WO2021090282A1 - Novel oxadiazole compounds containing fused heterocyclyl rings for controlling or preventing phytopathogenic fungi - Google Patents

Novel oxadiazole compounds containing fused heterocyclyl rings for controlling or preventing phytopathogenic fungi Download PDF

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Publication number
WO2021090282A1
WO2021090282A1 PCT/IB2020/060497 IB2020060497W WO2021090282A1 WO 2021090282 A1 WO2021090282 A1 WO 2021090282A1 IB 2020060497 W IB2020060497 W IB 2020060497W WO 2021090282 A1 WO2021090282 A1 WO 2021090282A1
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WIPO (PCT)
Prior art keywords
trifluoromethyl
oxadiazol
indol
methyl
ethyl
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PCT/IB2020/060497
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French (fr)
Inventor
Paras Raybhan BHUJADE
Maruti Nagappa NAIK
Yogesh Kashiram BELKAR
Santosh Shridhar AUTKAR
Ruchi GARG
Vishwanath GADE
Alexander G.M. KLAUSENER
Prashantha Mouli YOGAPPA
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Pi Industries Ltd.
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Publication of WO2021090282A1 publication Critical patent/WO2021090282A1/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles

Definitions

  • the present invention relates to novel oxadiazoles that are useful for combating phytopathogenic fungi, to a process for preparing such noveloxadiazoles and to a combination and a composition comprising these novel oxadiazoles.
  • the present invention also relates to a method for controlling or preventing phytopathogenic fungi.
  • ACKGROUND OF THE INVENTION Oxadiazoles are already known from literature.
  • the present invention relates to a compound of formula (I), Formula (I) wherein, R 1 , R 2 , R 3 , R 4 , A 1 and Q 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 a combination 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 control or prevent.
  • the present invention still further relates to a composition
  • a composition 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 the compounds of formula (I) as such, the combination or the composition thereof for controlling and or preventing plant diseases, particularly phytopathogenic fungi.
  • compositions comprising, “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.
  • 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.
  • 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’.
  • “or” refers to an inclusive “or” and not to an exclusive “or”.
  • 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).
  • the term “invertebrate pest” includes arthropods, gastropods and nematodes and helminths of economic importance as pests.
  • arthropod includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans.
  • gastropod includes snails, slugs and other Stylommatophora.
  • nematode refers to a living organism of the Phylum Nematoda.
  • helminths includes roundworms, heartworms, phytophagous nematodes (Nematoda), flukes (Tematoda), acanthocephala and tapeworms (Cestoda).
  • invertebrate pest control means inhibition of invertebrate pest development (including mortality, feeding reduction, and/or mating disruption), and related expressions are defined analogously.
  • 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, crucifers 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, crucifers and cucurbits
  • potatoes e.g., sweet potatoes, grapes, cotton, tree fruits (e.
  • 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, 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 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). Additionally, the person skilled in the art knows processes or methods or technology to separate, enrich, and/or to selectively prepare said isomers.
  • 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.
  • 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 -
  • 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 to C 24 alkenes, preferably C 2 to C 15 alkenes, more preferably C 2 to C 10 alkenes, most preferably C 2 to G, 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,
  • 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, l-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, 1- methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, l,l-dimethyl-2-propynyl, 1-ethyl -2- propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l-methyl-2-pentynyl, l-methyl-3- pentynyl, l-methyl-4-pentynyl, 2-methyl-3-p
  • 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. This definition also applies to cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere.
  • cycloalkoxy cycloalkenyloxy
  • cycloalkoxy cycloalkenyloxy
  • 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. 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.
  • 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 l,l,l-trifluoroprop-2-yl. This definition also applies to
  • haloalkenyl haloalkynyl
  • 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
  • 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
  • Non-limiting examples of “haloalkylsulfmyl” include CF 3 S(0), CC1 S(0), CFsCttStO) and CF 3 CF 2 S(0).
  • Non-limiting examples of “haloalkylsulfonyl” include CF 3 S(0) 2 , CCl 3 S(0) 2 , CF 3 CH 2 S(0) 2 and CF 3 CF 2 S(0) 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(0) 2 -
  • alkoxy used either alone or in compound words included C1 to C24 alkoxy, preferably C1 to C15 alkoxy, more preferably C1 to C10 alkoxy, most preferably C1 to Ce alkoxy.
  • 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- e
  • alkoxyalkyl denotes alkoxy substitution on alkyl.
  • alkoxyalkyl include CH3OCH2, CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2.
  • alkoxyalkoxy denotes 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-dimethylbutyl
  • Halocycloalkyl, halocycloalkenyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylcarbonyl, cycloalkylcarbonyl, haloalkoxylalkyl, and the like, are defined analogously to the above examples.
  • alkylthioalkyl denotes 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 alkylthio substitution on alkoxy.
  • cycloalkylalkylamino denotes cycloalkyl substitution on alkyl amino.
  • alkoxyalkoxyalkyl “alkylaminoalkyl”, “dialkylaminoalkyl”, “cycloalkylaminoalkyl”, “cycloalkylaminocarbonyl” and the like, are defined analogously to “alkylthioalkyl” or “cycloalkylalkylamino”.
  • 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.
  • alkoxycarbonylalkylamino denotes alkoxy carbonyl substitution on alkyl amino.
  • Alkylcarbonylalkylamino denotes 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-methylpentyls
  • arylsulfmyl 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-methylpentylsulfonyl,
  • arylsulfonyl includes Ar-S(0) 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 “aromatic carbocyclic ring system” and “non-aromatic carbocylic ring system” or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which 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 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 oxetanyl, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1- pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isox
  • heteroaryl or “aromatic heterocyclic” means 5 or 6-membered, fully unsaturated monocyclic ring system 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-ox
  • 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-l,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, l,3,5-triazin-2-yl, 1,2,4-triazin- 3-yl and l,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
  • 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.
  • haloalkylsufonylaminocarbonyl alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkyl amino and the like are defined analogously
  • C 1 -C 3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl
  • C 2 alkoxyalkyl designates CH 3 OCH 2
  • C 3 alkoxyalkyl designates, for example, CH3CH(OCH3), 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 .
  • all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
  • 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.
  • pest 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 the 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 use of human and animals.
  • plant parts is understood to mean all parts and organs of plants above and below the ground.
  • plant parts 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, auxiliary 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 compound of the present disclosure in a composition optionally comprising other compatible compounds to a plant or a plant material or locus thereof include application by a technique known to a person skilled in the art which include but is not limited to spraying, coating, dipping, fumigating, impregnating, injecting and dusting.
  • applied means adhered to a plant or plant part either physically or chemically including impregnation.
  • the present invention provides a novel oxadizole compound of formula (I), Formula (I) wherein, R 1 is C 1 -C 2 -haloalkyl; R 2 and R 3 are independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl, C 1- C 6 - haloalkoxy, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfinyl and C 1 - C 6 -alkylsulfonyl; R 2 and R 3 are optionally
  • R 10 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl;
  • R 11 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, -(CR 12 R 13 )0-4C3-C6-non-aromatic carbocyclyl ring, -(CR 12 R 13 )0-4C6-
  • the compound of formula (I) of the present invention is represented by a compound of formula (lb); wherein, R 1 , R 2 , R 3 , R 4 , R 7 , R 10 and R 11 are as defined in the above detailed description.
  • the compound of formula (I) of the present invention is represented by a compound of formula (Ic); wherein, R 1 , R 2 , R 3 , R 4 , R 7 , R 10 and R 11 are as defined in the above detailed description.
  • the compound of formula (I) of the present invention is represented by a compound of formula (Id);
  • the compound of formula (I) of the present invention is represented by a compound of formula (Ie);
  • the compound of formula (I) of the present invention is represented by a compound of formula (If);
  • the compound of formula (I) of the present invention is represented by a compound of formula (Ig);
  • the compound of formula (I) of the present invention is represented by a compound of formula (Ih); wherein, R 1 , R 2 , R 3 , R 4 , R 7 , R 10 and R 11 are as defined in the above detailed description.
  • the compound of formula (I) of the present invention is represented by a compound of formula (Ii); wherein, R 1 , R 2 , R 3 , R 4 , R 7 , R 10 and R 11 are as defined in the above detailed description.
  • the compound of formula (I) of the present invention is represented by a compound of formula (Ij); Formula (Ij) wherein, R 1 , R 2 , R 3 , R 4 , R 7 , R 10 and R 11 are as defined in the above detailed description.
  • the compound of formula (I) of the present invention is represented by a compound of formula (Ik);
  • 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 CI;
  • R 2 and R 3 are independently selected from the group consisting of hydrogen, halogen, cyano, C1-C6 alkyl, CYCYcycloalkyl, CYCYalkoxy, CYCYhaloalkyl and C1 CYhaloalkoxy;
  • a 1 is CR 7 ; and R 4 and R 7 are independently selected from the group consisting of hydrogen, halogen, C1-G.-alkyl, CYCYcycloalkyl, CYCYalkoxy and CYCYhaloalkyl;
  • R 11 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, CYCYcycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, CYCYcycloal kyl-C 1 -CYal kyl , C1-C6 alkoxy-C1-C6-alkyl, C1-C6-alkylsulfinyl, C 1 - C 6 - a 1 k y 1 s u 1 f o n y 1 , -(CR 12 R 13 ) 0-4 C 3 -C 6 -non-aromatic carbocyclyl ring, -(CR 12 R 13 ) 0-4 C6-C10-aromatic carbocyclyl ring, -(CR 12 R 13 ) 0-4 C 3 -C 6 -non-aro
  • R 14 is selected from the group consisting of hydrogen, C1- 6 -alkyl and C3 6 -cycloalkyl; R 11 may be optionally substituted with halogen, cyano, amino, C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino, C 1 -C 6 -trialkylamino, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkoxy and phenoxy, R 12 and R 13 are independently selected from the group consisting of hydrogen, halogen, methyl, ethyl and propyl.
  • the present invention provides a compound of formula (I) wherein, R 1 is selected from the group consisting of -CF3, -CHF2 and -CF2Cl; R 2 and R 3 are independently selected from the group consisting of hydrogen, halogen, cyano and C1- C 6 alkyl; A 1 is CR 7 ; and R 4 and R 7 are independently selected from the group consisting of hydrogen, halogen and C1-C6-alkyl; R 10 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6 alkoxy, and C1-C6-haloalkyl; R 11 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
  • R 1 is -CF3; R 2 and R 3 are independently selected from the group consisting of hydrogen and C1-C6 alkyl.
  • the compound of formula (I) is selected from ethyl 2-(5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetate, N-(3,4-difluorophenyl)-2-(5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-inol-1-yl)acetamide, 2-(5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)-N-(4-(trifluoromethyl)phenyl)acetamide, N-(2-fluorophenyl)-2-(5-(5- (trifluoromethyl)-1,2,4
  • the present invention provides a compound of formula (III) or salts thereof; Formula (III) wherein, R b is selected from the group consisting of hydrogen or –C 1 -C 4 -alkyl-NH-R 10 ; R 1 , R 2 , R 3 , R 4 , and A 1 are as defined in the detailed description.
  • the compounds of the present invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • the compound of the present invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.
  • An anion part of the salt in case the compound of formula (I) is a 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 an anionic or capable of forming an anion can be inorganic or organic.
  • examples of an inorganic anion part of the salt include but are not limited to chloride, bromide, iodide, fluoride, sulphate, phosphate, nitrate, nitrite, hydrogen carbonates, hydrogen sulphate.
  • organic anion part of the salt examples 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 an inorganic cation part of the salt include but are not limited to alkali and alkaline earth metals.
  • organic cation part of the salt examples include but are not limited to pyridine, methyl amine, imidazole, benzimidazole, hitidine, phosphazene, tetramethyl ammonium, tetrabutylammonium, choline and trimethylamine.
  • Metal ions in metal complexes of the compounds 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 group, 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.
  • Formula (I) thus includes all crystalline and non- crystalline forms of the compound 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 present invention provides a process for the synthesis of a compound of formula (I).
  • the process for the synthesis of compounds of formula (I) is comprising at least one of the following steps (a) to (k): a) reacting a compound of formula 2 with a hydroxyl amine to afford a compound of formula 4; wherein, R 2 or R 3 is not cyano; R 4 , Q and A 1 are as defined in the above detailed description; b) reacting the compound of formula 4 with a suitable carboxylic acid anhydride of formula 5a or suitable carboxylic acid chloride of formula 5b to afford a compound of formula (I); wherein, R 1 , R 2 , R 3 , R 4 , Q and A 1 are as defined in the above detailed description; c) reacting a compound of formula 6a with a compound of formula 7 to afford a compound of formula (I); wherein, Q is Q1; R is hydrogen or alkyl; R 1 , R 2 , R 3 , R 4 and A 1 are as defined in detailed description above; d) reacting a compound of formula 10 with a suitable
  • a suitable base such as sodium hydride, potassium carbonate, cesium carbonate, etc.
  • Step: 2 The compound of formula 2 is treated with hydroxylamine hydrochloride in the presence of a suitable base such as sodium bicarbonate or triethyl amine to obtain the compound of formula 4.
  • a suitable base such as sodium bicarbonate or triethyl amine
  • This reaction is typically carried out in a suitable solvent such as methanol, ethanol or tetrahydrofuran at a temperature ranging from 0-65 o C.
  • this reaction can also be carried out by reacting the compound of formula 2 with 50 % aqueous hydroxyl amine solution in a suitable solvent such as methanol, ethanol or tetrahydrofuran at a temperature ranging from 0-65 o C.
  • Step: 3 The compound of formula 6a can be prepared by reacting the compound of formula 4 with a suitable acid anhydride of formula 5a in a suitable solvent such as tetrahydrofuran or dichloromethane at a temperature ranging from 0-50 o C. Alternatively, this reaction can also be carried out by reacting compound of formula 4 with carboxylic acid chloride of formula 5b in the presence of a suitable solvent such as tetrahydrofuran, 2-methyl tetrahydrofuran, dichloromethane, etc. at temperature ranging from 0-100 o C.
  • Step: 4 The compound of formula 6a may then be treated with amine derivatives of formula 7 in the presence of trimethyl aluminum to obtain the compound of formula (I) wherein Q is Q1. This reaction is typically carried out in a suitable solvent such as toluene or tetrahydrofuran at a temperature ranging from 20-110 o C.
  • a suitable solvent such as toluene or tetrahydrofuran at
  • Step: 1 The compound of formula 8 can be prepared by reacting the compound of formula 7 with di-tert-butyl dicarbonate in the presence of a suitable base such as 4-dimethylaminopyridine in suitable solvent such as dichloromethane or tetrahydrofuran at a temperature ranging from 0-25 o C.
  • Step: 2 The compound of formula 9 can be prepared by reacting the compound of formula 8 with hydroxyl amine hydrochloride in the presence of a suitable base such as sodium bicarbonate or triethyl amine.
  • This reaction is generally carried out in a suitable solvent such as methanol, ethanol or tetrahydrofuran at a temperature ranging from 10-65 o C.
  • this reaction can also be carried out by reacting the compound of formula 8 with 50% aqueous hydroxyl amine solution in a suitable solvent such as methanol, ethanol or tetrahydrofuran at a temperature ranging from 10-65 o C.
  • Step: 3 The compound of formula 10 can be prepared by reacting the compound of formula 9 with an acid anhydride of formula 5a. This reaction is typically carried out in a suitable solvent such as tetrahydrofuran or dichloromethane at temperature ranging from 0-50 o C.
  • this reaction can also be carried out by reacting the compound of formula 9 with the carboxylic acid chloride of formula 5b in the presence of a suitable solvent such as tetrahydrofuran, 2- methyl tetrahydrofuran, dichloromethane, etc. at a temperature ranging from 0-100 o C.
  • a suitable solvent such as tetrahydrofuran, 2- methyl tetrahydrofuran, dichloromethane, etc.
  • the compound of formula 11 can be obtained by reacting the compound of formula 10 with a suitable acid such as trifluoroacetic acid or hydrochloric acid. This reaction is carried out in a suitable solvent such as dichloromethane or tetrahydrofuran at a temperature ranging from 0-25 o C.
  • Step: 5 The compound of formula (I) can be obtained by reacting the compound of formula 11 with a suitable acid chloride of formula 12 in the presence of an suitable organic base such as triethyl amine, diisopropyl ethyl amine or pyridine. This reaction is typically carried out in a suitable solvent such as dichloromethane and catalyst such as 4-dimethylaminopyridine at a temperature ranging from 0-25 o C.
  • the compound of formula 13 can be obtained by reacting the compound of formula 12 with the compound of formula 12a in the presence of a suitable base such as triethylamine, potassium carbonate, cesium carbonate, etc.
  • Step: 2 The compound of formula 14 can be obtained by reducing the compound of formula 13 in the presence of a suitable reducing agent such as iron/ammonium chloride in a suitable solvent such as methanol, water, ethanol etc or mixture therof.
  • Step: 3 The compound of formula 15 can be prepared by reacting the compound of formula 14 with the compound of formula 10f in the presence of suitable acid catalyst such as p-toluenesulfonic acid etc. This reaction is typically carried out in a suitable solvent such as ethanol, toluene, etc.
  • the compound of formula 16 can be obtained by reacting compound of formula 12 with the compound of formula 12a in the presence of a suitable base such as triethylamine, potassium carbonate, cesium carbonate, etc. This reaction is typically carried out in a suitable solvent such as N,N-dimethylformamide, dimethyl sulfoxide, etc. at a temperature ranging from 10-100 o C.
  • a suitable reducing agent such as iron/ammonium chloride in a suitable solvent such as methanol, water, ethanol etc or mixture therof.
  • the compound of formula 18b can be prepared by reacting the compound of formula 17 with the compound of formula 10f in the presence of a suitable acid catalyst such as p-toluenesulfonic acid etc. This reaction is typically carried out in a suitable solvent such as ethanol, toluene, etc. at a temperature ranging from 50-80 o C.
  • a suitable acid catalyst such as p-toluenesulfonic acid etc.
  • This reaction is typically carried out in a suitable solvent such as ethanol, toluene, etc. at a temperature ranging from 50-80 o C.
  • the compound of formula 19 can be prepared by reacting the compound of formula 18ab with hydroxyl amine hydrochloride in the presence of a suitable base such as sodium bicarbonate or triethyl amine. This reaction is generally carried out in a suitable solvent such as methanol, ethanol or tetrahydrofuran at a temperature ranging from 10-65 o C.
  • this reaction an also be carried out by reacting the compound of formula 18ab with a 50% aqueous hydroxyl amine solution in a suitable solvent such as methanol, ethanol or tetrahydrofuran at a temperature ranging from 10-65 o C.
  • a suitable solvent such as methanol, ethanol or tetrahydrofuran
  • Step: 2 The compound of formula 20 can be prepared by reacting the compound of formula 19 with an acid anhydride of formula 5a. This reaction is typically carried out in a suitable solvent such as tetrahydrofuran or dichloromethane at a temperature ranging from 0-50 o C.
  • this reaction can also be carried out by reacting the compound of formula 19 with carboxylic acid chloride of formula 5b in the presence of a suitable solvent such as tetrahydrofuran, 2- methyl tetrahydrofuran, dichloromethane, etc. at a temperature ranging from 0-100 o C.
  • a suitable solvent such as tetrahydrofuran, 2- methyl tetrahydrofuran, dichloromethane, etc.
  • the compound of formula 21 can be obtained by deprotecting the compound of formula 20 with a suitable deprotecting reagents such as hydrochloric acid in a suitable solvent such as dichloromethane, tetrahydrofuran, 1,4-dioxane etc. at ambient temperature.
  • Step: 4 The compound of formula (I) wherein Q is Q 2 can be prepared by reacting the compound of formula 21 with a suitable acid chloride of formula 15a in the presence of base such as triethylamine, diisopropylethylamine, etc. This reaction is typically carried out in a suitable aprotic solvent such as 2-methylterahydrofuran, tetrahydrofuran, dichloromethane, etc. at a temperature ranging from 0-30 o C.
  • base such as triethylamine, diisopropylethylamine, etc.
  • a suitable aprotic solvent such as 2-methylterahydrofuran, tetrahydrofuran, dichloromethane, etc.
  • the compound of formula (I) can be prepared by reacting a carboxylic acid compound of formula 15b in the presence of an amide coupling reagent such as 1-Ethyl-3-(3- dimethylaminopropyl)carbodiimide (EDCl), hydroxybenzotriazole (HOBt), 1- [Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), etc.
  • an amide coupling reagent such as 1-Ethyl-3-(3- dimethylaminopropyl)carbodiimide (EDCl), hydroxybenzotriazole (HOBt), 1- [Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), etc.
  • This reaction is carried out in the presence of a base such as triethylamine, diisopropylethylamine in aprotic solvents such as dichloromethane, tetrahydrofuran, dimethyl formamide etc. This reaction can be carried out at a temperature ranging from 0-60 °C.
