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WO2022129190A1 - 1,2,4-oxadiazoles substitués par (hétéro)aryle utilisés comme fongicides - Google Patents

1,2,4-oxadiazoles substitués par (hétéro)aryle utilisés comme fongicides Download PDF

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Publication number
WO2022129190A1
WO2022129190A1 PCT/EP2021/085926 EP2021085926W WO2022129190A1 WO 2022129190 A1 WO2022129190 A1 WO 2022129190A1 EP 2021085926 W EP2021085926 W EP 2021085926W WO 2022129190 A1 WO2022129190 A1 WO 2022129190A1
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alkyl
compound
formula
group
alkoxy
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PCT/EP2021/085926
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English (en)
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Anne-Sophie Rebstock
Jeremy Dufour
Aurelie MALLINGER
Jacopo NEGRONI
Vincent Thomas
Sophie DUCERF
Christoph Andreas Braun
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Bayer Aktiengesellschaft
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Publication of WO2022129190A1 publication Critical patent/WO2022129190A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to the use of (hetero)aryl substituted 1,2,4-oxadiazole compounds for controlling harmful microorganisms, in particular phytopathogenic fungi, in crop protection. It also relates to novel (hetero)aryl substituted 1,2,4-oxadiazole compounds and compositions comprising thereof.
  • Hetero aryl substituted 5-trifluoromethyl oxadiazole compounds which may be useful as HDAC4 inhibitors for treating human diseases are known from WO 2013/080120 and WO 2017/222951.
  • (hetero)aryl substituted 5-trifluoromethyl oxadiazole compounds may also be useful as crop protection agents to combat or prevent microorganisms’ infestations, such as phytopathogenic fungi (WO2019/122323, WO2018/187553, WO2017/110862 and WO2017/111152).
  • fungicidal agents Numerous fungicidal agents have been developed until now. However, the need remains for the development of further fungicidal compounds, so as to provide compounds being effective against a broad spectrum of fungi, having lower toxicity, higher selectivity, being used at lower dosage rate to reduce or avoid unfavorable environmental or toxicological effects whilst still allowing effective pest control. It may also be desired to identify further fungicidal compounds to prevent the emergence of fungicides resistances. Furthermore, it may be desired to provide further fungicidal compounds having an improved storage stability and/or a higher weather stability, for example an improved photostability.
  • the present invention provides a new use of (hetero)aryl substituted 1,2,4-oxadiazole compounds for controlling phytopathogenic fungi in crop protection, which has advantages over known uses of fungicidal compounds in at least some of these aspects.
  • the present invention relates to the use of compounds of formula (I) for controlling harmful microorganisms, in particular phytopathogenic fungi, in crop protection: wherein Cy, X, A 1 , A 2 , A 3 , R 1 , R 2 , R 3 , R 4 , R 5 , n and m are as described herein, as well as their salts, N- oxides and solvates.
  • the present invention also relates to some compounds of the formula (I) as defined herein, as well as their salts, N-oxides and solvates, and to a composition comprising thereof in a fungicidally effective amount.
  • the present invention relates to a method for controlling phytopathogenic fungi which comprises the step of applying at least one compound of formula (I) as defined herein or a composition as defined herein to the plants, plant parts, seeds, fruits or to the soil in which the plants grow.
  • halogen refers to fluorine, chlorine, bromine or iodine atom.
  • Ci-Cs-alkyl refers to a saturated, branched or straight hydrocarbon chain having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms.
  • said hydrocarbon chain has 1, 2, 3, 4, 5 or 6 carbon atoms (“Ci-Cg-alkyl”), in particular 1, 2, 3 or 4 carbon atoms (“Ci-C4-alkyl”).
  • Ci- Cs-alkyl examples include but are not limited to Ci-Cg-alkyl groups such as methyl, ethyl, propyl (n-propyl), 1- methylethyl (iso-propyl), butyl (n-butyl), 1 -methylpropyl (sec-butyl), 2-methylpropyl (iso-butyl), 1,1- dimethylethyl (tert-butyl), pentyl, 1 -methylbutyl, 2-methylbutyl, 3 -methylbutyl, 2,2-dimethylpropyl, 1- ethylpropyl, 1,1 -dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1 -methylpentyl, 2-methylpentyl, 3- methylpentyl, 4-methylpentyl, 1,1 -dimethylbutyl, 1,2-dimethylbutyl, 1,3 -dimethylbutyl, 2,2- dimethylbuty
  • C2-C8-alkenyl refers to an unsaturated, branched or straight hydrocarbon chain having 2, 3, 4, 5, 6, 7 or 8 carbon atoms and comprising at least one double bond.
  • said hydrocarbon chain has 2, 3, 4, 5 or 6 carbon atoms (“C2-Cg-alkenyl”), in particular 2, 3 or 4 carbon atoms (“C2-C4-alkenyl”).
  • C2-C8-alkenyl examples include but are not limited to C2-C4 -alkenyl groups such as ethenyl (or "vinyl"), prop-2-en-l-yl (or “allyl”), prop-l-en-l-yl, but-3-enyl, but-2-enyl, but-1- enyl, prop-l-en-2-yl (or “isopropenyl”), 2-methylprop-2-enyl, l-methylprop-2-enyl, 2-methylprop-l- enyl, 1-methylprop-l-enyl and buta- 1,3 -dienyl.
  • C2-C4 -alkenyl groups such as ethenyl (or "vinyl"), prop-2-en-l-yl (or “allyl”), prop-l-en-l-yl, but-3-enyl, but-2-enyl, but-1- enyl, prop-l-en-2-yl (or
  • C2-C8-alkynyl refers to a branched or straight hydrocarbon chain having 2, 3, 4, 5, 6, 7 or 8 carbon atoms and comprising at least one triple bond.
  • Examples of C2-C8-alkynyl include but are not limited to C2-C4-alkynyl groups such as ethynyl, prop-l-ynyl, prop-2-ynyl (or “propargyl”), but-l-ynyl, but-2-ynyl, but-3-ynyl or l-methylprop-2-ynyl group.
  • Ci-Cs-haloalkyl refers to a Ci-Cs-alk l group as defined above in which one or more hydrogen atoms are replaced with halogen atoms that may be the same or different. Typically, C’i-Cx-haloalkyl comprises up to 9 halogen atoms that can be the same or different. Analogously, the terms “Ci-Cg-haloalkyl” and “Ci-C4-haloalkyl” as used herein refer to corresponding groups that contain 1 to 6 or 1 to 4 carbon atoms.
  • C2-C8-haloalkenyl and “C2-C6-haloalkenyl” as used herein refer to a C2-C8-alkenyl or, respecitively, C2-C6 -alkenyl group as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.
  • C2-C8-haloalkenyl comprises up to 9 halogen atoms that can be the same or different.
  • C2-C8-haloalkynyl and “C2-C6-haloalkynyl” as used herein refer to a C2-C8-alkynyl or, respectively, C2-Cg-alkynyl group as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.
  • C2-C8-haloalkynyl comprises up to 9 halogen atoms that can be the same or different.
  • Ci-Cs-alkoxy refers to a group of formula (Ci-C8-alkyl)-O-, in which the term "Ci-Cs-alkyl” is as defined herein.
  • Ci-Cg-alkoxy and “Ci-C4-alkoxy” as used herein refer to corresponding groups containing a "Ci-Cg-alkyl” or "Ci-C4-alkyl” group as defined herein.
  • Ci-Cs-alkoxy examples include but are not limited to methoxy, ethoxy, n-propoxy, 1- methylethoxy, n-butoxy, 1 -methylpropoxy, 2-methylpropoxy, 1,1 -dimethylethoxy, n-pentoxy, 1- methylbutoxy, 2-methylbutoxy, 3 -methylbutoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, 1,1- dimethylpropoxy, 1,2-dimethylpropoxy, n-hexyloxy, 1 -methylpentoxy, 2-methylpentoxy, 3- methylpentoxy, 4-methylpentoxy, 1,1 -dimethylbutoxy, 1,2-dimethylbutoxy, 1,3 -dimethylbutoxy, 2,2- dimethylbutoxy, 2,3 -dimethylbutoxy, 3, 3 -dimethylbutoxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1,1,2- trimethylpropoxy, 1,2,2-trimethylpropoxy, 1 -e
  • Ci-Cs-haloalkoxy refers to a Ci-Cs-alkoxy group as defined above in which one or more hydrogen atoms are replaced with halogen atoms that may be the same or different.
  • Ci-Cg-haloalkoxy and “Ci-C4-haloalkoxy” as used herein refer to corresponding groups that contains 1 to 6 or 1 to 4 carbon atoms.
  • Ci-C4-haloalkoxy examples are chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1 -chloroethoxy, 1 -bromoethoxy, 1 -fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2- chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2, 2-dichloro-2 -fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1 -trifluoroprop-2 -oxy.
  • Ci-Cg-hydroxyalkyl refers to a Ci-Cg-alkyl group as defined above in which at least one hydrogen atom is replaced with a hydroxyl group.
  • Examples of Ci-Cg-hydroxyalkyl include but are not limited to Ci-C4-hydroxyalkyl groups such as hydroxymethyl, 1 -hydroxyethyl, 2- hydroxyethyl,l,2-dihydroxyethyl, 3 -hydroxypropyl, 2-hydroxypropyl, 1 -hydroxypropyl, 1 -hydroxy - propan-2-yl, 2-hydroxypropan-2-yl, 2,3 -dihydroxypropyl and l,3-dihydroxypropan-2-yl.
  • Ci-Cg-cyanoalkyl refers to a Ci-Cg-alkyl group as defined above in which at least one hydrogen atom is replaced with a cyano group.
  • Ci-Cs-alkylsulfanyl refers to a saturated, linear or branched group of formula (Ci-C8-alkyl)-S-, in which the term "Ci-Cs-alkyl” is as defined herein.
  • Examples of Ci-Cs-alkylsulfanyl include but are not limited to Ci-Cg-alkylsulfanyl groups such as methylsulfanyl, ethylsulfanyl, propylsulfanyl, isopropylsulfanyl, butylsulfanyl, scc-butylsulfanyl. isobutylsulfanyl, / -buty I sulfanyl, pentylsulfanyl, isopentylsulfanyl, hexylsulfanyl group.
  • Ci-Cs-haloalkylsulfanyl and “Ci-Cg-haloalkylsulfanyl” as used herein refer to a Ci-Cs- alkylsulfanyl or, respectively, Ci-Cg-alkylsulfanyl as defined above in which one or more hydrogen atoms are replaced with halogen atoms that may be the same or different.
  • Ci-Cs- alkylsulfinyl examples include but are not limited to saturated, straight-chain or branched alkylsulfinyl radicals having 1 to 6 (“Ci-Cg-alkylsulfinyl”) carbon atoms, for example (but not limited to) methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfmyl, butylsulfinyl, 1-methylpropylsulfmyl, 2- methylpropylsulfinyl, 1,1-dimethylethylsulfmyl, pentylsulfinyl, 1-methylbutylsulfmyl, 2- methylbutylsulfinyl, 3-methylbutylsulfmyl, 2,2-dimethylpropylsulfmyl, 1-ethylpropylsulfmyl, 1,1- dimethylpropylsulfin
  • Ci-Cs-haloalkylsulfinyl and “Ci-Cg-haloalkylsulfinyl” as used herein refer to a Ci-Cs- alkylsulfinyl or, respectively, Ci-Cg-alkylsulfinyl as defined above in which one or more hydrogen atoms are replaced with halogen atoms that may be the same or different.
  • Ci-Cs- alkylsulfonyl examples include but are not limited to Ci-Cg-alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1 -methylethylsulfonyl, butylsulfonyl, 1 -methylpropylsulfonyl, 2 -methyl - propylsulfonyl, 1,1 -dimethylethylsulfonyl, pentylsulfonyl, 1 -methylbutylsulfonyl, 2-methyl- butylsulfonyl, 3 -methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1 -ethylpropylsulfonyl, 1,1 -dimethylpropylsulfonyl, 1,2-dimethylpropylsulf
  • Ci-Cs-haloalkylsulfonyl and “Ci-Cg-haloalkylsulfonyl” as used herein refer to a Ci-Cs- alkylsulfonyl or, respectively, Ci-Cg-alkylsulfonyl as defined above in which one or more hydrogen atoms are replaced with halogen atoms that may be the same or different.
  • Ci-Cg -alkylsulfonylamino refer to a corresponding group that contains a Ci- Cg-alkyl group as defined herein.
  • Ci-Cs-haloalkylsulfonylamino and “Ci-Cg-haloalkylsulfonylamino” as used herein refer to a Ci-Cs-alkylsiilfonylamino or, respectively, Ci-Cg-alkylsulfonylamino as defined above in which one or more hydrogen atoms are replaced with halogen atoms that may be the same or different.
  • Ci-Cs-alkylsulfamoyl and “Ci-Cg-alkylsulfamoyl” as used herein refer to a sulfamoyl radical having one Ci-Cs-alkyl or, respectively, Ci-Cg-alkyl group as defined herein.
  • di-(Ci-C8-alkyl)sulfamoyl and “di-(Ci-Cg-alkyl)sulfamoyl” as used herein refer to a sulfamoyl radical having two independently selected Ci-Cs-alkyl or, respectively, Ci-Cg-alkyl groups as defined herein.
  • Ci-Cs-alkylcarbamoyl and “Ci-Cg-alkylcarbamoyl” as used herein refer to a carbamoyl radical having one Ci-Cs-alkyl or, respectively, Ci-Cg-alkyl group as defined herein.
  • di-(Ci-C8-alkyl)carbamoyl and “di-(Ci-C6-alkyl)carbamoyl” as used herein refer to a carbamoyl radical having two independently selected Ci-Cs-alk l or, respectively, Ci-Cg-alkyl groups as defined herein.
  • Ci- Cg-alkylcarbonyl refers to a corresponding group that contains a Ci-Cg-alkyl group as defined herein.
  • Ci-Cs-haloalkylcarbonyl and “Ci-Cg-haloalkylcarbonyl” as used herein refer to a Ci-Cs- alkylcarbonyl or, respectively, a Ci-Cg-alkylcarbonyl as defined above in which one or more hydrogen atoms are replaced with halogen atoms that may be the same or different.
  • Ci-Cg-haloalkylthiocarbonyl refers to a Ci-Cg-alkylthiocarbonyl as defined above in which one or more hydrogen atoms are replaced with halogen atoms that may be the same or different.
  • the terms “Ci-Cg-alkylcarbonyloxy” and “Ci-C4-alkylcarbonyloxy” as used herein refer to corresponding groups containing a Ci-Cg-alkyl or, respectively, Ci-C4-alkyl group.
  • Ci-Cs-haloalkylcarbonyloxy and “Ci-Cg-haloalkylcarbonyloxy” as used herein refer to a C i-Cs-alkylcarbonyloxy or, respectively, Ci-Cg -alkylcarbonyloxy as defined above in which one or more hydrogen atoms are replaced with halogen atoms that may be the same or different.
  • Ci-Cg-alkylcarbonylamino refers to a corresponding group containing a Ci-Cg- alkyl group.
  • Ci-Cs-haloalkylcarbonylamino and “Ci-Cg-haloalkylcarbonylamino” as used herein refer to a Ci-Cs-alkylcarbonylamino or, respectively, Ci-Cg-alkylcarbonylamino as defined above in which one or more hydrogen atoms are replaced with halogen atoms that may be the same or different.
  • the terms “Ci-Cg-alkoxycarbonyl” and “Ci-C4-alkoxycarbonyl” as used herein refer to a corresponding group containing a Ci-Cg-alkoxy or, respectively, Ci-C4-alkoxy group.
  • Ci-Cs-haloalkoxycarbonyl and “Ci-Cg-haloalkoxycarbonyl” as used herein refer to a Ci-Cs- alkoxycarbonyl or, respectively, Ci-Cg-alkoxy carbonyl as defined above in which one or more hydrogen atoms are replaced with halogen atoms that may be the same or different.
  • Ci-Cs-alkylamino and “Ci-Cg-alkylamino” as used herein refer to an amino radical having one Ci-Cx-alkyl or, respectively, Ci-Cg-alkyl group as defined herein.
  • Ci-Cg-alkylamino include but are not limited to A-mcthylamino. A-cthylamino. A-isopropylamino. A-n-propylamino. N- isopropylamino and /V-tert-butylamino.
  • di-(Ci-C8-alkyl)amino and “di-(Ci-Cg-alkyl)amino” as used herein refer to an amino radical having two independently selected Ci-Cs-alkyl or, respectively, Ci-Cg-alkyl groups as defined herein.
  • di-(Ci-C8-alkyl)amino include but are not limited to N, A-dimcthylamino. 'A-dicthyl- amino, N, A-diisopropylamino.
  • A-cthyl-A-mcthylamino A-mcthyl-A-n-propylamino. '-isopropyl-A-n- propylamino and A-tcrt-butyl-A-mcthylamino.
  • Cs-Cio-carbocyclyl refers to a non-aromatic, saturated or partially unsaturated, hydrocarbon ring system in which all of the ring members, which vary from 3 to 10, preferably 3 to 7 (“Cs-Cv-carbocyclyl”), are carbon atoms.
  • the ring system may be monocyclic or bicyclic (fused, spiro or bridged).
  • C-C’in-carbocycIcs include but are not limited to Cs-Cw-cycloalkyl (mono or bicyclic), CAC’io-cycloalkcnyl (mono or bicyclic), bicylic system comprising an aryl (e.g.
  • phenyl fused to a monocyclic C-Cg-cycloalkyl (e.g. tetrahydronaphthalenyl, indanyl) and bicylic system comprising an aryl (e.g. phenyl) fused to a monocyclic C-Cg-cycloalkcnyl (e.g. indenyl, dihydronaphthalenyl).
  • the Cs-Cw-carbocycle can be attached to the parent molecular moiety through any carbon atom.
  • Cs-Cio-cycloalkyl refers to a saturated, monovalent, mono- or bicylic hydrocarbon ring which contains 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms.
  • Cs-Cv-cycloalkyl designates monocyclic G-C’v-cycloalkyls which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
  • Cs-Cg-cycloalkyl designates monocyclic C -Cg-cycloalkyls which include cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • Examples of bicyclic Cg-Cio- cycloalkyls include but are not limited to bicyclo[3.1.1]heptane, bicyclo[2.2.1 ]heptane, bicyclo[2.2.2]octane, bicyclo[3.2.2]nonane, bicyclo[3.3.1]nonane, bicyclo[4.2.0]octyl, octahydro- pentalenyl and bicyclo[4.2.1 ]nonane.
