step 2 When carrying out the process D according to the invention (step 1), 1 to 2 mol of (thio) phenol of the formula (V) and, if appropriate, 1 to 3 mol of base are used per mole of bromoketone of the general formula (VIII).
  • step 2 mol of (thio) phenol of the formula (V) and, if appropriate, 1 to 3 mol of base are used per mole of bromoketone of the general formula (VIII).
  • the inventive method D (step 2) is carried out in the presence of a diluent and in the presence of an alkali metal-organic compound.
  • an acid or a metal salt is added to the resulting compound of formula (I-k) (see below).
  • suitable diluents are preferably inert organic solvents. These include, in particular, ethers, such as diethyl ether or tetrahydrofuran.
  • alkali metal-organic compounds in the reaction according to the invention preferably alkaline earth metal alkyls, such as in particular t-butyl magnesium chloride used; however, it is also possible to use alkali metal alkyls, such as t-butyllithium.
  • the reaction temperatures can be varied within a certain range in the process according to the invention. Generally carried out between -100 C and +20 0 ° C, preferably between -78 0 C and 0 0 C.
  • the reaction according to the invention is preferably carried out under inert gas, in particular nitrogen or argon.
  • inert gas in particular nitrogen or argon.
  • the ketones of the formula (DC) and the organometallic compounds of the formula (X) are added in approximately equimolar amounts, but underflows or excesses of up to about 20 mol% are possible.
  • the organometallic compound is advantageously used in excess of from 5 to 75 mole percent, preferably from 10 to 50 mole percent.
  • the reaction of the phenyl (oxy / thio) alkanol derivatives of the formula (I-c) to give phenyl (oxy / thio) alkanol derivatives of the formula (I-e) can be carried out in two different ways (cf., EP-A 0 793 657).
  • Sulfur is preferably used in the form of powder.
  • variant ( ⁇ ) water is used for the hydrolysis, if appropriate in the presence of an acid.
  • an acid In question here are all customary for such reactions inorganic or organic acids.
  • acetic acid, dilute sulfuric acid and dilute hydrochloric acid Preferably usable are acetic acid, dilute sulfuric acid and dilute hydrochloric acid.
  • aqueous ammonium chloride solution it is also possible to carry out the hydrolysis with aqueous ammonium chloride solution.
  • the reaction temperatures can be varied within a certain range when carrying out variant ( ⁇ ). In general, one operates at temperatures between -7O 0 C and +20 0 C, preferably between -70 0 C and 0 0 C.
  • carrying out the process E according to the invention is generally carried out under atmospheric pressure. But it is also possible to work under increased or reduced pressure. Thus, especially when carrying out the variant ( ⁇ ) working under increased pressure in question.
  • amides such as dimethylformamide and dimethylacetamide
  • heterocyclic compounds such as N-methylpyrrolidone
  • ethers such as diphenyl ether.
  • Sulfur is also used in carrying out the process E according to the invention variant (ß) generally in the form of powder.
  • treatment with water and optionally with acid can be carried out. This is carried out as the hydrolysis in carrying out the variant ( ⁇ ).
  • reaction temperatures can also be varied within a relatively wide range when carrying out the process E, variant ( ⁇ ) according to the invention. In general, one works at temperatures between 15O 0 C and 300 0 C, preferably between 180 0 C and 250 0 C.
  • E variant (ß) is used for 1 mole of phenyl (oxy / thio) alkanol derivatives of the formula (I-c) generally 1 to 5 moles, preferably 1.5 to 3 moles of sulfur.
  • the workup is carried out by conventional methods.
  • the compounds of the general formula (I) obtainable by the processes A to E according to the invention can be converted into acid addition salts or metal salt complexes.
  • hydrohalic acids such as e.g. Hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, also phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as e.g. Acetic, maleic, succinic, fumaric, tartaric, citric, salicylic, sorbic, lactic and sulfonic acids, e.g. p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid.
  • hydrohalic acids such as e.g. Hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, also phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as e.g. Acetic, maleic, succinic, fumaric, tartaric, citric, salicylic, sorbic, lactic and sulfonic acids,
  • the acid addition salts of the compounds of general formula (I) can be easily prepared by conventional salt formation methods, e.g. by dissolving a compound of general formula (I) in a suitable inert solvent and adding the acid, e.g. Hydrochloric acid, and in a known manner, e.g. by filtration, isolated and optionally purified by washing with an inert organic solvent.
  • a suitable inert solvent e.g. Hydrochloric acid
  • Suitable anions of the salts are those which are preferably derived from the following acids: hydrohalic acids, such as, for example, hydrochloric acid and hydrobromic acid, and also phosphoric acid, nitric acid and sulfuric acid.
  • hydrohalic acids such as, for example, hydrochloric acid and hydrobromic acid
  • phosphoric acid such as, for example, nitric acid and sulfuric acid.
  • the metal salt complexes of compounds of the general formula (I) can be obtained in a simple manner by customary processes, for example by dissolving the metal salt in alcohol, for example ethanol, and adding to the compound of general formula I.
  • Metal salt complexes can be prepared in known manner , For example, isolate by filtration and optionally purified by recrystallization.
  • the present invention further relates to an agent for controlling unwanted microorganisms comprising the active compounds according to the invention. Preference is given to fungicidal compositions containing agriculturally useful auxiliaries, solvents, excipients, surface-
  • the invention relates to a method for controlling unwanted microorganisms, characterized in that the active compounds according to the invention are applied to the phytopathogenic fungi and / or their habitat.
  • the carrier means a natural or synthetic, organic or inorganic substance with which the active ingredients for better applicability, v. A. for planting or plant parts or seeds, mixed or connected.
  • the carrier which may be solid or liquid, is generally inert and should be useful in agriculture.
  • Suitable solid or liquid carriers are: e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly-dispersed silicic acid, alumina and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol, organic solvents, mineral and vegetable oils and derivatives thereof. Mixtures of such carriers can also be used.
  • Suitable solid carriers for granules are: e.g.
  • Suitable liquefied gaseous diluents or carriers are those liquids which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.
  • Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, natural phospholipids such as cephalins and lecithins, and synthetic phospholipids.
  • Other additives may be mineral and vegetable oils.
