WO2022234470A1 - Novel fused heterocyclic compounds for combating phytopathogenic fungi - Google Patents

Novel fused heterocyclic compounds for combating phytopathogenic fungi Download PDF

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WO2022234470A1
WO2022234470A1 PCT/IB2022/054107 IB2022054107W WO2022234470A1 WO 2022234470 A1 WO2022234470 A1 WO 2022234470A1 IB 2022054107 W IB2022054107 W IB 2022054107W WO 2022234470 A1 WO2022234470 A1 WO 2022234470A1
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Prior art keywords
trifluoromethyl
dihydrothieno
oxadiazol
pyridin
alkyl
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PCT/IB2022/054107
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French (fr)
Inventor
Paras Raybhan BHUJADE
Maruti N Naik
Sonali SWARNKAR
Nitin Shivanna KORE
Santosh Shridhar AUTKAR
Alexander G.M. KLAUSENER
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Pi Industries Ltd.
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Priority to BR112023022854A priority Critical patent/BR112023022854A2/en
Publication of WO2022234470A1 publication Critical patent/WO2022234470A1/en

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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
    • C07D413/02—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
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Definitions

  • the present invention relates to novel fused heterocyclic compounds of formula (I) which are useful in combating phytopathogenic fungi, to a process for preparing such novel fused heterocyclic compounds, to a combination and to a composition comprising such novel fused heterocyclic compounds.
  • the present invention also relates to a method for combating phytopathogenic fungi.
  • Oxadiazole compounds are known to be useful in the pharmaceutical field. For instance, WO2013066835 discloses oxadiazole compounds as pharmaceutically active agents.
  • Oxadiazole compounds are also known to be useful as crop protection agents to combat or prevent infestation of microorganisms.
  • EP0276432, WO2015185485, EP3165093, EP3167716, EP3165093, WO2017110861, WO2017110862, WO2017110864, WO2017211652, WO2017220485, WO2017072247, WO2017076742, WO2018065414, WO2018118781 and WO2018202491 disclose the oxadiazole compounds which are used as fungicides.
  • oxadiazole compounds reported in the above cited literature have disadvantages in certain aspects, such that they exhibit a narrow spectrum of efficacy or that they do not have satisfactory fungicidal activity, particularly at low application rates. Therefore, there remains a need for the development of new fungicidal compounds, so as to provide novel compounds which are effective against a broader spectrum of fungi, having lower toxicity, higher selectivity, being used at lower dosage rates to reduce or avoid unfavorable environmental or toxicological effects whilst still allowing effective and long lasting control of fungal pathogens. Therefore, it is an objective of the present invention to provide compounds having an improved/enhanced activity and/or a broader efficacy spectrum against phytopathogenic fungi.
  • the present invention relates to compounds of formula (I), wherein, R 1 , R 2 , Z 1 , Z 2 and m are as defined in the detailed description.
  • the present invention also relates to a process for preparing the compounds of formula (I).
  • the compounds of formula (I) have been found to be advantageous over the compounds reported in the literature in either of improved fungicidal activity, broader spectrum of biological efficacy, lower application rates, more favourable biological or environmental properties, or enhanced plant compatibility.
  • the present invention further relates to combinations comprising a compound of formula (I) of the present invention and at least one further pesticidally active substance for effectively controlling or preventing phytopathogenic fungi which are difficult to combat.
  • the present invention still further relates to agricultural compositions comprising a compound of formula (I) as such or a compound of formula (I) in combination with a further pesticidally active substance.
  • the present invention still further relates to a method and use of a compound of formula (I) as such or the combination or a composition thereof for combating plant diseases, particularly phytopathogenic fungi.
  • transitional phrase “consisting of” excludes any element, step or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith.
  • the phrase “consisting of” appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.
  • the transitional phrase “consisting essentially of” is used to define a composition or method that includes materials, steps, features, components or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components or elements do not materially affect the basic and novel characteristic(s) of the claimed invention.
  • undesired microorganisms or “phytopathogenic microorganisms” such as fungal or bacterial pathogens includes namely Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes and Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • agronomic refers to the production of field crops such as for food, feed and fiber and includes the growth of corn, soybeans and other legumes, rice, cereal (e.g., wheat, oats, barley, rye, rice, maize), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifer and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone and citrus), small fruit (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives).
  • wheat e.g., wheat, oats, barley, rye, rice, maize
  • leafy vegetables e.g., lettuce, cabbage, and other cole crops
  • fruiting vegetables e.g., tomatoes, pepper, eggplant, crucifer and cucurbits
  • potatoes e.g., sweet potatoes, grapes, cotton, tree fruits (e.g.
  • nonagronomic refers to other than field crops, such as horticultural crops (e.g., greenhouse, nursery or ornamental plants not grown in a field), residential, agricultural, commercial and industrial structures, turf (e.g., sod farm, pasture, golf course, lawn, sports field, etc.), wood products, stored product, agro-forestry and vegetation management, public health (i.e. human) and animal health (e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as wildlife) applications.
  • horticultural crops e.g., greenhouse, nursery or ornamental plants not grown in a field
  • turf e.g., sod farm, pasture, golf course, lawn, sports field, etc.
  • wood products e.g., stored product, agro-forestry and vegetation management
  • public health i.e. human
  • animal health e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as wildlife
  • Nonagronomic applications include protecting an animal from a fungal or microbial infection by administering a biologically effective amount of a compound of the present invention, typically in the form of a composition formulated for veterinary use, to the animal to be protected.
  • fungicidal and microbiocidal refers to observable effects on micro-organisms to provide protection of an animal from the diseases.
  • Microbiocidal effects typically relate to diminishing the occurrence or activity of the target micro-organisms. Such effects include necrosis, death and retarded growth, lessened ability to remain on or in the host animal, reduced feeding and inhibition of reproduction.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” or - N(alkyl) or alkylcarbonylalkyl or alkylsuphonylamino includes straight-chain or branched C1 to C 2 4 alkyl, preferably C1 to C15 alkyl, more preferably C1 to C 10 alkyl, most preferably C1 to C 6 alkyl.
  • Non- limiting examples of alkyl include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2- methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2- dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylprop
  • the alkyl is at the end of a composite substituent, as, for example, in alkylcycloalkyl
  • the part of the composite substituent at the start for example the cycloalkyl
  • other radicals for example alkenyl, alkynyl, hydroxy, halogen, carbonyl, carbonyloxy and the like, are at the end.
  • alkenyl used either alone or in compound words includes straight-chain or branched C 2 to C 2 4 alkenes, preferably C 2 to C15 alkenes, more preferably C 2 to C 10 alkenes, most preferably C 2 to C 6 alkenes.
  • Non-limiting examples of alkenes include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-l-propenyl, l-methyl-2 -propenyl, 2- methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1- butenyl, 3-methyl-1-butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3- butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2 -propenyl, 1-ethyl-1-propenyl
  • Alkenyl also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl as a part of a composite substituent, for example haloalkenyl and the like, unless defined specifically elsewhere.
  • Non-limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3- butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l- methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl -2- propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, l-methyl-3- pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl,
  • alkynyl as a part of a composite substituent, for example haloalkynyl etc., unless specifically defined elsewhere.
  • alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
  • cycloalkyl means alkyl closed to form a ring. Non-limiting examples include cyclopropyl, cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as a part of a composite substituent, for example cycloalkylalkyl etc., unless specifically defined elsewhere.
  • cycloalkenyl means alkenyl closed to form a ring including monocyclic, partially unsaturated hydrocarbyl groups. Non-limiting examples include cyclopropenyl, cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as a part of a composite substituent, for example cycloalkenylalkyl etc., unless specifically defined elsewhere.
  • cycloalkynyl means alkynyl closed to form a ring including monocyclic, partially unsaturated groups. Non-limiting examples include cyclopropynyl, cyclopentynyl and cyclohexynyl.
  • cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere.
  • cycloalkoxy “cycloalkenyloxy” and the like are defined analogously. Non limiting examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as a part of a composite substituent, for example cycloalkoxy alkyl etc., unless specifically defined elsewhere.
  • halogen either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine.
  • haloalkyl when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different.
  • haloalkyl include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro
  • haloalkyl as a part of a composite substituent, for example haloalkylaminoalkyl etc., unless specifically defined elsewhere.
  • haloalkenyl “haloalkynyl” are defined analogously except that, instead of alkyl groups, alkenyl and alkynyl groups are present as a part of the substituent.
  • haloalkoxy means straight-chain or branched alkoxy groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above.
  • Non-limiting examples of haloalkoxy include 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 l,l,l-trifluoroprop-2-oxy.
  • haloalkylthio means straight-chain or branched alkylthio groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above.
  • Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1- bromoethylthio, 1- fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2- chloro-2- fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2- trichloroethylthio, pentafluoroethylthio and l,l,l
  • haloalkylthio as a part of a composite substituent, for example haloalkylthioalkyl etc., unless specifically defined elsewhere.
  • haloalkylsulfinyl include CF 3 S(O), CCl 3 S(O), CF 3 CH 2 S(O) and CF 3 CF 2 S(O).
  • haloalkylsulfonyl include CF 3 S(O) 2 , CCl 3 S(O) 2 , CF 3 CH 2 S(O) 2 and CF 3 CF 2 S(O) 2 .
  • hydroxy means —OH
  • Amino means —NRR, wherein R can be H or any possible substituent such as alkyl.
  • sulfinyl means SO
  • sulfonyl means S(O) 2 .
  • alkoxy used either alone or in compound words includes C 1 to C 24 alkoxy, preferably C 1 to C 15 alkoxy, more preferably C 1 to C 10 alkoxy, most preferably C 1 to C 6 alkoxy.
  • alkoxy examples include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1- dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1- ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2- methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3- dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2- ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and l-ethyl-2- methylpropoxy and the different isomers.
  • alkoxyalkyl denotes an alkoxy substitution on alkyl.
  • alkoxyalkyl include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
  • alkoxyalkoxy denotes an alkoxy substitution on alkoxy.
  • alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1- dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2- dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1- methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio,
  • Halocycloalkyl, halocycloalkenyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylcarbonyl, cycloalkylcarbonyl, haloalkoxylalkyl, and the like, are defined analogously to the above examples.
  • alkylthioalkyl denotes an alkylthio substitution on alkyl.
  • alkylthioalkyl include -CH 2 SCH 2 , -CH 2 SCH 2 CH 2 , CH 3 CH 2 SCH 2 , CH 3 CH 2 CH 2 CH 2 SCH 2 and CH 3 CH 2 SCH 2 CH 2 .
  • Alkylthioalkoxy denotes an alkylthio substitution on alkoxy.
  • cycloalkylalkylamino denotes a cycloalkyl substitution on alkyl amino.
  • alkoxyalkoxyalkyl is an alkoxy group bonded to a skeleton via a carbonyl group (-CO-). This definition also applies to alkoxycarbonyl as a part of a composite substituent, for example cycloalkylalkoxycarbonyl and the like, unless specifically defined elsewhere.
  • alkoxycarbonylalkylamino denotes an alkoxy carbonyl substitution on alkyl amino.
  • Alkylcarbonylalkylamino denotes an alkyl carbonyl substitution on alkyl amino.
  • alkylthioalkoxycarbonyl, cycloalkylalkylaminoalkyl and the like are defined analogously.
  • alkylsulfinyl include methylsulphinyl, ethylsulphinyl, propylsulphinyl, 1- methylethylsulphinyl, butylsulphinyl, 1-methylpropylsulphinyl, 2-methylpropylsulphinyl, 1,1- dimethylethylsulphinyl, pentylsulphinyl, 1-methylbutylsulphinyl, 2-methylbutylsulphinyl, 3- methylbutylsulphinyl, 2,2-dimethylpropylsulphinyl, 1-ethylpropylsulphinyl, hexylsulphinyl, 1,1- dimethylpropylsulphinyl, 1,2-dimethylpropylsulphinyl, 1-methylpentylsulphinyl, 2- methylpentylsulphinyl, 3-methylpentylsulphinyl, 4-methylp
  • arylsulfinyl includes Ar-S(O), wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphinyl as a part of a composite substituent, for example haloalkylsulphinyl etc., unless specifically defined elsewhere.
  • alkylsulfonyl include methylsulphonyl, ethylsulphonyl, propylsulphonyl, 1-methylethylsulphonyl, butylsulphonyl, 1-methylpropylsulphonyl, 2-methylpropylsulphonyl, 1,1- dimethylethylsulphonyl, pentylsulphonyl, 1-methylbutylsulphonyl, 2-methylbutylsulphonyl, 3- methylbutylsulphonyl, 2,2-dimethylpropylsulphonyl, 1-ethylpropylsulphonyl, hexylsulphonyl, 1,1- dimethylpropylsulphonyl, 1,2-dimethylpropylsulphonyl, 1-methylpentylsulphonyl, 2- methylpentylsulphonyl, 3-methylpentylsulphonyl, 4-methylpentylsulphony
  • arylsulfonyl includes Ar-S(O) 2 , wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphonyl as a part of a composite substituent, for example alkylsulphonylalkyl etc., unless defined elsewhere. “Alkylamino”, “dialkylamino”, and the like, are defined analogously to the above examples.
  • carrier or carbocyclic includes an “aromatic carbocyclic ring system” and a “non- aromatic carbocylic ring system” or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which the ring may be aromatic or non-aromatic (where aromatic indicates that the Huckel rule is satisfied and non-aromatic indicates that the Huckel rule is not statisfied).
  • non-aromatic heterocycle or “non-aromatic heterocyclic” means a three- to fifteen- membered, preferably three- to twelve- membered, saturated or partially unsaturated heterocycle containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur: mono, bi- or tricyclic heterocycles which contain, in addition to carbon ring members, one to three nitrogen atoms and/or one oxygen or sulphur atom or one or two oxygen and/or sulphur atoms; if the ring contains more than one oxygen atom, they are not directly adjacent; non-limiting examples thietanyl, oxetanyl, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolid
  • heterocyclyl as a part of a composite substituent, for example heterocyclylalkyl etc., unless specifically defined elsewhere.
  • heteroaryl or “aromatic heterocyclic” means 5 or 6-membered, fully unsaturated monocyclic ring systems containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur; if the ring contains more than one oxygen atom, they are not directly adjacent; 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom; 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom as ring members, non-limiting examples furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazoly
  • 6-membered heteroaryl which contains one to four nitrogen atoms: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain, respectively, one to three and one to four nitrogen atoms as ring members, non-limiting examples 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4- pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin- 3-yl and 1,2,4,5-tetrazin-3-yl; benzofused 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulphur atom: non-limiting examples indol-l-yl, indol- 2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indo
  • trialkylsilyl includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom such as trimethylsilyl, triethylsilyl and t-butyl-dimethylsilyl.
  • “Halotrialkylsilyl” denotes at least one of the three alkyl radicals is partially or fully substituted with halogen atoms which may be the same or different.
  • alkoxytrialkylsilyl denotes at least one of the three alkyl radicals is substituted with one or more alkoxy radicals which may be the same or different.
  • trialkylsilyloxy denotes a trialkylsilyl moiety attached through oxygen.
  • the total number of carbon atoms in a substituent group is indicated by the “C i -C j ” prefix where i and j are numbers from 1 to 21.
  • C 1 -C 3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl
  • C 2 alkoxyalkyl designates CH 3 OCH 2
  • C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 ), CH 3 OCH 2 CH 2 or CH 3 CH 2 OCH 2
  • C 4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
  • inventive compounds of the present invention may, if appropriate, be present as mixtures of different possible isomeric forms, especially of stereoisomers, for example E and Z, threo and erythro, and also optical isomers, but if appropriate also of tautomers.
  • stereoisomers for example E and Z, threo and erythro, and also optical isomers, but if appropriate also of tautomers.
  • E and the Z isomers, and also the threo and erythro isomers, and the optical isomers, any desired mixtures of these isomers and the possible tautomeric forms are disclosed and claimed.
  • microorganisms for the purpose of the present disclosure includes but is not limited to fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, insects and rodents.
  • plant is understood here to 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 transgenic plants and including the plant cultivars which are protectable and non-protectable by plant breeders’ rights.
  • plant includes a living organism of the kind exemplified by trees, shrubs, herbs, grasses, ferns, and mosses, typically growing in a site, absorbing water and required substances through its roots, and synthesizing nutrients in its leaves by photosynthesis.
  • plants for the purpose of the present invention include but are not limited to agricultural crops such as wheat, rye, barley, triticale, oats or rice; beet, e.g. sugar beet or fodder beet; fruits and fruit trees, such as pomes, stone fruits or soft fruits, e.g.
  • leguminous plants such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit and citrus trees, such as oranges, lemons, grapefruits or mandarins; any horticultural plants, vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; cucurbitaceae; oleaginous plants; energy and raw material plants, such as cereals, corn, soybean, other leguminous plants, rape, sugar cane or oil palm; tobacco; nuts; coffee; tea;
  • the plant for the purpose of the present invention includes but is not limited to cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and vegetables, ornamentals, any floricultural plants and other plants for the use of humans and animals.
  • plant parts is understood to mean all parts and organs of plants above and below the ground.
  • plant part includes but is not limited to cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots including taproots, lateral roots, root hairs, root apex, root cap, rhizomes, slips, shoots, fruits, fruit bodies, bark, stem, buds, auxillary buds, meristems, nodes and internodes.
  • locus thereof includes soil, surroundings of plant or plant parts and equipment or tools used before, during or after sowing/planting a plant or a plant part.
  • Application of the compounds of the present disclosure or the compounds of the present disclosure in a composition, optionally comprising other compatible compounds, to a plant or a plant material or locus thereof includes application by a technique known to a person skilled in the art which includes but is not limited to spraying, coating, dipping, fumigating, impregnating, injecting and dusting.
  • the term “applied” means adhered to a plant or plant part either physically or chemically including impregnation.
  • the present invention provides a compound of formula (I), wherein, Z 1 and Z 2 represent CHR 2 or N-R 3 ; provided that (i) both Z 1 and Z 2 are not CHR 2 simultaneously; (ii) both Z 1 and Z 2 are not N-R 3 simultaneously; R 1 is C 1 -C 6 haloalkyl; R 2 is selected from the group consisting of hydrogen, halogen, cyano, nitro, thiol, amino, hydroxy, C 1 - C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkylalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 - C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 2 -C 6 -haloalkenyl, C 3 -C 8 -halocycl
  • the present invention provides the compound of formula (I) wherein R 1 is selected from the group consisting of CF 3 , CF 2 H and CF 2 Cl.
  • the compound of formula (I) is represented by a compound of formula (Ia), Formula (Ia) wherein, R 1 , R 2 , R 3 , Z 1 and Z 2 are as defined in the above detailed description and and m is an integer selected from 0 to 3.
  • the compound of formula (I) is represented by a compound of formula (Ib), Formula (Ib) wherein, R 1 , R 2 , R 3 , Z 1 and Z 2 are as defined in the above detailed description and m is an integer selected from 0 to 3.
  • the compound of formula (I) is represented by a compound of formula (Ic), Formula (Ic) wherein, R 1 , R 2 , and R 3 are as defined in the above detailed description and m is an integer selected from 0 to 3.
  • the compound of formula (I) is represented by a compound of formula (Id), Formula (Id) wherein, R 1 , R 2 , and R 3 are as defined in the above detailed description and m is an integer selected from 0 to 3.
  • the compound of formula (I) is represented by a compound of formula (Ie), Formula (Ie) wherein, R 1 , R 2 , and R 3 are as defined in the above detailed description and m is an integer selected from 0 to 3.
  • the compound of formula (I) is represented by a compound of formula (If), Formula (If) wherein, R 1 , R 2 , and R 3 are as defined in the above detailed description and m is an integer selected from 0 to 3.
  • the present invention provides a compound of formula (I), wherein Z1 represents N-R 3 and Z2 represents CHR 2 ; and the radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and n have the same meanings as given for the compounds of formula (I) in the above detailed description.
  • the present invention provides a compound of formula (I), wherein Z1 represents CHR 2 and Z2 represents N-R 3 ; and the radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and n have the same meanings as given for the compounds of formula (I) in the above detailed description.
  • the present invention provides a compound of formula (I), Formula (I) wherein, Z 1 and Z 2 represent CHR 2 or N-R 3 ; provided that (i) both Z 1 and Z 2 are not CHR 2 simultaneously; (ii) both Z 1 and Z 2 are not N-R 3 simultaneously;
  • R 1 is selected from the group consisting of CF 3 , CHF 2 and CF 2 Cl;
  • R 2 is selected from the group consisting of hydrogen, halogen, cyano, nitro, thiol, amino, hydroxy, C 1 - C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 - alkoxy-C 1 -C 6 -alkyl;
  • R 3 is selected from the group consisting of C 1 -C 6 -
  • the present invention provides a compound of formula (I), Formula (I) wherein, Z 1 represents N-R 3 and Z 2 represents CHR 2 ; R 1 is selected from the group consisting of CF 3 , CHF 2 and CF 2 Cl; R 2 is selected from the group consisting of hydrogen, halogen, cyano, nitro, thiol, amino, hydroxy, C 1 - C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 - alkoxy-C 1 -C 6 -alkyl; R 3 is selected from the group consisting of C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alky
  • the present invention provides a compound of formula (I), Formula (I) wherein, Z 1 represents CHR 2 and Z 2 represents N-R 3 ; R 1 is selected from the group consisting of CF 3 , CHF 2 and CF 2 Cl; R 2 is selected from the group consisting of hydrogen, halogen, cyano, nitro, thiol, amino, hydroxy, C 1 - C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 - alkoxy-C 1 -C 6 -alkyl; R 3 is selected from the group consisting of C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alky
  • n is an integer selected from 0 to 2. In yet another preferred embodiment, n is an integer selected from 0 to 1.
  • the present invention provides a compound of formula (I), wherein R 1 is selected from the group consisting of CF 3 , CHF 2 and CF 2 Cl; and the radicals R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Z 1 , Z 2 and n have the same meanings as given for the compounds of formula (I) in the above detailed description.
  • R 2 is selected from the group consisting of hydrogen, halogen, cyano, nitro, thiol, amino, hydroxyl and C 1 -C 6 -alkyl; and the radicals R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Z 1 , Z 2 , m and n have the same meanings as given for the compounds of formula (I) in the above detailed description.
  • the present invention provides a compound of formula (I), wherein R 4 is selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 alkoxy-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkylamino, C 6 - C 10 -aryl, C 6 -C 10 -aryl-C 1 -C 6 -alkyl, C 3 -C 8 -heterocyclyl and C 3 -C 8 -heterocyclyl-C 1 -C 6 -alkyl; each group of R 4 may optionally be substituted with one or more groups R 4a selected from the group consisting of halogen, cyano, amino, C 1 -C 6 -alky
  • the present invention provides a compound of formula (I), wherein R 5 is selected from the group consisting of hydrogen or C 1 -C 6 -alkyl; and the radicals R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8 , R 9 , Z 1 , Z 2 and n have the same meanings as given for the compounds of formula (I) in the above detailed description.
  • the present invention provides a compound of formula (I), wherein R 6 is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - cycloalkyl-C 1 -C 6 -alkyl, C 6 -C 10 -aryl, C 6 -C 10 -aryl-C 1 -C 6 -alkyl, C 3 -C 8 -heterocyclyl and C 3 -C 8 - heterocyclyl-C 1 -C 6 -alkyl; each group of R 6 may optionally be substituted with one or more groups R 6a ; and the radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , Z 1 , Z 2 , m and n have the same meanings as given for the compounds of formula (I) in the above detailed description.
  • the present invention provides a compound of formula (I), wherein R 6a may be optionally substituted with halogen, cyano, amino, C 1 -C 6 -alkylamino, C 1 -C 6 dialkylamino, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -haloalkyl , C 1 -C 6 -alkylthio and C 3 - C 6 -cycloalkyl; and the radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Z 1 , Z 2 , m and n have the same meanings as given for the compounds of formula (I) in the above detailed description.
  • the present invention provides a compound of formula (I), wherein R 8 is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C 1 - C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -alkylthio; and the radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 9 , Z 1 , Z 2 , m and n have the same meanings as given for the compounds of formula (I) in the above detailed description.
  • the present invention provides a compound of formula (I), wherein R 9 is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkyl; and the radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , Z 1 , Z 2 , m and n have the same meanings as given for the compounds of formula (I) in the above detailed description.
  • the compound of formula (I) is selected from (4-methoxyphenyl)(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, (3- methoxyphenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)methanone, p-tolyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)methanone, pyridin-3-yl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothien
  • the compounds of the present disclosure may be present either in pure form or as mixtures of different possible isomeric forms such as stereoisomers or constitutional isomers.
  • the various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, and geometric isomers. Any desired mixtures of these isomers fall within the scope of the claims of the present disclosure.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other isomer(s) or when separated from the other isomer(s).
  • An anion part of the salt in case the compound of formula (I) is cationic or capable of forming a cation can be inorganic or organic.
  • a cation part of the salt in case the compound of formula (I) is anionic or capable of forming an anion can be inorganic or organic.
  • the inorganic anion part of the salt include but are not limited to chloride, bromide, iodide, fluoride, sulfate, phosphate, nitrate, nitrite, hydrogen carbonates or hydrogen sulfate.
  • Examples of the organic anion part of the salt include but are not limited to formate, alkanoates, carbonates, acetates, trifluoroacetate, trichloroacetate, propionate, glycolate, thiocyanate, lactate, succinate, malate, citrates, benzoates, cinnamates, oxalates, alkylsulphates, alkylsulphonates, arylsulphonates aryldisulphonates, alkylphosphonates, arylphosphonates, aryldiphosphonates, p-toluenesulphonate, and salicylate.
  • Examples of the inorganic cation part of the salt include but are not limited to alkali and alkaline earth metals.
  • Examples of the organic cation part of the salt include but are not limited to pyridine, methyl amine, imidazole, benzimidazole, hitidine, phosphazene, tetramethyl ammonium, tetrabutylammonium, choline and trimethylamine.
  • Metal ions in the metal complexes of the compound of formula (I) are especially the ions of the elements of the second main group, especially calcium and magnesium, of the third and fourth main groups, especially aluminium, tin and lead, and also of the first to eighth transition groups, especially chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Particular preference is given to the metal ions of the elements of the fourth period and the first to eighth transition groups.
  • the metals can be present in the various valencies that they can assume.
  • the compound selected from formula (I), may typically exist in more than one form.
  • Formula (I) thus includes all crystalline and non- crystalline forms of the compounds that formula (I) represents.
  • Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts.
  • Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types).
  • polymorph refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due to the presence or absence of co- crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability.
  • a polymorph of a compound represented by formula (I) can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound represented by formula (I).
  • Preparation and isolation of a particular polymorph of a compound represented by formula (I) can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures.
  • the present invention provides a process for the preparing the compounds of formula (I).
  • the following schemes illustrate approaches for preparing the compounds of formula (I). The following descriptions and examples are provided for illustrative purposes and should not be construed as limiting in terms of substituents or substitution patterns.
  • the compounds of formula iii can be prepared by the cyanation of bromo compounds of formula ii.
  • This reaction can be performed by using a cyanating agent as for instance potassium hexacyanoferrate(II)trihydrate in the presence of a as for instance catalyst XantPhos Pd(allyl)]Cl and a base as for instance potassium acetate.
  • This reaction is typically carried out in the presence of a solvent, 1,4-dioxane, at a temperature ranging from 80 to 100 °C.
  • this reaction can also be carried out by reacting compounds of formula ii with potassium ferrocyanide in the presence of a catalyst for instance dichloro[bis ⁇ 1- (dicyclohexylphosphanyl)piperidine ⁇ ]palladium in a solvent as for instance 1-methyl-pyrrolidin-2- one at a temperature of 140 °C as reported in the Chemistry - A European Journal, 2012, vol. 18, # 10, p.2978 – 2986.
  • Step: 2 The compounds of formula iv can be obtained by reacting compounds of formula iii with hydroxyl amine in the presence of a suitable polar protic solvent such as ethanol, methanol and the like.
  • this reaction can also be carried out by using hydroxylamine hydrochloride in the presence of a suitable organic or a suitable inorganic base such as triethylamine, N,N- diisopropylethylamine, sodium bicarbonate and the like.
  • a suitable organic or a suitable inorganic base such as triethylamine, N,N- diisopropylethylamine, sodium bicarbonate and the like.
  • a suitable base such as triethylamine or N,N-diisopropylethylamine and the like.
  • a suitable amide coupling reagent such as HATU ((1-[bis(dimethylamino)methylene]- 1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate), N-(3-
  • This reaction can be carried out in the presence of a suitable base such as triethylamine, N,N- diisopropylethylamine and the like; in a suitable aprotic solvent such as tetrahydrofurane, dichloromethane and the like. This reaction is typically carried out at a temperature ranging from 0 to 40 °C.
  • a suitable base such as triethylamine, N,N- diisopropylethylamine and the like
  • a suitable aprotic solvent such as tetrahydrofurane, dichloromethane and the like.
  • the present invention relates to an agrochemical composition
  • agrochemical composition comprising a compound of formula (I) or agriculturally acceptable salts, metal complexes, constitutional isomers, stereo-isomers, diastereoisomers, enantiomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, geometric isomers, or N-oxides thereof optionally with one or more additional active ingredients(s), and optionally together with an auxiliary such as an inert carrier or any other essential ingredient(s) such as surfactants, additives, solid diluents and liquid diluents. It is also possible to use the compounds of formula (I) as fungicides.
  • fungicide means a compound that controls, modifies, or prevents the growth of phytopathogenic fungi.
  • the present invention provides a method for controlling or preventing phytopathogenic microorganisms, wherein the method comprises treating the fungi or the materials, plants, plant parts, locus thereof, soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of formula (I) or the combination or the composition.
  • the present invention provides a method for controlling or preventing infestations of plants by phytopathogenic microorganisms in agricultural crops and/or horticultural crops, wherein an effective amount of at least one compound of formula (I) or the combination or the composition thereof is applied to the plants, to parts thereof or to a locus thereof.
  • the present invention provides a method for controlling or preventing infestation of plants by phytopathogenic microorganisms in agricultural crops and/or horticultural crops wherein an effective amount of at least one compound of formula (I) or the combination or the composition thereof, is applied to the seeds of plants.
  • the compounds of formula (I) and the compositions according to the invention, respectively, are suitable as fungicides.
  • Plasmodiophoromycetes Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti).
  • Some are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides.
  • they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.
  • the compounds of formula (I) and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g.