  • Cs-Cv-halocycloalkyl refers to a Cs-C’v-cycloalkyl group as defined above in which one or more hydrogen atoms are replaced with halogen atoms that may be the same or different.
  • Cs-Cv-halocarbocyclyl refers to a C-CS-carbocyclyl group as defined above in which one or more hydrogen atoms are replaced with halogen atoms that may be the same or different.
  • aryl refers to an aromatic hydrocarbon ring system in which all of the ring members, which vary from 6 to 14, preferably from 6 to 10, are carbon atoms.
  • the ring system may be monocyclic or fused polycyclic (e.g. bicyclic or tricyclic). Examples of aryl include but are not limited to phenyl, azulenyl, naphthyl and fluorenyl.
  • the aryl can be attached to the parent molecular moiety through any carbon atom. It is further understood that when said aryl group is substituted with one or more substituents, said substituent(s) may be at any positions on said aryl ring(s). Particularly, in the case of aryl being a phenyl group, said substituent(s) may occupy one or both ortho positions, one or both meta positions, or the para position, or any combination of these positions.
  • 3- to 10-membered heterocyclyl refers to a non-aromatic, saturated or partially unsaturated non-aromatic ring system comprising 1 to 4, or 1 to 3 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur. If the ring system contains more than one oxygen atoms, they are not directly adjacent.
  • 3- to 10-membered heterocycles include but are not limited to 3- to 7-membered monocyclic non-aromatic heterocycles (“3- to 7-membered heterocyclyl”) and 6- to 10-membered polycyclic (e.g. bicyclic or tricyclic) non-aromatic heterocycles.
  • the 3- to 10- membered heterocyclyl can be connected to the parent molecular moiety through any carbon atom or nitrogen atom contained within the heterocycle.
  • heterocycle refers to a 3-, 4-, 5-, 6- or 7-membered monocyclic ring system containing 1, 2 or 3 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur where the ring system is saturated or unsaturated but not aromatic.
  • the heterocycle may comprise one to three nitrogen atoms, or one or two oxygen atoms, or one or two sulfur atoms, or one to three nitrogen atoms and one oxygen atom, or one to three nitrogen atoms and a sulfur atom or one sulfur atom and one oxygen atom.
  • saturated non- aromatic heterocycles include but are not limited to 3 -membered ring such as oxiranyl, aziridinyl, 4- membered ring such as azetidinyl, oxetanyl, thietanyl, 5 -membered ring such as tetrahydrofuranyl, 1,3- dioxolanyl, tetrahydrothienyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, triazolidinyl, isoxazolidinyl, oxazolidinyl, oxadiazolidinyl, thiazolidinyl, isothiazolidinyl, thiadiazolidinyl, 6-membered ring such as piperidinyl, hexahydropyridazinyl, hexahydropyrimidinyl, piperazinyl, triazinanyl, hexahydrotri
  • unsaturated non-aromatic hererocyles include but are not limited to 5 -membered ring such as dihydrofuranyl, 1,3-dioxolyl, dihydrothienyl, pyrrolinyl, dihydroimidazolyl, dihydropyrazolyl, isoxazolinyl, dihydrooxazolyl, dihydrothiazolyl or 6-membered ring such as pyranyl, thiopyranyl, thiazinyl and thiadiazinyl.
  • 5 -membered ring such as dihydrofuranyl, 1,3-dioxolyl, dihydrothienyl, pyrrolinyl, dihydroimidazolyl, dihydropyrazolyl, isoxazolinyl, dihydrooxazolyl, dihydrothiazolyl or 6-membered ring such as pyranyl, thiopyranyl, thiazinyl and
  • non-aromatic 6- to 10-membered polycyclic heterocycle refers to a 6-, 7-, 8-, 9-, 10-membered polycyclic (e.g. bicyclic or tricyclic) ring system containing 1, 2 or 3 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur where the ring system is saturated or unsaturated but not aromatic.
  • Non-aromatic bicyclic heterocycles may consist of a monocyclic heteroaryl as defined herein fused to a monocyclic Cs-Ck-cycloalkyl.
  • a monocyclic C3-C8- cycloalkenyl or a monocyclic non-aromatic heterocycle may consist of a monocyclic non-aromatic heterocycle fused either to an aryl (e.g. phenyl), a monocyclic Cs-Ck-cycloalkyl. a monocyclic C3-C8- cycloalkenyl or a monocyclic non-aromatic heterocycle.
  • nitrogen atom may be at the bridgehead (e.g.
  • Non-aromatic tricyclic heterocycles may consist of a monocyclic cycloalkyl connected through one common atom to a non-aromatic bicyclic heterocycle.
  • aromatic 5- to 14-membered heterocycle or “heteroaryl” as used herein refers to an aromatic ring system comprising 1 to 4 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur. If the ring system contains more than one oxygen atom, they are not directly adjacent.
  • Aromatic heterocycles include aromatic 5- or 6-membered monocyclic heterocycles and 6- to 14-membered polycyclic (e.g. bicyclic or tricyclic) aromatic heterocycles.
  • the 5- to 14-membered aromatic heterocycle can be connected to the parent molecular moiety through any carbon atom or nitrogen atom contained within the heterocycle.
  • aromatic 5- or 6-membered monocyclic heterocycle or just “5- or 6-membered heteroaryl” as used herein refers to a 5- or 6-membered monocyclic ring system containing 1, 2, 3 or 4 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur.
  • Examples of 5- membered monocyclic heteroaryl include but are not limited to furyl (furanyl), thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, isoxazolyl, oxazolyl, oxadiazolyl, oxatriazolyl, isothiazolyl, thiazolyl, thiadiazolyl and thiatriazolyl.
  • Examples of 6-membered monocyclic heteroaryl include but are not limited to pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl.
  • 6- to 14-membered polycyclic aromatic heterocycle or “polycyclic heteroaryl” as used herein refers to a 6-, 7-, 8-, 9-, 10-, 11-,12-, 13- or 14-membered polycyclic (e.g. bicyclic or tricyclic) ring system containing 1, 2 or 3 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur.
  • Aromatic bicyclic heterocycles may consist of a monocyclic heteroaryl as defined herein fused to an aryl (e.g. phenyl) or to a monocyclic heteroaryl.
  • bicyclic aromatic heterocycle examples include but are not limited to 9-membered ring such as indolyl, indolizinyl, isoindolyl, benzimadozolyl, imidazopyridinyl, indazolyl, benzotriazolyl, purinyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl and benzisoxazolyl or 10-membered ring such as quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, pteridinal and benzodioxinyl.
  • 9-membered ring such as indolyl, indolizinyl, isoindolyl, benzimadozolyl, imidazopyridinyl, indazolyl, benzotriazolyl,
  • nitrogen atom may be at the bridgehead (e.g. imidazo[l,2- a]pyridinyl, [l,2,4]triazolo[4,3-a]pyridinyl, imidazo[l,2-a]pyridinyl, imidazo[2,l-b]oxazolyl, furo[2,3- d]isoxazolyl).
  • Examples of tricyclic aromatic heterocyle include but are not limited to carbazolyl, acridinyl and phenazinyl.
  • aryl-Ci-Cg-alkyl designate a group of formula “-Ci-Cs-alkyl-R”, wherein R is respectively an aryl, 3- to 10-membered heterocyclyl, heteroaryl or G-CAcarbocyclyl as defined herein, "Ci-Cx-alkyl” is a saturated, branched or straight hydrocarbon chain having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms and wherein the group "-Ci-Cx-alkyl-R" is attached to the parent moiety via the ’’Ci-Cx-alkyl" group.
  • aryl-Ci-Cg-alkyl refers to corresponding groups of formula “-Ci-Cg-alkyl-R”.
  • aryl-Ci-Cg-haloalkyl refers to a group of formula “-Ci-Cg-haloalkyl-R”, wherein R is respectively an aryl, heteroaryl or C-C’io-carbocyclyl as defined herein, which is attached to the parent moiety via a Ci-Cg-haloalkyl linker, wherein “Ci-Cg-haloalkyl” is as defined herein.
  • substituents refers to a number of substituents that ranges from one to the maximum number of substituents possible based on the number of available bonding sites, provided that the conditions of stability and chemical feasibility are met.
  • leaving group as used herein is to be understood as meaning a group which is displaced from a compound in a substitution or an elimination reaction, for example a halogen atom, a trifluoromethanesulfonate (“triflate”) group, alkoxy, methanesulfonate, p-toluenesulfonate, etc.
  • the present invention relates to the use of a compound of formula (I) or a salt, N-oxide or solvate thereof for controlling harmful microorganisms, in particular phytopathogenic fungi, in crop protection: wherein
  • X is fluorine or chlorine
  • a 1 is N, CH or CF
  • a 2 is N, CH or CF
  • a 3 is N, CH or CF and m is 1 ;
  • a 3 is S and m is 0;
  • R 1 and R 2 are independently selected from the group consisting of hydrogen, cyano, C
  • Ci-Cs-alkyl, C2-C8-alkenyl and C2-C8-alkynyl may be substituted with one or more R a substituents and wherein said C3-C?-carbocyclyl, aryl, 3- to 10-membered-heterocyclyl and heteroaryl, in each case as such or as part of a composite substituent aryl-Ci-Cs-alkyl, 3- to 10-membered- hctcrocyclyl-Ci-Cs-alkyl. heteroaryl-Ci-Cs-alkyl or G-Cv-carbocyclyl-Ci-Cs-alkyl.
  • R 1 and R 2 may form, together with the carbon atom to which they are linked, a C’s-Cv-carbocyclyl or a 3- to 10-membered heterocyclyl, wherein said C’s-Cv-carbocyclyl or 3- to 10-membered heterocyclyl may be substituted with one or more R b substituents;
  • Cy is aryl, heteroaryl, G-C’in-carbocyclyl or 3- to 10-membered heterocyclyl; n is 0, 1, 2, 3 or 4;
  • R 3 is independently selected from the group consisting of halogen, cyano, hydroxyl, amino, nitro, carboxyl, sulfanyl, pcntafluoro-/ -sulfanyl. formyl, carbamoyl, carbamate, Ci-Cg-alkyl, Ci-Cg-cyanoalkyl, Ci-Cg-haloalkyl, C2-Cg-alkenyl, C2-Cg-haloalkenyl, C2-Cg-alkynyl, C2- Cg-haloalkynyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylsulfanyl, Ci-Cg- haloalkylsulfanyl, Ci-Cg-alkylsulfinyl, Ci-Cg-haloalkylsulfonyl, Ci-Cg- halo
  • Ci-Cg-alkyl, C2-Cg-alkenyl and C2-Cg-alkynyl may be substituted with one or more substituents independently selected from the group consisting of halogen, Ci-Cg-alkoxy and Ci-Cg-haloalkoxy; and wherein said Cs-C’v-carbocyclyl.
  • aryl and heteroaryl in each case as such or as part of the composite residues aryl-Ci-Cg-alkyl, heteroaryl-Ci-Cg-alkyl and Cs-CS-carbocyclyl-Ci-Cg- alkyl, may be substituted with one or more substituents independently selected from the group consisting of halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy and Ci-Cg- haloalkoxy;
  • R 4 is selected from the group consisting of hydrogen, hydroxy, formyl, Ci-Cg-alkyl, Ci-Cg- haloalkyl, C2-Cg-alkenyl, C2-Cg-haloalkenyl, C2-Cg-alkynyl, C2-Cg-haloalkynyl, Ci-Cg- alkylcarbonyl, Ci-Cg-haloalkylcarbonyl, Ci-Cg-alkylthiocarbonyl, Ci-Cg- haloalkylthiocarbonyl, Ci-Cg-alkoxycarbonyl, Ci-Cg-haloalkoxycarbonyl, Ci-Cg-alkoxy, Ci- Cg-haloalkoxy, Ci-Cg-alkylsulfonyl, Ci-Cg-haloalkylsulfonyl, phenylsulfonyl, C3-C10- carbocyclyl, 3- to 10-membered-hetero
  • aryl, 3- to 10-membered-heterocyclyl and heteroaryl in each case as such or as part of a composite substituent Cs-Cio-carbocyclyl-Ci-Cg-alkyl, C3-C10- carbocyclyl-Ci-Cg-haloalkyl, aryl-Ci-Cg-alkyl, aryl-Ci-Cg-haloalkyl, heteroaryl-Ci-Cg-alkyl or heteroaryl-Ci-Cg-haloalkyl, may be substituted with one or more substituents selected from the group consisting of halogen, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy and Ci-Cg-haloalkoxy;
  • R 5 is hydrogen, halogen or CN; each R a is independently selected from the group consisting of nitro, hydroxyl, cyano, carboxyl, amino, sulfanyl, pcntafluoro-/ -sulfanyl. formyl, carbamoyl, carbamate, Cs-CS-cycloalkyl. Cs-Cv-halocycloalkyl, Ci-Cs-alkylamino, di-(Ci-C8-alkyl)amino, Ci-Cs-alkoxy.
  • Ci-Cs- haloalkoxy Ci-Cs-alkylsulfanyl, Ci-Cx-haloalky 1 sulfanyl, Ci-Cs-alkylcarbonyl.
  • Ci-Cs- haloalkylcarbonyl Ci-Cs-alk lcarbamo l. di-(Ci-C8-alkyl)carbamoyl, Ci-Cs-alkoxycarbonyl, Ci-Cs-haloalkoxycarbonyl.
  • Ci-Cg-haloalkylcarbonylamino Ci-Cg- alkylsulfonylamino, Ci-Cg-haloalkylsulfonylamino, sulfamoyl, Ci-Cx-alkylsulfamoyl. di- Cj-C’x-alkylsulfamoyl.
  • aryl, aryl -Ci-Cg-alkyl and heteroaryl wherein said heteroaryl and said aryl, as such or as part of aryl-Ci-Cg-alkyl, are optionally substituted with one or more substituents independently selected from the group consisting of halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy and Ci-Cg-haloalkoxy.
  • the compounds of formula (I) are used for controlling harmful microorganisms, in particular phytopathogenic fungi, in crop protection.
  • the phytopathogenic fungi are selected from the group consisting of the Puccinia species, for example Puccinia recondita, Puccinia graminis or Puccinia striiformis,' the Uromyces species, for example Uromyces appendiculatus,' and the rust disease pathogens, in particular selected from the group consisting of the Gymnosporangium species, for example Gymnosporangium sabinae,' Hemileia species, for example Hemileia vastatrix, and Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae.
  • the rust disease pathogens in particular Phakopsora pachyrhizi and Phakopsora meibomiae.
  • the compound of formula (I) may be present in the form of different stereoisomers. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Accordingly, the invention encompasses both pure stereoisomers and any mixture of these isomers. Where a compound can be present in two or more tautomer forms in equilibrium, reference to the compound by means of one tautomeric description is to be considered to include all tautomer forms.
  • the compound of formula (I) may be present in the form of the free compound and/or a salt thereof, such as an agrochemically active salt.
  • Agrochemically active salts include acid addition salts of inorganic and organic acids well as salts of customary bases.
  • inorganic acids are hydrohalic acids, such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid, and acidic salts, such as sodium bisulfate and potassium bisulfate.
  • Useful organic acids include, for example, formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, saturated or mono- or diunsaturated fatty acids having 6 to 20 carbon atoms, alkylsulfuric monoesters, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylsulfonic acids or aryldisulfonic acids (aromatic radicals, such as phenyl and naphthyl, which bear one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic
  • Solvates of the compounds of formula (I) or their salts are stoichiometric compositions of the compounds with solvents.
  • N-oxides can be obtained in a simple manner by customary processes, for example by N-oxidation with hydrogen peroxide (H2O2), peracids, for example peroxy sulfuric acid or peroxy carboxylic acids, such as meta-chloroperoxybenzoic acid or peroxymonosulfuric acid (Caro's acid).
  • H2O2 hydrogen peroxide
  • peracids for example peroxy sulfuric acid or peroxy carboxylic acids, such as meta-chloroperoxybenzoic acid or peroxymonosulfuric acid (Caro's acid).
  • the corresponding N-oxides may be prepared starting from the respective compounds using conventional oxidation methods, e.g. by treating the compounds with an organic peracid such as metachloroperbenzoic acid (e.g. WO-A 2003/64572 or J. Med. Chem. 38 (11), 1892-1903, 1995); or with inorganic oxidizing agents such as hydrogen peroxide (e.g. J. Heterocyc. Chem. 18 (7), 1305-1308, 1981) or oxone (e.g. J. Am. Chem. Soc. 123 (25), 5962-5973, 2001).
  • the oxidation may lead to pure mono-N-oxides or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.
  • the compounds of formula (I) may exist in multiple crystalline and/or amorphous forms. Crystalline forms include unsolvated crystalline forms, solvates and hydrates.
  • X is fluorine
  • R 1 and R 2 are each independently selected from the group consisting of hydrogen, cyano, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkyl substituted with Ci-C4-alkoxy, Ci-C4-alkyl substituted with Ci-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, Cs-Cg-cycloalkyl and phenyl, wherein said phenyl may be substituted with one to three substituents selected from halogen, Ci-C4-alkyl, hydroxy and C
  • R 1 and R 2 may form, together with the carbon atom to which they are linked, a Cs-Cg-cycloalkyl or oxetanyl ring, wherein the Cs-Cg-cycloalkyl or oxetanyl ring may be substituted with one to three substituents selected from the group consisting of halogen, hydroxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylcarbonyloxy and Ci-C4-haloalkylcarbonyloxy.
  • R 1 is selected from the group consisting of hydrogen, cyano, methyl, ethyl, iso-propyl, n-propyl, n-butyl, iso-butyl, tert-butyl, hydroxymethyl, trifluoromethyl, difluoromethyl, ethenyl, ethynyl, phenyl, cyclopentyl, cyclobutyl and cyclopropyl, wherein the phenyl may be substituted with one or two halogen atoms, and
  • R 2 is selected from the group consisting of hydrogen, methyl, ethyl, trifluoromethyl and difluoromethyl, or
  • R 1 and R 2 may form, together with the carbon atom to which they are linked, a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or oxetanyl ring, wherein said ring is unsubstituted or substituted with one to three substituents selected from the group consisting of fluorine, hydroxy, methyl, ethyl, trifluoromethyl, methoxy and acetyloxy.