  • Suitable liquid solvents are essentially: aromatics, such as
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or dichloromethane
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils
  • alcohols such as butanol or glycol
  • the agents of the invention may additionally contain other ingredients, e.g. surfactants.
  • Suitable surface-active substances are emulsifying and / or foam-forming agents, dispersants or wetting agents having ionic or nonionic properties or mixtures of these surface-active substances.
  • Examples thereof are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyltaurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, eg Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignin-sulphite liquors and methylcellulose.
  • the presence of a surfactant is necessary when one of the active ingredients
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • additional components e.g. protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, stabilizers, sequestering agents, complexing agents.
  • the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.
  • compositions and formulations according to the invention contain between 0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1 and 95% by weight, particularly preferably between 0.5 and 90%.
  • Active ingredient most preferably between 10 and 70 weight percent.
  • the active compounds or compositions according to the invention can be used as such or as a function of their physical and / or chemical properties in the form of their formulations or the use forms prepared therefrom, such as aerosols, capsule suspensions, cold mist concentrates, hot mist concentrates, encapsulated granules, fine granules, flowable concentrates for the treatment of seeds, ready-to-use solutions, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, macrogranules, microgranules, oil-dispersible powders, oil-miscible, flowable concentrates, oil-miscible liquids, foams, pastes , Pesticide-coated seeds, suspension concentrates, suspension-emulsion concentrates, soluble concentrates, suspensions, wettable powders, soluble powders, dusts and granules, water-soluble granules or tablets, water-soluble powders for seed treatment,
  • the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active compounds with at least one customary diluent, solvent or diluent, emulsifier, dispersing and / or binding or fixing agent, wetting agent, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments, defoaming agents, preservatives, secondary thickeners, adhesives, gibberellins and other processing aids.
  • compositions according to the invention comprise not only formulations which are already ready for use and which can be applied to the plant or seed by suitable equipment, but also commercial concentrates which have to be diluted with water before use.
  • the active compounds according to the invention as such or in their (commercial) formulations and in the formulations prepared from these formulations in admixture with other (known) agents such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers , Safeners or semiochemicals.
  • agents such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers , Safeners or semiochemicals.
  • the erf ⁇ ndungsdorfe treatment of the plants and plant parts with the active ingredients or agents is carried out directly or by affecting the environment, habitat or storage space according to the usual treatment methods, e.g.
  • the invention further comprises a method of treating seed.
  • the invention further relates to seed which has been treated according to one of the methods described in the previous paragraph.
  • the seeds according to the invention are used in methods for the protection of seed from undesirable microorganisms.
  • a seed treated with at least one active ingredient according to the invention is used.
  • the active compounds or compositions according to the invention are also suitable for the treatment of seed.
  • Much of the damage to crop plants caused by harmful organisms is caused by the seed being dropped during storage or after sowing, as well as during and after germination of the plant. This phase is particularly critical because the roots and shoots of the growing plant are particularly sensitive and can cause only a small damage to the death of the plant. There is therefore a great interest in protecting the seed and the germinating plant by using suitable means.
  • the control of phytopathogenic fungi by the treatment of the seed of plants has long been known and is the subject of constant improvement. Nevertheless, there are a number of problems in the treatment of seeds that can not always be satisfactorily resolved.
  • methods for protecting the seed and the germinating plant which eliminate or at least significantly reduce the additional application of crop protection agents after sowing or after emergence of the plants. It is furthermore desirable to optimize the amount of the active ingredient used in such a way that the seed and the germinating plant are best protected against attack by phytopathogenic fungi, without, however, damaging the plant itself by the active ingredient used.
  • methods for treating seed should also include the intrinsic fungicidal properties of transgenic plants in order to achieve optimum protection of the seed and the germinating plant with a minimum of pesticides.
  • the present invention therefore also relates to a method of protecting seed and germinating plants from the infestation of phytopathogenic fungi by treating the seed with an agent of the invention.
  • the invention also relates to the use of the seed treatment agents according to the invention for the protection of the seed and of the germinating plant from phytopathogenic fungi.
  • the invention relates to seed which has been treated with an agent according to the invention for protection against phytopathogenic fungi.
  • One of the advantages of the present invention is that because of the particular systemic properties of the active compounds or compositions according to the invention, the treatment of the seed with these active substances or agents not only the seed itself, but also the resulting plants after emergence before phytopathogenic Protects mushrooms. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
  • the active compounds or agents according to the invention can also be used in particular in the case of transgenic seed, wherein the plant growing from this seed is capable of expressing a protein which acts against pests.
  • certain pests can already be controlled by the expression of the insecticidal protein, for example.
  • a further synergistic effect can be observed, which additionally increases the effectiveness for protection against pest infestation.
  • the compositions according to the invention are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture and viticulture.
  • acts these are seeds from cereals (such as wheat, barley, rye, triticale, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, bean, coffee, turnip (eg sugarbeet and fodder), peanut, rapeseed, Poppy, olive, coconut, cocoa, sugarcane, tobacco, vegetables (such as tomato, cucumber, onions and lettuce), turf and ornamental plants (see also below).
  • cereals such as wheat, barley, rye, triticale, millet and oats
  • corn cotton, soy, rice, potatoes, sunflower, bean, coffee, turnip (eg sugarbeet and fodder), peanut, rapeseed, Poppy, olive, coconut, cocoa, sugarcane, tobacco, vegetables (such as tomato, cucumber, onions and lettuce), turf and ornamental plants (see also below).
  • cereals such as wheat, barley, rye, triticale, millet and oats
  • corn such as wheat, barley,
  • transgenic seed As also described below, the treatment of transgenic seed with the active compounds or agents according to the invention is of particular importance.
  • the heterologous gene in transgenic seed may e.g. come from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or GIi- ocladium.
  • this heterologous gene is derived from Bacillus sp., Wherein the gene product has an activity against the European corn borer and / or Western Com Rootworm.
  • the heterologous gene is from Bacillus thuringiensis.
  • the agent according to the invention is applied to the seed alone or in a suitable formulation.
  • the seed is treated in a condition that is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp.
  • seed may be used which has been harvested, cleaned and dried to a moisture content below 15% by weight.
  • seed may also be used which, after drying, e.g. treated with water and then dried again.