  • a base such as triethylamine, diisopropylethylamine in aprotic solvents such as dichloromethane, tetrahydrofuran, dimethyl formamide etc.
  • This reaction can be carried out at a temperature ranging from 0-60 °C.
  • the compound of formula 23 can be obtained by reacting the compound of formula 22 with a compound of formula 10e in the presence of a suitable base such as sodium bicarbonate, potassium carbonate or cesium carbonate. This reaction is typically carried out in a suitable aprotic solvent such as N,N-dimethylformamide, dimethyl sulfoxide, etc. at a temperature
  • the compound of formula 25 can be prepared by reacting the compound of formula 23 with the compound of formula 10f in the presence of a suitable acid catalyst such as p-toluenesulfonic acid etc. This reaction is typically carried out in solvents such as ethanol, toluene, etc. at a temperature ranging from 50-80 o C.
  • a suitable acid catalyst such as p-toluenesulfonic acid etc. This reaction is typically carried out in solvents such as ethanol, toluene, etc. at a temperature ranging from 50-80 o C.
  • Step: 3 The compound of formula 26a can be prepared by cyanation of the compound of formula 25 in the presence of a suitable cyanide source such as potassium hexacyanoferrate(II) trihydrate and a suitable catalyst such as Pd(Xanphos)allylCl in the presence of potassium acetate as reported in J. Org. Chem. 2018, 83, 4922 ⁇ 4931.
  • this reaction can also be carried out in the presence of potassium hexacyanoferrate(II) trihydrate, palladium (II) diacetate and sodium bicarbonate in 1,4-dioxane as described in Organometallics, 2015, vol.34 (10), p.1942 – 1956.
  • General scheme: 7 The compound of formula 28 can be obtained by reacting the compound of formula 27 with the compound of formula 10e in the presence of a suitable base such as sodium bicarbonate, potassium carbonate or cesium carbonate. This reaction is typically carried out in a suitable aprotic solvent such as N,N-dimethylformamide, dimethyl sulfoxide, etc.
  • the compound of formula 26b can be obtained by reacting the compound of formula 28 with the compound of formula 10f in the presence of a suitable acid catalyst such as p-toluenesulfonic acid etc. This reaction is typically carried out in a suitable solvent such as ethanol, toluene, etc. at a temperature ranging from 50-80 o C.
  • a suitable acid catalyst such as p-toluenesulfonic acid etc.
  • This reaction is typically carried out in a suitable solvent such as ethanol, toluene, etc. at a temperature ranging from 50-80 o C.
  • the compound of formula 30 can be prepared by reacting the compound of formula 26ab with hydroxyl amine hydrochloride in the presence of a suitable base such as sodium bicarbonate or triethyl amine.
  • This reaction is generally carried out in a suitable solvent such as methanol, ethanol or tetrahydrofuran at a temperature ranging from 10-65 o C.
  • this reaction can also be carried out by reacting the compound of formula 26ab with a 50% aqueous hydroxyl amine solution in a suitable solvent such as methanol, ethanol or tetrahydrofuran at a temperature ranging from 10-65 o C.
  • Step: 2 The compound of formula 6b can be prepared by reacting the compound of formula 30 with a suitable acid anhydride of formula 5a. This reaction is typically carried out in a suitable solvent such as tetrahydrofuran or dichloromethane at a temperature ranging from 0-50 o C.
  • this reaction can also be carried out by reacting the compound of formula 30 with carboxylic acid chloride of formula 5b in the presence of a suitable solvent such as tetrahydrofuran, 2- methyl tetrahydrofuran, dichloromethane, etc. at a temperature ranging from 0-100 o C.
  • a suitable solvent such as tetrahydrofuran, 2- methyl tetrahydrofuran, dichloromethane, etc.
  • the compound of formula 6c can be obtained by hydrolyzing the compound of formula 6b in the presence of a suitable acid such as trifluoroacetic acid in a suitable solvent such as dichloromethane at ambient temperature.
  • Step: 4 The compound of formula (I) wherein Q is Q 1 can be obtained by reacting the compound of formula 6c with the compound of formula 7 in the presence of a suitable amide coupling reagent such as 1- Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCl), hydroxybenzotriazole (HOBt), 1- [Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), etc.
  • a suitable amide coupling reagent such as 1- Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCl), hydroxybenzotriazole (HOBt), 1- [Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), etc.
  • the compound of formula (I) wherein Q is Q 8 can be prepared by reacting the compound of formula 21 with an isocyanate compound of formula 10b in the presence of a suitable base such as triethylamine, N,N-diisopropylethylamine in a suitable aprotic solvents such as dichloromethane, tetrahydrofuran, etc. at ambient temperature.
  • a suitable base such as triethylamine, N,N-diisopropylethylamine
  • a suitable aprotic solvents such as dichloromethane, tetrahydrofuran, etc. at ambient temperature.
  • the compound of formula (I) wherein Q is Q 8 can also be prepared by reacting the compound of formula 21 with an amine compound of formula 10a in the presence of triphosgene or phosgene.
  • the compound of formula (I) wherein Q is Q 9 can be prepared by reacting the compound of formula 21 with the compound of formula 10d in the presence of triphosgene or phosgene. This reaction is typically carried out in the presence of a suitable base such as triethylamine, N,N-diisopropylethylamine in a suitable aprotic solvent such as dichloromethane, tetrahydrofuran, etc. at ambient, higher or lower temperature.
  • a suitable base such as triethylamine, N,N-diisopropylethylamine
  • a suitable aprotic solvent such as dichloromethane, tetrahydrofuran, etc.
  • the compound of formula (I) wherein Q is Q 10 can be obtained by reacting the compound of formula 6c with a sulfoximine compound of formula 7a in the presence of a suitable coupling reagent such as 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCl), 4-dimethylaminopyridine (DMAP), 1- [Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), etc.
  • a suitable coupling reagent such as 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCl), 4-dimethylaminopyridine (DMAP), 1- [Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU
  • the present invention relates to a composition
  • a composition comprising the compound of formula (I), 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 ingredient with the auxiliary such as inert carrier or any other essential ingredient such as surfactants, additives, solid diluents and liquid diluents.
  • the compound of formula (I) and the composition 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 compound of formula (I) and the composition 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 present invention also includes a composition 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 compound of Formula I and composition 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.
  • treatment of plant propagation materials with the compound 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; rice, corn, cotton, fruits, coffee, sugarcane and soybeans.
  • cultiva 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.
  • auxin herbicides such as dicamba or 2,4-D
  • bleacher herbicides such as hydroxylphenylpyruvate dioxygena
  • 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 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 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
  • 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 controlling or preventing 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 controlling or preventing 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.
  • Albugo spp. white rust
  • vegetables e. g. A. Candida
  • sunflowers e. g. A. tragopogonis
  • Altemaria spp. Alternaria leaf spot
  • rape A. brass
  • 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 disease 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
  • 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 controlling or preventing 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
  • P. triticina brown or leaf rust
  • P. striiformis stripe or yellow rust
  • P. hordei dwarf rust
  • the present invention further relates to the use of the compounds of Formula I, the combinations or the compositions thereof for controlling or preventing against phytopathogenic fungi such as Phakopsora pachyrhizi, Phakopsora meibomiae, of agricultural crops and or horticultural crops.
  • the compound of Formula I, the combination and the composition thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials.
  • 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 provides a method for controlling or preventing phytopathogenic fungi, wherein said 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 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 to 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 compound 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 compound of Formula I are employed as such or in the form of composition 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 substances.
  • 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 present invention provides an agrochemical composition 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 compound 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. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • agrochemical compositions e. g. 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. g.
  • EW, EO, ES, ME capsules
  • 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
  • gel Formulations for the treatment of plant propagation materials such as seeds (e. g. GF).
  • 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 are 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, tetrahydronaphthalene, al
  • 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 mineral earths, e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulphate, magnesium sulphate, magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers, e. g.
  • Suitable surfactants are surface-active compounds, 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.
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulphates, 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 sulphates are sulphates 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 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 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 home- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.
  • Suitable cationic surfactants are 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 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 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 compound 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 polysaccharides (e. g.
  • xanthan gum carboxymethyl cellulose
  • inorganic clays organic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants e. g. in red, blue, or green
  • examples are inorganic colorants (e. g.
  • Suitable tackifiers or binders are 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 organic solvent (e. g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion.
  • Emulsifiable concentrates EC 15-70 wt% of a compound of Formula I and 5-10 wt% emulsifiers (e. g.
  • 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 addition of 1-5 wt% dispersants (e. g. sodium lignosulfonate), 1-3 wt% wetting agents (e. g. alcohol ethoxylate) and 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
  • solid carrier e. g. silica gel
  • Microcapsules An oil phase comprising 5-50 wt% of a compound of Formula I, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt% 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
  • an oil phase comprising 5-50 wt% of a compound of Formula I according to the invention, 0-40 wt% 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 monomers amount to 1-10 wt%.
  • the wt% relate 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 solid carrier (e. g. finely divided kaolin) ad 100 wt%.
  • solid carrier e. g. finely divided kaolin
  • Granules GR, FG
  • solid carrier e. g. silicate
  • Granulation is achieved by extrusion, spray-drying or fluidized bed.
  • Ultra-low volume liquids UL 1-50 wt% of a compound of Formula I are dissolved in organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%.
  • 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 of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • 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. Application can be carried out before or during sowing.
  • Methods for applying the compound of Formula I, the combination and the composition thereof, respectively, are application onto plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods.
  • the compound of Formula I, the combination and the composition thereof, respectively are applied on to the plant propagation material by a method such that 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 0.05 to 1 kg per ha, more preferably from 0.1 to 1.0 kg per ha.
  • plant propagation materials such as seeds, e. g.
  • amounts of active substance 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) are generally required.
  • 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 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides e. g.
  • herbicides insecticides, fungicides, growth regulators, safeners, biopesticides
  • active substances may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (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 a 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 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.
  • the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the 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 thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • 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.
  • 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 compound of formula (I), the combination and the composition 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 provides a combination comprising at least one compound of formula (I) and at least one further pesticidally active substance 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 compound of formula (I).
  • the 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 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 compound 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 to ensure 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 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 on 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 inventive mixtures applied by seed treatment.
  • the invention disclosed in the present disclosure shall now be elaborated with the help of non-limiting examples.
  • Step 2 Ethyl 2-(5-(N’-hydroxycarbamimidoyl)-1H-indol-1-yl)acetate
  • ethyl 2-(5-cyano-1H-indol-1-yl)acetate 8 g, 35 mmol
  • hydroxylamine hydrochloride 3.6 g, 53 mmol
  • sodium bicarbonate 4.7 g, 56 mmol
  • the resulting reaction mixture was stirred at 55 °C for 16 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and filtered. The obtained solid was washed with ethanol (100 mL).
  • reaction mixture was poured slowly into a mixture of ethyl acetate (200 mL), sodium bicarbonate (20 g) and ice cold water (300 mL).
  • ethyl acetate layer was isolated, washed twice with saturated sodium bicarbonate solution (60 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude product.
  • the obtained crude product was purified by column chromatography on silica gel using ethyl acetate in hexane as an eluent to obtain ethyl 2-(5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetate (4.5 g, 38 % yield).
  • Step 4 N-(3,4-difluorophenyl)-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)acetamide
  • ethyl 2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetate 0.2 g, 0.59 mmol
  • 3,4-difluoroaniline 0.15 g, 1.18 mmol
  • 2M trimethylaluminium toluene (0.74 mL, 1.47 mmol
  • reaction mixture was cooled to 25 °C and poured into a solution of 10 % aqueous acetic acid (7 mL) and ethyl acetate (15 mL). The resulting mixture was further stirred at 25 °C for 10 minutes. The ethyl acetate layer was isolated and the aqueous layer was again extracted with ethyl acetate (20 mL). The combined ethyl acetate layer was washed with water (20 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude product.
  • Boc-anhydride (19.6 mL, 84 mmol) was added drop wise at 0-5 °C, and the resulting reaction mixture was stirred at 25 °C for 4 h. After completion of the reaction, the product was extracted twice into ethyl acetate (200 mL). The combined ethyl acetate layer was washed twice with brine solution (100 mL), dried over anhydrous sodium sulphate, filtered and concentrated to obtain tert-butyl 5-cyano-1H-indole-1-carboxylate (16.5 g, 97 % yield).
  • Step 3 Tert-butyl 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indole-1-carboxylate (Compound no.10) To a stirred solution of tert-butyl 5-(N’-hydroxycarbamimidoyl)-1H-indole-1-carboxylate (19 g, 68 mmol) in tetrahydrofuran (150 mL), trifluoroacetic anhydride (14.4 mL, 102 mmol) was added at 0-5 °C, and the resulting reaction mixture was stirred at 25 °C for 18 h.
  • reaction mixture was poured into aqueous saturated sodium bicarbonate solution (400 mL) at 10 o C.
  • the suspension was filtered, washed with water (100 mL) followed by hexane (50 mL) and dried under reduced pressure to obtain tert-butyl 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indole-1- carboxylate (23 g, 64 mmol, 94 % yield).
  • reaction mixture was heated under stirring to 120 o C for 4 h. After completion of the reaction, the reaction mixture was cooled to 25 o C, water (200 mL) was added and the reaction mixture was filtered. The obtained solid was washed with water (50 mL) and dried to obtain tert-butyl (2-((5-cyano-2-nitrophenyl)amino)ethyl)carbamate (9.2 g, 100 % yield) as a yellow solid.
  • Step 2 tert-butyl (2-((2-amino-5-cyanophenyl)amino)ethyl)carbamate
  • tert-butyl (2-((5-cyano-2-nitrophenyl)amino)ethyl)carbamate 5 g, 16.3 mmol
  • iron 3.65 g, 65.3 mmol
  • ammonium chloride 5.24 g, 98 mmol
  • reaction mixture was filtered through celite and washed with methanol (100 mL). The filtrate was diluted with dichloromethane (200 mL) and sodium bicarbonate solution (50 mL). The organic layer was separated, washed with water (100 mL) and brine solution (50 mL). The organic layer was concentrated under reduced pressure to obtain tert-butyl (2-((2-amino-5- cyanophenyl)amino)ethyl)carbamate (4.28 g, 95 % yield) as brown solid.
  • Step 3 tert-butyl (2-(6-cyano-1H-benzo[d]imidazol-1-yl)ethyl)carbamate
  • tert-butyl (2-((2-amino-5-cyanophenyl)amino)ethyl)carbamate (4.28 g, 15.5 mmol) in ethanol (40 mL)
  • triethyl orthoformate 5.16 ml, 31.0 mmol
  • p-toluenesulfonic acid monohydrate 0.884 g, 4.6 mmol
  • reaction mixture was cooled to 25 o C.
  • Water (200 mL) and dichloromethane (100 mL) were added, followed by the addition of saturated sodium bicarbonate solution (50 mL).
  • the organic layer was separated, washed with water (50 mL), saturated sodium bicarbonate solution (50 mL) and brine solution (50 mL).
  • the organic layer was separated, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain tert-butyl (2-(6-cyano- 1H-benzo[d]imidazol-1-yl)ethyl)carbamate (3.6 g, 81 % yield) as solid.
  • Step 4 tert-butyl (2-(6-(N'-hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1- yl)ethyl)carbamate
  • aqueous hydroxylamine solution 4.3 mL, 69.8 mmol
  • reaction mixture was allowed to stir at 25 o C for 16 h. After completion of the reaction, the reaction mixture was quenched by addition of ice cold water (100 mL) and extracted with dichloromethane (200 mL). The organic layer was separated and washed with saturated sodium bicarbonate solution (50 mL), water (100 mL) and brine solution (50 mL).
  • Step 7 N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)isobutyramide (compound no 36)
  • 2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethan-1-amine hydrochloride (0.15 g, 0.4 mmol) in dichloromethane (5 mL)
  • triethyl amine (0.157 mL, 1.124 mmol
  • N,N-dimethylpyridin-4-amine 5.49 mg, 0.04 mmol
  • Example 4 Preparation of 1-(4-chlorophenyl)-3-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-benzo[d]imidazol-1-yl)ethyl)urea (compound no.64)
  • 2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethan-1-amine hydrochloride (0.15 g, 0.5 mmol) in dichloromethane (3.0 mL)
  • triethyl amine 0.063 mL, 0.5 mmol
  • 1-chloro-4-isocyanatobenzene 0.055 mL, 0.5 mmol
  • dichloromethane 2 0-5 o C during about 20 min under nitrogen atmosphere.
  • reaction mixture was stirred at 0 °C for 1 h. After completion of the reaction, the reaction mixture was quenched by drop wise addition of cyclopentanol (2 mL) at 0 °C, and the mixture was allowed to warm up from 0 °C to 25 °C under stirring during 30 min.
  • the reaction mixture was concentrated and purified by preparative HPLC to obtain cyclopentyl (2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)carbamate (0.043 g, 23 % yield) as a white solid.
  • Example 7 Preparation of N-phenyl-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)acetamide (compound no.48) a) Step 1: tert-Butyl-(2-amino-5-cyanophenyl)glycinate To a stirred solution of 3,4-diaminobenzonitrile (10 g, 75 mmol) in N,N-dimethylformamide (50 mL)), cesium carbonate (24.47 g, 7 mmol) was added, and stirring was continued at 25 °C for 1 h.
  • tert-Butyl-2-bromoacetate (12.12 mL, 8 mmol) was added, and the resulting reaction micture was stirred at 25 °C for 18 h. After completion of the reaction, the reaction mixture was diluted with dichloromethane (100 mL), washed twice with water (100 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude product. The obtained crude product was purified by flash column chromatography to get pure tert-butyl-(2-amino-5-cyanophenyl)glycinate (12.07 g, 65 % yield).
  • Step 2 tert-Butyl-2-(6-cyano-1H-benzo[d]imidazol-1-yl)acetate
  • tert-butyl-(2-amino-5-cyanophenyl)glycinate 10.5 g, 42.5 mmol
  • ethanol 50 mL
  • triethyl orthoformate 14.14 mL, 8 mmol
  • p-toluenesulfonic acid monohydrate 0.808 g, 4.3 mmol
  • the reaction mixture was cooled to 25 °C, diluted with dichloromethane (100 mL) and washed with saturated sodium bicarbonate solution (100 mL), then dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude product.
  • the obtained crude product was washed with diethyl ether to get tert-butyl-2-(6-cyano-1H-benzo[d]imidazol-1-yl)acetate (10.05 g, 39.1 mmol, 92% yield).
  • Step 3 tert-Butyl-2-(6-(N'-hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1-yl)acetate
  • tert-butyl-2-(6-cyano-1H-benzo[d]imidazol-1-yl)acetate 8.8 g, 34.2 mmol
  • hydroxylamine solution 50 wt.% in water 7.91 mL, 120 mmol
  • Step 4 tert-Butyl-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)acetate (compound no.26)
  • tert-butyl-2-(6-(N'-hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1-yl)acetate 9.9 g, 34.1 mmol
  • 2,2,2-trifluoroacetic anhydride (8.54 mL, 61.4 mmol) was added slowly at 0-5 °C under nitrogen atmosphere, and the resulting mixture was stirred for 18 h at 25 °C.
  • Example 8 Preparation of N-Phenyl-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)acetamide (compound no.90): a) Step 1: tert-Butyl-(2-amino-4-bromophenyl)glycinate tert-Butyl-(2-amino-4-bromophenyl)glycinate was synthesized by using similar experimental procedure of step-1 of example 1 (2.71 g, 21 % yield).
  • Step 2 tert-Butyl-2-(5-bromo-1H-benzo[d]imidazol-1-yl)acetate
  • tert-Butyl-2-(5-bromo-1H-benzo[d]imidazol-1-yl)acetate was synthesized by using similar experimental procedure of step-1 of example 1 (4.2 g, 81 % yield).
  • Step 3 tert-Butyl-2-(5-cyano-1H-benzo[d]imidazol-1-yl)acetate
  • tert-butyl 2-(5-bromo-1H-benzo[d]imidazol-1-yl)acetate 3.5 g, 11.3 mmol
  • Pd(Xanphos)allylCl 0.08 g, 0.6 mmol
  • potassium acetate 0.552 g, 5.6 mmol
  • potassium hexacyanoferrate(II) trihydrate 2.61 g, 6.2 mmol
  • Step 4 tert-Butyl-2-(5-(N'-hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1-yl)acetate
  • tert-Butyl-2-(5-(N'-hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1-yl)acetate was synthesized by using similar experimental procedure of step-1 of example 1 (2.54 g, 81 % yield).
  • Step 5 tert-Butyl-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)acetate (compound no.58) tert-Butyl-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetate was synthesized by using similar experimental procedure of step-1 of example 1 (3.1 g, 87 % yield).
  • Step 7 N-Phenyl-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)acetamide (compound no.90) N-Phenyl-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetamide was synthesized by using similar experimental procedure of step-1 of example 1 (0.088 g, 28 % yield).
