RU2818085C2 - Novel oxadiazole-based compounds for controlling phytopathogenic fungi or preventing damage by them - Google Patents

Abstract

FIELD: chemistry.

SUBSTANCE: invention relates to a compound of formula (I) and an agriculturally acceptable salt thereof, where R¹ is C₁-C₂ haloalkyl; L¹ is a direct bond; L² is a direct bond; A is phenyl or pyridyl; and said phenyl or pyridyl is optionally substituted with one or more identical or different groups R^A; R^A is selected from the group consisting of hydrogen, halogen, cyano, amino, hydroxy, C₁-C₆alkyl, C₃-C₈cycloalkyl, C₁-C₆haloalkyl, C₁-C₆hydroxyalkyl, C₃-C₈halocycloalkyl, C₁-C₆alkoxy and C₁-C₆haloalkoxy; R^4b is independently selected from the group consisting of hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy and C₁-C₆haloalkoxy; R^2d, R^3d, R^2f and R^3f are independently selected from the group consisting of hydrogen, halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy and C₁-C₄haloalkoxy; W¹ is O; Q is O, S(=O)_0-2, S(=O)_0-1(=NR^4b), NR^4b, -N=S(=NR^8a)(R^8b)-; -N=S(=O)_0-1(R^8c)-; values of radical R¹⁰ are defined in cl. 1 of the claims. Invention also relates to methods of producing a compound of formula (I) and a composition based on the compound of formula (I).

EFFECT: novel compounds of formula (I) are obtained, which can be used in agriculture as agents for controlling or preventing infection of plants with phytopathogenic microorganisms.

16 cl, 8 tbl, 11 ex

Description

FIELD OF TECHNOLOGY TO WHICH THE INVENTION RELATES

The present invention relates to new oxadiazole-based compounds useful for controlling phytopathogenic fungi, to a combination thereof and to a composition containing the new oxadiazole-based compounds. The present invention also relates to a method for controlling or preventing phytopathogenic fungi.

PREREQUISITES FOR THE CREATION OF THE INVENTION

Oxadiazoles have been previously disclosed in the literature. For example, in JPS 5665881, JPS 63162680, JPS 6296480, JPS 6051188, WO 2005051932, EP 3165093, EP 3167716, EP 3165093, WO 2017076740, WO 2017102006, WO 2017110861, WO 2017110862, WO 2017110864, WO 2017157962, WO 2017174158, WO 2017198852 , WO 2017207757, WO 2017211650, WO 2017211652, WO 2017220485, WO 2017072247, WO 2017076742, WO 2017076757, WO 2017076935, WO 201801 5447, WO 2018065414, WO 2018118781, WO 2018187553 and WO 2018202491 various oxadiazoles were disclosed.

The oxadiazole-based compounds described in the above literature are characterized by disadvantages in certain aspects, such as that they exhibit a narrow range of application and that they do not have satisfactory fungicidal activity, in particular at low application doses.

Therefore, it is an object of the present invention to provide compounds having improved/enhanced activity and/or a broader spectrum of activity against plant pathogenic fungi.

This object is achieved by using the compound of formula (I) of the present invention to control or prevent phytopathogenic fungi.

BRIEF DESCRIPTION OF THE INVENTION

The present invention relates to a compound of formula (I),

Formula (I),

where R¹, L¹, A, L²,W¹, R^2f, R^3f, Q and R¹⁰ are defined in the detailed description. The present invention also relates to a process for preparing the compound of formula (I).

The compounds of formula (I) have been found to have advantages over compounds reported in the literature in the form of improved fungicidal activity, a wider spectrum of biological activity, lower application doses, more favorable biological or environmental properties or enhanced plant compatibility.

The present invention further relates to a combination containing a compound of formula (I) according to the present invention and at least one additional pesticide active substance to provide effective control or prevention of phytopathogenic fungi that are difficult to control.

The present invention further relates to a composition containing a compound of formula (I) or a compound of formula (I) in combination with an additional pesticidal active substance.

The present invention further relates to a method and use of a compound of formula (I), a combination or composition thereof, for the control or prevention of plant diseases, especially phytopathogenic fungi.

DETAILED DESCRIPTION OF THE INVENTION

DEFINITIONS

The definitions presented herein, within the terminology used in the present invention, are used for purposes of illustration only and do not in any way limit the scope of the present invention as set forth in the present invention.

It is intended that the terms “provides”, “providing for”, “includes”, “comprising”, “has”, “having”, “contains”, “comprising”, “characterized” as used herein, or any other variation thereof , cover non-exclusive inclusion, subject to any expressly stated limitation. For example, a composition, mixture, process or method that provides a list of elements is not necessarily limited to those elements, but may include other elements not explicitly listed or not inherent in such composition, mixture, process or method.

The transitive expression "consisting of" excludes any element, step or ingredient not specified. If such an expression appears in a claim, it excludes the inclusion of materials other than those specified, except for impurities normally associated with them. If the expression "comprising" appears in a subordinate clause of a claim, rather than immediately following a restrictive clause, then it limits only the element specified in such subordinate clause; other elements are not excluded from the entire claim.

The transitive expression "consisting essentially of" is used to define a composition or process that includes materials, steps, features, components or elements in addition to those literally stated, provided that these additional materials, steps, features, components or elements do not significantly affect on the main (main) and new (new) feature(s) of the present invention. The term "consisting essentially of" is intermediate between "including" and "consisting of".

Additionally, unless expressly stated to the contrary, “or” means an inclusive “or” and not an exclusive “or.” For example, the condition A "or" B is satisfied if any 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).

It is also intended that the singular forms preceding an element or component of the present invention are non-limiting as to the number of units (i.e., instances) of the element or component. Therefore, singular forms are to be read as including one or at least one, and the singular form of an element or component word also includes the plural unless the singular is clearly intended.

As used herein, the term "invertebrate pest" includes arthropods, gastropods and nematodes of economic importance as pests. The term "arthropod" includes insects, microscopic mites, spiders, scorpions, labiopods, bipeds, woodlice and symphylos. The term "gastropod" includes snails, slugs and other Stylommatophora. The term "nematode" means a living organism belonging to the phylum Nematoda. The term "helminths" includes roundworms, heartworms, herbivorous nematodes (Nematoda), flukes (Trematoda), acanthocephalans and tapeworms (Cestoda).

In the context of the present invention, “control of invertebrate pests” means suppression of the development of an invertebrate pest (including mortality, reduction of nutrition and/or impairment of reproduction), and related expressions are defined similarly.

The term "agronomic" refers to the production of field crops, such as food crops, feed crops and fiber, and includes the production of corn, soybeans and other legumes, rice, cereals (e.g. wheat, oats, barley, rye, rice, maize) , leafy vegetables (for example, lettuce, cabbage and other brassicas), fruiting vegetables (for example, tomatoes, peppers, eggplant, cruciferous and squash), potatoes, sweet potatoes, grapes, cotton, fruit trees (for example, pome, stone fruit and citrus) , bush plants (berries, cherries) and other specialty crops (for example, canola, sunflowers, olives).

The term "non-agronomic" refers to crops other than field crops, such as horticultural crops (such as greenhouse plants, seedlings or ornamental plants not grown in the field), residential, agricultural, commercial and industrial applications, turf ( e.g. turf farm, pasture, golf course, lawn, sports field, etc.), in wood products, in stored products, in agroforestry and vegetation management, in public health (i.e. human health) and in animal health (eg, domesticated animals such as pets, livestock and poultry, non-domesticated animals such as wild animals).

Non-agronomic uses include protecting an animal from an invertebrate parasitic pest by administering a parasite-killing (ie, biologically effective) amount of a compound of the present invention, typically in the form of a composition formulated for veterinary use, to the animal being protected. As defined in the disclosure and claims of the present invention, the terms "parasitic" and "parasitic" refer to observable effects on an invertebrate parasitic pest for the purpose of providing protection to the animal against the pest. Parasite killing effects generally relate to a reduction in the prevalence or activity of the target invertebrate parasitic pest. Such effects on the pest include necrosis, death, stunted growth, reduced mobility or reduced ability to reside on or in the host animal, decreased feeding, and suppressed reproduction. These effects on invertebrate parasitic pests involve the control (including prevention, reduction or elimination) of parasite infestation or infection of the animal.

The compounds of the present invention may be present either in pure form or in the form of mixtures of different possible isomeric forms, such as stereoisomers or constitutional isomers. The various stereoisomers include enantiomers, diastereomers, chiral isomers, atropoisomers, conformers, rotamers, tautomers, optical isomers, polymorphs and geometric isomers. Any necessary mixtures of these isomers are within the scope of the claims of the present invention. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit a beneficial effect when enriched relative to the other isomer(s) or when separated from the other isomer(s). Additionally, processes or methods or technology for separating, enriching and/or selectively producing these isomers are known to one skilled in the art.

The meaning of various terms used in this description will be illustrated.

The term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" or -N(alkyl), or alkylcarbonylalkyl or alkylsulfonylamino, includes straight or branched C ₁ -C ₂₄ alkyl, preferably C ₁ -C ₁₅ alkyl, more preferably C ₁ -C ₁₀ alkyl, most preferably C ₁ -C ₆ alkyl. Non-limiting examples of alkyl include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1- methylpropyl and 1-ethyl-2-methylpropyl or different isomers. If the alkyl is at the end of the compound substituent, as in the case of alkylcycloalkyl, then the portion of the compound substituent at the beginning, for example, cycloalkyl, may be mono- or polysubstituted, equally or differently, and independently with alkyl. The same also applies to complex substituents in which other radicals, such as alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy, etc., are found at the end.

The term "alkenyl", used either alone or in compound words, includes straight or branched chain C ₂ -C ₂₄ alkenes, preferably C ₂ -C ₁₅ alkenes, more preferably C ₂ -C ₁₀ alkenes, most preferably C ₂ -C ₆ alkenes. Non-limiting examples of alkenes include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl- 2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1- butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1- methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl- 3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl- 2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl- 1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl- 2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1- methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl and various isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl as part of a complex substituent, such as haloalkenyl, etc., unless specifically stated otherwise.

Non-limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3- pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2- butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl and other isomers. This definition also applies to alkynyl as part of a complex substituent, such as haloalkynyl, etc., unless otherwise specifically stated elsewhere. The term "alkynyl" may also include species consisting of multiple triple bonds, such as 2,5-hexadinyl.

The term "cycloalkyl" means alkyl that is closed to form a ring. Non-limiting examples include cyclopropyl, cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as part of a complex substituent, e.g., cycloalkylalkyl, etc., unless otherwise specifically stated 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 part of a complex substituent, e.g. cycloalkenylalkyl, etc., unless specifically stated otherwise.

The term "cycloalkynyl" means alkynyl, closed to form a ring, including monocyclic, partially unsaturated groups. Non-limiting examples include cyclopropynyl, cyclopentinyl and cyclohexynyl. This definition also applies to cycloalkynyl as part of a complex substituent, e.g. cycloalkynylalkyl, etc., unless otherwise specifically stated elsewhere.

The terms "cycloalkoxy", "cycloalkenyloxy", etc. are defined similarly. Non-limiting examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as part of a complex substituent, e.g., cycloalkoxyalkyl, etc., unless otherwise specifically stated elsewhere.