  • care must be taken during the treatment of the seed that the amount of the agent and / or further additives applied to the seed is chosen so that germination of the seed is not impaired or the resulting plant is not damaged. This must be taken into account, above all, with active ingredients which can show phytotoxic effects at certain application rates.
  • the agents according to the invention can be applied directly, ie without containing further components and without being diluted.
  • suitable formulations and methods for seed treatment are known to those skilled in the art and are described e.g. in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430 A, US 5,876,739 A, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002/028186 A2.
  • the active compounds which can be used according to the invention can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as ULV formulations.
  • These formulations are prepared in a known manner by mixing the active ingredients with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and water.
  • Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, CI. Pigment Red 112 and CI. Solvent Red 1 known dyes.
  • Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances which are customary for the formulation of agrochemical active compounds. Preference is given to using alkylnaphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds.
  • Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are, in particular, lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
  • Preferably usable are silicone defoamers and magnesium stearate.
  • Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.
  • Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents. Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
  • the gibberellins are known (see R. Wegler "Chemie der convinced für Schweizer- und Swdlingsbekungsstoff", Vol 2, Springer Verlag, 1970, pages 401-412).
  • the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water For the treatment of seed of various kinds, including seeds of transgenic plants, additional synergistic effects may occur in conjunction with the substances produced by expression.
  • the seed dressing formulations which can be used according to the invention or the preparations prepared therefrom by the addition of water
  • all mixing devices customarily usable for the dressing can be considered.
  • the seed is placed in a mixer which adds either desired amount of seed dressing formulations either as such or after prior dilution with water and mixes until evenly distributed the formulation on the seed.
  • a drying process follows.
  • the active compounds or compositions according to the invention have a strong microbicidal action and can be used for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
  • Fungicides can be used for the control of Plasmodiophoromycetes, Oomycetes, Chytriomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, En- terbacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • the fungicidal compositions according to the invention can be used curatively or protectively for controlling phytopathogenic fungi.
  • the invention therefore also relates to curative and protective methods for controlling phytopathogenic fungi by the use of the active compounds or agents according to the invention, which is applied to the seed, the plant or plant parts, the fruits or the soil in which the plants grow.
  • compositions of the invention for controlling phytopathogenic fungi in plant protection comprise an effective but non-phytotoxic amount of the active compounds of the invention.
  • Effective but non-phytotoxic amount means an amount of the agent of the invention sufficient to sufficiently control the fungal disease of the plant This rate of application may generally vary over a wide range, depending on several factors, including the fungus to be controlled, the plant, the climatic conditions and the ingredients of the plant Inventive means.
  • the good plant tolerance of the active ingredients in the necessary concentrations for controlling plant diseases allows treatment of aboveground plant parts, of plant and seed, and the soil.
  • plants are understood as meaning all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
  • Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes become.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the active compounds according to the invention are suitable for good plant tolerance, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the crop. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • plants which can be treated according to the invention mention may be made of the following: cotton, flax, grapevine, fruits, vegetables, such as Rosaceae sp.
  • pomegranates such as apple and pear, but also drupes such as apricots, cherries, almonds and peaches and soft fruits such as strawberries
  • Rissesidae sp. Juglandaceae sp.
  • Betulaceae sp. Anacardiaceae sp., Fagaceae sp., Moraceae sp. , Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example, banana trees and plantations), Rubiaceae sp.
  • Asteraceae sp. for example sunflower
  • Brassicaceae sp. for example, white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes and rapeseed, mustard, horseradish and cress
  • Fabacae sp. for example, bean, peanuts
  • Papilionaceae sp. for example, soybean
  • Solanaceae sp. for example potatoes
  • Chenopodiaceae sp. for example, sugar beet, fodder beet, Swiss chard, beet
  • plants and their parts can be treated.
  • wild or conventional biological Breeding methods such as crossing or protoplasting preserved plant species and plant varieties and their parts treated.
  • transgenic plants and plant cultivars obtained by genetic engineering if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term "parts” or “parts of plants” or “parts of plants” has been explained above.Propes of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention.PV plants are understood as meaning plants with new properties ("traits”) have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques.
  • the treatment method of the invention may be used for the treatment of genetically modified organisms (GMOs), e.g. As plants or seeds are used.
  • GMOs genetically modified organisms
  • Genetically modified plants are plants in which a heterologous gene has been stably integrated into the genome.
  • heterologous gene essentially means a gene which is provided or assembled outside the plant and which, when introduced into the nuclear genome, the chloroplast genome or the hypochondriacal genome, imparts new or improved agronomic or other properties to the transformed plant Expressing protein or polypeptide or that it downregulates or shuts down another gene present in the plant or other genes present in the plant (for example by means of antisense technology, cosuppression technology or RNAi technology [RNA Interference])
  • a heterologous gene present in the genome is also referred to as a transgene
  • a transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event.
  • the treatment according to the invention can also lead to superadditive (“synergistic”) effects.
  • the following effects are possible expected effects: reduced rates of application and / or extended spectrum of activity and / or increased efficacy of the active ingredients and compositions which can be used according to the invention, improved plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or water or soil salt content, increased Flowering, harvest relief, ripening, higher yields, larger fruits, greater plant height, intense green color of the leaf, earlier flowering, higher quality and / or higher nutritional value of the harvested products, higher sugar concentration in the F crops, better shelf life and / or processability of the harvested products.
  • the active compounds according to the invention can also exert a strengthening effect on plants. They are therefore suitable for mobilizing the plant defense system against attack by undesirable phytopathogenic fungi and / or microorganisms and / or viruses. This may optionally be one of the reasons for the increased efficacy of the combinations according to the invention, for example against fungi.
  • Plant-strengthening (resistance-inducing) substances are to be used in the present.
  • those substances or substance combinations which are capable of stimulating the plant defense system in such a way that the treated plants, when subsequently inoculated with undesirable phytopathogenic fungi have a considerable degree of resistance to these undesired phytopathogenic fungi.
  • the substances according to the invention can therefore be employed for the protection of plants against attack by the mentioned pathogens within a certain period of time after the treatment.
  • the period of time over which a protective effect is achieved generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active substances.
  • Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material which gives these plants particularly advantageous, useful features (regardless of whether this was achieved by breeding and / or biotechnology).
  • Plants and plant varieties which are also preferably treated according to the invention are resistant to one or more biotic stressors, i. H. These plants have an improved defense against animal and microbial pests such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.
  • Plants and plant varieties which can also be treated according to the invention are those plants which are resistant to one or more abiotic stress factors.
  • Abiotic stress conditions may include, for example, drought, cold and heat conditions, osmotic stress, waterlogging, elevated soil salinity, increased exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, limited availability of phosphorous nutrients or avoidance of shade.
  • Plants and plant varieties which can also be treated according to the invention are those plants which are characterized by increased yield properties.
  • An increased yield can in these plants z. These include improved plant physiology, improved plant growth and improved plant development, such as water utilization efficiency, water retention efficiency, improved nitrogen utilization, increased carbon assimilation, improved photosynthesis, enhanced germination power and accelerated maturation.
  • Yield can be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for hybrid seed production, seedling vigor, plant size, internode number and spacing, root growth, seed size, fruit size, Pod size, pod or ear number, number of seeds per pod or ear, seed mass, increased seed filling, reduced seed drop, reduced pod popping and stability.
  • Plants which can be treated according to the invention are hybrid plants which already express the properties of the heterosis or of the hybrid effect, which generally leads to a higher yield, higher growth. better health and better resistance to biotic and abiotic stress factors. Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner). The hybrid seed is typically harvested from the male sterile plants and sold to propagators.
  • Pollen sterile plants can sometimes be produced (eg in the case of maize) by means of removal (ie mechanical removal of the male genitalia or the male flowers); however, it is more common for male sterility to be due to genetic determinants in the plant genome.
  • the desired product as one wants to harvest from the hybrid plants, is the seeds, it is usually beneficial to ensure that the plant is fertile in hybrid plants that are responsible for the genetic susceptibility to male sterility Contain determinants, is completely restorated. This can be accomplished by ensuring that the male crossing partners possess appropriate fertility restorer genes capable of restoring pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility.
  • cytoplasmic pollen sterility have been described, for example, for Brassica species.
  • genetic determinants of male sterility may also be localized in the cell nucleus.
  • Pollen sterile plants can also be obtained using plant biotechnology methods such as genetic engineering.
  • a particularly convenient means of producing male-sterile plants is described in WO 89/10396, wherein, for example, a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens. The fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells.
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering which can be treated according to the invention are herbicide-tolerant plants, i. H. Plants tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation conferring such herbicide tolerance.
  • Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, ie plants that have been tolerated to the herbicide glyphosate or its salts.
  • glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS).
  • EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
  • EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
  • EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium, the CP4 gene of the bacterium Agrobacterium sp., The genes for a EPSPS from the petunia, for a EPSPS from the tomato or for a Encoding EPSPS from Eleusine.
  • Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate oxidoreductase enzyme. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme. Glyphosate-tolerant plants can also be obtained by selecting plants which select naturally occurring mutations of the above mentioned genes. Other herbicide-resistant plants are, for example, plants which have been tolerated to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate.
  • Such plants can be obtained by expressing an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition.
  • an effective detoxifying enzyme is, for example, an enzyme encoding a phosphinotricin acetyltransferase (such as the bar or pat protein from Streptomyces species). Plants expressing an exogenous phosphitricin acetyltransferase have been described.
  • hydroxyphenylpyruvate dioxygenase HPPD
  • the hydroxyphenyl pyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate.
  • Plants tolerant of HPPD inhibitors may be transformed with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding an imitated HPPD enzyme.
  • Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor.
  • the tolerance of plants to HPPD inhibitors can also be improved by transforming plants with a gene encoding a prephenate dehydrogenase enzyme in addition to a gene encoding an HPPD-tolerant enzyme.
  • ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides.
  • ALS also known as acetohydroxy acid synthase, AHAS
  • AHAS acetohydroxy acid synthase
  • plants tolerant to imidazolinone and / or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding.
  • Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering) which can also be treated according to the invention are insect-resistant transgenic plants, ie plants that have been made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such insect resistance.
  • insect-resistant transgenic plant includes any plant containing at least one transgene comprising a coding sequence encoding: 1) an insecticidal crystal protein from Bacillus thuringiensis or an insecticide part thereof, such as the insecticidal crystal proteins, which are available online at:
  • Bacillus thuringiensis crystal protein or a part thereof which is insecticidal in the presence of a second, different crystal protein from Bacillus thuringiensis or a part thereof, such as the binary toxin consisting of the crystal proteins Cy34 and Cy35; or
  • an insecticidal hybrid protein comprising parts of two different insecticidal crystal proteins from Bacillus thuringiensis, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g. The protein CrylA.105 produced by the corn event MON98034 (WO 2007/027777); or
  • VIPs vegetative insecticidal proteins
  • a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the binary toxin consisting of the proteins VIPlA and VIP2A.
  • a hybrid insecticidal protein comprising parts of various secreted proteins of Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins of 1) or a hybrid of the proteins of 2) above; or
  • 8) a protein according to any one of items 1) to 3) above, in which some, in particular 1 to 10, amino acids have been replaced by another amino acid in order to achieve a higher insecticidal activity against a target insect species and / or the spectrum of the corresponding To expand target insect species and / or due to changes induced in the coding DNA during cloning or transformation (preserving the coding for an insecticidal protein), such as the protein VIP3Aa in cotton event COT 102.
  • insect-resistant transgenic plants in the present context also include any plant comprising a combination of genes encoding the proteins of any of the above classes 1 to 8.
  • an insect-resistant plant contains more than one transgene that encodes a protein according to any one of the above-mentioned 1 to 8 in order to determine the spectrum of the corresponding or to delay the development of insect resistance to plants by employing various proteins that are insecticidal to the same species of target insect, but have a different mode of action, such as binding to different receptor binding sites in the insect.
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are tolerant to abiotic stressors.
  • Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such stress resistance.
  • Particularly useful plants with stress tolerance include the following: a. Plants which contain a transgene which is able to reduce the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or plants. b. Plants containing a stress tolerance promoting transgene capable of reducing the expression and / or activity of the PARG-encoding genes of the plants or plant cells; c.