  • Example 9 Preparation of N-(2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)nicotinamide (compound 94) a) Step 1: tert-butyl (2-((4-cyano-2-nitrophenyl)amino)ethyl)carbamate To a stirred solution of 4-fluoro-3-nitrobenzonitrile (8 g, 48.2 mmol) in dimethylsufoxide (80 mL), N- 1-Boc-1,2-diaminoethane (10.03 mL, 62.6 mmol) was added at 25 o C followed by addition of triethylamine (10.07 mL, 72.2 mmol) at 25 o C.
  • the resulting reaction mixture was heated to 120 o C for 4 h.
  • the reaction mixture was cooled to 25 o C and water (200 mL) was added slowly with stirring.
  • the obtained precipitate was filtered, washed with water (50 mL) and suction dried to obtain tert- butyl (2-((4-cyano-2-nitrophenyl)amino)ethyl)carbamate (13 g, 88 % yield).
  • Step 2 tert-butyl (2-((2-amino-4-cyanophenyl)amino)ethyl)carbamate
  • tert-butyl (2-((4-cyano-2-nitrophenyl)amino)ethyl)carbamate 10 g, 32.6 mmol
  • iron (7.29 g, 131 mmol) and ammonium hydrochloride (10.48 g, 196 mmol) were added at 25 o C.
  • the resulting reaction mixture was stirred at 70 o C for 4 h.
  • the reaction mixture was cooled to 25 o C, filtered through celite bed and washed with methanol (20 mL).
  • the dichloromethane (100 mL) was added to the obtained filtrate and stirred at 25 oC for 10 min.
  • the dichloromethane layer are isolated, washed with brine (20 mL) and concentrated to obtain tert-butyl (2-((2-amino-4-cyanophenyl)amino)ethyl)carbamate (8 g, 89 % yield).
  • Step 3 tert-butyl (2-(5-cyano-1H-benzo[d]imidazol-1-yl)ethyl)carbamate
  • tert-butyl (2-((2-amino-4-cyanophenyl)amino)ethyl)carbamate 11.5 g, 41.6 mmol
  • triethyl orthoformate 10.39 mL, 62.4 mmol
  • p-toluenesulfonic acid monohydrate 1.583 g, 8.32 mmol
  • the reaction mixture was cooled to 25 o C, dichloromethane (40 mL) and aqueous saturated sodium bicarbonate solution (45 mL) were added.
  • the dichloromethane layer was separated, washed with water (15 mL), aqueous saturated sodium bicarbonate solution (10 mL) and brine (10 mL).
  • the dichloromethane layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain tert-butyl (2-(5-cyano-1H-benzo[d]imidazol-1-yl)ethyl)carbamate (10 g, 84 % yield).
  • Step 4 tert-butyl (2-(5-(N'-hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1- yl)ethyl)carbamate
  • tert-butyl (2-(6-cyano-1H-benzo[d]imidazol-1-yl)ethyl)carbamate 7.5 g, 26.2 mmol
  • 50 % aqueous hydroxylamine solution (8.03 mL, 131 mmol) was added under nitrogen atmosphere.
  • the resulting reaction mixture was stirred at 65 o C for 5 h.
  • Step 5 tert-butyl (2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)carbamate
  • tert-butyl (2-(6-(N'-hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1- yl)ethyl)carbamate 7.5 g, 23.48 mmol
  • trifluoroacetic acid 5.97 mL, 42.3 mmol
  • the reaction mixture was poured into a mixture of ice cold water (20 mL) and dichloromethane (30 mL). The dichloromethane layer was isolated, washed with aqueous saturated sodium bicarbonate solution (15 mL), water (20 mL) and brine (20 mL). The dichloromethane layer was dried over sodium sulphate and concentrated under reduced pressure to obtain tert-butyl (2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)carbamate (5 g, 54 % yield).
  • BIOLOGY EXAMPLES Green House Test Example 1: Phakopsora pachyrhizi test in Soybean Compounds were dissolved in 2 % dimethyl sulfoxide/Acetone and then diluted with water containing emulsifier to the desired test concentration. To test the preventive activity of compounds, healthy young soybean plants, raised in the greenhouse, were sprayed with the active compound solution at the stated application rates inside spray cabinets using hallowcone nozzles. One day after treatment, the plants were inoculated with a suspension containing 2.1x10 6 Phakopsora pachyrhizi spores. The inoculated plants were then kept in the greenhouse chamber at 25 o C temperature and 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 compounds 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 compatibility by recording symptoms like necrosis, chlorosis and stunting. Compounds 1 2 3 4 6 7 8 9 10 11 12 13 14 15 16 17 18 19 21 22 23 24 26 28 29 31 37 38 40 42 43 44 45 46 47 48 49 57 59 showed >70 % at 500 ppm control in these tests when compared to the untreated check which showed extensive disease development.

Abstract

The present invention discloses a compound of formula (I), wherein, R1, R2, R3, R4, A1 and Q are as defined in the detailed description and a process for preparing the compound of formula (I). The present invention also discloses a method for controlling or preventing phytopathogenic fungi.

Description

PI E ternal TITLE OF THE INVENTION: NOVEL OXADIAZOLE COMPOUNDS CONTAINING FUSED HETEROCYCLYL RINGS FOR CONTROLLING OR PREVENTING PHYTOPATHOGENIC FUNGI FIELD OF THE INVENTION: The present invention relates to novel oxadiazoles that are useful for combating phytopathogenic fungi, to a process for preparing such noveloxadiazoles and to a combination and a composition comprising these novel oxadiazoles. The present invention also relates to a method for controlling or preventing phytopathogenic fungi. ACKGROUND OF THE INVENTION: Oxadiazoles are already known from literature. For example, in WO2019155066, WO2018210660, WO2018210658 and WO2017110863 various oxadiazoles have been disclosed. The oxadiazole compounds reported in the above cited literature have disadvantages in certain aspects, such as that they exhibit a narrow spectrum of efficacy or they do not have satisfactory fungicidal activity, particularly at low application rates. 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 using a compound of formula (I) of the present invention for controlling or preventing phytopathogenic fungi. SUMMARY OF THE INVENTION: The present invention relates to a compound of formula (I), Formula (I) wherein, R1, R2, R3, R4, A1 and Q 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 a combination 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 control or prevent.
The present invention still further relates to a composition 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 the compounds of formula (I) as such, the combination or the composition thereof for controlling and or preventing 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.
As referred to in this disclosure, the term “invertebrate pest” includes arthropods, gastropods and nematodes and helminths of economic importance as pests. The term “arthropod” includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans. The term “gastropod” includes snails, slugs and other Stylommatophora. The term “nematode” refers to a living organism of the Phylum Nematoda. The term “helminths” includes roundworms, heartworms, phytophagous nematodes (Nematoda), flukes (Tematoda), acanthocephala and tapeworms (Cestoda).
In the context of this disclosure “invertebrate pest control” means inhibition of invertebrate pest development (including mortality, feeding reduction, and/or mating disruption), and related expressions are defined analogously.
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, crucifers 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, 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 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, the person skilled in the art knows processes or methods or technology to separate, enrich, and/or to selectively prepare said isomers.
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.
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 C to C24 alkenes, preferably C2 to C15 alkenes, more preferably C2 to C10 alkenes, most preferably C2 to G, 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, l-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1- methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, l-methyl-4- pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, l,l-dimethyl-2-butenyl, l,l-dimethyl-3-butenyl, 1 ,2-dimethyl-l-butenyl, l,2-dimethyl-2-butenyl, l,2-dimethyl-3-butenyl, 1,3- dimethyl- 1-butenyl, l,3-dimethyl-2-butenyl, l,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, l-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, l-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, l-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, 1- methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, l,l-dimethyl-2-propynyl, 1-ethyl -2- propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l-methyl-2-pentynyl, l-methyl-3- pentynyl, l-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, l,l-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, 1- ethyl-3-butynyl, 2-ethyl-3-butynyl and l-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 l,l,l-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 “haloalkylsulfmyl” include CF3S(0), CC1 S(0), CFsCttStO) and CF3CF2S(0). Non-limiting examples of “haloalkylsulfonyl” include CF3S(0)2, CCl3S(0)2, CF3CH2S(0)2 and CF3CF2S(0)2.
The term “hydroxy” means -OH, Amino means -NRR, wherein R can be H or any possible substituent such as alkyl. Carbonyl means -C(=0)-, carbonyloxy means -OC(=0)-, sulfinyl means SO, sulfonyl means S(0)2-
The term “alkoxy” used either alone or in compound words included C1 to C24 alkoxy, preferably C1 to C15 alkoxy, more preferably C1 to C10 alkoxy, most preferably C1 to Ce 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 alkoxy substitution on alkyl. Non-limiting examples of “alkoxyalkyl” include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2.
The term “alkoxyalkoxy” denotes 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 alkylthio substitution on alkyl. Non-limiting examples of “alkylthioalkyl” include -CH2SCH2, -CH2SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and CH3CH2SCH2CH2. “Alkylthioalkoxy” denotes alkylthio substitution on alkoxy. The term “cycloalkylalkylamino” denotes 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 alkoxy carbonyl substitution on alkyl amino. “Alkylcarbonylalkylamino” denotes 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 l-ethyl-2-methylpropylsulphinyl and the different isomers. The term “arylsulfmyl” 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(0)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 “aromatic carbocyclic ring system” and “non-aromatic carbocylic ring system” or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which 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 “aromatic heterocycle or heteroaryl ring system” and “non-aromatic heterocycle ring system” or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which ring may be aromatic or non-aromatic, wherein the heterocycle ring contains at least one heteroatom selected from N, O, S(0)o -2, and or C ring member of the heterocycle may be replaced by C(=0), C(=S), C(=CR*R*) and C=NR*, * indicates integers.
The term “non-aromatic heterocycle” or “non-aromatic heterocyclic” means 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 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, l,2,4-oxadiazolidin-5-yl, l,2,4-thiadiazolidin-3-yl, l,2,4-thiadiazolidin-5-yl, 1,2,4- triazolidin-l-yl, l,2,4-triazolidin-3-yl, l,3,4-oxadiazolidin-2-yl, l,3,4-thiadiazolidin-2-yl, 1,3,4- triazolidin-l-yl, l,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, l,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2- tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4- hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, l,3,5-hexahydrotriazin-2-yl, 1,2,4- hexahydrotriazin-3-yl, cycloserines, 2,3,4,5-tetrahydro[lH]azepin-l- 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[lH]azepin-l- or -2- or -3- or -4- or -5- or -6- or-7- yl, 2,3,6,7-tetrahydro[lH]azepin-l- 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[l H]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, 2,3,4,7-tetrahydro[lH]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, 2,3,6,7-tetrahydro[lH]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-l,4-diazepinyl, tetra- and hexahydro-l,3-oxazepinyl, tetra- and hexahydro-l,4-oxazepinyl, tetra- and hexahydro-l,3-dioxepinyl, tetra- and hexahydro-l,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 system 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-l,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, l,3,5-triazin-2-yl, 1,2,4-triazin- 3-yl and l,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, 1-benzofuran- 5-yl, 1-benzofuran- 6-yl, l-benzofuran-7-yl, l-benzothiophen-2-yl, l-benzothiophen-3-yl, 1- 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, l,3-benzothiazol-5-yl, l,3-benzothiazol-6-yl, 1,3- benzothiazol-7-yl, l,3-benzoxazol-2-yl, l,3-benzoxazol-4-yl, l,3-benzoxazol-5-yl, l,3-benzoxazol-6-yl and l,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(=0)CH3, C(=0)CH2CH2CH3 and C(=0)CH(CH3)2- Non-limiting examples of “alkoxycarbonyl” include CH30C(=0), CH3CH2OC(=O), CH3CH2CH20C(=0), (CH3)2CH0C(=0) and the different butoxy -or pentoxycarbonyl isomers. Non- limiting examples of “alkylaminocarbonyl” include CH3NH C(0=), CH3CH2NHC(=0), CH3CH2CH2NHC(=0), (CH3)2CHNHC(=0) and the different butylamino -or pentylaminocarbonyl isomers. Non-limiting examples of “dialkylaminocarbonyl” include (CH3)2NC(=0), (CH3CH2)2NC(=0), CH3CH2(CH3)NC(=0), CH3CH2CH2(CH3)NC(=0) and (CH3)2CHN(CH3)C(=0). Non-limiting examples of “alkoxyalkylcarbonyl” include CH30CH2C(=0), CH30CH2CH2C(=0), CH3CH20CH2C(=0), CH3CH2CH2CH20CH2C(=0) and CH3CH20CH2CH2C(=0). Non-limiting examples of “alkylthioalkylcarbonyl” include CH3SCH2C(=0), CH3SCH2CH2C(=0), CH3CH2SCH2C(=0), CH3CH2CH2CH2SCH2C(=0) and CH3CH2SCH2CH2C(=0). The term haloalkylsufonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkyl amino and the like are defined analogously
Non-limiting examples of “alkylaminoalkylcarbonyl” include CH3NHCH2C(=0), CH3NHCH2CH2C(=0), CH3CH2NHCH2C(=0), CH3CH2CH2CH2NHCH2C(=0) and CH3CH2NHCH2CH2C(=0).
The term “amide” means A-R'C=ONR"-B, wherein R' and R" indicates substituents and A and B indicate any group.
The term “thioamide” means A-R'C=SNR"-B, wherein R' and R" indicates substituents 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 “pest” 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 the 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 and grape juice 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 use of human 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 parts 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, auxiliary 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 compound of the present disclosure in a composition optionally comprising other compatible compounds to a plant or a plant material or locus thereof include application by a technique known to a person skilled in the art which include 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. Accordingly, the present invention provides a novel oxadizole compound of formula (I),
Figure imgf000016_0001
Formula (I) wherein, R1 is C1-C2-haloalkyl; R2 and R3 are independently selected from the group consisting of hydrogen, halogen, cyano, C1-C6 alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6- haloalkoxy, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylsulfinyl and C1- C6-alkylsulfonyl; R2 and R3 are optionally and independently substituted with halogen, cyano, C1-C6-alkyl, C1-C6- haloalkyl, C3-C6-cycloalkyl or C1-C6-alkoxy; (i) A1 is CR7; and R4 and R7 are independently 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 and C1-C6- alkylsulfonyl; R4 may be optionally substituted with halogen, cyano, amino, C1-C6-alkylamino, C1-C6- dialkylamino, C1-C6-trialkylamino, C1-C6-alkyl, or C1-C6-alkoxy; or (ii) A1 is N and R4 is hydrogen; Q is selected from the group consisting of Q1 to Q11;
Figure imgf000017_0001
R10 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl; R11 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, -(CR12R13)0-4C3-C6-non-aromatic carbocyclyl ring, -(CR12R13)0-4C6-C10-aromatic carbocyclyl ring, -(CR12R13)0-4C3-C6-non-aromatic heterocyclyl ring, -(CR12R13)0-4C6-C10-aromatic heterocyclyl ring, -S(O)0-2C3-C6-non-aromatic carbocyclyl ring, -S(O)0-2C6-C10-aromatic carbocyclyl ring, -S(O)0-2C3-C6-non-aromatic heterocyclyl ring and -S(O)0-2C6-C10-aromatic heterocyclyl ring; or R10 and R11 together the atom to which they are attached may form fused or non-fused 4-8 membered heterocyclic ring containing at least one heteroatom selected from O, S(=O)0-2, or NR14; R14 is selected from the group consisting of hydrogen, C1-6-alkyl and C3-6-cycloalkyl; R12 and R13 are independently selected from the group consisting of hydrogen, halogen, methyl, ethyl, propyl, isopropyl, difluoromethyl, trifluoromethyl, methoxy and ethoxy; R11 may be optionally substituted with halogen, cyano, amino, C1-C6-alkylamino, C1-C6 dialkylamino, C1-C6-trialkylamino, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6- cycloalkyl, C3-C6-cycloalkoxy and phenoxy; or N-oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof. In one embodiment, the compound of formula (I) of the present invention is represented by a compound of formula (la);
Figure imgf000018_0001
wherein, R1, R2, R3, R4, R7, R10 and R11 are as defined in the above detailed description.
In another embodiment, the compound of formula (I) of the present invention is represented by a compound of formula (lb);
Figure imgf000018_0002
wherein, R1, R2, R3, R4, R7, R10 and R11 are as defined in the above detailed description.
In yet another embodiment, the compound of formula (I) of the present invention is represented by a compound of formula (Ic);
Figure imgf000018_0003
wherein, R1, R2, R3, R4, R7, R10 and R11 are as defined in the above detailed description.
In yet another embodiment, the compound of formula (I) of the present invention is represented by a compound of formula (Id);
Figure imgf000019_0001
Formula (Id) wherein, R1, R2, R3, R4, R7 and R11 are as defined in the above detailed description.
In yet another embodiment, the compound of formula (I) of the present invention is represented by a compound of formula (Ie);
Figure imgf000019_0002
Formula (Ie) wherein, R1, R2, R3, R4, R7 and R11 are as defined in the above detailed description.
In yet another embodiment, the compound of formula (I) of the present invention is represented by a compound of formula (If);
Figure imgf000019_0003
Formula (If) wherein, R1, R2, R3, R4, R7, R10 and R11 are as defined in the above detailed description.
In yet another embodiment, the compound of formula (I) of the present invention is represented by a compound of formula (Ig);
Figure imgf000020_0001
Formula (Ig) wherein, R1, R2, R3, R4, R7 and R11 are as defined in the above detailed description.
In yet another embodiment, the compound of formula (I) of the present invention is represented by a compound of formula (Ih);
Figure imgf000020_0002
wherein, R1, R2, R3, R4, R7, R10 and R11 are as defined in the above detailed description.
In yet another embodiment, the compound of formula (I) of the present invention is represented by a compound of formula (Ii);
Figure imgf000020_0003
wherein, R1, R2, R3, R4, R7, R10 and R11 are as defined in the above detailed description.
In yet another embodiment, the compound of formula (I) of the present invention is represented by a compound of formula (Ij); Formula (Ij) wherein, R1, R2, R3, R4, R7, R10 and R11 are as defined in the above detailed description.
In yet another embodiment, the compound of formula (I) of the present invention is represented by a compound of formula (Ik);
Figure imgf000021_0001
Formula (Ik) wherein, R1, R2, R3, R4, R7 and R11 are as defined in the above detailed description.