  • R 1 is selected from the group consisting of hydrogen, cyano, methyl, ethyl, iso-propyl, n-propyl, n-butyl, iso-butyl, tert-butyl, hydroxymethyl, trifluoromethyl, difluoromethyl, ethenyl, ethynyl, phenyl, cyclopentyl, cyclobutyl and cyclopropyl, wherein the phenyl may be substituted with one or two substituents selected from fluorine and chlorine, and
  • R 2 is hydrogen, or
  • R 1 and R 2 form, together with the carbon atom to which they are linked, a cyclopropyl, cyclobutyl or oxetanyl ring, more preferably a cyclopropyl or cyclobutyl ring.
  • each R 3 is independently selected from the group consisting of halogen, nitro, cyano, Ci-C4-alkyl, Cs-Cg-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and Ci-C4-alkoxycarbonyl.
  • each R 3 is independently selected from the group consisting of fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, iso-propyl, n-propyl, n-butyl, iso-butyl, tertbutyl, cyclopropyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, methoxycarbonyl, ethoxycarbonyl and tert-butoxycarbonyl, in particular selected from the group consisting of fluorine, chlorine, bromine, methyl and methoxy.
  • each R 3 is independently selected from fluorine and chlorine.
  • R 4 is selected from the group consisting of hydrogen, hydroxy, Ci-Cg- alkyl, Ci-Cg-alkylcarbonyl, Ci-Cg-haloalkylcarbonyl, Ci-Cg-alkoxy and Ci-Cg-haloalkoxy. More preferably R 4 is hydrogen.
  • R 5 is hydrogen or fluorine.
  • n 0, 1 or 2.
  • n 1 or 2.
  • n 0.
  • Cy is phenyl or a heteroaryl selected from the group consisting of furyl (furanyl), thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, isoxazolyl, oxazolyl, oxadiazolyl, isothiazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, indolyl, isoindolyl, quinolinyl and isoquinolinyl.
  • Cy is phenyl or a 5- or 6-membered heteroaryl, preferably selected from the group consisting of pyrazolyl, isothiazolyl, thiazolyl, pyridinyl, pyrimidinyl, pyrazinyl and thiadiazolyl.
  • Cy is phenyl or pyridinyl.
  • Cyis phenyl In some particularly preferred embodiments, Cyis phenyl.
  • Cy is pyridinyl
  • Cy is phenyl or pyridinyl
  • n is 1 or 2
  • R 3 is fluorine
  • n is 0 and Cy is a 5- or 6-membered heteroaryl, preferably selected from the group consisting of isothiazolyl, thiazolyl, pyridinyl, pyrimidinyl, pyrazinyl and thiadiazolyl.
  • the compound of formula (I) is a compound of the formula (la), (lb), (Ic), (Id), (le), (If), (Ig), (Ih), (Ii), (Ij) or (Ik): wherein
  • R 1 , R 2 , R 3 , R 4 and R 5 are as defined above for the compound of formula (I), and R 6 , R 7 and R 8 , if present, are each independently hydrogen or fluorine.
  • the compound of formula (I) is a compound of the formula (la), (lb), (Id), (le) or (li).
  • R 1 and R 2 with one or more preferred features of X, Cy, R 3 , R 4 , R 5 and n;
  • R 3 with one or more preferred features of X, Cy, R 1 , R 2 , R 4 , R 5 and n;
  • R 4 with one or more preferred features of X, Cy, R 1 , R 2 , R 3 , R 5 and n;
  • R 5 with one or more preferred features of X, Cy, R 1 , R 2 , R 3 , R 4 and n;
  • n with one or more preferred features of X, Cy, R 1 , R 2 , R 3 , R 4 and R 5 ;
  • the said preferred features can also be selected among the more preferred features of each of X, Cy, R 1 , R 2 , R 3 , R 4 , R 5 , n and the more preferred structure of the compound of the formula (I) according to formula (la), (lb), (Id), (le) or (li), so as to form more preferred subclasses of compounds according to the invention.
  • the compounds used according to the present invention are compounds of the formula (I) or salts, N-oxides or solvates thereof, wherein X is fluorine or chlorine;
  • R 1 and R 2 are each independently selected from the group consisting of hydrogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkyl substituted with Ci-C4-alkoxy, Ci-C4-alkyl substituted with Ci-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, Cs-Cg-cycloalkyl and phenyl, wherein said phenyl may be substituted with one to three substituents selected from halogen, Ci-C4-alkyl, hydroxy and C
  • R 1 and R 2 may form, together with the carbon atom to which they are linked, a Cs-Cg-cycloalkyl or oxetanyl ring, wherein the G-Cg-cycloalkyl or oxetanyl ring may be substituted with one to three substituents selected from the group consisting of halogen, hydroxy, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylcarbonyloxy and C1-C4- haloalkylcarbonyloxy; each R 3 , if present, is independently selected from the group consisting of halogen, nitro, cyano, Ci-
  • C4-alkyl Cs-Cg-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and C1-C4- alkoxy carbonyl;
  • R 4 is selected from the group consisting of hydrogen, hydroxy, Ci-Cg-alkyl, Ci-Cg- alkylcarbonyl, Ci-Cg-haloalkylcarbonyl, Ci-Cg-alkoxy and Ci-Cg-haloalkoxy;
  • R 5 is hydrogen or fluorine
  • Cy is phenyl or a heteroaryl selected from the group consisting of furyl (furanyl), thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, isoxazolyl, oxazolyl, oxadiazolyl, isothiazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, indolyl, isoindolyl, quinolinyl and isoquinolinyl, and n is 0, 1 or 2.
  • the compounds used according to the present invention are compounds of the formula (I) or salts, N-oxides or solvates thereof, wherein
  • X is fluorine
  • R 1 is selected from the group consisting of hydrogen, cyano, methyl, ethyl, iso-propyl, n-propyl, n- butyl, iso-butyl, tert-butyl, hydroxymethyl, trifluoromethyl, difluoromethyl, ethenyl, ethynyl, phenyl, cyclopentyl, cyclobutyl and cyclopropyl, wherein the phenyl may be substituted with one or two halogen atoms, and
  • R 2 is selected from the group consisting of hydrogen, methyl, ethyl, trifluoromethyl and difluoromethyl, or
  • R 1 and R 2 may form, together with the carbon atom to which they are linked, a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or oxetanyl ring, wherein said ring is unsubstituted or substituted with one to three substituents selected from the group consisting of fluorine, hydroxy, methyl, ethyl, trifluoromethyl, methoxy and acetyloxy; each R 3 , if present, is independently selected from the group consisting of fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, iso-propyl, n-propyl, n-butyl, iso-butyl, tert-butyl, cyclopropyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, methoxycarbonyl, eth
  • R 4 is hydrogen
  • R 5 is hydrogen or fluorine
  • Cy is phenyl or a 5- or 6-membered heteroaryl selected from the group consisting of pyrazolyl, isothiazolyl, thiazolyl, pyridinyl, pyrimidinyl, pyrazinyl and thiadiazolyl, and n is 0, 1 or 2.
  • the compounds used according to the present invention are compounds of the formula (I) or salts, N-oxides or solvates thereof, wherein
  • X is fluorine
  • R 1 is selected from the group consisting of hydrogen, cyano, methyl, ethyl, iso-propyl, n-propyl, n- butyl, iso-butyl, tert-butyl, hydroxymethyl, trifluoromethyl, difluoromethyl, ethenyl, ethynyl, phenyl, cyclopentyl, cyclobutyl and cyclopropyl, wherein the phenyl may be substituted with one or two substituents selected from fluorine and chlorine, and
  • R 2 is hydrogen, or
  • R 1 and R 2 form, together with the carbon atom to which they are linked, a cyclopropyl, cyclobutyl or oxetanyl ring; each R 3 , if present, is independently selected from the group consisting of fluorine, chlorine, bromine, methyl and methoxy;
  • R 4 is hydrogen
  • R 5 is hydrogen or fluorine
  • Cy is phenyl or pyridinyl; preferably phenyl or 2-pyridinyl, and n is 0, 1 or 2.
  • the compound of formula (I) is a compound of formula (la), (lb), (Id), (le) or (li).
  • Cy is phenyl or pyridinyl, n is 1 or 2, and at least one substituent R 3 is fluorine (the second substituent, if present, is as defined in the respective embodiment (I*), (I**) or (I***)).
  • Cy is phenyl or pyridinyl, n is 1 or 2, and R 3 is fluorine.
  • Cy is pyridinyl.
  • n is 0 and Cy is a 5- or 6- membered heteroaryl selected from the group consisting of isothiazolyl, thiazolyl, pyridinyl, pyrimidinyl, pyrazinyl and thiadiazolyl.
  • m is 1.
  • At least one of A 1 , A 2 and A 3 is CF or CH.
  • the compounds used according to the present invention are compounds of the formula (la) or salts, N-oxides or solvates thereof: wherein X, Cy, n, R 1 , R 2 , R 3 , R 4 and R 5 are as defined for the compound of formula (I), and R 6 , R 7 and R 8 are independently selected from hydrogen and fluorine.
  • the compounds used according to the present invention are compounds of the formula (lb) or salts, N-oxides or solvates thereof: wherein X, Cy, n, R 1 , R 2 , R 3 , R 4 and R 5 are as defined for the compound of formula (I), and R 6 and R 7 are independently selected from hydrogen and fluorine.
  • the compounds used according to the present invention are compounds of the formula (Ic) or salts, N-oxides or solvates thereof: wherein X, Cy, n, R 1 , R 2 , R 3 , R 4 and R 5 are as defined for the compound of formula (I), and R 6 and R 8 are independently selected from hydrogen and fluorine.
  • the compounds used according to the present invention are compounds of the formula (Id) or salts, N-oxides or solvates thereof: wherein X, Cy, n, R 1 , R 2 , R 3 , R 4 and R 5 are as defined for the compound of formula (I), and R 6 is selected from hydrogen and fluorine.
  • the compounds used according to the present invention are compounds of the formula (le) or salts, N-oxides or solvates thereof: wherein X, Cy, n, R 1 , R 2 , R 3 , R 4 and R 5 are as defined for the compound of formula (I), and R 7 is selected from hydrogen and fluorine.
  • the compounds used according to the present invention are compounds of the formula (If) or salts, N-oxides or solvates thereof: wherein X, Cy, n, R 1 , R 2 , R 3 , R 4 and R 5 are as defined for the compound of formula (I), and R 8 is selected from hydrogen and fluorine.
  • the compounds used according to the present invention are compounds of the formula (Ig) or salts, N-oxides or solvates thereof: wherein X, Cy, n, R 1 , R 2 , R 3 , R 4 and R 5 are as defined for the compound of formula (I).
  • the compounds used according to the present invention are compounds of the formula (Ih) or salts, N-oxides or solvates thereof: wherein X, Cy, , R 1 , R 2 , R 3 , R 4 and R 5 are as defined for the compound of formula (I), and R 7 and R 8 are independently selected from hydrogen and fluorine.
  • the compounds used according to the present invention are compounds of the formula (li) or salts, N-oxides or solvates thereof: wherein X, Cy, n, R 1 , R 2 , R 3 and R 4 are as defined for the compound of formula (I), and R 7 is selected from hydrogen and fluorine.
  • the compounds used according to the present invention are compounds of the formula (Ij) or salts, N-oxides or solvates thereof: wherein X, Cy, n, R 1 , R 2 , R 3 and R 4 are as defined for the compound of formula (I), and R 8 is selected from hydrogen and fluorine.
  • the compounds used according to the present invention are compounds of the formula (Ik) or salts, N-oxides or solvates thereof: wherein X, Cy, n, R 1 , R 2 , R 3 and R 4 are as defined for the compound of formula (I).
  • embodiments in accordance with embodiment (la), (lb), (Ic), (Id), (le), (If), (Ig), (Ih), (li), (Ij) or (Ik) (referred herein as embodiments (la*), (lb*), (Ic*), (Id*), (le*), (If*), (Ig*), (Ih*), (li*), (Ij*) and (Ik*)),
  • X is fluorine or chlorine
  • R 1 and R 2 are each independently selected from the group consisting of hydrogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkyl substituted with Ci-C4-alkoxy, Ci-C4-alkyl substituted with Ci-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, Cs-Cg-cycloalkyl and phenyl, wherein said phenyl may be substituted with one to three substituents selected from halogen, Ci-C4-alkyl, hydroxy and Ci-Cx-alkoxy. or
  • R 1 and R 2 may form, together with the carbon atom to which they are linked, a Cs-Cg-cycloalkyl or oxetanyl ring, wherein the G-Cg-cycloalkyl or oxetanyl ring may be substituted with one to three substituents selected from the group consisting of halogen, hydroxy, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylcarbonyloxy and C1-C4- haloalkylcarbonyloxy; each R 3 , if present, is independently selected from the group consisting of halogen, nitro, cyano, Ci-
  • C4-alkyl Cs-Cg-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and C1-C4- alkoxy carbonyl;
  • R 4 is selected from the group consisting of hydrogen, hydroxy, Ci-Cg-alkyl, Ci-Cg- alkylcarbonyl, Ci-Cg-haloalkylcarbonyl, Ci-Cg-alkoxy and Ci-Cg-haloalkoxy;
  • R 5 is hydrogen or fluorine
  • Cy is phenyl or a heteroaryl selected from the group consisting of furyl (furanyl), thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, isoxazolyl, oxazolyl, oxadiazolyl, isothiazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, indolyl, isoindolyl, quinolinyl and isoquinolinyl, and n is 0, 1 or 2.
  • embodiments in accordance with embodiment (la), (lb), (Ic), (Id), (le), (If), (Ig), (Ih), (li), (Ij) or (Ik) (referred herein as embodiments (la**), (lb**), (Ic**), (Id**), (le**), (If**), (Ig**), (Ih**), (li**), (Ij**) and (Ik**)),
  • X is fluorine
  • R 1 is selected from the group consisting of hydrogen, cyano, methyl, ethyl, iso-propyl, n-propyl, n- butyl, iso-butyl, tert-butyl, hydroxymethyl, trifluoromethyl, difluoromethyl, ethenyl, ethynyl, phenyl, cyclopentyl, cyclobutyl and cyclopropyl, wherein the phenyl may be substituted with one or two halogen atoms, and
  • R 2 is selected from the group consisting of hydrogen, methyl, ethyl, trifluoromethyl and difluoromethyl, or R 1 and R 2 may form, together with the carbon atom to which they are linked, a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or oxetanyl ring, wherein said ring is unsubstituted or substituted with one to three substituents selected from the group consisting of fluorine, hydroxy, methyl, ethyl, trifluoromethyl, methoxy and acetyloxy; each R 3 , if present, is independently selected from the group consisting of fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, iso-propyl, n-propyl, n-butyl, iso-butyl, tert-butyl, cyclopropyl, trifluoromethyl, difluoromethyl
  • R 4 is hydrogen
  • R 5 is hydrogen or fluorine
  • Cy is phenyl or a 5- or 6-membered heteroaryl selected from the group consisting of pyrazolyl, isothiazolyl, thiazolyl, pyridinyl, pyrimidinyl, pyrazinyl and thiadiazolyl, and n is 0, 1 or 2.
  • embodiments in accordance with embodiment (la), (lb), (Ic), (Id), (le), (If), (Ig), (Ih), (li), (Ij) or (Ik) (referred herein as embodiments (la***), (lb***), (Ic***), (Id***), (le***), (If***), (Ig***), (Ih***), (li***), (Ij***) and (Ik***)),
  • X is fluorine
  • R 1 is selected from the group consisting of hydrogen, cyano, methyl, ethyl, iso-propyl, n-propyl, n- butyl, iso-butyl, tert-butyl, hydroxymethyl, trifluoromethyl, difluoromethyl, ethenyl, ethynyl, phenyl, cyclopentyl, cyclobutyl and cyclopropyl, wherein the phenyl may be substituted with one or two substituents selected from fluorine and chlorine, and
  • R 2 is hydrogen, or
  • R 1 and R 2 form, together with the carbon atom to which they are linked, a cyclopropyl, cyclobutyl or oxetanyl ring; each R 3 , if present, is independently selected from the group consisting of fluorine, chlorine, bromine, methyl and methoxy;
  • R 4 is hydrogen
  • R 5 is hydrogen or fluorine
  • Cy is phenyl or pyridinyl; preferably phenyl or 2-pyridinyl, and n is 0, 1 or 2.
  • Cy is phenyl or pyridinyl, n is 1 or 2, and at least one substituent R 3 is fluorine (the second R 3 substituent, if present, is selected from the group consisting of fluorine, chlorine, bromine, methyl and methoxy).
  • R 3 is fluorine.
  • Cy is pyridinyl.
  • n is 0 and Cy is a 5- or 6-membered heteroaryl selected from the group consisting of isothiazolyl, thiazolyl, pyridinyl, pyrimidinyl, pyrazinyl and thiadiazolyl.
  • At least one of R 5 , R 6 and R 7 is fluorine.
  • the present invention also relates to a compound of formula (I)
  • X, A 1 , A 2 , A 3 , m, n, Cy, R 1 , R 2 , R 3 , R 4 and R 5 are as defined for the use of the compound of formula (I), and wherein compounds are excluded in which X is fluorine, A 1 is N, A 2 and A 3 are CH, m is 1, R 5 is hydrogen or chlorine, Cy is phenyl or a 5- or 6-membered heteroaryl, and R 1 , R 2 and R 4 are independently hydrogen or C1-C3 -alkyl; and provided that the compound of formula (I) is none of the following compounds:
  • Compound (a) is disclosed as a process intermediate in WO 2017/222951. The remaining excluded compounds are disclosed in WO 2013/080120 in connection with HDAC4 inhibitors for treating human diseases.
  • compounds are excluded in which X is fluorine, m is 1, A 1 , A 2 and A 3 are independently N or CH, wherein not more than two of A 1 , A 2 and A 3 are N, R 5 is hydrogen and R 1 , R 2 and R 4 are independently hydrogen or Ci-C -alkyl. and the compound of formula (I) is not compound (a).
  • compounds are excluded in which X is fluorine, m is 1, A 1 , A 2 and A 3 are independently N or CH, wherein not more than two of A 1 , A 2 and A 3 are N, R 5 is hydrogen and R 1 , R 2 and R 4 are independently hydrogen or C1-C3 -alkyl, and the compound of formula (la), (lb), (Ic), (Id), (le), (If), (Ig), (Ih), (li), (Ij) or (Ik) is not compound (a).