  • Plants containing a stress tolerance enhancing transgene encoding a plant functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthetic pathway including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase.
  • Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering, which can also be treated according to the invention, have an altered amount, quality and / or shelf life of the harvested product and / or altered properties of certain components of the harvested product on, such as:
  • Transgenic plants which synthesize a modified starch with respect to their chemical-physical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the average chain length, the distribution of the side chains, the viscosity behavior, the gel strength, the starch grain size and / or starch morphology in comparison to the synthesized starch in wild-type plant cells or plants, so that this modified starch is better suited for certain applications.
  • chemical-physical properties in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the average chain length, the distribution of the side chains, the viscosity behavior, the gel strength, the starch grain size and / or starch morphology in comparison to the synthesized starch in wild-type plant cells or plants, so that this modified starch is better suited for certain applications.
  • Levantyps plants that produce alpha-1,4-glucans, plants that produce alpha-1,6-branched alpha-l, 4-glucans, and plants that produce alternan.
  • Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering), which can also be treated according to the invention, are plants such as cotton plants with altered fiber properties. Such plants can be genetically transformed or by selection of plants containing a mutation conferring such altered fiber properties; These include: a) plants such as cotton plants containing an altered form of cellulose synthase genes; b) plants such as cotton plants containing an altered form of rsw2 or rsw3 homologous nucleic acids;
  • plants such as cotton plants having increased expression of sucrose phosphate synthase
  • plants such as cotton plants with increased expression of sucrose synthase
  • plants such as cotton plants with modified reactivity fibers, e.g. By expression of the N-acetylglucosamine transferase gene, including nodC, and chitin synthase genes.
  • Plants or plant varieties which can also be treated according to the invention are plants such as oilseed rape or related Brassica plants with altered oil composition properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; These include: a) plants, such as rape plants, that produce oil with a high oleic acid content;
  • plants such as oilseed rape plants, which produce oil with a low linolenic acid content.
  • plants such as rape plants that produce oil with a low saturated fatty acid content.
  • transgenic plants which can be treated according to the invention are plants with one or more genes coding for one or more toxins, the transgenic plants offered under the following commercial names: YIELD GARD® (for example maize, cotton, Soybeans), KnockOut® (for example corn), BiteGard® (for example maize), BT-Xtra® (for example corn), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn), Protecta® and NewLeaf® (potato).
  • YIELD GARD® for example maize, cotton, Soybeans
  • KnockOut® for example corn
  • BiteGard® for example maize
  • BT-Xtra® for example corn
  • StarLink® for example maize
  • Bollgard® cotton
  • Nucotn® cotton
  • Nucotn 33B® cotton
  • NatureGard® for example corn
  • Protecta® and NewLeaf® pot
  • Herbicide tolerant crops to be mentioned include, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready® (glyphosate tolerance, for example corn, cotton, soybean), Liberty Link® (phosphinotricin tolerance, for example Rapeseed), IMI® (imidazolinone tolerance) and SCS® (Sylfonylurea tolerance), for example maize.
  • Herbicide-resistant plants plants traditionally grown for herbicide tolerance) to be mentioned include the varieties sold under the name Clearfield® (for example corn).
  • transgenic plants which can be treated according to the invention are plants which contain transformation events, or a combination of transformation events, and which, for example, Games are listed in the files of various national or regional authorities (see for example http://gmoinfo.jrc.it/gmp_browse.aspx and http://www.agbios.com/dbase.php).
  • the active compounds or compositions according to the invention can also be used in the protection of materials for the protection of industrial materials against attack and destruction by undesired microorganisms, such as e.g. Mushrooms and insects, are used.
  • the compounds according to the invention can be used alone or in combinations with other active substances as antifouling agents.
  • Technical materials as used herein mean non-living materials that have been prepared for use in the art.
  • technical materials to be protected from microbial alteration or destruction by the active compounds of the present invention may be adhesives, glues, paper, wallboard and board, textiles, carpets, leather, wood, paints and plastics, coolants, and other materials infested by microorganisms or can be decomposed.
  • parts of production plants and buildings e.g. Cooling water circuits, cooling and heating systems and ventilation and air conditioning systems, which may be affected by the proliferation of microorganisms.
  • technical materials which may be mentioned are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood.
  • the active compounds or compositions according to the invention can prevent adverse effects such as decay, deterioration, decomposition, discoloration or mold.
  • the compounds of the invention for protection against fouling of objects in particular of hulls, screens, nets, structures, quays and signal systems, which come in contact with seawater or brackish water, can be used.
  • the inventive method for controlling unwanted fungi can also be used for the protection of so-called storage goods.
  • Storage Goods are understood natural substances of plant or animal origin or their processing products, which were taken from nature and for long-term protection is desired
  • Storage goods of plant origin such as plants or plant parts, such as stems, leaves, tubers, seeds , Fruits, grains, can be protected in freshly harvested condition or after processing by (pre-) drying, wetting, crushing, grinding, pressing or roasting.
  • Storage goods also includes lumber, whether unprocessed, such as lumber, power poles and barriers, or in the form of finished products, such as furniture, storage goods of animal origin are, for example, skins, leather, furs and hair.
  • the active compounds according to the invention can prevent disadvantageous effects such as decay, deterioration, disintegration, discoloration or mold.
  • Bremia species such as Bremia lactucae
  • Peronospora species such as Peronospora pisi or P. brassicae
  • Phytophthora species such as Phytophthora infestans
  • Plasmopara species such as Plasmopara viticola
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis
  • Pythium species such as Pythium ultimum
  • Phaeosphaeria species such as Phaeosphaeria nodorum
  • Pyrenophora species such as, for example, Pyrenophora teres
  • Ramularia species such as Ramularia collo-cygni
  • Rhynchosporium species such as Rhynchosporium secalis
  • Septoria species such as Septoria apii
  • Typhula species such as Typhula incarnata
  • Venturia species such as Venturia inaequalis
  • Ear and panicle diseases caused by e.g. Alternaria species, such as Alternaria spp .; Aspergillus species, such as Aspergillus fiavus; Cladosporium species, such as Cladosporium cladosporioides; Claviceps species, such as Claviceps purpurea; Fusarium species such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Monographella species, such as Monographella nivalis; Septoria species such as Septoria nodorum;
  • Alternaria species such as Alternaria spp .