In a preferred embodiment, the present invention provides a compound of formula (I) wherein,
R1 is selected from the group consisting of -CF3, -CHF2 and -CF2CI;
R2 and R3 are independently selected from the group consisting of hydrogen, halogen, cyano, C1-C6 alkyl, CYCYcycloalkyl, CYCYalkoxy, CYCYhaloalkyl and C1 CYhaloalkoxy;
A1 is CR7; and R4 and R7 are independently selected from the group consisting of hydrogen, halogen, C1-G.-alkyl, CYCYcycloalkyl, CYCYalkoxy and CYCYhaloalkyl;
R11 is selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, CYCYcycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, CYCYcycloal kyl-C 1 -CYal kyl , C1-C6 alkoxy-C1-C6-alkyl, C1-C6-alkylsulfinyl, C 1 - C 6 - a 1 k y 1 s u 1 f o n y 1 , -(CR12R13)0-4 C3-C6-non-aromatic carbocyclyl ring, -(CR12R13)0-4 C6-C10-aromatic carbocyclyl ring, -(CR12R13)0-4 C3-C6-non-aromatic heterocyclyl ring, and -(CR12R13)0-4 C6-C10-aromatic heterocyclyl ring; or
R10 and R11 together 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(=0)o -2, or NR14;
R14is selected from the group consisting of hydrogen, C1-6-alkyl and C3 6-cycloalkyl; R11 may be optionally substituted with halogen, cyano, amino, C1-C6 alkylamino, C1-C6 dialkylamino, C1-C6-trialkylamino, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy and phenoxy, R12 and R13 are independently selected from the group consisting of hydrogen, halogen, methyl, ethyl and propyl. In another preferred embodiment, the present invention provides a compound of formula (I) wherein, R1 is selected from the group consisting of -CF3, -CHF2 and -CF2Cl; R2 and R3 are independently selected from the group consisting of hydrogen, halogen, cyano and C1- C6 alkyl; A1 is CR7; and R4 and R7 are independently selected from the group consisting of hydrogen, halogen and C1-C6-alkyl; R10 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6 alkoxy, and C1-C6-haloalkyl; R11 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, -(CR12R13)0-4C3-C6-non-aromatic carbocyclyl ring, -(CR12R13)0-4C6-C10-aromatic carbocyclyl ring, -(CR12R13)0-4C3-C6-non-aromatic heterocyclyl ring and -(CR12R13)0-4C6-C10-aromatic heterocyclyl ring; or R10 and R11 together 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 NR14; R14 is selected from the group consisting of hydrogen, C1-6-alkyl and C3-6-cycloalkyl; R11 may be optionally substituted with halogen, cyano, amino, C1-C6-alkylamino, C1-C6 dialkylamino, C1-C6-trialkylamino, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy and phenoxy; R12 and R13 are independently selected from the group consisting of hydrogen, halogen, methyl, ethyl, propyl, isopropyl, difluoromethyl, trifluoromethyl, methoxy and ethoxy. In yet another preferred embodiment, R1 is -CF3; R2 and R3 are independently selected from the group consisting of hydrogen and C1-C6 alkyl. In a more preferred embodiment, the compound of formula (I) is selected from ethyl 2-(5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetate, N-(3,4-difluorophenyl)-2-(5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-inol-1-yl)acetamide, 2-(5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)-N-(4-(trifluoromethyl)phenyl)acetamide, N-(2-fluorophenyl)-2-(5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(pyridin-3-yl)-2-(5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(3-fluorophenyl)-2-(5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(3-methoxyphenyl)-2-(5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-methyl-N-(2-phenoxyethyl)-2-(5- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-methyl-N-phenyl-2-(5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, tert-butyl 5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indole-1-carboxylate, (4-(trifluoromethoxy)phenyl)(5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (3-chloro-4-fluorophenyl)(5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (2-fluorophenyl)(5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)methanone, (4-chloro-2-fluorophenyl)(5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)methanone, (3,4-difluorophenyl)(5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)methanone, (2-chloro-6-fluorophenyl)(5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)methanone, p-tolyl(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)methanone, (5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)(4- (trifluoromethyl)phenyl)methanone, (3-fluorophenyl)(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)methanone, N-(m-tolyl)-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)acetamide, (3-methoxyphenyl)(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)methanone, (3-bromophenyl)(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)methanone, 1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, cyclobutyl(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, 1-ethyl-3-(2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)urea, tert-Butyl-2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetate, N-(2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)cyclopropanesulfonamide, N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)ethanesulfonamide, N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol- 1-yl)ethyl)methanesulfonamide, tert-butyl (2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)carbamate, 4-fluoro-N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-benzo[d]imidazol-1-yl)ethyl)benzamide, N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)benzamide, 1-(p-tolyl)-3-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-benzo[d]imidazol-1-yl)ethyl)urea, N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)benzenesulfonamide, 4-methyl-N-(2-(6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzenesulfonamide, N-(2-(6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)isobutyramide , 1-(2-methoxyphenyl)-3-(2-(6- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)urea, N-(2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)acetamide, N-(2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)cyclopropanecarboxamide, 2,6-dimethyl-N-(2-(6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH-benzo[d]imidazol-l- yl)ethyl)benzamide, 2-chloro-6-methyl-N-(2-(6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH- benzo[d]imidazol-l-yl)ethyl)benzamide, 4-methoxy-N-(2-(6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl)-lH-benzo[d]imidazol-l-yl)ethyl)benzenesulfonamide, 4-fluoro-N-(2-(6-(5-(trifluoromethyl)- 1,2,4- oxadiazol-3-yl)-lH-benzo[d]imidazol-l-yl)ethyl)benzenesulfonamide, methyl (2-(6-(5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH-benzo[d]imidazol-l-yl)ethyl)carbamate, N-(2-(6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)- lH-benzo[d]imidazol- 1 -yl)ethyl)thiazole-4-carboxamide, 4- mcthoxy-N-(2-(6-(5-( trill uoromcthyl)- 1 ,2,4-oxadiazol-3-yl)- 1 H-benzo|d]imidazol- 1 - yl)ethyl)benzamide, N-(4-fluorophenyl)-2-(6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH- benzo[d]imidazol-l-yl)acetamide, N-phenyl-2-(6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH- benzo[d]imidazol-l-yl)acetamide, N-(thiazol-2-yl)-2-(6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)- lH-benzo[d]imidazol-l-yl)acetamide, l-(2-oxa-7-azaspiro[3.5]nonan-7-yl)-2-(6-(5-(trifluoromethyl)-
1.2.4-oxadiazol-3-yl)-lH-benzo[d]imidazol-l-yl)ethan-l-one, l-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-2-
(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)- lH-benzo[d]imidazol- 1 -yl)ethan- 1 -one, 1 -morpholino- 2-(6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH-benzo[d]imidazol-l-yl)ethan-l-one, N-(2- fluorophenyl)-2-(6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH-benzo[d]imidazol-l-yl)acetamide, N-(3-methoxybenzyl)-2-(6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH-benzo[d]imidazol-l- yl)acetamide, N-(pyridin-3-yl)-2-(6-(5-( trill uoromcthyl)- 1 ,2,4-oxadiazol-3-yl)- 1 H-bcnzo|d]imidazol- l-yl)acetamide, N-(pyridin-4-ylmethyl)-2-(6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH- benzo[d]imidazol-l-yl)acetamide, cyclopentyl (2-(6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH- benzo[d]imidazol-l-yl)ethyl)carbamate, tert-Butyl-2-(5-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)- lH-benzo[d]imidazol-l-yl)acetate, l-phenyl-3-(2-(6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH- benzo[d]imidazol-l-yl)ethyl)urea, 4-fluorobenzyl (2-(6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)- lH-benzo[d]imidazol-l-yl)ethyl)carbamate, 3-fluoro-N-(2-(6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl)-lH-benzo[d]imidazol-l-yl)ethyl)benzenesulfonamide, 2,4-difluoro-N-(2-(6-(5-(trifluoromethyl)-
1.2.4-oxadiazol-3-yl)-lH-benzo[d]imidazol-l-yl)ethyl)benzenesulfonamide, 2-fluoro-N-(2-(6-(5-
(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)- lH-benzo[d]imidazol- 1 -yl)ethyl)benzenesulfonamide, 1 -(4- chlorophenyl)-3-(2-(6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH-benzo[d]imidazol-l- yl)ethyl)urea, l-benzyl-3-(2-(6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH-benzo[d]imidazol-l- yl)ethyl)urea, l-(2-fluorophenyl)-3-(2-(6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH- benzo[d]imidazol-l-yl)ethyl)urea, l-(2,4-difluorophenyl)-3-(2-(6-(5-(tifluoromethyl)-l,2,4- oxadiazol-3-yl)-lH-benzo[d]imidazol-l-yl)ethyl)urea, l-(cyclopropylmethyl)-3-(2-(6-(5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH-benzo[d]imidazol-l-yl)ethyl)urea, l-isopropyl-3-(2-(6-(5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH-benzo[d]imidazol-l-yl)ethyl)urea, l-cyclopropyl-3-(2-(6- (5-( trill uoromcthyl)- 1 ,2,4-oxadiazol-3-yl)- 1 H-benzo[d]imidazol- 1 -yl)ethyl)urea, 3-fluoro-N-(2-(6-(5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH-benzo[d]imidazol-l-yl)ethyl)benzamide, 4-methyl-N-(2- (6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)-lH-benzo[d]imidazol-l-yl)ethyl)benzamide , N-(2-(6- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)cyclobutanecarboxamide, N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)pivalamide, N-(2- (6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)propionamide, 4- (trifluoromethyl)-N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)benzamide, 4-chloro-N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)benzamide, 3,5-difluoro-N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzamide, 2-fluoro-N-(2-(6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzamide, N-(2-(6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)oxazole-4-carboxamide, 2,4-difluoro-N-(2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzamide, N-(2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)nicotinamide, N- (methyl(oxo)(pyridin-2-yl)-λ6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)acetamide, N-(methyl(oxo)(4-(trifluoromethyl)pyridin-2-yl)-λ6- sulfaneylidene)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetamide, N-((4-chlorophenyl)(methyl)(oxo)-λ6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-benzo[d]imidazol-1-yl)acetamide, N-(4-oxido-1,4-λ6-oxathian-4-ylidene)-2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetamide, N-((3- fluorophenyl)(methyl)(oxo)-λ6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)acetamide, N-((4-fluoro-2-methoxyphenyl)(methyl)(oxo)-λ6-sulfaneylidene)-2- (6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetamide, N-((3- methoxybenzyl)(methyl)(oxo)-λ6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)acetamide, N-Phenyl-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)acetamide, N-(4-fluorophenyl)-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-benzo[d]imidazol-1-yl)acetamide, N-(pyridin-3-yl)-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-benzo[d]imidazol-1-yl)acetamide, N-(3-methoxybenzyl)-2-(5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetamide, N-(2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)isobutyramide, N-(2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzamide, 4-chloro-N-(2-(5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzamide, 4-fluoro-N-(2-(5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzamide, N-(2-(5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)cyclopropanesulfonamide, 2-methyl-N-(2-(5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzenesulfonamide, 4- methoxy-N-(2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)benzenesulfonamide, N-(2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)methanesulfonamide, N-(2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-benzo[d]imidazol-1-yl)ethyl)nicotinamide, 1-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)propan-1-one, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)-2-phenylacetamide, N-(4-chlorophenyl)-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-indol-1-yl)acetamide, N-isopropyl-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)acetamide, N-(2-fluoro-5-methoxyphenyl)-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)acetamide, isoxazol-4-yl(3-methyl-6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)methanone, (3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)(p-tolyl)methanone, 1-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)-2-(4-(trifluoromethyl)phenyl)ethan-1-one, (3-methyl-5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)(phenyl)methanone, 1-(4-methoxyphenyl)-N-(2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)methanesulfonamide, 4-methyl-N-(2-(3- methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzenesulfonamide, oxetan- 3-yl(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, 1-(6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, cyclopropyl(6-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-indol-1-yl)methanone, cyclopentyl(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)methanone, cyclobutyl(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, 2- methyl-1-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)propan-1-one, 2-phenyl-1-(6- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 2-(p-tolyl)-1-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 2-(4-fluorophenyl)-1-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 2-(4-methoxyphenyl)-1-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 1-(6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)-2-(4-(trifluoromethyl)phenyl)ethan-1-one, 2-(4-chlorophenyl)-1-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 2-methoxy-1-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)propan-1-one, 2-(pyridin-3-yl)-1-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 2-(pyrimidin-5-yl)-1-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, phenyl(6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (4-fluorophenyl)(6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)methanone, (4-chlorophenyl)(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)methanone, p-tolyl(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)methanone, 2-(2,4-difluorophenyl)-1-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethan-1-one, (2-fluorophenyl)(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)methanone, (1-methyl-1H-pyrazol-4-yl)(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)methanone, isoxazol-4-yl(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (1-methyl-1H-pyrazol-3-yl)(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (2-fluoro-5-methoxyphenyl)(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)ethanesulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)oxetane-3- sulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)methanesulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol- 1-yl)ethyl)cyclopropanesulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)ethyl)cyclopentanesulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)cyclobutanesulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)propane-2-sulfonamide, N-(2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1-phenylmethanesulfonamide, N-(2-(3- methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1-(p- tolyl)methanesulfonamide, 1-(4-fluorophenyl)-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-indol-1-yl)ethyl)methanesulfonamide, 1-(4-methoxyphenyl)-N-(2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)methanesulfonamide, N-(2-(3-methyl-6- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1-(4- (trifluoromethyl)phenyl)methanesulfonamide, 1-(4-chlorophenyl)-N-(2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)methanesulfonamide, 1-methoxy-N-(2- (3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)ethane-1-sulfonamide, N- (2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1-(pyridin-3- yl)methanesulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)-1-(pyrimidin-5-yl)methanesulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzenesulfonamide, 4-fluoro-N-(2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzenesulfonamide, 4-chloro-N-(2-(3- methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzenesulfonamide, 4- methyl-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)benzenesulfonamide, 1-(2,4-difluorophenyl)-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)methanesulfonamide, 2-fluoro-N-(2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzenesulfonamide, 1-methyl-N-(2-(3- methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1H-pyrazole-4-sulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)isoxazole-4- sulfonamide, 1-methyl-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)-1H-pyrazole-3-sulfonamide, 2-fluoro-5-methoxy-N-(2-(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzenesulfonamide, N-(2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)propionamide, N-(2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)oxetane-3-carboxamide, N-(2-(3-methyl- 6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)acetamide, N-(2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)cyclopropanecarboxamide, N-(2-(3- methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)cyclopentanecarboxamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)cyclobutanecarboxamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethyl)isobutyramide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethyl)-2-phenylacetamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)ethyl)-2-(p-tolyl)acetamide, 2-(4-fluorophenyl)-N-(2-(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)acetamide, 2-(4-methoxyphenyl)-N-(2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)acetamide, N-(2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-2-(4-(trifluoromethyl)phenyl)acetamide, 2-(4-chlorophenyl)-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)acetamide, 2-methoxy-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethyl)propanamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol- 1-yl)ethyl)-2-(pyridin-3-yl)acetamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)ethyl)-2-(pyrimidin-5-yl)acetamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzamide, 4-fluoro-N-(2-(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzamide, 4-chloro-N-(2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzamide, 4-methyl-N-(2-(3-methyl-6- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzamide, 2-(2,4-difluorophenyl)-N- (2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)acetamide, 2-fluoro-N- (2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzamide, 1-methyl- N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1H-pyrazole-4- carboxamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)isoxazole-4-carboxamide, 1-methyl-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)ethyl)-1H-pyrazole-3-carboxamide, 2-fluoro-5-methoxy-N-(2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzamide, N-ethyl-2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, 2-(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N-(oxetan-3-yl)acetamide, N-methyl-2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-cyclopropyl-2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-cyclopentyl-2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-cyclobutyl-2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-isopropyl-2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-benzyl-2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, 2-(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N-(4-methylbenzyl)acetamide, N-(4-fluorobenzyl)-2-(3-methyl- 6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(4-methoxybenzyl)-2-(3- methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, 2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N-(4-(trifluoromethyl)benzyl)acetamide, N-(4- chlorobenzyl)-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, 2- (3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N-(pyridin-3- ylmethyl)acetamide, 2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N- (pyrimidin-5-ylmethyl)acetamide, 2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol- 1-yl)-N-phenylacetamide, N-(4-fluorophenyl)-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)acetamide, N-(4-chlorophenyl)-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-indol-1-yl)acetamide, 2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)-N-(p-tolyl)acetamide, N-(2,4-difluorobenzyl)-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-indol-1-yl)acetamide, N-(2-fluorophenyl)-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(1-methyl-1H-pyrazol-4-yl)-2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(isoxazol-4-yl)-2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(1-methyl-1H-pyrazol-3-yl)-2-(3- methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(2-fluoro-5- methoxyphenyl)-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)cyclopentanecarboxamide, 4-chloro-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-indol-1-yl)ethyl)benzamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)ethyl)-2-(pyridin-3-yl)acetamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)oxetane-3-carboxamide, 2-(4-methoxyphenyl)-N-(2-(3-methyl-5- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)acetamide, 2-(4-chlorophenyl)-N-(2- (3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)acetamide, N-(2-(3- methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)propionamide, N-(2-(3- methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-2-(4- (trifluoromethyl)phenyl)acetamide, 2-(4-fluorophenyl)-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)acetamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-2-(p-tolyl)acetamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)acetamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)cyclopropanecarboxamide, N-(2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)isobutyramide, N-(2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)cyclobutanecarboxamide, N-(2-(3- methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)isoxazole-4-carboxamide, 1- methyl-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1H- pyrazole-4-carboxamide, 1-methyl-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethyl)-1H-pyrazole-3-carboxamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-indol-1-yl)ethyl)benzamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)ethyl)-2-(pyrimidin-5-yl)acetamide, 4-fluoro-N-(2-(3-methyl-5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzamide, 4-methyl-N-(2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzamide, 2-(2,4-difluorophenyl)-N-(2- (3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)acetamide, 2-fluoro-N-(2- (3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzamide, 