  • the compounds of formula (I) and the compositions according to the invention are important in the control of phytopathogenic fungi on cereals (e. g. wheat, rye, barley, triticale, oats or rice), soybeans and on plant propagation material, such as seeds, and the crop material of soybeans.
  • the present invention provides compositions comprising at least one compound of formula (I) and seed.
  • the amount of the compound of formula (I) in the composition ranges from 0.1 g a.i. (gram per active ingredient) to 10 kg a.i. (kilogram per active ingredient) per 100 kg of seeds.
  • the present invention provides a seed comprising a compound of formula (I), wherein the amount of the compound of formula (I) is from 0.1 g to 1 kg per 100 kg of seed.
  • the compounds of formula (I) and compositions thereof, respectively are used for controlling a multitude of fungi on field crops, such as potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • plant propagation material is to be understood to denote all the generative or reproductive parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant.
  • vegetative plant material such as cuttings and tubers (e. g. potatoes)
  • These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring, using the compounds of formula (I) and compositions thereof.
  • the treatment of plant propagation materials with the compounds of formula (I), the combination and or the composition thereof, respectively, is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; on rice, corn, cotton and soybeans.
  • the term "cultivated plants” is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf. http://cera-gmc.org/, see GM crop database therein).
  • Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination.
  • one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo-or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.
  • auxin herbicides like dicamba or 2,4-D
  • bleacher herbicides such as hydroxylphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors
  • acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones
  • glutamine synthetase (GS) inhibitors such as glufosinate
  • protoporphyrinogen-IX oxidase inhibitors lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i.
  • herbicides e. bromoxynil or ioxynil herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as the resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors.
  • These herbicide resistance technologies are e. g. described in Pest Managem. Sci. 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci.
  • mutagenesis e.g. Clearfield ® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g. imazamox, or ExpressSun ® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g. tribenuron.
  • the Bacillus are particularly from Bacillus thuringiensis, such as ⁇ - endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp.
  • ⁇ - endotoxins e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl) or Cry9c
  • VIP vegetative insecticidal proteins
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors
  • ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA- reductase
  • ion channel blockers such as blockers of sodium or calcium
  • these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO02/015701).
  • Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP374753, WO93/007278, WO95/34656, EP427529, EP451878, WO03/18810 und WO03/52073.
  • the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.
  • insecticidal proteins contained in the genetically modified plants, impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).
  • Genetically modified plants capable to synthesize one or more insecticidal proteins are, e.
  • WO 03/018810 MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).
  • plants capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens by the use of recombinant DNA techniques are also within the scope of the present invention. Examples of such proteins are the so-called "pathogenesis-related proteins" (PR proteins, see, e. g.
  • plant disease resistance genes e. g. potato cultivars, which express resistance genes acting against phytophthora infestans derived from the mexican wild potato solanum bulbocastanum
  • T4-lysozym e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora
  • the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.
  • plants capable to synthesize one or more proteins, by the use of recombinant DNA techniques, to increase the productivity e. g.
  • plants that contain a modified amount of substances of content or new substances of content, by the use of recombinant DNA techniques, to improve human or animal nutrition e. g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera ® rape, DOW Agro Sciences, Canada) are also within the scope of the present invention.
  • plants that contain a modified amount of substances of content or new substances of content by the use of recombinant DNA techniques, to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora ® potato, BASF SE, Germany) are also within the scope of the present invention.
  • the present invention also relates to a method for combating infestation of plants by phytopathogenic micro-organisms in agricultural crops and or horticultural crops wherein an effective amount of at least one compound of formula (I) or the combination of the present invention or the composition of the present invention, is applied to the seeds of plants.
  • the compounds, the combinations and the compositions of the present invention can be used for combating plant diseases.
  • the compounds of formula (I), the combinations and or the compositions thereof, respectively, are particularly suitable for controlling the following plant diseases: Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. Candida) and sunflowers (e. g. A. tragopogonis); Altemaria spp. (Alternaria leaf spot) on vegetables, rape (A. brassicola or brassicae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. solani or A. alternata), tomatoes (e. g. A. solani or A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp.
  • Botrytis cinerea (teleomorph: Botryotinia fuckeliana: grey mold) on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spots) on corn (e. g.
  • Gray leaf spot C. zeae-maydis
  • rice sugar beets (e. g. C. beticola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchii) and rice
  • Cladosporium spp. on tomatoes e. g. C. fulvum: leaf mold
  • cereals e. g. C. herbarum (black ear) on wheat
  • Cochliobolus anamorph: Helminthosporium of Bipolaris
  • spp. (leaf spots) on corn (C. carbonum), cereals (e. g. C.
  • sativus anamorph: B. sorokiniana
  • rice e. g. C. miyabeanus, anamorph: H. oryzae
  • Colletotrichum teleomorph: Glomerella
  • spp. anthracnose on cotton (e. g. C. gossypii), corn (e. g. C. graminicola: Anthracnose stalk rot), soft fruits, potatoes (e. g. C. coccodes: black dot), beans (e. g. C. lindemuthianum) and soybeans (e. g. C. truncatum or C. gloeosporioides); Corticium spp., e. g. C. C.
  • sasakii sheath blight
  • Corynespora cassiicola leaf spots
  • Cycloconium spp. e. g. C. oleaginum on olive trees
  • Cylindrocarpon spp. e. g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.
  • liriodendri Neonectria liriodendri: Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D. phaseolorum (damping off) on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. D.
  • tritici-repentis tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (£. pyri), soft fruits (£. veneta: anthracnose) and vines (£.
  • ampelina anthracnose
  • Entyloma oryzae leaf smut
  • Epicoccum spp. black mold
  • Erysiphe spp. potowdery mildew
  • sugar beets £. betae
  • vegetables e. g. E. pisi
  • cucurbits e. g. E. cichoracearum
  • cabbages e. g. E. cruciferarum
  • Eutypa lata Eutypa canker or dieback, anamorph: Cytosporina lata, syn.
  • G. sabinae rust on pears
  • Helminthosporium spp. syn. Drechslera, teleomorph: Cochliobolus
  • Hemileia spp. e. g. H. vastatrix (coffee leaf rust) on coffee
  • Isariopsis clavispora syn. Cladosporium vitis
  • Macrophomina phaseolina syn. phaseoli
  • root and stem rot on soybeans and cotton
  • Microdochium syn. Fusarium
  • nivale pink snow mold
  • Microsphaera diffusa (powdery mildew) on soybeans
  • Monilinia spp. e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants
  • Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas
  • Peronospora spp. downy mildew) on cabbage (e. g. P.
  • brassicae brassicae
  • rape e. g. P. parasitica
  • onions e. g. P. destructor
  • tobacco P. tabacina
  • soybeans e. g. P. manshurica
  • Phakopsora pachyrhizi and P. meibomiae staybean rust
  • Phialophora spp. e. g. on vines (e. g. P. tracheiphila and P. tetraspora) and soybeans (e. g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P.
  • betae root rot, leaf spot and damping-off
  • Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e. g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e. g. P. capsici), soybeans (e. g. P. megasperma, syn. P. sojae), soybeans, potatoes and tomatoes (e. g. P.
  • Plasmodiophora brassicae club root
  • Plasmopara spp. e. g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers
  • Plasmopara spp. e. g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers
  • Podosphaera spp. powdery mildew) on rosaceous plants, hop, pome and soft fruits, e. g. P. leucotricha on apples
  • Polymyxa spp. e. g. on cereals, such as barley and wheat (P.
  • Pseudocercosporella herpotrichoides eyespot, teleomorph: Tapesia yallundae
  • Pseudoperonospora downy mildew
  • Pseudopezicula tracheiphila red fire disease or .rotbrenner', anamorph: Phialophora) on vines
  • Puccinia spp. rusts
  • oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum); Ramularia spp., e. g. R. collo-cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp.
  • R. solani root and stem rot
  • S. solani silk and stem rot
  • S. solani silk and stem rot
  • S. solani silk blight
  • R. cerealis Rhizoctonia spring blight
  • Rhizopus stolonifer black mold, soft rot
  • Rhynchosporium secalis scald
  • Sarocladium oryzae and S. attenuatum sheath rot) on rice
  • Sclerotinia spp e. g.
  • R. solani root and stem rot
  • S. solani silk blight
  • R. cerealis Rhizoctonia spring blight
  • Rhizopus stolonifer black mold, soft rot
  • Rhynchosporium secalis scald
  • Sarocladium oryzae and S. attenuatum sheath rot
  • Sclerotinia spp Sclerotinia spp.
  • seed rot or white mold on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soybeans (e. g. S. rolfsii or S. sclerotiorum); Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum (Stagonospora blotch) on cereals; Uncinula (syn.
  • Erysiphe) necator prowdery mildew, anamorph: Oidium tuckeri
  • Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e. g. S. reiliana: head smut), sorghum und sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp.
  • S. nodorum Stagonospora blotch, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum
  • wheat Synchytrium endobioticum on potatoes (potato wart disease)
  • Taphrina spp. e. g. T. deformans (leaf curl disease) on peaches and T. pruni (plum pocket) on plums
  • Thielaviopsis spp. black root rot
  • tobacco, pome fruits, vegetables, soybeans and cotton e. g. T. basicola (syn. Chalara elegans); Tilletia spp.
  • Non-limiting examples of pathogens of fungal diseases which can be treated in accordance with the invention include: Ustilaginales such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae, rusts for example those caused by Pucciniales such as Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, Puccinia graminis, Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f.sp.
  • Ustilaginales such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae
  • rusts for example those caused by Pucciniales such as
  • Puccinia striiformis f.sp. Secalis Pucciniastrum coryli, or Uredinales such as Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor and Uromyces viciae-fabae; and other rots and diseases such as those caused by Cryptococcus spp., Exobasidium vexans, Marasmiellus inoderma, Mycena spp., Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, ltersonilia perplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctonia solani
  • Blastocladiomycetes such as Physoderma maydis.
  • Mucoromycetes such as Choanephora cucurbitarum; Mucor spp.; and Rhizopus arrhizus
  • diseases caused by rust pathogens for example Gymnosporangium species, for example Gymnosporangium sabinae; Hemileia species, for example Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia species, for example Puccinia recondita, Puccinia graminis oder Puccinia striiformis; Uromyces species, for example Uromyces appendiculatus; In particular, Cronartium ribicola (White pine blister rust); Gymnosporangium juniperi-virginianae (Cedar-apple rust); Hemileia vasta
  • Puccinia persistens subsp.
  • Puccinia sorghi rust in corn
  • Puccinia striiformis 'Yellow rust' in cereals
  • Uromyces appendiculatus rust of beans
  • Uromyces phaseoli Bean rust
  • Puccinia melanocephala 'Brown rust' in sugarcane
  • Puccinia kuehnii 'Orange rust' in sugarcane
  • Plants which can be treated in accordance with the invention include the following: cotton, flax, grapevine, fruits, vegetables, such as Rosaceae sp (for example pome fruits such as apples, pears, apricots, cherries, almonds and peaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example banana trees and plantations), Rubiaceae sp.
  • Rosaceae sp for example pome fruits such as apples, pears, apricots, cherries, almonds and peaches
  • Ribesioidae sp. Juglandaceae sp.
  • Betulaceae sp. Ana
  • Theaceae sp. for example coffee
  • Theaceae sp. Sterculiceae sp.
  • Rutaceae sp. for example lemons, oranges and grapefruit
  • Vitaceae sp. for example grapes
  • Solanaceae sp. for example tomatoes, peppers
  • Liliaceae sp. for example lettuce
  • Umbelliferae sp. for example Cruciferae sp., Chenopodiaceae sp.
  • Cucurbitaceae sp. for example cucumber
  • Alliaceae sp. for example leek, onion
  • peas for example peas
  • major crop plants such as Poaceae/Gramineae sp.
  • Poaceae/Gramineae sp. for example maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale
  • 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
  • phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidennatum, 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 present invention also relates to the use of the compounds of formula (I), the combinations or the compositions thereof for combating the following plant diseases: Puccinia spp. (rusts) on various plants, for example, but not limited to P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye and Phakopsoraceae spp. on various plants, in particular Phakopsora pachyrhizi and P.
  • Puccinia spp. rusts
  • rusts rusts
  • rusts rusts
  • P. triticina brown or leaf rust
  • P. striiformis stripe or yellow rust
  • P. hordei dwarf
  • the present invention also relates to the use of the compounds of formula (I), the combinations or the compositions thereof for combating the following plant diseases: Hemileia vastatrix (Coffee rust), Uromyces appendiculatus/fabae/ phaseoli (rust of beans) Puccinia spp. (rusts) on various plants selected from P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P.
  • Hordei dwarf rust
  • P. graminis stem or black rust
  • P. recondita brown or leaf rust
  • the present invention further relates to the use of the compounds of formula (I), the combinations or the compositions thereof for combating against phytopathogenic fungi such as Phakopsora pachyrhizi, Phakopsora meibomiae, of agricultural crops and or horticultural crops.
  • the compounds of formula (I), the combinations and the compositions thereof, respectively, are also suitable for the protection of harvest, stored products or materials against harmful fungi.
  • the term "protection of materials” is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria.
  • Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Pora spp., Serpula spp.
  • Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.
  • Basidiomycetes such as Coniophora spp
  • Candida spp. and Saccharomyces cerevisae are particularly suitable for controlling the following plant diseases: Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans.
  • the present invention further relates to a method for combating phytopathogenic fungi.
  • the method comprises treating the fungi or the materials, plants, plant parts, locus thereof, soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of formula (I) or the combination or the composition comprising at least one compound of formula (I).
  • the method of treatment according to the invention can also be used in the field of protecting stored products or harvest against the attack of fungi and microorganisms.
  • the term "stored products” is understood to denote natural substances of plant or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired.
  • Stored products of crop plant origin such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains
  • timber whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood.
  • Stored products of animal origin are hides, leather, furs, hairs and the like. The combination according the present invention can prevent disadvantageous effects such as decay, discoloration or mold.
  • stored products is understood to denote natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms.
  • the compounds of formula (I), the combinations and the compositions thereof, respectively, may be used for improving the health of a plant.
  • the invention also relates to a method for improving plant health by treating a plant, its propagation material and/or the locus where the plant is growing or is to grow with an effective amount of compound (I) and the composition thereof, respectively.
  • plant health is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other such as yield (e. g.
  • the above identified indicators for the health condition of a plant may be interdependent or may result from each other.
  • the compounds of formula (I) can be present in different crystal modifications or polymorphs whose biological activity may differ. They are likewise subject matter of the present invention.
  • the compounds of formula (I) are applied as such or in the form of compositions for treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active ingredients.
  • the application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi.
  • Plant propagation materials may be treated with a compound of formula (I), the combination and the composition thereof protectively either at or before planting or transplanting.
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of formula (I).
  • An agrochemical composition comprises a fungicidally effective amount of a compound of formula (I).
  • effective amount denotes an amount of the composition or of the compound of formula (I), 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 formula (I) used.
  • the compounds of formula (I), their -oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof can be converted into customary types of agrochemical compositions, e. g. into solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • composition types are suspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC), emulsions (e.
  • composition types are defined in the "Catalogue of pesticide Formulation types and international coding system", Technical Monograph No.2, 6 th Ed. May 2008, CropLife International.
  • compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New Developments in Crop Protection Product Formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers in this context are for instance water and organic solvents, such as mineral oil fractions of medium to high boiling point, e. g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e. g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, e. g. cyclohexanone; esters, e. g.
  • mineral oil fractions of medium to high boiling point e. g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e. g. toluene, paraffin, tetrahydrona
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e. g. N-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof.
  • Suitable solid carriers or fillers are for instance mineral earths, e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers, e. g.
  • Suitable surfactants are surface-active compounds, for instance such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof.
  • surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant.
  • Suitable anionic surfactants are for instance alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl-and tridecylbenzenes, sulfonates of naphthalenes and alkyl naphthalenes, sulfosuccinates or sulfosuccinamates.
  • Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are for instance alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-substituted fatty acid amides are for instance fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are homo- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.
  • Suitable cationic surfactants are for instance quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are for instance block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are for instance polyacids or polybases.
  • polyacids are alkali salts of polyacrylic acid or polyacid comb polymers.
  • polybases are polyvinyl amines or polyethylene amines.
  • Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves, and which improve the biological performance of the compounds of formula (I) on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and Additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are for instance polysaccharides (e. g.
  • xanthan gum carboxymethyl cellulose
  • inorganic clays organic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are for instance bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
  • Suitable anti-freezing agents are for instance ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are for instance silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants e. g. in red, blue, or green
  • examples are inorganic colorants (e.
  • Suitable tackifiers or binders are for instance polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • Examples for composition types and their preparation are: i) Water-soluble concentrates (SL, LS) 10-60 wt% of a compound of formula (I) and 5-15 wt% wetting agent (e. g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e. g.
  • Dispersible concentrates 5-25 wt% of a compound of formula (I) and 1-10 wt% dispersant (e. g. polyvinyl pyrrolidone) are dissolved in an organic solvent (e. g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion of the active substance.
  • Emulsifiable concentrates EC 15-70 wt% of a compound of formula (I) and 5-10 wt% emulsifier (e. g.
  • Emulsions (EW, EO, ES) 5-40 wt% of a compound of formula (I) and 1-10 wt% emulsifier (e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a 20-40 wt% water-insoluble organic solvent (e. g. aromatic hydrocarbon).
  • binder e. g. polyvinyl alcohol
  • binder e. g. polyvinyl alcohol
  • dispersants and wetting agents e. g. sodium lignosulfonate and alcohol ethoxylate
  • Water-dispersible powders and water-soluble powders (WP, SP, WS) 50-80 wt% of a compound of formula (I) are ground in a rotor-stator mill with the addition of 1-5 wt% dispersants (e. g. sodium lignosulfonate), 1-3 wt% wetting agents (e. g. alcohol ethoxylate) and a solid carrier (e. g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants e. g. sodium lignosulfonate
  • wetting agents e. g. alcohol ethoxylate
  • a solid carrier e. g. silica gel
  • Microcapsules An oil phase comprising 5-50 wt% of a compound of formula (I), 0-40 wt% of a water insoluble organic solvent (e. g. aromatic hydrocarbon) and 2-15 wt% of 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 results in the formation of poly(meth)acrylate microcapsules.
  • a protective colloid e. g. polyvinyl alcohol.
  • Radical polymerization results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 wt% of a compound of formula (I) according to the invention, 0-40 wt% of a water insoluble organic solvent (e. g. aromatic hydrocarbon), and an isocyanate monomer (e. g. diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol).
  • a polyamine e. g. hexamethylenediamine
  • the addition of a polyamine results in the formation of polyurea microcapsules comprising the active substance.
  • the monomers amount to 1-10 wt%.
  • the wt% relates to the total CS composition.
  • Dustable powders (DP, DS) 1-10 wt% of a compound of formula (I) are ground finely and mixed intimately with a solid carrier (e. g. finely divided kaolin) ad 100 wt%.
  • xii) Granules (GR, FG) 0.5-30 wt% of a compound of formula (I) are ground finely and associated with a solid carrier (e. g. silicate) ad 100 wt%.
  • Ultra-low volume liquids 1-50 wt% of a compound of formula (I) are dissolved in an organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%.
  • the compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active ingredient (ai).
  • the active ingredients (ai) are employed in a purity from 90% to 100%, preferably from 95% to 100% (according to the NMR spectrum).
  • solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are usually employed.
  • the compositions in question give, after two-to-tenfold dilution, active substance concentrations from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations.
  • Methods for applying the compounds of formula (I), the combination and the composition thereof, respectively are applications onto plant propagation material, especially seeds, including dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods.
  • the compounds of formula (I), the combination and the composition thereof, respectively are applied on to the plant propagation material by a method such that the germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 1.0 kg per ha, and in particular from 0.1 to 1.0 kg per ha.
  • the generally required amounts of the active substance are from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kg of plant propagation material (preferably seeds).
  • the amount of active substance applied depends on the kind of application area and on the desired effect.
  • Amounts customarily applied in the protection of materials are ranging from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg, of active substance per cubic meter of treated material.
  • Various types of oils, wetters, adjuvants, fertilizers, or micronutrients, and further pesticides e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides
  • pesticides e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides
  • These agents can be mixed with the composition according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:20 to 20:1.
  • a pesticide is generally a chemical or biological agent (such as pesticidally active ingredient, compound, composition, virus, bacterium, antimicrobial or disinfectant) that through its effect deters, incapacitates, kills or otherwise discourages pests.
  • Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease or are vectors for disease.
  • pesticide includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant defense activators that activate plant physiology for defense against certain pests; safeners that reduce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology e.g. to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.
  • the user applies compositions according to the invention usually from a predosage device, a Knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the respective agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is obtained by this procedure.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
  • one embodiment of the invention is a kit for preparing a usable pesticidal composition, the kit comprising a) a composition comprising component 1) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally a further active component 3) as defined herein.
  • the present invention provides a combination comprising a compound of formula (I) and at least one further pesticidally active substance selected from the group consisting of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertilizers and nutrients.
  • the compounds of formula (I), the combinations and the compositions thereof comprising them in the use as fungicides with other fungicides may result in an expansion of the fungicidal spectrum of activity being obtained or in a prevention of fungicide resistance development. Furthermore, in many cases, extraordinary and unexpected effects are obtained.
  • the present invention also relates to combinations comprising at least one compound of formula (I) as component (1) and at least one further pesticidally active substance as component (2), selected from the group of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertiliers and nutrients.
  • the pesticidally active substances reported in WO2015185485 pages 36-43 and WO2017093019 pages 42-56 can be used in conjunction with the compounds of formula (I).
  • the pesticidally active substances referred to as component (2), their preparation and their activity e. g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available.
  • the compounds described by the IUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci.
  • the present invention furthermore relates to agrochemical mixtures comprising at least one compound of formula (I) (component 1) and at least one further active substance useful for plant protection.
  • agrochemical mixtures comprising at least one compound of formula (I) (component 1) and at least one further active substance useful for plant protection.
  • an additional effect can be obtained.
  • This can be obtained by applying the compounds of formula (I) and at least one further pesticidally active substance simultaneously, either jointly (e. g. as tank-mix) or separately, or in succession, wherein the time interval between the individual applications is selected in such a way that it is ensured that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further pesticidally active substance(s).
  • the order of application is not essential for the working of the present invention.
  • the time between both applications may vary e. g. between 2 hours to 7 days. Also a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.
  • the weight ratio of the component 1) and the component 2) generally depends on the properties of the active components used, usually it is in the range of 1:1000 to 1000:1, often in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1, even more preferably in the range of 1:4 to 4:1 and in particular in the range of 1:2 to 2:1.
  • the weight ratio of the component 1) and the component 2) usually is in the range of 1000:1 to 1:1000, often in the range of 100:1 to 1:100, regularly in the range of 50:1 to 1:50, preferably in the range of 20:1 to 1:20, more preferably in the range of 10:1 to 1:10, even more preferably in the range of 4:1 to 1:4 and in particular in the range of 2:1 to 1:2.
  • the ternary mixtures i.e.
  • the weight ratio of component 1) and component 2) depends from the properties of the active substances used, usually it is in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1 and in particular in the range of 1:4 to 4:1 and 1:2 to 2:1, and the weight ratio of component 1) and component 3) usually it is in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1 and in particular in the range of 1:4 to 4:1 and 1:2 to 2:1.
  • any further active components are, if desired, added in a ratio of 20:1 to 1:20 to the component 1). These ratios are also suitable for the preparation of inventive mixtures applied by seed treatment.
  • the invention disclosed in the present disclosure shall now be elaborated with the help of non-limiting examples.
  • Example 1 Preparation of phenyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone (Compound no.14) a) Step 1: tert-butyl 6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate To a stirred solution of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (1 g, 5.7 mmol) in dichloromethane (12 mL) and methanol (3 mL), triethylamine (1.6 mL, 11.4 mmol) and di-tert-butyl dicarbonate (1.57 mL, 6.8 mmol) were added slowly at 0 °C.
  • the resulting reaction mixture was stirred at 25 °C for 12 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain a crude product.
  • the crude product was dissolved in dichloromethane (30 mL) and washed with water (90 mL). The dichloromethane layer was dried over anhydrous sodium sulfate and the volatiles were removed under reduced pressure to obtain tert-butyl 6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (1.35 g, 99 % yield).
  • Step 2 tert-butyl 2-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate
  • a stirred solution of tert-butyl 6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (7.5 g, 31.3 mmol) in acetonitrile (75 mL) N-bromosuccinimide (6.14 g, 34.5 mmol) was added. The resulting reaction mixture was stirred at 25 °C for 3 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (75 mL) and washed with water (3 x 30 mL).
  • Step 3 tert-butyl 2-cyano-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate
  • tert-butyl 2-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate 9.54 g, 30 mmol
  • 1,4-dioxane 65 mL
  • water 25.8 mL
  • XantPhos Pd(allyl)]Cl (1.09 g, 1.5 mmol
  • potassium acetate 1.71 g, 14.99 mmol
  • the resulting reaction mixture was degassed with nitrogen for 20 min at 25 °C and the reaction mixture was further stirred at 100 °C for 7 h. After completion of the reaction, the reaction mixture was filtered and the filtrate was diluted with ethyl acetate (120 mL) and washed with water (4 x 40 mL). The combined ethyl acetate layers were concentrated under reduced pressure to obtain tert-butyl 2-cyano-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxylate (7.9 g, 99 % yield).
  • Step 4 tert-butyl 2-(N'-hydroxycarbamimidoyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxylate
  • tert-butyl 2-cyano-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate 10.2 g, 38.6 mmol
  • 50 % aqueous solution of hydroxylamine 8.04 mL, 69.5 mmol
  • reaction mixture was concentrated under reduced pressure to obtain a crude product.
  • the crude product was co-evaporated with ethyl acetate (30 mL) under reduced pressure to obtain tert- butyl 2-(N'-hydroxycarbamimidoyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (10.4 g, 91 % yield).
  • Step 5 tert-butyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxylate
  • tert-butyl 2-(N'-hydroxycarbamimidoyl)-6,7-dihydrothieno[3,2-c]pyridine- 5(4H)-carboxylate 10.1 g, 34 mmol
  • trifluoroacetic anhydride 8.16 mL, 57.7 mmol
  • the resulting reaction mixture was stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (75 mL) and washed with an aqueous saturated sodium bicarbonate solution (3 x 30 mL). The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography to obtain tert-butyl 2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (10 g, 78 % yield).
  • the resulting reaction mixture was stirred at 25 °C for 8 h. After completion of the reaction, the reaction mixture was evaporated to dryness under reduced pressure to obtain a crude product.
  • the crude product was co-evaporated with toluene (2 x 50 mL) under reduced pressure to obtain 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-ium chloride (5.59 g, 99 % yield).
  • Step 7 phenyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)methanone (Compound no.14)
  • benzoic acid 98 mg, 0.8 mmol
  • dichloromethane 10 mL
  • 1-ethyl-3-(3- dimethylaminopropyl)carbodiimide hydrochloride (308 mg, 1.6 mmol
  • 4-(dimethylamino)pyridine (294 mg, 2.4 mmol) was added at 0 °C and stirred for 30 min.
  • the resulting reaction mixture was stirred at 25 °C for 8 h. After completion of the reaction, the reaction mixture was diluted with dichloromethane (150 mL) and washed with water (3 x 60 mL). The combined dichloromethane layers were washed with brine solution (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product.
  • reaction mixture was cooled to 0 °C followed by the addition of 4- chlorobenzenesulfonyl chloride (0.15 g, 0.7 mmol). The resulting reaction mixture was further stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted with dichloromethane (3 x 20 mL). The combined dichloromethane layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain a crude product.
  • Example 4 Preparation of N-(4-chlorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide (Compound no.58) To a solution of 3-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole (200 mg, 0.73 mmol) in dichloromethane (2 mL), triethylamine(0.3 mL, 2.2 mmol) was added.
  • the resulting reaction mixture was further stirred at 25 °C for 8 h. After completion of the reaction, the reaction mixture was extracted with dichloromethane (3 x 50 mL). The combined dichloromethane layers were washed with water (3 x 60 mL), brine solution (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product. The crude product was purified by Combi Flash® to obtain 2-chloro-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (11.5 g, 82 % yield).
  • reaction mixture was stirred for 15 min at 25 °C, followed by the addition of 2-chloro-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (0.25 g, 0.71 mmol) at 0 °C.
  • the resulting reaction mixture was further stirred at 50 °C for 8 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (30 mL).
  • the ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product.
  • the crude product was purified by column chromatography to obtain 2-(4-chlorophenoxy)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (0.12 g, 37 % yield).
  • Example 7 Preparation of (3-chlorophenyl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone (Compound no.116) a) Step 1: 2,3-dibromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrobromide To a stirred solution of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (20 g, 114 mmol) in chloroform (400 mL), bromine (23.46 mL, 455 mmol) was added at 0 °C.
  • Step 2 tert-butyl 2,3-dibromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate : To a stirred suspension of 2,3-dibromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-ium bromide (20 g, 52.9 mmol) in dichloromethane (200 mL), triethylamine (11.25g, 115mmol) and boc-anhydride (13.86 g, 63.5 mmol) were added at 25 °C. The resulting reaction mixture was stirred at 25 °C for 12 h.
  • Step 3 3-bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-ium bromide
  • acetic acid 500 mL
  • zinc 5 g, 76 mmol
  • 10 M aqueous hydrochloric acid solution 20.77 mL, 208 mmol
  • Step 4 tert-butyl 3-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate
  • 3-bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride 18 g, 70.7 mmol
  • dichloromethane 400 mL
  • triethylamine 15.03 g, 148 mmol
  • boc-anhydride 24.63 mL, 106 mmol
  • Step 5 tert-butyl 3-cyano-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate
  • tert-butyl 3-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate 8 g, 25.1 mmol
  • Pd(xanphos)allylCl 0.9 g, 1.26 mmol
  • potassium acetate 1.234 g, 12.6 mmol
  • potassium hexacyanoferrate(II)trihydrate 5.31 g, 12.6 mmol
  • reaction mixture was degassed for 20 min by nitrogen purging. The resulting reaction mixture was further stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was filtered through a Buchner funnel, the filtrate was diluted with water (100 mL) and the product was extracted with ethyl acetate (3 X 50 mL). The combined ethyl acetate layers were washed with water (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product.