  • Aspergillus species such as Aspergillus fiavus
  • Cladosporium species such as Cladosporium cladosporioides
  • Claviceps species such as Claviceps purpurea
  • Fusarium species such as Fusarium culmorum
  • Gibberella species such as Gib
  • Sphacelotheca species such as Sphace- lotheca reiliana
  • Tilletia species such as Tületia caries, T. controversa
  • Urocystis species such as For example, Urocystis occulta
  • Ustilago species such as Ustilago nuda, U. nuda tritici
  • Verticilium species such as Verticilium alboatrum
  • Nectria species such as Nectria galligena
  • Botrytis species such as Botrytis cinerea
  • Rhizoctonia species such as Rhizoctonia solani
  • Helminthosporium species such as Helminthosporium solani
  • Xanthomonas species such as Xanthomonas campestris pv. Oryzae
  • Pseudomonas species such as Pseudomonas syringae pv. Lachrymans
  • Erwinia species such as Erwinia amylovora
  • the following diseases of soybean beans can be controlled: fungal diseases on leaves, stems, pods and seeds caused by, for example, Alternaria leaf spot (Alternaria sp. Ater tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var.
  • Phytophthora Red (Phytophthora megasperma), Brown Star Red (Phialophora gregata), Pythium Red (Pythium aphanidertnatum, Pythium irregular, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Red, Star Decay, and Damping Off (Rhizoctonia solani), Sclerotinia Stem Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Red (Thielaviopsis basicola).
  • microorganisms that can cause degradation or a change in the technical materials, for example, bacteria, fungi, yeasts, algae and mucus organisms may be mentioned.
  • the active compounds according to the invention preferably act against fungi, in particular molds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • microorganisms of the following genera Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, like Chaetomium globosum; Coniophora, such as Coniophora pentana; Lentinus, like Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; Escherichia, like Escherichia coli; Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus.
  • Alternaria such as Alternaria tenuis
  • Aspergillus such as Asper
  • the active compounds according to the invention also have very good antifungal effects. They have a very broad antimycotic spectrum of activity, in particular against dermatophytes and yeasts, mold and diphasic fungi (eg against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, microsporon species such as Microsporon canis and audouinii.
  • Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum Aspergillus species such as Aspergillus niger and Aspergillus fumigatus
  • Trichophyton species such as Trichophyton mentagrophytes
  • microsporon species such as Microsporon canis and audouinii.
  • the list of these fungi is by no means a limitation of the detect
  • the active compounds according to the invention can therefore be used in both medical and non-medical applications.
  • the application rates can be varied within a relatively wide range, depending on the mode of administration.
  • the application rate of the erf ⁇ ndungsgemas active ingredients is
  • Leaves from 0.1 to 10000 g / ha, preferably from 10 to 1000 g / ha, more preferably from 50 to 300 g / ha (when used by pouring or
  • Drops can even reduce the rate of application, especially if inert substrates such as rockwool or perlite are used);
  • seed treatment from 2 to 200 g per 100 kg of seed, preferably from 3 to 150 g per 100 kg of seed, more preferably from 2.5 to 25 g per 100 kg of seed, most preferably from 2.5 to 12.5 g per 100 kg of seed;
  • the active compounds or compositions according to the invention can therefore be used to protect plants within a certain period of time after the treatment against attack by the mentioned pathogens.
  • the period of time within which protection is afforded generally ranges from 1 to 28 days, preferably from 1 to 14 days, more preferably from 1 to 10 days, most preferably from 1 to 7 days after treatment of the plants with the active ingredients or up to 200 days after seed treatment.
  • mycotoxins include: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2 and HT2 toxin, fumonisins, zearalenone, moniliformin, fusarin, diaceotoxyscirpenol (DAS) , Beauvericin, enniatine, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins, which may be caused, for example, by the following fungi: Fusarium spec., Such as Fusarium acatumum, F.
  • the compounds according to the invention may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including antiproliferative agents) or as agents MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism) are used. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • the active compounds according to the invention intervene in the metabolism of the plants and can therefore also be used as growth regulators.
  • Plant growth regulators can exert various effects on plants.
  • the effects of the substances depend essentially on the time of application, based on the stage of development of the plant and on the amounts of active substance applied to the plants or their surroundings and on the mode of administration. In any case, growth regulators should influence the crop plants in a specific way.
  • Plant growth-regulating substances can be used, for example, for inhibiting the vegetative growth of the plants. Such growth inhibition is of economic interest among grasses, among other things, because this can reduce the frequency of grass clippings in ornamental gardens, parks and sports facilities, on roadsides, at airports or in orchards. Also of importance is the inhibition of the growth of herbaceous and woody plants on roadsides and near pelines or overland pipelines or, more generally, in areas where a high rate of plant growth is undesirable.
  • growth regulators to inhibit grain elongation. This reduces or completely eliminates the risk of crop stagnation before harvesting, and crop growth regulators can produce a straw boost that also counteracts storage, and the use of growth regulators for crop shortening and stalk augmentation allows for higher fertilizer levels to increase the yield without the risk of storing the grain.
  • An inhibition of vegetative growth enables a denser planting in many crops, so that multi-carrier can be achieved based on the soil surface.
  • An advantage of the smaller plants thus obtained is that the culture can be more easily processed and harvested.
  • An inhibition of the vegetative growth of the plants can also lead to increased yields that the nutrients and assimilates benefit the flower and fruit formation to a greater extent than the vegetative plant parts.
  • Growth regulators can often be used to promote vegetative growth. This is of great benefit when harvesting the vegetative plant parts. Promoting vegetative growth can, however, simultaneously promote generative growth by producing more assimilates so that more or more fruits are produced.
  • Yield increases can in some cases be achieved through an intervention in the plant metabolism, without any noticeable changes in vegetative growth.
  • growth regulators a change in the composition of the plants can be achieved, which in turn can lead to an improvement in the quality of the harvested products.
  • the degradation of desired contents substances such.
  • Sugar in sugar beet or cane with growth regulators before or after harvesting.
  • the production or the discharge of secondary plant ingredients can be positively influenced.