2-fluoro-5- methoxy-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)benzamide, N-cyclopentyl-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)acetamide, 2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N- (pyridin-3-ylmethyl)acetamide, 2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)-N-(oxetan-3-yl)acetamide, N-(4-methoxybenzyl)-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(4-chlorobenzyl)-2-(3-methyl-5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-ethyl-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)acetamide, 2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)-N-(4-(trifluoromethyl)benzyl)acetamide, N-(4-fluorobenzyl)-2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-benzyl-2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, 2-(3-methyl-5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N-(4-methylbenzyl)acetamide, N-methyl-2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-cyclopropyl-2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-cyclobutyl-2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(1-methoxyethyl)-2-(3-methyl-5- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(isoxazol-4-yl)-2-(3-methyl-5- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(1-methyl-1H-pyrazol-4-yl)-2- (3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(1-methyl-1H- pyrazol-3-yl)-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, 2- (3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N-phenylacetamide, 2-(3- methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N-(pyrimidin-5- ylmethyl)acetamide, N-(4-fluorophenyl)-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)acetamide, 2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N- (p-tolyl)acetamide, N-(2,4-difluorobenzyl)-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)acetamide, N-(2-fluorophenyl)-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)acetamide, cyclopentyl(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)methanone, 4-chlorophenyl)(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)methanone, 1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-2- (pyridin-3-yl)ethan-1-one, (3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)(oxetan-3-yl)methanone, 2-(4-methoxyphenyl)-1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-indol-1-yl)ethan-1-one, 2-(4-chlorophenyl)-1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)propan-1-one, 1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)-2-(4-(trifluoromethyl)phenyl)ethan-1-one, 2-(4-fluorophenyl)-1-(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-indol-1-yl)-2-phenylethan-1-one, 1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)-2-(p-tolyl)ethan-1-one, 1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethan-1-one, cyclopropyl(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol- 1-yl)methanone, 2-methyl-1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)propan-1-one, cyclobutyl(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)methanone, 2-methoxy-1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)propan-1-one, (1-methyl-1H-pyrazol-4-yl)(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)methanone, (1-methyl-1H-pyrazol-3-yl)(3-methyl-6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)methanone, (3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)(phenyl)methanone, 1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)-2-(pyrimidin-5-yl)ethan-1-one, (4-fluorophenyl)(3-methyl-6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)methanone, 2-(2,4-difluorophenyl)-1-(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, (2-fluorophenyl)(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (2-fluoro-5-methoxyphenyl)(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, cyclopentyl(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (4-chlorophenyl)(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, 1-(3-methyl-5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-2-(pyridin-3-yl)ethan-1-one, (3-methyl-5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)(oxetan-3-yl)methanone, 2-(4-methoxyphenyl)-1-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 2-(4-chlorophenyl)-1-(3-methyl-5- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 1-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)propan-1-one, 2-(4-fluorophenyl)-1-(3-methyl- 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 1-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-2-phenylethan-1-one, 1-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-2-(p-tolyl)ethan-1-one, 1-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, cyclopropyl(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, 2-methyl-1-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)propan-1-one, cyclobutyl(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, 2-methoxy-1-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)propan-1-one, isoxazol-4-yl(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (1-methyl-1H-pyrazol-4-yl)(3- methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (1-methyl-1H-pyrazol- 3-yl)(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, 1-(3-methyl-5- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-2-(pyrimidin-5-yl)ethan-1-one, (4- fluorophenyl)(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (3- methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)(p-tolyl)methanone, 2-(2,4- difluorophenyl)-1-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, (2-fluorophenyl)(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (2- fluoro-5-methoxyphenyl)(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)methanone, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)cyclopentanesulfonamide, 4-chloro-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)ethyl)benzenesulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-indol-1-yl)ethyl)-1-(pyridin-3-yl)methanesulfonamide, N-(2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)oxetane-3-sulfonamide, 1-(4- chlorophenyl)-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)methanesulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol- 1-yl)ethyl)ethanesulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol- 1-yl)ethyl)-1-(4-(trifluoromethyl)phenyl)methanesulfonamide, 1-(4-fluorophenyl)-N-(2-(3-methyl-5- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)methanesulfonamide, N-(2-(3-methyl- 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1-phenylmethanesulfonamide, N- (2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1-(p- tolyl)methanesulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)methanesulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol- 1-yl)ethyl)cyclopropanesulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)ethyl)propane-2-sulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-indol-1-yl)ethyl)cyclobutanesulfonamide, 1-methoxy-N-(2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)ethane-1-sulfonamide, N-(2-(3-methyl-5- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)isoxazole-4-sulfonamide, 1-methyl-N- (2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1H-pyrazole-4- sulfonamide, 1-methyl-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)-1H-pyrazole-3-sulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)ethyl)benzenesulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)ethyl)-1-(pyrimidin-5-yl)methanesulfonamide, 4-fluoro-N-(2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzenesulfonamide, 1-(2,4- difluorophenyl)-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)methanesulfonamide, 2-fluoro-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)ethyl)benzenesulfonamide and 2-fluoro-5-methoxy-N-(2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzenesulfonamide. In one embodiment, the present invention provides a compound of formula (II);
Figure imgf000032_0001
Formula (II) wherein, Ra is selected from the group consisting of cyano or –CH2(NH2)=N-OH; R2, R3, R4, A1 and Q are as defined in the detailed description. In one embodiment, the present invention provides a compound of formula (III) or salts thereof;
Figure imgf000033_0001
Formula (III) wherein, Rb is selected from the group consisting of hydrogen or –C1-C4-alkyl-NH-R10; R1, R2, R3, R4, and A1 are as defined in the detailed description. The compounds of the present invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. 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 stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. The compound of the present invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form. An anion part of the salt in case the compound of formula (I) is a 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 an anionic or capable of forming an anion can be inorganic or organic. Examples of an inorganic anion part of the salt include but are not limited to chloride, bromide, iodide, fluoride, sulphate, phosphate, nitrate, nitrite, hydrogen carbonates, hydrogen sulphate. Examples of 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 an inorganic cation part of the salt include but are not limited to alkali and alkaline earth metals. Examples of 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 metal complexes of the compounds 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 group, 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), typically may exist in more than one form. Formula (I) thus includes all crystalline and non- crystalline forms of the compound 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). In an embodiment, the present invention provides a process for the synthesis of a compound of formula (I). The process for the synthesis of compounds of formula (I) is comprising at least one of the following steps (a) to (k): a) reacting a compound of formula 2 with a hydroxyl amine to afford a compound of formula 4;
Figure imgf000034_0001
wherein, R2 or R3 is not cyano; R4, Q and A1 are as defined in the above detailed description; b) reacting the compound of formula 4 with a suitable carboxylic acid anhydride of formula 5a or suitable carboxylic acid chloride of formula 5b to afford a compound of formula (I);
Figure imgf000034_0002
wherein, R1, R2, R3, R4, Q and A1 are as defined in the above detailed description; c) reacting a compound of formula 6a with a compound of formula 7 to afford a compound of formula (I);
Figure imgf000035_0005
wherein, Q is Q1; R is hydrogen or alkyl; R1, R2, R3, R4 and A1 are as defined in detailed description above; d) reacting a compound of formula 10 with a suitable acid to afford a compound of formula 11;
Figure imgf000035_0001
wherein, R1, R2, R3, R4 and A1 are as defined in detailed description above; e) reacting a compound of formula 11 with a suitable acid chloride to afford a compound of formula (I);
Figure imgf000035_0002
wherein, Q is Q4; R1, R2, R3, R4 and A1 are as defined in detailed description above; f) reacting a compound of formula 20 with a suitable deprotecting reagent to afford a compound of formula 21;
Figure imgf000035_0003
wherein, R1, R2, R3, R4, R10 and A1 are as defined in detailed description above; g) reacting a compound of formula 21 with a suitable acid chloride of formula 15a or a suitable acid of formula 15b to afford a compound of formula (I);
Figure imgf000035_0004
wherein, Q is Q2; R1, R2, R3, R4, R10, R11 and A1 are as defined in detailed description above; h) reacting a compound of formula 21 with a sulfonyl chloride compound of formula 5c to afford a compound of formula (I);
Figure imgf000036_0001
wherein, Q is Q3; R1, R2, R3, R4, R10, R11 and A1 are as defined in detailed description above; i) reacting the compound of formula 21 with amine compound of formula 10a or isocyanate compound of formula 10b afford a compound of formula (I);
Figure imgf000036_0002
wherein, Q is Q8; R1, R2, R3, R4, R10, R11 and A1 are as defined in detailed description above; j) reacting a compound of formula 21 with a compound of formula 10c or 10d to afford a compound of formula (I);
Figure imgf000036_0003
wherein, Q is Q9; R1, R2, R3, R4, R10, R11 and A1 are as defined in detailed description above; k) reacting a compound of formula 32 with a sulfoximine compound of formula 7a to afford a compound of formula (I);
Figure imgf000036_0004
wherein, Q is Q10; R1, R2, R3, R4, R10, R11 and A1 are as defined in detailed description above. The following schemes illustrate approaches for preparing 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 8 may be prepared, in known manner, in a variety of ways as described in the schemes 1-12. The definitions of R1, R2, R3, R4, A1 and Q in the compounds of formula (I) and in the compounds of formula 1 to 30 are as defined in the above detailed description of the invention unless otherwise specifically stated. General Scheme: 1
Figure imgf000037_0001
wherein, Q is Q1; R2, R3 and R4 are H; A1 is CH. Step: 1
Figure imgf000037_0002
The compound of formula 2 can be prepared by alkylating the compound of formula 1 with haloethyl acetate (X= Cl, Br, and I) of formula 3 in the presence of a suitable base such as sodium hydride, potassium carbonate, cesium carbonate, etc. This reaction is typically carried out in a suitable solvent such as N,N-dimethylformamide or tetrahydrofuran at atemperature ranging from 0-70 oC. Step: 2
Figure imgf000037_0003
The compound of formula 2 is treated with hydroxylamine hydrochloride in the presence of a suitable base such as sodium bicarbonate or triethyl amine to obtain the compound of formula 4. This reaction is typically carried out in a suitable solvent such as methanol, ethanol or tetrahydrofuran at a temperature ranging from 0-65 oC. Alternatively, this reaction can also be carried out by reacting the compound of formula 2 with 50 % aqueous hydroxyl amine solution in a suitable solvent such as methanol, ethanol or tetrahydrofuran at a temperature ranging from 0-65 oC. Step: 3
Figure imgf000038_0001
The compound of formula 6a can be prepared by reacting the compound of formula 4 with a suitable acid anhydride of formula 5a in a suitable solvent such as tetrahydrofuran or dichloromethane at a temperature ranging from 0-50 oC. Alternatively, this reaction can also be carried out by reacting compound of formula 4 with carboxylic acid chloride of formula 5b in the presence of a suitable solvent such as tetrahydrofuran, 2-methyl tetrahydrofuran, dichloromethane, etc. at temperature ranging from 0-100 oC. Step: 4
Figure imgf000038_0002
The compound of formula 6a may then be treated with amine derivatives of formula 7 in the presence of trimethyl aluminum to obtain the compound of formula (I) wherein Q is Q1. This reaction is typically carried out in a suitable solvent such as toluene or tetrahydrofuran at a temperature ranging from 20-110 oC. General scheme: 2
wherein, Q is Q4; R2, R3 and R4 are H; A1 is CH. Step: 1 The compound of formula 8 can be prepared by reacting the compound of formula 7 with di-tert-butyl dicarbonate in the presence of a suitable base such as 4-dimethylaminopyridine in suitable solvent such as dichloromethane or tetrahydrofuran at a temperature ranging from 0-25 oC. Step: 2
Figure imgf000039_0001
The compound of formula 9 can be prepared by reacting the compound of formula 8 with hydroxyl amine hydrochloride in the presence of a suitable base such as sodium bicarbonate or triethyl amine. This reaction is generally carried out in a suitable solvent such as methanol, ethanol or tetrahydrofuran at a temperature ranging from 10-65 oC. Alternatively, this reaction can also be carried out by reacting the compound of formula 8 with 50% aqueous hydroxyl amine solution in a suitable solvent such as methanol, ethanol or tetrahydrofuran at a temperature ranging from 10-65 oC. Step: 3
Figure imgf000040_0001
The compound of formula 10 can be prepared by reacting the compound of formula 9 with an acid anhydride of formula 5a. This reaction is typically carried out in a suitable solvent such as tetrahydrofuran or dichloromethane at temperature ranging from 0-50 oC. Alternatively, this reaction can also be carried out by reacting the compound of formula 9 with the carboxylic acid chloride of formula 5b in the presence of a suitable solvent such as tetrahydrofuran, 2- methyl tetrahydrofuran, dichloromethane, etc. at a temperature ranging from 0-100 oC. Step: 4
Figure imgf000040_0002
The compound of formula 11 can be obtained by reacting the compound of formula 10 with a suitable acid such as trifluoroacetic acid or hydrochloric acid. This reaction is carried out in a suitable solvent such as dichloromethane or tetrahydrofuran at a temperature ranging from 0-25 oC. Step: 5
Figure imgf000040_0003
The compound of formula (I) can be obtained by reacting the compound of formula 11 with a suitable acid chloride of formula 12 in the presence of an suitable organic base such as triethyl amine, diisopropyl ethyl amine or pyridine. This reaction is typically carried out in a suitable solvent such as dichloromethane and catalyst such as 4-dimethylaminopyridine at a temperature ranging from 0-25 oC. General scheme: 3 wherein R2, or R3 is H, Step: 1 The compound of formula 13 can be obtained by reacting the compound of formula 12 with the compound of formula 12a in the presence of a suitable base such as triethylamine, potassium carbonate, cesium carbonate, etc. This reaction is typically carried out in a suitable solvent such as N,N-dimethylformamide, dimethyl sulfoxide, etc. at a temperature ranging from 10-100 oC. Step: 2
Figure imgf000041_0001
The compound of formula 14 can be obtained by reducing the compound of formula 13 in the presence of a suitable reducing agent such as iron/ammonium chloride in a suitable solvent such as methanol, water, ethanol etc or mixture therof. Step: 3
Figure imgf000041_0002
The compound of formula 15 can be prepared by reacting the compound of formula 14 with the compound of formula 10f in the presence of suitable acid catalyst such as p-toluenesulfonic acid etc. This reaction is typically carried out in a suitable solvent such as ethanol, toluene, etc. at a temperature of about 50-80 oC. General scheme: 4
Figure imgf000042_0002
The compound of formula 16 can be obtained by reacting compound of formula 12 with the compound of formula 12a in the presence of a suitable base such as triethylamine, potassium carbonate, cesium carbonate, etc. This reaction is typically carried out in a suitable solvent such as N,N-dimethylformamide, dimethyl sulfoxide, etc. at a temperature ranging from 10-100 oC. Step: 2
Figure imgf000042_0001
The compound of formula 17 can be obtained by reducing the compound of formula 16 in the presence of a suitable reducing agent such as iron/ammonium chloride in a suitable solvent such as methanol, water, ethanol etc or mixture therof. Step: 3
Figure imgf000042_0003
The compound of formula 18b can be prepared by reacting the compound of formula 17 with the compound of formula 10f in the presence of a suitable acid catalyst such as p-toluenesulfonic acid etc. This reaction is typically carried out in a suitable solvent such as ethanol, toluene, etc. at a temperature ranging from 50-80 oC. General scheme: 5
Figure imgf000043_0001
The compound of formula 19 can be prepared by reacting the compound of formula 18ab with hydroxyl amine hydrochloride in the presence of a suitable base such as sodium bicarbonate or triethyl amine. This reaction is generally carried out in a suitable solvent such as methanol, ethanol or tetrahydrofuran at a temperature ranging from 10-65 oC. Alternatively, this reaction an also be carried out by reacting the compound of formula 18ab with a 50% aqueous hydroxyl amine solution in a suitable solvent such as methanol, ethanol or tetrahydrofuran at a temperature ranging from 10-65 oC. Step: 2 The compound of formula 20 can be prepared by reacting the compound of formula 19 with an acid anhydride of formula 5a. This reaction is typically carried out in a suitable solvent such as tetrahydrofuran or dichloromethane at a temperature ranging from 0-50 oC. Alternatively, this reaction can also be carried out by reacting the compound of formula 19 with carboxylic acid chloride of formula 5b in the presence of a suitable solvent such as tetrahydrofuran, 2- methyl tetrahydrofuran, dichloromethane, etc. at a temperature ranging from 0-100 oC. Step: 3
Figure imgf000044_0001
The compound of formula 21 can be obtained by deprotecting the compound of formula 20 with a suitable deprotecting reagents such as hydrochloric acid in a suitable solvent such as dichloromethane, tetrahydrofuran, 1,4-dioxane etc. at ambient temperature. Step: 4
Figure imgf000044_0002
The compound of formula (I) wherein Q is Q2 can be prepared by reacting the compound of formula 21 with a suitable acid chloride of formula 15a in the presence of base such as triethylamine, diisopropylethylamine, etc. This reaction is typically carried out in a suitable aprotic solvent such as 2-methylterahydrofuran, tetrahydrofuran, dichloromethane, etc. at a temperature ranging from 0-30 oC. Alternatively, the compound of formula (I) can be prepared by reacting a carboxylic acid compound of formula 15b in the presence of an amide coupling reagent such as 1-Ethyl-3-(3- dimethylaminopropyl)carbodiimide (EDCl), hydroxybenzotriazole (HOBt), 1- [Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), etc. This reaction is carried out in the presence of a base such as triethylamine, diisopropylethylamine in aprotic solvents such as dichloromethane, tetrahydrofuran, dimethyl formamide etc. This reaction can be carried out at a temperature ranging from 0-60 °C. General scheme: 6
Figure imgf000045_0002
The compound of formula 23 can be obtained by reacting the compound of formula 22 with a compound of formula 10e in the presence of a suitable base such as sodium bicarbonate, potassium carbonate or cesium carbonate. This reaction is typically carried out in a suitable aprotic solvent such as N,N-dimethylformamide, dimethyl sulfoxide, etc. at a temperature ranging from at 0-30 oC. Step: 2
Figure imgf000045_0001
The compound of formula 25 can be prepared by reacting the compound of formula 23 with the compound of formula 10f in the presence of a suitable acid catalyst such as p-toluenesulfonic acid etc. This reaction is typically carried out in solvents such as ethanol, toluene, etc. at a temperature ranging from 50-80 oC. Step: 3
Figure imgf000046_0001
The compound of formula 26a can be prepared by cyanation of the compound of formula 25 in the presence of a suitable cyanide source such as potassium hexacyanoferrate(II) trihydrate and a suitable catalyst such as Pd(Xanphos)allylCl in the presence of potassium acetate as reported in J. Org. Chem. 2018, 83, 4922−4931. Alternatively, this reaction can also be carried out in the presence of potassium hexacyanoferrate(II) trihydrate, palladium (II) diacetate and sodium bicarbonate in 1,4-dioxane as described in Organometallics, 2015, vol.34 (10), p.1942 – 1956. General scheme: 7
Figure imgf000046_0002
The compound of formula 28 can be obtained by reacting the compound of formula 27 with the compound of formula 10e in the presence of a suitable base such as sodium bicarbonate, potassium carbonate or cesium carbonate. This reaction is typically carried out in a suitable aprotic solvent such as N,N-dimethylformamide, dimethyl sulfoxide, etc. at a temperature ranging from 0-30 oC Step: 2 The compound of formula 26b can be obtained by reacting the compound of formula 28 with the compound of formula 10f in the presence of a suitable acid catalyst such as p-toluenesulfonic acid etc. This reaction is typically carried out in a suitable solvent such as ethanol, toluene, etc. at a temperature ranging from 50-80 oC. General scheme: 8