  • the compound of formula (I) is a compound of formula (lb), or a salt, N-oxide or solvate thereof wherein
  • X is fluorine or chlorine
  • R 1 and R 2 are each independently selected from the group consisting of hydrogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkyl substituted with Ci-C4-alkoxy, Ci-C4-alkyl substituted with Ci-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, Cs-Cg-cycloalkyl and phenyl, wherein said phenyl may be substituted with one to three substituents selected from halogen, Ci-C4-alkyl, hydroxy and Ci-Cx-alkoxy. or
  • R 1 and R 2 may form, together with the carbon atom to which they are linked, a Cs-Cg-cycloalkyl or oxetanyl ring, wherein the G-Cg-cycloalkyl or oxetanyl ring may be substituted with one to three substituents selected from the group consisting of halogen, hydroxy, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylcarbonyloxy and C1-C4- haloalkylcarbonyloxy; each R 3 , if present, is independently selected from the group consisting of halogen, nitro, cyano, Ci-
  • C4-alkyl Cs-Cg-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and C1-C4- alkoxy carbonyl;
  • R 4 is selected from the group consisting of hydrogen, hydroxy, Ci-Cg-alkyl, Ci-Cg- alkylcarbonyl, Ci-Cg-haloalkylcarbonyl, Ci-Cg-alkoxy and Ci-Cg-haloalkoxy;
  • R 5 , R 6 and R 7 are independently hydrogen or fluorine, wherein at least one of R 5 , R 6 and R 7 is fluorine;
  • Cy is phenyl or a heteroaryl selected from the group consisting of furyl (furanyl), thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, isoxazolyl, oxazolyl, oxadiazolyl, isothiazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, indolyl, isoindolyl, quinolinyl and isoquinolinyl, and n is 0, 1 or 2.
  • the compound of formula (I) is a compound of formula (lb), or a salt, N-oxide or solvate thereof, wherein
  • X is fluorine
  • R 1 is selected from the group consisting of hydrogen, cyano, methyl, ethyl, iso-propyl, n-propyl, n- butyl, iso-butyl, tert-butyl, hydroxymethyl, trifluoromethyl, difluoromethyl, ethenyl, ethynyl, phenyl, cyclopentyl, cyclobutyl and cyclopropyl, wherein the phenyl may be substituted with one or two halogen atoms, and
  • R 2 is selected from the group consisting of hydrogen, methyl, ethyl, trifluoromethyl and difluoromethyl, or
  • R 1 and R 2 may form, together with the carbon atom to which they are linked, a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or oxetanyl ring, wherein said ring is unsubstituted or substituted with one to three substituents selected from the group consisting of fluorine, hydroxy, methyl, ethyl, trifluoromethyl, methoxy and acetyloxy; each R 3 , if present, is independently selected from the group consisting of fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, iso-propyl, n-propyl, n-butyl, iso-butyl, tert-butyl, cyclopropyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, methoxycarbonyl, eth
  • R 4 is hydrogen
  • R 5 , R 6 and R 7 are independently hydrogen or fluorine, wherein at least one of R 5 , R 6 and R 7 is fluorine;
  • Cy is phenyl or a 5- or 6-membered heteroaryl selected from the group consisting of pyrazolyl, isothiazolyl, thiazolyl, pyridinyl, pyrimidinyl, pyrazinyl and thiadiazolyl, and n is 0, 1 or 2.
  • R 1 is selected from the group consisting of hydrogen, cyano, methyl, ethyl, iso-propyl, n-propyl, n- butyl, iso-butyl, tert-butyl, hydroxymethyl, trifluoromethyl, difluoromethyl, ethenyl, ethynyl, phenyl, cyclopentyl, cyclobutyl and cyclopropyl, wherein the phenyl may be substituted with one or two substituents selected from fluorine and chlorine, and
  • R 2 is hydrogen, or
  • R 1 and R 2 form, together with the carbon atom to which they are linked, a cyclopropyl, cyclobutyl or oxetanyl ring; each R 3 , if present, is independently selected from the group consisting of fluorine, chlorine, bromine, methyl and methoxy;
  • Cy is phenyl or pyridinyl; preferably phenyl or 2-pyridinyl, and n is 0, 1 or 2.
  • compounds of formula (I) selected from the group consisting of N-[l-pyridin-2-ylethyl]-5-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]pyridin-2-amine, 3-fluoro-N-[l-pyridin-2-ylethyl]-5-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]pyridin-2-amine, N-[l-(2-fluorophenyl)cyclopropyl]-5-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]pyridin-2-amine, N-[l-pyridin-2-ylethyl]-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]aniline, N-[l-(4-fluorophenyl)ethyl]-5-[5-(trifluoromethyl)-l,2,
  • the present invention also relates to the use of any compounds of formula (I) disclosed in Table 1.
  • the present invention also relates to intermediates for the preparation of compounds of formula (I).
  • the present invention relates to compounds of formula (II) as well as their acceptable salts, N- oxides or solvates:
  • the present invention also relates to processes for the preparation of compounds of formula (I).
  • the radicals Cy, X, A 1 , A 2 , A 3 , R 1 , R 2 , R 3 , R 4 , R 5 , n and m have the meanings given above for the compounds of formula (I). These definitions apply not only to the end products of the formula (I) but likewise to all intermediates.
  • Compounds of formula (I) can be prepared, according to process Pl, by reacting amidoximes of formula (II) with haloalkylacetic anhydride or haloalkylacetyl chloride in a suitable solvent such as tetrahydrofurane or dichloromethane optionally in presence of a base such as triethylamine or pyridine, preferably at room temperature, as previously described in W02013080120.
  • a suitable solvent such as tetrahydrofurane or dichloromethane
  • a base such as triethylamine or pyridine
  • Amidoximes of formula (II) can be prepared according to known procedures (see for examples W02013080120), as shown in process P2 by treating nitriles of formula (III) with hydroxylamine (or its hydrochloride salt) in the presence of a base such as triethylamine in a solvent such as ethanol.
  • compounds of formula (I) can be prepared, according to process P4, from a compound of formula (V), wherein LG2 is a leaving group by nucleophilic substitution with a compound of formula (VI) (as described for example in European Journal of Medicinal Chemistry, 135, 531-543; 2017 or Bioorganic & Medicinal Chemistry, 25(17), 4553-4559; 2017) optionally in presence of a base (like for example triethylamine) or an acid (like for example p-toluenesulfonic acid or (lS)-(+)-10- camphorsulfonic acid) in a solvent such as for example dichloromethane or dioxane.
  • a base like for example triethylamine
  • an acid like for example p-toluenesulfonic acid or (lS)-(+)-10- camphorsulfonic acid
  • solvent such as for example dichloromethane or dioxane.
  • transition metal catalyst such as tris(dibenzylideneacetoneetone)dipalladium (as described for example in WO2012/143415 or WO2019/063748) or copper(I) iodide (as described for example in W02000/068198).
  • compounds of formulae (I) can be prepared, according to process P5, from a compound of formula (VII) with a compound of formula (VIII) wherein LG3 is a leaving group such as chlorine by nucleophilic substitution (as described for example in European Journal of Medicinal Chemistry, 135, 531-543; 2017 or Bioorganic & Medicinal Chemistry, 25(17), 4553-4559; 2017) optionally in presence of a base (like for example triethylamine) or an acid (like for example p-toluenesulfonic acid or ( 1 S)- (+)-10-Camphorsulfonic acid) in a solvent such as for example dichloromethane or dioxane.
  • a base like for example triethylamine
  • an acid like for example p-toluenesulfonic acid or ( 1 S)- (+)-10-Camphorsulfonic acid
  • solvent such as for example dichloromethane or dioxane.
  • compounds of formula (I) can be prepared, according to process P6, from a compound of formula (IX) with a compound of formula (X), wherein LG4 is a leaving group, by nucleophilic substitution (as described for example in Medicinal Chemistry Research, 22(11), 5267-5273; 2013 or W02013080120) optionally in presence of a base (like for example triethylamine), optionally in presence of a solvent such as for example dichloromethane.
  • a base like for example triethylamine
  • a solvent such as for example dichloromethane.
  • compounds of formula (III) can be prepared, according to process P7, from a compound of formula (XI), wherein LG5 is a leaving group as for example chlorine by nucleophilic substitution with a compound of formula (VI) (as described for example in European Journal of Medicinal Chemistry, 135, 531-543; 2017 or Bioorganic & Medicinal Chemistry, 25(17), 4553-4559; 2017) optionally in presence of a base (like for example triethylamine) or an acid (like for example p-toluenesulfonic acid or (lS)-(+)-10-camphorsulfonic acid) in a solvent such as for example dichloromethane or dioxane.
  • a base like for example triethylamine
  • an acid like for example p-toluenesulfonic acid or (lS)-(+)-10-camphorsulfonic acid
  • solvent such as for example dichloromethane or dioxane.
  • transition metal catalyst such as tris(dibenzylideneacetoneetone)dipalladium (as described for example in WO2012143415 or WO2019063748) or copper(I) iodide (as described for example in W02000068198).
  • processes Pl to P7 can be performed if appropriate in the presence of a solvent and if appropriate in the presence of a base.
  • Suitable solvents for carrying out processes Pl to P7 according to the invention are customary inert organic solvents. Preference is given to using optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichlorethane or trichlorethane; ethers, such as diethyl ether, diisopropyl ether, methyl tertbutyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles, such as acetonitrile, propionit
  • A'A'-dimcthylacctamidc A-methylformanilide, A-methylpyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate, sulfoxides, such as dimethyl sulfoxide or sulfones, such as sulfolane.
  • Suitable bases for carrying out processes Pl to P7 according to the invention are inorganic and organic bases which are customary for such reactions.
  • pyridine A-methylpiperidine, A'A'-dimcthylaminopyridinc.
  • DABCO diazabicyclo[2.2.2]octane
  • DBN l,5-diazabicyclo[4.3.0]non-5-ene
  • DBU l,8-diazabicyclo[5.4.0]undec-7-ene
  • reaction temperature can independently be varied within a relatively wide range.
  • processes according to the invention are carried out at temperatures between -20°C and 160°C.
  • Processes Pl to P7 according to the invention are generally independently carried out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure.
  • reaction mixture is treated with water and the organic phase is separated off and, after drying, concentrated under reduced pressure. If appropriate, the remaining residue can be freed by customary methods, such as chromatography or recrystallization, from any impurities that can still be present.
  • compositions and formulations are provided.
  • the present invention further relates to a composition for controlling unwanted microorganisms, in particular phytopathogenic fungi, comprising one or more compounds of formula (I) in a fimgicidally effective amount.
  • composition comprises at least one compound of the invention and at least one agriculturally suitable auxiliary, e.g. carrier(s) and/or surfactant(s).
  • agriculturally suitable auxiliary e.g. carrier(s) and/or surfactant(s).
  • a carrier is a solid or liquid, natural or synthetic, organic or inorganic substance that is generally inert.
  • the carrier generally improves the application of the compounds, for instance, to plants, plants parts or seeds.
  • suitable solid carriers include, but are not limited to, ammonium salts, in particular ammonium sulfates, ammonium phosphates and ammonium nitrates, natural rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, silica gel and synthetic rock flours, such as finely divided silica, alumina and silicates.
  • typically useful solid carriers for preparing granules include, but are not limited to crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, synthetic granules of inorganic and organic flours and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks.
  • suitable liquid carriers include, but are not limited to, water, organic solvents and combinations thereof.
  • suitable solvents include polar and nonpolar organic chemical liquids, for example from the classes of aromatic and nonaromatic hydrocarbons (such as cyclohexane, paraffins, alkylbenzenes, xylene, toluene, tetrahydronaphthalene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride), alcohols and polyols (which may optionally also be substituted, etherified and/or esterified, such as ethanol, propanol, butanol, benzylalcohol, cyclohexanol or glycol), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amide
  • the carrier may also be a liquefied gaseous extender, i.e. liquid which is gaseous at standard temperature and under standard pressure, for example aerosol propellants such as halohydrocarbons, butane, propane, nitrogen and carbon dioxide.
  • a liquefied gaseous extender i.e. liquid which is gaseous at standard temperature and under standard pressure
  • aerosol propellants such as halohydrocarbons, butane, propane, nitrogen and carbon dioxide.
  • Preferred solid carriers are selected from clays, talc and silica.
  • Preferred liquid carriers are selected from water, fatty acid amides and esters thereof, aromatic and nonaromatic hydrocarbons, lactams and carbonic acid esters.
  • the amount of carrier typically ranges from 1 to 99.99%, preferably from 5 to 99.9%, more preferably from 10 to 99.5%, and most preferably from 20 to 99% by weight of the composition.
  • Liquid carriers are typically present in a range of from 20 to 90%, for example 30 to 80% by weight of the composition.
  • Solid carriers are typically present in a range of from 0 to 50%, preferably 5 to 45%, for example 10 to 30% by weight of the composition.
  • composition comprises two or more carriers, the outlined ranges refer to the total amount of carriers.
  • the surfactant can be an ionic (cationic or anionic), amphoteric or non-ionic surfactant, such as ionic or non-ionic emulsifier(s), foam former(s), dispersant(s), wetting agent(s), penetration enhancer(s) and any mixtures thereof.
  • surfactants include, but are not limited to, salts of polyacrylic acid, salts of lignosulfonic acid (such as sodium lignosulfonate), salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide and/or propylene oxide with fatty alcohols, fatty acids or fatty amines (for example, polyoxyethylene fatty acid esters such as castor oil ethoxylate, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols) and ethoxylates thereof (such as tristyrylphenol ethoxylate), salts of sulfosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyols (such a fatty acid esters of g,
  • Preferred surfactants are selected from polyoxyethylene fatty alcohol ethers, polyoxyethylene fatty acid esters, alkylbenzene sulfonates, such as calcium dodecylbenzenesulfonate, castor oil ethoxylate, sodium lignosulfonate and arylphenol ethoxylates, such as tristyrylphenol ethoxylate.
  • the amount of surfactants typically ranges from 5 to 40%, for example 10 to 20%, by weight of the composition.
  • auxiliaries include water repellents, siccatives, binders (adhesive, tackifier, fixing agent, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids such as cephalins and lecithins and synthetic phospholipids, polyvinylpyrrolidone and tylose), thickeners and secondary thickeners (such as cellulose ethers, acrylic acid derivatives, xanthan gum, modified clays, e.g. the products available under the name Bentone, and finely divided silica), stabilizers (e.g.
  • cold stabilizers preservatives (e.g. dichlorophene and benzyl alcohol hemiformal), antioxidants, light stabilizers, in particular UV stabilizers, or other agents which improve chemical and/or physical stability), dyes or pigments (such as inorganic pigments, e.g. iron oxide, titanium oxide and Prussian Blue; organic dyes, e.g. alizarin, azo and metal phthalocyanine dyes), antifoams (e.g.
  • silicone antifoams and magnesium stearate silicone antifoams and magnesium stearate
  • antifreezes stickers, gibberellins and processing auxiliaries, mineral and vegetable oils, perfumes, waxes, nutrients (including trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc), protective colloids, thixotropic substances, penetrants, sequestering agents and complex formers.
  • auxiliaries depends on the intended mode of application of the compound of the invention and/or on the physical properties of the compound(s). Furthermore, the auxiliaries may be chosen to impart particular properties (technical, physical and/or biological properties) to the compositions or use forms prepared therefrom. The choice of auxiliaries may allow customizing the compositions to specific needs.
  • composition of the invention may be provided to the end user as ready-for-use formulation, i.e. the compositions may be directly applied to the plants or seeds by a suitable device, such as a spraying or dusting device.
  • a suitable device such as a spraying or dusting device.
  • the compositions may be provided to the end user in the form of concentrates which have to be diluted, preferably with water, prior to use.
  • composition of the invention can be prepared in conventional manners, for example by mixing the compound of the invention with one or more suitable auxiliaries, such as disclosed herein above.
  • the composition comprises a fungicidally effective amount of the compound(s) of the invention.
  • effective amount denotes an amount, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound of the invention used.
  • the composition according to the invention contains from 0.01 to 99% by weight, preferably from 0.05 to 98% by weight, more preferred from 0.1 to 95% by weight, even more preferably from 0.5 to 90% by weight, most preferably from 1 to 80% by weight of the compound of the invention. It is possible that a composition comprises two or more compounds of the invention. In such case the outlined ranges refer to the total amount of compounds of the present invention.
  • composition of the invention may be in any customary composition type, such as solutions (e.g aqueous solutions), emulsions, water- and oil-based suspensions, powders (e.g. wettable powders, soluble powders), dusts, pastes, granules (e.g. soluble granules, granules for broadcasting), suspoemulsion concentrates, natural or synthetic products impregnated with the compound of the invention, fertilizers and also microencapsulations in polymeric substances.
  • the compound of the invention may be present in a suspended, emulsified or dissolved form. Examples of particular suitable composition types are solutions, watersoluble concentrates (e.g.
  • SL LS
  • dispersible concentrates DC
  • suspensions and suspension concentrates e.g. SC, OD, OF, FS
  • emulsifiable concentrates e.g. EC
  • emulsions e.g. EW, EO, ES, ME, SE
  • capsules e.g. CS, ZC
  • pastes pastilles
  • wettable powders or dusts e.g. WP, SP, WS, DP, DS
  • pressings e.g. BR, TB, DT
  • granules e.g. WG, SG, GR, FG, GG, MG
  • insecticidal articles e.g.
  • compositions types are defined by the Food and Agriculture Organization of the United Nations (FAO). An overview is given in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed. May 2008, Croplife International.
  • the composition of the invention is in form of one of the following types: EC, SC, FS, SE, OD and WG, more preferred EC, SC, OD and WG.
  • composition types and their preparation are given below. If two or more compounds of the invention are present, the outlined amount of compound of the invention refers to the total amount of compounds of the present invention. This applies mutatis mutandis for any further component of the composition, if two or more representatives of such component, e.g. wetting agent, binder, are present.
  • SL, LS Water-soluble concentrates
  • ком ⁇ онент e.g. a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • surfactant e.g. a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e.g. aromatic hydrocarbon
  • This mixture is added to such amount of water by means of an emulsifying machine to result in a total amount of 100 % by weight.