  • An example is the stimulation of latex flow in gum trees.
  • parthenocarp fruits may develop. Furthermore, the sex of the flowers can be influenced. Also, a sterility of the pollen can be produced, which has a great importance in the breeding and production of hybrid seed.
  • the branching of the plants can be controlled.
  • the development of side shoots can be promoted by breaking the apicoid dominance, which can be very desirable, especially in ornamental plant cultivation, also in connection with growth inhibition.
  • the foliage of the plants can be controlled so that a defoliation of the plants is achieved at a desired time.
  • Such defoliation plays a major role in the mechanical harvesting of cotton but is also of interest in other crops such as in viticulture to facilitate the harvest. Defoliation of the plants may also be done to reduce the transpiration of the plants before transplanting.
  • growth regulators can also accelerate or delay the maturity of Emtegutes reach before or after harvest. This is of particular advantage because this can bring about an optimal adaptation to the needs of the market.
  • growth regulators may in some cases improve fruit colouration.
  • a temporal concentration of maturity can be achieved. This creates the conditions for e.g. in the case of tobacco, tomatoes or coffee a complete mechanical or manual harvesting can be carried out in one operation.
  • growth regulators it is also possible to influence the seed or bud rest of the plants so that the plants, such as e.g. Pineapples or ornamental plants in nurseries to germinate, sprout or flower at a time when they normally do not show any willingness to do so.
  • Delaying bud sprouting or seed germination using growth regulators may be desirable in areas prone to frost to prevent damage from late frosts.
  • growth regulators can induce plant resistance to frost, dryness or high soil salinity. This makes it possible to cultivate plants in areas that are normally unsuitable for this purpose.
  • the plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) the agents according to the invention.
  • the preferred ranges given above for the active compounds or agents also apply to the treatment of these plants. Particularly emphasized is the plant treatment with the compounds or agents specifically mentioned in the present text.
  • reaction mixture is then concentrated under reduced pressure and the residue is treated with saturated aqueous sodium chloride solution and ethyl acetate.
  • organic phase is separated, dried over sodium sulfate, filtered and concentrated. This gives 0.70 g (99%) of the desired product, which is reacted without further purification.
  • Example A Sphaerotheca test (cucumber) / protective
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • young cucumber plants are sprayed with the preparation of active compound in the stated application rate.
  • the plants are inoculated with a spore suspension of Sphaerothecafiiliginea.
  • the plants are placed in a greenhouse at 70% relative humidity and a temperature of 23 ° C. 7 days after the inoculation the evaluation takes place.
  • 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.
  • Example B Leptosphaeria nodorum test (wheat) / protective
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • young wheat plants are sprayed with the preparation of active compound in the stated application rate.
  • the plants are inoculated with an aqueous spore suspension of Leptosphaeria nodorum and then left for 48 h at 100% relative humidity and 22 ° C.
  • the plants are then placed in a greenhouse at 90% relative humidity and a temperature of 22 ° C.
  • the evaluation takes place 7-9 days after the inoculation. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.
  • Example C Alternaria test (tomato) / protective
  • Emulsifier 1 part by weight of alkyl-aryl-polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Alternaria solani. The plants are then placed in an incubation booth at about 20 ° C and 100% relative humidity. 3 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.
  • the further compounds 2, 3, 10, 9, 23, 22, 12, 33, and 37 according to the invention show an efficiency of 70% or more.
  • Example D Pyrenophora teres test (barley) / protective
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Example E Venturia test (apple) / protective
  • Emulsifier 1 part by weight of alkyl-aryl-polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are nokuliert with an aqueous conidia suspension of the apple scab Venturia inaequalis and then remain i- 1 day at about 20 0 C and 100% relative humidity in an incubation cabinet. The plants are then placed in the greenhouse at about 21 0 C and a relative humidity of about 90%. 10 days after the inoculation the evaluation takes place.
  • 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.
  • the following compounds 1, 2, 3, 9, 10, 11, 12, 22, 23 and 37 according to the invention show an efficacy of 70% or more at an active ingredient concentration of 100 ppm.
  • Example F Blumeria graminis test (barley) / protective
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried, the plants are planted with spores of Blumeria graminis f.sp. hordei pollinated. The plants are placed in a greenhouse at a temperature of about 18 ° C and a relative humidity of about 80% to promote the development of mildew pustules. 7 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.
  • Example G Puccinia triticina test (wheat) / protective
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are sprayed with spores with a spore suspension of Puccinia triticina. The plants remain 48 hours at 20 0 C and 100% relative humidity in an incubation cabin. The plants are placed in a greenhouse at a temperature of about 2O 0 C and a relative humidity of about 80%. 8 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.
  • Example H Production of fumonisin FB1 by Fusarium proliferatum
  • the plate was incubated at high humidity for 5 days at 20 ° C. At the beginning and after 5 days, an OD measurement was made at OD620 (multiple measurement: 3 x 3 measurements per hole) to calculate growth inhibition. After 5 days, a sample of the liquid medium was removed and diluted 1: 1000 in 50% acetonitrile. The concentration of FB1 of the diluted samples was analyzed by HPLC-MS / MS and the measurements used to calculate the inhibition of fumonisin FB1 production compared to a drug-free control.
  • HPLC column Waters Atlantis T3 (trifunctional C18 bond, sealed)
  • Solvent A water + 0.1% HCOOH (v / v)
  • Solvent B acetonitrile + 0.1% HCOOH (v / v)
  • Examples Nos. 1, 3, 9, 10, 11, 12, 13, 21, 22, 23 and 32 showed activity> 80% in the inhibition of fumonisin FB1 production at a concentration of 50 ⁇ M.
  • the inhibition of the growth of Fusarium proliferatum of the examples mentioned varied from 36 to 100% at 50 ⁇ M.
  • Example I Production of DON / acetyl-DON by Fusarium graminearum
  • the compounds were (in microtiter plates inducing in a DON liquid medium 1 g (NH 4) 2 HPO 4, 0.2 g MgSO 4 x 7 H 2 O, 3 g KH 2 PO 4, 10 g glycerol, 5 g NaCl, and 40 g of sucrose per liter) and DMSO (0.5%).