Figure imgf000047_0001
Wherein Q is Q1; R2 or R3 is not CN; Step: 1
Figure imgf000047_0002
The compound of formula 30 can be prepared by reacting the compound of formula 26ab with hydroxyl amine hydrochloride in the presence of a suitable base such as sodium bicarbonate or triethyl amine. This reaction is generally carried out in a suitable solvent such as methanol, ethanol or tetrahydrofuran at a temperature ranging from 10-65 oC. Alternatively, this reaction can also be carried out by reacting the compound of formula 26ab with a 50% aqueous hydroxyl amine solution in a suitable solvent such as methanol, ethanol or tetrahydrofuran at a temperature ranging from 10-65 oC. Step: 2
Figure imgf000048_0001
The compound of formula 6b can be prepared by reacting the compound of formula 30 with a suitable acid anhydride of formula 5a. This reaction is typically carried out in a suitable solvent such as tetrahydrofuran or dichloromethane at a temperature ranging from 0-50 oC. Alternatively, this reaction can also be carried out by reacting the compound of formula 30 with carboxylic acid chloride of formula 5b in the presence of a suitable solvent such as tetrahydrofuran, 2- methyl tetrahydrofuran, dichloromethane, etc. at a temperature ranging from 0-100 oC. Step: 3
Figure imgf000048_0002
The compound of formula 6c can be obtained by hydrolyzing the compound of formula 6b in the presence of a suitable acid such as trifluoroacetic acid in a suitable solvent such as dichloromethane at ambient temperature. Step: 4
Figure imgf000048_0003
The compound of formula (I) wherein Q is Q1 can be obtained by reacting the compound of formula 6c with the compound of formula 7 in the presence of a suitable amide coupling reagent such as 1- Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCl), hydroxybenzotriazole (HOBt), 1- [Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), etc. This reaction is carried out in the presence of a base such as triethylamine, diisopropylethylamine in a suitable aprotic solvent such as dichloromethane, tetrahydrofuran, dimethyl formamide etc. This reaction can be carried out at a temperature ranging from 0-60 °C. General scheme: 9
Figure imgf000049_0001
The compound of formula (I) wherein Q is Q3 can be prepared by reacting the compound of formula 21 with a sulfonyl chloride compound of formula 5c in the presence of a suitable base such as triethylamine, N,N-diisopropylethylamine in a suitable aprotic solvent such as dichloromethane, tetrahydrofuran, etc. at ambient temperature. General scheme: 10
Figure imgf000049_0002
wherein, Q is Q8. The compound of formula (I) wherein Q is Q8, can be prepared by reacting the compound of formula 21 with an isocyanate compound of formula 10b in the presence of a suitable base such as triethylamine, N,N-diisopropylethylamine in a suitable aprotic solvents such as dichloromethane, tetrahydrofuran, etc. at ambient temperature. Alternatively, the compound of formula (I) wherein Q is Q8 can also be prepared by reacting the compound of formula 21 with an amine compound of formula 10a in the presence of triphosgene or phosgene. This reaction is typically carried out in the presence of a base such as triethylamine, N,N- diisopropylethylamine in aprotic solvents such as dichloromethane, tetrahydrofuran, etc. at ambient temperature. General scheme: 11
Figure imgf000049_0003
The compound of formula (I) wherein Q is Q9 can be prepared by reacting the compound of formula 21 with the compound of formula 10c in the presence of a base such as triethylamine, N,N- diisopropylethylamine in a suitable aprotic solvent such as dichloromethane, tetrahydrofuran, etc. at ambient, higher or lower temperature. Alternatively, the compound of formula (I) wherein Q is Q9 can be prepared by reacting the compound of formula 21 with the compound of formula 10d in the presence of triphosgene or phosgene. This reaction is typically carried out in the presence of a suitable base such as triethylamine, N,N-diisopropylethylamine in a suitable aprotic solvent such as dichloromethane, tetrahydrofuran, etc. at ambient, higher or lower temperature. General scheme: 12
Figure imgf000050_0001
The compound of formula (I) wherein Q is Q10 can be obtained by reacting the compound of formula 6c with a sulfoximine compound of formula 7a in the presence of a suitable coupling reagent such as 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCl), 4-dimethylaminopyridine (DMAP), 1- [Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), etc. In one embodiment, the present invention relates to a composition comprising the compound of formula (I), 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 ingredient with the auxiliary such as inert carrier or any other essential ingredient such as surfactants, additives, solid diluents and liquid diluents. The compound of formula (I) and the composition 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 compound of formula (I) and the composition 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 and grape juice 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 compound of Formula I and the composition according to the invention are important in the control of phytopathogenic fungi on soybeans and on the plant propagation material, such as seeds, and the crop material of soybeans. Accordingly, the present invention also includes a composition 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. Preferably, the compound of Formula I and composition 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. Preferably, treatment of plant propagation materials with the compound 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; rice, corn, cotton, fruits, coffee, sugarcane 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 such as 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 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, Monsanto, U.S.A.), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate-tolerant, Bayer CropScience, 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 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 controlling or preventing 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 controlling or preventing 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 disease 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 controlling or preventing 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 further relates to the use of the compounds of Formula I, the combinations or the compositions thereof for controlling or preventing against phytopathogenic fungi such as Phakopsora pachyrhizi, Phakopsora meibomiae, of agricultural crops and or horticultural crops. The compound of Formula I, the combination and the composition thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials. 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 compound of Formula I, the combination and the composition thereof, respectively, are particularly suitable for controlling the following plant diseases: Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans. In one embodiment, the present invention provides a method for controlling or preventing phytopathogenic fungi, wherein said 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 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 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 to 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 compound 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 compound of Formula I are employed as such or in the form of composition 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 substances. 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. In one embodiment, the present invention provides an agrochemical composition 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 compound 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. 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 compositions 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 are 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 mineral earths, e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulphate, magnesium sulphate, magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers, e. g. ammonium sulphate, 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, 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 alkali, alkaline earth or ammonium salts of sulfonates, sulphates, 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 sulphates are sulphates 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 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 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 home- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate. Suitable cationic surfactants are 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 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 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 compound 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 polysaccharides (e. g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates. Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones. Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin. Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids. Suitable colorants (e. g. in red, blue, or green) are 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 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 organic solvent (e. g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion. iii) Emulsifiable concentrates (EC) 15-70 wt% of a compound of Formula I and 5-10 wt% emulsifiers (e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion. iv) Emulsions (EW, EO, ES) 5-40 wt% of a compound of Formula I and 1-10 wt% emulsifiers (e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 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. v) Suspensions (SC, OD, FS) In an agitated ball mill, 20-60 wt% of a compound of Formula I are comminuted with 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 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 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 addition of 1-5 wt% dispersants (e. g. sodium lignosulfonate), 1-3 wt% wetting agents (e. g. alcohol ethoxylate) and solid carrier (e. g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance. viii) Gel (GW, GF) In an agitated ball mill, 5-25 wt% of a compound of Formula I are comminuted with addition of 3-10 wt% dispersants (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) Microemulsion (ME) 5-20 wt% of a compound of Formula I are added to 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. x) Microcapsules (CS) An oil phase comprising 5-50 wt% of a compound of Formula I, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt% 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% 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. The monomers amount to 1-10 wt%. The wt% relate 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 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 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 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 of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum). For the purposes of 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. Application can be carried out before or during sowing. Methods for applying the compound of Formula I, the combination and the composition thereof, respectively, are application onto plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods. Preferably, the compound of Formula I, the combination and the composition thereof, respectively, are applied on to the plant propagation material by a method such that 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 0.05 to 1 kg per ha, more preferably 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 seed, amounts of active substance 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) are generally required. 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 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material. Various types of oils, wetters, adjuvants, fertilizer, 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 premix or, if appropriate not until immediately prior to use (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 a 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 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 the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the 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 thus obtained. 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. The compound of formula (I), the combination and the composition 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. In one embodiment, the present invention provides a combination comprising at least one compound of formula (I) and at least one further pesticidally active substance 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 compound of formula (I). The 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 IU PAC 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 compound of formula (I) together with at least one pesticidally active compound an additional effect can be obtained. This can be obtained by applying the compound 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 to ensure 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 working of the present invention. When applying the compound 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 composition 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 on 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 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 N-(3,4-difluorophenyl)-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)acetamide (compound no.2) a) Step 1: 2-(5-Cyano-1H-indol-1-yl)acetate To a stirred solution of 5-cyano indole (5g, 35 mmol) in N,N-dimethylformamide (100 mL), sodium hydride (2 g, 49 mmol) was added at 0-2 °C under nitrogen atmosphere. The resulting reaction mixture was stirred at 25 °C for 30 min and cooled to 0-2 °C. To this reaction mixture, ethyl 2- bromoacetate (5.5 mL, 49 mmol) was added drop wise and the resulting reaction mixture was stirred at 25 °C for 1 h. After completion of the reaction, saturated aqueous ammonium chloride solution (100 mL) was added to the reaction mixture at 0-5 °C which then was extracted with ethyl acetate (30 mL). The ethyl acetate layer was washed with water (10 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain 2-(5-cyano-1H-indol-1-yl)acetate (8 g, 100 % yield). b) Step 2:- Ethyl 2-(5-(N’-hydroxycarbamimidoyl)-1H-indol-1-yl)acetate To a stirred solution of ethyl 2-(5-cyano-1H-indol-1-yl)acetate (8 g, 35 mmol) in ethanol (100 mL), hydroxylamine hydrochloride (3.6 g, 53 mmol) and sodium bicarbonate (4.7 g, 56 mmol) were added at 25 °C. The resulting reaction mixture was stirred at 55 °C for 16 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and filtered. The obtained solid was washed with ethanol (100 mL). The filtrate was concentrated under reduced pressure to obtain ethyl 2-(5-(N'- hydroxycarbamimidoyl)-1H-indol-1-yl)acetate (9 g, 98 % yield). c) Step 3: Ethyl 2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetate (compound no.1) To a stirred suspension of ethyl 2-(5-(N'-hydroxycarbamimidoyl)-1H-indol-1-yl)acetate (9 g, 34 mmol) in tetrahydrofuran (100 mL), trifluoroacetic anhydride (7.3 mL, 52 mmol) was added at 0-5 °C under nitrogen atmosphere and stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was poured slowly into a mixture of ethyl acetate (200 mL), sodium bicarbonate (20 g) and ice cold water (300 mL). The ethyl acetate layer was isolated, washed twice with saturated sodium bicarbonate solution (60 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude product. The obtained crude product was purified by column chromatography on silica gel using ethyl acetate in hexane as an eluent to obtain ethyl 2-(5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetate (4.5 g, 38 % yield). d) Step 4: N-(3,4-difluorophenyl)-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)acetamide To a stirred solution of ethyl 2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetate (0.2 g, 0.59 mmol) and 3,4-difluoroaniline (0.15 g, 1.18 mmol) in toluene (7 mL), 2M trimethylaluminium toluene (0.74 mL, 1.47 mmol) was added at 0-5 °C under nitrogen atmosphere, and the reaction mixture was stirred at 65 °C for 16 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and poured into a solution of 10 % aqueous acetic acid (7 mL) and ethyl acetate (15 mL). The resulting mixture was further stirred at 25 °C for 10 minutes. The ethyl acetate layer was isolated and the aqueous layer was again extracted with ethyl acetate (20 mL). The combined ethyl acetate layer was washed with water (20 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative HPLC to obtain N-(3,4-difluorophenyl)-2-(5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)acetamide (0.18 g, 73 % yield). The following compounds in table 1 were prepared by the procedure analogous to that of the example no.1. Table: 1
Figure imgf000071_0001
Figure imgf000072_0001
Example 2: Preparation of (4-(trifluoromethoxy)phenyl)(5-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-indol-1-yl)methanone (Compound 11) a) Step 1: Tert-butyl 5-cyano-1H-indole-1-carboxylate To a stirred solution of 5-cyanoindole (10 g, 70.3 mmol) in tetrahydrofuran (100 ml), 4- dimethylaminopyridine (4.30 g, 35 mmol) was added slowly. Boc-anhydride (19.6 mL, 84 mmol) was added drop wise at 0-5 °C, and the resulting reaction mixture was stirred at 25 °C for 4 h. After completion of the reaction, the product was extracted twice into ethyl acetate (200 mL). The combined ethyl acetate layer was washed twice with brine solution (100 mL), dried over anhydrous sodium sulphate, filtered and concentrated to obtain tert-butyl 5-cyano-1H-indole-1-carboxylate (16.5 g, 97 % yield). b) Step 2: Tert-butyl 5-(N'-hydroxycarbamimidoyl)-1H-indole-1-carboxylate To a stirred solution of tert-butyl 5-cyano-1H-indole-1-carboxylate (16.5 g, 68 mmol) in ethanol (107 mL), hydroxylamine hydrochloride (8.5 g, 123 mmol) and sodium bicarbonate (11.4 g, 136 mmol) were added successively at 25 °C. The resulting reaction mixture was stirred at 65 °C for 16 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and filtered. The obtained solid was washed with methanol (100 mL). The combined filtrate and washing solution was concentrated under reduced pressure. The residue was co-evaporated thrice with ethyl acetate (30 mL) to remove volatiles completely and to obtain tert-butyl 5-(N'-hydroxycarbamimidoyl)-1H-indole-1-carboxylate (18 g, 96 % yield). c) Step 3: Tert-butyl 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indole-1-carboxylate (Compound no.10) To a stirred solution of tert-butyl 5-(N’-hydroxycarbamimidoyl)-1H-indole-1-carboxylate (19 g, 68 mmol) in tetrahydrofuran (150 mL), trifluoroacetic anhydride (14.4 mL, 102 mmol) was added at 0-5 °C, and the resulting reaction mixture was stirred at 25 °C for 18 h. After completion of the reaction, the reaction mixture was poured into aqueous saturated sodium bicarbonate solution (400 mL) at 10 oC. The suspension was filtered, washed with water (100 mL) followed by hexane (50 mL) and dried under reduced pressure to obtain tert-butyl 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indole-1- carboxylate (23 g, 64 mmol, 94 % yield). d) Step 4: 3-(1H-indol-5-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole To a solution of tert-butyl 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indole-1-carboxylate (22 g, 62 mmol) in dichloromethane (100 mL), trifluoroacetic acid (34 mL, 436 mmol) was added at 0-5 °C under nitrogen atmosphere, and the reaction mixture was stirred at 25 °C for 4 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain 3-(1H-indol-5- yl)-5-(trifluoromethyl)-1,2,4-oxadiazole (14 g, 89 % yield). e) Step 5: (4-(Trifluoromethoxy)phenyl)(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)methanone (Compound no.11) To a stirred solution of 3-(1H-indol-5-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole (0.36 g, 1.42 mmol) in dichloromethane, 4-dimethylaminopyridine (0.035 g, 0.284 mmol) and triethylamine (0.495 mL, 3.6 mmol) were added at 25 °C, followed by the addition of 4-(trifluoromethoxy)benzoyl chloride (0.327 mL, 2.07 mmol) at 0-5 °C. The resulting reaction mixture was stirred at 25 °C for 16 h. After completion of the reaction, saturated aqueous sodium bicarbonate solution (10 mL) was added to the reaction mixture, which then was stirred for further 15 min. The dichloromethane layer was isolated, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude product. Methanol (5 mL) was added to the crude product and the resulting suspension was stirred for 1 h, filtered and washed with methanol (3 mL) and then with n-hexane (5 mL). The product was dried under reduced pressure to obtain (4-(trifluoromethoxy)phenyl)(5-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-indol-1-yl)methanone (0.45 g, 73 % yield). The following compounds in table 2 were prepared by the procedure analogous to that of the example no.2. Table: 2
Figure imgf000074_0001
Figure imgf000075_0001