  • Step 7 tert-butyl 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxylate
  • tert-butyl 3-(N'-hydroxycarbamimidoyl)-6,7-dihydrothieno[3,2-c]pyridine- 5(4H)-carboxylate 6.5 g, 21.9 mmol
  • triethylamine 4 mL, 33 mmol
  • reaction mixture was cooled to 0 °C followed by the dropwise addition of trifluoroacetic anhydride (6.17 mL, 43.7 mmol). The resulting reaction mixture was further stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (3 x 50 mL). The combined ethyl acetate layers were washed with water (50 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain a crude product.
  • Step 8 3-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole hydrochloride
  • tert-butyl 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxylate 8 g, 21.31 mmol
  • dichloromethane 200 mL
  • 4 M hydrochloric acid solution in 1,4-dioxane 15.98 mL, 63.9 mmol
  • Step 9 (3-chlorophenyl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)methanone (compound no.116)
  • 3-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole hydrochloride 0.2 g, 0.642 mmol
  • dichloromethane 5 mL
  • triethylamine (0.27 mL, 1.93 mmol
  • reaction mixture was cooled to 0 °C followed by the dropwise addition of 3-chlorobenzoyl chloride (0.123 mL, 0.962 mmol). The resulting reaction mixture was further stirred at 25 °C and 16 h. After completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted with dichloromethane (3 x 20 mL). The combined dichloromethane layers were washed with water, dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain a crude product.
  • Example 8 Preparation of 3-(5-(phenylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole (Compound no.143) To a stirred solution of 3-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole hydrochloride (0.18 g, 0.58 mmol) in dichloromethane (5 mL), triethylamine (0.24 mL, 1.73 mmol) was added.
  • reaction mixture was cooled to 0 °C followed by the dropwise addition of benzenesulfonyl chloride (0.148 mL, 1.155 mmol). The resulting reaction mixture was further stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted with dichloromethane (3 x 20 mL). The combined dichloromethane layers were washed with water (20 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain a crude product.
  • Example 10 Preparation of 2-(isopropylamino)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (Compound no.205) To a stirred solution of 2-chloro-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (0.2 g, 0.57 mmol) in acetonitrile (15 mL), propan- 2-amine (0.853 mL, 1.706 mmol) was added.
  • the resulting reaction mixture was stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was diluted with water (50 mL) and extracted with dichloromethane (2 x 50 mL). The combined dichloromethane layers were dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure to obtain a crude product.
  • the crude product was purified by preparative HPLC to obtain 2-(isopropylamino)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (0.077 g, 36 % yield).
  • Example 11 Preparation of N-(3-Fluorophenyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide (Compound no.182) a) Step 1: tert-butyl-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)acetate To a stirred solution of 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,5,6,7-tetrahydrothieno[3,2- c]pyridin-5-ium chloride (0.5 g, 1.604 mmol) in acetonitrile (10 mL), triethylamine (0.47 mL
  • the resulting reaction mixture was stirred at 25 °C for 8 h. After completion of the reaction, the reaction mixture was evaporated to dryness under reduced pressure to obtain a crude product.
  • the crude product was co- evaporated with toluene (2 x 25 mL) under reduced pressure to obtain 2-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetic acid (0.62 g, 91 % yield).
  • the resulting reaction mixture was stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was quenched bu the addition of water (20 mL) and extracted with ethyl acetate (2 x 20 mL). The combined ethyl acetate layers were dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure to obtain a crude product.
  • Example 12 Preparation of N-((4-fluorophenyl)sulfonyl)-2-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide (Compound no.243) To a stirred solution of 2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)acetic acid (0.280 g, 0.840 mmol) in a mixture of tert-butanol (1 mL): dichloromethane (4 mL), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.4 g, 2.1 mmol) and 4-dimethylaminopyridine (0.26
  • reaction mixture was stirred for 15 min at 25 °C followed by the addition of 2-chloro-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (0.25 g, 0.711 mmol) at 0 °C.
  • the resulting reaction mixture was further stirred at 25 °C for 3 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (30 mL).
  • Example 14 Preparation of N-cyclopentyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide (Compound no.245) a) Step 1: tert-butyl 4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate To a stirred solution of 4,5,6,7-tetrahydrothieno[2,3-c]pyridine (46 g, 330 mmol) in dichloromethane (460 mL), triethylamine (138 mL, 991 mmol) was added, followed by the addition of boc-anhydride ( 91.1 mL, 396 mmol) for 1 h at 0 °C.
  • Step 2 tert-butyl 2-bromo-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate
  • a stirred suspension of tert-butyl 4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate (10 g, 41.8 mmol) in acetonitrile (100 mL) N-bromosuccinimide (7.81 g, 43.9 mmol) was added portion wise for 20 min at 25 °C. The resulting reaction mixture was stirred at 25 °C for 14 h.
  • reaction mixture was quenched with ice cold water (100 mL) and extracted with ethyl acetate (2 x 200 mL). The ethyl acetate layer washed with water (2 x 100 mL) followed by brine solution (100 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain a crude product.
  • the crude product was purified by Combi Flash® to obtain tert-butyl 2- bromo-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate (7.4 g, 56 % yield).
  • Step 3 tert-butyl 2-cyano-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate
  • tert-butyl 2-bromo-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate 50 g, 157 mmol
  • palladium(II) dichloride dichloromethane adduct (12.83 g, 15.71 mmol
  • the reaction mixture was degassed with argon for 30 min, and Zinc (II) cyanide (46g, 393 mmol) was added into it.
  • the resulting reaction mixture was stirred at 120 °C for 16 h.
  • the reaction mixture was cooled to 25 °C and diluted with cold water (300 mL) and extracted with ethyl acetate (2 X 300 mL).
  • the combined ethyl acetate layers were washed with 20 % aqueous sodium carbonate solution (300 mL) followed by washing with 0.1 N aqueous hydrochloric acid solution (300 mL) and with aqueous brine solution (300 mL).
  • Step 4 tert-butyl 2-(N'-hydroxycarbamimidoyl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)- carboxylate
  • tert-butyl 2-cyano-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate in (0.41 g, 1.6 mmol) in ethanol (10 mL)
  • triethylamine(0.65 mL, 4.7 mmol) was added followed by addition of hydroxyl amine hydrochloride(0.22 g, 3.11mmol) at 25 °C.
  • the resulting reaction mixture was stirred for 65 °C for 5 h.
  • reaction mixture was cooled to 25 °C and the volatiles were removed under reduced pressure to obtain a residue.
  • residue was washed with n-pentane (5 mL), decanted the pentane layer and solid compound was dried under reduced pressure to obtain crude tert-butyl 2-(N'-hydroxycarbamimidoyl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxylate (0.7 g).
  • Step 5 tert-butyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxylate
  • tert-butyl 2-(N'-hydroxycarbamimidoyl)-4,7-dihydrothieno[2,3-c]pyridine- 6(5H)-carboxylate 28 g, 94.16 mmol
  • pyridine 29.8 mL, 376.6 mmol
  • reaction mixture was cooled to 0 °C and trifluoroacetic anhydride (59.33 g, 5.5 mmol) was added.
  • the resulting reaction mixture was stirred for 24 h at 25 °C.
  • the reaction mixture was quenched with ice cold water (200 mL) and extracted with ethyl acetate (2 x 300 mL).
  • the combined ethyl acetate layer was washed with aqueous saturated sodium bicarbonate solution (2 x 150 mL), brine solution (150 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain a crude product.
  • Step 7 N-cyclopentyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxamide (Compound no.245)
  • 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,5,6,7-tetrahydrothieno[2,3- c]pyridin-6-ium 2,2,2-trifluoroacetate 400 mg, 1.028 mmol
  • dichloromethane 10 mL
  • triethylamine (259.9 mg, 3.083 mmol) was added at 0 °C followed by the addition of isocyanatocyclopentane (172 mg, 1.54 mmol) under nitrogen atmosphere.
  • the resulting reaction mixture was stirred at 25 °C for 12 h. After completion of the reaction, the reaction mixture was quenched with ice-water (10 mL), dichloromethane layer was isolated, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude product. The crude product was precipitated by using 40 mL of 10 % ethyl acetate in hexane. The solid was isolated by filtration and dried under reduced pressure to obtain a crude product.
  • Example 16 Preparation of 3-(6-((3-fluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[2,3- c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole (Compound no.247)
  • 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,5,6,7-tetrahydrothieno[2,3- c]pyridin-6-ium 2,2,2-trifluoroacetate 400 mg, 1.028 mmol
  • dichloromethane 10 mL
  • triethylamine 540 ⁇ L, 3.85 mmol
  • the resultant reaction mixture was stirred at 25 °C for 12 h. After completion of the reaction, the reaction mixture was quenched with ice-water (30 mL), dichloromethane layer was separated, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain a crude product. The resultant crude was precipitated by using 40 mL of 5% ethyl acetate in hexane solution.
  • BIOLOGY EXAMPLES As described herein the compounds of formula (I) show fungicidal activity which is exerted with respect to numerous phytopathogenic fungi which attack on important agricultural crops.
  • the compounds of the present invention were assessed for their activity as described in the following tests:
  • each plate was seeded with a 5 mm size mycelial disc taken from the periphery of an actively growing virulent culture plate of Pyricularia oryzae.
  • the plates were incubated in growth chambers at 25 °C temperature and 60 % relative humidity for seven days and the radial growth was measured and compared to the one of the untreated control.
  • Compounds 4 5 7 8 9 10 11 15 21 25 40 51 53 58 59 61 62 65 69 70 72 73 74 75 76 80 81 83 91 92 94 95 103 110 114 at 300 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive pathogen growth.
  • Example 2 Botrytis cinerea (gray mold): The compounds were dissolved in 0.3 % dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium with the compound in the desired test concentration was dispensed into a 60 mm sterile petri-plate. After solidification, each plate was seeded with a 5 mm size mycelial disc taken from the periphery of an actively growing virulent culture plate of Botrytis cinerea. The plates were incubated in growth chambers at 22 °C temperature and 90 % relative humidity for seven days and the radial growth was measured and compared to the one of the untreated control.
  • Example 3 Alternaria solani (early blight of tomato/potato): The compounds were dissolved in 0.3 % dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium with the compound in the desired test concentration was dispensed into a 60 mm sterile petri-plate. After solidification, each plate was seeded with a 5 mm size mycelial disc taken from the periphery of an actively growing virulent culture plate of Alternaria solani.
  • Example 4 Colletotrichum capsici (anthracnose): The compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium with the compound in the desired test concentration was dispensed into a 60 mm sterile petri-plate.
  • each plate was seeded with a 5 mm size mycelial disc taken from the periphery of an actively growing virulent culture plate of Colletotrichum capsici.
  • the plates were incubated in growth chambers at 25 °C temperature and 60% relative humidity for seven days and the radial growth was measured and compared to the one of the untreated control.
  • Compounds 5 15 21 27 80 at 300 ppm gave more than or equal to 70% control in these tests when compared to the untreated check which showed extensive pathogen growth.
  • Example 5 Corynespora cassiicola (leaf spot of tomato): The compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes.
  • Example 1 Phakopsora pachyrhizi (on soybean plants): The compounds were dissolved in 2 % dimethyl sulfoxide/acetone and then mixed with water containing an emulsifier to the calibrated spray volume of 30 mL. Each spray solution was poured into a spray bottle for further application.
  • Example 1 Phakopsora pachyrhizi (on soybean plants): The compounds were dissolved in 2 % dimethyl sulfoxide/acetone and then mixed with water containing an emulsifier to the calibrated spray volume of 30 mL. Each spray solution was poured into a spray bottle for further application.
  • To test the preventive activity of the compound healthy young soybean plants, raised in the greenhouse, were sprayed with the active compound preparation at the stated application rate inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a conidial suspension containing 2 x10 5 Phakopsora pachyrhizi inoculum.
  • the inoculated plants were then kept in a greenhouse chamber at 22-24 °C temperature and 80-90 % relative humidity for disease expression.
  • a visual assessment of the compound’s performance was carried out by rating the disease severity (0- 100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compound was calculated by comparing the disease rating in the treatment with the one of the untreated control. The treated plants were also assessed for plant damage by recording symptoms like necrosis, chlorosis and stunting.

Abstract

The present invention relates to compounds of formula (I), Formula (I) wherein, R1, R2, Z1, Z2 and m are as defined in the detailed description, and a process for preparing such compounds of formula (I). The present invention also relates to the use of compounds of formula (I) for combating phytopathogenic fungi and to a method for combating phytopathogenic fungi.

Description

Title of the Invention: NOVEL FUSED HETEROCYCLIC COMPOUNDS FOR COMBATING PHYTOPATHOGENIC FUNGI FIELD OF THE INVENTION: The present invention relates to novel fused heterocyclic compounds of formula (I) which are useful in combating phytopathogenic fungi, to a process for preparing such novel fused heterocyclic compounds, to a combination and to a composition comprising such novel fused heterocyclic compounds. The present invention also relates to a method for combating phytopathogenic fungi. BACKGROUND OF THE INVENTION: Oxadiazole compounds are known to be useful in the pharmaceutical field. For instance, WO2013066835 discloses oxadiazole compounds as pharmaceutically active agents. Oxadiazole compounds are also known to be useful as crop protection agents to combat or prevent infestation of microorganisms. For instance, EP0276432, WO2015185485, EP3165093, EP3167716, EP3165093, WO2017110861, WO2017110862, WO2017110864, WO2017211652, WO2017220485, WO2017072247, WO2017076742, WO2018065414, WO2018118781 and WO2018202491 disclose the oxadiazole compounds which are used as fungicides. The oxadiazole compounds reported in the above cited literature have disadvantages in certain aspects, such that they exhibit a narrow spectrum of efficacy or that they do not have satisfactory fungicidal activity, particularly at low application rates. Therefore, there remains a need for the development of new fungicidal compounds, so as to provide novel compounds which are effective against a broader spectrum of fungi, having lower toxicity, higher selectivity, being used at lower dosage rates to reduce or avoid unfavorable environmental or toxicological effects whilst still allowing effective and long lasting control of fungal pathogens. Therefore, it is an objective of the present invention to provide compounds having an improved/enhanced activity and/or a broader efficacy spectrum against phytopathogenic fungi. This objective is achieved by the novel fused heterocyclic compounds of formula (I) and/or their agriculturally useful salts for combating phytopathogenic fungi. SUMMARY OF THE INVENTION: The present invention relates to compounds of formula (I),
Figure imgf000003_0001
wherein, R1, R2, Z1, Z2 and m are as defined in the detailed description. The present invention also relates to a process for preparing the compounds of formula (I). The compounds of formula (I) have been found to be advantageous over the compounds reported in the literature in either of improved fungicidal activity, broader spectrum of biological efficacy, lower application rates, more favourable biological or environmental properties, or enhanced plant compatibility. The present invention further relates to combinations comprising a compound of formula (I) of the present invention and at least one further pesticidally active substance for effectively controlling or preventing phytopathogenic fungi which are difficult to combat. The present invention still further relates to agricultural compositions comprising a compound of formula (I) as such or a compound of formula (I) in combination with a further pesticidally active substance. The present invention still further relates to a method and use of a compound of formula (I) as such or the combination or a composition thereof for combating plant diseases, particularly phytopathogenic fungi. DETAILED DESCRIPTION OF THE INVENTION: DEFINITIONS: The definitions provided herein for the terminologies used in the present disclosure are for illustrative purpose only and in no manner limit the scope of the present invention disclosed in the present disclosure. As used herein, the terms “comprises”, “comprising”, “includes”, “including”, “has”, “having”, “contains”, “containing”, “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method. The transitional phrase “consisting of” excludes any element, step or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase “consisting of” appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole. The transitional phrase “consisting essentially of” is used to define a composition or method that includes materials, steps, features, components or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term “consisting essentially of” occupies a middle ground between “comprising” and “consisting of”. Further, unless expressly stated to the contrary, “or” refers to an inclusive “or” and not to an exclusive “or”. For example, a condition A “or” B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present). Also, the indefinite articles “a” and “an” preceding an element or component of the present invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore “a” or “an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular. The term "undesired microorganisms" or "phytopathogenic microorganisms" such as fungal or bacterial pathogens includes namely Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes and Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae. The term “agronomic” refers to the production of field crops such as for food, feed and fiber and includes the growth of corn, soybeans and other legumes, rice, cereal (e.g., wheat, oats, barley, rye, rice, maize), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifer and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone and citrus), small fruit (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives). The term “nonagronomic” refers to other than field crops, such as horticultural crops (e.g., greenhouse, nursery or ornamental plants not grown in a field), residential, agricultural, commercial and industrial structures, turf (e.g., sod farm, pasture, golf course, lawn, sports field, etc.), wood products, stored product, agro-forestry and vegetation management, public health (i.e. human) and animal health (e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as wildlife) applications. Nonagronomic applications include protecting an animal from a fungal or microbial infection by administering a biologically effective amount of a compound of the present invention, typically in the form of a composition formulated for veterinary use, to the animal to be protected. As referred to in the present disclosure and claims, the terms “fungicidal” and “microbiocidal” refers to observable effects on micro-organisms to provide protection of an animal from the diseases. Microbiocidal effects typically relate to diminishing the occurrence or activity of the target micro-organisms. Such effects include necrosis, death and retarded growth, lessened ability to remain on or in the host animal, reduced feeding and inhibition of reproduction. These effects on micro-organisms provide control (including prevention, reduction or elimination) of infestation or infection of the animal. The meaning of various terms used in the description shall now be illustrated. The term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” or - N(alkyl) or alkylcarbonylalkyl or alkylsuphonylamino includes straight-chain or branched C1 to C24 alkyl, preferably C1 to C15 alkyl, more preferably C1 to C10 alkyl, most preferably C1 to C6 alkyl. Non- limiting examples of alkyl include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2- methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2- dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and l-ethyl-2-methylpropyl or the different isomers. If the alkyl is at the end of a composite substituent, as, for example, in alkylcycloalkyl, the part of the composite substituent at the start, for example the cycloalkyl, may be mono- or polysubstituted identically or differently and independently by alkyl. The same also applies to composite substituents in which other radicals, for example alkenyl, alkynyl, hydroxy, halogen, carbonyl, carbonyloxy and the like, are at the end. The term “alkenyl”, used either alone or in compound words includes straight-chain or branched C2 to C24 alkenes, preferably C2 to C15 alkenes, more preferably C2 to C10 alkenes, most preferably C2 to C6 alkenes. Non-limiting examples of alkenes include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-l-propenyl, l-methyl-2 -propenyl, 2- methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1- butenyl, 3-methyl-1-butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3- butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2 -propenyl, 1-ethyl-1-propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4- hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1- pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l- methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4- pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, l,l-dimethyl-3-butenyl, 1,2-dimethyl-l-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3- dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3- dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3- dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, l-ethyl-3-butenyl, 2-ethyl- 1-butenyl, 2- ethyl-2-butenyl, 2-ethyl-3-butenyl, l,l,2-trimethyl-2-propenyl, 1-ethyl-l-methyl-2-propenyl, l-ethyl-2- methyl-l-propenyl and l-ethyl-2-methyl-2-propenyl and the different isomers. “Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl as a part of a composite substituent, for example haloalkenyl and the like, unless defined specifically elsewhere. Non-limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3- butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l- methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl -2- propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, l-methyl-3- pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-l-pentynyl, 3- methyl-4-pentynyl, 4-methyl-l-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, l,l-dimethyl-3- butynyl, l,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl, l-ethyl-2-butynyl, l- ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-l-methyl-2-propynyl and the different isomers. This definition also applies to alkynyl as a part of a composite substituent, for example haloalkynyl etc., unless specifically defined elsewhere. The term “alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. The term “cycloalkyl” means alkyl closed to form a ring. Non-limiting examples include cyclopropyl, cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as a part of a composite substituent, for example cycloalkylalkyl etc., unless specifically defined elsewhere. The term “cycloalkenyl” means alkenyl closed to form a ring including monocyclic, partially unsaturated hydrocarbyl groups. Non-limiting examples include cyclopropenyl, cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as a part of a composite substituent, for example cycloalkenylalkyl etc., unless specifically defined elsewhere. The term “cycloalkynyl” means alkynyl closed to form a ring including monocyclic, partially unsaturated groups. Non-limiting examples include cyclopropynyl, cyclopentynyl and cyclohexynyl. This definition also applies to cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere. The term “cycloalkoxy”, “cycloalkenyloxy” and the like are defined analogously. Non limiting examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as a part of a composite substituent, for example cycloalkoxy alkyl etc., unless specifically defined elsewhere. The term “halogen”, either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Non- limiting examples of “haloalkyl” include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl, and 1,1,1-trifluoroprop-2-yl. This definition also applies to haloalkyl as a part of a composite substituent, for example haloalkylaminoalkyl etc., unless specifically defined elsewhere. The terms “haloalkenyl”, “haloalkynyl” are defined analogously except that, instead of alkyl groups, alkenyl and alkynyl groups are present as a part of the substituent. The term “haloalkoxy” means straight-chain or branched alkoxy groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkoxy include 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 l,l,l-trifluoroprop-2-oxy. This definition also applies to haloalkoxy as a part of a composite substituent, for example haloalkoxyalkyl etc., unless specifically defined elsewhere. The term “haloalkylthio” means straight-chain or branched alkylthio groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1- bromoethylthio, 1- fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2- chloro-2- fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2- trichloroethylthio, pentafluoroethylthio and l,l,l-trifluoroprop-2-ylthio. This definition also applies to haloalkylthio as a part of a composite substituent, for example haloalkylthioalkyl etc., unless specifically defined elsewhere. Non-limiting examples of “haloalkylsulfinyl” include CF3S(O), CCl3S(O), CF3CH2S(O) and CF3CF2S(O). Non-limiting examples of “haloalkylsulfonyl” include CF3S(O)2, CCl3S(O)2, CF3CH2S(O)2 and CF3CF2S(O)2. The term “hydroxy” means –OH, Amino means –NRR, wherein R can be H or any possible substituent such as alkyl. Carbonyl means -C(=O)- , carbonyloxy means -OC(=O)-, sulfinyl means SO, sulfonyl means S(O)2. The term “alkoxy” used either alone or in compound words includes C1 to C24 alkoxy, preferably C1 to C15 alkoxy, more preferably C1 to C10 alkoxy, most preferably C1 to C6 alkoxy. Examples of alkoxy include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1- dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1- ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2- methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3- dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2- ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and l-ethyl-2- methylpropoxy and the different isomers. This definition also applies to alkoxy as a part of a composite substituent, for example haloalkoxy, alkynylalkoxy, etc., unless specifically defined elsewhere. The term “alkoxyalkyl” denotes an alkoxy substitution on alkyl. Non-limiting examples of “alkoxyalkyl” include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2. The term “alkoxyalkoxy” denotes an alkoxy substitution on alkoxy. The term “alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1- dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2- dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1- methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3- dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2- trimethylpropylthio, 1-ethyl-1-methylpropylthio and l-ethyl-2-methylpropylthio and the different isomers. Halocycloalkyl, halocycloalkenyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylcarbonyl, cycloalkylcarbonyl, haloalkoxylalkyl, and the like, are defined analogously to the above examples. The term “alkylthioalkyl” denotes an alkylthio substitution on alkyl. Non-limiting examples of “alkylthioalkyl” include -CH2SCH2, -CH2SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and CH3CH2SCH2CH2. “Alkylthioalkoxy” denotes an alkylthio substitution on alkoxy. The term “cycloalkylalkylamino” denotes a cycloalkyl substitution on alkyl amino. The terms “alkoxyalkoxyalkyl”, “alkylaminoalkyl”, “dialkylaminoalkyl”, “cycloalkylaminoalkyl”, “cycloalkylaminocarbonyl” and the like, are defined analogously to “alkylthioalkyl” or “cycloalkylalkylamino”. The term “alkoxycarbonyl” is an alkoxy group bonded to a skeleton via a carbonyl group (-CO-). This definition also applies to alkoxycarbonyl as a part of a composite substituent, for example cycloalkylalkoxycarbonyl and the like, unless specifically defined elsewhere. The term “alkoxycarbonylalkylamino” denotes an alkoxy carbonyl substitution on alkyl amino. “Alkylcarbonylalkylamino” denotes an alkyl carbonyl substitution on alkyl amino. The terms alkylthioalkoxycarbonyl, cycloalkylalkylaminoalkyl and the like are defined analogously. Non-limiting examples of “alkylsulfinyl” include methylsulphinyl, ethylsulphinyl, propylsulphinyl, 1- methylethylsulphinyl, butylsulphinyl, 1-methylpropylsulphinyl, 2-methylpropylsulphinyl, 1,1- dimethylethylsulphinyl, pentylsulphinyl, 1-methylbutylsulphinyl, 2-methylbutylsulphinyl, 3- methylbutylsulphinyl, 2,2-dimethylpropylsulphinyl, 1-ethylpropylsulphinyl, hexylsulphinyl, 1,1- dimethylpropylsulphinyl, 1,2-dimethylpropylsulphinyl, 1-methylpentylsulphinyl, 2- methylpentylsulphinyl, 3-methylpentylsulphinyl, 4-methylpentylsulphinyl, 1,1- dimethylbutylsulphinyl, 1,2-dimethylbutylsulphinyl, 1,3-dimethylbutylsulphinyl, 2,2- dimethylbutylsulphinyl, 2,3-dimethylbutylsulphinyl, 3,3-dimethylbutylsulphinyl, 1- ethylbutylsulphinyl, 2-ethylbutylsulphinyl, 1,1,2-trimethylpropylsulphinyl, 1,2,2- trimethylpropylsulphinyl, 1-ethyl-1-methylpropylsulphinyl and 1-ethyl-2-methylpropylsulphinyl and the different isomers. The term “arylsulfinyl” includes Ar-S(O), wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphinyl as a part of a composite substituent, for example haloalkylsulphinyl etc., unless specifically defined elsewhere. Non-limiting examples of “alkylsulfonyl” include methylsulphonyl, ethylsulphonyl, propylsulphonyl, 1-methylethylsulphonyl, butylsulphonyl, 1-methylpropylsulphonyl, 2-methylpropylsulphonyl, 1,1- dimethylethylsulphonyl, pentylsulphonyl, 1-methylbutylsulphonyl, 2-methylbutylsulphonyl, 3- methylbutylsulphonyl, 2,2-dimethylpropylsulphonyl, 1-ethylpropylsulphonyl, hexylsulphonyl, 1,1- dimethylpropylsulphonyl, 1,2-dimethylpropylsulphonyl, 1-methylpentylsulphonyl, 2- methylpentylsulphonyl, 3-methylpentylsulphonyl, 4-methylpentylsulphonyl, 1,1- dimethylbutylsulphonyl, 1,2-dimethylbutylsulphonyl, 1,3-dimethylbutylsulphonyl, 2,2- dimethylbutylsulphonyl, 2,3-dimethylbutylsulphonyl, 3,3-dimethylbutylsulphonyl, 1- ethylbutylsulphonyl, 2-ethylbutylsulphonyl, 1,1,2-trimethylpropylsulphonyl, 1,2,2- trimethylpropylsulphonyl, 1-ethyl-1-methylpropylsulphonyl and l-ethyl-2-methylpropylsulphonyl and the different isomers. The term “arylsulfonyl” includes Ar-S(O)2, wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphonyl as a part of a composite substituent, for example alkylsulphonylalkyl etc., unless defined elsewhere. “Alkylamino”, “dialkylamino”, and the like, are defined analogously to the above examples. The term “carbocycle or carbocyclic” includes an “aromatic carbocyclic ring system” and a “non- aromatic carbocylic ring system” or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which the ring may be aromatic or non-aromatic (where aromatic indicates that the Huckel rule is satisfied and non-aromatic indicates that the Huckel rule is not statisfied). The term “heterocycle or heterocyclic” includes an “aromatic heterocycle or heteroaryl ring system” and a “non-aromatic heterocycle ring system” or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which the ring may be aromatic or non-aromatic, wherein the heterocycle ring contains at least one heteroatom selected from N, O, S(O)0-2, and or C ring member of the heterocycle may be replaced by C(=O), C(=S), C(=CR*R*) and C=NR*, * indicates integers. The term “non-aromatic heterocycle” or “non-aromatic heterocyclic” means a three- to fifteen- membered, preferably three- to twelve- membered, saturated or partially unsaturated heterocycle containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur: mono, bi- or tricyclic heterocycles which contain, in addition to carbon ring members, one to three nitrogen atoms and/or one oxygen or sulphur atom or one or two oxygen and/or sulphur atoms; if the ring contains more than one oxygen atom, they are not directly adjacent; non-limiting examples thietanyl, oxetanyl, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3- isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4- pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4- thiazolidinyl, 5-thiazolidinyl, 1-imidazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4- oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4- triazolidin-1-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4- triazolidin-1-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4- dihydrothien-3-yl, pyrrolinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2- isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4- isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3- isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2- isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-l-yl, 2,3-dihydropyrazol- 2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol- 1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-l- yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2- yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4- dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, pyrazynyl, morpholinyl, thiomorphlinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2- tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4- hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl, 1,2,4- hexahydrotriazin-3-yl, cycloserines, 2,3,4,5-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or -7- yl, 3,4,5,6-tetra-hydro[2H]azepin-2- or -3- or -4- or -5- or -6- or-7-yl, 2,3,4,7- tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or-7- yl, 2,3,6,7-tetrahydro[1H]azepin-1- or - 2- or -3- or -4- or -5- or -6- or -7- yl, hexahydroazepin-1- or -2- or -3- or -4- yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[1 H]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, 2,3,4,7-tetrahydro[1H]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, 2,3,6,7-tetrahydro[1H]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, hexahydroazepin-1- or -2- or -3- or -4- yl, tetra- and hexahydro-1,3- diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl, tetra- and hexahydro-1,3-dioxepinyl, tetra- and hexahydro-1,4-dioxepinyl. This definition also applies to heterocyclyl as a part of a composite substituent, for example heterocyclylalkyl etc., unless specifically defined elsewhere. The term “heteroaryl” or “aromatic heterocyclic” means 5 or 6-membered, fully unsaturated monocyclic ring systems containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur; if the ring contains more than one oxygen atom, they are not directly adjacent; 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom; 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom as ring members, non-limiting examples furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,3,4-triazolyl, tetrazolyl; nitrogen-bonded 5-membered heteroaryl containing one to four nitrogen atoms, or benzofused nitrogen-bonded 5-membered heteroaryl containing one to three nitrogen atoms: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms as ring members and in which two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member may be bridged by a buta-1,3-diene-l,4-diyl group in which one or two carbon atoms may be replaced by nitrogen atoms, where these rings are attached to the skeleton via one of the nitrogen ring members, non-limiting examples 1-pyrrolyl, 1- pyrazolyl, 1,2,4-triazol-l- yl, 1-imidazolyl, 1,2,3-triazol-l-yl and 1,3,4-triazol-l-yl. 6-membered heteroaryl which contains one to four nitrogen atoms: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain, respectively, one to three and one to four nitrogen atoms as ring