The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. Additionally, when used in compound words such as "haloalkyl", said alkyl may be partially or completely replaced by halogen atoms, which may be the same or different. Non-limiting examples of "haloalkyl" include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2, 2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro- 2,2,2-trifluoroethyl and 1,1,1-trifluoroprop-2-yl. This definition also applies to haloalkyl as part of a complex substituent, e.g. haloalkylaminoalkyl, etc., unless specifically stated otherwise.

The terms “haloalkyl” and “haloalkynyl” are defined similarly, except that instead of alkyl groups, the substituent contains alkenyl and alkynyl groups.

The term "haloalkoxy" means straight or branched chain alkoxy groups, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as defined 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 1,1,1-trifluoroprop- 2-hydroxy. This definition also applies to haloalkoxy as part of a complex substituent, e.g. haloalkoxyalkyl, etc., unless otherwise specifically stated elsewhere.

The term "haloalkylthio" means straight or branched chain alkylthio groups wherein some or all of the hydrogen atoms in these groups are replaced by halogen atoms as defined above. Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, o, 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 1,1,1-trifluoroprop- 2-iltio. This definition also applies to haloalkylthio as part of a complex substituent, e.g. haloalkylthioalkyl, etc., unless otherwise specifically stated elsewhere.

Non-limiting examples of "haloalkylsulfinyl" include CF ₃ S(O), CCl ₃ S(O), CF ₃ CH ₂ S(O) and CF ₃ CF ₂ S(O). Non-limiting examples of "haloalkylsulfonyl" include CF ₃ S(O) ₂ , CCl ₃ S(O) ₂ , CF ₃ CH ₂ S(O) ₂ and CF ₃ CF ₂ S(O) ₂ .

The term "hydroxy" means -OH, amino means -NRR, where R may represent H or any other possible substituent such as alkyl. Carbonyl means -C(=O)-, carbonyloxy means -OC(=O)-, sulfinyl means SO, sulfonyl means S(O) ₂ .

The term "alkoxy", used either alone or in compound words, includes C ₁ -C ₂₄ alkoxy, preferably C ₁ -C ₁₅ alkoxy, more preferably C ₁ -C ₁₀ alkoxy, most preferably C ₁ -C ₆ . 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 1-ethyl-2-methylpropoxy and various isomers. This definition also applies to alkoxy as part of a complex substituent, e.g., haloalkoxy, alkynylalkoxy, etc., unless specifically stated otherwise.

The term "alkoxyalkyl" means the substitution of alkoxy for alkyl. Non-limiting examples of "alkoxyalkyl" include CH ₃ OCH ₂ , CH ₃ OCH ₂ CH ₂ , CH ₃ CH ₂ OCH ₂ , CH ₃ CH ₂ CH ₂ CH ₂ OCH ₂ and CH ₃ CH ₂ OCH ₂ CH ₂ .

The term "alkoxyalkoxy" means the substitution of alkoxy for alkoxy.

The term "alkylthio" includes straight or branched chain alkylthio species 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 1-ethyl-2-methylpropylthio and various isomers.

Halocycloalkyl, halocycloalkenyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylcarbonyl, cycloalkylcarbonyl, haloalkoxyalkyl, etc. are defined similarly to the above examples.

The term "alkylthioalkyl" means substitution of alkylthio on alkyl. Non-limiting examples of "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" means the substitution of alkylthio with alkoxy. The term "cycloalkylalkylamine" means substitution with cycloalkyl on alkylamino.

The terms "alkoxyalkoxyalkyl", "alkylaminoalkyl", "dialkylaminoalkyl", "cycloalkylaminoalkyl", "cycloalkylaminocarbonyl" and the like are defined in the same way as "alkylthioalkyl" or "cycloalkylaminoalkyl".

The term "alkoxycarbonyl" means an alkoxy group linked to the skeleton via a carbonyl group (-CO-). This definition also applies to alkoxycarbonyl as part of a complex substituent, for example, cycloalkoxycarbonyl, etc., unless otherwise specifically stated elsewhere.

The term "alkoxycarbonylalkylamino" means substitution with alkoxycarbonyl on alkylamino. "Alkylcarbonylalkylamino" means substitution with alkylcarbonyl on alkylamino. The terms alkylthioalkoxycarbonyl, cycloalkylalkylaminoalkyl, and the like are defined similarly.

Non-limiting examples of "alkylsulfinyl" include methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2 - dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1, 3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl- 1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl and various isomers. The term "arylsulfinyl" includes Ar-S(O), where Ar can be any carbocycle or heterocycle. This definition also applies to alkylsulfinyl as part of a complex substituent, e.g., haloalkylsulfinyl, etc., unless otherwise specifically stated elsewhere.

Non-limiting examples of "alkylsulfonyl" include methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2 - dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1, 3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl- 1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl and various isomers. The term "arylsulfonyl" includes Ar-S(O) ₂ where Ar can be any carbocycle or heterocycle. This definition also applies to alkylsulfonyl as part of a complex substituent, e.g. alkylsulfonylalkyl, etc., unless otherwise stated elsewhere.

"Alkylamino", "dialkylamino" and the like are defined in a manner similar to the above examples.

The term "carbocycle or carbocyclic" includes "aromatic carbocyclic ring system" and "non-aromatic carbocyclic ring system" or polycyclic or bicyclic (spiro-, fused, bridged, non-fused) ring compounds in which the rings may be aromatic or non-aromatic (where aromatic indicates , that Hückel's rule is observed, and non-aromatic indicates that Hückel's rule is not observed).

The term "heterocycle or heterocyclic" includes "aromatic heterocycle or heteroaryl ring system" and "non-aromatic heterocyclic ring system" or polycyclic or bicyclic (spiro-, fused, bridged, non-fused) ring compounds, in which the rings may be aromatic or non-aromatic, wherein the heterocyclic ring contains at least one heteroatom selected from N, O, S(O) _0-2 , and/or the ring member representing C, the heterocycle may be replaced by C(=O), C(=S), C (=CR*R*) and C=NR*, * indicates integers.

The term “non-aromatic heterocycle” or “non-aromatic heterocyclic” means a three to fifteen membered, preferably three to twelve membered, saturated or partially unsaturated heterocycle containing from one to four heteroatoms from the group of oxygen, nitrogen and sulfur: mono-, bi- or tricyclic heterocycles, which contain, in addition to the members of the hydrocarbon ring, one to three nitrogen atoms and/or one oxygen atom or sulfur atom or one or two oxygen atoms and/or sulfur atoms; if the ring contains more than one oxygen atom, they are not directly adjacent; non-limiting examples are oxetanyl, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazole idinil, 3 -isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl , 1-imidazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1 ,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-1-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3 ,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-1-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3 -yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2 -yl, 2,4-dihydrothien-3-yl, pyrrolinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazoline -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-1-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-1-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, pyrazinyl, morpholinyl, thiomorpholinyl , 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3 ,5-hexahydrotriazin-2-yl, 1,2,4-hexahydrotriazin-3-yl, cycloserines, 2,3,4,5-tetrahydro[1H]azepine-1-, or -2-, or -3-, or -4-, or -5-, or -6-, or -7-yl, 3,4,5,6-tetra-hydro[2H]azepine-2-, or -3-, or -4-, or -5-, or -6-, or -7-yl, 2,3,4,7-tetrahydro[1H]azepine-1-, or -2-, or -3-, or -4-, or - 5-, or -6-, or -7-yl, 2,3,6,7-tetrahydro[1H]azepine-1-, or -2-, or -3-, or -4-, or -5- , or -6-, or -7-yl, hexahydroazepine-1-, or -2-, or -3-, or -4-yl, tetra- and hexahydrooxepinyl, such as 2,3,4,5-tetrahydro[ 1H]oxepin-2-, or -3-, or -4-, or -5-, or -6-, or -7-yl, 2,3,4,7-tetrahydro[1H]oxepin-2-, or -3-, or -4-, or -5-, or -6-, or -7-yl, 2,3,6,7-tetrahydro[1H]oxepin-2-, or -3-, or - 4-, or -5-, or -6-, or -7-yl, hexahydroazepine-1-, or -2-, or -3-, or -4-yl, tetra- and hexahydro-1,3-diazepinyl , tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl, tetra- and hexahydro-1,3-dioxepinyl, tetra- and hexahydro- 1,4-dioxepinyl. This definition also applies to heterocyclyl as part of a complex substituent, e.g. heterocyclylalkyl, etc., unless otherwise specifically stated elsewhere.

The term "heteroaryl" or "aromatic heterocyclic" means a system of 5- or 6-membered, fully unsaturated monocyclic rings containing from one to four heteroatoms from the group of oxygen, nitrogen and sulfur; if the ring contains more than one oxygen atom, they are not directly adjacent; 5-membered heteroaryl containing from one to four nitrogen atoms or from one to three nitrogen atoms and one sulfur atom or oxygen atom; 5-membered heteroaryl groups which, in addition to carbon atoms, may contain from one to four nitrogen atoms or from one to three nitrogen atoms and one sulfur or oxygen atom as ring members, non-limiting examples are 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-linked 5-membered heteroaryl containing from one to four nitrogen atoms or benzene-fused nitrogen-linked 5-membered heteroaryl containing from one to three nitrogen atoms: 5-membered heteroaryl groups which, in addition to carbon atoms, can contain from one to four nitrogen atoms or from one to three nitrogen atoms as hydrocarbon ring members, and in which two adjacent hydrocarbon ring members or one nitrogen atom and one adjacent hydrocarbon ring member may be bridged via buta-1,3- diene-1,4-diyl group in which one or two carbon atoms can be replaced by nitrogen atoms, where these rings are attached to the skeleton via one of the nitrogen atoms in the ring, non-limiting examples are 1-pyrrolyl, 1-pyrazolyl, 1,2 ,4-triazol-1-yl, 1-imidazolyl, 1,2,3-triazol-1-yl and 1,3,4-triazol-1-yl.

6-membered heteroaryl which contains from one to four nitrogen atoms: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain, respectively, from one to three and from one to four nitrogen atoms as ring members, by way of non-limiting examples are 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1 ,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl; benzene-fused 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulfur atom: non-limiting examples are indol-1-yl, indol-2-yl, indol-3-yl, indol-4 -yl, indol-5-yl, indol-6-yl, indol-7-yl, benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, indazol-1-yl , indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl, indazol-7-yl, indazol-2-yl, 1-benzofuran-2-yl, 1-benzofuran-3 -yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl , 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1-benzothiophen-6-yl, 1-benzothiophen-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol-4 -yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4 -yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl and 1,3-benzoxazol-7-yl; a 6-membered heteroaryl condensed with benzene, which contains from one to three nitrogen atoms: non-limiting examples are quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl and isoquinolin- 8-il.

The term "trialkylsilyl" includes 3 branched alkyl radicals and/or straight chain alkyl radicals attached to and linked through a silicon atom, such as trimethylsilyl, triethylsilyl and tert-butyldimethylsilyl. "Halotrialkylsilyl" means that at least one of the three alkyl radicals is partially or completely replaced by halogen atoms, which may be the same or different. The term "alkoxytrialkylsilyl" means that at least one of the three alkyl radicals is replaced by one or two alkoxy radicals, which may be the same or different. The term "trialkylsilyloxy" refers to a trialkylsilyl moiety attached via an oxygen atom.