Example 3: Preparation of N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)isobutyramide (Compound no.36) a) Step 1: tert-butyl (2-((5-cyano-2-nitrophenyl)amino)ethyl)carbamate To a stirred solution of 3-fluoro-4-nitrobenzonitrile (5 g, 30.1 mmol) in dimethyl sulfoxide (50 mL), N-1-Boc-1,2-diaminoethane (9.6 mL, 60.2 mmol) was added, followed by the addition of triethyl amine (6.3 mL, 45.2 mmol) at 25 oC. The reaction mixture was heated under stirring to 120 oC for 4 h. After completion of the reaction, the reaction mixture was cooled to 25 oC, water (200 mL) was added and the reaction mixture was filtered. The obtained solid was washed with water (50 mL) and dried to obtain tert-butyl (2-((5-cyano-2-nitrophenyl)amino)ethyl)carbamate (9.2 g, 100 % yield) as a yellow solid. b) Step 2: tert-butyl (2-((2-amino-5-cyanophenyl)amino)ethyl)carbamate To a stirred solution of tert-butyl (2-((5-cyano-2-nitrophenyl)amino)ethyl)carbamate (5 g, 16.3 mmol) in methanol (450 mL) and water (150 mL), iron (3.65 g, 65.3 mmol) and ammonium chloride (5.24 g, 98 mmol) were added at 25 oC, and the resulting reaction mixture was heated at 100 oC for 4 h. After completion of the reaction, the reaction mixture was filtered through celite and washed with methanol (100 mL). The filtrate was diluted with dichloromethane (200 mL) and sodium bicarbonate solution (50 mL). The organic layer was separated, washed with water (100 mL) and brine solution (50 mL). The organic layer was concentrated under reduced pressure to obtain tert-butyl (2-((2-amino-5- cyanophenyl)amino)ethyl)carbamate (4.28 g, 95 % yield) as brown solid. c) Step 3: tert-butyl (2-(6-cyano-1H-benzo[d]imidazol-1-yl)ethyl)carbamate To a stirred solution of tert-butyl (2-((2-amino-5-cyanophenyl)amino)ethyl)carbamate (4.28 g, 15.5 mmol) in ethanol (40 mL), triethyl orthoformate (5.16 ml, 31.0 mmol) and p-toluenesulfonic acid monohydrate (0.884 g, 4.6 mmol) were added at 25 oC. The reaction mixture was heated at 100 oC for 8 h. After completion of the reaction, the reaction mixture was cooled to 25 oC. Water (200 mL) and dichloromethane (100 mL) were added, followed by the addition of saturated sodium bicarbonate solution (50 mL). The organic layer was separated, washed with water (50 mL), saturated sodium bicarbonate solution (50 mL) and brine solution (50 mL). The organic layer was separated, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain tert-butyl (2-(6-cyano- 1H-benzo[d]imidazol-1-yl)ethyl)carbamate (3.6 g, 81 % yield) as solid. d) Step 4: tert-butyl (2-(6-(N'-hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1- yl)ethyl)carbamate To a stirred solution of tert-butyl (2-(6-cyano-1H-benzo[d]imidazol-1-yl)ethyl)carbamate (4.0 g, 13.9 mmol) in ethanol (50 mL), aqueous hydroxylamine solution (4.3 mL, 69.8 mmol) was added under nitrogen atmosphere. The reaction mixture was stirred at 65 oC for 16 h. After completion of the reaction, the volatiles were evaporated under reduced pressure to obtain tert-butyl (2-(6-(N'- hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1-yl)ethyl)carbamate (4.4 g, 99 % yield) as an off white solid. e) Step 5: tert-butyl (2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)carbamate (Compound no 30) To a stirred solution of tert-butyl (2-(6-(N'-hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1- yl)ethyl)carbamate (8 g, 25.1 mmol) in tetrahydrofuran (80 mL), 2,2,2-trifluoroacetic anhydride (6.01 mL, 42.6 mmol) was added drop wise at 5 oC during about 30 min. The reaction mixture was allowed to stir at 25 oC for 16 h. After completion of the reaction, the reaction mixture was quenched by addition of ice cold water (100 mL) and extracted with dichloromethane (200 mL). The organic layer was separated and washed with saturated sodium bicarbonate solution (50 mL), water (100 mL) and brine solution (50 mL). The organic layer was separated, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain tert-butyl (2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-benzo[d]imidazol-1-yl)ethyl)carbamate (9.9 g, 99 % yield) as a off white solid. 1H-NMR (400 MHz, DMSO-d6) δ 8.33 (d, 2H), 7.90 (dd, 1H), 7.83 (d, 1H), 6.99 (t, 1H), 4.39 (t, 2H), 3.35 (t, 2H), 1.14 (d, 9H), LCMS (M+H): 398.1. f) Step 6: 2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethan-1- amine hydrochloride To an ice cold stirred solution of tert-butyl (2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)carbamate (9 g, 22.6 mmol) in dichloromethane (100 mL), hydrochloric acid in dioxane (39.6 mL, 159 mmol) was added drop wise at 0 °C. The reaction mixture was stirred at 25 °C for 10 h. After completion of the reaction, dichloromethane was evaporated under reduced pressure to obtain 2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethan-1- amine hydrochloride (7.14 g, 94 % yield) as an off white solid. g) Step 7: N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)isobutyramide (compound no 36) To a stirred solution of 2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethan-1-amine hydrochloride (0.15 g, 0.4 mmol) in dichloromethane (5 mL), triethyl amine (0.157 mL, 1.124 mmol) and N,N-dimethylpyridin-4-amine (5.49 mg, 0.04 mmol) were added followed by the addition of isobutyryl chloride (0.048 ml, 0.5 mmol) in dichloromethane (1 mL), drop wise at 0 °C. The resulting reaction mixture was stirred at 0 oC to 25 °C for 1 h. After completion of the reaction, the reaction mixture was poured into water (10 mL) and extracted with dichloromethane (50 mL). The organic layer was washed with water (10 mL) and brine solution (10 mL), dried over anhydrous sodium sulfate. Organic layer was concentrated under reduced pressure. The residue was purified by preparative HPLC to obtain N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)isobutyramide (0.088 g, 53 % yield) as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ 8.34 (s, 1H), 8.30 (q, 1H), 7.91 (dd, 1H), 7.88-7.83 (m, 2H), 4.42 (t, 2H), 3.46 (q, 2H), 2.23-2.16 (m, 1H), 0.86 (d, 6H) LCMS (M+H): 368 The following compounds in table 3 were prepared by using the analogous procedure as described in example no.3. Table: 3
Figure imgf000078_0001
Figure imgf000079_0001
Figure imgf000080_0001
Example 4: Preparation of 1-(4-chlorophenyl)-3-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-benzo[d]imidazol-1-yl)ethyl)urea (compound no.64) To a stirred solution of 2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethan-1-amine hydrochloride (0.15 g, 0.5 mmol) in dichloromethane (3.0 mL), triethyl amine (0.063 mL, 0.5 mmol) was added, followed by 1-chloro-4-isocyanatobenzene (0.055 mL, 0.5 mmol) in dichloromethane (2 mL) at 0-5 oC during about 20 min under nitrogen atmosphere. The resulting reaction mixture was stirred at 0-5 oC to 25 oC for 30 min. After completion of the reaction, the reaction mixture was concentrated and purified by preparative HPLC to obtain 1-(4-chlorophenyl)-3- (2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)urea (0.099 g, 49 % yield) as a white solid 1HNMR (400 MHz, DMSO-d6) δ 8.64 (s, 1H), 8.44 (s, 1H), 8.37 (d, 1H), 7.94- 7.87 (m, 2H), 7.36-7.33 (m, 2H), 7.22 (dd, 1H), 6.30 (t, 1H), 4.50 (t, 2H), 3.54 (q, 2H) LCMS (M-H): 448.95. The following compounds in table 4 were prepared by using the analogous procedure as described in example no.4. Table: 4
Figure imgf000081_0001
Figure imgf000082_0001
Example 5: Preparation of 4-methoxy-N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)benzenesulfonamide Compound no 42) To a stirred solution of 2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethan-1-amine hydrochloride (0.15 g, 0.5 mmol) in dichloromethane (5 mL), triethylamine (0.157 mL, 1.1 mmol) and N,N-dimethylpyridin-4-amine (5.49 mg, 0.04 mmol) were added at 0 °C, followed by the drop wise addition of 4-methoxybenzenesulfonyl chloride (0.093 g, 0.5 mmol) in dichloromethane (1 mL) at the same temperature. The resulting mixture was stirred at 0 °C to 25 °C for 1 h. After completion of the reaction, the reaction mixture was extracted with dichloromethane (50 mL). The organic layer was washed with water (10 mL) twice and brine solution (10 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to get the crude compound, which was purified by preparative HPLC to obtain 4-methoxy-N-(2-(6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzenesulfonamide (0.094 g, 45 % yield) as a white solid.1H-NMR (400 MHz, DMSO-d6) δ 8.33 (s, 1H), 8.28 (d, 1H), 7.91 (dd, 1H), 7.83 (dd, 1H), 7.72 (t, 1H), 7.60 (dt, 2H), 6.98 (dt, 2H), 4.40 (t, 2H), 3.78 (s, 3H), 3.15 (q, 2H) LCMS (M+H): 468.15. The following compounds in table 5 were prepared by using the analogous procedure as described in example no.5. Table: 5
Figure imgf000083_0001
Figure imgf000084_0001
Example 6: Preparation of cyclopentyl (2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)carbamate (Compound no 57) To an ice cold stirred solution of 2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethan-1-amine hydrochloride (0.15 g, 0.5 mmol) in dichloromethane (5 mL), triethylamine (0.075 mL, 0.5 mmol) was added followed by the addition of triphosgene (0.147 g, 0.5 mmol), drop wise at 0 °C. The resulting reaction mixture was stirred at 0 °C for 1 h. After completion of the reaction, the reaction mixture was quenched by drop wise addition of cyclopentanol (2 mL) at 0 °C, and the mixture was allowed to warm up from 0 °C to 25 °C under stirring during 30 min. The reaction mixture was concentrated and purified by preparative HPLC to obtain cyclopentyl (2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)carbamate (0.043 g, 23 % yield) as a white solid.1H-NMR (400 MHz, DMSO-d6) δ 8.36 (s, 1H), 8.29 (d, 1H), 7.91 (dd, 1H), 7.85-7.83 (m, 1H), 7.17 (t, 1H), 4.82 (q, 2H),4.42-4.34 (m, 2H), 3.37 (q, 2H), 1.64 (t, 2H), 1.44-1.36 (m, 5H) LCMS (M+H): 410. The following compounds in table 6 were prepared by using the analogous procedure as described in example no.6. Table: 6
Figure imgf000084_0002
Figure imgf000085_0001
Example 7: Preparation of N-phenyl-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)acetamide (compound no.48) a) Step 1: tert-Butyl-(2-amino-5-cyanophenyl)glycinate To a stirred solution of 3,4-diaminobenzonitrile (10 g, 75 mmol) in N,N-dimethylformamide (50 mL)), cesium carbonate (24.47 g, 7 mmol) was added, and stirring was continued at 25 °C for 1 h. tert-Butyl-2-bromoacetate (12.12 mL, 8 mmol) was added, and the resulting reaction micture was stirred at 25 °C for 18 h. After completion of the reaction, the reaction mixture was diluted with dichloromethane (100 mL), washed twice with water (100 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude product. The obtained crude product was purified by flash column chromatography to get pure tert-butyl-(2-amino-5-cyanophenyl)glycinate (12.07 g, 65 % yield). b) Step 2: tert-Butyl-2-(6-cyano-1H-benzo[d]imidazol-1-yl)acetate To a stirred solution of tert-butyl-(2-amino-5-cyanophenyl)glycinate (10.5 g, 42.5 mmol) in ethanol (50 mL) at 25 °C, triethyl orthoformate (14.14 mL, 8 mmol) and p-toluenesulfonic acid monohydrate (0.808 g, 4.3 mmol) were added, and the resulting reaction mixture was stirred at 60 °C for 18 h. The reaction mixture was cooled to 25 °C, diluted with dichloromethane (100 mL) and washed with saturated sodium bicarbonate solution (100 mL), then dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude product. The obtained crude product was washed with diethyl ether to get tert-butyl-2-(6-cyano-1H-benzo[d]imidazol-1-yl)acetate (10.05 g, 39.1 mmol, 92% yield). c) Step 3: tert-Butyl-2-(6-(N'-hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1-yl)acetate To a stirred solution of tert-butyl-2-(6-cyano-1H-benzo[d]imidazol-1-yl)acetate (8.8 g, 34.2 mmol) in ethanol (50 mL), hydroxylamine solution 50 wt.% in water (7.91 mL, 120 mmol) was added at 25 °C and stirred at 60 °C for 6 h. After completion of the reaction, the resulting reaction mixture was directly concentrated to obtain of tert-butyl-2-(6-(N'-hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1- yl)acetate (8.94 g, 90 % yield). d) Step 4: tert-Butyl-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)acetate (compound no.26) To a stirred solution of tert-butyl-2-(6-(N'-hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1-yl)acetate (9.9 g, 34.1 mmol) in tetrahydrofuran (15 mL), 2,2,2-trifluoroacetic anhydride (8.54 mL, 61.4 mmol) was added slowly at 0-5 °C under nitrogen atmosphere, and the resulting mixture was stirred for 18 h at 25 °C. After completion of the reaction, the resulting reaction mixture was suspended in 50 mL ethyl acetate and washed with aqueous sodium bicarbonate solution (50 mL). The ethyl acetate layer was isolated, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain tert-butyl-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetate (11 g, 88 % yield).1H-NMR (400 MHz, DMSO-d6) δ 8.38 (d, 1H), 8.31 (dd, 1H), 7.92 (dd, 1H), 7.86 (dd, 1H), 5.29 (s, 2H), 1.44 (s, 9H). e) Step 5: 2-(6-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetic acid To a stirred solution of tert-butyl-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)acetate (5.2 g, 14.1 mmol) in tetrahydrofuran (20 mL) and water (6.00 mL) mixture, concentrated hydrochloric acid (5 mL) was added slowly at 0-5 °C, and the resulting reaction mixture was stirred for 8 h at 60 °C. After completion of the reaction, the reaction mixture was poured into ice cold water. The obtained precipitate was filtered and dried under vacuum to afford 2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetic acid (4.1 g, 93 % yield). 1H- NMR (400 MHz, DMSO-d6) δ 8.43 (s, 1H), 8.33 (d, 1H), 7.94 (dd, 1H), 7.87 (d, 1H), 5.31 (s, 2H). f) Step 6: N-phenyl-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)acetamide (compound no.48) To a stirred solution of 2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)acetic acid (0.25 g, 0.8 mmol) in dichloromethane (15 mL)), N,N-dimethylaminopyridine (0.215 g, 1.8 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.338 g, 1.8 mmol) and aniline (0.089 g, 0.9 mmol) were added at 0-5 °C under nitrogen atmosphere, and the resulting reaction mixture was stirred at 25 °C for 18 h. After completion of the reaction, the reaction mixture was diluted in dichloromethane (20 mL), washed twice with water (30 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude product was purified by prep- HPLC to obtain pure N-phenyl-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol- 1-yl)acetamide (0.122 g, 39% yield). 1H-NMR (400 MHz, DMSO-d6) δ 10.49 (s, 1H), 8.45-8.42 (m, 1H), 8.33 (q, 1H), 7.99-7.92 (m, 1H), 7.88 (dd, 1H), 7.59 (dd, 2H), 7.33-7.29 (m, 2H), 7.08-7.04 (m, 1H), 5.34 (s, 2H). The following compounds in table 7 were prepared by using the procedure analogous to that of the example no.7. Table: 7
Figure imgf000087_0001
Figure imgf000088_0001
Figure imgf000089_0001
Example 8: Preparation of N-Phenyl-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)acetamide (compound no.90): a) Step 1: tert-Butyl-(2-amino-4-bromophenyl)glycinate tert-Butyl-(2-amino-4-bromophenyl)glycinate was synthesized by using similar experimental procedure of step-1 of example 1 (2.71 g, 21 % yield). b) Step 2: tert-Butyl-2-(5-bromo-1H-benzo[d]imidazol-1-yl)acetate tert-Butyl-2-(5-bromo-1H-benzo[d]imidazol-1-yl)acetate was synthesized by using similar experimental procedure of step-1 of example 1 (4.2 g, 81 % yield). c) Step 3: tert-Butyl-2-(5-cyano-1H-benzo[d]imidazol-1-yl)acetate To a stirred solution of tert-butyl 2-(5-bromo-1H-benzo[d]imidazol-1-yl)acetate (3.5 g, 11.3 mmol) in dioxane (15 mL), water (6 mL) and under nitrogen atmosphere, Pd(Xanphos)allylCl (0.408 g, 0.6 mmol), potassium acetate (0.552 g, 5.6 mmol) and potassium hexacyanoferrate(II) trihydrate (2.61 g, 6.2 mmol) were added, the resulting reaction mixture was degassed for 5 min and then allowed to stir for 12 h at 90 °C. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (25 mL) and washed with water. The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude residue was purified by flash column chromatography (eluent 0-20 % ethyl acetate in hexane) to obtain tert-butyl-2-(5-cyano-1H-benzo[d]imidazol-1- yl)acetate (2.6 g, 90 % yield). d) Step 4: tert-Butyl-2-(5-(N'-hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1-yl)acetate tert-Butyl-2-(5-(N'-hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1-yl)acetate was synthesized by using similar experimental procedure of step-1 of example 1 (2.54 g, 81 % yield). e) Step 5: tert-Butyl-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)acetate (compound no.58) tert-Butyl-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetate was synthesized by using similar experimental procedure of step-1 of example 1 (3.1 g, 87 % yield). 1H- NMR (400 MHz, DMSO-d6) δ 8.37 (s, 1H), 8.32 (s, 1H), 7.97 (dd, 1H), 7.77 (d, 1H), 5.22 (s, 2H), 1.42 (s, 9H). f) Step 6: 2-(5-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetic acid 2-(5-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetic acid was synthesized by using similar experimental procedure of step-1 of example 1 (2.2 g, 81 % yield). 1H- NMR (400 MHz, DMSO-d6) δ 8.37 (s, 1H), 8.32 (d, 1H), 7.96 (dd, 1H), 7.79 (d, 1H), 5.21 (s, 2H). g) Step 7: N-Phenyl-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)acetamide (compound no.90) N-Phenyl-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetamide was synthesized by using similar experimental procedure of step-1 of example 1 (0.088 g, 28 % yield).1H- NMR (400 MHz, DMSO-d6) δ 10.49 (s, 1H), 8.42 (s, 1H), 8.34 (t, 1H), 7.98 (dd, 1H), 7.79 (dd, 1H), 7.59 (dd, 2H), 7.34-7.30 (m, 2H), 7.09-7.05 (m, 1H), 5.27 (s, 2H); LCMS (M+H): 388.00. The following compounds in table 8 were prepared by using the procedure analogous to that of the example no.8. Table: 8
Figure imgf000090_0001
Figure imgf000091_0001
Example 9: Preparation of N-(2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)nicotinamide (compound 94) a) Step 1: tert-butyl (2-((4-cyano-2-nitrophenyl)amino)ethyl)carbamate To a stirred solution of 4-fluoro-3-nitrobenzonitrile (8 g, 48.2 mmol) in dimethylsufoxide (80 mL), N- 1-Boc-1,2-diaminoethane (10.03 mL, 62.6 mmol) was added at 25 oC followed by addition of triethylamine (10.07 mL, 72.2 mmol) at 25 oC. The resulting reaction mixture was heated to 120 oC for 4 h. The reaction mixture was cooled to 25 oC and water (200 mL) was added slowly with stirring. The obtained precipitate was filtered, washed with water (50 mL) and suction dried to obtain tert- butyl (2-((4-cyano-2-nitrophenyl)amino)ethyl)carbamate (13 g, 88 % yield). b) Step 2: tert-butyl (2-((2-amino-4-cyanophenyl)amino)ethyl)carbamate To a stirred solution of tert-butyl (2-((4-cyano-2-nitrophenyl)amino)ethyl)carbamate (10 g, 32.6 mmol) in methanol (75 mL) and water (25 mL), iron (7.29 g, 131 mmol) and ammonium hydrochloride (10.48 g, 196 mmol) were added at 25 oC. The resulting reaction mixture was stirred at 70 oC for 4 h. The reaction mixture was cooled to 25 oC, filtered through celite bed and washed with methanol (20 mL). The dichloromethane (100 mL) was added to the obtained filtrate and stirred at 25 oC for 10 min. The dichloromethane layer are isolated, washed with brine (20 mL) and concentrated to obtain tert-butyl (2-((2-amino-4-cyanophenyl)amino)ethyl)carbamate (8 g, 89 % yield). c) Step 3: tert-butyl (2-(5-cyano-1H-benzo[d]imidazol-1-yl)ethyl)carbamate To a stirred solution of tert-butyl (2-((2-amino-4-cyanophenyl)amino)ethyl)carbamate ( 11.5 g, 41.6 mmol) in toluene (50 mL), triethyl orthoformate (10.39 mL, 62.4 mmol) and p-toluenesulfonic acid monohydrate (1.583 g, 8.32 mmol) were added at 25 oC. The resulting reaction mixture was stirred at 100 oC for 4 h. The reaction mixture was cooled to 25 oC, dichloromethane (40 mL) and aqueous saturated sodium bicarbonate solution (45 mL) were added. The dichloromethane layer was separated, washed with water (15 mL), aqueous saturated sodium bicarbonate solution (10 mL) and brine (10 mL). The dichloromethane layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain tert-butyl (2-(5-cyano-1H-benzo[d]imidazol-1-yl)ethyl)carbamate (10 g, 84 % yield). d) Step 4: tert-butyl (2-(5-(N'-hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1- yl)ethyl)carbamate To a stirred solution of tert-butyl (2-(6-cyano-1H-benzo[d]imidazol-1-yl)ethyl)carbamate (7.5 g, 26.2 mmol) in ethanol (10 mL), 50 % aqueous hydroxylamine solution (8.03 mL, 131 mmol) was added under nitrogen atmosphere. The resulting reaction mixture was stirred at 65 oC for 5 h. The volatiles were removed under reduced pressure and obtained residue was co-evaporated with toluene two times to obtain tert-butyl (2-(5-(N'-hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1-yl)ethyl)carbamate (7 g, 84 % yield). e) Step 5: tert-butyl (2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)carbamate To a stirred solution of tert-butyl (2-(6-(N'-hydroxycarbamimidoyl)-1H-benzo[d]imidazol-1- yl)ethyl)carbamate (7.5 g, 23.48 mmol) in tetrahydrofuran (5 mL), trifluoroacetic acid (5.97 mL, 42.3 mmol) was added drop wise at 5 oC and the resulting reaction mixture was stirred at 25 oC for 16 h. The reaction mixture was poured into a mixture of ice cold water (20 mL) and dichloromethane (30 mL). The dichloromethane layer was isolated, washed with aqueous saturated sodium bicarbonate solution (15 mL), water (20 mL) and brine (20 mL). The dichloromethane layer was dried over sodium sulphate and concentrated under reduced pressure to obtain tert-butyl (2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)carbamate (5 g, 54 % yield). f) Step 5: 2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethan-1- amine hydrochloride To a stirred solution of tert-butyl (2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)carbamate (5 g, 12.58 mmol) in dichloromethane (10 mL), 4M hydrochloric acid in 1, 4-dioxane (22.02 mL, 88 mmol) was added at 0 oC. The resulting reaction mixture was stirred at 25 °C for 3 h. The volatiles were removed under reduced pressure to obtain 2- (6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethan-1-amine hydrochloride (4 g, 95 % yield). g) Step 6: N-(2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)nicotinamide (compound 94) To a stirred solution of 2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethan-1-amine hydrochloride (250 mg, 0.75 mmol) in N,N-dimethylformamide (10 mL), triethylamine (0.285 mL, 2.043 mmol) was added at 25 °C followed by addition of nicotinic acid (84 mg, 0.681 mmol) and 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (388 mg, 1.022 mmol). The resulting reaction mixture was stirred for 12 h at 25 °C. After completion of the reaction, ice-cold water (20 mL) was added and the product was extracted into ethyl acetate (30 mL). The ethyl acetate layer was isolated and concentrated under reduced pressure to obtain crude product. The obtained crude product was purified by preparative HPLC to obtain N-(2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)nicotinamide (160 mg, 58 % yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.81-8.85 (m, 2H), 8.67 (dd, 1H), 8.40 (s, 1H), 8.29 (d, 1H), 8.02-8.05 (m, 1H), 7.93 (dd, 1H), 7.84-7.86 (m, 1H), 7.46 (ddd, 1H), 4.52 (t, 2H), 3.71 (q, 2H); LCMS (M+1): 402.65. The following compounds in table 9 were prepared by using the procedure analogous to that of the example no.9. Table: 9
Figure imgf000093_0001
Example 10: Preparation of N-(2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)cyclopropanesulfonamide (compound 99) To a stirred solution of 2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethan-1-amine hydrochloride (300 mg, 0.899 mmol) in dichloromethane (5.0 mL), triethylamine (0.313 mL, 2.248 mmol) was added followed by addition of cyclopropanesulfonyl chloride (0.101 mL, 0.989 mmol) drop wise at 0 °C. The resulting reaction mixture was stirred at 25 °C for 1 h. The volatiles were removed under reduced pressure to obtain crude product. The obtained crude product was purified by preparative HPLC to obtain N-(2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)cyclopropanesulfonamide (130 mg, 36 % yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.38 (s, 1H), 8.1 (bs, 1H), 7.99-7.97 (dd, 1H), 7.87- 7.85 (d, 1H), 4.41 (t, 2H), 3.46-3.41 (q, 2H), 0.82-0.80 (m, 4H); LCM (M+H): 401.65. The following compounds in table 10 were prepared by using the procedure analogous to that of the example no.10. Table: 10
Figure imgf000094_0001
BIOLOGY EXAMPLES: Green House Test Example 1: Phakopsora pachyrhizi test in Soybean Compounds were dissolved in 2 % dimethyl sulfoxide/Acetone and then diluted with water containing emulsifier to the desired test concentration. To test the preventive activity of compounds, healthy young soybean plants, raised in the greenhouse, were sprayed with the active compound solution at the stated application rates inside spray cabinets using hallowcone nozzles. One day after treatment, the plants were inoculated with a suspension containing 2.1x106 Phakopsora pachyrhizi spores. The inoculated plants were then kept in the greenhouse chamber at 25 oC temperature and 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 compounds 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 compatibility by recording symptoms like necrosis, chlorosis and stunting. Compounds 1 2 3 4 6 7 8 9 10 11 12 13 14 15 16 17 18 19 21 22 23 24 26 28 29 31 37 38 40 42 43 44 45 46 47 48 49 57 59 showed >70 % at 500 ppm control in these tests when compared to the untreated check which showed extensive disease development.