  • the resulting composition is a homogeneous emulsion. Before application the emulsion may be further diluted with water.
  • a suitable grinding equipment e.g. an agitated ball mill
  • 20-60 % by weight of at least one compound of the invention are comminuted with addition of 2-10 % by weight surfactant (e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1 -2 % by weight thickener (e.g. xanthan gum) and water to give a fine active substance suspension.
  • surfactant e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether
  • thickener e.g. xanthan gum
  • water e.g. xanthan gum
  • the water is added in such amount to result in a total amount of 100 % by weight. Dilution with water gives a stable suspension of the active substance.
  • binder e.g. polyvinylalcohol
  • a suitable grinding equipment e.g. an agitated ball mill
  • 20-60 % by weight of at least one compound of the invention are comminuted with addition of 2-10 % by weight surfactant (e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1-2 % by weight thickener (e.g. modified clay, in particular Bentone, or silica) and an organic carrier to give a fine active substance oil suspension.
  • the organic carrier is added in such amount to result in a total amount of 100 % by weight. Dilution with water gives a stable dispersion of the active substance.
  • 50-80 % by weight of at least one compound of the invention are ground finely with addition of surfactant (e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether) and converted to water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed).
  • surfactant e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether
  • the surfactant is used in such amount to result in a total amount of 100 % by weight. Dilution with water gives a stable dispersion or solution of the active substance.
  • WP, SP, WS Water-dispersible powders and water-soluble powders
  • % by weight of at least one compound of the invention are ground in a rotor-stator mill with addition of 1-8 % by weight surfactant (e.g. sodium lignosulfonate, polyoxyethylene fatty alcohol ether) and such amount of solid carrier, e.g. silica gel, to result in a total amount of 100 % by weight. Dilution with water gives a stable dispersion or solution of the active substance.
  • surfactant e.g. sodium lignosulfonate, polyoxyethylene fatty alcohol ether
  • solid carrier e.g. silica gel
  • agitated ball mill 5-25 % by weight of at least one compound of the invention are comminuted with addition of 3-10 % by weight surfactant (e.g. sodium lignosulfonate), 1-5 % by weight binder (e.g. carboxymethylcellulose) and such amount of water to result in a total amount of 100 % by weight.
  • surfactant e.g. sodium lignosulfonate
  • binder e.g. carboxymethylcellulose
  • 5-20 % by weight of at least one compound of the invention are added to 5-30 % by weight organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 % by weight surfactant blend (e.g. polyoxyethylene fatty alcohol ether and arylphenol ethoxylate), and such amount of water to result in a total amount of 100 % by weight.
  • organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
  • surfactant blend e.g. polyoxyethylene fatty alcohol ether and arylphenol ethoxylate
  • An oil phase comprising 5-50 % by weight of at least one compound of the invention, 0-40 % by weight water-insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 % by weight acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 % by weight of at least one compound of the invention, 0-40 % by weight water-insoluble organic solvent (e.g.
  • At least one compound of the invention are ground finely and associated with such amount of solid carrier (e.g. silicate) to result in a total amount of 100 % by weight.
  • Granulation is achieved by extrusion, spray-drying or the fluidized bed.
  • 1-50 % by weight of at least one compound of the invention are dissolved in such amount of organic solvent, e.g. aromatic hydrocarbon, to result in a total amount of 100 % by weight.
  • organic solvent e.g. aromatic hydrocarbon
  • compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 % by weight preservatives, 0.1-1 % by weight antifoams, 0.1-1 % by weight dyes and/or pigments, and 5-10% by weight antifreezes.
  • the compound used according to the invention and the composition of the invention can be mixed with other active ingredients like fungicides, bactericides, acaricides, nematicides, insecticides, biological control agents or herbicides. Mixtures with fertilizers, growth regulators, safeners, nitrification inhibitors, semiochemicals and/or other agriculturally beneficial agents are also possible. This may allow to broaden the activity spectrum or to prevent development of resistance. Examples of known fungicides, insecticides, acaricides, nematicides and bactericides are disclosed in the Pesticide Manual, 17th Edition.
  • fungicides which could be mixed with the compound used according to the invention and the composition of the invention are: 1) Inhibitors of the ergosterol biosynthesis, for example (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenbuconazole, (1.005) fenhexamid, (1.006) fenpropidin, (1.007) fenpropimorph, (1.008) fenpyrazamine, (1.009) fluquinconazole, (1.010) flutriafol, (1.011) hexaconazole, (1.012) imazalil, (1.013) imazalil sulfate, (1.014) ipconazole, (1.015) ipfentrifluconazole, (1.016) mefentrifluconazole, (1.017) metconazole, (1.018) myclobutanil, (1.019) paclobutrazol, (1.020) pencon
  • Inhibitors of the respiratory chain at complex I or II for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) cyclobutrifluram, (2.006) flubeneteram, (2.007) fluindapyr, (2.008) fluopyram, (2.009) flutolanil, (2.010) fluxapyroxad, (2.011) furametpyr, (2.012) inpyrfluxam, (2.013) Isofetamid, (2.014) isoflucypram, (2.015) isopyrazam, (2.016) penflufen, (2.017) penthiopyrad, (2.018) pydiflumetofen, (2.019) pyrapropoyne, (2.020) pyraziflumid, (2.021) sedaxane, (2.022) l,3-dimethyl-N-(l,l,3-trimethyl-2,3-dihydr
  • Inhibitors of the respiratory chain at complex III for example (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, (3.011) fenpicoxamid, (3.012) florylpicoxamid, (3.013) flufenoxystrobin, (3.014) fluoxastrobin, (3.015) kresoxim-methyl, (3.016) mandestrobin, (3.017) metominostrobin, (3.018) metyltetraprole, (3.019) orysastrobin, (3.020) picoxystrobin, (3.021) pyraclostrobin, (3.022) pyrametostrobin, (3.021)
  • Inhibitors of the mitosis and cell division for example (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) fluopimomide, (4.006) metrafenone, (4.007) pencycuron, (4.008) pyridachlometyl, (4.009) pyriofenone (chlazafenone), (4.010) thiabendazole, (4.011) thiophanate -methyl, (4.012) zoxamide, (4.013) 3-chloro-5-(4-chlorophenyl)-4-(2,6- difluorophenyl)-6-methylpyridazine, (4.014) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6- trifluorophenyl)pyridazine, (4.015) 4-(2-bromo-4-fluorophenyl)-
  • Compounds capable to induce a host defence for example (6.001) acibenzolar-S-methyl, (6.002) fosetyl-aluminium, (6.003) fosetyl-calcium, (6.004) fosetyl-sodium, (6.005) isotianil, (6.006) phosphorous acid and its salts, (6.007) probenazole, (6.008) tiadinil.
  • Inhibitors of the amino acid and/or protein biosynthesis for example (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil.
  • Inhibitors of the ATP production for example (8.001) silthiofam.
  • Inhibitors of the cell wall synthesis for example (9.001) benthiavalicarb, (9.002) dimethomorph,
  • Inhibitors of the lipid synthesis or transport, or membrane synthesis for example (10.001) fluoxapiprolin, (10.002) natamycin, (10.003) oxathiapiprolin, (10.004) propamocarb, (10.005) propamocarb hydrochloride, (10.006) propamocarb-fosetylate, (10.007) tolclofos-methyl, (10.008) l-(4- ⁇ 4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl ⁇ piperidin-l-yl)-2-[5- methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]ethanone, (10.009) l-(4- ⁇ 4-[(5S)-5-(2,6-difluorophenyl)- 4,5-dihydro-l,2-
  • Inhibitors of the melanin biosynthesis for example (11.001) tolprocarb, (11.002) tricyclazole.
  • Inhibitors of the nucleic acid synthesis for example (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).
  • Inhibitors of the signal transduction for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxyfen, (13.006) vinclozolin.
  • the compound used according to the invention and the composition of the invention may also be combined with one or more biological control agents.
  • biological control is defined as control of harmful organisms such as a phytopathogenic fungi and/or insects and/or acarids and/or nematodes by the use or employment of a biological control agent.
  • biological control agent is defined as an organism other than the harmful organisms and / or proteins or secondary metabolites produced by such an organism for the purpose of biological control. Mutants of the second organism shall be included within the definition of the biological control agent.
  • mutant refers to a variant of the parental strain as well as methods for obtaining a mutant or variant in which the pesticidal activity is greater than that expressed by the parental strain.
  • the ’’parent strain“ is defined herein as the original strain before mutagenesis.
  • the parental strain may be treated with a chemical such as N-methyl-N'-nitro-N- nitrosoguanidine, ethylmethanesulfone, or by irradiation using gamma, x-ray, or UV-irradiation, or by other means well known to those skilled in the art.
  • a chemical such as N-methyl-N'-nitro-N- nitrosoguanidine, ethylmethanesulfone, or by irradiation using gamma, x-ray, or UV-irradiation, or by other means well known to those skilled in the art.
  • Known mechanisms of biological control agents comprise enteric bacteria that control root rot by out-competing fungi for space on the surface of the root.
  • Bacterial toxins, such as antibiotics have been used to control pathogens.
  • the toxin can be isolated and applied directly to the plant or the bacterial species may be administered so it produces the toxin in situ.
  • a ’’variant is a strain having all the identifying characteristics of the NRRL or ATCC Accession Numbers as indicated in this text and can be identified as having a genome that hybridizes under conditions of high stringency to the genome of the NRRL or ATCC Accession Numbers.
  • Hybridization refers to a reaction in which one or more polynucleotides react to form a complex that is stabilized via hydrogen bonding between the bases of the nucleotide residues.
  • the hydrogen bonding may occur by Watson-Crick base pairing, Hoogstein binding, or in any other sequence-specific manner.
  • the complex may comprise two strands forming a duplex structure, three or more strands forming a multi-stranded complex, a single self-hybridizing strand, or any combination of these.
  • Hybridization reactions can be performed under conditions of different “stringency”. In general, a low stringency hybridization reaction is carried out at about 40 °C in 10 X SSC or a solution of equivalent ionic strength/temperature. A moderate stringency hybridization is typically performed at about 50 °C in 6 X SSC, and a high stringency hybridization reaction is generally performed at about 60 °C in 1 X SSC.
  • a variant of the indicated NRRL or ATCC Accession Number may also be defined as a strain having a genomic sequence that is greater than 85%, more preferably greater than 90% or more preferably greater than 95% sequence identity to the genome of the indicated NRRL or ATCC Accession Number.
  • a polynucleotide or polynucleotide region (or a polypeptide or polypeptide region) has a certain percentage (for example, 80%, 85%, 90%, or 95%) of “sequence identity” to another sequence means that, when aligned, that percentage of bases (or amino acids) are the same in comparing the two sequences. This alignment and the percent homology or sequence identity can be determined using software programs known in the art, for example, those described in Current Protocols in Molecular Biology (F. M. Ausubel et al., eds., 1987).
  • NRRL is the abbreviation for the Agricultural Research Service Culture Collection, an international depositary authority for the purposes of deposing microorganism strains under the Budapest treaty on the international recognition of the deposit of microorganisms for the purposes of patent procedure, having the address National Center for Agricultural Utilization Research, Agricultural Research service, U.S. Department of Agriculture, 1815 North university Street, Peroira, Illinois 61604 USA.
  • ATCC is the abbreviation for the American Type Culture Collection, an international depositary authority for the purposes of deposing microorganism strains under the Budapest treaty on the international recognition of the deposit of microorganisms for the purposes of patent procedure, having the address ATCC Patent Depository, 10801 University Boulevard., Manassas, VA 10110 USA.
  • biological control agents which may be combined with the compound used according to the invention and the composition of the invention are:
  • Antibacterial agents selected from the group of:
  • (Al) bacteria such as (Al.01) Bacillus subtilis, in particular strain QST713/AQ713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, having NRRL Accession No. B21661, U.S. Patent No. 6,060,051); (Al.02) Bacillus sp., in particular strain D747 (available as DOUBLE NICKEL® from Kumiai Chemical Industry Co., Ltd.), having Accession No. FERM BP- 8234, U.S. Patent No. 7,094,592; (Al.03) Bacillus pumilus, in particular strain BU F-33, having NRRL Accession No.
  • Bacillus subtilis strain BU1814 (available as VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA from BASF SE); (A 1.07) Bacillus mojavensis strain R3B (Accession No. NCAIM (P) B001389) (WO 2013/034938) from Certis USA LLC, a subsidiary of Mitsui & Co.; (Al.08) Bacillus subtilis CX-9060 from Certis USA LLC, a subsidiary of Mitsui & Co.; (A 1.09) Paenibacillus polymyxa, in particular strain AC-1 (e.g.
  • Pseudomonas proradix e.g. PRORADIX® from Sourcon Padena
  • Pantoea agglomerans in particular strain E325 (Accession No. NRRL B-21856) (available as BLOOMTIME BIOLOGICALTM FD BIOPESTICIDE from Northwest Agri Products); and
  • (A2) fungi such as (A2.01) Aureobasidium pullulans, in particular blastospores of strain DSM14940, blastospores of strain DSM 14941 ormixtures of blastospores of strains DSM14940 and DSM14941 (e.g., BOTECTOR® and BLOSSOM PROTECT®from bio-ferm, CH); (A2.02) Pseudozyma aphidis (as disclosed in WO2011/151819 by Yissum Research Development Company of the Hebrew University of Jerusalem); (A2.03) Saccharomyces cerevisiae, in particular strains CNCM No. 1-3936, CNCM No. I- 3937, CNCM No. 1-3938 or CNCM No. 1-3939 (WO 2010/086790) from Lesaffre et Compagnie, FR;
  • Aureobasidium pullulans in particular blastospores of strain DSM14940, blastospores of strain DSM 14941 ormixtures
  • (Bl) bacteria for example (Bl.01) Bacillus subtilis, in particular strain QST713/AQ713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, having NRRL Accession No. B21661 and described in U.S. Patent No. 6,060,051); (Bl.02) Bacillus pumilus, in particular strain QST2808 (available as SONATA® from Bayer CropScience LP, US, having Accession No. NRRL B- 30087 and described in U.S. Patent No.
  • Bacillus pumilus in particular strain GB34 (available as Yield Shield® from Bayer AG, DE);
  • Bacillus amyloliquefaciens in particular strain D747 (available as Double NickelTM from from Kumiai Chemical Industry Co., Ltd., having accession number FERM BP-8234, US Patent No.
  • Bacillus subtilis Y1336 (available as BIOBAC® WP from Bion-Tech, Taiwan, registered as a biological fungicide in Taiwan under Registration Nos. 4764, 5454, 5096 and 5277); (Bl.07) Bacillus subtilis strain MBI 600 (available as SUBTILEX from BASF SE), having Accession Number NRRL B-50595, U.S. Patent No. 5,061,495; (Bl.08) Bacillus subtilis strain GB03 (available as Kodiak® from Bayer AG, DE); (Bl.09) Bacillus subtilis var. amyloliquefaciens strain FZB24 having Accession No.
  • DSM 10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA Registration No. 70127-5)); (Bl.10) Bacillus mycoides, isolate J , having Accession No. B- 30890 (available as BMJ TGAI® or WG and LifeGardTM from Certis USA LLC, a subsidiary of Mitsui & Co.); (Bl.11) Bacillus licheniformis, in particular strain SB3086 , having Accession No. ATCC 55406, WO 2003/000051 (available as ECOGUARD® Biofungicide and GREEN RELEAFTM from Novozymes); (Bl.12) a Paenibacillus sp. strain having Accession No.
  • Bacillus amyloliquefaciens strain FZB42 Bacillus amyloliquefaciens strain FZB42, Accession No. DSM 23117 (available as RHIZOVITAL® from ABiTEP, DE);
  • Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (QUARTZO® (WG) and PRESENCE® (WP) from FMC Corporation);
  • Bacillus mojavensis strain R3B accesion No.
  • NCAIM (P) B001389) (WO 2013/034938) from Certis USA LLC, a subsidiary of Mitsui & Co.;
  • NRRL B-50897, WO 2017/019448 e.g., HOWLERTM and ZIO® from AgBiome Innovations, US
  • Pseudomonas chlororaphis in particular strain MA342 (e.g. CEDOMON®, CERALL®, and CEDRESS® by Bioagri and Koppert)
  • Streptomyces lydicus strain WYEC108 also known as Streptomyces lydicus strain WYCD108US
  • ACTINO-IRON® and ACTINO VATE® from Novozymes Bl.24
  • Agrobacterium radiobacter strain K84 e.g.
  • GALLTROL-A® from AgBioChem, CA); (Bl.25) Agrobacterium radiobacter strain K1026 (e.g. NOGALLTM from BASF SE); (Bl.26) Bacillus subtilis KTSB strain (FOLIACTIVE® from Donaghys); (Bl.27) Bacillus subtilis IAB/BS03 (AVIVTM from STK Bio-Ag Technologies); (Bl.28) Bacillus subtilis strain Y1336 (available as BIOBAC® WP from Bion- Tech, Taiwan, registered as a biological fungicide in Taiwan under Registration Nos. 4764, 5454, 5096 and 5277); (B1.29) Bacillus amyloliquefaciens isolate B246 (e.g.
  • (B2) fungi for example: (B2.01) Coniothyrium minitans, in particular strain CON/M/91-8 (Accession No. DSM-9660; e.g. Contans ® from Bayer CropScience Biologies GmbH); (B2.02) Metschnikowia fructicola, in particular strain NRRL Y-30752; (B2.03) Microsphaeropsis ochracea,' (B2.04) Trichoderma atroviride, in particular strain SCI (having Accession No. CBS 122089, WO 2009/116106 and U.S. Patent No. 8,431,120 (from Bi-PA)), strain 77B (T77 from Andermatt Biocontrol) or strain LU132 (e.g.
  • Trichoderma harzianum strain T- 22 e.g. Trianum-P from Andermatt Biocontrol or Koppert
  • strain Cepa Simb-T5 from Simbiose Agro
  • Gliocladium roseum also known as Clonostachys rosea f. rosea
  • strain 321U from Adjuvants Plus
  • strain ACM941 as disclosed in Xue (Efficacy of Clonostachys rosea strain ACM94 1 and fungicide seed treatments for controlling the root tot complex of field pea, Can Jour Plant Sci 83(3): 519-524), or strain IK726 (Jensen DF, et al.