Non-limiting examples of "alkylcarbonyl" include C(=O)CH ₃ , C(=O)CH ₂ CH ₂ CH ₃ and C(=O)CH(CH ₃ ) ₂ . Non-limiting examples of "alkoxycarbonyl" include CH ₃ OC(=O), CH ₃ CH ₂ OC(=O), CH ₃ CH ₂ CH ₂ OC(=O), (CH ₃ ) ₂ CHOC(=O) and various butoxy- or pentoxycarbonyl isomers. Non-limiting examples of "alkylaminocarbonyl" include CH ₃ NHC(=O), CH ₃ CH ₂ NHC(=O), CH ₃ CH ₂ CH ₂ NHC(=O), (CH ₃ ) ₂ CHNHC(=O) and various butylamino- or pentylaminocarbonyl isomers. Non-limiting examples of "dialkylaminocarbonyl" include (CH ₃ ) ₂ NC(=O), (CH ₃ CH ₂ ) ₂ NC(=O), CH ₃ CH ₂ (CH ₃ )NC(=O), CH ₃ CH ₂ CH ₂ (CH ₃ )NC(=O) and (CH ₃ ) ₂ CHN(CH ₃ )C(=O). Non-limiting examples of "alkoxyalkylcarbonyl" include CH ₃ OCH ₂ C(=O), CH ₃ OCH ₂ CH ₂ C(=O), CH ₃ CH ₂ OCH ₂ C(=O), CH ₃ CH ₂ CH ₂ CH ₂ OCH ₂ C(=O) and CH ₃ CH ₂ OCH ₂ CH ₂ C(=O). Non-limiting examples of "alkylthioalkylcarbonyl" include CH ₃ SCH ₂ C(=O), CH ₃ SCH ₂ CH ₂ C(=O), CH ₃ CH ₂ SCH ₂ C(=O), CH ₃ CH ₂ CH ₂ CH ₂ SCH ₂ C(=O) and CH ₃ CH ₂ SCH ₂ CH ₂ C(=O). The term haloalkylsulfonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkylamino and the like are defined similarly.

Non-limiting examples of "alkylaminoalkylcarbonyl" include CH ₃ NHCH ₂ C(=O), CH ₃ NHCH ₂ CH ₂ C(=O), CH ₃ CH ₂ NHCH ₂ C(=O), CH ₃ CH ₂ CH ₂ CH ₂ NHCH ₂ C(=O) and CH ₃ CH ₂ NHCH ₂ CH ₂ C(=O).

The term "amide" means A-R'C=ONR''-B, where R' and R'' indicate substituents, and A and B indicate any group.

The term "thioamide" means A-R'C=SNR''-B, where R' and R'' are substituents, and A and B are any group.

The total number of carbon atoms in a substituent group is indicated by the prefix "C _i -C _j ", where i and j are numbers from 1 to 21. For example, C ₁ -C ₃ alkylsulfonyl means methylsulfonyl through propylsulfonyl; C ₂ alkoxyalkyl means CH ₃ OCH ₂ ; C ₃ alkoxyalkyl means, for example, CH ₃ CH(OCH ₃ ), CH ₃ OCH ₂ CH ₂ or CH ₃ CH ₂ OCH ₂ ; and C ₄ alkoxyalkyl refers to various isomers of an alkyl group substituted with an alkoxy group containing only four carbon atoms, examples include CH ₃ CH ₂ CH ₂ OCH ₂ and CH ₃ CH ₂ OCH ₂ CH ₂ . In the above enumeration, if a compound of formula I contains one or more heterocyclic rings, then all substituents are attached to such rings through any available carbon or nitrogen atom by substituting a hydrogen at said carbon or nitrogen atom.

If a compound is substituted with a substituent bearing a subscript which indicates that the number of these substituents may be greater than 1, then said substituents (if greater than 1) are independently selected from a group of defined substituents. Additionally, if 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 integers from 0 to 4, inclusive.

If a group contains a substituent that may be hydrogen, then the group is considered to be unsubstituted if the substituent is taken to be hydrogen.

The embodiments provided herein and their various features and advantageous details are explained with reference to non-limiting embodiments in the description. Descriptions of commonly known components and processing methods are omitted so as not to unduly obscure the understanding of the embodiments provided herein. The examples used herein are intended only to provide a simplified understanding of the manner in which the embodiments herein may be practiced and to further enable those skilled in the art to practice the embodiments set forth herein. document. Accordingly, the examples should not be construed as limiting the scope of the embodiments provided herein.

The description of specific embodiments will fully demonstrate the general nature of the embodiments specified herein, which others can, by applying modern knowledge, easily modify and/or adapt for different applications such specific embodiments without deviating from the generic concept and, therefore, such adaptations and modifications are to be understood and intended to be understood within the meaning and range of equivalents of the disclosed embodiments. It should be understood that language or terminology used herein is intended to be descriptive and not limiting. Therefore, although the embodiments set forth herein have been described in the context of preferred embodiments, those skilled in the art will understand that the embodiments set forth herein may be practiced with modifications within the spirit and scope of the embodiments. as described in this document.

Any reference to documents, acts, materials, devices, articles, etc. included in this description is made solely for the purpose of providing context for the present invention. It is not intended that all or any of these materials form part of the prior art or were generally known in the art to which the present invention relates because they were known elsewhere before the priority date of this application.

The numerical values specified in the description and in the description/claims may form a critical part of the present invention, any deviation from such numerical values shall still be within the scope of the present invention, as long as such deviation follows the same scientific principle as that of the present invention specified in the present invention.

The compounds that are the subject of the present invention may, if appropriate, be present in the form of mixtures of different possible isomeric forms, especially stereoisomers, for example E- and Z-, threo- and erythro-, and also optical isomers, but if appropriate also tautomers. Both E- and Z-isomers, and also threo- and erythro-isomers, and optical isomers, any desired mixtures of such isomers and possible tautomeric forms are disclosed and claimed. The term "pest" for the purposes of the present invention includes, without limitation, fungi, stramenopiles (oomycetes), bacteria, nematodes, microscopic mites, mites, insects and rodents.

The term “plant” as used herein refers to plants and plant populations, such as desired and undesired wild or crop plants (including naturally occurring crop plants). Agricultural crops may be plants that can be obtained using traditional methods of breeding and optimization or methods of biotechnology and genetic engineering or combinations of these methods, including transgenic plants and including cultivars of plants that are and are not protected by plant breeders' rights.

For the purposes of the present invention, the term "plant" includes a living organism of a type, examples of which are trees, bushes, medicinal plants, herbs, ferns and mosses, typically growing in one place, absorbing water and essential substances through its roots and synthesizing nutrients in its leaves by photosynthesis.

Examples of “plant” for purposes of the present invention include, but are not limited to, crops such as wheat, rye, barley, triticale, oats or rice; beets, such as sugar beets or fodder beets; fruits and fruit trees such as apples, stone fruits or berries, such as apples, pears, plums, peaches, almonds, berries, strawberries, raspberries, blueberries or gooseberries, pulses such as beans, peas, alfalfa or soybeans; oil plants such as rapeseed, mustard, olives, sunflowers, coconut, cocoa beans, castor plants, oil palms, groundnuts or soybeans; cucurbits, such as pumpkins, cucumbers or melons; fibrous plants such as cotton, flax, hemp or jute, citrus fruits and citrus plants such as oranges, lemons, grapefruits or tangerines; any garden plants, vegetables such as spinach, lettuce, asparagus, types of cabbage, carrots, onions, tomatoes, potatoes, pumpkin or paprika; bay plants such as avocado, cinnamon or camphor; pumpkin; oil plants; plants used for energy and raw materials, such as cereals, corn, soybeans, other pulses, canola, sugar cane or oil palm; tobacco; nuts; coffee; tea; cocoa; bananas; peppers; grapes (table grapes and grapes for grape juice production); hop; turf; "sweet leaf" (also called stevia); natural rubber plants or ornamental and forest plants such as flowers, bushes, deciduous or evergreen trees such as conifers; and plant propagation materials, such as seeds, and the harvest of these plants.

Preferably, the plant for purposes of the present invention includes, without limitation, cereals, corn, rice, soybeans and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any garden plants, cucurbits, oil plants, tobacco, coffee, tea, cocoa, sugar beets, sugar cane, cotton, potatoes, tomatoes, onions, peppers and vegetables, ornamental plants, any floricultural plants and other plants for human and animal use.

The term "plant parts" should be understood to mean all parts and organs of plants above and below the soil level. For purposes of the present invention, the term "plant parts" includes, without limitation, cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots, including tap roots, lateral roots, root hairs, root tip, root cap, rhizomes, stems, shoots, fruits, fruiting bodies, bark, stem, buds, auxiliary buds, meristems, nodes and internodes.

The term "growing site" includes the soil, the surrounding area of the plant or plant parts, and equipment or tools used before, during or after sowing/planting the plant or plant part.

The use of the compounds of the present invention, or a compound of the present invention in a composition, optionally containing other compatible compounds, to a plant or plant material or its location involves application by a method known to one skilled in the art, which includes, but is not limited to, spraying, coating , immersion, fumigation, impregnation, injection and spraying.

The term "applied" means applied to a plant or parts of a plant, either physically or chemically, including impregnation.

Based on the above, the present invention provides a compound of formula (I),

Formula (I),

Where

R ¹ represents C ₁ -C ₂ haloalkyl;

L ¹ represents a direct connection, -CR ² R ³ -, -C(=W ¹ )-, -O-, -S(=O) _0-2 - and -NR ^4a -; where the "-" sign at the beginning and end of the group indicates the point of attachment either to the oxadiazole ring or to A;

L ² represents a direct connection or -(CR ^2a R ^3a ) _1-3 -;

A is an aromatic carbocyclic ring or an aromatic heterocyclic ring; where the heteroatoms of the aromatic heterocyclic ring are selected from N, O and S; and ring A is optionally substituted with one or more identical or different R ^A groups;