members, non-limiting examples 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4- pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin- 3-yl and 1,2,4,5-tetrazin-3-yl; benzofused 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulphur atom: non-limiting examples indol-l-yl, indol- 2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, benzimidazol-l-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, indazol-l-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol- 6-yl, indazol-7-yl, indazol-2-yl, l-benzofuran-2-yl, l-benzofuran-3-yl, l-benzofuran-4-yl, l-benzofuran- 5-yl, 1-benzofuran- 6-yl, l-benzofuran-7-yl, l-benzothiophen-2-yl, l-benzothiophen-3-yl, l- benzothiophen-4-yl, 1- benzothiophen-5-yl, l-benzothiophen-6-yl, l-benzothiophen-7-yl, 1,3- benzothiazol-2-yl, 1,3- benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3- benzothiazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl and 1,3-benzoxazol-7-yl; benzofused 6-membered heteroaryl which contains one to three nitrogen atoms: non-limiting examples quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-l-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl and isoquinolin-8-yl. The term “trialkylsilyl” includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom such as trimethylsilyl, triethylsilyl and t-butyl-dimethylsilyl. “Halotrialkylsilyl” denotes at least one of the three alkyl radicals is partially or fully substituted with halogen atoms which may be the same or different. The term”alkoxytrialkylsilyl” denotes at least one of the three alkyl radicals is substituted with one or more alkoxy radicals which may be the same or different. The term “trialkylsilyloxy” denotes a trialkylsilyl moiety attached through oxygen. Non-limiting examples of “alkylcarbonyl” include C(=O)CH3, C(=O)CH2CH2CH3 and C(=O)CH(CH3)2. Non-limiting examples of “alkoxycarbonyl” include CH3OC(=O), CH3CH2OC(=O), CH3CH2CH2OC(=O), (CH3)2CHOC(=O) and the different butoxy -or pentoxycarbonyl isomers. Non- limiting examples of “alkylaminocarbonyl” include CH3NHC(=O), CH3CH2NHC(=O), CH3CH2CH2NHC(=O), (CH3)2CHNHC(=O) and the different butylamino -or pentylaminocarbonyl isomers. Non-limiting examples of “dialkylaminocarbonyl” include (CH3)2NC(=O), (CH3CH2)2NC(=O), CH3CH2(CH3)NC(=O), CH3CH2CH2(CH3)NC(=O) and (CH3)2CHN(CH3)C(=O). Non-limiting examples of “alkoxyalkylcarbonyl” include CH3OCH2C(=O), CH3OCH2CH2C(=O), CH3CH2OCH2C(=O), CH3CH2CH2CH2OCH2C(=O) and CH3CH2OCH2CH2C(=O). Non-limiting examples of “alkylthioalkylcarbonyl” include CH3SCH2C(=O), CH3SCH2CH2C(=O), CH3CH2SCH2C(=O), CH3CH2CH2CH2SCH2C(=O) and CH3CH2SCH2CH2C(=O). The term haloalkylsufonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkyl amino and the like are defined analogously Non-limiting examples of “alkylaminoalkylcarbonyl” include CH3NHCH2C(=O), CH3NHCH2CH2C(=O), CH3CH2NHCH2C(=O), CH3CH2CH2CH2NHCH2C(=O) and CH3CH2NHCH2CH2C(=O). The term “amide” means A-R'C=ONR''-B, wherein R' and R'' indicate substituents and A and B indicate any group. The term “thioamide” means A-R'C=SNR''-B, wherein R' and R'' indicates substituent and A and B indicate any group. The total number of carbon atoms in a substituent group is indicated by the “Ci-Cj” prefix where i and j are numbers from 1 to 21. For example, C1-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH3OCH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2. In the above recitations, when a compound of Formula (I) is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen. When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents. Further, when the subscript m in (R)m indicates an integer ranging from for example 0 to 4 then the number of substituents may be selected from the integers between 0 and 4 inclusive. When a group contains a substituent which can be hydrogen, then, when this substituent is taken as hydrogen, it is recognized that said group is being un-substituted. The embodiments herein and the various features and advantageous details thereof are explained with reference to the non-limiting embodiments in the description. Descriptions of well-known components and processing techniques are omitted so as to not unnecessarily obscure the embodiments herein. The examples used herein are intended merely to facilitate an understanding of ways in which the embodiments herein may be practiced and to further enable those of skilled in the art to practice the embodiments herein. Accordingly, the examples should not be construed as limiting the scope of the embodiments herein. The description of the specific embodiments will so fully reveal the general nature of the embodiments herein that others can, by applying current knowledge, readily modify and/or adapt for various applications such specific embodiments without departing from the generic concept, and, therefore, such adaptations and modifications should and are intended to be comprehended within the meaning and range of equivalents of the disclosed embodiments. It is to be understood that the phraseology or terminology employed herein is for the purpose of description and not of limitation. Therefore, while the embodiments herein have been described in terms of preferred embodiments, those skilled in the art will recognize that the embodiments herein can be practiced with modification within the spirit and scope of the embodiments as described herein. Any discussion of documents, acts, materials, devices, articles and the like that has been included in this specification is solely for the purpose of providing a context for the disclosure. It is not to be taken as an admission that any or all of these matters form a part of the prior art base or were common general knowledge in the field relevant to the disclosure as it existed anywhere before the priority date of this application. The numerical values mentioned in the description and the description/claims though might form a critical part of the present invention, any deviation from such numerical values shall still fall within the scope of the present invention if that deviation follows the same scientific principle as that of the present invention disclosed in the present invention. The inventive compounds of the present invention may, if appropriate, be present as mixtures of different possible isomeric forms, especially of stereoisomers, for example E and Z, threo and erythro, and also optical isomers, but if appropriate also of tautomers. Both the E and the Z isomers, and also the threo and erythro isomers, and the optical isomers, any desired mixtures of these isomers and the possible tautomeric forms are disclosed and claimed. The term “microorganisms” for the purpose of the present disclosure includes but is not limited to fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, insects and rodents. The term “plant” is understood here to 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 transgenic plants and including the plant cultivars which are protectable and non-protectable by plant breeders’ rights. For the purpose of the present disclosure the term “plant” includes a living organism of the kind exemplified by trees, shrubs, herbs, grasses, ferns, and mosses, typically growing in a site, absorbing water and required substances through its roots, and synthesizing nutrients in its leaves by photosynthesis. Examples of “plant” for the purpose of the present invention include but are not limited to agricultural crops such as wheat, rye, barley, triticale, oats or rice; beet, e.g. sugar beet or fodder beet; fruits and fruit trees, such as pomes, stone fruits or soft fruits, e.g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit and citrus trees, such as oranges, lemons, grapefruits or mandarins; any horticultural plants, vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; cucurbitaceae; oleaginous plants; energy and raw material plants, such as cereals, corn, soybean, other leguminous plants, rape, sugar cane or oil palm; tobacco; nuts; coffee; tea; cacao; bananas; peppers; vines (table grapes, grape juice and grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, e.g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants. Preferably, the plant for the purpose of the present invention includes but is not limited to cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and vegetables, ornamentals, any floricultural plants and other plants for the use of humans and animals. The term “plant parts” is understood to mean all parts and organs of plants above and below the ground. For the purpose of the present disclosure the term plant part includes but is not limited to cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots including taproots, lateral roots, root hairs, root apex, root cap, rhizomes, slips, shoots, fruits, fruit bodies, bark, stem, buds, auxillary buds, meristems, nodes and internodes. The term “locus thereof” includes soil, surroundings of plant or plant parts and equipment or tools used before, during or after sowing/planting a plant or a plant part. Application of the compounds of the present disclosure or the compounds of the present disclosure in a composition, optionally comprising other compatible compounds, to a plant or a plant material or locus thereof includes application by a technique known to a person skilled in the art which includes but is not limited to spraying, coating, dipping, fumigating, impregnating, injecting and dusting. The term “applied” means adhered to a plant or plant part either physically or chemically including impregnation. In view of the above, the present invention provides a compound of formula (I),
Figure imgf000015_0001
wherein, Z1 and Z2 represent CHR2 or N-R3; provided that (i) both Z1 and Z2 are not CHR2 simultaneously; (ii) both Z1 and Z2 are not N-R3 simultaneously; R1 is C1-C6 haloalkyl; R2 is selected from the group consisting of hydrogen, halogen, cyano, nitro, thiol, amino, hydroxy, C1- C6-alkyl, C2-C6-alkenyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1- C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-haloalkenyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6- haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-haloalkylsulfonyl, C1-C6-alkylsulfonyl, C1- C6-alkylamino, C1-C6-dialkylamino and C3-C8-cycloalkylamino; wherein the aliphatic or cyclic moieties of R2 may optionally be substituted with one or more groups of R2a; R2a is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C1- C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6- haloalkylthio, C3-C8-cycloalkyl and C1-C6-alkoxy-C1-C6-alkyl; R3 is selected from the group consisting of C1-C6-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1- C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C3-C8-halocycloalkyl, C6-C10-aryl, C6- C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl, C3-C8-heterocyclyl-C1-C6-alkyl, -(CHR9)n-C(=O)-R4, - C(=O)-(CHR9)n-R4, -C(=O)-(CHR9)n-O-R4, -C(=O)-(CHR9)n-S-R4, -C(=O)-(CHR9)n-N(R5)(R6), - (CHR9)n-(C=O)-C(=O)-R4, -(CHR9)n-C(=O)-O-R4, -(C=O)-C(=O)-O-R4, -(CHR9)n-C(=O)-(CHR9)n - N(R5)(R6), -(CHR9)n-(C=O)-C(=O)-N(R5)(R6), -S(O)2-R4, -(CHR9)n-N(R5)-C(=O)-R4, -(CHR9)n- N(R5)-C(=O)-O-R4, -(CHR9)n-C(=O)-N(R5)-S(=O)n-R4, -(CHR9)n-N(R5)-S(=O)n-R4, -(CHR9)n-N(R5)- C(=O)-N(R5)(R6), -S(O)2-N(R5)(R6); wherein the aliphatic or cyclic moieties of R3 may optionally be substituted with one or more groups of R3a; R3a is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thio, amino, C1- C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C6-haloalkoxy, C1-C6- alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, phenyl, benzyl, and C3-C10-heterocyclyl; wherein each group of R3a may optionally be substituted with one or more groups selected from halogen, cyano, nitro, hydroxyl, thio, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6- alkoxy, C1-C4-alkoxy- C1-C4-alkyl or C1-C6-haloalkoxy; R4 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6 alkoxy-C1-C6-alkyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, C1-C6-dialkylamino, C3-C8-cycloalkylamino, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl, C3-C8-heterocyclyl- C1-C6-alkyl; each group of R4 may optionally be substituted with one or more groups R4a; R4a is selected from the group consisting of halogen, cyano, amino, C1-C6-alkylamino, C1-C6- dialkylamino, C1-C6-alkyl, C1-C6-alkylthio, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy and phenoxy; R5 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl; R6 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3- C8-heterocyclyl, C3-C8-heterocyclyl-C1-C6-alkyl; each group of R6 may optionally be substituted with one or more groups R6a; R6a may be optionally substituted with halogen, cyano, amino, C1-C6-alkylamino, C1-C6 dialkylamino, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkyl, C1-C6-alkylthio, C3-C6-cycloalkyl, C3-C6-cycloalkoxy and phenoxy; or R5 and R6 together with the atom to which they are attached may form a fused or non-fused 4-8 membered heterocyclic ring containing at least one heteroatom selected from O, S(=O)0-2, or NR7 and which may be optionally substitutes with one or more groups R8 ; R7 is selected from the group consisting of hydrogen, C1-6-alkyl and C3-6-cycloalkyl; R8 is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8- cycloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C6-C10-aryloxy, C6-C10- arylthio, C6-C10-aryl-C1-C6-alkoxy, C3-C10-heterocyclyl and C3-C10-heterocyclyloxy; R9 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl; each group of R2 to R9, R2a, R3a, R4a and R6a may be optionally substituted with one or more groups selected from the group consisting of halogen, cyano, nitro, R’, OR’, SR’, N(R’)2, COR’ and CON(R’)2; R’ is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1- C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkoxy, C6-C10-aryl-C1-C6-alkyl and C3-C10-heterocyclyl; n is an integer selected from 0 to 3; or N-oxides, metal complexes, isomers, polymorphs, or agriculturally acceptable salts thereof. In a preferred embodiment, the present invention provides the compound of formula (I) wherein R1 is selected from the group consisting of CF3, CF2H and CF2Cl. In one embodiment, the compound of formula (I) is represented by a compound of formula (Ia),
Figure imgf000018_0001
Formula (Ia) wherein, R1, R2, R3, Z1 and Z2 are as defined in the above detailed description and and m is an integer selected from 0 to 3. In another embodiment, the compound of formula (I) is represented by a compound of formula (Ib),
Figure imgf000018_0002
Formula (Ib) wherein, R1, R2, R3, Z1 and Z2 are as defined in the above detailed description and m is an integer selected from 0 to 3. In yet another embodiment, the compound of formula (I) is represented by a compound of formula (Ic),
Figure imgf000018_0003
Formula (Ic) wherein, R1, R2, and R3 are as defined in the above detailed description and m is an integer selected from 0 to 3. In yet another embodiment, the compound of formula (I) is represented by a compound of formula (Id),
Figure imgf000018_0004
Formula (Id) wherein, R1, R2, and R3 are as defined in the above detailed description and m is an integer selected from 0 to 3. In yet another embodiment, the compound of formula (I) is represented by a compound of formula (Ie),
Figure imgf000019_0001
Formula (Ie) wherein, R1, R2, and R3 are as defined in the above detailed description and m is an integer selected from 0 to 3. In yet another embodiment, the compound of formula (I) is represented by a compound of formula (If),
Figure imgf000019_0002
Formula (If) wherein, R1, R2, and R3 are as defined in the above detailed description and m is an integer selected from 0 to 3. In one preferred embodiment, the present invention provides a compound of formula (I), wherein Z1 represents N-R3 and Z2 represents CHR2; and the radicals R1, R2, R3, R4, R5, R6, R7, R8, R9 and n have the same meanings as given for the compounds of formula (I) in the above detailed description. In another preferred embodiment, the present invention provides a compound of formula (I), wherein Z1 represents CHR2 and Z2 represents N-R3; and the radicals R1, R2, R3, R4, R5, R6, R7, R8, R9 and n have the same meanings as given for the compounds of formula (I) in the above detailed description. In one embodiment, the present invention provides a compound of formula (I),
Figure imgf000019_0003
Formula (I) wherein, Z1 and Z2 represent CHR2 or N-R3; provided that (i) both Z1 and Z2 are not CHR2 simultaneously; (ii) both Z1 and Z2 are not N-R3 simultaneously; R1 is selected from the group consisting of CF3, CHF2 and CF2Cl; R2 is selected from the group consisting of hydrogen, halogen, cyano, nitro, thiol, amino, hydroxy, C1- C6-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6- alkoxy-C1-C6-alkyl; R3 is selected from the group consisting of C1-C6-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6- alkyl, C3-C8-halocycloalkyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl, C3-C8- heterocyclyl-C1-C6-alkyl, -(CHR9)n-C(=O)-R4, -C(=O)-(CHR9)n-R4, -C(=O)-(CHR9)n-O-R4, -C(=O)- (CHR9)n-S-R4, -C(=O)-(CHR9)n-N(R5)(R6), -(CHR9)n-(C=O)-C(=O)-R4, -(CHR9)n-C(=O)-O-R4, - (C=O)-C(=O)-O-R4, -(CHR9)n-C(=O)-(CHR9)n-N(R5)(R6), -(CHR9)n-(C=O)-C(=O)-N(R5)(R6), -S(O)2- R4, -(CHR9)n-N(R5)-C(=O)-R4, -(CHR9)n-N(R5)-C(=O)-O-R4, -(CHR9)n-C(=O)-N(R5)-S(=O)n-R4, - (CHR9)n-N(R5)-S(=O)n-R4 and -S(O)2-N(R5)(R6); wherein the aliphatic or cyclic moieties of R3 may optionally be substituted with one or more groups of R3a; R3a is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thio, amino, C1- C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C6-haloalkoxy, C1-C6- alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, phenyl, benzyl, and C3-C10-heterocyclyl; wherein each group of R3a may optionally be substituted with one or more groups selected from halogen, cyano, nitro, hydroxyl, thio, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6- alkoxy, C1-C4-alkoxy-C1-C4-alkyl or C1-C6-haloalkoxy; R4 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6 alkoxy-C1-C6-alkyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, C1-C6-dialkylamino, C3-C8-cycloalkylamino, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl and C3-C8- heterocyclyl-C1-C6-alkyl; each group of R4 may optionally be substituted with one or more groups R4a; R4a is selected from the group consisting of halogen, cyano, amino, C1-C6-alkylamino, C1-C6- dialkylamino, C1-C6-alkyl, C1-C6-alkylthio, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy and phenoxy; R5 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl; R6 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3- C8-heterocyclyl and C3-C8-heterocyclyl-C1-C6-alkyl; each group of R6 may optionally be substituted with one or more groups R6a; R6a may be optionally substituted with halogen, cyano, amino, C1-C6-alkylamino, C1-C6 dialkylamino, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkyl, C1-C6-alkylthio, C3-C6-cycloalkyl, C3-C6-cycloalkoxy and phenoxy; or R5 and R6 together with the atom to which they are attached may form a fused or non-fused 4-8 membered heterocyclic ring containing at least one heteroatom selected from O, S(=O)0-2, or NR7 and which may be optionally substituted with one or more groups R8 ; R7 is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl; R8 is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylthio and C3-C8-cycloalkyl; R9 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl; n is an integer selected from 0 to 2. In another embodiment, the present invention provides a compound of formula (I),
Figure imgf000021_0001
Formula (I) wherein, Z1 represents N-R3 and Z2 represents CHR2; R1 is selected from the group consisting of CF3, CHF2 and CF2Cl; R2 is selected from the group consisting of hydrogen, halogen, cyano, nitro, thiol, amino, hydroxy, C1- C6-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6- alkoxy-C1-C6-alkyl; R3 is selected from the group consisting of C1-C6-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6- alkyl, C3-C8-halocycloalkyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl, C3-C8- heterocyclyl-C1-C6-alkyl, -(CHR9)n-C(=O)-R4, -C(=O)-(CHR9)n-R4, -C(=O)-(CHR9)n-O-R4, -C(=O)- (CHR9)n-S-R4, -C(=O)-(CHR9)n-N(R5)(R6), -(CHR9)n-(C=O)-C(=O)-R4, -(CHR9)n-C(=O)-O-R4, - (C=O)-C(=O)-O-R4, -(CHR9)n-C(=O)-(CHR9)n-N(R5)(R6), -(CHR9)n-(C=O)-C(=O)-N(R5)(R6), -S(O)2- R4, -(CHR9)n-N(R5)-C(=O)-R4, -(CHR9)n-N(R5)-C(=O)-O-R4, -(CHR9)n-C(=O)-N(R5)-S(=O)n-R4, - (CHR9)n-N(R5)-S(=O)n-R4 and -S(O)2-N(R5)(R6); wherein the aliphatic or cyclic moieties of R3 may optionally be substituted with one or more groups of R3a; R3a is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thio, amino, C1- C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C6-haloalkoxy, C1-C6- alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, phenyl, benzyl, and C3-C10-heterocyclyl; wherein each group of R3a may optionally be substituted with one or more groups selected from halogen, cyano, nitro, hydroxyl, thio, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6- alkoxy, C1-C4-alkoxy-C1-C4-alkyl or C1-C6-haloalkoxy; R4 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6 alkoxy-C1-C6-alkyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, C1-C6-dialkylamino, C3-C8-cycloalkylamino, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl and C3-C8- heterocyclyl-C1-C6-alkyl; each group of R4 may optionally be substituted with one or more groups R4a; R4a is selected from the group consisting of halogen, cyano, amino, C1-C6-alkylamino, C1-C6- dialkylamino, C1-C6-alkyl, C1-C6-alkylthio, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy and phenoxy; R5 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl; R6 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6 alkoxy-C1-C6-alkyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl and C3-C8-heterocyclyl-C1-C6-alkyl; each group of R6 may optionally be substituted with one or more groups R6a; R6a may be optionally substituted with halogen, cyano, amino, C1-C6-alkylamino, C1-C6 dialkylamino, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkyl, C1-C6-alkylthio, C3-C6-cycloalkyl, C3-C6-cycloalkoxy and phenoxy; or R5 and R6 together with the atom to which they are attached may form a fused or non-fused 4-8 membered heterocyclic ring containing at least one heteroatom selected from O, S(=O)0-2, or NR7 and which may be optionally substituted with one or more groups R8 ; R7 is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl; R8 is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylthio and C3-C8-cycloalkyl; R9 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl; n is an integer selected from 0 to 2. In yet another embodiment, the present invention provides a compound of formula (I),
Figure imgf000023_0001
Formula (I) wherein, Z1 represents CHR2 and Z2 represents N-R3; R1 is selected from the group consisting of CF3, CHF2 and CF2Cl; R2 is selected from the group consisting of hydrogen, halogen, cyano, nitro, thiol, amino, hydroxy, C1- C6-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6- alkoxy-C1-C6-alkyl; R3 is selected from the group consisting of C1-C6-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6- alkyl, C3-C8-halocycloalkyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl, C3-C8- heterocyclyl-C1-C6-alkyl, -(CHR9)n-C(=O)-R4, -C(=O)-(CHR9)n-R4, -C(=O)-(CHR9)n-O-R4, -C(=O)- (CHR9)n-S-R4, -C(=O)-(CHR9)n-N(R5)(R6), -(CHR9)n-(C=O)-C(=O)-R4, -(CHR9)n-C(=O)-O-R4, - (C=O)-C(=O)-O-R4, -(CHR9)n-C(=O)-(CHR9)n-N(R5)(R6), -(CHR9)n-(C=O)-C(=O)-N(R5)(R6), -S(O)2- R4, -(CHR9)n-N(R5)-C(=O)-R4, -(CHR9)n-N(R5)-C(=O)-O-R4, -(CHR9)n-C(=O)-N(R5)-S(=O)n-R4, - (CHR9)n-N(R5)-S(=O)n-R4 and -S(O)2-N(R5)(R6); wherein the aliphatic or cyclic moieties of R3 may optionally be substituted with one or more groups of R3a; R3a is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thio, amino, C1- C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C6-haloalkoxy, C1-C6- alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, phenyl, benzyl, and C3-C10-heterocyclyl; wherein each group of R3a may optionally be substituted with one or more groups selected from halogen, cyano, nitro, hydroxyl, thio, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6- alkoxy, C1-C4-alkoxy-C1-C4-alkyl or C1-C6-haloalkoxy; R4 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6 alkoxy-C1-C6-alkyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, C1-C6-dialkylamino, C3-C8-cycloalkylamino, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl and C3-C8- heterocyclyl-C1-C6-alkyl; each group of R4 may optionally be substituted with one or more groups R4a; R4a is selected from the group consisting of halogen, cyano, amino, C1-C6-alkylamino, C1-C6- dialkylamino, C1-C6-alkyl, C1-C6-alkylthio, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy and phenoxy; R5 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl; R6 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3- C8-heterocyclyl and C3-C8-heterocyclyl-C1-C6-alkyl; each group of R6 may optionally be substituted with one or more groups R6a; R6a may be optionally substituted with halogen, cyano, amino, C1-C6-alkylamino, C1-C6 dialkylamino, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkyl, C1-C6-alkylthio, C3-C6-cycloalkyl, C3-C6-cycloalkoxy and phenoxy; or R5 and R6 together with the atom to which they are attached may form a fused or non-fused 4-8 membered heterocyclic ring containing at least one heteroatom selected from O, S(=O)0-2, or NR7 and which may be optionally substituted with one or more groups R8 ; R7 is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl; R8 is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylthio and C3-C8-cycloalkyl; R9 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl; n is an integer selected from 0 to 2. In yet another preferred embodiment, n is an integer selected from 0 to 2. In yet another another preferred embodiment, n is an integer selected from 0 to 1. In one preferred embodiment, the present invention provides a compound of formula (I), wherein R1 is selected from the group consisting of CF3, CHF2 and CF2Cl; and the radicals R2, R3, R4, R5, R6, R7, R8, R9, Z1, Z2 and n have the same meanings as given for the compounds of formula (I) in the above detailed description. In another preferred embodiment, R2 is selected from the group consisting of hydrogen, halogen, cyano, nitro, thiol, amino, hydroxyl and C1-C6-alkyl; and the radicals R1, R3, R4, R5, R6, R7, R8, R9, Z1, Z2, m and n have the same meanings as given for the compounds of formula (I) in the above detailed description. In yet another preferred embodiment, the present invention provides a compound of formula (I), wherein R3 is selected from the group consisting of -(CHR9)n-C(=O)-R4, -C(=O)-(CHR9)n-R4, -C(=O)- (CHR9)n-O-R4, -C(=O)-(CHR9)n-S-R4, -C(=O)-(CHR9)n-N(R5)(R6), -(CHR9)n-(C=O)-C(=O)-R4, - (CHR9)n-C(=O)-O-R4, -(C=O)-C(=O)-O-R4, -(CHR9)n-C(=O)-(CHR9)n -N(R5)(R6), -(CHR9)n-(C=O)- C(=O)-N(R5)(R6), -S(O)2-R4, -(CHR9)n-N(R5)-C(=O)-R4, -(CHR9)n-N(R5)-C(=O)-O-R4, -(CHR9)n- C(=O)-N(R5)-S(=O)n-R4, -(CHR9)n-N(R5)-S(=O)n-R4, and -S(O)2-N(R5)(R6); and the radicals R1, R2, R4, R5, R6, R7, R8, R9, Z1, Z2, m and n have the same meanings as given for the compounds of formula (I) in the above detailed description. In yet another preferred embodiment, the present invention provides a compound of formula (I), wherein R3 is selected from the group consisting of -(CHR9)n-C(=O)-R4, -C(=O)-(CHR9)n-R4, -C(=O)- (CHR9)n-O-R4, -C(=O)-(CHR9)n-S-R4, -C(=O)-(CHR9)n-N(R5)(R6), -(CHR9)n-(C=O)-C(=O)-R4, - (CHR9)n-C(=O)-O-R4, -(C=O)-C(=O)-O-R4, -(CHR9)n-C(=O)-(CHR9)n -N(R5)(R6), -(CHR9)n-(C=O)- C(=O)-N(R5)(R6), -S(O)2-R4 and -S(O)2-N(R5)(R6); and the radicals R1, R2, R4, R5, R6, R7, R8, R9, Z1, Z2, m and n have the same meanings as given for the compounds of formula (I) in the above detailed description. In yet another preferred embodiment, the present invention provides a compound of formula (I), wherein R4 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6 alkoxy-C1-C6-alkyl, C3-C8-cycloalkylamino, C6- C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl and C3-C8-heterocyclyl-C1-C6-alkyl; each group of R4 may optionally be substituted with one or more groups R4a selected from the group consisting of halogen, cyano, amino, C1-C6-alkylamino, C1-C6-dialkylamino, C1-C6-alkyl, C1-C6-alkylthio, C1-C6- alkoxy, C1-C6-haloalkyl and C3-C6-cycloalkyl; and the radicals R1, R2, R3, R5, R6, R7, R8, R9, Z1, Z2, m and n have the same meanings as given for the compounds of formula (I) in the above detailed description. In yet another preferred embodiment, the present invention provides a compound of formula (I), wherein R5 is selected from the group consisting of hydrogen or C1-C6-alkyl; and the radicals R1, R2, R3, R4, R6, R7, R8, R9, Z1, Z2 and n have the same meanings as given for the compounds of formula (I) in the above detailed description. In yet another preferred embodiment, the present invention provides a compound of formula (I), wherein R6 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6- cycloalkyl-C1-C6-alkyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl and C3-C8- heterocyclyl-C1-C6-alkyl; each group of R6 may optionally be substituted with one or more groups R6a; and the radicals R1, R2, R3, R4, R5, R7, R8, R9, Z1, Z2, m and n have the same meanings as given for the compounds of formula (I) in the above detailed description. In yet another preferred embodiment, the present invention provides a compound of formula (I), wherein R6a may be optionally substituted with halogen, cyano, amino, C1-C6-alkylamino, C1-C6 dialkylamino, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkyl , C1-C6-alkylthio and C3- C6-cycloalkyl; and the radicals R1, R2, R3, R4, R5, R6, R7, R8, R9, Z1, Z2, m and n have the same meanings as given for the compounds of formula (I) in the above detailed description. In yet another preferred embodiment, the present invention provides a compound of formula (I), wherein R5 and R6 together with the atom to which they are attached may form a fused or non-fused 4- 8 membered heterocyclic ring containing at least one heteroatom selected from O, S(=O)0-2, or NR7 and which may be optionally substituted with one or more groups R8; and the radicals R1, R2, R3, R4, R7, R8, R9, Z1, Z2, m and n have the same meanings as given for the compounds of formula (I) in the above detailed description. In yet another preferred embodiment, the present invention provides a compound of formula (I), wherein R8 is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C1- C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-alkylthio; and the radicals R1, R2, R3, R4, R5, R6, R7, R9, Z1, Z2, m and n have the same meanings as given for the compounds of formula (I) in the above detailed description. In yet another preferred embodiment, the present invention provides a compound of formula (I), wherein R9 is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl; and the radicals R1, R2, R3, R4, R5, R6, R7, R8, Z1, Z2, m and n have the same meanings as given for the compounds of formula (I) in the above detailed description. In a preferred embodiment, the compound of formula (I) is selected from (4-methoxyphenyl)(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, (3- methoxyphenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)methanone, p-tolyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)methanone, pyridin-3-yl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)methanone, (4-chlorophenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, (2,4-difluorophenyl)(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 2-(4-methoxyphenyl)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(4- chlorophenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)ethan-1-one, cyclobutyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)methanone, cyclopropyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, (1-methyl-1H-pyrazol-3-yl)(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, (2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)(4- (trifluoromethyl)phenyl)methanone, (4-fluorophenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, phenyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-methyl-1-(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan-1-one, 3-methyl-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)butan-1-one, 4-(2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-5- carbonyl)benzonitrile, (2-fluorophenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 2-phenyl-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, (1-methyl-1H-pyrazol-4-yl)(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, ethyl 2- oxo-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate, N,N-dimethyl-2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)acetamide, N-ethyl-2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-methyl-2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(cyclopropylmethyl)-2-oxo- 2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, 3-(5-((4-chlorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-5-(trifluoromethyl)- 1,2,4-oxadiazole, 5-(trifluoromethyl)-3-(5-((4-(trifluoromethyl)phenyl)sulfonyl)-4,5,6,7- tetrahydrothieno[3,2-c]pyridin-2-yl)-1,2,4-oxadiazole, 3-(5-tosyl-4,5,6,7-tetrahydrothieno[3,2- c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(5-((2,4-difluorophenyl)sulfonyl)-4,5,6,7- tetrahydrothieno[3,2-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(5-(phenylsulfonyl)- 4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(5- (methylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 5- (trifluoromethyl)-3-(5-((3-(trifluoromethyl)phenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2- yl)-1,2,4-oxadiazole, 3-(5-((3-chlorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole, 3-(5-((4-fluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2- c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(5-((2-fluorophenyl)sulfonyl)-4,5,6,7- tetrahydrothieno[3,2-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(5-((2-chloro-4- fluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole, 5-(trifluoromethyl)-3-(5-((trifluoromethyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2- c]pyridin-2-yl)-1,2,4-oxadiazole, 3-(5-(cyclopropylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2- yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(5-(propylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2- c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(5-((3-fluorophenyl)sulfonyl)-4,5,6,7- tetrahydrothieno[3,2-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 2-(2-chlorophenoxy)-1-(2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 3- (5-((2-chloro-6-methylphenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole, 2-((6-fluoropyridin-3-yl)oxy)-1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(4-fluorophenoxy)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 1-(2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan-1-one, 2,2-dimethyl-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)propan-1-one, 1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)butan-1-one, (3-fluorophenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, m-tolyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 2-phenyl-1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan-1-one, 2-(3,4-difluorophenyl)-1-(2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2- (m-tolyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)ethan-1-one, thiazol-4-yl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)methanone, pyrimidin-5-yl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 2-(4-chlorophenyl)-1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan-1-one, (3-chlorophenyl)(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, N-(4- chlorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxamide, N-phenyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxamide, N-(4-methoxyphenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(2,3-difluorophenyl)-2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(3,5-difluorophenyl)- 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N- cyclopentyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxamide, N-cyclobutyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxamide, N-(cyclopropylmethyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(tert-butyl)-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-isopropyl-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(p- tolyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxamide, N-(4-fluorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxamide, N-(2-chlorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(3-methoxyphenyl)-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(3-chlorophenyl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(3- fluorobenzyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxamide, N-(4-fluorobenzyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxamide, N-(3-fluorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(2,2,2-trifluoroethyl)-2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-cyclopropyl-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(3,5- dimethylisoxazol-4-yl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine- 5(4H)-carboxamide, N-(2,6-diisopropylphenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-N- (1,3,5-trimethyl-1H-pyrazol-4-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(2- fluorobenzyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxamide, N-ethyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine- 