  • Trichoderma atroviride Trichoderma atroviride, strain ATCC 20476 (IMI 206040); (B2.17) Trichoderma atroviride, strain Ti l (IMI352941/ CECT20498); (B2.18) Trichoderma harmatunv, (B2.19) Trichoderma harzianum,' (B2.20) Trichoderma harzianum rifai T39 (e.g. Trichodex® from Makhteshim, US); (B2.21) Trichoderma asperellum, in particular, strain kd (e.g. T-Gro from Andermatt Biocontrol); (B2.22) Trichoderma harzianum, strain ITEM 908 (e.g.
  • Trianum-P Trianum-P from Koppert
  • B2.23 Trichoderma harzianum, strain TH35 (e.g. Root-Pro by Mycontrol);
  • Trichoderma virens also known as Gliocladium virens), in particular strain GL-21 (e.g. SoilGard by Certis, US);
  • B2.25 Trichoderma viride, strain TVl(e.g. Trianum-P by Koppert);
  • Ampelomyces quisqualis in particular strain AQ 10 (e.g.
  • NM 99/06216 e.g., BOTRY-ZEN® by Botry-Zen Ltd, New Zealand and BOTRYSTOP® from BioWorks, Inc.
  • B2.43 Verticillium albo-atrum (formerly V. dahliae), strain WCS850 having Accession No. WCS850, deposited at the Central Bureau for Fungi Cultures (e.g., DUTCH TRIG® by Tree Care Innovations);
  • Verticillium chlamydosporiunr B2.45) mixtures of Trichoderma asperellum strain ICC 012 (also known as Trichoderma harzianum ICC012), having Accession No.
  • CABI CC IMI 392716 and Trichoderma gamsii (formerly T. viride) strain ICC 080 having Accession No. IMI 392151 (e.g., BIO-TAMTM from Isagro USA, Inc. and BIODERMA® by Agrobiosol de Mexico, S.A. de C.V.); (B2.46) Trichoderma asperelloides JM41R (Accession No. NRRL B-50759) (TRICHO PLUS® from BASF SE); (B2.47) Aspergillus flavus strain NRRL 21882 (products known as AFLA-GUARD® from Syngenta/ChemChina); (B2.48) Chaetomium cupreum (Accession No. CABI 353812) (e.g.
  • BIOKUPRUMTM by AgriLife B2.49 Saccharomyces cerevisiae, in particular strain LASO2 (from Agro-Levures et Derives), strain LAS 117 cell walls (CEREVISANE® from Lesaffre; ROMEO® from BASF SE), strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. I- 3938, CNCM No. 1-3939 (WO 2010/086790) from Lesaffre et Compagnie, FR; (B2.50) Trichoderma virens strain G-41, formerly known as Gliocladium virens (Accession No.
  • ATCC 20906 (e.g., ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP from BioWorks, US); (B2.51) Trichoderma hamatum, having Accession No. ATCC 28012; (B2.52) Ampelomyces quisqualis strain AQ10, having Accession No.
  • CNCM 1-807 e.g., AQ 10® by IntrachemBio Italia
  • Penicillium steckii DM 27859; WO 2015/067800) from BASF SE;
  • B2.55 Chaetomium glohosum available as RIVADIOM® by Rivale
  • B2.56 Cryptococcus flavescens strain 3C (NRRL Y-50378);
  • B2.57 Dactylaria Candida,' (B2.58) Dilophosphora alopecuri (available as TWIST FUNGUS®);
  • B2.60 Pseudozyma flocculosa, strain PF- A22 UL (available as SPORODEX® L by Plant Products Co., CA); (B2.61)
  • strain ICC 080 IMI CC 392151 CABI
  • BIODERMA® AGROBIOSOL DE MEXICO, S.A. DE C.V.
  • B2.62 Trichoderma fertile (e.g. product TrichoPlus from BASF);
  • B2.63 Muscodor roseus, in particular strain A3-5 (Accession No. NRRL 30548);
  • Simplicillium lanosoniveunr, biological control agents having an effect for improving plant growth and/or plant health which may be combined in the compound combinations according to the invention including
  • (Cl) bacteria selected from the group consisting of (C1.01) Bacillus pumilus, in particular strain QST2808 (having Accession No. NRRL No. B-30087); (Cl.02) Bacillus subtilis, in particular strain QST713/AQ713 (having NRRL Accession No. B-21661 and described in U.S. Patent No. 6,060,051; available as SERENADE® OPTI or SERENADE® ASO from Bayer CropScience LP, US); (C1.03) Bacillus subtilis, in particular strain AQ30002 (having Accession Nos. NRRL B-50421 and described in U.S. Patent Application No.
  • Bacillus subtilis in particular strain AQ30004 (and NRRL B-50455 and described in U.S. Patent Application No. 13/330,576); (C.1.05) Sinorhizobium meliloti strain NRG-185-1 (NITRAGIN® GOLD from Bayer CropScience); (C.1.06) Bacillus subtilis strain BU1814, (available as TEQUALIS® from BASF SE); (C1.07) Bacillus subtilis rm303 (RHIZOMAX® from Biofilm Crop Protection); (C1.08) Bacillus amyloliquefaciens pm414 (LOLI- PEPTA® from Biofdm Crop Protection); (C1.09) Bacillus mycoides BT155 (NRRL No.
  • Bacillus mycoides EE118 (NRRL No. B-50918), (CLIO) Bacillus mycoides EE141 (NRRL No. B- 50916), Bacillus mycoides BT46-3 (NRRL No. B-50922), (Cl.l l) .Bacillus cereus family member EE128 (NRRL No. B-50917), (Cl.12) Bacillus thuringiensis BT013A (NRRL No. B-50924) also known as Bacillus thuringiensis 4Q7, (Cl.13) Bacillus cereus family member EE349 (NRRL No.
  • Bacillus amyloliquefaciens SB3281 ATCC # PTA-7542; WO 2017/205258
  • Bacillus amyloliquefaciens TJ1000 available as QUIKROOTS® from Novozymes
  • Bacillus firmus in particular strain CNMC 1-1582 (e.g. VOTIVO® from BASF SE)
  • Bacillus pumilus in particular strain GB34 (e.g.
  • YIELD SHIELD® from Bayer Crop Science, DE
  • Bacillus amyloliquefaciens in particular strain IN937a
  • Bacillus amyloliquefaciens in particular strain FZB42 (e.g. RHIZOVITAL® from ABiTEP, DE)
  • Bacillus amyloliquefaciens BS27 accesion No.
  • NRRL B-5015 a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available as QUARTZO® (WG), PRESENCE® (WP) from FMC Corporation);
  • C1.22 Bacillus cereus, in particular strain BP01 (ATCC 55675; e.g. MEPICHLOR® from Arysta Lifescience, US);
  • C1.23 Bacillus subtilis, in particular strain MBI 600 (e.g. SUBTILEX® from BASF SE);
  • Bradyrhizobium japonicum e.g.
  • strain Z25 (Accession No. CECT 4585); (C1.35) Azorhizobium caulinodans, in particular strain ZB-SK-5; (C1.36) Azotobacter chroococcum, in particular strain H23; (C1.37) Azotobacter vinelandii, in particular strain ATCC 12837; (C1.38) Bacillus siamensis, in particular strain KCTC 13613T; (C1.39) Bacillus tequilensis, in particular strain NII-0943; (C1.40) Serratia marcescens, in particular strain SRM (Accession No. MTCC 8708); (C1.41) Thiobacillus sp. (e.g. CROPAID® from Cropaid Ltd UK); and
  • (C2) fungi selected from the group consisting of (C2.01) Purpureocillium lilacinum (previously known as Paecilomyces lilacinus) strain 251 (AGAL 89/030550; e.g. BioAct from Bayer CropScience Biologies GmbH); (C2.02) Penicillium bilaii, strain ATCC 22348 (e.g. JumpStart® from Acceleron BioAg), (C2.03) Talaromyces flavus, strain VI 17b; (C2.04) Trichoderma atroviride strain CNCM 1-1237 (e.g. Esquive® WP from Agrauxine, FR), (C2.05) Trichoderma viride, e.g.
  • C2.01 Purpureocillium lilacinum (previously known as Paecilomyces lilacinus) strain 251 (AGAL 89/030550; e.g. BioAct from Bayer CropScience Biologie
  • strain B35 (Pietr et al., 1993, Zesz. Nauk. A R w Szczecinie 161: 125-137); (C2.06) Trichoderma atroviride strain LC52 (also known as Trichoderma atroviride strain LU132; e.g. Sentinel from Agrimm Technologies Limited); (C2.07) Trichoderma atroviride strain SCI described in International Application No. PCT/IT2008/000196); (C2.08) Trichoderma asperellum strain kd (e.g.
  • T-Gro from Andermatt Biocontrol (C2.09) Trichoderma asperellum strain Eco-T (Plant Health Products, ZA); (C2.10) Trichoderma harzianum strain T-22 (e.g. Trianum-P from Andermatt Biocontrol or Koppert); (C2.l l) Myrothecium verrucarici strain AARC-0255 (e.g. DiTeraTM from Valent Biosciences); (C2.12) Penicillium bilaii strain ATCC ATCC20851; (C2.13) Pythium oligandrum strain Ml (ATCC 38472; e.g. Polyversum from Bioprepraty, CZ); (C2.14) Trichoderma virens strain GL-21 (e.g.
  • (DI) bacteria selected from the group consisting of (D1.01) Bacillus thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372; e.g. XENTARI® from Valent BioSciences); (DI.02) Bacillus mycoides, isolate J. (e.g. BmJ from Certis USA LLC, a subsidiary of Mitsui & Co.); (DI.03) Bacillus sphaericus, in particular Serotype H5a5b strain 2362 (strain ABTS-1743) (e.g. VECTOLEX® from Valent BioSciences, US); (DI.04) Bacillus thuringiensis subsp.
  • israelensis strain BMP 144 Bacillus thuringiensis israelensis strain BMP 144 (e.g.
  • Burkholderia spp. in particular Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI 305) (Accession No. NRRL B-50319; WO 2011/106491 and WO 2013/032693; e.g. MBI-206 TGAI and ZELTO® from Marrone Bio Innovations); (DI.10) Chromobacterium subtsugae, in particular strain PRAA4-1T (MBI- 203; e.g.
  • israeltaki strain EVB-113-19 (e.g., BIOPROTEC® from AEF Global); (DI.14) Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428; e.g. NOVODOR® FC from BioFa DE); (DI.15) Bacillus thuringiensis var. japonensis strain Buibui; (DI.16) Bacillus thuringiensis subsp. kurstaki strain ABTS 351; (DI.17) Bacillus thuringiensis subsp. kurstaki strain PB 54; (DI.18) Bacillus thuringiensis subsp.
  • israeltaki strain SA 11 Bacillus thuringiensis subsp. kurstaki strain SA 12; (D1.20) Bacillus thuringiensis subsp. kurstaki strain EG 2348; (DI.21) Bacillus thuringiensis var. Colmeri (e.g. TIANBAOBTC by Changzhou Jianghai Chemical Factory); (DI.22) Bacillus thuringiensis subsp. aizawai strain GC-91; (DI.23) Serratia entomophila (e.g. INVADE® by Wrightson Seeds); (DI.24) Serratia marcescens, in particular strain SRM (Accession No. MTCC 8708); and (DI.25) Wolbachia pipientis ZAP strain (e.g., ZAP MALES® from MosquitoMate); and
  • (D2) fungi selected from the group consisting of (D2.01) Isaria fumosorosea (previously known as Paecilomyces fumosoroseus)' strain apopka 97; (D2.02) Beauveria bassiana strain ATCC 74040 (e.g. NATURALIS® from Intrachem Bio Italia); (D2.03) Beauveria bassiana strain GHA (Accession No. ATCC74250; e.g.
  • viruses selected from the group consisting of Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydia pomonella (codling moth) granulosis virus (GV), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua (beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV, and Spodoptera littoralis (African cotton leafworm) NPV;
  • (F) bacteria and fungi which can be added as 'inoculant' to plants or plant parts or plant organs and which, by virtue of their particular properties, promote plant growth and plant health.
  • Examples are: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., in particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp.
  • G plant extracts and products formed by microorganisms including proteins and secondary metabolites which can be used as biological control agents, such as Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum/Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, "Requiem TM Insecticide", rotenone, /w/ «/ryanodinc.
  • Allium sativum Artemisia absinthium, azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelmin
  • Symphytum officinale Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract, in particular oilseed rape powder or mustard powder, as well as bioinsecticidal / acaricidal active substances obtained from olive oil, in particular unsaturated fatty/carboxylic acids having carbon chain lengths C16-C20 as active ingredients, such as, for example, contained in the product with the trade name FLiPPER®.
  • the compound used according to the invention and the composition of the invention may be combined with one or more active ingredients selected from insecticides, acaricides and nematicides.
  • Insecticides as well as the term “insecticidal” refers to the ability of a substance to increase mortality or inhibit growth rate of insects. As used herein, the term “insects” comprises all organisms in the class “Insecta”.
  • nematode and “nematicidal” refers to the ability of a substance to increase mortality or inhibit the growth rate of nematodes.
  • nematode comprises eggs, larvae, juvenile and mature forms of said organism.
  • Acaricide and “acaricidal” refers to the ability of a substance to increase mortality or inhibit growth rate of ectoparasites belonging to the class Arachnida, sub-class Acari.
  • insecticides examples include insecticides, acaricides and nematicides, respectively, which could be mixed with the compound used according to the invention and the composition of the invention are:
  • Acetylcholinesterase (AChE) inhibitors such as, for example, carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, for example acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifo
  • GABA-gated chloride channel blockers such as, for example, cyclodiene-organochlorines, for example chlordane and endosulfan or phenylpyrazoles (fiproles), for example ethiprole and fipronil.
  • Sodium channel modulators such as, for example, pyrethroids, e.g. acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer, biore smethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR)-trans-isomer], deltamethrin, empenthrin [(EZ)-(lR)-
  • Nicotinic acetylcholine receptor (nAChR) competitive modulators such as, for example, neonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • neonicotinoids e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • Nicotinic acetylcholine receptor (nAChR) allosteric modulators such as, for example, spinosyns, e.g. spinetoram and spinosad.
  • Glutamate -gated chloride channel (GluCl) allosteric modulators such as, for example, avermectins/milbemycins, for example abamectin, emamectin benzoate, lepimectin and milbemectin.
  • Juvenile hormone mimics such as, for example, juvenile hormone analogues, e.g. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.
  • Miscellaneous non-specific (multi-site) inhibitors such as, for example, alkyl halides, e.g. methyl bromide and other alkyl halides; or chloropicrine or sulphuryl fluoride or borax or tartar emetic or methyl isocyanate generators, e.g. diazomet and metam.
  • alkyl halides e.g. methyl bromide and other alkyl halides
  • chloropicrine or sulphuryl fluoride or borax or tartar emetic or methyl isocyanate generators e.g. diazomet and metam.
  • Mite growth inhibitors such as, for example clofentezine, hexythiazox and diflovidazin or etoxazole.
  • Microbial disruptors of the insect gut membrane such as, for example Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenehrionis, and B.t. plant proteins: CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Abl/35Abl.
  • Inhibitors of mitochondrial ATP synthase such as, ATP disruptors such as, for example, diafenthiuron or organotin compounds, for example azocyclotin, cyhexatin and fenbutatin oxide or propargite or tetradifon.
  • ATP disruptors such as, for example, diafenthiuron or organotin compounds, for example azocyclotin, cyhexatin and fenbutatin oxide or propargite or tetradifon.
  • Nicotinic acetylcholine receptor channel blockers such as, for example, bensultap, cartap hydrochloride, thiocylam, and thiosultap-sodium.
  • Inhibitors of chitin biosynthesis type 0, such as, for example, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • Inhibitors of chitin biosynthesis type 1, for example buprofezin.
  • Moulting disruptor in particular for Diptera, i.e. dipterans, such as, for example, cyromazine.
  • Ecdysone receptor agonists such as, for example, chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
  • Octopamine receptor agonists such as, for example, amitraz.
  • Mitochondrial complex III electron transport inhibitors such as, for example, hydramethylnone or acequinocyl or fluacrypyrim.
  • Mitochondrial complex I electron transport inhibitors such as, for example from the group of the METI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).
  • METI acaricides e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).
  • Voltage-dependent sodium channel blockers such as, for example indoxacarb or metaflumizone.
  • Inhibitors of acetyl CoA carboxylase such as, for example, tetronic and tetramic acid derivatives, e.g. spirodiclofen, spiromesifen and spirotetramat.
  • Mitochondrial complex IV electron transport inhibitors such as, for example, phosphines, e.g. aluminium phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides, e.g. calcium cyanide, potassium cyanide and sodium cyanide.
  • Mitochondrial complex II electron transport inhibitors such as, for example, 6eto-ketonitrile derivatives, e.g. cyenopyrafen and cyflumetofen and carboxanilides, such as, for example, pyflubumide.
  • Ryanodine receptor modulators such as, for example, diamides, e.g. chlorantraniliprole, cyantraniliprole and flubendiamide, further active compounds such as, for example, Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Broflanilide, Bromopropylate, Chinomethionat, Chloroprallethrin, Cryolite, Cyclaniliprole, Cycloxaprid, Cyhalodiamide, Dicloromezotiaz, Dicofol, epsilon-Metofluthrin, epsilon- Momfluthrin, Flometoquin, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Fluralaner, Fluxamet
  • WO 2007040280 Al, WO 2007040282 Al (CAS 934001-66-8), N-[3-chloro-l-(3-pyridinyl)-lH- pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]-propanamide (known from WO 2015/058021 Al, WO 2015/058028 Al) (CAS 1477919-27-9) and N-[4-(aminothioxomethyl)-2-methyl-6- [(methylamino)carbonyl]phenyl]-3-bromo-l-(3-chloro-2-pyridinyl)-lH-pyrazole-5-carboxamide (known from CN 103265527 A) (CAS 1452877-50-7), 5-(l,3-dioxan-2-yl)-4-[[4-(trifluoromethyl)phenyl] methoxy] -pyrimidine (known from WO
  • O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylphosphoramidothioate, halauxifen, halauxifen-methyl ,halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e.