R ^A is selected from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy, SF ₅ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₈ cycloalkyl , C ₃ -C ₈ cycloalkylalkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy-C ₁ -C ₄ alkyl, C 1 -C ₆ hydroxyalkyl, C ₂ -C ₆ haloalkenyl, C _{2 -C 6} haloalkynyl, C ₃ -C ₈ halocycloalkyl, C ₁ -C ₆ alkoxy, _{C 1} -C ₆ haloalkoxy, C ₁ -C ₆ haloalkoxycarbonyl, C 1 -C 6 alkylthio, C ₁ -C ₆ haloalkylthio, C _{1 -C 6} haloalkylsulfinyl, C ₁ -C ₆ haloalkylsulfonyl, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C 1 -C ₆ alkylamino, C ₁ -C ₆ dialkylamino, C _{3 -C 8} cycloalkylamino, C ₁ -C ₆ alkyl-C ₃ -C ₈ cycloalkylamino, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkylaminocarbonyl, C ₁ -C ₆ dialkylaminocarbonyl, C ₁ -C ₆ alkoxycarbonyloxy, C ₁ -C ₆ alkylaminocarbonyloxy, C ₁ - C ₆ dialkylaminocarbonyloxy, 5-11 membered spirocyclic ring and 3-6 membered carbocyclic or heterocyclic ring;

wherein the 5-11 membered spirocyclic ring and the 3-6 membered carbocyclic or heterocyclic ring may be optionally substituted with one or more identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, C ₁ -C ₆ alkyl , C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkylalkyl, C _{1 -C 6 haloalkyl, C 1 -C 6 alkoxyalkyl ,} C ₁ -C ₆ hydroxyalkyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkynyl, C ₃ -C ₆ halocycloalkyl, C 1 -C 6 alkoxy, C ₁ -C _{6 alkylthio} , C ₁ -C ₆ haloalkylthio, C _{1 -C 6} haloalkylsulfinyl, C ₁ -C ₆ haloalkylsulfonyl, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ alkylamino, di-C ₁ -C ₆ alkylamino, C ₃ -C ₆ cycloalkylamino, C ₁ -C ₆ alkyl- C ₃ -C ₆ cycloalkylamino, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkylaminocarbonyl, di-C ₁ -C ₆ alkylaminocarbonyl, C ₁ -C ₆ alkoxycarbonyloxy, C ₁ -C ₆ alkylaminocarbonyloxy and di-C ₁ -C ₆ alkylaminocarbonyloxy; or

two R ^A together with the atoms to which they are attached can form a 3-10 membered aromatic or non-aromatic carbocyclic ring or ring system, or an aromatic or non-aromatic heterocyclic ring or ring system; wherein said ring or ring system may be optionally substituted with one or more identical or different ^Ra groups selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₃ -C ₈ cycloalkyl, C ₁ -C ₆ alkoxy-C ₁ -C ₄ alkyl, C ₃ -C ₈ halocycloalkyl, C ₁ -C ₆ alkylamino, di-C ₁ -C ₆ alkylamino and C ₃ -C ₈ cycloalkylamino;

wherein one or more C atoms of the non-aromatic carbocyclic ring may optionally be replaced by C(=O), C(=S), C(=CR ^2b R ^3b ) and C=NR ^6a ;

where the heteroatom of the aromatic heterocyclic ring is selected from N, O and S; where the heteroatom of the non-aromatic heterocyclic ring is selected from N, O, S(=O)_0-2 and S(=O)_0-1(=NR^6a), and one or more C atoms of the non-aromatic heterocyclic ring may optionally be replaced by C(=O), C(=S), C(=CR^2bR^3b) and C=NR^6a;

R ^4a , R ^4b , R ^6a and R ^6b are independently selected from the group consisting of hydrogen, cyano, hydroxy, NR ^b R ^c , (C=O)-R ^d , S(O) _0-2 R ^e , C ₁ -C ₆ alkyl, C _1- C ₆ haloalkyl, C _1- C ₆ alkoxy, C _1- C ₆ haloalkoxy, C _1- C ₆ alkylamino, di-C _1- C ₆ alkylamino, tri-C _1- C ₆ alkylamino and C _3- C ₈ cycloalkyl;

R ^b and R ^c are independently selected from the group consisting of hydrogen, hydroxyl, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₈ cycloalkyl and C ₃ -C ₈ halocycloalkyl;

R ^d is selected from the group consisting of hydrogen, hydroxy, halogen, NR ^b R ^c , C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₃ - C ₈ cycloalkyl and C ₃ -C ₈ halocycloalkyl;

R^e selected from the group consisting of hydrogen, halogen, cyano, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₈cycloalkyl and C₃-C₈halocycloalkyl;

^R2 , ^R3 , ^R2a , ^R3a , ^R2b , ^R3b , ^R2c , ^R3c , ^R2d , ^R3d , ^R2e , ^R3e , ^R2f and ^R3f are independently selected from the group consisting of hydrogen, halogen, cyano, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C 1 -C ₄ haloalkyl, C ₂ -C ₄ haloalkenyl, C _{2 -C 4} haloalkenyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; or

R ² and R ³ ; R ^2a and R ^3a ; R ^2b and R ^3b ; R ^2c and R ^3c ; ^R2d and ^R3d ; and/or R ^2f and R ^3f together with the atoms to which they are attached may form a 3-5 membered non-aromatic carbocyclic ring or heterocyclic ring, which may be optionally substituted with halogen, C ₁ -C ₂ alkyl, C ₁ -C ₂ haloalkyl or C ₁ -C ₂ alkoxy;

W ¹ represents O or S;

Q represents direct connection, O, S(=O) _0-2 , S(=O) _0-1 (=NR ^4b ), NR ^4b , CR ^2e R ^3e , -N=S(=NR ^8a )(R ^8b )-; -N=S(=O) _0-1 (R ^8c )-;

R¹⁰ selected from a group consisting from the group consisting of hydrogen, halogen, hydroxy, cyano, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₁-C₆alkyl-C₃-C₈cycloalkyl, C₃-C₈cycloalkyl-C₁-C₆alkyl, C₃-C₈cycloalkyl-C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl-C₁-C₆alkyl, C₁-C₆alkyl-C₃-C₈cycloalkyl-C₁-C₆alkyl, C₃-C₈cycloalkenyl, C₃-C₈halocycloalkenyl, C₁-C₆alkoxy, C₁-C₆alkoxy-C₁-C₆alkyl, C₃-C₈cycloalkoxy-C₁-C₆alkyl, C₁-C₆alkoxy-C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₆alkyl-C₁-C₆thioalkyl, C₁-C₆alkylsulfinyl-C₁-C₆alkyl, C₁-C₆alkylsulfonyl-C₁-C₆alkyl, C₁-C₆alkylamino, di-C₁-C₆alkylamino, C₁-C₆alkylamino-C₁-C₆alkyl, di-C₁-C₆alkylamino-C₁-C₆alkyl, C₁-C₆haloalkylamino-C₁-C₆alkyl, C₃-C₈cycloalkylamino, C₃-C₈cycloalkylamino-C₁-C₆alkyl, C₁-C₆alkylcarbonyl, C₁-C₆haloalkoxy-C₁-C₆alkyl, C₁-C₆hydroxyalkyl, C₂-C₆hydroxyalkenyl, C₂-C₆hydroxyalkynyl, C₃-C₈halocycloalkoxy, C₃-C₈cycloalkyl-C₁-C₆alkoxy, C₂-C₆alkenyloxy, C₂-C₆haloalkenyloxy, C₂-C₆alkynyloxy, C₂-C₆haloalkynyloxy, C₁-C₆alkoxy-C₁-C₆alkoxy, C₁-C₆alkylcarbonylalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₈cycloalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₃-C₈cycloalkylsulfonyl, C₃-C₈cycloalkylsulfinyl, tri-C₁-C₆alkylsilyl, C₁-C₆alkylsulfonylamino, C₁-C₆haloalkylsulfonylamino, C₁-C₆alkylcarbonylthio, C₁-C₆alkylsulfonyloxy, C₁-C₆alkylsulfinyloxy, C₆-C₁₀arylsulfonyloxy, C₆-C₁₀arylsulfinyloxy, C₆-C₁₀arylsulfonyl, C₆-C₁₀arylsulfinyl, C₆-C₁₀aryltio, C₁-C₆cyanoalkyl, C₂-C₆alkenylcarbonyloxy, C₁-C₆alkoxy-C₁-C₆alkylthio, C₁-C₆alkylthio-C₁-C₆alkoxy, C₂-C₆haloalkenylcarbonyloxy, C₁-C₆alkoxycarbonyl-C₁-C₆alkyl, C₁-C₆alkoxy-C₂-C₆alkynyl, C₂-C₆alkynylthio, C₃-C₈halocycloalkylcarbonyloxy, C₂-C₆alkenylamino, C₂-C₆alkynylamino, C₁-C₆haloalkylamino, C₃-C₈cycloalkyl-C₁-C₆alkylamino, C₁-C₆alkoxyamino, C₁-C₆haloalkoxyamino, C₁-C₆alkoxycarbonylamino, C₁-C₆alkylcarbonyl-C₁-C₆alkylamino, C₁-C₆haloalkylcarbonyl-C₁-C₆alkylamino, C₁-C₆alkoxycarbonyl-C₁-C₆alkylamino, C₂-C₆alkenylthio, C₁-C₆alkoxy-C₁-C₆alkylcarbonyl, C₁-C₆haloalkoxycarbonylamino, di(C₁-C₆haloalkyl)amino-C₁-C₆alkyl, C₃-C₈halocycloalkenyloxy-C₁-C₆alkyl, C₁-C₆alkoxy(C₁-C₆alkyl)aminocarbonyl, C₁-C₆haloalkylsulfonylaminocarbonyl, C₁-C₆alkylsulfonylaminocarbonyl, C₁-C₆alkoxycarbonylalkoxy, C₁-C₆alkylaminothiocarbonylamino, C₃-C₈cycloalkyl-C₁-C₆alkylamino-C₁-C₆alkyl, C₁-C₆alkylthiocarbonyl, C₃-C₈cycloalkenyloxy-C₁-C₆alkyl, C₁-C₆alkoxy-C₁-C₆alkoxycarbonyl, di-C₁-C₆alkylaminothiocarbonylamino, C₁-C₆haloalkoxy-C₁-C₆haloalkoxy, C₁-C₆alkoxy-C₁-C₆haloalkoxy, C₃-C₈halocycloalkoxy-C₁-C₆alkyl, di-C₁-C₆alkylaminocarbonylamino, C₁-C₆alkoxy-C₂-C₆alkenyl, C₁-C₆alkylthiocarbonyloxy, C₁-C₆haloalkoxy-C₁-C₆alkoxy, C₁-C₆haloalkylsulfonyloxy, C₁-C₆alkoxy-C₁-C₆haloalkyl, di(C₁-C₆haloalkyl)amino, di-C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₆alkylaminocarbonylamino, C₁-C₆haloalkoxy-C₁-C₆haloalkyl, C₁-C₆alkylaminocarbonyl-C₁-C₆alkylamino, tri-C₁-C₆alkylsilyl-C₂-C₆alkynyloxy, tri-C₁-C₆alkylsilyloxy, tri-C₁-C₆alkylsilyl-C₂-C₆alkynyl, cyano(C₁-C₆alkoxy)-C₁-C₆alkyl, di-C₁-C₆alkylthio-C₁-C₆alkyl, C₁-C₆alkoxysulfonyl, C₃-C₈halocycloalkoxycarbonyl, C₁-C₆alkyl-C₃-C₈cycloalkylcarbonyl, C₃-C₈halocycloalkylcarbonyl, C₂-C₆alkenyloxycarbonyl, C₂-C₆alkynyloxycarbonyl, C₁-C₆cyanoalkoxycarbonyl, C₁-C₆alkylthio-C₁-C₆alkoxycarbonyl, C₂-C₆alkynylcarbonyloxy, C₂-C₆haloalkynylcarbonyloxy, -cyanocarbonyloxy, C₁-C₆cyanoalkylcarbonyloxy, C₃-C₈cycloalkylsulfonyloxy, C₃-C₈cycloalkyl-C₁-C₆alkylsulfonyloxy, C₃-C₈halocycloalkylsulfonyloxy, C₂-C₆alkenylsulfonyloxy, C₂-C₆alkynylsulfonyloxy, C₁-C₆cyanoalkylsulfonyloxy, C₂-C₆haloalkenylsulfonyloxy, C₂-C₆haloalkynylsulfonyloxy, C₂-C₆alkynylcycloalkyloxy, C₂-C₆cyanoalkenyloxy, C₂-C₆cyanoalkynyloxy, C₁-C₆alkoxycarbonyloxy, C₂-C₆alkenyloxycarbonyloxy, C₂-C₆alkynyloxycarbonyloxy, C₁-C₆alkoxy-C₁-C₆alkylcarbonyloxy, sulfilimines, sulfoximines, -OR¹², -NR¹³R¹⁴, nitro, -SH, -SCN, -C(=O)R¹⁵, -C(=O)OR¹², -C(=O)NR¹³R¹⁴, -NR¹³C(=O)R¹⁵, -O(C=O)R¹⁵, -O(C=O)NR¹³R¹⁴, -C(=NOR¹³)R¹⁵, -NR¹³SO₂R¹⁶,-CSR¹⁶, -C(=S)OR¹², -C(=S)NR¹³R¹⁴, -NR¹³C(=S)R¹⁵, -O(C=S)R¹⁵, -O(C=S)NR¹³R¹⁴, -O(C=S)SR¹⁶, -N=C(R¹⁵)₂, -NHCN, -SO₂NHCN, -C(=O)NHCN, -C(=S)NHCN, -C(=S(O))NHCN, -SO₂R¹⁵, -SO₂NR¹²R¹³, S.F.₅ and Z¹Q¹;