5(4H)-carboxamide, N-(4-fluoro-2-methylphenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(tetrahydro-2H-pyran-4-yl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N- benzyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxamide, N-(2-chlorobenzyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxamide, ethyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate, N-(3,5-dichlorophenyl)-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(pyridin-3-yl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(2,4- difluorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxamide, 2-(4-chlorophenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(4-chloro-2-fluorophenoxy)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(2- fluoro-4-methylphenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one, 2-(2,4-difluorophenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(2-fluorophenoxy)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(2- fluorophenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)ethan-1-one, 2-(2-chloro-4-fluorophenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(2-methoxy-4-methylphenoxy)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(4- (methylthio)phenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one, 2-(o-tolyloxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(4-chloro-2-methylphenoxy)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(3- fluorophenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)ethan-1-one, 2-(3-chlorophenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(p-tolyloxy)-1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(3- (dimethylamino)phenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one, 2-(3-methoxyphenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(3,5-dichlorophenoxy)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(2- chloro-6-fluorophenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one, 2-(4-fluoro-2-methylphenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-((1-methyl-1H-pyrazol-3- yl)oxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)ethan-1-one, 4-methoxyphenyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxylate, p-tolyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate, isobutyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate, methyl 2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate, 4-chlorophenyl 2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate, (3- chlorophenyl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)methanone, (3-fluorophenyl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)methanone, (2-fluorophenyl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, p-tolyl(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan-1-one, phenyl(3-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, o-tolyl(3-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, (4-(tert-butyl)phenyl)(3- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, (3- methoxycyclobutyl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)methanone, 3-methyl-1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)butan-1-one, (4-fluorophenyl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)-2-(4-(trifluoromethyl)phenyl)ethan-1-one, 2-(4-fluorophenyl)- 1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1- one, 2-(5-fluoropyridin-3-yl)-1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one, 2-phenyl-1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(2-chlorophenyl)-1-(3-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, (3,5- bis(trifluoromethyl)phenyl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)methanone, 2-(4-chlorophenyl)-1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-phenyl-1-(3-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan-1-one, cyclobutyl(3-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, (1- methyl-1H-pyrazol-3-yl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)methanone, 2-(thiazol-4-yl)-1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(pyrimidin-5-yl)-1-(3-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(3-chlorophenyl)-1-(3-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan-1-one, 2-(4- methoxyphenyl)-1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)propan-1-one, 1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one, 2-(4-fluorophenyl)-1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan-1-one, 3-(5-(phenylsulfonyl)-4,5,6,7- tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(5-((4-chloro-2- methylphenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole, N-(2,6-dichlorophenyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(4-chlorophenyl)-3-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(2-chloro-6-fluorophenyl)- 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, 2- (3-fluorophenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)ethan-1-one, 2-methoxy-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan-1-one, pyridin-4-yl(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 2-(p-tolyl)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, (tetrahydrofuran-3-yl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)methanone, 2-(3,4-dichlorophenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(2-fluorophenyl)-1-(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, oxazol-4-yl(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, isoxazol-3-yl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)methanone, 2-(o-tolyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one, 2-(2-chlorophenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(pyrazin-2-yl)-1-(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, o-tolyl(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, pyridin- 2-yl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)methanone, (1-methyl-1H-pyrazol-5-yl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 3-methoxy-1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan-1-one, (3-chloro-4-fluorophenyl)(2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 2-(4- fluorophenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)ethan-1-one, (3-chloro-4-methoxyphenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, (2-chloro-5-methoxyphenyl)(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-2-(4- (trifluoromethyl)phenyl)ethan-1-one, 2-(3,4-dimethylphenyl)-1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, (3,3-difluorocyclopentyl)(2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 2-(2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-5- carbonyl)benzonitrile, 3,3-dimethyl-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)butan-1-one, (4-(difluoromethyl)phenyl)(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 2-(4-bromophenyl)-1-(2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2- (4-chloro-2-fluorophenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one, 2-(2,4-dichlorophenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(2,4-difluorophenyl)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(1- methyl-1H-pyrazol-4-yl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one, oxetan-3-yl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 2-morpholino-1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(piperidin-1-yl)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, N-(3- fluorophenyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)acetamide, N-phenyl-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)acetamide, N-(p-tolyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(2-methoxyphenyl)-2-(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(5-methylthiazol-2-yl)- 2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-isopropyl-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)acetamide, N-(pyrimidin-5-yl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(2-fluorophenyl)-2-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(1-methyl-1H-pyrazol-4-yl)- 2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-cyclopentyl-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)acetamide, N-(4-fluorophenyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(pyridin-3-yl)-2-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(3-chlorophenyl)-2-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(2- chlorophenyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)acetamide, 2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)-N-(4-(trifluoromethyl)phenyl)acetamide, N-(4-chlorophenyl)-N-methyl-2-(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(3,4-dichlorophenyl)-2- (2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N- (2-chloro-6-fluorophenyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)acetamide, N-(2,4-difluorophenyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(4-chlorophenyl)-2-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N- propyl-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)acetamide, N-(3-methoxyphenyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(4-fluorophenyl)-N-methyl-2-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, 2- (isopropylamino)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)ethan-1-one, N-(4-fluorobenzyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-cyclobutyl-2-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(4-methylbenzyl)-2-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N- benzyl-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)acetamide, 2-((2-chloropyridin-3-yl)oxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-((2-methoxypyrimidin-5-yl)oxy)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-((5- methoxypyridin-3-yl)oxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one, 2-((5-fluoropyridin-3-yl)oxy)-1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 5-(2-oxo-2-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)ethoxy)nicotinonitrile, 2-((5-chloropyridin-3-yl)oxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-((4-fluorophenyl)thio)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2- (thiazol-2-ylthio)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)ethan-1-one, 2-((4-chlorophenyl)thio)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(phenylthio)-1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, cyclopentyl 2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate, propyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate, 2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-N-(4-(trifluoromethyl)phenyl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxamide, 2-chlorophenyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate, N-(2,6-dichlorophenyl)-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(2-chloro-6-fluorophenyl)- 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, 2- (2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetic acid, 3- (5-((4-chlorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole, 5-(trifluoromethyl)-3-(5-((4-(trifluoromethyl)phenyl)sulfonyl)-4,5,6,7- tetrahydrothieno[3,2-c]pyridin-3-yl)-1,2,4-oxadiazole, 3-(5-tosyl-4,5,6,7-tetrahydrothieno[3,2- c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(5-((2,4-difluorophenyl)sulfonyl)-4,5,6,7- tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(5-((4- fluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole, 3-(5-((2-fluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole, 3-(5-((3-fluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2- c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 5-(trifluoromethyl)-3-(5-((3- (trifluoromethyl)phenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-1,2,4-oxadiazole, 3-(5- (propylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3- (5-(cyclopropylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole, N-(3-chlorophenyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxamide, (3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)(4-(trifluoromethyl)phenyl)methanone, (4-chlorophenyl)(3-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 2-((1-methyl-1H-pyrazol- 4-yl)amino)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)ethan-1-one, 2-(cyclopentylamino)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(p-tolylamino)-1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, N-((4-fluorophenyl)sulfonyl)- 2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-propyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)- carboxamide, N-cyclobutyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxamide, N-ethyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-cyclopentyl-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-phenyl-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N- methyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)- carboxamide, N-isobutyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxamide, N-(tetrahydro-2H-pyran-4-yl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(3-methoxycyclobutyl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(4- chlorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)- carboxamide, N-(4-(trifluoromethoxy)phenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(4-fluorophenyl)-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(pyrimidin-5-yl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N- (pyridin-3-yl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)- carboxamide, N-(2-fluorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxamide, N-(2,4-difluorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(2-chlorophenyl)-2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(p-tolyl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(3- (difluoromethyl)phenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxamide, N-(thiazol-4-yl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(4-chlorobenzyl)-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(thiazol-2-yl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(1- phenylethyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)- carboxamide, 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-N-(4-(trifluoromethyl)phenyl)-4,7- dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(3,4-dichlorophenyl)-2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(4- (difluoromethyl)phenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxamide, N-(2,6-dichlorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(4-methylbenzyl)-2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(4-fluorobenzyl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N- (pyridin-3-ylmethyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine- 6(5H)-carboxamide, N-(isoxazol-4-yl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(4-methoxybenzyl)-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(1-methyl-1H-pyrazol-4-yl)- 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N- benzyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)- carboxamide, N-(3-fluorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxamide, N,N-diethyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N,N-dimethyl-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, morpholino(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, pyrrolidin-1-yl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)- yl)methanone, (4-methoxyphenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, (4-chlorophenyl)(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, p-tolyl(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, (4-fluorophenyl)(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, (2,4- difluorophenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)- yl)methanone, (2-fluorophenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridin-6(5H)-yl)methanone, o-tolyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, (2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridin-6(5H)-yl)(2-(trifluoromethyl)phenyl)methanone, phenyl(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, (4- (trifluoromethoxy)phenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridin-6(5H)-yl)methanone, (2,4-dimethylphenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, pyridin-4-yl(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, pyridin-3-yl(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, pyridin- 2-yl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)- yl)methanone, (2-fluoropyridin-4-yl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, pyrimidin-4-yl(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, 1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)ethan-1-one, cyclopropyl(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, cyclobutyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)- yl)methanone, 2,2,2-trifluoro-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridin-6(5H)-yl)ethan-1-one, (1-methyl-1H-pyrazol-4-yl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, 2-phenoxy-1-(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)ethan-1-one, 2-(4-fluorophenoxy)-1- (2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)ethan-1-one, 2-(phenylamino)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin- 6(5H)-yl)ethan-1-one, 2-((2-fluoropyridin-4-yl)oxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)ethan-1-one, 3-(6-(methylsulfonyl)-4,5,6,7- tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 5-(trifluoromethyl)-3-(6- ((trifluoromethyl)sulfonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-1,2,4-oxadiazole, 3-(6- (phenylsulfonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3- (6-((4-fluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole, 3-(6-tosyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole, 3-(6-((4-methoxyphenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole, 3-(6-((2,4-difluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[2,3- c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(6-((4-chlorophenyl)sulfonyl)-4,5,6,7- tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(6-((3- fluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole, 3-(6-(m-tolylsulfonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)- 1,2,4-oxadiazole, 3-(6-(cyclopropylsulfonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole, N-methyl-2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)acetamide, 2-oxo-N-phenyl-2-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)acetamide, N-(4-fluorophenyl)-2-oxo-2-(2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)acetamide, N-(3- fluorophenyl)-2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin- 6(5H)-yl)acetamide, N-(4-chlorophenyl)-2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridin-6(5H)-yl)acetamide, N-(cyclopropylmethyl)-2-oxo-2-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)acetamide, phenyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate, p- tolyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)- carboxylate, 4-fluorophenyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxylate, ethyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate, (7-methyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)(phenyl)methanone, (4-fluorophenyl)(7-methyl-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, (4- chlorophenyl)(7-methyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin- 6(5H)-yl)methanone, (4-methoxyphenyl)(7-methyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, (2,4-difluorophenyl)(7-methyl-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, cyclopropyl(7-methyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin- 6(5H)-yl)methanone, (7-methyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridin-6(5H)-yl)(pyridin-4-yl)methanone, 3-(7-methyl-6-(phenylsulfonyl)-4,5,6,7- tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(6-((4- fluorophenyl)sulfonyl)-7-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)- 1,2,4-oxadiazole, 3-(7-methyl-6-(methylsulfonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole, 3-(7-methyl-6-((trifluoromethyl)sulfonyl)-4,5,6,7- tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, N,7-dimethyl-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N- (cyclopropylmethyl)-7-methyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxamide or 7-methyl-N-phenyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide. The compounds of the present disclosure may be present either in pure form or as mixtures of different possible isomeric forms such as stereoisomers or constitutional isomers. The various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, and geometric isomers. Any desired mixtures of these isomers fall within the scope of the claims of the present disclosure. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other isomer(s) or when separated from the other isomer(s). Additionally, a person skilled in the art knows processes or methods or technologies to separate, enrich, and/or to selectively prepare said isomers. An anion part of the salt in case the compound of formula (I) is cationic or capable of forming a cation can be inorganic or organic. Alterntively, a cation part of the salt in case the compound of formula (I) is anionic or capable of forming an anion can be inorganic or organic. Examples of the inorganic anion part of the salt include but are not limited to chloride, bromide, iodide, fluoride, sulfate, phosphate, nitrate, nitrite, hydrogen carbonates or hydrogen sulfate. Examples of the organic anion part of the salt include but are not limited to formate, alkanoates, carbonates, acetates, trifluoroacetate, trichloroacetate, propionate, glycolate, thiocyanate, lactate, succinate, malate, citrates, benzoates, cinnamates, oxalates, alkylsulphates, alkylsulphonates, arylsulphonates aryldisulphonates, alkylphosphonates, arylphosphonates, aryldiphosphonates, p-toluenesulphonate, and salicylate. Examples of the inorganic cation part of the salt include but are not limited to alkali and alkaline earth metals. Examples of the organic cation part of the salt include but are not limited to pyridine, methyl amine, imidazole, benzimidazole, hitidine, phosphazene, tetramethyl ammonium, tetrabutylammonium, choline and trimethylamine. Metal ions in the metal complexes of the compound of formula (I) are especially the ions of the elements of the second main group, especially calcium and magnesium, of the third and fourth main groups, especially aluminium, tin and lead, and also of the first to eighth transition groups, especially chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Particular preference is given to the metal ions of the elements of the fourth period and the first to eighth transition groups. Here, the metals can be present in the various valencies that they can assume. The compound selected from formula (I), (including all stereoisomers, N-oxides, and salts thereof), may typically exist in more than one form. Formula (I) thus includes all crystalline and non- crystalline forms of the compounds that formula (I) represents. Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts. Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types). The term "polymorph" refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due to the presence or absence of co- crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability. One skilled in the art will appreciate that a polymorph of a compound represented by formula (I) can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound represented by formula (I). Preparation and isolation of a particular polymorph of a compound represented by formula (I) can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures. In one embodiment, the present invention provides a process for the preparing the compounds of formula (I). The following schemes illustrate approaches for preparing the compounds of formula (I). The following descriptions and examples are provided for illustrative purposes and should not be construed as limiting in terms of substituents or substitution patterns. Further, the mentioned reagents, solvents and reaction conditions are intended for the purpose of exemplification only and should not be construed as limiting. The compounds of the present invention as defined by formula (I) and/or in the tables 1 to 12 may be prepared, in a known manner, in a variety of ways as described in the schemes 1-4. The definitions of Z1, Z2, R1, R2, R3, R4, R5, R6, R7, R8 and R9 in the compounds of formula (I), ii, iii, iv, v and vi are as defined above in the detailed description of the invention unless otherwise stated specifically. General scheme: 1
Figure imgf000040_0001
The compounds of formula iii can be prepared by the cyanation of bromo compounds of formula ii. This reaction can be performed by using a cyanating agent as for instance potassium hexacyanoferrate(II)trihydrate in the presence of a as for instance catalyst XantPhos Pd(allyl)]Cl and a base as for instance potassium acetate. This reaction is typically carried out in the presence of a solvent, 1,4-dioxane, at a temperature ranging from 80 to 100 °C. Alternatively, this reaction can also be carried out by reacting compounds of formula ii with potassium ferrocyanide in the presence of a catalyst for instance dichloro[bis{1- (dicyclohexylphosphanyl)piperidine}]palladium in a solvent as for instance 1-methyl-pyrrolidin-2- one at a temperature of 140 ℃ as reported in the Chemistry - A European Journal, 2012, vol. 18, # 10, p.2978 – 2986. Step: 2
Figure imgf000040_0002
The compounds of formula iv can be obtained by reacting compounds of formula iii with hydroxyl amine in the presence of a suitable polar protic solvent such as ethanol, methanol and the like. Alternatively, this reaction can also be carried out by using hydroxylamine hydrochloride in the presence of a suitable organic or a suitable inorganic base such as triethylamine, N,N- diisopropylethylamine, sodium bicarbonate and the like. Step: 3
Figure imgf000041_0001
The compounds of formula v can be obtained by reacting compounds of formula iv and carboxylic acid anhydrides of formula (a). These reactions are typically carried out in the presence of a suitable aprotic solvent such as tetrahydrofuran, 1, 4-dioxane, dichloromethane, and the like, and optionally in the presence of a suitable base such as triethylamine, N, N-diisopropylethylamine, and the like at a temperature ranging from 0 to 50 °C. Step: 4
Figure imgf000041_0002
The compounds of formula vi can be obtained by deprotecting compounds of formula v under acidic conditions, for instance in the presence of 4 M hydrochloric acid in a solvent as in 1,4-dioxane. Other suitable solvent can be such as dichloromethane or tetrahydrofuran, the reaction as such being carried out at a temperature ranging from 0 to 30 °C. Step: 5
Figure imgf000041_0003
The compounds of formula (I) in which Z2 is CH2 and Z1 is N-R3 wherein R3 is -(CH2)n-C(=O)-R4 can be obtained by reacting the compounds of formula vi with compounds of 2f in the presence of a suitable base such as triethylamine or N,N-diisopropylethylamine and the like. This reaction is carried out in a suitable aprotic solvent such as dichloromethane, tetrahydrofuran and the like at a temperature ranging from 0 to 30 °C. Alternatively, the compounds of formula (I) in which Z2 is CH2 and Z1 is N-R3 wherein R3 is -(CH2)n- C(=O)-R4 can also be obtained by reacting compounds of formula vi with compounds of formula 2e in the presence of a suitable amide coupling reagent such as HATU ((1-[bis(dimethylamino)methylene]- 1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate), N-(3-dimethylaminopropyl)-N′- ethyl carbodiimide hydrochloride, 4-dimethylaminopyridine and the like. This reaction is carried out in the presence of a suitable base such as trimethylamine, N,N-diisopropylethylamine and the like, in the presence of a suitable solvent such as dichloromethane, dimethylformamide and the like, at a temperature ranging from 0 to 40 °C. General scheme: 2
Figure imgf000042_0001
The compounds of formula (I) wherein Z2 is CH2, Z1 is N-R3 wherein R3 is -(CH2)n-C(=O)-N(R5)(R6) and n is 1, can be obtained by reacting compounds of formula vi with isocyanates of formula 2g. This reaction can be carried out in the presence of a suitable base such as triethylamine, N,N- diisopropylethylamine and the like; in a suitable aprotic solvent such as tetrahydrofurane, dichloromethane and the like. This reaction is typically carried out at a temperature ranging from 0 to 40 °C. General scheme: 3
Figure imgf000042_0002
The compounds of formula (I) wherein Z2 is CH2, Z1 is N-R3 wherein R3 is-(CH2)n-C(=O)-O-R4, and n is 0, can be obtained by reacting compounds of formula vi with a chloroformates of formula 2h in the presence of a suitable base such as triethylamine, pyridine, N,N-diisopropylethylamine and the like and in the presence of a suitable aprotic solvent such as tetrahydrofurane, dichloromethane and the like. This reaction is typically carried out at a temperature ranging from 0 to 40 °C. General scheme: 4
Figure imgf000042_0003
The compounds of formula (I) wherein Z2 is CH2, Z1 is N-R3 wherein R3 is-(CH2)n-C(=O)-O-R4, and n is 0, can be obtained by reacting compounds of formula vi with a sulfonyl chlorides of formula 2i in the presence of a suitable base such as triethylamine, N,N-diisopropylethylamine and the like, and in the presence of a suitable aprotic solvent such as tetrahydrofurane, dichloromethane and the like. This reaction can be carried out at a temperarture ranging from 0 to 40 °C. In one embodiment, the present invention relates to an agrochemical composition comprising a compound of formula (I) or agriculturally acceptable salts, metal complexes, constitutional isomers, stereo-isomers, diastereoisomers, enantiomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, geometric isomers, or N-oxides thereof optionally with one or more additional active ingredients(s), and optionally together with an auxiliary such as an inert carrier or any other essential ingredient(s) such as surfactants, additives, solid diluents and liquid diluents. It is also possible to use the compounds of formula (I) as fungicides. The term “fungicide” as used herein means a compound that controls, modifies, or prevents the growth of phytopathogenic fungi. In one embodiment, the present invention provides a method for controlling or preventing phytopathogenic microorganisms, wherein the method comprises treating the fungi or the materials, plants, plant parts, locus thereof, soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of formula (I) or the combination or the composition. In another embodiment, the present invention provides a method for controlling or preventing infestations of plants by phytopathogenic microorganisms in agricultural crops and/or horticultural crops, wherein an effective amount of at least one compound of formula (I) or the combination or the composition thereof is applied to the plants, to parts thereof or to a locus thereof. In yet another embodiment, the present invention provides a method for controlling or preventing infestation of plants by phytopathogenic microorganisms in agricultural crops and/or horticultural crops wherein an effective amount of at least one compound of formula (I) or the combination or the composition thereof, is applied to the seeds of plants. The compounds of formula (I) and the compositions according to the invention, respectively, are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Some are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants. The compounds of formula (I) and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rape, sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines (table grapes, grape juice and grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, e. g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants. Particularly, the compounds of formula (I) and the compositions according to the invention are important in the control of phytopathogenic fungi on cereals (e. g. wheat, rye, barley, triticale, oats or rice), soybeans and on plant propagation material, such as seeds, and the crop material of soybeans. Accordingly, the present invention provides compositions comprising at least one compound of formula (I) and seed. The amount of the compound of formula (I) in the composition ranges from 0.1 g a.i. (gram per active ingredient) to 10 kg a.i. (kilogram per active ingredient) per 100 kg of seeds. In one embodiement, the present invention provides a seed comprising a compound of formula (I), wherein the amount of the compound of formula (I) is from 0.1 g to 1 kg per 100 kg of seed. Preferably, the compounds of formula (I) and compositions thereof, respectively are used for controlling a multitude of fungi on field crops, such as potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes. The term "plant propagation material" is to be understood to denote all the generative or reproductive parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts, twigs, flowers, and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring, using the compounds of formula (I) and compositions thereof. Preferably, the treatment of plant propagation materials with the compounds of formula (I), the combination and or the composition thereof, respectively, is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; on rice, corn, cotton and soybeans. The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf. http://cera-gmc.org/, see GM crop database therein). Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo-or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties. Plants that have been modified by breeding, mutagenesis or genetic engineering, e. g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides like dicamba or 2,4-D; bleacher herbicides such as hydroxylphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as the resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are e. g. described in Pest Managem. Sci. 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g. imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g. tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate-tolerant, Bayer CropScience, U.S.A.), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate-tolerant, BASF, Germany). Furthermore, plants capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus (Bacillus), by the use of recombinant DNA techniques are within the scope of the present invention. The Bacillus are particularly from Bacillus thuringiensis, such as δ- endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA- reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention, these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO02/015701). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP374753, WO93/007278, WO95/34656, EP427529, EP451878, WO03/18810 und WO03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above. These insecticidal proteins, contained in the genetically modified plants, impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the CrylAb toxin), YieldGard® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins), Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the CrylAc toxin), Bollgard® I (cotton cultivars producing the Cry1 Ac toxin), Bollgard® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf®(potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (e. g. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme). Furthermore, plants capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens by the use of recombinant DNA techniques are also within the scope of the present invention. Examples of such proteins are the so-called "pathogenesis-related proteins" (PR proteins, see, e. g. EP392225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against phytophthora infestans derived from the mexican wild potato solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above. Furthermore, plants capable to synthesize one or more proteins, by the use of recombinant DNA techniques, to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants are within the scope of the present invention. Furthermore, plants that contain a modified amount of substances of content or new substances of content, by the use of recombinant DNA techniques, to improve human or animal nutrition, e. g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape, DOW Agro Sciences, Canada) are also within the scope of the present invention. Furthermore, plants that contain a modified amount of substances of content or new substances of content, by the use of recombinant DNA techniques, to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato, BASF SE, Germany) are also within the scope of the present invention. The present invention also relates to a method for combating infestation of plants by phytopathogenic micro-organisms in agricultural crops and or horticultural crops wherein an effective amount of at least one compound of formula (I) or the combination of the present invention or the composition of the present invention, is applied to the seeds of plants. The compounds, the combinations and the compositions of the present invention can be used for combating plant diseases. The compounds of formula (I), the combinations and or the compositions thereof, respectively, are particularly suitable for controlling the following plant diseases: Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. Candida) and sunflowers (e. g. A. tragopogonis); Altemaria spp. (Alternaria leaf spot) on vegetables, rape (A. brassicola or brassicae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. solani or A. alternata), tomatoes (e. g. A. solani or A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A. tritici (anthracnose) on wheat and A. hordei on barley; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (D. maydis) or Northern leaf blight (B. zeicola) on corn, e. g. spot blotch (C. sorokiniana) on cereals and e. g. B. oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (e. g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: grey mold) on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spots) on corn (e. g. Gray leaf spot: C. zeae-maydis), rice, sugar beets (e. g. C. beticola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchii) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum: leaf mold) and cereals, e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph: Helminthosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e. g. C. sativus, anamorph: B. sorokiniana) and rice (e. g. C. miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) on cotton (e. g. C. gossypii), corn (e. g. C. graminicola: Anthracnose stalk rot), soft fruits, potatoes (e. g. C. coccodes: black dot), beans (e. g. C. lindemuthianum) and soybeans (e. g. C. truncatum or C. gloeosporioides); Corticium spp., e. g. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans and ornamentals; Cycloconium spp., e. g. C. oleaginum on olive trees; Cylindrocarpon spp. (e. g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e. g. C. liriodendri, teleomorph: Neonectria liriodendri: Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D. phaseolorum (damping off) on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis: tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (£. pyri), soft fruits (£. veneta: anthracnose) and vines (£. ampelina: anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beets (£. betae), vegetables (e. g. E. pisi), such as cucurbits (e. g. E. cichoracearum), cabbages, rape (e. g. E. cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e. g. E. turcicum); Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot) on various plants, such as F. graminearum or F. culmorum (root rot, scab or head blight) on cereals (e. g. wheat or barley), F. oxysporum on tomatoes, F. solani (f. sp. glycines now syn. F. virguliforme) and F. tucumaniae and F. brasiliense each causing sudden death syndrome on soybeans, and F. verticillioides on corn; Gaeumannomyces graminis (take-all) on cereals (e. g. wheat or barley) and corn; Gibberella spp. on cereals (e. g. G. zeae) and rice (e. g. G. fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G. gossypii on cotton; Grainstaining complex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G. sabinae (rust) on pears; Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals and rice; Hemileia spp., e. g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseoli) (root and stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e. g. P. brassicae), rape (e. g. P. parasitica), onions (e. g. P. destructor), tobacco (P. tabacina) and soybeans (e. g. P. manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp. e. g. on vines (e. g. P. tracheiphila and P. tetraspora) and soybeans (e. g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e. g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e. g. P. capsici), soybeans (e. g. P. megasperma, syn. P. sojae), soybeans, potatoes and tomatoes (e. g. P. infestans: late blight) and broad-leaved trees (e. g. P. ramorum: sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants; Plasmopara spp., e. g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers; Podosphaera spp. (powdery mildew) on rosaceous plants, hop, pome and soft fruits, e. g. P. leucotricha on apples; Polymyxa spp., e. g. on cereals, such as barley and wheat (P. graminis) and sugar beets (P. betae) and thereby transmitted viral diseases; Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapesia yallundae) on cereals, e. g. wheat or barley; Pseudoperonospora (downy mildew) on various plants, e. g. P. cubensis on cucurbits or P. humili on hop; Pseudopezicula tracheiphila (red fire disease or .rotbrenner', anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various plants, e. g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye, P. kuehnii (orange rust) on sugar cane and P. asparagi on asparagus; Pyrenophora (anamorph: Drechslera) tritici-repentis (tan spot) on wheat or P. teres (net blotch) on barley; Pyricularia spp., e. g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum); Ramularia spp., e. g. R. collo-cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (Rhizoctonia spring blight) on wheat or barley; Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporium secalis (scald) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soybeans (e. g. S. rolfsii or S. sclerotiorum); Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum (Stagonospora blotch) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on vines; Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e. g. S. reiliana: head smut), sorghum und sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni (plum pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e. g. T. basicola (syn. Chalara elegans); Tilletia spp. (common bunt or stinking smut) on cereals, such as e. g. T. tritici (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Typhula incarnata (grey snow mold) on barley or wheat; Urocystis spp., e. g. U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables, such as beans (e. g. U. appendiculatus, syn. U. phaseoli) and sugar beets (e. g. U. betae); Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae), corn (e. g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab) on apples (e. g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e. g. V. dahliae on strawberries, rape, potatoes and tomatoes. The compounds of formula (I), the combinations or the compositions thereof may be used to treat several fungal pathogens. Non-limiting examples of pathogens of fungal diseases which can be treated in accordance with the invention include: Ustilaginales such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae, rusts for example those caused by Pucciniales such as Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, Puccinia graminis, Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f.sp. Hordei, Puccinia striiformis f.sp. Secalis, Pucciniastrum coryli, or Uredinales such as Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor and Uromyces viciae-fabae; and other rots and diseases such as those caused by Cryptococcus spp., Exobasidium vexans, Marasmiellus inoderma, Mycena spp., Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, ltersonilia perplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctonia solani, Thanetephorus cucurmeris, Entyloma dahliae, Entylomella microspora, Neovossia moliniae and Tilletia caries. Blastocladiomycetes, such as Physoderma maydis. Mucoromycetes, such as Choanephora cucurbitarum; Mucor spp.; and Rhizopus arrhizus, In another embodiment diseases caused by rust pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae; Hemileia species, for example Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia species, for example Puccinia recondita, Puccinia graminis oder Puccinia striiformis; Uromyces species, for example Uromyces appendiculatus; In particular, Cronartium ribicola (White pine blister rust); Gymnosporangium juniperi-virginianae (Cedar-apple rust); Hemileia vastatrix (Coffee rust); Phakopsora meibomiae and P. pachyrhizi (Soybean rust); Puccinia coronata (Crown Rust of Oats and Ryegrass); Puccinia graminis (Stem rust of wheat and Kentucky bluegrass, or black rust of cereals); Puccinia hemerocallidis (Daylily rust); Puccinia persistens subsp. triticina (wheat rust or 'brown or red rust'); Puccinia sorghi (rust in corn); Puccinia striiformis ('Yellow rust' in cereals); Uromyces appendiculatus (rust of beans); Uromyces phaseoli (Bean rust); Puccinia melanocephala ('Brown rust' in sugarcane); Puccinia kuehnii ('Orange rust' in sugarcane). Plants which can be treated in accordance with the invention include the following: cotton, flax, grapevine, fruits, vegetables, such as Rosaceae sp (for example pome fruits such as apples, pears, apricots, cherries, almonds and peaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example banana trees and plantations), Rubiaceae sp. (for example coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example lemons, oranges and grapefruit); Vitaceae sp. (for example grapes); Solanaceae sp. (for example tomatoes, peppers), Liliaceae sp., Asteraceae sp. (for example lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), Alliaceae sp. (for example leek, onion), Papilionaceae sp. (for example peas); major crop plants, such as Poaceae/Gramineae sp. (for example maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), 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); Malvaceae (for example cotton); useful plants and ornamental plants for gardens and wooded areas; and genetically modified varieties of each of these plants. More preference is given to controlling the following diseases of soya beans: Fungal diseases on leaves, stems, pods and seeds caused, for example, by Altemaria leaf spot (Altemaria spec. atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines ), cercospora leaf spot and blight ( Cercospora kikuchii), choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina trifolii), phyllostica leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta glycines), rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsora meibomiae), scab (Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), target spot (Corynespora cassiicola). Fungal diseases on roots and the stem base caused, for example, by black root rot (Calonectiia crotalariae), charcoal rot (Macrophomina phaseolina), fusarium blight or wilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmospora vasinfecta), pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidennatum, 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 present invention also relates to the use of the compounds of formula (I), the combinations or the compositions thereof for combating the following plant diseases: Puccinia spp. (rusts) on various plants, for example, but not limited to P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye and Phakopsoraceae spp. on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans, Hemileia vastatrix (Coffee rust), Uromyces appendiculatus, Uromyces fabae and Uromyces phaseoli (rust of beans). The present invention also relates to the use of the compounds of formula (I), the combinations or the compositions thereof for combating the following plant diseases: Hemileia vastatrix (Coffee rust), Uromyces appendiculatus/fabae/ phaseoli (rust of beans) Puccinia spp. (rusts) on various plants selected from P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. Hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals selected from wheat, barley or rye and Phakopsora spp. on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans. The present invention further relates to the use of the compounds of formula (I), the combinations or the compositions thereof for combating against phytopathogenic fungi such as Phakopsora pachyrhizi, Phakopsora meibomiae, of agricultural crops and or horticultural crops. The compounds of formula (I), the combinations and the compositions thereof, respectively, are also suitable for the protection of harvest, stored products or materials against harmful fungi. The term "protection of materials" is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria. As to the protection of wood and other materials, the particular attention is paid to the following harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Pora spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Altemaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., and in addition in the protection of stored products and harvest the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae. In one embodiment the compounds of formula (I), the combinations and the compositions thereof, respectively, are particularly suitable for controlling the following plant diseases: Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans. The present invention further relates to a method for combating phytopathogenic fungi. The method comprises treating the fungi or the materials, plants, plant parts, locus thereof, soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of formula (I) or the combination or the composition comprising at least one compound of formula (I). The method of treatment according to the invention can also be used in the field of protecting stored products or harvest against the attack of fungi and microorganisms. According to the present invention, the term "stored products" is understood to denote natural substances of plant or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired. Stored products of crop plant origin, such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in the processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted, which process is also known as post-harvest treatment. Also falling under the definition of stored products is timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood. Stored products of animal origin are hides, leather, furs, hairs and the like. The combination according the present invention can prevent disadvantageous effects such as decay, discoloration or mold. Preferably "stored products" is understood to denote natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms. The compounds of formula (I), the combinations and the compositions thereof, respectively, may be used for improving the health of a plant. The invention also relates to a method for improving plant health by treating a plant, its propagation material and/or the locus where the plant is growing or is to grow with an effective amount of compound (I) and the composition thereof, respectively. The term "plant health" is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor (e. g. improved plant growth and/or greener leaves ("greening effect")), quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and/or biotic stress. The above identified indicators for the health condition of a plant may be interdependent or may result from each other. The compounds of formula (I) can be present in different crystal modifications or polymorphs whose biological activity may differ. They are likewise subject matter of the present invention. The compounds of formula (I) are applied as such or in the form of compositions for treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active ingredients. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi. Plant propagation materials may be treated with a compound of formula (I), the combination and the composition thereof protectively either at or before planting or transplanting. The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of formula (I). An agrochemical composition comprises a fungicidally effective amount of a compound of formula (I). The term "effective amount" denotes an amount of the composition or of the compound of formula (I), 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 formula (I) used. The compounds of formula (I), their -oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof can be converted into customary types of agrochemical compositions, e. g. into solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC), emulsions (e. g. EW, EO, ES, ME), 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. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e. g. GF). These and further composition types are defined in the "Catalogue of pesticide Formulation types and international coding system", Technical Monograph No.2, 6th Ed. May 2008, CropLife International. The compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New Developments in Crop Protection Product Formulation, Agrow Reports DS243, T&F Informa, London, 2005. Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders. Suitable solvents and liquid carriers in this context are for instance water and organic solvents, such as mineral oil fractions of medium to high boiling point, e. g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e. g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, e. g. cyclohexanone; esters, e. g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e. g. N-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof. Suitable solid carriers or fillers are for instance mineral earths, e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers, e. g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e. g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof. Suitable surfactants are surface-active compounds, for instance such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.). Suitable anionic surfactants are for instance alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl-and tridecylbenzenes, sulfonates of naphthalenes and alkyl naphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates. Suitable nonionic surfactants are for instance alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are for instance fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate. Suitable cationic surfactants are for instance quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are for instance block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are for instance polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyethylene amines. Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves, and which improve the biological performance of the compounds of formula (I) on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and Additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5. Suitable thickeners are for instance polysaccharides (e. g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates. Suitable bactericides are for instance bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones. Suitable anti-freezing agents are for instance ethylene glycol, propylene glycol, urea and glycerin. Suitable anti-foaming agents are for instance silicones, long chain alcohols, and salts of fatty acids. Suitable colorants (e. g. in red, blue, or green) are for instance pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e. g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e. g. alizarin-, azo- and phthalocyanine colorants). Suitable tackifiers or binders are for instance polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers. Examples for composition types and their preparation are: i) Water-soluble concentrates (SL, LS) 10-60 wt% of a compound of formula (I) and 5-15 wt% wetting agent (e. g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e. g. alcohols) ad 100 wt%. The active substance dissolves upon dilution with water. ii) Dispersible concentrates (DC) 5-25 wt% of a compound of formula (I) and 1-10 wt% dispersant (e. g. polyvinyl pyrrolidone) are dissolved in an organic solvent (e. g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion of the active substance. iii) Emulsifiable concentrates (EC) 15-70 wt% of a compound of formula (I) and 5-10 wt% emulsifier (e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion of the active substance. iv) Emulsions (EW, EO, ES) 5-40 wt% of a compound of formula (I) and 1-10 wt% emulsifier (e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a 20-40 wt% water-insoluble organic solvent (e. g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion of the active substance. v) Suspensions (SC, OD, FS) In an agitated ball mill, 20-60 wt% of a compound of formula (I) are comminuted with the addition of 2-10 wt% dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate), 0.1-2 wt% thickener (e. g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For a FS type composition up to 40 wt% binder (e. g. polyvinyl alcohol) is added. vi) Water-dispersible granules and water-soluble granules (WG, SG) 50-80 wt% of a compound of formula (I) are ground finely with the addition of dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance. vii) Water-dispersible powders and water-soluble powders (WP, SP, WS) 50-80 wt% of a compound of formula (I) are ground in a rotor-stator mill with the addition of 1-5 wt% dispersants (e. g. sodium lignosulfonate), 1-3 wt% wetting agents (e. g. alcohol ethoxylate) and a solid carrier (e. g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance. viii) Gels (GW, GF) In an agitated ball mill, 5-25 wt% of a compound of formula (I) are comminuted with the addition of 3-10 wt% dispersant (e. g. sodium lignosulfonate), 1-5 wt% thickener (e. g. carboxymethyl cellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance. ix) Microemulsions (ME) 5-20 wt% of a compound of formula (I) are added to a 5-30 wt% organic solvent blend (e. g. fatty acid dimethyl amide and cyclohexanone), 10-25 wt% surfactant blend (e. g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion of the active substance. x) Microcapsules (CS) An oil phase comprising 5-50 wt% of a compound of formula (I), 0-40 wt% of a water insoluble organic solvent (e. g. aromatic hydrocarbon) and 2-15 wt% of 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 results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound of formula (I) according to the invention, 0-40 wt% of a water insoluble organic solvent (e. g. aromatic hydrocarbon), and an isocyanate monomer (e. g. diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). The addition of a polyamine (e. g. hexamethylenediamine) results in the formation of polyurea microcapsules comprising the active substance. The monomers amount to 1-10 wt%. The wt% relates to the total CS composition. xi) Dustable powders (DP, DS) 1-10 wt% of a compound of formula (I) are ground finely and mixed intimately with a solid carrier (e. g. finely divided kaolin) ad 100 wt%. xii) Granules (GR, FG) 0.5-30 wt% of a compound of formula (I) are ground finely and associated with a solid carrier (e. g. silicate) ad 100 wt%. Granulation is achieved by extrusion, spray-drying or fluidized bed. xiii) Ultra-low volume liquids (UL) 1-50 wt% of a compound of formula (I) are dissolved in an organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%. The compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants. The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active ingredient (ai). The active ingredients (ai) are employed in a purity from 90% to 100%, preferably from 95% to 100% (according to the NMR spectrum). For the purposes of a treatment of plant propagation materials, particularly seeds, solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are usually employed. The compositions in question give, after two-to-tenfold dilution, active substance concentrations from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations. The application can be carried out before or during sowing. Methods for applying the compounds of formula (I), the combination and the composition thereof, respectively, are applications onto plant propagation material, especially seeds, including dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods. Preferably, the compounds of formula (I), the combination and the composition thereof, respectively, are applied on to the plant propagation material by a method such that the germination is not induced, e. g. by seed dressing, pelleting, coating and dusting. When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 1.0 kg per ha, and in particular from 0.1 to 1.0 kg per ha. In the treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seeds, the generally required amounts of the active substance are from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kg of plant propagation material (preferably seeds). When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are ranging from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg, of active substance per cubic meter of treated material. Various types of oils, wetters, adjuvants, fertilizers, or micronutrients, and further pesticides (e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides) may be added to the active substances or the compositions comprising them as a premix or, if appropriate, not until immediately prior to use, as a tank mix. These agents can be mixed with the composition according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:20 to 20:1. A pesticide is generally a chemical or biological agent (such as pesticidally active ingredient, compound, composition, virus, bacterium, antimicrobial or disinfectant) that through its effect deters, incapacitates, kills or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease or are vectors for disease. The term "pesticide" includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant defense activators that activate plant physiology for defense against certain pests; safeners that reduce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology e.g. to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant. The user applies compositions according to the invention usually from a predosage device, a Knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the respective agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is obtained by this procedure. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area. According to one embodiment, individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate. Consequently, one embodiment of the invention is a kit for preparing a usable pesticidal composition, the kit comprising a) a composition comprising component 1) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally a further active component 3) as defined herein. In one embodiment, the present invention provides a combination comprising a compound of formula (I) and at least one further pesticidally active substance selected from the group consisting of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertilizers and nutrients. The compounds of formula (I), the combinations and the compositions thereof comprising them in the use as fungicides with other fungicides may result in an expansion of the fungicidal spectrum of activity being obtained or in a prevention of fungicide resistance development. Furthermore, in many cases, extraordinary and unexpected effects are obtained. The present invention also relates to combinations comprising at least one compound of formula (I) as component (1) and at least one further pesticidally active substance as component (2), selected from the group of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertiliers and nutrients. The pesticidally active substances reported in WO2015185485 pages 36-43 and WO2017093019 pages 42-56 can be used in conjunction with the compounds of formula (I). The pesticidally active substances referred to as component (2), their preparation and their activity e. g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by the IUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP141317; EP152031; EP226917; EP243970; EP256503; EP428941 ; EP532022; EP1028125; EP1035122; EP1201648; EP1122244, JP2002316902; DE19650197; DE10021412; DE102005009458; US3296272; US3325503; WO9846608; WO9914187; WO9924413; WO9927783; WO0029404; WO0046148; WO0065913; WO0154501 ; WO 0156358; WO0222583; WO0240431; WO0310149; WO0311853; WO0314103; WO0316286; WO0353145; WO0361388; WO0366609; WO0374491; WO0449804; WO0483193; WO05120234; WO05123689; WO05123690; WO0563721; WO0587772; WO0587773; WO0615866; WO0687325; WO0687343; WO0782098; WO0790624; WO11028657; WO2012168188; WO2007006670; WO201177514; WO13047749; WO10069882; WO13047441; WO0316303; WO0990181; WO13007767; WO1310862; WO13127704; WO13024009; WO13024010; WO13047441; WO13162072; WO13092224 and WO11135833. The present invention furthermore relates to agrochemical mixtures comprising at least one compound of formula (I) (component 1) and at least one further active substance useful for plant protection. By applying the compounds of formula (I) together with at least one pesticidally active compound an additional effect can be obtained. This can be obtained by applying the compounds of formula (I) and at least one further pesticidally active substance simultaneously, either jointly (e. g. as tank-mix) or separately, or in succession, wherein the time interval between the individual applications is selected in such a way that it is ensured that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further pesticidally active substance(s). The order of application is not essential for the working of the present invention. When applying the compounds of formula (I) and a pesticidally active substance sequentially, the time between both applications may vary e. g. between 2 hours to 7 days. Also a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day. In the binary mixtures and the composition according to the invention the weight ratio of the component 1) and the component 2) generally depends on the properties of the active components used, usually it is in the range of 1:1000 to 1000:1, often in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1, even more preferably in the range of 1:4 to 4:1 and in particular in the range of 1:2 to 2:1. According to a further embodiment of the binary mixtures and the compositions thereof, the weight ratio of the component 1) and the component 2) usually is in the range of 1000:1 to 1:1000, often in the range of 100:1 to 1:100, regularly in the range of 50:1 to 1:50, preferably in the range of 20:1 to 1:20, more preferably in the range of 10:1 to 1:10, even more preferably in the range of 4:1 to 1:4 and in particular in the range of 2:1 to 1:2. In the ternary mixtures, i.e. the composition according to the invention comprising the component 1) and component 2) and a compound III (component 3), the weight ratio of component 1) and component 2) depends from the properties of the active substances used, usually it is in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1 and in particular in the range of 1:4 to 4:1 and 1:2 to 2:1, and the weight ratio of component 1) and component 3) usually it is in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1 and in particular in the range of 1:4 to 4:1 and 1:2 to 2:1. Any further active components are, if desired, added in a ratio of 20:1 to 1:20 to the component 1). These ratios are also suitable for the preparation of inventive mixtures applied by seed treatment. The invention disclosed in the present disclosure shall now be elaborated with the help of non-limiting examples. CHEMISTRY EXAMPLES: Example 1: Preparation of phenyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone (Compound no.14) a) Step 1: tert-butyl 6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate To a stirred solution of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (1 g, 5.7 mmol) in dichloromethane (12 mL) and methanol (3 mL), triethylamine (1.6 mL, 11.4 mmol) and di-tert-butyl dicarbonate (1.57 mL, 6.8 mmol) were added slowly at 0 °C. The resulting reaction mixture was stirred at 25 °C for 12 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain a crude product. The crude product was dissolved in dichloromethane (30 mL) and washed with water (90 mL). The dichloromethane layer was dried over anhydrous sodium sulfate and the volatiles were removed under reduced pressure to obtain tert-butyl 6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (1.35 g, 99 % yield). b) Step 2: tert-butyl 2-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate To a stirred solution of tert-butyl 6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (7.5 g, 31.3 mmol) in acetonitrile (75 mL), N-bromosuccinimide (6.14 g, 34.5 mmol) was added. The resulting reaction mixture was stirred at 25 °C for 3 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (75 mL) and washed with water (3 x 30 mL). The combined ethyl acetate layers were concentrated under reduced pressure to obtain tert-butyl 2-bromo-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (9.9 g, 99 % yield). c) Step 3: tert-butyl 2-cyano-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate To a stirred solution of tert-butyl 2-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (9.54 g, 30 mmol) in a mixture of 1,4-dioxane (65 mL) and water (25.8 mL), XantPhos Pd(allyl)]Cl (1.09 g, 1.5 mmol) and potassium acetate (1.471 g, 14.99 mmol) were added, followed by the addition of potassium hexacyanoferrate(II)trihydrate (6.96 g, 16.5 mmol) at 25 °C. The resulting reaction mixture was degassed with nitrogen for 20 min at 25 °C and the reaction mixture was further stirred at 100 °C for 7 h. After completion of the reaction, the reaction mixture was filtered and the filtrate was diluted with ethyl acetate (120 mL) and washed with water (4 x 40 mL). The combined ethyl acetate layers were concentrated under reduced pressure to obtain tert-butyl 2-cyano-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxylate (7.9 g, 99 % yield). d) Step 4: tert-butyl 2-(N'-hydroxycarbamimidoyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxylate To a stirred solution of tert-butyl 2-cyano-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (10.2 g, 38.6 mmol) in ethanol (100 mL), 50 % aqueous solution of hydroxylamine (8.04 mL, 69.5 mmol) was added at 0 °C. The resulting reaction mixture was stirred at 25 °C for 7 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain a crude product. The crude product was co-evaporated with ethyl acetate (30 mL) under reduced pressure to obtain tert- butyl 2-(N'-hydroxycarbamimidoyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (10.4 g, 91 % yield). e) Step 5: tert-butyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxylate To a stirred solution of tert-butyl 2-(N'-hydroxycarbamimidoyl)-6,7-dihydrothieno[3,2-c]pyridine- 5(4H)-carboxylate (10.1 g, 34 mmol) in tetrahydrofuran (7 mL), trifluoroacetic anhydride (8.16 mL, 57.7 mmol) was added at 0 °C. The resulting reaction mixture was stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (75 mL) and washed with an aqueous saturated sodium bicarbonate solution (3 x 30 mL). The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography to obtain tert-butyl 2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (10 g, 78 % yield). f) Step 6: 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5- ium chloride To a stirred solution of tert-butyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxylate (6.8 g, 18.12 mmol) in dichloromethane (68 mL), hydrogen chloride (4M in 1,4-dioxane) (31.7 mL, 127 mmol) was added slowly at 0 °C. The resulting reaction mixture was stirred at 25 °C for 8 h. After completion of the reaction, the reaction mixture was evaporated to dryness under reduced pressure to obtain a crude product. The crude product was co-evaporated with toluene (2 x 50 mL) under reduced pressure to obtain 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-ium chloride (5.59 g, 99 % yield). g) Step 7: phenyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)methanone (Compound no.14) To a stirred solution of benzoic acid (98 mg, 0.8 mmol) in dichloromethane (10 mL) and 1-ethyl-3-(3- dimethylaminopropyl)carbodiimide hydrochloride (308 mg, 1.6 mmol), 4-(dimethylamino)pyridine (294 mg, 2.4 mmol) was added at 0 °C and stirred for 30 min. To this reaction mixture, 2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-ium chloride (250 mg, 0.8 mmol) was added at 0 °C and the resulting reaction mixture was further stirred at 25 °C for 8 h. After completion of the reaction, the reaction mixture was diluted with dichloromethane (45 mL) and washed with water (3 x 30 mL). The dichloromethane layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography to obtain phenyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone (224 mg, 74 % yield). 1H-NMR (400 M, DMSO-d6) δ 7.85-7.67 (m, 1H), 7.48-7.47 (m, 5H), 4.74-4.56 (m, 2H), 3.97-3.63 (m, 2H), 2.98 (s, 2H); LCMS (M+H): 379.85. The following compounds in Table 1 were prepared by using analogous procedures as described in Example 1. Table: 1
Figure imgf000064_0001
Figure imgf000065_0001
Figure imgf000066_0001
Figure imgf000067_0001
Figure imgf000068_0001
Figure imgf000069_0001
Figure imgf000070_0001
Figure imgf000071_0001
Figure imgf000072_0001
Figure imgf000073_0001
Example 2: Preparation of N-methyl-2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide (Compound no.25) a) Step 1: ethyl 2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)acetate (Compound no.22) To a stirred solution of 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,5,6,7-tetrahydrothieno[3,2- c]pyridin-5-ium chloride (5.5 g, 17.6 mmol) in dichloromethane (20 mL), triethylamine (12.30 mL, 88 mmol) was added followed by the addition of ethyl 2-chloro-2-oxoacetate (4.02 mL, 35.3 mmol) at 0 oC. The resulting reaction mixture was stirred at 25 °C for 8 h. After completion of the reaction, the reaction mixture was diluted with dichloromethane (150 mL) and washed with water (3 x 60 mL). The combined dichloromethane layers were washed with brine solution (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography to obtain ethyl 2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate (5.25 g, 79 % yield). 1H-NMR (400 M, DMSO-d6) δ 7.81-7.77 (s, 1H), 4.65-4.57 (m, 2H), 4.36-4.28 (m, 2H), 3.88-3.70 (m, 2H), 3.-2.95 (m, 2H), 1.31-1.25 (m, 3H); LCMS (M-H): 373.85. b) Step 2: N-methyl-2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide (Compound no.25) To a stirred solution of methylamine hydrochloride (49.7 mg, 1.6 mmol) in toluene (10 mL), trimethylaluminium (2 M in toluene) (1.2 mL, 2.4 mmol) was added at 0 °C and stirred for 10 min at 0 °C. To this reaction mixture, ethyl 2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate (300 mg, 0.8 mmol) was added and the resulting reaction mixture was further stirred at 25 °C for 30 min. After completion of the reaction, the reaction mixture was quenched by the addition of 10 % aqueous acetic acid (20 mL) and extracted with ethyl acetate (3 x 15 mL). The combined ethyl acetate layers were washed with water (3 x 15 mL). The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography to obtain N- methyl-2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)acetamide (152 mg, 53% yield). 1H-NMR (400 M, DMSO-d6) δ 8.68-8.64 (m, 1H), 7.81-7.78 (s, 1H), 4.67-4.63 (m, 2H), 3.85-3.77 (m, 2H), 2.99-2.92 (m, 2H), 2.69-2.66 (s, 3H); LCMS (M+H): 360.50. The following compounds in Table 2 were prepared by using analogous procedures as described in Example 2. Table: 2