  • plant growth regulators which could be mixed with the compound used according to the invention and the composition of the invention are:
  • safeners which could be mixed with the compound used according to the invention and the composition of the invention are, for example, benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr
  • nitrification inhibitors wich can be mixed with the compound used according to the invention and the composition of the invention are selected from the group consisting of 2-(3,4- dimethyl-1 H-pyrazol-1 -yl)succinic acid, 2-(4, 5 -dimethyl- 1 H-pyrazol-1 -yl)succinic acid, 3,4-dimethyl pyrazolium glycolate, 3,4-dimethyl pyrazolium citrate, 3,4-dimethyl pyrazolium lactate, 3,4-dimethyl pyrazolium mandelate, 1 ,2,4-triazole, 4-Chloro-3-methylpyrazole, N-((3(5)-methyl-lH-pyrazole-l- yl)methyl)acetamide, N-((3(5)-methyl-l H-pyrazole-l-yl)methyl)formamide, N-((3(5),4- dimethylpyrazole-l-yl)methyl)formamide, N-((4-chlor
  • the compound used according to the invention and the composition of the invention may be combined with one or more agriculturally beneficial agents.
  • agriculturally beneficial agents include biostimulants, plant growth regulators, plant signal molecules, growth enhancers, microbial stimulating molecules, biomolecules, soil amendments, nutrients, plant nutrient enhancers such as lipo-chitooligosaccharides (LCO), chitooligosaccharides (CO), chitinous compounds, flavonoids, jasmonic acid or derivatives thereof (e.g., jasmonates), cytokinins, auxins, gibberellins, absiscic acid, ethylene, brassinosteroids, salicylates, macro- and micronutrients, linoleic acid or derivatives thereof, linolenic acid or derivatives thereof, karrikins, and beneficial microorganisms (e.g., Rhizobium spp., Bradyrhizobium spp., Sinorhizobium spp., Azorhizobium spp., Glomus spp., Gigaspora spp., Hy
  • the compound used according to the invention and the composition of the invention have potent microbicidal activity and/or plant defense modulating potential. They can be used for controlling unwanted microorganisms, such as unwanted fungi and bacteria, on plants. They can be particularly useful in crop protection (they control microorganisms that cause plants diseases) or for protecting materials (e.g. industrial materials, timber, storage goods) as described in more details herein below. More specifically, the compound used according to the invention and the composition of the invention can be used to protect seeds, germinating seeds, emerged seedlings, plants, plant parts, fruits, harvest goods and/or the soil in which the plants grow from unwanted microorganisms.
  • Control or controlling as used herein encompasses protective, curative and eradicative treatment of unwanted microorganisms.
  • Unwanted microorganisms may be pathogenic bacteria, pathogenic virus, pathogenic oomycetes or pathogenic fungi, more specifically phytopathogenic bacteria, phytopathogenic virus, phytopathogenic oomycetes or phytopathogenic fungi. As detailed herein below, these phytopathogenic microorganims are the causal agents of a broad spectrum of plants diseases.
  • the compound used according to the invention and the composition of the invention can be used as fungicides.
  • fungicide refers to a compound or composition that can be used in crop protection for the control of unwanted fungi, such as Plasmodiophoromycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes and/or for the control of Oomycetes.
  • the compound used according to the invention and the composition of the invention may also be used as antibacterial agent.
  • they may be used in crop protection, for example for the control of unwanted bacteria, such as Pseudomonadaceae, Rhizobiaceae, Xanthomonadaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • the compound used according to the invention and the composition of the invention may also be used as antiviral agent in crop protection.
  • the compound and the composition of the invention may have effects on diseases from plant viruses, such as the tobacco mosaic virus (TMV), tobacco rattle virus, tobacco stunt virus (TStuV), tobacco leaf curl virus (VLCV), tobacco nervilia mosaic virus (TVBMV), tobacco necrotic dwarf virus (TNDV), tobacco streak virus (TSV), potato virus X (PVX), potato viruses Y, S, M, and A, potato acuba mosaic virus (PAMV), potato mop-top virus (PMTV), potato leaf-roll virus (PLRV), alfalfa mosaic virus (AMV), cucumber mosaic virus (CMV), cucumber green mottlemosaic virus (CGMMV), cucumber yellows virus (CuYV), watermelon mosaic virus (WMV), tomato spotted wilt virus (TSWV), tomato ringspot virus (TomRSV), sugarcane mosaic virus (SCMV), rice drawf virus, rice stripe virus, rice black-streaked draw
  • the present invention also relates to a method for controlling unwanted microorganisms, such as unwanted fungi, oomycetes and bacteria, on plants comprising the step of applying at least one compound of the invention or at least one composition of the invention to the microorganisms and/or their habitat (to the plants, plant parts, seeds, fruits or to the soil in which the plants grow).
  • unwanted microorganisms such as unwanted fungi, oomycetes and bacteria
  • Suitable substrates that may be used for cultivating plants include inorganic based substrates, such as mineral wool, in particular stone wool, perlite, sand or gravel; organic substrates, such as peat, pine bark or sawdust; and petroleum based substrates such as polymeric foams or plastic beads.
  • Effective and plant-compatible amount means an amount that is sufficient to control or destroy the fungi present or liable to appear on the cropland and that does not entail any appreciable symptom of phytotoxicity for said crops. Such an amount can vary within a wide range depending on the fungus to be controlled, the type of crop, the crop growth stage, the climatic conditions and the respective compound or composition of the invention used. This amount can be determined by systematic field trials that are within the capabilities of a person skilled in the art.
  • the compound used according to the invention and the composition of the invention may be applied to any plants or plant parts.
  • Plants mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants may 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 genetically modified plants (GMO or transgenic plants) and the plant cultivars which are protectable and non-protectable by plant breeders’ rights.
  • Plant cultivars are understood to mean plants which have new properties ("traits”) and have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.
  • Plant parts are understood to mean all parts and organs of plants above and below the ground, such as shoots, leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes.
  • the plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.
  • Plants which may be treated in accordance with the methods of the invention include the following: cotton, flax, grapevine, fruit, vegetables, such as Rosaceae sp. (for example pome fruits such as apples and pears, but also stone fruits such as apricots, cherries, almonds and peaches, and soft fruits such as strawberries), Ribesioidae sp. , Juglandaceae sp., Betulacecie sp. , Anaccirdicicecie sp., Fagaceae sp.,Moraceae sp., Oleacecie sp. , Actinidacecie sp. , Laurcicecie sp. , Musaceae sp.
  • Rosaceae sp. for example pome fruits such as apples and pears, but also stone fruits such as apricots, cherries, almonds and peaches, and soft fruits such as strawberries
  • Rosaceae sp. for example pome fruits such as apples
  • Rubiacecie sp. for example coffee
  • Theacecie sp. Sterculiceae sp., Rutaceae sp. (for example lemons, oranges and grapefruit); Solancicecie sp. (for example tomatoes), Liliacecie sp., Asteraceae sp. (for example lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiacecie sp., Cucurbitaceae sp. (for example cucumber), Alliacecie sp. (for example leek, onion), Papilioncicecie sp. (for example peas); major crop plants, such as Graminecie sp.
  • Asteraceae sp. for example sunflower
  • Brassicaceae sp. for example white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and oilseed rape, mustard, horseradish and cress
  • Fabacae sp. for example bean, peanuts
  • Papilionaceae sp. for example soya bean
  • Solanaceae sp. for example potatoes
  • Chenopodiaceae sp. for example sugar beet, fodder beet, swiss chard, beetroot
  • useful plants and ornamental plants for gardens and wooded areas and genetically modified varieties of each of these plants.
  • Plants and plant cultivars which may be treated by the above disclosed methods include plants and plant cultivars which are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids.
  • Plants and plant cultivars which may be treated by the above disclosed methods include those plants which are resistant to one or more abiotic stresses.
  • Abiotic stress conditions may include, for example, drought, cold temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance.
  • Plants and plant cultivars which may be treated by the above disclosed methods include those plants characterized by enhanced yield characteristics. Increased yield in said plants may be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation.
  • Yield may furthermore be affected by improved plant architecture (under stress and non-stress conditions), including but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance.
  • Further yield traits include seed composition, such as carbohydrate content and composition for example cotton or starch, protein content, oil content and composition, nutritional value, reduction in anti-nutritional compounds, improved processability and better storage stability.
  • Plants and plant cultivars which may be treated by the above disclosed methods include plants and plant cultivars which are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stresses.
  • the compound used according to the invention can be advantageously used to treat transgenic plants, plant cultivars or plant parts that received genetic material which imparts advantageous and/or useful properties (traits) to these plants, plant cultivars or plant parts. Therefore, it is contemplated that the present invention may be combined with one or more recombinant traits or transgenic event(s) or a combination thereof.
  • a transgenic event is created by the insertion of a specific recombinant DNA molecule into a specific position (locus) within the chromosome of the plant genome.
  • the insertion creates a novel DNA sequence referred to as an “event” and is characterized by the inserted recombinant DNA molecule and some amount of genomic DNA immediately adjacent to/flanking both ends of the inserted DNA.
  • trait(s) or transgenic event(s) include, but are not limited to, pest resistance, water use efficiency, yield performance, drought tolerance, seed quality, improved nutritional quality, hybrid seed production, and herbicide tolerance, in which the trait is measured with respect to a plant lacking such trait or transgenic event.
  • Such advantageous and/or useful properties are better plant growth, vigor, stress tolerance, standability, lodging resistance, nutrient uptake, plant nutrition, and/or yield, in particular improved growth, increased tolerance to high or low temperatures, increased tolerance to drought or to levels of water or soil salinity, enhanced flowering performance, easier harvesting, accelerated ripening, higher yields, higher quality and/or a higher nutritional value of the harvested products, better storage life and/or processability of the harvested products, and increased resistance against animal and microbial pests, such as against insects, arachnids, nematodes, mites, slugs and snails.
  • Bt Cry or VIP proteins which include the CrylA, CrylAb, CrylAc, CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF proteins or toxic fragments thereof and also hybrids or combinations thereof, especially the CrylF protein or hybrids derived from a CrylF protein (e.g. hybrid CrylA- CrylF proteins or toxic fragments thereof), the CrylA-type proteins or toxic fragments thereof, preferably the CrylAc protein or hybrids derived from the CrylAc protein (e.g.
  • hybrid CrylAb-CrylAc proteins or the CrylAb or Bt2 protein or toxic fragments thereof, the Cry2Ae, Cry2Af or Cry2Ag proteins or toxic fragments thereof, the CrylA. 105 protein or a toxic fragment thereof, the VIP3Aal9 protein, the VIP3Aa20 protein, the VIP3A proteins produced in the COT202 or COT203 cotton events, the VIP3Aa protein ora toxic fragment thereof as described in Estruch et al. (1996), Proc Natl Acad Sci US A.
  • herbicides for example imidazolinones, sulphonylureas, glyphosate or phosphinothricin.
  • DNA sequences encoding proteins which confer properties of tolerance to certain herbicides on the transformed plant cells and plants mention will be particularly be made to the bar or PAT gene or the Streptomyces coelicolor gene described in WO2009/152359 which confers tolerance to glufosinate herbicides, a gene encoding a suitable EPSPS (5 -Enolpyruvylshikimat-3 -phosphat-synthase) which confers tolerance to herbicides having EPSPS as a target, especially herbicides such as glyphosate and its salts, a gene encoding glyphosate-n-acetyltransferase, or a gene encoding glyphosate oxidoreductase.
  • EPSPS -Enolpyruvylshikimat-3 -phosphat-s
  • herbicide tolerance traits include at least one ALS (acetolactate synthase) inhibitor (e.g. W02007/024782), a mutated Arabidopsis ALS/AHAS gene (e.g. U.S. Patent 6,855,533), genes encoding 2,4-D-monooxygenases conferring tolerance to 2,4-D (2,4- dichlorophenoxyacetic acid) and genes encoding Dicamba monooxygenases conferring tolerance to dicamba (3,6-dichloro-2- methoxybenzoic acid).
  • ALS acetolactate synthase
  • W02007/024782 e.g. W02007/024782
  • a mutated Arabidopsis ALS/AHAS gene e.g. U.S. Patent 6,855,533
  • Yet another example of such properties is resistance to one or more phytopathogenic fungi, for example Asian Soybean Rust.
  • DNA sequences encoding proteins which confer properties of resistance to such diseases mention will particularly be made of the genetic material from glycine tomentella, for example from any one of publically available accession lines PI441001 , PI483224, PI583970, PI446958, PI499939, PI505220, PI499933, PI441008, PI505256 or PI446961 as described in W02019/103918.
  • SAR systemic acquired resistance
  • phytoalexins phytoalexins
  • elicitors resistance genes and correspondingly expressed proteins and toxins.
  • Particularly useful transgenic events in transgenic plants or plant cultivars which can be treated with preference in accordance with the invention include Event 531/ PV-GHBK04 (cotton, insect control, described in W02002/040677), Event 1143-14A (cotton, insect control, not deposited, described in WO2006/128569); Event 1143-5 IB (cotton, insect control, not deposited, described in W02006/128570); Event 1445 (cotton, herbicide tolerance, not deposited, described in US-A 2002- 120964 or W02002/034946); Event 17053 (rice, herbicide tolerance, deposited as PTA-9843, described in WO2010/117737); Event 17314 (rice, herbicide tolerance, deposited as PTA-9844, described in WO2010/117735); Event 281-24-236 (cotton, insect control - herbicide tolerance, deposited as PTA-6233, described in W02005/103266 or US-A 2005-216969); Event 3006-210-23 (cotton, insect control - herb
  • Event BLR1 (oilseed rape, restoration of male sterility, deposited as NCIMB 41193, described in W02005/074671), Event CE43-67B (cotton, insect control, deposited as DSM ACC2724, described in US-A 2009-217423 or WO2006/128573); Event CE44-69D (cotton, insect control, not deposited, described in US-A 2010- 0024077); Event CE44- 69D (cotton, insect control, not deposited, described in WO2006/128571); Event CE46-02A (cotton, insect control, not deposited, described in WO2006/128572); Event COT102 (cotton, insect control, not deposited, described in US-A 2006-130175 or W02004/039986); Event COT202 (cotton, insect control, not deposited, described in US-A 2007-067868 or W02005/054479); Event COT203 (cotton, insect control, not deposited,
  • transgenic event(s) is provided by the United States Department of Agriculture’s (USDA) Animal and Plant Health Inspection Service (APHIS) and can be found on their website on the world wide web at aphis.usda.gov. For this application, the status of such list as it is/was on the filing date of this application, is relevant.
  • USDA United States Department of Agriculture
  • APIHIS Animal and Plant Health Inspection Service
  • transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice, triticale, barley, rye, oats), maize, soya beans, potatoes, sugar beet, sugar cane, tomatoes, peas and other types of vegetable, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), with particular emphasis being given to maize, soya beans, wheat, rice, potatoes, cotton, sugar cane, tobacco and oilseed rape.
  • Traits which are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and slugs and snails, as well as the increased resistance of the plants to one or more herbicides.
  • Non-limiting examples of pathogens of fungal diseases which may be treated in accordance with the invention include: diseases caused by powdery mildew pathogens, for example Blumeria species, for example Blumeria graminis,' Podosphaera species, for example Podosphaera leucotricha,' Sphaerotheca species, for example Sphaerotheca fuliginea,' Uncinula species, for example Uncinula necator, diseases caused by rust disease pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae,' Hemileia species, for example Hemileia vastatrix,' Phakopsora species, for example Phakopsora pachyrhizi, Phakopsora meihomiae or Phakopsora euvitis,' Puccinia species, for example Puccinia recondita, Puccinia graminis oder Puccinia striiform
  • brassicae ' Phytophthora species, for example Phytophthora infestans,' Plasmopara species, for example Plasmopara viticokr, Pseudoperonospora species, for example Pseudoperonospora humuli or Pseudoperonospora cubensis,' Pythium species, for example Pythium ultimunr, leaf blotch diseases and leaf wilt diseases caused, for example, by Altemaria species, for example Alternaria solani,' Cercospora species, for example Cercospora beticola,' Cladiosporium species, for example Cladiosporium cucumerinurm, Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus,' Colletotrichum species, for example Colletotric
  • Colletotrichum species for example Colletotrichum coccodes,' Fusarium species, for example Fusarium culmorunr, Gibberella species, for example Gibberella zeae Macrophomina species, for example Macrophomina phaseolina,' Microdochium species, for example Microdochium nivalc, Monographella species, for example Monographella nivalis,' Penicillium species, for example Penicillium expansum,' Phoma species, for example Phoma lingam,' Phomopsis species, for example Phomopsis sojac, Phytophthora species, for example Phytophthora cactorunr, Pyrenophora species, for example Pyrenophora graminea,' Pyricularia species, for example Pyricularia oryzac, Pythium species, for example Pythium ultimurrr, Rhizoctonia species, for example Rhizoctonia solani,' Rhizopus species, for example Rhizopus or
  • Pseudomonas species for example Pseudomonas syringae pv. lachrymans,' Erwinia species, for example Erwinia amylovora,' Liberibacter species, for example Liberibacter asiaticus,' Xyella species, for example Xylella fastidiosa,' Ralstonia species, for example Ralstonia solanacearum,' Dickeya species, for example Dickeya solani,' Clavibacter species, for example Clavibacter michiganensis,' Streptomyces species, for example Streptomyces scabies. diseases of soya beans:
  • Altemaria leaf spot Altemaria spec, atrans tenuissima
  • Anthracnose (('olleioirichum gloeosporoides dematium var.
  • phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia southern blight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola).
  • the compound used according to the invention and the composition of the invention may reduce the mycotoxin content in the harvested material and the foods and feeds prepared therefrom.
  • Mycotoxins include particularly, but not exclusively, the following: deoxynivalenol (DON), nivalenol, 15 -Ac-DON, 3 -Ac-DON, T2- and HT2 -toxin, fumonisins, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins which can be produced, for example, by the following fungi: Fusarium spec., such as F.
  • verticillioides and also by Aspergillus spec., such as A. flavus, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spec., such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps spec., such as C. purpurea, C. fusiformis, C. paspali, C. africana, Stachybotrys spec, and others.
  • Aspergillus spec. such as A. flavus, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spec., such as P. verrucosum, P. viridicatum, P. citr
  • the compound and the composition of the invention may also be used in the protection of materials, especially for the protection of industrial materials against attack and destruction by phytopathogenic fungi.
  • the compound and the composition of the invention may be used as antifouling compositions, alone or in combinations with other active ingredients.
  • Industrial materials in the present context are understood to mean inanimate materials which have been prepared for use in industry.