Z ¹ represents a direct bond, CR ^2d R ^3d , N, O, C(O), C(S), C(=CR ^2d R ^3d ) or S(O) _0-2 ;

Q ¹ is selected from phenyl, benzyl, naphthalene, 5- or 6-membered aromatic ring system, 8-11 membered aromatic polycyclic ring system, 8-11 membered aromatic fused ring system, 5- or 6-membered heteroaromatic ring system, 8- an 11-membered heteroaromatic polycyclic ring system or an 8-11 membered heteroaromatic fused ring system; wherein the heteroatom within the heteroaromatic rings is selected from N, O or S, and each ring or ring system may be optionally substituted with one or more R ⁷ groups; or

Q ¹ is selected from a 3-7 membered non-aromatic carbocyclic ring system, a 4-, 5-, 6- or 7-membered non-aromatic heterocyclic ring system, an 8-15 membered non-aromatic polycyclic ring system, a 5-15 membered spirocyclic ring system, or an 8- 15-membered non-aromatic fused ring system, wherein the heteroatom of the non-aromatic rings is selected from N, O or S(O) _0-2 , and the C ring member of the non-aromatic carbocyclic or non-aromatic heterocyclic rings or ring systems may be replaced by C( O), C(S), C(=CR ^2c R ^3c ) or C(=NR ^6b ), and each ring or ring system may be optionally substituted with one or more R ⁷ groups;

R ⁷ , R ^8a , R ^8b and R ^8c are selected from hydrogen, halogen, hydroxy, cyano, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkynyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, C ₁ -C ₆ alkyl-C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkyl-C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkyl-C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkyl-C ₃ -C ₈ cycloalkyl-C ₁ - C ₆ alkyl, C ₃ -C ₈ cycloalkenyl, C ₃ -C ₈ halocycloalkenyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkyl-C ₁ -C ₆ thioalkyl, C ₁ -C ₆ alkylsulfinyl-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylsulfonyl-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylamino, di-C ₁ -C ₆ alkylamino, C ₁ -C ₆ alkylamino-C ₁ -C ₆ alkyl, di-C ₁ -C ₆ alkylamino-C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkylamino-C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkylamino, C ₃ -C ₈ cycloalkylamino-C ₁ -C ₆ alkyl, C ₁ - C ₆ alkylcarbonyl, C ₁ -C ₆ haloalkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ hydroxyalkyl, C 2 -C ₆ hydroxyalkyl, C _{2 -C 6} hydroxyalkynyl, C ₃ -C ₈ halocycloalkoxy, C ₃ -C ₈ cycloalkyl-C ₁ -C ₆ alkoxy, C ₂ -C ₆ alkenyloxy, C ₂ -C ₆ haloalkenyloxy, C ₂ -C ₆ alkynyloxy, C ₂ -C ₆ haloalkynyloxy, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylcarbonylalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₃ -C ₈ cycloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl , C ₁ -C ₆ haloalkylsulfonyl, C ₃ -C ₈ cycloalkylsulfonyl, C ₃ -C ₈ cycloalkylsulfinyl, tri-C 1 -C ₆ alkylsilyl, C ₁ -C ₆ alkylsulfonylamino, C _{1 -C 6} haloalkylsulfonylamino, C ₁ -C ₆ alkylcarbonylthio, C ₁ -C ₆ alkylsulfonyloxy, C ₁ -C ₆ alkylsulfinyloxy, C ₆ -C ₁₀ arylsulfonyloxy, C ₆ -C ₁₀ arylsulfinyloxy, C ₆ -C ₁₀ arylsulfonyl, C ₆ -C ₁₀ arylsulfinyl, C ₆ -C ₁₀ arylthio , C ₁ -C ₆ cyanoalkyl, C ₂ -C ₆ alkenylcarbonyloxy, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylthio-C ₁ -C ₆ alkoxy, C ₂ -C ₆ haloalkenylcarbonyloxy, C ₁ -C ₆ alkoxycarbonyl-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy-C ₂ -C ₆ alkynyl, C ₂ -C ₆ alkynylthio, C ₃ -C ₈ halocycloalkylcarbonyloxy, C ₂ -C ₆ alkenylamino, C ₂ -C ₆ alkynylamino, C ₁ -C ₆ haloalkylamino, C ₃ -C ₈ cycloalkyl-C ₁ -C ₆ alkylamino, C 1 -C ₆ alkoxyamino, C ₁ -C ₆ haloalkoxyamino, C _{1 -C 6} alkoxycarbonylamino, C ₁ -C ₆ alkylcarbonyl-C ₁ -C ₆ alkylamino, C ₁ -C ₆ haloalkylcarbonyl-C ₁ -C ₆ alkylamino, C ₁ -C ₆ alkoxycarbonyl-C ₁ -C ₆ alkylamino, C ₂ -C ₆ alkenylthio, C ₁ - C ₆ alkoxy-C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ haloalkoxycarbonylamino, di(C ₁ -C ₆ haloalkyl)amino-C ₁ -C ₆ alkyl, C ₃ -C ₈ halocycloalkenyloxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy(C ₁ -C ₆ alkyl)aminocarbonyl, C ₁ -C ₆ haloalkylsulfonylaminocarbonyl, C ₁ -C ₆ alkylsulfonylaminocarbonyl, C ₁ -C ₆ alkoxycarbonylalkoxy, C ₁ -C ₆ alkylaminothiocarbonylamino, C ₃ -C ₈ cycloalkyl -C ₁ -C ₆ alkylamino-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylthiocarbonyl, C ₃ -C ₈ cycloalkenyloxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkoxycarbonyl, di-C ₁ -C ₆ alkylaminothiocarbonylamino, C ₁ -C ₆ haloalkoxy-C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkoxy-C ₁ -C ₆ haloalkoxy, C ₃ -C ₈ halocycloalkoxy-C ₁ -C ₆ alkyl , di-C ₁ -C ₆ alkylaminocarbonylamino, C ₁ -C ₆ alkoxy-C ₂ -C ₆ alkenyl, C ₁ -C _{6 alkylthiocarbonyloxy, C 1 -C 6 haloalkoxy -} C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkylsulfonyloxy, C ₁ -C ₆ alkoxy-C ₁ -C ₆ haloalkyl, di(C ₁ -C ₆ haloalkyl)amino, di-C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylaminocarbonylamino, C ₁ -C ₆ haloalkoxy-C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkylaminocarbonyl-C ₁ -C ₆ alkylamino, tri-C ₁ -C ₆ alkylsilyl-C ₂ -C ₆ alkynyloxy, tri-C ₁ -C ₆ alkylsilyloxy, tri-C ₁ -C ₆ alkylsilyl-C ₂ -C ₆ alkynyl, cyano(C ₁ -C ₆ alkoxy)-C ₁ -C ₆ alkyl, di-C ₁ -C ₆ alkylthio-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxysulfonyl, C ₃ -C ₈ halocycloalkoxycarbonyl, C ₁ -C ₆ alkyl-C ₃ -C ₈ cycloalkylcarbonyl, C ₃ -C ₈ halocycloalkylcarbonyl, C ₂ -C ₆ alkenyloxycarbonyl, C ₂ -C ₆ alkynyloxycarbonyl , C ₁ -C ₆ cyanoalkoxycarbonyl, C ₁ -C ₆ alkylthio-C ₁ -C ₆ alkoxycarbonyl, C 2 -C ₆ alkynylcarbonyloxy, C ₂ -C ₆ haloalkynylcarbonyloxy, cyanocarbonyloxy, C _{1 -C 6} cyanoalkylcarbonyloxy, C ₃ -C ₈ cycloalkylsulfonyloxy, C ₃ -C ₈ cycloalkyl-C ₁ -C ₆ alkylsulfonyloxy, C ₃ -C ₈ halocycloalkylsulfonyloxy, C ₂ -C ₆ alkenylsulfonyloxy, C ₂ -C ₆ alkynylsulfonyloxy, C ₁ -C ₆ cyanoalkylsulfonyloxy, C ₂ -C ₆ haloalkenylsulfonyloxy , C ₂ -C ₆ haloalkynylsulfonyloxy, C ₂ -C ₆ alkynylcycloalkyloxy, C ₂ -C ₆ cyanoalkenyloxy, C ₂ -C ₆ cyanoalkynyloxy, C ₁ -C ₆ alkoxycarbonyloxy, C ₂ -C ₆ alkenyloxycarbonyloxy, C ₂ -C ₆ alkynyloxycarbonyloxy, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkylcarbonyloxy, sulfilimines, sulfoximines, SF ₅ , -OR ¹² , -NR ¹³ R ¹⁴ , nitro, -SH, -SCN, -C(=O)R ¹⁵ , -C (=O)OR ¹² , -C(=O)NR ¹³ R ¹⁴ , -NR ¹³ C(=O)R ¹⁵ , -O(C=O)R ¹⁵ , -O(C=O)NR ¹³ R ¹⁴ , -C(=NOR ¹³ )R ¹⁵ , -NR ¹³ SO ₂ R ¹⁶ , -CSR ¹⁶ , -C(=S)OR ¹² , -C(=S)NR ¹³ R ¹⁴ , -NR ¹³ C(=S )R ¹⁵ , -O(C=S)R ¹⁵ , -O(C=S)NR ¹³ R ¹⁴ , -O(C=S)SR ¹⁶ , -N=C(R ¹⁵ ) ₂ , -NHCN, - SO ₂ NHCN, -C(=O)NHCN, -C(=S)NHCN, -C(=S(O))NHCN and -SO ₂ NR ¹² R ¹³ ; or

R ^8a and R ^8b ; R ^8a and R ¹⁰ ; R ^8b and R ¹⁰ ; R ^8c and R ¹⁰ ; R ^4b and R ¹⁰ ; R ^2f and R ¹⁰ or R ^3f and R ¹⁰ together with the atoms to which they are attached can form a 3-8 membered heterocyclic ring or ring system, where the heteroatom is selected from the group consisting of N, O and S(O) _{0 -2} , and the C ring member of the heterocyclic ring or ring system may be replaced by C(O), C(S), C(=CR ^2c R ^3c ) or C(=NR ^6b ), and said heterocyclic ring or the ring system may be optionally substituted with halogen, cyano, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ haloalkenyl, C ₂ -C ₄ haloalkynyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy;

R ¹² is selected from the group consisting of C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₈ cycloalkyl and C ₃ -C ₈ halocycloalkyl;

R ¹³ and R ¹⁴ are independently selected from the group consisting of hydrogen, hydroxyl, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, phenyl and a 5- or 6-membered heterocyclic ring; wherein said phenyl, 5- or 6-membered heterocyclic ring may be optionally substituted with halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl and C ₁ -C ₆ alkylthio; or

R¹³ and R¹⁴ together with the N atom to which they are attached, they can form a 3-7-membered heterocyclic ring; where the heteroatom of the heterocyclic ring is selected from N, O or S(O)_0-2, and the C ring member of the heterocyclic ring can be replaced C(O) and C(S), wherein said heterocyclic ring may be optionally substituted with halogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl and C₁-C₆alkylthio;

R ¹⁵ is hydrogen, hydroxy, halogen, amino, C ₁ -C ₆ alkylamino, di-C ₁ -C ₆ alkylamino, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₃ -C ₈ cycloalkyl _, C ₃ -C ₈ cycloalkyl, phenyl, 5- or 6-membered heterocyclic ring, wherein said phenyl, 3-6-membered heterocyclic ring may be optionally substituted with halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl and C ₁ -C ₆ alkylthio;

R¹⁶ represents hydrogen, halogen, cyano, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₈cycloalkyl and C₃-C₈cycloalkyl;

and/or its N-oxides, metal complexes, isomers, polymorphs or agriculturally acceptable salts.