  • the inoculation was carried out with a concentrated spore suspension of Fusarium graminearum at a final concentration of 2000 spores / ml.
  • the plate was incubated at high humidity for 7 days at 28 ° C. At the beginning and after 3 days, an OD measurement at OD620 (multiple measurement: 3 ⁇ 3 measurements per hole) was made to calculate the growth inhibition.
  • HPLC column Waters Atlantis T3 (trifunctional C18 bond, sealed)
  • Solvent A water / 2.5 mM NH 4 OAc + 0.05% CH 3 COOH (v / v)
  • Solvent B methanol / 2.5mM NH 4 OAc + 0.05% CH 3 COOH (v / v)
  • Examples Nos. 1, 3, 9, 10, 11, 12, 21, 22 and 32 showed> 80% activity in inhibiting DON / AcDON production at 50 ⁇ M.
  • the inhibition of the growth of Fusarium graminearum of the examples mentioned varied from 34 to 99% at 50 ⁇ M.
  • Example J Production of Aflatoxins by Aspergillus parasiticus
  • the compounds were grown in microtiter plates (black 96-well plates with flat and transparent bottom) in an aflatoxin-inducing liquid medium (20 g sucrose, 4 g yeast extract, 1 g KH 2 PO 4 and 0.5 g MgSO 4 .7H 2 O per Liter) with 20 mM Cavasol (hydroxypropyl-beta-cyclodextrin) and 1% DMSO.
  • the inoculation was carried out with a concentrated spore suspension of Aspergillus parasiticus at a final concentration of 1000 spores / ml.
  • the plate was incubated at high humidity for 7 days at 20 0 C.
  • Examples Nos. 11 and 32 showed activity> 80% inhibition of aflatoxin production at 50 ⁇ M.
  • the growth inhibition of Aspergillus parasiticus at 50 ⁇ M by these examples varied in the range of 43 to 69%.
  • Example K Phytoregulatory effect in pre- and postemergence Phvtoregulatory effect in pre-emergence
  • test plants are placed in sandy loam soil in wood fiber pots, covered with soil and grown in the greenhouse under good growth conditions. 2-3 weeks after sowing, the test plants are treated in the single leaf stage.
  • the test compounds formulated as wettable powders (WP) are sprayed onto the green plant parts in various dosages with a water application rate of approximately 600 L / ha with the addition of 0.2% wetting agent.
  • WP wettable powders

Abstract

La présente invention concerne de nouveaux dérivés de phényl(oxy/thio)alcanol, un procédé pour préparer ces composés, des matières contenant ces composés et leur utilisation en tant que composés biologiquement actifs, notamment pour lutter contre des micro-organismes nocifs dans le cadre de la protection végétale et de la protection de la matière et en tant que régulateurs de la croissance végétale.
EP10729808A 2009-07-08 2010-06-25 Dérivés de phényl(oxy/thio)alcanol Withdrawn EP2451784A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP10729808A EP2451784A1 (fr) 2009-07-08 2010-06-25 Dérivés de phényl(oxy/thio)alcanol

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP09164928 2009-07-08
EP10729808A EP2451784A1 (fr) 2009-07-08 2010-06-25 Dérivés de phényl(oxy/thio)alcanol
PCT/EP2010/003908 WO2011003527A1 (fr) 2009-07-08 2010-06-25 Dérivés de phényl(oxy/thio)alcanol

Publications (1)

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EP2451784A1 true EP2451784A1 (fr) 2012-05-16

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US (2) US9051277B2 (fr)
EP (1) EP2451784A1 (fr)
JP (2) JP5792163B2 (fr)
KR (1) KR20120046235A (fr)
CN (2) CN102471286B (fr)
AR (1) AR079093A1 (fr)
AU (1) AU2010268837B2 (fr)
BR (1) BR112012000245A8 (fr)
CA (1) CA2767385A1 (fr)
CL (1) CL2012000017A1 (fr)
CO (1) CO6612220A2 (fr)
EA (2) EA021808B1 (fr)
EC (1) ECSP12011575A (fr)
MX (1) MX2012000279A (fr)
TW (1) TWI519522B (fr)
WO (1) WO2011003527A1 (fr)

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KR20120046242A (ko) * 2009-07-08 2012-05-09 바이엘 크롭사이언스 아게 치환된 페닐(옥시/티오)알칸올 유도체
AU2010268837B2 (en) * 2009-07-08 2015-09-10 Bayer Intellectual Property Gmbh Phenyl(oxy/thio)alkanol derivatives
RU2767635C1 (ru) * 2021-06-29 2022-03-18 Федеральное государственное бюджетное образовательное учреждение высшего образования "Московский государственный университет имени М.В. Ломоносова" (МГУ) Комплексный препарат для предпосевной обработки семян яровой пшеницы на основе гиббереллинов, полиэтиленгликоля и фруктозы
CN116063226B (zh) * 2023-03-15 2023-06-02 云南省农业科学院茶叶研究所 含单萜酚结构的醚类化合物

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JP2012532156A (ja) 2012-12-13
MX2012000279A (es) 2012-01-27
CL2012000017A1 (es) 2012-10-12
EA201590002A1 (ru) 2015-04-30
KR20120046235A (ko) 2012-05-09
CN104262272A (zh) 2015-01-07
US20110039865A1 (en) 2011-02-17
ECSP12011575A (es) 2012-02-29
AU2010268837A1 (en) 2012-02-02
CO6612220A2 (es) 2013-02-01
US9051277B2 (en) 2015-06-09
WO2011003527A1 (fr) 2011-01-13
US9321732B2 (en) 2016-04-26
BR112012000245A8 (pt) 2016-06-21
JP2015187120A (ja) 2015-10-29
EA201270136A1 (ru) 2012-07-30
JP5792163B2 (ja) 2015-10-07
TW201110883A (en) 2011-04-01
BR112012000245A2 (pt) 2015-10-06
CA2767385A1 (fr) 2011-01-13
US20140357649A1 (en) 2014-12-04
AR079093A1 (es) 2011-12-28
CN102471286A (zh) 2012-05-23
AU2010268837B2 (en) 2015-09-10
EA021808B1 (ru) 2015-09-30
TWI519522B (zh) 2016-02-01

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