  • industrial materials which are to be protected from microbial alteration or destruction may be adhesives, glues, paper, wallpaper and board/cardboard, textiles, carpets, leather, wood, fibers and tissues, paints and plastic articles, cooling lubricants and other materials which can be infected with or destroyed by microorganisms.
  • Parts of production plants and buildings, for example cooling-water circuits, cooling and heating systems and ventilation and air-conditioning units, which may be impaired by the proliferation of microorganisms may also be mentioned within the scope of the materials to be protected.
  • Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and card, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood.
  • the compound and the composition of the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
  • the compound and the composition of the invention may also be used against fungal diseases liable to grow on or inside timber.
  • Timber means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood.
  • the compound and the composition of the invention may be used to protect objects which come into contact with saltwater or brackish water, especially hulls, screens, nets, buildings, moorings and signalling systems, from fouling.
  • the compound and the composition of the invention may also be employed for protecting storage goods.
  • Storage goods are understood to mean natural substances of vegetable or animal origin or processed products thereof which are of natural origin, and for which long-term protection is desired.
  • Storage goods of vegetable origin for example plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, may be protected freshly harvested or after processing by (pre)drying, moistening, comminuting, grinding, pressing or roasting.
  • Storage goods also include timber, both unprocessed, such as construction timber, electricity poles and barriers, or in the form of finished products, such as furniture.
  • Storage goods of animal origin are, for example, hides, leather, furs and hairs.
  • the compound and the composition of the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
  • Microorganisms capable of degrading or altering industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms.
  • the compound and the composition of the invention preferably act against fungi, especially moulds, wood-discoloring and wood-destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), and against slime organisms and algae.
  • microorganisms of the following genera Altemaria, such as Alternarici tenuis,' Aspergillus, such as Aspergillus niger, Chaetomium, such as Chaetomium globosunr, Coniophora, such as Coniophora puetana, Lentinus, such as Lentinus tigrinus,' Penicillium, such as Penicillium glaucunr, Polyporus, such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans,' Sclerophoma, such as Sclerophoma pityophilcr, Trichoderma, such as Trichoderma viridc, Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus
  • the compound used according to the invention and the composition of the invention may also be used to protect seeds from unwanted microorganisms, such as phytopathogenic microorganisms, for instance phytopathogenic fungi or phytopathogenic oomycetes.
  • seed(s) as used herein include dormant seeds, primed seeds, pregerminated seeds and seeds with emerged roots and leaves.
  • the present invention also relates to a method for protecting seeds from unwanted microorganisms which comprises the step of treating the seeds with the compound used according to the invention or the composition of the invention.
  • the treatment of seeds with the compound or the composition of the invention protects the seeds from phytopathogenic microorganisms, but also protects the germinating seeds, the emerging seedlings and the plants after emergence from the treated seeds. Therefore, the present invention also relates to a method for protecting seeds, germinating seeds and emerging seedlings.
  • the seeds treatment may be performed prior to sowing, at the time of sowing or shortly thereafter.
  • the seeds treatment may be performed as follows: the seeds may be placed into a mixer with a desired amount of the compound or the composition of the invention, the seeds and the compound or the composition of the invention are mixed until an homogeneous distribution on seeds is achieved. If appropriate, the seeds may then be dried.
  • the invention also relates to seeds coated with the compound or the composition of the invention.
  • the seeds are treated in a state in which it is sufficiently stable for no damage to occur in the course of treatment.
  • seeds can be treated at any time between harvest and shortly after sowing. It is customary to use seeds which have been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. For example, it is possible to use seeds which have been harvested, cleaned and dried down to a moisture content of less than 15% by weight. Alternatively, it is also possible to use seeds which, after drying, for example, have been treated with water and then dried again, or seeds just after priming, or seeds stored in primed conditions or pre-germinated seeds, or seeds sown on nursery trays, tapes or paper.
  • the amount of the compound used according to the invention or the composition of the invention applied to the seeds is typically such that the germination of the seed is not impaired, or that the resulting plant is not damaged. This must be ensured particularly in case the the compound of the invention would exhibit phytotoxic effects at certain application rates.
  • the intrinsic phenotypes of transgenic plants should also be taken into consideration when determining the amount of the compound used according to the invention to be applied to the seed in order to achieve optimum seed and germinating plant protection with a minimum amount of compound being employed.
  • the compound of the invention can be applied as such, directly to the seeds, i.e. without the use of any other components and without having been diluted. Also the composition of the invention can be applied to the seeds.
  • the compound and the composition of the invention are suitable for protecting seeds of any plant variety.
  • Preferred seeds are that of cereals (such as wheat, barley, rye, millet, triticale, and oats), oilseed rape, maize, cotton, soybean, rice, potatoes, sunflower, beans, coffee, peas, beet (e.g. sugar beet and fodder beet), peanut, vegetables (such as tomato, cucumber, onions and lettuce), lawns and ornamental plants. More preferred are seeds of wheat, soybean, oilseed rape, maize and rice.
  • the compound used according to the invention and the composition of the invention may be used for treating transgenic seeds, in particular seeds of plants capable of expressing a polypeptide or protein which acts against pests, herbicidal damage or abiotic stress, thereby increasing the protective effect.
  • Seeds of plants capable of expressing a polypeptide or protein which acts against pests, herbicidal damage or abiotic stress may contain at least one heterologous gene which allows the expression of said polypeptide or protein.
  • These heterologous genes in transgenic seeds may originate, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • These heterologous genes preferably originate from Bacillus sp., in which case the gene product is effective against the European com borer and/or the Western com rootworm.
  • the heterologous genes originate from Bacillus thuringiensis.
  • the compound used according to the invention can be applied as such, or for example in the form of as ready-to-use solutions, emulsions, water- or oil-based suspensions, powders, wettable powders, pastes, soluble powders, dusts, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural products impregnated with the compound of the invention, synthetic substances impregnated with the compound of the invention, fertilizers or microencapsulations in polymeric substances.
  • Application is accomplished in a customary manner, for example by watering, spraying, atomizing, broadcasting, dusting, foaming or spreading-on. It is also possible to deploy the compound of the invention by the ultra-low volume method, via a drip irrigation system or drench application, to apply it in-furrow or to inject it into the soil stem or trunk. It is further possible to apply the compound of the invention by means of a wound seal, paint or other wound dressing.
  • the effective and plant-compatible amount of the compound used according to the invention which is applied to the plants, plant parts, fruits, seeds or soil will depend on various factors, such as the compound/composition employed, the subject of the treatment (plant, plant part, fruit, seed or soil), the type of treatment (dusting, spraying, seed dressing), the purpose of the treatment (curative and protective), the type of microorganisms, the development stage of the microorganisms, the sensitivity of the microorganisms, the crop growth stage and the environmental conditions.
  • the application rates can vary within a relatively wide range, depending on the kind of application.
  • the application rate may range from 0.1 to 10 000 g/ha, preferably from 10 to 1000 g/ha, more preferably from 50 to 300 g/ha (in the case of application by watering or dripping, it is even possible to reduce the application rate, especially when inert substrates such as rockwool or perlite are used).
  • the application rate may range from 0.1 to 200 g per 100 kg of seeds, preferably from 1 to 150 g per 100 kg of seeds, more preferably from 2.5 to 25 g per 100 kg of seeds, even more preferably from 2.5 to 12.5 g per 100 kg of seeds.
  • the application rate may range from 0.1 to 10 000 g/ha, preferably from 1 to 5000 g/ha.
  • the compound used according to the invention and the composition of the invention can be used in combination with models e.g. embedded in computer programs for site specific crop management, satellite farming, precision farming or precision agriculture.
  • models support the site specific management of agricultural sites with data from various sources such as soils, weather, crops (e.g. type, growth stage, plant health), weeds (e.g. type, growth stage), diseases, pests, nutrients, water, moisture, biomass, satellite data or yield with the purpose to optimize profitability, sustainability and protection of the environment.
  • crops e.g. type, growth stage, plant health
  • weeds e.g. type, growth stage
  • diseases, pests, nutrients, water, moisture, biomass, satellite data or yield with the purpose to optimize profitability, sustainability and protection of the environment.
  • such models can help to optimize agronomical decisions, control the precision of pesticide applications and record the work performed.
  • the compound used according to the invention can be applied to a crop plant according to appropriate dose regime if a model models the development of a fungal disease and calculates that a threshold has been reached for which it is recommendable to apply the compound of the invention to the crop plant.
  • the compound used according to the invention can also be used in combination with smart spraying equipment such as e.g. spot spraying or precision spraying equipment attached to or housed within a farm vehicle such as a tractor, robot, helicopter, airplane or unmanned aerial vehicle (UAV) such as a drone.
  • a farm vehicle such as a tractor, robot, helicopter, airplane or unmanned aerial vehicle (UAV) such as a drone.
  • UAV unmanned aerial vehicle
  • Such an equipment usually includes input sensors (such as e.g. a camera) and a processing unit configured to analyze the input data and configured to provide a decision based on the analysis of the input data to apply the compound of the invention to the crop plants (respectively the weeds) in a specific and precise manner.
  • the use of such smart spraying equipment usually also requires positions systems (e.g. GPS receivers) to localize recorded data and to guide or to control farm vehicles; geographic information systems (GIS) to represent the information on intelligible maps, and appropriate farm vehicles to perform the required farm action such as the
  • fungal diseases can be detected from imagery acquired by a camera.
  • fungal diseases can be identified and/or classified based on that imagery.
  • identification and/ classification can make use of image processing algorithms.
  • image processing algorithms can utilize machine learning algorithms, such as trained neutral networks, decision trees and utilize artificial intelligence algorithms. In this manner, the compounds described herein can be applied only where needed.
  • LogP value is determined by measurement of LC-UV, in an acidic range, with 0.1% formic acid in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).
  • p’ LogP value is determined by measurement of LC-UV, in a neutral range, with 0.001 molar ammonium acetate solution in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).
  • [cI LogP value is determined by measurement of LC-UV, in an acidic range, with 0.1% phosphoric acid and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).
  • 1H-NMR data of selected examples are written in form of IH-NMR-peak lists. To each signal peak are listed the 8-value in ppm and the signal intensity in round brackets. Between the 8-value - signal intensity pairs are semicolons as delimiters.
  • Intensity of sharp signals correlates with the height of the signals in a printed example of a NMR spectrum in cm and shows the real relations of signal intensities. From broad signals several peaks or the middle of the signal and their relative intensity in comparison to the most intensive signal in the spectrum can be shown.
  • tetramethylsilane For calibrating chemical shift for 1H spectra, we use tetramethylsilane and/or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO. Therefore in NMR peak lists, tetramethylsilane peak can occur but not necessarily.
  • the 1H-NMR peak lists are similar to classical 1H-NMR prints and contains therefore usually all peaks, which are listed at classical NMR-interpretation.
  • the peaks of stereoisomers of the target compounds and/or peaks of impurities have usually on average a lower intensity than the peaks of target compounds (for example with a purity >90%).
  • Such stereoisomers and/or impurities can be typical for the specific preparation process. Therefore their peaks can help to recognize the reproduction of our preparation process via “side-products-fmgerprints”.
  • An expert who calculates the peaks of the target compounds with known methods (MestreC, ACD- simulation, but also with empirically evaluated expectation values) can isolate the peaks of the target compounds as needed optionally using additional intensity filters. This isolation would be similar to relevant peak picking at classical 1H-NMR interpretation.
  • Table 1 illustrates in a non-limiting manner examples of compounds of formula (I) according to the invention:
  • the compounds of formula (I) which are mentioned in table 1 herein below were prepared in accordance with the procedures detailed herein below in connection with specific examples and with the general description of the processes herein disclosed.
  • Table 4 provides the NMR data (1H) of a selected number of compounds from tables 1, 2 and 3.
  • Step 2 Preparation of 6- ⁇ [l-(2-fhiorophenyl)cyclopropyl]amino ⁇ -N'-hydroxypyridine-3-carboximid- amide (Intermediate 11-003) according to process P2
  • Step 3 Preparation of N-[l-(2-fhiorophenyl)cyclopropyl]-5-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]pyridin-2 -amine (Compound 1-003) according to process Pl
  • Step 1 preparation of 5-fluoro-6-[[l-(2-fluorophenyl)cyclopropyl]amino]pyridine-3-carbonitrile (Intermediate III-014) according to process P7
  • Step 2 Preparation of 3-fluoro-N-[l-(2-fluorophenyl)cyclopropyl]-5-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]pyridin-2 -amine (Compound 1-020) according to process P2 and Pl
  • Step 1 preparation of 2- ⁇ [l-(2-fluorophenyl)cyclopropyl]amino ⁇ -l,3-thiazole-5-carbonitrile (Intermediate III-008) according to process P7
  • 2-bromo- 1,3 -thiazole-5 -carbonitrile 500.00 mg, 2.645 mmol, 1.00 equiv
  • 1- (2-fluorophenyl)cyclopropan-l -amine (479.87 mg, 3.174 mmol, 1.20 equiv) in Butanol (5.00 mb) was added TFA (150.80 mg, 1.323 mmol, 0.50 equiv) in portions at room temperature under nitrogen atmosphere.
  • Step 2 Preparation of N-[l-(2-fhiorophenyl)cyclopropyl]-5-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]thiazol-2 -amine (Compound 1-011) according to process P2 and Pl
  • Example 1 in vivo preventive test on Puccinia recondita (brown rust on wheat)
  • Emulsifier 1 pl of polyoxyethylene sorbitan monooleate (Tween® 80) per mg of active ingredient
  • the active ingredients were made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/ /Tween® 80 and then diluted in water to the desired concentration.
  • the young plants of wheat were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/ Tween® 80.
  • the plants were contaminated by spraying the leaves with an aqueous suspension of Puccinia recondita spores.
  • the contaminated wheat plants were incubated for 24 hours at 20°C and at 100% relative humidity and then for 9 days at 20°C and at 70-80% relative humidity.
  • the test was evaluated 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.
  • Example 2 in vivo preventive test on Phakospora pachyrhizi (soybean rust)
  • Emulsifier 1 pl of polyoxyethylene sorbitan monooleate (Tween® 80) per mg of active ingredient
  • the active ingredients were made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/ /Tween® 80 and then diluted in water to the desired concentration.
  • the young plants of soybean were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/ Tween® 80.
  • the plants were contaminated by spraying the leaves with an aqueous suspension of Phakospora pachyrhizi spores.
  • the contaminated soybean plants were incubated for 24 hours at 24°C and at 100% relative humidity and then for 10 days at 24°C and at 70-80% relative humidity.
  • Culture medium 14.6g anhydrous D-glucose (VWR), 7.1g Mycological Peptone (Oxoid), 1.4g granulated Yeast Extract (Merck), QSP 1 liter
  • Inoculum mycelial suspension
  • Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations.
  • the final concentration of DMSO used in the assay was ⁇ 1%.
  • Inoculum was prepared from a pre-culture of R. solani grown in liquid medium by homogenization using a blender. The concentration of ground mycelium in the inoculum was estimated and adjusted to the desired optical density (OD).
  • Fungicides were evaluated for their ability to inhibit mycelium growth in liquid culture assay.
  • the compounds were added in the desired concentrations to culture medium containing the mycelial suspension. After 5 days of incubation, the fungicidal efficacy of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.
  • Culture medium 14.6g anhydrous D-glucose (VWR), 7.1g Mycological Peptone (Oxoid), 1.4g granulated Yeast Extract (Merck), QSP lliter
  • Inoculum spores suspension
  • Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations.
  • the final concentration of DMSO used in the assay was ⁇ 1%.
  • a spore suspension of C. lindemuthianum was prepared and diluted to the desired spore density.
  • Fungicides were evaluated for their ability to inhibit spores germination and mycelium growth in liquid culture assay.
  • the compounds were added in the desired concentration to the culture medium with spores. After 6 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.
  • Example 5 in vivo preventive test on Phakoysora test (soybeans)
  • the plants remained in the incubation cabinet at approximately 24°C and a relative atmospheric humidity of approximately 80 % and a day / night interval of 12h.
  • Emulsifier 1 part by weight of polyoxyethylene sorbitan monooleate
  • the plants remained in the incubation cabinet at approximately 24°C and a relative atmospheric humidity of approximately 80 % and a day / night interval of 12h.
  • Example 7 in vivo longlasting activity test on Phakopsora test (soybeans)
  • Emulsifier 1 part by weight of polyoxyethylene sorbitan monooleate
  • the plants remained in the incubation cabinet at approximately 24°C and a relative atmospheric humidity of approximately 80 % and a day / night interval of 12h.

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Abstract

La présente invention concerne l'utilisation de composés 1,2,4-oxadiazole substitué par (hétéro)aryle pour lutter contre des micro-organismes nuisibles, en particulier des champignons phytopathogènes, dans la protection des cultures (formule (I)). L'invention concerne également de nouveaux composés de 1,2,4-oxadiazole substitués par (hétéro)aryle et des compositions les comprenant.
PCT/EP2021/085926 2020-12-18 2021-12-15 1,2,4-oxadiazoles substitués par (hétéro)aryle utilisés comme fongicides WO2022129190A1 (fr)

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Cited By (6)

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WO2023286855A1 (fr) * 2021-07-15 2023-01-19 クミアイ化学工業株式会社 Dérivé de formamide et agent de lutte contre les maladies des plantes agricoles ou horticoles
WO2024068520A1 (fr) 2022-09-28 2024-04-04 Bayer Aktiengesellschaft 3-(hétéro)aryl-5-chlorodifluorométhyl-1,2,4-oxadiazole utilisé comme fongicide
WO2024068518A1 (fr) 2022-09-28 2024-04-04 Bayer Aktiengesellschaft 3-hétéroaryl-5-chlorodifluorométhyl-1,2,4-oxadiazole utilisé comme fongicide
WO2024068517A1 (fr) 2022-09-28 2024-04-04 Bayer Aktiengesellschaft 3-(hétéro)aryl-5-chlorodifluorométhyl-1,2,4-oxadiazole utilisé comme fongicide
WO2024068519A1 (fr) 2022-09-28 2024-04-04 Bayer Aktiengesellschaft 3-(hétéro)aryl-5-chlorodifluorométhyl-1,2,4-oxadiazole utilisé comme fongicide
WO2024154683A1 (fr) * 2023-01-18 2024-07-25 クミアイ化学工業株式会社 Composition de lutte contre les maladies des plantes et procédé de lutte contre une maladie d'une plante utile l'utilisant

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