In one embodiment, the present invention provides a compound of formula (I), wherein

R ¹ represents C ₁ -haloalkyl, where halogen represents chlorine or fluorine;

L ¹ represents a direct connection;

L ² represents a direct connection;

A is a 3-6 membered aromatic carbocyclic ring or an aromatic heterocyclic ring, wherein the heteroatom of the aromatic heterocyclic ring is selected from N, O and S; and A is optionally substituted with one or more identical or different R ^A groups;

R ^A is selected from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy, SF ₅ , C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₈ cycloalkyl , C ₃ -C ₈ cycloalkylalkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy-C 1 -C ₄ alkyl, C ₁ -C ₆ hydroxyalkyl, C ₂ -C ₆ haloalkenyl, C _{2 -C 6} haloalkynyl, C ₃ -C ₈ halocycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ haloalkoxycarbonyl and C ₁ -C ₆ alkylthio;

W ¹ represents O;

Q represents direct connection, O, S(=O) _0-2 , S(=O) _0-1 (=NR ^4b ), NR ^4b , CR ^2e R ^3e , -N=S(=NR ^8a )(R ^8b )-; -N=S(=O) _0-1 (R ^8c )-.

R ¹⁰ is selected from the group consisting of halogen, hydroxy, cyano, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C 2 -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C _{2 -C 6} haloalkenyl, C ₂ -C ₆ haloalkynyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, C ₁ -C ₆ alkyl-C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkyl-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkyl-C ₃ -C ₈ cycloalkyl-C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkenyl, C ₃ -C ₈ halocycloalkenyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkoxy-C ₁ - C ₆ alkyl, C ₃ -C ₈ cycloalkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkyl-C ₁ -C ₆ thioalkyl, C ₁ -C ₆ alkylsulfinyl-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylsulfonyl-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylamino, di-C ₁ -C ₆ alkylamino, C ₁ -C ₆ alkylamino-C ₁ -C ₆ alkyl, di-C ₁ -C ₆ alkylamino-C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkylamino-C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkylamino, C ₃ -C ₈ cycloalkylamino-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ hydroxyalkyl, C ₂ -C ₆ hydroxyalkyl, C ₂ -C ₆ hydroxyalkynyl, C 2 -C ₆ alkenyloxy, C ₂ -C _{6 haloalkenyloxy, C 2 -C 6 alkynyloxy ,} C _{2 -C 6} haloalkynyloxy, C ₁ - C ₆ alkylcarbonylalkoxy, C ₁ -C ₆ alkylthio, _{C 1} -C ₆ haloalkylthio, C ₃ -C ₈ cycloalkylthio, C 1 -C 6 alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C _{1 -C 6} alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, C ₃ -C ₈ cycloalkylsulfonyl, C ₃ -C ₈ cycloalkylsulfinyl, tri-C ₁ -C ₆ alkylsilyl, C ₁ -C ₆ alkylsulfonylamino, C ₁ -C ₆ haloalkylsulfonylamino, C ₁ -C ₆ alkylcarbonylthio, C ₁ - C ₆ alkylsulfonyloxy, C ₁ -C ₆ alkylsulfinyloxy, C ₆ -C ₁₀ arylsulfonyloxy, C ₆ -C ₁₀ arylsulfinyloxy, C ₆ -C ₁₀ arylsulfonyl, C ₆ -C ₁₀ arylsulfinyl, C ₆ -C ₁₀ arylthio, C ₁ -C ₆ cyanoalkyl, C ₂ -C ₆ alkynylthio, C ₂ -C ₆ alkenylamino, C ₂ -C _{6 alkynylamino, C 1 -C 6} haloalkylamino, C ₁ -C ₆ alkoxyamino _, C ₁ -C ₆ haloalkoxyamino, C _{1 -C 6} alkoxycarbonylamino, C ₂ -C ₆ alkenylthio, SF ₅ , -OR ¹² , -NR ¹³ R ¹⁴ , nitro, -SH, -SCN, -C(=O)R ¹⁵ , -C(=O)OR ¹² , -C (=O)NR ¹³ R ¹⁴ , -NR ¹³ C(=O)R ¹⁵ and Z ¹ Q ¹ .

In another embodiment, the present invention provides compounds of formula (I), wherein

R ¹ represents C ₁ -haloalkyl, where halogen represents chlorine or fluorine;

L ¹ represents a direct connection;

L ² represents a direct connection;

A is phenyl or pyridyl; wherein said phenyl or pyridyl ring may be optionally substituted with one or more identical or different R ^A groups;

R ^A is selected from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy, SF ₅ , C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ hydroxyalkyl , C ₃ -C ₈ halocycloalkyl, C ₁ -C ₆ alkoxy and C ₁ -C ₆ haloalkoxy;

W ¹ represents O;

Q represents the direct link, O, S(=O) _0-2 , S(=O) _0-1 (=NR ^4b ), NR ^4b and CR ^2e R ^3e ;

R ¹⁰ is selected from the group consisting of halogen, hydroxy, cyano, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C 2 -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C _{2 -C 6} haloalkenyl, C ₂ -C ₆ haloalkynyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, C ₁ -C ₆ alkyl-C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkyl-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkyl-C ₃ -C ₈ cycloalkyl-C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkenyl, C ₃ -C ₈ halocycloalkenyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkoxy-C ₁ - C ₆ alkyl, C ₃ -C ₈ cycloalkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkyl-C ₁ -C ₆ thioalkyl, C ₁ -C ₆ alkylsulfinyl-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylsulfonyl-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylamino, di-C ₁ -C ₆ alkylamino, C ₁ -C ₆ alkylamino-C ₁ -C ₆ alkyl, di-C ₁ -C ₆ alkylamino-C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkylamino-C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkylamino, C ₃ -C ₈ cycloalkylamino-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ hydroxyalkyl, C ₂ -C ₆ hydroxyalkyl, C ₂ -C ₆ hydroxyalkynyl, C 2 -C ₆ alkenyloxy, C ₂ -C _{6 haloalkenyloxy, C 2 -C 6 alkynyloxy ,} C _{2 -C 6} haloalkynyloxy, C ₁ - C ₆ alkylcarbonylalkoxy, C ₁ -C ₆ alkylthio, _{C 1} -C ₆ haloalkylthio, C ₃ -C ₈ cycloalkylthio, C 1 -C 6 alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C _{1 -C 6} alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, C ₃ -C ₈ cycloalkylsulfonyl, C ₃ -C ₈ cycloalkylsulfinyl, tri-C ₁ -C ₆ alkylsilyl, C ₁ -C ₆ alkylsulfonylamino, C ₁ -C ₆ haloalkylsulfonylamino, C ₁ -C ₆ alkylcarbonylthio, C ₁ - C ₆ alkylsulfonyloxy, C ₁ -C ₆ alkylsulfinyloxy, C ₆ -C ₁₀ arylsulfonyloxy, C ₆ -C ₁₀ arylsulfinyloxy, C ₆ -C ₁₀ arylsulfonyl, C ₆ -C ₁₀ arylsulfinyl, C ₆ -C ₁₀ arylthio, C ₁ -C ₆ cyanoalkyl, C ₂ -C ₆ alkynylthio, C ₂ -C ₆ alkenylamino, C ₂ -C _{6 alkynylamino, C 1 -C 6} haloalkylamino, C ₁ -C ₆ alkoxyamino _, C ₁ -C ₆ haloalkoxyamino, C _{1 -C 6} alkoxycarbonylamino, C ₂ -C ₆ alkenylthio, SF ₅ , -OR ¹² , -NR ¹³ R ¹⁴ , nitro, -SH, -SCN, -C(=O)R ¹⁵ , -C(=O)OR ¹² , -C (=O)NR ¹³ R ¹⁴ , -NR ¹³ C(=O)R ¹⁵ and Z ¹ Q ¹ .