Figure imgf000074_0001
Example 3: Preparation of 3-(5-((4-chlorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2- c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole (Compound no.27) To a stirred suspension of 3-(4,5,6,7-tetrahydro-5l4-thieno[3,2-c]pyridin-2-yl)-5-(trifluoromethyl)- 1,2,4-oxadiazole hydrochloride (0.2 g, 0.64 mmol) in dichloromethane (10 mL), triethylamine (0.18 mL, 1.3 mmol) was added. The reaction mixture was cooled to 0 °C followed by the addition of 4- chlorobenzenesulfonyl chloride (0.15 g, 0.7 mmol). The resulting reaction mixture was further stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted with dichloromethane (3 x 20 mL). The combined dichloromethane layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain a crude product. The crude product was purified by flash column chromatography to obtain 3-(5-((4- chlorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole (0.21 g, 73 % yield). 1H-NMR (400 MHz, DMSO-D6) δ 7.84-7.78 (m, 2H), 7.71-7.68 (m, 3H), 4.27 (s, 2H), 3.46 (t, 2H), 2.93 (t, 2H); LCMS (M-H): 447.85. The following compounds in Table 3 were prepared by using analogous procedures as described in Example 3. Table: 3
Figure imgf000075_0001
Figure imgf000076_0001
Figure imgf000077_0001
Example 4: Preparation of N-(4-chlorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide (Compound no.58) To a solution of 3-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole (200 mg, 0.73 mmol) in dichloromethane (2 mL), triethylamine(0.3 mL, 2.2 mmol) was added. The reaction mixture was cooled to 0 °C followed by the addition of 1-chloro-4-isocyanatobenzene (134 mg, 0.9 mmol). The resulting reaction mixture was further stirred at 25 °C for 12 h. After completion of the reaction, the volatiles were removed under reduced pressure to obtain a crude product. The crude product was purified by column chromatoraphy to obtain N-(4-chlorophenyl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide (130 mg, 42 % yield). 1H-NMR (400 MHz, CHLOROFORM-D) δ 7.58 (s, 1H), 7.34-7.29 (m, 2H), 7.27 (d, 1H), 7.25-7.24 (m, 1H), 6.51 (s, 1H), 4.60 (d, 2H), 3.87-3.83 (m, 2H), 3.01 (t, 2H): LCMS (M+H): 429.15. The following compounds in Table 4 were prepared by using analogous procedures as described in Example 4. Table: 4
Figure imgf000077_0002
Figure imgf000078_0001
Figure imgf000079_0001
Figure imgf000080_0001
Figure imgf000081_0001
Figure imgf000082_0001
Example 5: Preparation of 4-methoxyphenyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (Compound no.111) To a stirred solution of 3-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole (0.2 g, 0.7 mmol) in dichloromethane, triethylamine (0.3 mL, 2.2 mmol) was added at 25 °C. The reaction mixture was cooled to 0 °C followed by the addition of 4-methoxyphenyl carbonochloridate (0.54 g, 2.9 mmol). The resulting reaction mixture was further stirred at 25 °C for 12 h. After completion of the reaction, the volatiles were removed under reduced pressure and the resulting residue was purified by Combi Flash® to obtain 4-methoxyphenyl 2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (120 mg, 39 % yield). 1H- NMR (400 MHz, CHLOROFORM-D) δ 7.61 (s, 1H), 7.05 (dd, 2H), 6.89 (d, 2H), 4.74 (d, 2H), 3.95 (d, 2H), 3.80 (s, 3H), 3.03 (s, 2H) LCMS (M+H): 425.65. The following compounds in Table 5 were prepared by using analogous procedures as described in Example 5. Table: 5
Figure imgf000082_0002
Figure imgf000083_0001
Example 6: Preparation of 2-(4-chlorophenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (Compound no.91) a) Step 1: 2-Chloro-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one To a stirred suspension of 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,5,6,7-tetrahydrothieno[3,2- c]pyridin-5-ium chloride (12.5 g, 40.1 mmol) in dichloromethane (100 mL), triethylamine (12.30 mL, 88 mmol) and 4-dimethylaminopyridine (2.45 g, 20 mmol) were added followed by the addition of 2- chloroacetyl chloride (6.38 mL, 80 mmol) in dichloromethane at 0 °C. The resulting reaction mixture was further stirred at 25 °C for 8 h. After completion of the reaction, the reaction mixture was extracted with dichloromethane (3 x 50 mL). The combined dichloromethane layers were washed with water (3 x 60 mL), brine solution (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product. The crude product was purified by Combi Flash® to obtain 2-chloro-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (11.5 g, 82 % yield). b) Step 2: 2-(4-chlorophenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (Compound no.91) To a stirred solution of 4-chlorophenol (0.11 g, 0.85 mmol) in acetonitrile (5 mL), potassium carbonate (0.15 g, 1.1 mmol) was added at 25 °C. The reaction mixture was stirred for 15 min at 25 °C, followed by the addition of 2-chloro-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (0.25 g, 0.71 mmol) at 0 °C. The resulting reaction mixture was further stirred at 50 °C for 8 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (30 mL). The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography to obtain 2-(4-chlorophenoxy)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (0.12 g, 37 % yield). 1H-NMR (400 MHz, CHLOROFORM-D) δ 7.59 (s, 1H), 7.29-7.23 (m, 2H), 6.90 (dd, 2H), 4.77-4.69 (m, 4H), 3.96-3.88 (m, 2H), 3.00-2.93 (m, 2H); LCMS (M+H): 444.00. The following compounds in Table 6 were prepared by using analogous procedure as described in Example 6. Table: 6
Figure imgf000084_0001
Figure imgf000085_0001
Figure imgf000086_0001
Figure imgf000087_0001
Figure imgf000088_0001
Example 7: Preparation of (3-chlorophenyl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone (Compound no.116) a) Step 1: 2,3-dibromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrobromide To a stirred solution of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (20 g, 114 mmol) in chloroform (400 mL), bromine (23.46 mL, 455 mmol) was added at 0 °C. The resulting reaction mixture was stirred at 40 °C for 16 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and diluted with ethyl acetate (600 mL). The resulting precipitate was filtered to obtain 2,3-dibromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrobromide (40 g, 93 % yield). b) Step 2: tert-butyl 2,3-dibromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate : To a stirred suspension of 2,3-dibromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-ium bromide (20 g, 52.9 mmol) in dichloromethane (200 mL), triethylamine (11.25g, 115mmol) and boc-anhydride (13.86 g, 63.5 mmol) were added at 25 °C. The resulting reaction mixture was stirred at 25 °C for 12 h. After completion of the reaction, the volatiles were removed under reduced pressure to obtain tert- butyl 2,3-dibromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (20 g, 95 % yield). c) Step 3: 3-bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-ium bromide To a stirred solution of tert-butyl 2,3-dibromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (15 g, 38 mmol) in acetic acid (500 mL), zinc (5 g, 76 mmol) and 10 M aqueous hydrochloric acid solution (20.77 mL, 208 mmol) were added. The resulting reaction mixture was stirred at 80 °C for 16 h. After completion of the reaction, the volatiles were removed under reduced pressure to obtain a residue. The residue was diluted with ethyl acetate (300 mL) to obtain a precipitate. The resulting precipitate was filtered to obtain 3-bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-ium bromide (8 g, 71 % yield). d) Step 4: tert-butyl 3-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate To a stirred suspension of 3-bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (18 g, 70.7 mmol) in dichloromethane (400 mL), triethylamine (15.03 g, 148 mmol ) and boc-anhydride (24.63 mL, 106 mmol) were added. The resulting reaction mixture was stirred at 25 °C for 12 h. After completion of the reaction, the volatiles were removed under reduced pressure to obtain crude tert- butyl 3-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (19 g, 84 % yield) which was used without further purification for the next step. e) Step 5: tert-butyl 3-cyano-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate To a stirred solution of tert-butyl 3-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (8 g, 25.1 mmol) in 1,4-dioxane (60 mL) and water (30 mL), Pd(xanphos)allylCl (0.9 g, 1.26 mmol), potassium acetate (1.234 g, 12.6 mmol) and potassium hexacyanoferrate(II)trihydrate (5.31 g, 12.6 mmol) were added under nitrogen atmosphere. The reaction mixture was degassed for 20 min by nitrogen purging. The resulting reaction mixture was further stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was filtered through a Buchner funnel, the filtrate was diluted with water (100 mL) and the product was extracted with ethyl acetate (3 X 50 mL). The combined ethyl acetate layers were washed with water (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product. The crude product was purified by flash column chromatography to obtain tert-butyl 3-cyano-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxylate (5.6 g, 84 % yield). f) Step 6: tert-butyl 3-(N'-hydroxycarbamimidoyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxylate To a stirred solution of tert-butyl 3-cyano-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (5.6 g, 21.18 mmol) in ethanol (60 mL), 50 % aqueous solution (4.91 mL, 42.4 mmol) of hydroxylamine was added at 0 °C. The resulting reaction mixture was stirred at 25 °C for 7 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain tert-butyl 3-(N'- hydroxycarbamimidoyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (6 g, 95 % yield) which was used without further purification for the next step. g) Step 7: tert-butyl 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxylate To a stirred solution of tert-butyl 3-(N'-hydroxycarbamimidoyl)-6,7-dihydrothieno[3,2-c]pyridine- 5(4H)-carboxylate (6.5 g, 21.9 mmol) in tetrahydrofuran (80 mL), triethylamine (4.6 mL, 33 mmol) was added. The reaction mixture was cooled to 0 °C followed by the dropwise addition of trifluoroacetic anhydride (6.17 mL, 43.7 mmol). The resulting reaction mixture was further stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (3 x 50 mL). The combined ethyl acetate layers were washed with water (50 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain a crude product. The crude product was purified by flash column chromatography to obtain tert-butyl 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxylate (5.8 g, 71 % yield). h) Step 8: 3-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole hydrochloride To a stirred solution of tert-butyl 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxylate (8 g, 21.31 mmol) in dichloromethane (200 mL), 4 M hydrochloric acid solution in 1,4-dioxane (15.98 mL, 63.9 mmol) was added at 0 °C. The resulting reaction mixture was stirred at 25 °C for 3 h. The resulting precipitate was filtered and dried under reduced pressure to obtain 3-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole hydrochloride (6 g, 90 % yield). i) Step 9: (3-chlorophenyl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)methanone (compound no.116) To a stirred solution of 3-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole hydrochloride (0.2 g, 0.642 mmol) in dichloromethane (5 mL), triethylamine (0.27 mL, 1.93 mmol) was added. The reaction mixture was cooled to 0 °C followed by the dropwise addition of 3-chlorobenzoyl chloride (0.123 mL, 0.962 mmol). The resulting reaction mixture was further stirred at 25 °C and 16 h. After completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted with dichloromethane (3 x 20 mL). The combined dichloromethane layers were washed with water, dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain a crude product. The crude product was purified by preparative HPLC to obtain (3- chlorophenyl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)methanone (99 mg, 37 % yield). 1H-NMR (400 MHz, DMSO-D6) δ 8.38 (s, 1H), 7.56-7.48 (m, 3H), 7.44 (dt, 1H), 4.84 (d, 2H), 3.80 (d, 2H), 2.96 (s, 2H); LCMS (M+H): 413.85. The following compounds in Table 7 were prepared by using analogous procedures as described in Example 7. Table: 7
Figure imgf000090_0001
Figure imgf000091_0001
Figure imgf000092_0001
Figure imgf000093_0001
Figure imgf000094_0001
Example 8: Preparation of 3-(5-(phenylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole (Compound no.143) To a stirred solution of 3-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole hydrochloride (0.18 g, 0.58 mmol) in dichloromethane (5 mL), triethylamine (0.24 mL, 1.73 mmol) was added. The reaction mixture was cooled to 0 °C followed by the dropwise addition of benzenesulfonyl chloride (0.148 mL, 1.155 mmol). The resulting reaction mixture was further stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted with dichloromethane (3 x 20 mL). The combined dichloromethane layers were washed with water (20 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain a crude product. The crude product was purified by flash column chromatography to obtain 3-(5-(phenylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole (165 mg, 69 % yield). 1H-NMR (400 MHz, DMSO-D6) δ 8.32 (s, 1H), 7.82-7.76 (m, 2H), 7.71-7.67 (m, 1H), 7.65-7.57 (m, 2H), 4.43 (s, 2H), 3.48 (t, 2H), 2.90 (t, 2H); LCMS (M+H): 415.85. The following compounds in Table 8 were prepared by using analogous procedures as described in Example 8. Table: 8
Figure imgf000095_0001
Figure imgf000096_0001
Example 9: Preparation of N-(2,6-dichlorophenyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide (Compound no 145) To a stirred solution of 3-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole hydrochloride (0.2 g, 0.642 mmol) in dichloromethane (5 mL), triethylamine (0.27 mL, 1.93 mmol) was added. The reaction mixture was cooled to 0 °C followed by the dropwise addition of 1,3-dichloro-2-isocyanatobenzene (0.15 g, 0.77 mmol). The resulting reaction mixture was further stirred at 25 °C for 12 h. After completion of the reaction, the volatiles were removed under reduced pressure to obtain a residue which was purified using preparative HPLC to obtain N-(2,6- dichlorophenyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxamide (170 mg, 57 % yield). 1H-NMR (400 MHz, DMSO-D6) δ 8.68 (s, 1H), 8.34 (s, 1H), 7.49 (d, 2H), 7.28 (t, 1H), 4.79 (s, 2H), 3.86 (t, 2H), 2.98 (d, 2H); LCMS (M+H): 462.15. The following compounds in Table 9 were prepared by using analogous procedures as described in Example 9. Table: 9
Figure imgf000097_0001
Example 10: Preparation of 2-(isopropylamino)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (Compound no.205) To a stirred solution of 2-chloro-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (0.2 g, 0.57 mmol) in acetonitrile (15 mL), propan- 2-amine (0.853 mL, 1.706 mmol) was added. The resulting reaction mixture was stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was diluted with water (50 mL) and extracted with dichloromethane (2 x 50 mL). The combined dichloromethane layers were dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure to obtain a crude product. The crude product was purified by preparative HPLC to obtain 2-(isopropylamino)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (0.077 g, 36 % yield). 1H-NMR (400 MHz, DMSO-D6) δ 7.77 (d, 1H), 4.65 (d, 2H), 4.12 (d, 2H), 3.82 (dt, 2H), 2.99 (dt, 2H), 1.23 (t, 6H); LCMS (M+H): 474.55. The following compounds in Table 10 were prepared by using analogous procedures as described in Example 10. Table: 10
Figure imgf000097_0002
Figure imgf000098_0001
Example 11: Preparation of N-(3-Fluorophenyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide (Compound no.182) a) Step 1: tert-butyl-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)acetate To a stirred solution of 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,5,6,7-tetrahydrothieno[3,2- c]pyridin-5-ium chloride (0.5 g, 1.604 mmol) in acetonitrile (10 mL), triethylamine (0.47 mL, 3.37 mmol) was added followed by the addition of tert-butyl-2-bromoacetate (0.284 mL, 1.925 mmol) at 0 °C. Then resulting reaction mixture was stirred at 25 °C for 8 h. After completion of the reaction, the reaction mixture was diluted with dichloromethane (20 mL), washed with water (10 x 2 mL) and with a solution of brine (20 mL). The dichloromethane layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product. The crude product was purified by combi flash to obtain tert-butyl-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate (0.49 g, 78 % yield). 1H-NMR (400 MHz, CHLOROFORM-D) δ 7.51 (s, 1H), 3.77 (s, 2H), 3.37 (s, 2H), 2.99 (s, 4H), 1.49 (s, 9H); LCMS (M+H): 389.55. b) Step 2: 2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)acetic acid (Compound no.226) To a stirred solution of tert-butyl-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate (0.8 g, 2.054 mmol) in dichloromethane (10 mL), hydrogen chloride (4M in 1,4-dioxane) (1.541 mL, 6.16 mmol) was added at 0 °C. The resulting reaction mixture was stirred at 25 °C for 8 h. After completion of the reaction, the reaction mixture was evaporated to dryness under reduced pressure to obtain a crude product. The crude product was co- evaporated with toluene (2 x 25 mL) under reduced pressure to obtain 2-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetic acid (0.62 g, 91 % yield). 1H-NMR (400 MHz, DMSO-D6) δ 11.83 (s, 1H), 7.82 (s, 1H), 4.54 (d, 2H), 4.27 (d, 2H), 3.76-3.55 (m, 2H), 3.37-3.25 (m, 2H); LCMS (M+H): 333.40. c) Step 3: N-(3-Fluorophenyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide (Compound no.182) To a stirred solution of 2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)acetic acid (0.35 g, 1.05 mmol) in ethyl acetate (10 mL), 3-fluoroaniline (0.140 g, 1.260 mmol) and triethylamine (0.439 mL, 3.15 mmol) were added followed by addition of propanephosphonic acid anhydride (1.671 mL, 2.63 mmol) slowly at 0 °C. The resulting reaction mixture was stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was quenched bu the addition of water (20 mL) and extracted with ethyl acetate (2 x 20 mL). The combined ethyl acetate layers were dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure to obtain a crude product. The crude product was purified by Combi Flash® to obtain N-(3- fluorophenyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)acetamide (0.29 g, 64 % yield). 1H-NMR (400 MHz, CHLOROFORM-D) δ 9.12 (s, 1H), 7.56-7.52 (m, 2H), 7.29-.25 (m, 1H), 7.19 (m, 1H), 6.82 (m, 1H), 3.78 (s, 2H), 3.37 (s, 2H), 3.04-2.99 (m, 4H); LCMS (M+H): 427.05. The following compounds in Table 11 were prepared by using analogous procedures as described in Example 11. Table: 11
Figure imgf000099_0001
Figure imgf000100_0001
Figure imgf000101_0001
Figure imgf000102_0001
Figure imgf000103_0001
Example 12: Preparation of N-((4-fluorophenyl)sulfonyl)-2-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide (Compound no.243) To a stirred solution of 2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)acetic acid (0.280 g, 0.840 mmol) in a mixture of tert-butanol (1 mL): dichloromethane (4 mL), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.4 g, 2.1 mmol) and 4-dimethylaminopyridine (0.26 g, 2.1 mmol) were added. After 10 min. of stirring, 4- fluorobenzenesulfonamide (0.177 g, 1.01 mmol) was added and the resulting reaction mixture was further stirred at 25 °C for 12 h. After completion of the reaction, the reaction mixture was diluted with water (30 mL) and extracted with dichloromethane (2 x 10 mL). The combined dichloromethane layers were washed with brine solution (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product. The crude product was purified by preparative HPLC to obtain N-((4-fluorophenyl)sulfonyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide (0.153 g, 37 % yield). 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.14-8.09 (m, 2H), 7.50 (s, 1H), 7.25-7.20 (m, 2H), 3.67 (s, 2H), 3.24 (s, 2H), 3.01 (m, 2H), 2.91 (m, 2H); LCMS (M+H): 491.10. Example 13: Preparation of 2-(phenylthio)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (Compound no.219) To a stirred solution of benzenethiol (0.078 g, 0.711 mmol) in tetrahydrofuran (5 mL), potassium carbonate (0.147 g, 1.7 mmol) was added at 25 °C. The reaction mixture was stirred for 15 min at 25 °C followed by the addition of 2-chloro-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (0.25 g, 0.711 mmol) at 0 °C. The resulting reaction mixture was further stirred at 25 °C for 3 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (30 mL). The ethyl acetate layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography to obtain 2-(phenylthio)-1- (2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one (0.187 g, 62 % yield). 1H-NMR (400 MHz, CHLOROFORM-D) δ 7.56 (d, 1H), 7.46-7.44 (m, 1H), 7.41-7.39 (m, 1H), 7.32-7.28-7.19 (m, 3H), 4.65 (d, 2H), 3.91 (t, 1H), 3.85-3.79 (m, 3H), 2.95 (m, 2H); LCMS (M+H): 426.05. The following compounds in Table 12 were prepared by using analogous procedures as described in Example 13. Table: 12
Figure imgf000104_0001
Figure imgf000105_0001
Example 14: Preparation of N-cyclopentyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide (Compound no.245) a) Step 1: tert-butyl 4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate To a stirred solution of 4,5,6,7-tetrahydrothieno[2,3-c]pyridine (46 g, 330 mmol) in dichloromethane (460 mL), triethylamine (138 mL, 991 mmol) was added, followed by the addition of boc-anhydride ( 91.1 mL, 396 mmol) for 1 h at 0 °C. The resulting reaction mixture was stirred at 25 °C for 14 h. After completion of the reaction, water (100 mL) was added into the reaction mixture, layers were separated and the aqueous layer was re-extracted with dichloromethane (300 mL). The combined dichloromethane layer was washed with water (100 mL) and brine solution (100 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain tert-butyl 4,7- dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate (72 g, 91 % Yield). b) Step 2: tert-butyl 2-bromo-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate To a stirred suspension of tert-butyl 4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate (10 g, 41.8 mmol) in acetonitrile (100 mL), N-bromosuccinimide (7.81 g, 43.9 mmol) was added portion wise for 20 min at 25 °C. The resulting reaction mixture was stirred at 25 °C for 14 h. After completion of the reaction, the reaction mixture was quenched with ice cold water (100 mL) and extracted with ethyl acetate (2 x 200 mL). The ethyl acetate layer washed with water (2 x 100 mL) followed by brine solution (100 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain a crude product. The crude product was purified by Combi Flash® to obtain tert-butyl 2- bromo-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate (7.4 g, 56 % yield). c) Step 3: tert-butyl 2-cyano-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate To a stirred suspension of tert-butyl 2-bromo-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate (50 g, 157 mmol) in N,N-dimethylformamide (250 mL), palladium(II) dichloride dichloromethane adduct (12.83 g, 15.71 mmol) was added at 25 °C. The reaction mixture was degassed with argon for 30 min, and Zinc (II) cyanide (46g, 393 mmol) was added into it. The resulting reaction mixture was stirred at 120 °C for 16 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and diluted with cold water (300 mL) and extracted with ethyl acetate (2 X 300 mL). The combined ethyl acetate layers were washed with 20 % aqueous sodium carbonate solution (300 mL) followed by washing with 0.1 N aqueous hydrochloric acid solution (300 mL) and with aqueous brine solution (300 mL). The resultant ethyl acetate layer was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography to obtain tert-butyl 2-cyano-4,7-dihydrothieno[2,3-c]pyridine-6(5H)- carboxylate (26 g, 63 % yield). d) Step 4: tert-butyl 2-(N'-hydroxycarbamimidoyl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)- carboxylate To a stirred solution of tert-butyl 2-cyano-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate in (0.41 g, 1.6 mmol) in ethanol (10 mL), triethylamine(0.65 mL, 4.7 mmol) was added followed by addition of hydroxyl amine hydrochloride(0.22 g, 3.11mmol) at 25 °C. The resulting reaction mixture was stirred for 65 °C for 5 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and the volatiles were removed under reduced pressure to obtain a residue. The residue was washed with n-pentane (5 mL), decanted the pentane layer and solid compound was dried under reduced pressure to obtain crude tert-butyl 2-(N'-hydroxycarbamimidoyl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxylate (0.7 g). e) Step 5: tert-butyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxylate To a stirred solution of tert-butyl 2-(N'-hydroxycarbamimidoyl)-4,7-dihydrothieno[2,3-c]pyridine- 6(5H)-carboxylate (28 g, 94.16 mmol) in tetrahydrofuran (150 mL), pyridine (29.8 mL, 376.6 mmol) was added at 25 °C. The reaction mixture was cooled to 0 °C and trifluoroacetic anhydride (59.33 g, 5.5 mmol) was added. The resulting reaction mixture was stirred for 24 h at 25 °C. After completion of the reaction, the reaction mixture was quenched with ice cold water (200 mL) and extracted with ethyl acetate (2 x 300 mL). The combined ethyl acetate layer was washed with aqueous saturated sodium bicarbonate solution (2 x 150 mL), brine solution (150 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain a crude product. The crude product was further purified by column chromatography to obtain tert-butyl 2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate (22 g, 62 % yield). f) Step 6: 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-6- ium 2,2,2-trifluoroacetate To a stirred solution of tert-butyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxylate (28.0 g, 74.66 mmol) in dichloromethane (100 mL), trifluoroacetic acid (25.5 g, 224 mmol) was added at 0 °C. The resulting reaction mixture was stirred at 25 oC for 2 h. After completion of the rection, the reaction mixture was concentrated under reduced pressure to obtain (2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-6-ium 2,2,2-trifluoroacetate. (23 g, 88 % yield). g) Step 7: N-cyclopentyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxamide (Compound no.245) To a stirred solution of 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,5,6,7-tetrahydrothieno[2,3- c]pyridin-6-ium 2,2,2-trifluoroacetate (400 mg, 1.028 mmol) in dichloromethane (10 mL), triethylamine (259.9 mg, 3.083 mmol) was added at 0 °C followed by the addition of isocyanatocyclopentane (172 mg, 1.54 mmol) under nitrogen atmosphere. The resulting reaction mixture was stirred at 25 °C for 12 h. After completion of the reaction, the reaction mixture was quenched with ice-water (10 mL), dichloromethane layer was isolated, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain a crude product. The crude product was precipitated by using 40 mL of 15 % ethyl acetate in hexane. The solid was isolated by filtration and dried under reduced pressure to obtain N-cyclopentyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide (240 mg, 48 % yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.70 (s, 1 H) 6.45 (d, 1 H) 4.63 (s, 2 H) 3.93 (d, 1 H) 3.62 (t, 2 H) 2.68 (br t, 2 H) 1.72 - 1.88 (m, 2 H), 1.61-1.69(m, 2H), 1.34 - 1.52 (m, 4 H); LCMS (M-H): 386.65. The following compounds in Table 13 were prepared by using analogous procedures as described in Example 14. Table: 13
Figure imgf000107_0001
Figure imgf000108_0001
Example 15: Preparation of p-tolyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone (Compound no.246) To a stirred solution of 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,5,6,7-tetrahydrothieno[2,3- c]pyridin-6-ium 2,2,2-trifluoroacetate (400 mg, 1.028 mmol) in dichloromethane (10 mL), triethylamine (259.9 mg, 3.083 mmol) was added at 0 °C, followed by the addition of 4-methyl- benzoyl chloride (238 mg, 1.54 mmol). The resulting reaction mixture was stirred at 25 °C for 12 h. After completion of the reaction, the reaction mixture was quenched with ice-water (10 mL), dichloromethane layer was isolated, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude product. The crude product was precipitated by using 40 mL of 10 % ethyl acetate in hexane. The solid was isolated by filtration and dried under reduced pressure to obtain a crude product. The crude product was purified by Combi Flash® to obtain p-tolyl(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone (280 mg, 69 % yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.70 - 7.79 (m, 1 H), 7.33 - 7.45 (m, 2 H), 7.24 - 7.31 (m, 2 H), 4.88 (br s, 2 H), 3.54 - 3.98 (m, 2 H), 2.80 (br s, 2 H), 2.36 (s, 3 H); LCMS (M+H): 393.6. The following compounds in Table 14 were prepared by using analogous procedures as described in Example 15. Table: 14
Figure imgf000108_0002
Figure imgf000109_0001
Figure imgf000110_0001
Example 16: Preparation of 3-(6-((3-fluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[2,3- c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole (Compound no.247) To a stirred solution of 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,5,6,7-tetrahydrothieno[2,3- c]pyridin-6-ium 2,2,2-trifluoroacetate (400 mg, 1.028 mmol) in dichloromethane (10 mL), triethylamine (540 µL, 3.85 mmol) was added at 0 °C, followed by the addition of 3- fluorobenzenesulfonyl chloride (238 mg, 1.93 mmol). The resultant reaction mixture was stirred at 25 °C for 12 h. After completion of the reaction, the reaction mixture was quenched with ice-water (30 mL), dichloromethane layer was separated, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain a crude product. The resultant crude was precipitated by using 40 mL of 5% ethyl acetate in hexane solution. The solid was isolated by filtration, dried under reduced pressure and purified by column chromatography to obtain 3-(6-((3-fluorophenyl)sulfonyl)-4,5,6,7- tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole (210 mg, 38 %). 1H-NMR (400 MHz, DMSO-d6) δ ppm 7.50 - 7.76 (m, 5 H), 4.52 (s, 2 H), 3.47 (br t, 2 H), 2.72 (br s, 2 H); LCMS (M+H): 433.75. The following compounds in Table 15 were prepared by using analogous procedures as described in Example 16. Table: 15
Figure imgf000111_0001
Figure imgf000112_0001
Further, the following compounds in Table 16 were prepared by using analogous procedures as described in Example 14 to 16. Table: 16
Figure imgf000112_0002
Figure imgf000113_0001
Figure imgf000114_0001
Figure imgf000115_0001
Figure imgf000116_0001
BIOLOGY EXAMPLES: As described herein the compounds of formula (I) show fungicidal activity which is exerted with respect to numerous phytopathogenic fungi which attack on important agricultural crops. The compounds of the present invention were assessed for their activity as described in the following tests: Example 1: Pyricularia oryzae (rice blast): The compounds were dissolved in 0.3 % dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium with the compound in the desired test concentration was dispensed into a 60 mm sterile petri-plate. After solidification, each plate was seeded with a 5 mm size mycelial disc taken from the periphery of an actively growing virulent culture plate of Pyricularia oryzae. The plates were incubated in growth chambers at 25 °C temperature and 60 % relative humidity for seven days and the radial growth was measured and compared to the one of the untreated control. Compounds 4 5 7 8 9 10 11 15 21 25 40 51 53 58 59 61 62 65 69 70 72 73 74 75 76 80 81 83 84 91 92 94 95 103 110 114 at 300 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive pathogen growth. Example 2: Botrytis cinerea (gray mold): The compounds were dissolved in 0.3 % dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium with the compound in the desired test concentration was dispensed into a 60 mm sterile petri-plate. After solidification, each plate was seeded with a 5 mm size mycelial disc taken from the periphery of an actively growing virulent culture plate of Botrytis cinerea. The plates were incubated in growth chambers at 22 °C temperature and 90 % relative humidity for seven days and the radial growth was measured and compared to the one of the untreated control. Compounds 110 and 114 at 300 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive pathogen growth. Example 3: Alternaria solani (early blight of tomato/potato): The compounds were dissolved in 0.3 % dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium with the compound in the desired test concentration was dispensed into a 60 mm sterile petri-plate. After solidification, each plate was seeded with a 5 mm size mycelial disc taken from the periphery of an actively growing virulent culture plate of Alternaria solani. The plates were incubated in growth chambers at 25 °C temperature and 60 % relative humidity for seven days and the radial growth was measured and compared to the one of the untreated control. Compounds 3 4 5 7 8 9 10 15 21 52 78 80 91 95 at 300 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive pathogen growth. Example 4: Colletotrichum capsici (anthracnose): The compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium with the compound in the desired test concentration was dispensed into a 60 mm sterile petri-plate. After solidification, each plate was seeded with a 5 mm size mycelial disc taken from the periphery of an actively growing virulent culture plate of Colletotrichum capsici. The plates were incubated in growth chambers at 25 °C temperature and 60% relative humidity for seven days and the radial growth was measured and compared to the one of the untreated control. Compounds 5 15 21 27 80 at 300 ppm gave more than or equal to 70% control in these tests when compared to the untreated check which showed extensive pathogen growth. Example 5: Corynespora cassiicola (leaf spot of tomato): The compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium with the compound in the desired test concentration was dispensed into a 60 mm sterile petri-plate. After solidification, each plate was seeded with a 5 mm size mycelial disc taken from the periphery of an actively growing virulent culture plate of Corynespora cassiicola. The plates were incubated in growth chambers at 25 °C temperature and 70% relative humidity for seven days and the radial growth was measured and compared to the one of the untreated control. Compounds 9 21 51 54 87 89 90 92 114 at 300 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive pathogen growth. Biological test examples on plants The compounds were further selected for greenhouse trials. The methods followed to test the preventive efficacy of compounds on the respective pathogens were as following: Example 1: Phakopsora pachyrhizi (on soybean plants): The compounds were dissolved in 2 % dimethyl sulfoxide/acetone and then mixed with water containing an emulsifier to the calibrated spray volume of 30 mL. Each spray solution was poured into a spray bottle for further application. To test the preventive activity of the compound, healthy young soybean plants, raised in the greenhouse, were sprayed with the active compound preparation at the stated application rate inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a conidial suspension containing 2 x105 Phakopsora pachyrhizi inoculum. The inoculated plants were then kept in a greenhouse chamber at 22-24 °C temperature and 80-90 % relative humidity for disease expression. A visual assessment of the compound’s performance was carried out by rating the disease severity (0- 100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compound was calculated by comparing the disease rating in the treatment with the one of the untreated control. The treated plants were also assessed for plant damage by recording symptoms like necrosis, chlorosis and stunting. Compounds 1 2 3 4 5 9 10 11 12 13 14 15 16 18 19 20 21 23 24 25 26 28 29 30 32 34 36 37 38 39 40 41 43 44 45 46 47 48 49 50 51 52 53 54 55 56 59 60 64 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 82 83 84 85 86 87 88 89 90 91 92 93 94 95 100 105 106 107 108 109 110 111 112 113 114 115 at 300 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive disease development. Having described the invention with reference to certain preferred aspects, other aspects will become apparent to one skilled in the art from consideration of the specification. It will be apparent to those skilled in the art that many modifications, both to materials and methods, may be practiced without departing from the scope of the invention.