Claims

CLAIMS: 1) A compound formula (I),
Figure imgf000096_0001
Formula (I) wherein, R1 is C1-C2-haloalkyl; R2 and R3 are independently selected from the group consisting of hydrogen, halogen, cyano, C1-C6 alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6- haloalkoxy, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylsulfinyl and C1- C6-alkylsulfonyl; R2 and R3 are optionally and independently may be substituted with halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl or C1-C6-alkoxy; (iii) A1 is CR7; and R4 and R7 are independently 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 and C1-C6- alkylsulfonyl; R4 may be optionally substituted with halogen, cyano, amino, C1-C6-alkylamino, C1-C6- dialkylamino, C1-C6-trialkylamino, C1-C6-alkyl, or C1-C6-alkoxy; or (iv) A1 is N and R4 is hydrogen; Q is selected from the group consisting of Q1 to Q11;
R10 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl; R11 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, -(CR12R13)0-4C3-C6-non-aromatic carbocyclyl ring, -(CR12R13)0-4C6-C10-aromatic carbocyclyl ring, -(CR12R13)0-4C3-C6-non-aromatic heterocyclyl ring, -(CR12R13)0-4C6-C10-aromatic heterocyclyl ring, -S(O)0-2C3-C6-non-aromatic carbocyclyl ring, -S(O)0-2C6-C10-aromatic carbocyclyl ring, -S(O)0-2C3-C6-non-aromatic heterocyclyl ring, and -S(O)0-2C6-C10-aromatic heterocyclyl ring; or R10 and R11 together the atom to which they are attached may form fused or non-fused 4-8 membered heterocyclic ring containing at least one heteroatom selected from O, S(=O)0-2, or NR14; R14 is selected from the group consisting of hydrogen, C1-6-alkyl and C3-6-cycloalkyl; R12 and R13 are independently selected from the group consisting of hydrogen, halogen, methyl, ethyl, propyl, isopropyl, difluoromethyl, trifluoromethyl, methoxy and ethoxy; R11 may be optionally substituted with halogen, cyano, amino, C1-C6-alkylamino, C1-C6 dialkylamino, C1-C6-trialkylamino, C1-C6-alkyl, or C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6- cycloalkyl, C3-C6-cycloalkoxy and phenoxy; or N-oxides, metal complexes, isomers, polymorphs or the 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 and R3 are independently selected from the group consisting of hydrogen, halogen, cyano, C1-C6 alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl and C1-C6-haloalkoxy; A1 is CR7; and R4 and R7 are independently selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy and C1-C6-haloalkyl; R11 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, -(CR12R13)0-4C3-C6-non-aromatic carbocyclyl ring, -(CR12R13)0-4C6-C10-aromatic carbocyclyl ring, -(CR12R13)0-4C3-C6-non-aromatic heterocyclyl ring, and -(CR12R13)0-4C6-C10-aromatic heterocyclyl ring; R10 and R11 together the atom to which they are attached may form fused or non-fused 4-8 membered heterocycle containing at least one heteroatom selected from O, S(=O)0-2, or NR14; R14 is selected from the group consisting of hydrogen, C1-6-alkyl and C3-6-cycloalkyl; R11 may be optionally substituted with halogen, cyano, amino, C1-C6 alkylamino, C1-C6 dialkylamino, C1-C6-trialkylamino, C1-C6-alkyl, or C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6- cycloalkyl, C3-C6-cycloalkoxy and phenoxy, R12 and R13 are independently selected from the group consisting of hydrogen, halogen, methyl, ethyl and propyl. 3) The compound of formula (I) according to claim 1, wherein R1 is selected from the group consisting of -CF3, -CHF2 and -CF2Cl; R2 and R3 are independently selected from the group consisting of hydrogen, halogen, cyano and C1-C6 alkyl; A1 is CR7; and R4 and R7 are independently selected from the group consisting of hydrogen, halogen and C1-C6-alkyl; R10 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6 alkoxy, and C1-C6-haloalkyl; R11 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, -(CR12R13)0-4C3-C6-non-aromatic carbocyclyl ring, -(CR12R13)0-4C6-C10-aromatic carbocyclyl ring, -(CR12R13)0-4C3-C6-non-aromatic heterocyclyl ring and -(CR12R13)0-4C6-C10-aromatic heterocyclyl ring; R10 and R11 together the atom to which they are attached may form fused or non-fused 4-8 membered heterocycle containing at least one heteroatom selected from O, S(=O)0-2, or NR14; R14 is selected from the group consisting of hydrogen, C1-6-alkyl and C3-6-cycloalkyl; R11 may be optionally substituted with halogen, cyano, amino, C1-C6-alkylamino, C1-C6 dialkylamino, C1-C6-trialkylamino, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C3-C6- cycloalkyl, C3-C6-cycloalkoxy and phenoxy; R12 and R13 are independently selected from the group consisting of hydrogen, halogen, methyl, ethyl, propyl, isopropyl, difluoromethyl, trifluoromethyl, methoxy and ethoxy. 4) The compound of formula (I) according to claim 1, wherein said compound of formula (I) is selected from ethyl 2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetate, N-(3,4- difluorophenyl)-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-inol-1-yl)acetamide, 2-(5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N-(4-(trifluoromethyl)phenyl)acetamide, N-(2-fluorophenyl)-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N- (pyridin-3-yl)-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(3- fluorophenyl)-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(3- methoxyphenyl)-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N- methyl-N-(2-phenoxyethyl)-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)acetamide, N-methyl-N-phenyl-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)acetamide, tert-butyl 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indole-1-carboxylate, (4- (trifluoromethoxy)phenyl)(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (3-chloro-4-fluorophenyl)(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (2-fluorophenyl)(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (4- chloro-2-fluorophenyl)(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (3,4-difluorophenyl)(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (2- chloro-6-fluorophenyl)(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, p- tolyl(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)(4-(trifluoromethyl)phenyl)methanone, (3- fluorophenyl)(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, N-(m- tolyl)-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, (3- methoxyphenyl)(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (3- bromophenyl)(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, 1-(5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, cyclobutyl(5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, 1-ethyl-3-(2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)urea, tert-Butyl-2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetate, N-(2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)cyclopropanesulfonamide, N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)ethanesulfonamide, N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-benzo[d]imidazol-1-yl)ethyl)methanesulfonamide, tert-butyl (2-(6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)carbamate, 4-fluoro-N-(2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzamide, N-(2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzamide, 1-(p-tolyl)-3- (2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)urea, N-(2-(6- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzenesulfonamide, 4-methyl-N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)benzenesulfonamide, N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)isobutyramide , 1-(2-methoxyphenyl)-3-(2-(6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)urea, N-(2-(6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)acetamide, N-(2-(6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)cyclopropanecarboxamide, 2,6-dimethyl-N-(2- (6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzamide, 2- chloro-6-methyl-N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)benzamide, 4-methoxy-N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)benzenesulfonamide, 4-fluoro-N-(2-(6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzenesulfonamide, methyl (2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)carbamate, N-(2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)thiazole-4-carboxamide, 4-methoxy-N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)benzamide, N-(4-fluorophenyl)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)acetamide, N-phenyl-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)acetamide, N-(thiazol-2-yl)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-benzo[d]imidazol-1-yl)acetamide, 1-(2-oxa-7-azaspiro[3.5]nonan-7-yl)-2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethan-1-one, 1-(2-oxa-6- azaspiro[3.3]heptan-6-yl)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol- 1-yl)ethan-1-one, 1-morpholino-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethan-1-one, N-(2-fluorophenyl)-2-(6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetamide, N-(3-methoxybenzyl)-2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetamide, N-(pyridin-3-yl)-2- (6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetamide, N-(pyridin-4- ylmethyl)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetamide, cyclopentyl (2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)carbamate, tert-Butyl-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)acetate, 1-phenyl-3-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)urea, 4-fluorobenzyl (2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-benzo[d]imidazol-1-yl)ethyl)carbamate, 3-fluoro-N-(2-(6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzenesulfonamide , 2,4-difluoro-N-(2- (6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)benzenesulfonamide, 2-fluoro-N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)benzenesulfonamide, 1-(4-chlorophenyl)-3-(2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)urea, 1-benzyl-3-(2-(6- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)urea, 1-(2- fluorophenyl)-3-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)urea, 1-(2,4-difluorophenyl)-3-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)urea, 1-(cyclopropylmethyl)-3-(2-(6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)urea, 1-isopropyl-3-(2-(6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)urea, 1-cyclopropyl-3-(2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)urea, 3-fluoro-N-(2-(6- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzamide, 4-methyl- N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzamide, N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)cyclobutanecarboxamide, N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)pivalamide, N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)ethyl)propionamide, 4-(trifluoromethyl)-N-(2-(6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzamide, 4-chloro-N-(2-(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzamide, 3,5-difluoro- N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzamide, 2- fluoro-N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)benzamide, N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)oxazole-4-carboxamide, 2,4-difluoro-N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-benzo[d]imidazol-1-yl)ethyl)benzamide, N-(2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-benzo[d]imidazol-1-yl)ethyl)nicotinamide, N-(methyl(oxo)(pyridin-2-yl)-λ6-sulfaneylidene)- 2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetamide, N- (methyl(oxo)(4-(trifluoromethyl)pyridin-2-yl)-λ6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetamide, N-((4-chlorophenyl)(methyl)(oxo)-λ6- sulfaneylidene)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)acetamide, N-(4-oxido-1,4-λ6-oxathian-4-ylidene)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-benzo[d]imidazol-1-yl)acetamide, N-((3-fluorophenyl)(methyl)(oxo)-λ6-sulfaneylidene)-2- (6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetamide, N-((4-fluoro- 2-methoxyphenyl)(methyl)(oxo)-λ6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-benzo[d]imidazol-1-yl)acetamide, N-((3-methoxybenzyl)(methyl)(oxo)-λ6- sulfaneylidene)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)acetamide, N-Phenyl-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)acetamide, N-(4-fluorophenyl)-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- benzo[d]imidazol-1-yl)acetamide, N-(pyridin-3-yl)-2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-benzo[d]imidazol-1-yl)acetamide, N-(3-methoxybenzyl)-2-(5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)acetamide, N-(2-(5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)isobutyramide, N-(2-(5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzamide, 4-chloro-N-(2-(5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzamide, 4-fluoro-N- (2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzamide, N- (2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1- yl)ethyl)cyclopropanesulfonamide, 2-methyl-N-(2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-benzo[d]imidazol-1-yl)ethyl)benzenesulfonamide, 4-methoxy-N-(2-(5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)benzenesulfonamide, N-(2-(5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)methanesulfonamide, N- (2-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)nicotinamide, 1-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)propan-1-one, N-(2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-2-phenylacetamide, N-(4- chlorophenyl)-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-isopropyl-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(2-fluoro-5-methoxyphenyl)-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)acetamide, isoxazol-4-yl(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)methanone, (3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)(p- tolyl)methanone, 1-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-2-(4- (trifluoromethyl)phenyl)ethan-1-one, (3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)(phenyl)methanone, 1-(4-methoxyphenyl)-N-(2-(3-methyl-5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)methanesulfonamide, 4-methyl-N-(2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzenesulfonamide, oxetan-3-yl(6- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, 1-(6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, cyclopropyl(6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)methanone, cyclopentyl(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)methanone, cyclobutyl(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol- 1-yl)methanone, 2-methyl-1-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)propan- 1-one, 2-phenyl-1-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 2-(p- tolyl)-1-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 2-(4- fluorophenyl)-1-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 2-(4- methoxyphenyl)-1-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 1-(6- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-2-(4-(trifluoromethyl)phenyl)ethan-1- one, 2-(4-chlorophenyl)-1-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1- one, 2-methoxy-1-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)propan-1-one, 2- (pyridin-3-yl)-1-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 2- (pyrimidin-5-yl)-1-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, phenyl(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (4- fluorophenyl)(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (4- chlorophenyl)(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, p-tolyl(6- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, 2-(2,4-difluorophenyl)-1-(6- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, (2-fluorophenyl)(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (1-methyl-1H-pyrazol-4-yl)(6- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, isoxazol-4-yl(6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (1-methyl-1H-pyrazol-3-yl)(6- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (2-fluoro-5- methoxyphenyl)(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, N-(2-(3- methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)ethanesulfonamide, N- (2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)oxetane-3- sulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)methanesulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethyl)cyclopropanesulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)cyclopentanesulfonamide, N-(2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)cyclobutanesulfonamide, N-(2-(3- methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)propane-2-sulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1- phenylmethanesulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethyl)-1-(p-tolyl)methanesulfonamide, 1-(4-fluorophenyl)-N-(2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)methanesulfonamide, 1-(4- methoxyphenyl)-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)methanesulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethyl)-1-(4-(trifluoromethyl)phenyl)methanesulfonamide, 1-(4-chlorophenyl)-N-(2-(3- methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)methanesulfonamide, 1- methoxy-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)ethane-1-sulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethyl)-1-(pyridin-3-yl)methanesulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1-(pyrimidin-5-yl)methanesulfonamide, N-(2-(3- methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzenesulfonamide, 4- fluoro-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)benzenesulfonamide, 4-chloro-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)ethyl)benzenesulfonamide, 4-methyl-N-(2-(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzenesulfonamide, 1-(2,4-difluorophenyl)-N-(2-(3- methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)methanesulfonamide, 2- fluoro-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)benzenesulfonamide, 1-methyl-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)ethyl)-1H-pyrazole-4-sulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)isoxazole-4-sulfonamide, 1-methyl-N-(2-(3-methyl-6- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1H-pyrazole-3-sulfonamide, 2- fluoro-5-methoxy-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)benzenesulfonamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethyl)propionamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethyl)oxetane-3-carboxamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-indol-1-yl)ethyl)acetamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)ethyl)cyclopropanecarboxamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)cyclopentanecarboxamide, N-(2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)cyclobutanecarboxamide, N-(2-(3- methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)isobutyramide, N-(2-(3- methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-2-phenylacetamide, N- (2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-2-(p- tolyl)acetamide, 2-(4-fluorophenyl)-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)ethyl)acetamide, 2-(4-methoxyphenyl)-N-(2-(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)acetamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-2-(4-(trifluoromethyl)phenyl)acetamide, 2-(4- chlorophenyl)-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)acetamide, 2-methoxy-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethyl)propanamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethyl)-2-(pyridin-3-yl)acetamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-2-(pyrimidin-5-yl)acetamide, N-(2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzamide, 4-fluoro-N-(2-(3-methyl- 6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzamide, 4-chloro-N-(2-(3- methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzamide, 4-methyl-N- (2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzamide, 2-(2,4- difluorophenyl)-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)acetamide, 2-fluoro-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethyl)benzamide, 1-methyl-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)ethyl)-1H-pyrazole-4-carboxamide, N-(2-(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)isoxazole-4-carboxamide, 1-methyl-N-(2-(3-methyl-6- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1H-pyrazole-3-carboxamide, 2- fluoro-5-methoxy-N-(2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)benzamide, N-ethyl-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol- 1-yl)acetamide, 2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N- (oxetan-3-yl)acetamide, N-methyl-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)acetamide, N-cyclopropyl-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)acetamide, N-cyclopentyl-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)acetamide, N-cyclobutyl-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)acetamide, N-isopropyl-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)acetamide, N-benzyl-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)acetamide, 2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)-N-(4-methylbenzyl)acetamide, N-(4-fluorobenzyl)-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(4-methoxybenzyl)-2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, 2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N-(4-(trifluoromethyl)benzyl)acetamide, N-(4-chlorobenzyl)-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)acetamide, 2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N- (pyridin-3-ylmethyl)acetamide, 2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)-N-(pyrimidin-5-ylmethyl)acetamide, 2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)-N-phenylacetamide, N-(4-fluorophenyl)-2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(4-chlorophenyl)-2-(3- methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, 2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N-(p-tolyl)acetamide, N-(2,4- difluorobenzyl)-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)acetamide, N-(2-fluorophenyl)-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)acetamide, N-(1-methyl-1H-pyrazol-4-yl)-2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(isoxazol-4-yl)-2-(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(1-methyl-1H-pyrazol-3-yl)-2-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(2-fluoro-5-methoxyphenyl)- 2-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(2-(3- methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)cyclopentanecarboxamide, 4-chloro-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-2-(pyridin-3-yl)acetamide, N-(2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)oxetane-3-carboxamide, 2-(4- methoxyphenyl)-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)acetamide, 2-(4-chlorophenyl)-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)ethyl)acetamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)ethyl)propionamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)ethyl)-2-(4-(trifluoromethyl)phenyl)acetamide, 2-(4-fluorophenyl)-N-(2-(3-methyl- 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)acetamide, N-(2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-2-(p-tolyl)acetamide, N-(2-(3- methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)acetamide, N-(2-(3- methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)cyclopropanecarboxamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)ethyl)isobutyramide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)ethyl)cyclobutanecarboxamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)isoxazole-4-carboxamide, 1-methyl-N-(2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1H-pyrazole-4-carboxamide, 1- methyl-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1H- pyrazole-3-carboxamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol- 1-yl)ethyl)benzamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)-2-(pyrimidin-5-yl)acetamide, 4-fluoro-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzamide, 4-methyl-N-(2-(3-methyl-5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzamide, 2-(2,4-difluorophenyl)-N-(2-(3-methyl-5- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)acetamide, 2-fluoro-N-(2-(3- methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzamide, 2-fluoro-5- methoxy-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)benzamide, N-cyclopentyl-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)acetamide, 2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N- (pyridin-3-ylmethyl)acetamide, 2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)-N-(oxetan-3-yl)acetamide, N-(4-methoxybenzyl)-2-(3-methyl-5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(4-chlorobenzyl)-2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-ethyl-2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, 2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N-(4-(trifluoromethyl)benzyl)acetamide, N-(4-fluorobenzyl)-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)acetamide, N-benzyl-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)acetamide, 2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N-(4- methylbenzyl)acetamide, N-methyl-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)acetamide, N-cyclopropyl-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)acetamide, N-cyclobutyl-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)acetamide, N-(1-methoxyethyl)-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(isoxazol-4-yl)-2-(3-methyl-5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(1-methyl-1H-pyrazol-4-yl)-2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, N-(1-methyl-1H-pyrazol-3-yl)- 2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)acetamide, 2-(3-methyl- 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N-phenylacetamide, 2-(3-methyl-5- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N-(pyrimidin-5-ylmethyl)acetamide, N- (4-fluorophenyl)-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)acetamide, 2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-N-(p- tolyl)acetamide, N-(2,4-difluorobenzyl)-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)acetamide, N-(2-fluorophenyl)-2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-indol-1-yl)acetamide, cyclopentyl(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)methanone, 4-chlorophenyl)(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-indol-1-yl)methanone, 1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)-2-(pyridin-3-yl)ethan-1-one, (3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)(oxetan-3-yl)methanone, 2-(4-methoxyphenyl)-1-(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 2-(4-chlorophenyl)-1-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, 1-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)propan-1-one, 1-(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-2-(4-(trifluoromethyl)phenyl)ethan-1-one, 2-(4-fluorophenyl)-1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan- 1-one, 1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-2-phenylethan-1- one, 1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-2-(p-tolyl)ethan-1- one, 1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, cyclopropyl(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, 2- methyl-1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)propan-1-one, cyclobutyl(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, 2- methoxy-1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)propan-1-one, (1-methyl-1H-pyrazol-4-yl)(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)methanone, (1-methyl-1H-pyrazol-3-yl)(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)methanone, (3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)(phenyl)methanone, 1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)- 2-(pyrimidin-5-yl)ethan-1-one, (4-fluorophenyl)(3-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)-1H-indol-1-yl)methanone, 2-(2,4-difluorophenyl)-1-(3-methyl-6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethan-1-one, (2-fluorophenyl)(3-methyl-6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (2-fluoro-5-methoxyphenyl)(3-methyl-6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, cyclopentyl(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (4-chlorophenyl)(3-methyl-5- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, 1-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-2-(pyridin-3-yl)ethan-1-one, (3-methyl-5- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)(oxetan-3-yl)methanone, 2-(4- methoxyphenyl)-1-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1- one, 2-(4-chlorophenyl)-1-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethan-1-one, 1-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)propan-1- one, 2-(4-fluorophenyl)-1-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethan-1-one, 1-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-2- phenylethan-1-one, 1-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)-2-(p- tolyl)ethan-1-one, 1-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan- 1-one, cyclopropyl(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)methanone, 2-methyl-1-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)propan-1-one, cyclobutyl(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)methanone, 2-methoxy-1-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)propan-1-one, isoxazol-4-yl(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)methanone, (1-methyl-1H-pyrazol-4-yl)(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)methanone, (1-methyl-1H-pyrazol-3-yl)(3-methyl-5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)methanone, 1-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)-2-(pyrimidin-5-yl)ethan-1-one, (4-fluorophenyl)(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methanone, (3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)(p-tolyl)methanone, 2-(2,4- difluorophenyl)-1-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethan-1- one, (2-fluorophenyl)(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)methanone, (2-fluoro-5-methoxyphenyl)(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)-1H-indol-1-yl)methanone, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethyl)cyclopentanesulfonamide, 4-chloro-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzenesulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1-(pyridin-3-yl)methanesulfonamide, N-(2-(3-methyl- 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)oxetane-3-sulfonamide, 1-(4- chlorophenyl)-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)methanesulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethyl)ethanesulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)ethyl)-1-(4-(trifluoromethyl)phenyl)methanesulfonamide, 1-(4-fluorophenyl)-N-(2- (3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)methanesulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1- phenylmethanesulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethyl)-1-(p-tolyl)methanesulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)methanesulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)cyclopropanesulfonamide, N-(2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)propane-2-sulfonamide, N-(2-(3- methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)cyclobutanesulfonamide, 1-methoxy-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)ethane-1-sulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H- indol-1-yl)ethyl)isoxazole-4-sulfonamide, 1-methyl-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1H-pyrazole-4-sulfonamide, 1-methyl-N-(2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1H-pyrazole-3-sulfonamide, N-(2- (3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzenesulfonamide, N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)-1-(pyrimidin-5- yl)methanesulfonamide, 4-fluoro-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)- 1H-indol-1-yl)ethyl)benzenesulfonamide, 1-(2,4-difluorophenyl)-N-(2-(3-methyl-5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)methanesulfonamide, 2-fluoro-N-(2- (3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)ethyl)benzenesulfonamide and 2-fluoro-5-methoxy-N-(2-(3-methyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1- yl)ethyl)benzenesulfonamide. 5) 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. 6) An agrochemical composition comprising the compound of formula (I) according to claim 1 and at least one agrochemically acceptable auxiliary. 7) The composition according to claim 6, wherein said composition may further comprises at least one additional active ingredient. 8) The composition according to claim 6, wherein said composition is applied to seed and the amount of compound of the formula (I) in said composition ranges from 0.1 g a.i. to 10 kg a.i .per 100 kg of seeds. 9) 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 5 or the composition according to claim 6. 10) 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) as claimed in claim 1 or the combination according to claim 5 or the composition according to claim 6, is applied to the plants, to parts thereof or locus thereof. 11) A method according to claim 10, wherein the phytopathogenic microorganisms are selected from the group comprising of 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. 12) Use of a compound of formula (I) according to claim 1 as a fungicide. 13) A process for the synthesis of compound of formula (I) as claim in claim 1, wherein said process comprising at least one of the following steps (a) to (k): a) reacting a compound of formula 2 with a hydroxyl amine to afford a compound of formula 4;
Figure imgf000110_0001
wherein, R2 or R3 is not CN; R4, Q and A1 are as defined in claim 1; b) reacting the compound of formula 4 with a suitable carboxylic acid anhydride of formula 5a or a suitable carboxylic acid chloride of formula 5b to afford a compound of formula (I);
Figure imgf000110_0002
wherein, R1, R2, R3, R4, Q and A1 are as defined in claim 1; c) reacting a compound of formula 6a with a compound of formula 7 to afford a compound of formula (I);
Figure imgf000110_0003
wherein, Q is Q1; R is hydrogen or alkyl; R1, R2, R3, R4 and A1 are as defined in claim 1; d) reacting a compound of formula 10 with a suitable acid to afford a compound of formula 11; wherein, R1, R2, R3, R4, and A1 are as defined in claim 1; e) reacting a compound of formula 11 with a suitable acid chloride to afford a compound of formula (I);
Figure imgf000111_0001
wherein, Q is Q4; R1, R2, R3, R4, and A1 are as defined in claim 1; f) reacting a compound of formula 20 with a suitable deprotecting reagent to afford a compound of formula 21;
Figure imgf000111_0002
wherein, R1, R2, R3, R4, R10 and A1 are as defined in claim 1; g) reacting a compound of formula 21 with a suitable acid chloride of formula 15a or a suitable acid of formula 15b to afford a compound of formula (I);
Figure imgf000111_0003
wherein, Q is Q2; R1, R2, R3, R4, R10, R11 and A1 are as defined in claim 1; h) reacting a compound of formula 21 with a sulfonyl chloride compound of formula 5c to afford a compound of formula (I);
Figure imgf000111_0004
wherein, Q is Q3; R1, R2, R3, R4, R10, R11 and A1 are as defined in claim 1; i) reacting the compound of formula 21 with an amine compound of formula 10a or an isocyanate compound of formula 10b afford a compound of formula (I);
Figure imgf000112_0001
wherein, Q is Q8; R1, R2, R3, R4, R10, R11 and A1 are as defined in claim 1; j) reacting a compound of formula 21 with a compound of formula 10c or 10d to afford a compound of formula (I);
Figure imgf000112_0004
wherein, Q is Q9; R1, R2, R3, R4, R10, R11 and A1 are as defined in claim 1; k) reacting a compound of formula 6c with a sulfoximine compound of formula 7a to afford a compound of formula (I);
Figure imgf000112_0002
wherein, Q is Q10; R1, R2, R3, R4, R10, R11 and A1 are as defined in claim 1. 14) A compound of formula (II);
Figure imgf000112_0003
Formula (II) wherein, Ra is selected from the group consisting of cyano or –CH2(NH2)=N-OH; R2, R3, R4, A1 and Q are as defined in claim 1. 15) A compound of formula (III) or a salt thereof; Formula (III) wherein, Rb is selected from the group consisting of hydrogen or –C1-C4-alkyl-NH-R10; R1, R2, R3, R4, and A1 are as defined in claim 1.
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