In a preferred embodiment, the compound of formula (I) is selected from 2-phenoxy-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2-fluorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(4-methoxyphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(4-bromophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(4-chlorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2,6-dichlorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(3-bromo-4-methylphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(3-fluorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(4-fluorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(m-tolyloxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2-methoxyphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(4-bromo-3-fluorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(4-chloro-3-(trifluoromethyl)phenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2,6-dichlorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3-methoxyphenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(3,5-dichlorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2,5-dimethylphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(5-chloro-2-methylphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2,4-difluorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2-chloro-4-fluorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2,4-dichlorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(pyridin-3-yloxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(p-tolylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-methoxyphenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(cyclopentylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(benzo[d]oxazol-2-ylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-methylthiazol-2-yl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3,4-difluorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethyl)phenyl)amino)ethan-1-one; 2-((2-fluorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3-methoxyphenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2-chloro-5-methylphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(p-tolyloxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(3-chlorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-(trifluoromethyl)phenoxy)ethan-1-one; 2-(3-methoxyphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2,4-dimethylphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(o-tolyloxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(3-(trifluoromethyl)phenoxy)ethan-1-one; 2-(3-fluoro-5-methylphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(3-chloro-5-fluorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2-chloro-4-methoxyphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2-chloropyridin-4-yl)oxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((6-methyl-3-(trifluoromethyl)pyridin-2-yl)oxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane- 1-she; 2-((2-chloropyridin-3-yl)oxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((6-fluoropyridin-3-yl)oxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((5-bromopyridin-3-yl)oxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((6-bromopyridin-3-yl)oxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((1-methyl-1H-pyrazol-3-yl)oxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 2-((4-chloropyridin-3-yl)oxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3,4-dichlorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-chlorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3-chlorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3,4-difluorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(benzylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-methoxybenzyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((1-phenylethyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(cyclohexylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(phenylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(allylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3-(trifluoromethyl)phenyl)thio)ethan-1-one; 2-((2-methoxyphenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3-fluorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2-fluorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(o-tolylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(m-tolylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(pyridin-4-ylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(isopropylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(tert-butylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethyl)phenyl)thio)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethyl)pyrimidin-2-yl)thio)ethan-1-one; 2-(thiazol-2-ylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(pyridin-2-ylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-methyl-4H-1,2,4-triazol-3-yl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl )ethan-1-one; 2-((1,3,4-thiadiazol-2-yl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; 2-((4-chlorophenyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3,4-difluorophenyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(benzylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-methoxybenzyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((1-phenylethyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((5-methylthiazol-2-yl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(phenylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3-(trifluoromethyl)phenyl)sulfinyl)ethan-1-one; 2-(p-tolylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3-fluorophenyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2-fluorophenyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(o-tolylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(m-tolylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(tert-butylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethyl)phenyl)sulfinyl)ethan-1-one; 2-(isopropylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3,4-dichlorophenyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-chlorophenyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3,4-difluorophenyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(benzylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-methoxybenzyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((1-phenylethyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(cyclohexylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((5-methylthiazol-2-yl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(phenylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3-(trifluoromethyl)phenyl)sulfonyl)ethan-1-one; 2-(o-tolylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3-fluorophenyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(isopropylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(thiazol-2-ylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(tert-butylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethyl)phenyl)sulfonyl)ethan-1-one; 2-(m-tolylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2-fluorophenyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(pyridin-4-ylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-hydroxy-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2-fluorophenoxy)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((3-fluorophenyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((4-methoxyphenyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((4-methoxybenzyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-(benzylthio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-(cyclopentylthio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((2,6-dichlorophenyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-(benzo[d]oxazol-2-ylthio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((4-(trifluoromethoxy)phenyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((4-methoxyphenyl)sulfonyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((4-methoxybenzyl)sulfonyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-(benzylsulfonyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-(cyclopentylsulfonyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((3-fluorophenyl)sulfonyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((3-fluorophenyl)sulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((4-methoxyphenyl)sulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((4-methoxybenzyl)sulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-(benzylsulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((2,6-dichlorophenyl)sulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-(cyclopentylsulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 4-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; 2-(4-methylpiperazin-1-yl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-morpholino-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(phenylamino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-fluorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2,4-difluorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-chloro-3-(trifluoromethyl)phenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3-(trifluoromethyl)phenyl)amino)ethan-1-one; 2-((4-chlorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3-fluorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(m-tolylamino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-methoxyphenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(o-tolylamino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2-methoxyphenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(pyrimidin-2-ylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((1H-benzo[d]imidazol-2-yl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 2-((1,3,4-thiadiazol-2-yl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 2-((4'-fluoro-[1,1'-biphenyl]-3-yl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl )ethan-1-one; 1-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyrrolidin-2-one; 1-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidin-2-one; 4-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)morpholin-3-one; 1-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)azetidin-2-one; 2-fluoro-N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; N,3-dimethyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyrimidine-5-sulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyridazine-4-sulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)methanesulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyrazine-2-sulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyridine-4-sulfonamide; N,1-dimethyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-1H-pyrazole-4-sulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-1-phenylmethanesulfonamide; 3-(dimethylamino)-N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; 4-chloro-N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; 4-methoxy-N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)ethanesulfonamide; 2,4-difluoro-N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; N,2-dimethyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)propane-2-sulfonamide; 1-cyclopropyl-N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)methanesulfonamide; N,1-dimethyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-1H-imidazole-4-sulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)isoxazole-4-sulfonamide; 2-fluoro-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; 3-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyrimidine-5-sulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyridazine-4-sulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)methanesulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyrazine-2-sulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyridine-4-sulfonamide; 1-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-1H-pyrazole-4-sulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-1-phenylmethanesulfonamide; 3-(dimethylamino)-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; 4-chloro-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; 4-methoxy-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)ethanesulfonamide; 2,4-difluoro-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; 2-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)propane-2-sulfonamide; 1-cyclopropyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)methanesulfonamide; 1-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-1H-imidazole-4-sulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)isoxazole-4-sulfonamide; 2-fluoro-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzamide; 3-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyrimidine-5-carboxamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyridazine-4-carboxamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)acetamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyrazine-2-carboxamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)isonicotinamide; 1-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-1H-pyrazole-4-carboxamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-2-phenylacetamide; 3-(dimethylamino)-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzamide; 4-chloro-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzamide; 4-methoxy-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)propionamide; 2,4-difluoro-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pivalamide; 2-cyclopropyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)acetamide; 1-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-1H-imidazole-4-carboxamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)isoxazole-4-carboxamide; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(phenylamino)ethan-1-one; 2-((2-chloro-4-fluorophenyl)amino)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyridin-3-ylamino)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyrimidin-5-ylamino)ethan-1-one; 2-((2-chloro-6-methoxyphenyl)amino)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2,4-dichlorophenyl)amino)ethan-1-one; 2-((2-chloro-4-methoxyphenyl)amino)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(p-tolylamino)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2,4-difluorophenyl)amino)ethan-1-one; 2-((3-chloro-4-(trifluoromethyl)phenyl)amino)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxyphenyl)amino)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2,6-dichlorophenyl)amino)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-fluorophenyl)amino)ethan-1-one; 2-((2-chloro-4-(trifluoromethyl)phenyl)amino)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethoxy)phenyl)amino)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyrimidin-5-ylsulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2,6-dichlorophenyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3,3,3-trifluoropropyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(methylsulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-fluorophenyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyridin-3-ylsulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(phenylsulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(isopropylsulfonyl)ethan-1-one; 2-((2-chloro-4-(trifluoromethyl)phenyl)sulfonyl)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethoxy)phenyl)sulfonyl)ethan-1-one; 2-((2-chloro-6-methoxyphenyl)sulfonyl)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2,4-difluorophenyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxyphenyl)sulfonyl)ethan-1-one; 2-((3-chloro-4-(trifluoromethyl)phenyl)sulfonyl)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(tert-butylsulfonyl)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2-chloro-4-fluorophenyl)sulfonyl)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2-methoxyethyl)sulfonyl)ethan-1-one; 2-(benzylsulfonyl)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((cyclopropylmethyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(ethylsulfonyl)ethan-1-one; 2-((4-chlorobenzyl)sulfonyl)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methylbenzyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxybenzyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1H-pyrazol-4-yl)methyl)sulfonyl)ethane- 1-she; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1H-imidazol-4-yl)methyl)sulfonyl)ethane- 1-she; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1H-1,2,4-triazol-3-yl) methyl)sulfonyl)ethan-1-one; 2-(((1,2,4-oxadiazol-3-yl)methyl)sulfonyl)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane- 1-she; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((oxazol-4-ylmethyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((isoxazol-4-ylmethyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((thiazol-4-ylmethyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyrimidin-5-ylthio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2,6-dichlorophenyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3,3,3-trifluoropropyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(methylthio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-fluorophenyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyridin-3-ylthio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(phenylthio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(isopropylthio)ethan-1-one; 2-((2-chloro-4-(trifluoromethyl)phenyl)thio)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethoxy)phenyl)thio)ethan-1-one; 2-((2-chloro-6-methoxyphenyl)thio)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2,4-difluorophenyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxyphenyl)thio)ethan-1-one; 2-((3-chloro-4-(trifluoromethyl)phenyl)thio)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(tert-butylthio)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2-chloro-4-fluorophenyl)thio)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2-methoxyethyl)thio)ethan-1-one; 2-(benzylthio)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((cyclopropylmethyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(ethylthio)ethan-1-one; 2-((4-chlorobenzyl)thio)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methylbenzyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxybenzyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1H-pyrazol-4-yl)methyl)thio)ethane- 1-she; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1H-imidazol-4-yl)methyl)thio)ethane- 1-she; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1H-1,2,4-triazol-3-yl) methyl)thio)ethan-1-one; 2-(((1,2,4-oxadiazol-3-yl)methyl)thio)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane- 1-she; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((oxazol-4-ylmethyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((isoxazol-4-ylmethyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((thiazol-4-ylmethyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyrimidin-5-yloxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(2,6-dichlorophenoxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(3,3,3-trifluoropropoxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-methoxyethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-fluorophenoxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyridin-3-yloxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-phenoxyethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-isopropoxyethan-1-one; 2-(2-chloro-4-(trifluoromethyl)phenoxy)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-(trifluoromethoxy)phenoxy)ethan-1-one; 2-(2-chloro-6-methoxyphenoxy)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(2,4-difluorophenoxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-methoxyphenoxy)ethan-1-one; 2-(3-chloro-4-(trifluoromethyl)phenoxy)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(tert-butoxy)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2-chloro-4-fluorophenoxy)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(2-methoxyethoxy)ethan-1-one; 2-(benzyloxy)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(cyclopropylmethoxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-ethoxyethan-1-one; 2-((4-chlorobenzyl)oxy)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methylbenzyl)oxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxybenzyl)oxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-pyrazol-4-yl)methoxy)ethan-1-one ; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-imidazol-4-yl)methoxy)ethan-1-one ; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-1,2,4-triazol-3-yl)methoxy )ethan-1-one; 2-((1,2,4-oxadiazol-3-yl)methoxy)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(oxazol-4-ylmethoxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(isoxazol-4-ylmethoxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(thiazol-4-ylmethoxy)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyridin-3-ylthio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxybenzyl)thio)ethan-1-one; 2-((2-chloro-4-(trifluoromethyl)phenyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane- 1-she; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyrimidin-5-ylthio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxyphenyl)thio)ethan-1-one; 2-((2-chloro-4-fluorophenyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 2-(tert-butylthio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-fluorophenyl)thio)ethan-1-one; 2-(benzylthio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methylbenzyl)thio)ethan-1-one; 2-((2,6-dichlorophenyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-chlorobenzyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2-chloro-6-methoxyphenyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethoxy)phenyl)thio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1H-imidazol-4-yl)methyl) thio)ethan-1-one; 2-((3-chloro-4-(trifluoromethyl)phenyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane- 1-she; 2-((2,4-difluorophenyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1H-pyrazol-4-yl)methyl) thio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(phenylthio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((thiazol-4-ylmethyl)thio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((oxazol-4-ylmethyl)thio)ethan-1-one; 2-(((1,2,4-oxadiazol-3-yl)methyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl) phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((isoxazol-4-ylmethyl)thio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1H-1,2,4-triazol- 3-yl)methyl)thio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3,3,3-trifluoropropyl)thio)ethan-1-one ; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(methylthio)ethan-1-one; 2-(ethylthio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(isopropylthio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2-methoxyethyl)thio)ethan-1-one; 2-((cyclopropylmethyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyridin-3-yloxy)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxybenzyl)oxy)ethan-1-one; 2-(2-chloro-4-(trifluoromethyl)phenoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyrimidin-5-yloxy)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-methoxyphenoxy)ethan-1-one; 2-(2-chloro-4-fluorophenoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(tert-butoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-fluorophenoxy)ethan-1-one; 2-(benzyloxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methylbenzyl)oxy)ethan-1-one; 2-(2,6-dichlorophenoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-chlorobenzyl)oxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2-chloro-6-methoxyphenoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-(trifluoromethoxy)phenoxy)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-imidazol-4-yl)methoxy)ethane -1-she; 2-(3-chloro-4-(trifluoromethyl)phenoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 2-(2,4-difluorophenoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-pyrazol-4-yl)methoxy)ethane -1-she; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-phenoxyethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(thiazol-4-ylmethoxy)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(oxazol-4-ylmethoxy)ethan-1-one; 2-((1,2,4-oxadiazol-3-yl)methoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane -1-she; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(isoxazol-4-ylmethoxy)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-1,2,4-triazol-3 -yl)methoxy)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(3,3,3-trifluoropropoxy)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-methoxyethan-1-one; 2-ethoxy-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-isopropoxyethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(2-methoxyethoxy)ethan-1-one; 2-(cyclopropylmethoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyridin-3-yloxy)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxybenzyl)oxy)ethan-1-one; 2-(2-chloro-4-(trifluoromethyl)phenoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyrimidin-5-yloxy)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-methoxyphenoxy)ethan-1-one; 2-(2-chloro-4-fluorophenoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(tert-butoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-fluorophenoxy)ethan-1-one; 2-(benzyloxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methylbenzyl)oxy)ethan-1-one; 2-(2,6-dichlorophenoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-chlorobenzyl)oxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2-chloro-6-methoxyphenoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-(trifluoromethoxy)phenoxy)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-imidazol-4-yl)methoxy)ethane -1-she; 2-(3-chloro-4-(trifluoromethyl)phenoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 2-(2,4-difluorophenoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-pyrazol-4-yl)methoxy)ethane -1-she; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-phenoxyethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(thiazol-4-ylmethoxy)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(oxazol-4-ylmethoxy)ethan-1-one; 2-((1,2,4-oxadiazol-3-yl)methoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane -1-she; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(isoxazol-4-ylmethoxy)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-1,2,4-triazol-3 -yl)methoxy)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(3,3,3-trifluoropropoxy)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-methoxyethan-1-one; 2-ethoxy-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-isopropoxyethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(2-methoxyethoxy)ethan-1-one; 2-(cyclopropylmethoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperazin-2-one and 4-methyl-1-(2- oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperazin-2-one.