Claims

CLAIMS: 1) A compound of formula (I),
Figure imgf000120_0001
Formula (I) wherein, Z1 and Z2 represent CHR2 or N-R3; provided that (iii) both Z1 and Z2 are not CHR2 simultaneously; (iv) both Z1 and Z2 are not N-R3 simultaneously; R1 is C1-C6 haloalkyl; R2 is selected from the group consisting of hydrogen, halogen, cyano, nitro, thiol, amino, hydroxy, C1-C6-alkyl, C2-C6-alkenyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-haloalkenyl, C3-C8-halocycloalkyl, C1-C6- alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-haloalkylsulfonyl, C1-C6- alkylsulfonyl, C1-C6-alkylamino, C1-C6-dialkylamino and C3-C8-cycloalkylamino; wherein the aliphatic or cyclic moieties of R2 may optionally be substituted with one or more groups of R2a; R2a is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C1- C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6- haloalkylthio, C3-C8-cycloalkyl and C1-C6-alkoxy-C1-C6-alkyl; R3 is selected from the group consisting of C1-C6-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C3-C8-halocycloalkyl, C6-C10- aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl, C3-C8-heterocyclyl-C1-C6-alkyl, -(CHR9)n- C(=O)-R4, -C(=O)-(CHR9)n-R4, -C(=O)-(CHR9)n-O-R4, -C(=O)-(CHR9)n-S-R4, -C(=O)-(CHR9)n- N(R5)(R6), -(CHR9)n-(C=O)-C(=O)-R4, -(CHR9)n-C(=O)-O-R4, -(C=O)-C(=O)-O-R4, -(CHR9)n- C(=O)-(CHR9)n-N(R5)(R6), -(CHR9)n-(C=O)-C(=O)-N(R5)(R6), -S(O)2-R4, -(CHR9)n-N(R5)- C(=O)-R4, -(CHR9)n-N(R5)-C(=O)-O-R4, -(CHR9)n-C(=O)-N(R5)-S(=O)n-R4, -(CHR9)n-N(R5)- S(=O)n-R4, -(CHR9)n-N(R5)-C(=O)-N(R5)(R6) and -S(O)2-N(R5)(R6); wherein the aliphatic or cyclic moieties of R3 may optionally be substituted with one or more groups of R3a; R3a is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thio, amino, C1- C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C6-haloalkoxy, C1-C6- alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, phenyl, benzyl, and C3-C10-heterocyclyl; wherein each group of R3a may optionally be substituted with one or more groups selected from halogen, cyano, nitro, hydroxyl, thio, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6- alkoxy, C1-C4-alkoxy-C1-C4-alkyl or C1-C6-haloalkoxy; R4 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6 alkoxy-C1-C6-alkyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, C1-C6- dialkylamino, C3-C8-cycloalkylamino, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl and C3-C8-heterocyclyl-C1-C6-alkyl; each group of R4 may optionally be substituted with one or more groups of R4a; R4a is selected from the group consisting of halogen, cyano, amino, C1-C6-alkylamino, C1-C6- dialkylamino, C1-C6-alkyl, C1-C6-alkylthio, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy and phenoxy; R5 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6- alkoxy and C1-C6-haloalkyl; R6 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6 alkoxy-C1-C6-alkyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C6-C10-aryl, C6-C10-aryl-C1-C6- alkyl, C3-C8-heterocyclyl and C3-C8-heterocyclyl-C1-C6-alkyl; each group of R6 may optionally be substituted with one or more groups of R6a; R6a may be optionally substituted with halogen, cyano, amino, C1-C6-alkylamino, C1-C6 dialkylamino, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkyl, C1-C6-alkylthio, C3-C6-cycloalkyl, C3-C6-cycloalkoxy and phenoxy; or R5 and R6 together with the atom to which they are attached may form a fused or non-fused 4-8 membered heterocyclic ring containing at least one heteroatom selected from O, S(=O)0-2, or NR7 and which may be optionally substitutes with one or more groups of R8; R7 is selected from the group consisting of hydrogen, C1-6-alkyl and C3-6-cycloalkyl; R8 is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C1-C6- alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3- C8-cycloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C6-C10-aryloxy, C6-C10-arylthio, C6-C10-aryl-C1-C6-alkoxy, C3-C10-heterocyclyl and C3-C10-heterocyclyloxy; R9 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6- alkoxy and C1-C6-haloalkyl; each group of R2 to R9, R2a, R3a, R4a and R6a may be optionally substituted with one or more groups selected from the group consisting of halogen, cyano, nitro, R’, OR’, SR’, N(R’)2, COR’ and CON(R’)2; R’ is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6- haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkoxy, C6-C10-aryl-C1-C6-alkyl and C3-C10-heterocyclyl; m and n is an integer selected from 0 to 3; or N-oxides, metal complexes, isomers, polymorphs, or agriculturally acceptable salts thereof. 2) The compound formula (I) according to claim 1, wherein R1 is selected from the group consisting of CF3, CHF2 and CF2Cl; R2 is selected from the group consisting of hydrogen, halogen, cyano, nitro, thiol, amino, hydroxy, C1-C6-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-alkoxy-C1-C6-alkyl; R3 is selected from the group consisting of C1-C6-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1- C6-alkyl, C3-C8-halocycloalkyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl, C3-C8- heterocyclyl-C1-C6-alkyl, -(CHR9)n-C(=O)-R4, -C(=O)-(CHR9)n-R4, -C(=O)-(CHR9)n-O-R4, - C(=O)-(CHR9)n-S-R4, -C(=O)-(CHR9)n-N(R5)(R6), -(CHR9)n-(C=O)-C(=O)-R4, -(CHR9)n-C(=O)- O-R4, -(C=O)-C(=O)-O-R4, -(CHR9)n-C(=O)-(CHR9)n-N(R5)(R6), -(CHR9)n-(C=O)-C(=O)- N(R5)(R6), -S(O)2-R4, -(CHR9)n-N(R5)-C(=O)-R4, -(CHR9)n-N(R5)-C(=O)-O-R4, -(CHR9)n-C(=O)- N(R5)-S(=O)n-R4, -(CHR9)n-N(R5)-S(=O)n-R4 and -S(O)2-N(R5)(R6); wherein the aliphatic or cyclic moieties of R3 may optionally be substituted with one or more groups of R3a; R3a is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thio, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, phenyl, benzyl, and C3-C10- heterocyclyl; wherein each group of R3a may optionally be substituted with one or more groups selected from halogen, cyano, nitro, hydroxyl, thio, amino, C1-C6-alkyl, C1-C6- haloalkyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkyl or C1-C6-haloalkoxy; R4 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6 alkoxy-C1-C6-alkyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, C1-C6- dialkylamino, C3-C8-cycloalkylamino, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl and C3-C8-heterocyclyl-C1-C6-alkyl; each group of R4 may optionally be substituted with one or more groups of R4a; R4a is selected from the group consisting of halogen, cyano, amino, C1-C6-alkylamino, C1- C6-dialkylamino, C1-C6-alkyl, C1-C6-alkylthio, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6- cycloalkyl, C3-C6-cycloalkoxy and phenoxy; R5 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl; R6 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl and C3-C8-heterocyclyl-C1-C6-alkyl; each group of R6 may optionally be substituted with one or more groups of R6a; R6a may be optionally substituted with halogen, cyano, amino, C1-C6-alkylamino, C1-C6 dialkylamino, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkyl, C1-C6- alkylthio, C3-C6-cycloalkyl, C3-C6-cycloalkoxy and phenoxy; or R5 and R6 together with the atom to which they are attached may form a fused or non-fused 4-8 membered heterocyclic ring containing at least one heteroatom selected from O, S(=O)0-2, or NR7 and which may be optionally substitutes with one or more groups of R8 ; R7 is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl; R8 is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C1-C6- alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylthio and C3-C8-cycloalkyl; R9 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl; n is an integer selected from 0 to 2. 3) The compound formula (I) according to claim 1, wherein Z1 represent N-R3 and Z2 represent CHR2; R1 is selected from the group consisting of CF3, CHF2 and CF2Cl; R2 is selected from the group consisting of hydrogen, halogen, cyano, nitro, thiol, amino, hydroxy, C1-C6-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-alkoxy-C1-C6-alkyl; R3 is selected from the group consisting of C1-C6-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1- C6-alkyl, C3-C8-halocycloalkyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl, C3-C8- heterocyclyl-C1-C6-alkyl, -(CHR9)n-C(=O)-R4, -C(=O)-(CHR9)n-R4, -C(=O)-(CHR9)n-O-R4, - C(=O)-(CHR9)n-S-R4, -C(=O)-(CHR9)n-N(R5)(R6), -(CHR9)n-(C=O)-C(=O)-R4, -(CHR9)n-C(=O)- O-R4, -(C=O)-C(=O)-O-R4, -(CHR9)n-C(=O)-(CHR9)n-N(R5)(R6), -(CHR9)n-(C=O)-C(=O)- N(R5)(R6), -S(O)2-R4, -(CHR9)n-N(R5)-C(=O)-R4, -(CHR9)n-N(R5)-C(=O)-O-R4, -(CHR9)n-C(=O)- N(R5)-S(=O)n-R4, -(CHR9)n-N(R5)-S(=O)n-R4 and -S(O)2-N(R5)(R6); wherein the aliphatic or cyclic moieties of R3 may optionally be substituted with one or more groups of R3a; R3a is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thio, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, phenyl, benzyl, and C3-C10- heterocyclyl; wherein each group of R3a may optionally be substituted with one or more groups selected from halogen, cyano, nitro, hydroxyl, thio, amino, C1-C6-alkyl, C1-C6- haloalkyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkyl or C1-C6-haloalkoxy; R4 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6 alkoxy-C1-C6-alkyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, C1-C6- dialkylamino, C3-C8-cycloalkylamino, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl and C3-C8-heterocyclyl-C1-C6-alkyl; each group of R4 may optionally be substituted with one or more groups of R4a; R4a is selected from the group consisting of halogen, cyano, amino, C1-C6-alkylamino, C1- C6-dialkylamino, C1-C6-alkyl, C1-C6-alkylthio, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6- cycloalkyl, C3-C6-cycloalkoxy and phenoxy; R5 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl; R6 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl and C3-C8-heterocyclyl-C1-C6-alkyl; each group of R6 may optionally be substituted with one or more groups of R6a; R6a may be optionally substituted with halogen, cyano, amino, C1-C6-alkylamino, C1-C6 dialkylamino, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkyl, C1-C6- alkylthio, C3-C6-cycloalkyl, C3-C6-cycloalkoxy and phenoxy; or R5 and R6 together with the atom to which they are attached may form a fused or non-fused 4-8 membered heterocyclic ring containing at least one heteroatom selected from O, S(=O)0-2, or NR7 and which may be optionally substitutes with one or more groups of R8 ; R7 is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl; R8 is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C1-C6- alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylthio and C3-C8-cycloalkyl; R9 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl; n is an integer selected from 0 to 2. 4) The compound formula (I) according to claim 1, wherein Z1 represent CHR2 and Z2 represent N-R3; R1 is selected from the group consisting of CF3, CHF2 and CF2Cl; R2 is selected from the group consisting of hydrogen, halogen, cyano, nitro, thiol, amino, hydroxy, C1-C6-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-alkoxy-C1-C6-alkyl; R3 is selected from the group consisting of C1-C6-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1- C6-alkyl, C3-C8-halocycloalkyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl, C3-C8- heterocyclyl-C1-C6-alkyl, -(CHR9)n-C(=O)-R4, -C(=O)-(CHR9)n-R4, -C(=O)-(CHR9)n-O-R4, - C(=O)-(CHR9)n-S-R4, -C(=O)-(CHR9)n-N(R5)(R6), -(CHR9)n-(C=O)-C(=O)-R4, -(CHR9)n-C(=O)- O-R4, -(C=O)-C(=O)-O-R4, -(CHR9)n-C(=O)-(CHR9)n-N(R5)(R6), -(CHR9)n-(C=O)-C(=O)- N(R5)(R6), -S(O)2-R4, -(CHR9)n-N(R5)-C(=O)-R4, -(CHR9)n-N(R5)-C(=O)-O-R4, -(CHR9)n-C(=O)- N(R5)-S(=O)n-R4, -(CHR9)n-N(R5)-S(=O)n-R4 and -S(O)2-N(R5)(R6); wherein the aliphatic or cyclic moieties of R3 may optionally be substituted with one or more groups of R3a; R3a is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thio, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, phenyl, benzyl, and C3-C10- heterocyclyl; wherein each group of R3a may optionally be substituted with one or more groups selected from halogen, cyano, nitro, hydroxyl, thio, amino, C1-C6-alkyl, C1-C6- haloalkyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkyl or C1-C6-haloalkoxy; R4 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6 alkoxy-C1-C6-alkyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, C1-C6- dialkylamino, C3-C8-cycloalkylamino, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl and C3-C8-heterocyclyl-C1-C6-alkyl; each group of R4 may optionally be substituted with one or more groups of R4a; R4a is selected from the group consisting of halogen, cyano, amino, C1-C6-alkylamino, C1- C6-dialkylamino, C1-C6-alkyl, C1-C6-alkylthio, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6- cycloalkyl, C3-C6-cycloalkoxy and phenoxy; R5 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl; R6 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C6-C10-aryl, C6-C10-aryl-C1-C6-alkyl, C3-C8-heterocyclyl and C3-C8-heterocyclyl-C1-C6-alkyl; each group of R6 may optionally be substituted with one or more groups of R6a; R6a may be optionally substituted with halogen, cyano, amino, C1-C6-alkylamino, C1-C6 dialkylamino, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkyl, C1-C6- alkylthio, C3-C6-cycloalkyl, C3-C6-cycloalkoxy and phenoxy; or R5 and R6 together with the atom to which they are attached may form a fused or non-fused 4-8 membered heterocyclic ring containing at least one heteroatom selected from O, S(=O)0-2, or NR7 and which may be optionally substitutes with one or more groups of R8 ; R7 is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C6-cycloalkyl; R8 is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C1-C6- alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylthio and C3-C8-cycloalkyl; R9 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl; n is an integer selected from 0 to 2. 5) The compound of formula (I) according to claim 1, wherein said compound of formula (I) is selected from (4-methoxyphenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, (3-methoxyphenyl)(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, p-tolyl(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, pyridin-3-yl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)methanone, (4-chlorophenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, (2,4-difluorophenyl)(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 2-(4- methoxyphenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)ethan-1-one, 2-(4-chlorophenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, cyclobutyl(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, cyclopropyl(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, (1- methyl-1H-pyrazol-3-yl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)methanone, (2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)(4-(trifluoromethyl)phenyl)methanone, (4-fluorophenyl)(2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, phenyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)methanone, 1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)ethan-1-one, 2-methyl-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan-1-one, 3-methyl-1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)butan-1-one, 4-(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-5-carbonyl)benzonitrile, (2- fluorophenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)methanone, 2-phenyl-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, (1-methyl-1H-pyrazol-4-yl)(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, ethyl 2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)acetate, N,N-dimethyl-2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-ethyl-2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-methyl-2-oxo-2-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N- (cyclopropylmethyl)-2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, 3-(5-((4-chlorophenyl)sulfonyl)-4,5,6,7- tetrahydrothieno[3,2-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 5-(trifluoromethyl)-3- (5-((4-(trifluoromethyl)phenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-1,2,4- oxadiazole, 3-(5-tosyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole, 3-(5-((2,4-difluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole, 3-(5-(phenylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin- 2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(5-(methylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2- c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 5-(trifluoromethyl)-3-(5-((3- (trifluoromethyl)phenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-1,2,4-oxadiazole, 3-(5-((3-chlorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-5-(trifluoromethyl)- 1,2,4-oxadiazole, 3-(5-((4-fluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole, 3-(5-((2-fluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2- c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(5-((2-chloro-4-fluorophenyl)sulfonyl)- 4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 5- (trifluoromethyl)-3-(5-((trifluoromethyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)- 1,2,4-oxadiazole, 3-(5-(cyclopropylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole, 3-(5-(propylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin- 2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(5-((3-fluorophenyl)sulfonyl)-4,5,6,7- tetrahydrothieno[3,2-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 2-(2-chlorophenoxy)- 1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1- one, 3-(5-((2-chloro-6-methylphenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole, 2-((6-fluoropyridin-3-yl)oxy)-1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(4-fluorophenoxy)-1-(2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan- 1-one, 2,2-dimethyl-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)propan-1-one, 1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)butan-1-one, (3-fluorophenyl)(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, m-tolyl(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 2- phenyl-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)propan-1-one, 2-(3,4-difluorophenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(m-tolyl)-1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, thiazol-4-yl(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, pyrimidin-5-yl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)methanone, 2-(4-chlorophenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan-1-one, (3-chlorophenyl)(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, N-(4-chlorophenyl)- 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxamide, N-phenyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxamide, N-(4-methoxyphenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(2,3-difluorophenyl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N- (3,5-difluorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxamide, N-cyclopentyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-cyclobutyl-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(cyclopropylmethyl)-2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(tert-butyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine- 5(4H)-carboxamide, N-isopropyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(p-tolyl)-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(4-fluorophenyl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N- (2-chlorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine- 5(4H)-carboxamide, N-(3-methoxyphenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(3-chlorophenyl)-2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(3-fluorobenzyl)- 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxamide, N-(4-fluorobenzyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(3-fluorophenyl)-2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(2,2,2- trifluoroethyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine- 5(4H)-carboxamide, N-cyclopropyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(3,5-dimethylisoxazol-4-yl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N- (2,6-diisopropylphenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxamide, 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-N-(1,3,5-trimethyl- 1H-pyrazol-4-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(2-fluorobenzyl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N- ethyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxamide, N-(4-fluoro-2-methylphenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(tetrahydro-2H-pyran-4-yl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N- benzyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxamide, N-(2-chlorobenzyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, ethyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate, N-(3,5-dichlorophenyl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N- (pyridin-3-yl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine- 5(4H)-carboxamide, N-(2,4-difluorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, 2-(4-chlorophenoxy)-1-(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(4-chloro-2- fluorophenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)ethan-1-one, 2-(2-fluoro-4-methylphenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(2,4-difluorophenoxy)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2- (2-fluorophenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one, 2-(2-fluorophenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(2-chloro-4-fluorophenoxy)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2- (2-methoxy-4-methylphenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(4-(methylthio)phenoxy)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2- (o-tolyloxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)ethan-1-one, 2-(4-chloro-2-methylphenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(3-fluorophenoxy)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2- (3-chlorophenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one, 2-(p-tolyloxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(3-(dimethylamino)phenoxy)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2- (3-methoxyphenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one, 2-(3,5-dichlorophenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(2-chloro-6- fluorophenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)ethan-1-one, 2-(4-fluoro-2-methylphenoxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-((1-methyl-1H-pyrazol-3-yl)oxy)-1- (2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1- one, 4-methoxyphenyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxylate, p-tolyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate, isobutyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate, methyl 2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate, 4-chlorophenyl 2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate, (3- chlorophenyl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)methanone, (3-fluorophenyl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, (2-fluorophenyl)(3-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, p-tolyl(3-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 1- (3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan-1- one, phenyl(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)methanone, o-tolyl(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)methanone, (4-(tert-butyl)phenyl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, (3-methoxycyclobutyl)(3-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 3- methyl-1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)butan-1-one, (4-fluorophenyl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-2-(4-(trifluoromethyl)phenyl)ethan-1-one, 2-(4- fluorophenyl)-1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)ethan-1-one, 2-(5-fluoropyridin-3-yl)-1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-phenyl-1-(3-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(2-chlorophenyl)-1-(3- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, (3,5-bis(trifluoromethyl)phenyl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 2-(4-chlorophenyl)-1-(3-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-phenyl-1-(3-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan-1-one, cyclobutyl(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)methanone, (1-methyl-1H-pyrazol-3-yl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 2-(thiazol-4-yl)-1-(3-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(pyrimidin-5-yl)-1-(3- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(3-chlorophenyl)-1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)propan-1-one, 2-(4-methoxyphenyl)-1-(3-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan-1-one, 1-(3-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2- (4-fluorophenyl)-1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)propan-1-one, 3-(5-(phenylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole, 3-(5-((4-chloro-2-methylphenyl)sulfonyl)-4,5,6,7- tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, N-(2,6- dichlorophenyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine- 5(4H)-carboxamide, N-(4-chlorophenyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(2-chloro-6-fluorophenyl)-3-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, 2- (3-fluorophenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)ethan-1-one, 2-methoxy-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan-1-one, pyridin-4-yl(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 2-(p-tolyl)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, (tetrahydrofuran-3-yl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)methanone, 2-(3,4-dichlorophenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(2-fluorophenyl)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, oxazol-4-yl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)methanone, isoxazol-3-yl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)methanone, 2-(o-tolyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(2-chlorophenyl)-1-(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(pyrazin-2-yl)-1- (2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1- one, o-tolyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)methanone, pyridin-2-yl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)methanone, (1-methyl-1H-pyrazol-5-yl)(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 3-methoxy-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)propan-1-one, (3-chloro-4-fluorophenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)methanone, 2-(4-fluorophenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, (3-chloro-4-methoxyphenyl)(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, (2- chloro-5-methoxyphenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)methanone, 1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)-2-(4-(trifluoromethyl)phenyl)ethan-1-one, 2-(3,4- dimethylphenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)ethan-1-one, (3,3-difluorocyclopentyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-5-carbonyl)benzonitrile, 3,3-dimethyl-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)butan-1-one, (4- (difluoromethyl)phenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)methanone, 2-(4-bromophenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(4-chloro-2-fluorophenyl)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2- (2,4-dichlorophenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one, 2-(2,4-difluorophenyl)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(1-methyl-1H-pyrazol-4-yl)-1-(2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, oxetan-3-yl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)methanone, 2-morpholino-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(piperidin-1-yl)-1-(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, N-(3-fluorophenyl)- 2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)acetamide, N-phenyl-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)acetamide, N-(p-tolyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(2-methoxyphenyl)-2-(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(5-methylthiazol-2- yl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)acetamide, N-isopropyl-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)acetamide, N-(pyrimidin-5-yl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(2-fluorophenyl)-2-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N- (1-methyl-1H-pyrazol-4-yl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-cyclopentyl-2-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(4-fluorophenyl)-2-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N- (pyridin-3-yl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)acetamide, N-(3-chlorophenyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(2-chlorophenyl)-2-(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, 2-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-N-(4- (trifluoromethyl)phenyl)acetamide, N-(4-chlorophenyl)-N-methyl-2-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(3,4-dichlorophenyl)-2- (2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)acetamide, N-(2-chloro-6-fluorophenyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(2,4-difluorophenyl)-2-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N- (4-chlorophenyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin- 5(4H)-yl)acetamide, N-propyl-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(3-methoxyphenyl)-2-(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-(4-fluorophenyl)- N-methyl-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)acetamide, 2-(isopropylamino)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, N-(4-fluorobenzyl)-2-(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N-cyclobutyl-2-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N- (4-methylbenzyl)-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)acetamide, N-benzyl-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, 2-((2-chloropyridin-3-yl)oxy)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2- ((2-methoxypyrimidin-5-yl)oxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-((5-methoxypyridin-3-yl)oxy)-1-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2- ((5-fluoropyridin-3-yl)oxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 5-(2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethoxy)nicotinonitrile, 2-((5- chloropyridin-3-yl)oxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one, 2-((4-fluorophenyl)thio)-1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-(thiazol-2-ylthio)-1-(2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, 2-((4-chlorophenyl)thio)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one, 2-(phenylthio)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, cyclopentyl 2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate, propyl 2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate, 2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-N-(4-(trifluoromethyl)phenyl)-6,7-dihydrothieno[3,2- c]pyridine-5(4H)-carboxamide, 2-chlorophenyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7- dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate, N-(2,6-dichlorophenyl)-2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, N-(2-chloro-6- fluorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine- 5(4H)-carboxamide, 2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)acetic acid, 3-(5-((4-chlorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2- c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 5-(trifluoromethyl)-3-(5-((4- (trifluoromethyl)phenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-1,2,4-oxadiazole, 3-(5-tosyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(5- ((2,4-difluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)- 1,2,4-oxadiazole, 3-(5-((4-fluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole, 3-(5-((2-fluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2- c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(5-((3-fluorophenyl)sulfonyl)-4,5,6,7- tetrahydrothieno[3,2-c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 5-(trifluoromethyl)-3- (5-((3-(trifluoromethyl)phenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-1,2,4- oxadiazole, 3-(5-(propylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-3-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole, 3-(5-(cyclopropylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2- c]pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, N-(3-chlorophenyl)-3-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide, (3-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)(4- (trifluoromethyl)phenyl)methanone, (4-chlorophenyl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)methanone, 2-((1-methyl-1H-pyrazol-4-yl)amino)- 1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1- one, 2-(cyclopentylamino)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2- c]pyridin-5(4H)-yl)ethan-1-one, 2-(p-tolylamino)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethan-1-one, N-((4-fluorophenyl)sulfonyl)-2-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetamide, N- propyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)- carboxamide, N-cyclobutyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxamide, N-ethyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-cyclopentyl-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-phenyl-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N- methyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)- carboxamide, N-isobutyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxamide, N-(tetrahydro-2H-pyran-4-yl)-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(3-methoxycyclobutyl)- 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)- carboxamide, N-(4-chlorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(4-(trifluoromethoxy)phenyl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N- (4-fluorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine- 6(5H)-carboxamide, N-(pyrimidin-5-yl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(pyridin-3-yl)-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(2-fluorophenyl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N- (2,4-difluorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxamide, N-(2-chlorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(p-tolyl)-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(3- (difluoromethyl)phenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxamide, N-(thiazol-4-yl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(4-chlorobenzyl)-2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(thiazol-2-yl)-2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(1-phenylethyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine- 6(5H)-carboxamide, 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-N-(4-(trifluoromethyl)phenyl)- 4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(3,4-dichlorophenyl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N- (4-(difluoromethyl)phenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxamide, N-(2,6-dichlorophenyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(4-methylbenzyl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N- (4-fluorobenzyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine- 6(5H)-carboxamide, N-(pyridin-3-ylmethyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(isoxazol-4-yl)-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(4-methoxybenzyl)-2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(1-methyl-1H-pyrazol-4-yl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-benzyl-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(3-fluorophenyl)-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N,N-diethyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)- carboxamide, N,N-dimethyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxamide, morpholino(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, pyrrolidin-1-yl(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, (4-methoxyphenyl)(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, (4- chlorophenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin- 6(5H)-yl)methanone, p-tolyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridin-6(5H)-yl)methanone, (4-fluorophenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, (2,4-difluorophenyl)(2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, (2-fluorophenyl)(2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, o-tolyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)- yl)methanone, (2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin- 6(5H)-yl)(2-(trifluoromethyl)phenyl)methanone, phenyl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, (4-(trifluoromethoxy)phenyl)(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, (2,4-dimethylphenyl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridin-6(5H)-yl)methanone, pyridin-4-yl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, pyridin-3-yl(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, pyridin-2-yl(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, (2- fluoropyridin-4-yl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin- 6(5H)-yl)methanone, pyrimidin-4-yl(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, 1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)ethan-1-one, cyclopropyl(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, cyclobutyl(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, 2,2,2-trifluoro-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin- 6(5H)-yl)ethan-1-one, (1-methyl-1H-pyrazol-4-yl)(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, 2-phenoxy-1-(2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)ethan-1-one, 2-(4-fluorophenoxy)-1-(2- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)ethan-1-one, 2-(phenylamino)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin- 6(5H)-yl)ethan-1-one, 2-((2-fluoropyridin-4-yl)oxy)-1-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)ethan-1-one, 3-(6-(methylsulfonyl)-4,5,6,7- tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 5-(trifluoromethyl)-3- (6-((trifluoromethyl)sulfonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-1,2,4-oxadiazole, 3-(6- (phenylsulfonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole, 3-(6-((4-fluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole, 3-(6-tosyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole, 3-(6-((4-methoxyphenyl)sulfonyl)-4,5,6,7- tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(6-((2,4- difluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole, 3-(6-((4-chlorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole, 3-(6-((3-fluorophenyl)sulfonyl)-4,5,6,7-tetrahydrothieno[2,3- c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(6-(m-tolylsulfonyl)-4,5,6,7- tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(6- (cyclopropylsulfonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole, N-methyl-2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridin-6(5H)-yl)acetamide, N-(cyclopropylmethyl)-2-oxo-2-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)acetamide, 2- oxo-N-phenyl-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin- 6(5H)-yl)acetamide, N-(4-fluorophenyl)-2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)acetamide, N-(3-fluorophenyl)-2-oxo-2-(2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)acetamide, N- (4-chlorophenyl)-2-oxo-2-(2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridin-6(5H)-yl)acetamide, phenyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7- dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate, p-tolyl 2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate, 4-fluorophenyl 2-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate, ethyl 2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate, (7- methyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)- yl)(phenyl)methanone, (4-fluorophenyl)(7-methyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, (4-chlorophenyl)(7-methyl-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, (4- methoxyphenyl)(7-methyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridin-6(5H)-yl)methanone, (2,4-difluorophenyl)(7-methyl-2-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, cyclopropyl(7-methyl-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl)methanone, (7- methyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)- yl)(pyridin-4-yl)methanone, 3-(7-methyl-6-(phenylsulfonyl)-4,5,6,7-tetrahydrothieno[2,3- c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(6-((4-fluorophenyl)sulfonyl)-7-methyl- 4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(7-methyl-6- (methylsulfonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole, 3-(7-methyl-6-((trifluoromethyl)sulfonyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2- yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, N,7-dimethyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide, N-(cyclopropylmethyl)-7-methyl-2-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide and 7-methyl-N-phenyl-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-4,7-dihydrothieno[2,3- c]pyridine-6(5H)-carboxamide. 6) A combination comprising the compound of formula (I) according to claim 1 and at least one further pesticidally active substance selected from the group consisting of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertilizers and nutrients. 7) An agrochemical composition comprising the compound of formula (I) according to claim 1 and at least one agrochemically acceptable auxiliary. 8) The composition according to claim 7, wherein said composition may further comprises at least one additional active ingredient. 9) The composition according to claim 7, wherein said composition is applied to seed and the amount of compound of formula (I) in a said composition ranges from 0.1 g a.i. to 10 kg a.i .per 100 kg of seeds. 10) A method for controlling or preventing phytopathogenic microorganisms, wherein the method comprises treating the fungi or the materials, plants, plant parts, locus thereof, soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of formula (I) according to claim 1 or the combination according to claim 6 or the composition according to claim 7. 11) A method for controlling or preventing infestations of plants by phytopathogenic microorganisms in agricultural crops and/or horticultural crops wherein an effective amount of at least one compound of formula (I) according to claim 1 or the combination according to claim 6 or the composition according to claim 7, is applied to the plants, to parts thereof or a locus thereof. 12) The method according to claim 11, wherein the phytopathogenic microorganisms are selected from the group comprising Hemileia vastatrix (Coffee rust), Uromyces appendiculatus/fabae/ phaseoli (rust of beans) Puccinia spp. (rusts) on various plants, from the group comprising P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. Hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals (wheat, barley or rye) and from the group comprising Phakopsora spp. on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans. 13) Use of a compound of formula (I) according to claim 1 as a fungicide. 14) Use of compound of formula (I) according to claim 1 or the combination according to claim 6 or the composition according to claim 7, for controlling or preventing agricultural crops and/or horticultural crops against phytopathogenic microorganisms. 15) The use of compounds of formula (I) according to claim 14, wherein phytopathogenic microorganisms are selected from Phakopsora pachyrhizi, Phakopsora meibomiae, of agricultural crops and/or horticultural crops. 16) Use of compounds of formula (I) according to claim 1, or compositions according to claim 6 or the composition according to claim 7, for controlling rust diseases of agricultural crops and/or horticultural crops. 17) The use of compounds of formula (I) according to claim 16, wherein said rust diseases of crops are Hemileia vastatrix (Coffee rust), Uromyces appendiculatus/fabae/ phaseoli (rust of beans) Puccinia spp. (rusts) on various plants selected from P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. Hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals selected from wheat, barley or rye and Phakopsora spp. on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans. 18) A seed comprising a compound of formula (I) according to claim 1, wherein the amount of the compound of formula (I) is from 0.1 g to 1 kg per 100 kg of seed.
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