The compound of the present invention may exist in the form of one or more stereoisomers. The different stereoisomers include enantiomers, diastereomers, atropoisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit a beneficial effect when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). In addition, one skilled in the art knows how to separate, enrich and/or selectively obtain said stereoisomers. The compound of the present invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.

The anionic part of the salt, in case the compound of formula (I) is cationic or capable of forming a cation, may be inorganic or organic. Alternatively, the cationic part of the salt, in case the compound of formula (I) is anionic or anionic, may be inorganic or organic. Examples of the inorganic anionic portion of the salt include, but are not limited to, chloride, bromide, iodide, fluoride, sulfate, phosphate, nitrate, nitrite, hydrogen carbonates, hydrogen sulfates. Examples of the organic anionic salt moiety include, but are not limited to, formate, alkanoates, carbonates, acetates, trifluoroacetate, trichloroacetate, propionate, glycolate, thiocyanate, lactate, succinate, malate, citrates, benzoates, cinnamates, oxalates, alkyl sulfates, alkyl sulfonates, arylsulfonates, aryl disulfonates, alkyl phosphonates, arylphosphonates, aryldiphosphonates, p-toluenesulfonate and salicytate. Examples of the inorganic cationic portion of the salt include, but are not limited to, alkali and alkaline earth metals. Examples of the organic cationic portion of the salt include, but are not limited to, pyridine, methylamine, imidazole, benzimidazole, histidine, phosphazene, tetramethylammonium, tetrabutylammonium, choline and trimethylamine.

The metal ions in the metal complexes of compounds of formula (I) are particularly often ions of elements of the second main group, especially calcium and magnesium, ions of elements of the third and fourth main groups, especially aluminum, tin and lead, and ions of elements of the first to eighth transition groups , especially chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Particular preference is given to metal ions of elements of the fourth period and from the first to eighth transition groups. In this case, metals may be present with different valence values that they can assume.

A 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 that are solids, such as waxes and resins, as well as embodiments that are liquids, such as solutions and melts. Crystal forms include embodiments that are essentially a single type of crystal, and embodiments that are a mixture of polymorphs (ie, different types of crystals). The term "polymorph" means a specific crystalline form of a chemical compound that can crystallize into different crystalline forms characterized by different types of arrangement and/or conformations of molecules in the crystal lattice. Although polymorphs may have the same chemical composition, they may also differ in composition due to the presence or absence of co-crystallized water or other molecules that may be weakly or strongly bound in the lattice. Polymorphs may differ in chemical, physical and biological properties such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspendability, dissolution rate and bioavailability. One skilled in the art will recognize that a polymorph of a compound represented by formula (I) may exhibit beneficial effects (e.g., useful formulation properties, improved biological properties) relative to another polymorph or mixture of polymorphs of the same compound represented by formula (I). . The preparation and isolation of a specific polymorph of the compound represented by formula (I) can be achieved by methods known to those skilled in the art, including, for example, crystallization using selected solvents and temperatures.

In one embodiment, the present invention provides a method for preparing a compound of formula (I).

In one embodiment, the present invention provides a process for preparing a compound of formula (I), comprising the steps of:

a) introducing a protecting group on the carbonyl group of the compound of formula 1 using a suitable protecting agent to obtain a compound of formula 2;

where L ¹ represents a direct link; A is aryl and L ² is a direct bond;

b) reacting a compound of formula 2 with hydroxylamine to produce a compound of formula 3;

where L ¹ represents a direct link; A is aryl and L ² is a direct bond;

c) reacting a compound of formula 3 with a suitable carboxylic acid anhydride of formula a or a carboxylic acid chloride of formula b to produce a compound of formula 4;

where L ¹ represents a direct link; A is aryl and L ² is a direct bond;

d) deprotecting the compound of formula 4 in the presence of a suitable deprotecting agent to obtain the compound of formula 5;

where L ¹ represents a direct link; A is aryl and L ² is a direct bond;

e) halogenating the compound of formula 5 in the presence of a suitable halogenation agent to obtain the compound of formula 6;

where L ¹ represents a direct link; A is aryl and L ² is a direct bond;

f) reacting a compound of formula 6 with a compound of formula (c) to obtain a compound of formula (I);

where L ¹ represents a direct link; A is aryl; L ² represents a direct connection; X represents Br, Cl or I; W ¹ represents O; R ¹ , W ¹ , R ^2f , R ^3f , Q and R ¹⁰ have the same meanings as defined in the detailed description above.

In another embodiment, the present invention provides a process for preparing a compound of formula (I), comprising the steps of:

a) reacting a compound of formula 7 with a compound of formula (e) to obtain a compound of formula 8;

where L ¹ represents a direct link; A is aryl or pyridyl; L ² represents a direct bond, and X represents Br, Cl or I;

b) reacting a compound of formula 8 with hydroxylamine to produce a compound of formula 9;

where L ¹ represents a direct link; A is aryl or pyridyl, and L ² is a direct bond;

c) reacting a compound of formula 9 with a suitable carboxylic acid anhydride of formula a or a carboxylic acid chloride of formula b to obtain a compound of formula 10;

where L ¹ represents a direct link; A is aryl or pyridyl, and L ² is a direct bond;

d) halogenating the compound of formula 10 in the presence of a suitable halogenation agent to obtain the compound of formula 6;

where L ¹ represents a direct link; A is aryl or pyridyl; L ² represents a direct bond, and X represents Br, Cl or I;

e) reacting a compound of formula 6 with a compound of formula (c) to obtain a compound of formula (I);

where L ¹ represents a direct link; A is aryl or pyridyl; L ² represents a direct connection; X represents Br, Cl or I; W ¹ represents O; R ¹ , R ^2f , R ^3f , Q and R ¹⁰ have the same meanings as defined in the detailed description above.

In yet another embodiment, the present invention provides a process for preparing a compound of formula (I), comprising the steps of:

a) reacting a compound of formula 11 with hydroxylamine to produce a compound of formula 12;

where L ¹ represents a direct link; A is aryl or pyridyl, and L ² is a direct bond;

b) reacting a compound of formula 12 with a suitable carboxylic acid anhydride of formula a or a carboxylic acid chloride of formula b to obtain a compound of formula 13;

where L ¹ represents a direct link; A is aryl or pyridyl, and L ² is a direct bond;

c) reacting a compound of formula 13 with a suitable oxidizing agent to obtain a compound of formula 14;

where L ¹ represents a direct link; A is aryl or pyridyl, and L ² is a direct bond;

d) hydrolyzing the compound of formula 14 in the presence of a suitable hydrolyzing agent to obtain the compound of formula 15;

where L ¹ represents a direct link; A is aryl or pyridyl, and L ² is a direct bond;

e) oxidizing the compound of formula 15 in the presence of a suitable oxidizing agent to obtain the compound of formula 16;

where L ¹ represents a direct link; A is aryl or pyridyl, and L ² is a direct bond;

f) reacting a compound of formula 16 with a compound of formula (c) to obtain a compound of formula (I);

where L ¹ represents a direct link; A is aryl or pyridyl; L ² represents a direct connection; W ¹ represents O; R ¹ , R ^2f , R ^3f , Q and R ¹⁰ have the same meanings as defined in the detailed description above.

Connections according to the present invention, defined by general formula (I) and/or in tables 1-8, can be obtained in a known manner using a variety of methods, as described in schemes 1-3.

Scheme 1

where L ¹ represents a direct link; A is aryl; L ² represents a direct connection; X represents Br, Cl or I, and W ¹ represents O; R ¹ , R ^2f , R ^3f , R ¹⁰ and Q have the same meanings as defined in the detailed description above.

The compound of formula 2 can be prepared by protecting the carbonyl compound of formula 1 with ethylene glycol in the presence of N-bromosuccinimide and trimethyl orthoformate at temperatures ranging from ambient temperature to reflux temperature.

The compound of formula 3 can be prepared by reacting the nitrile compound of formula 2 with hydroxylamine in polar protic solvents such as ethanol, methanol, etc. Alternatively, this reaction can also be carried out using hydroxylamine hydrochloride in the presence of organic and inorganic bases , such as triethylamine, diisopropylamine, sodium bicarbonate, etc.

The compound of formula 4 can be prepared by reacting the compound of formula 3 with a carboxylic acid anhydride of formula a. Alternatively, the compound of formula 4 can also be prepared by reacting with the carboxylic acid chloride of formula b. Such reactions are typically carried out in aprotic solvents such as tetrahydrofuran, 1,4-dioxane, dichloromethane, etc., optionally in the presence of bases such as triethylamine, diisopropylamine, etc., at 0-50 °C.

The compound of formula 5 can be prepared by deprotecting the ketal compound of formula 4 in the presence of a suitable deprotecting agent such as catalytic iodine or acid in solvents such as acetone. Typically, this reaction is carried out at 0-30°C.

the compound of formula 6 can be prepared by alpha-halogenation of the carbonyl compound 5 using a suitable halogenation agent such as bromine, N-bromosuccinimide, N-chlorosuccinimide, etc. This reaction is typically carried out in solvents such as dichloromethane at 0 -30°C.

The compound of formula (I) can be prepared by reacting an alpha-halogen compound of formula 6 with a compound of formula R ¹⁰ -QH in the presence of an inorganic base such as potassium carbonate, sodium bicarbonate in solvents such as acetonitrile, dimethylformamide, ethanol, etc. This reaction can be carried out at 0-25 °C, optionally in the presence of potassium iodide, sodium iodide, etc.

Scheme 2

where L ¹ represents a direct link; A is aryl or pyridyl; L ² represents a direct connection; X represents Br, Cl or I and W ¹ represents O; R ¹ , R ^2f , R ^3f , R ¹⁰ and Q have the same meanings as defined in the detailed description above.

The compound of formula 8 can be prepared by reacting the compound of formula 7 with an organostannan compound of formula e in the presence of a Pd(II) reagent such as bis(triphenylphosphine)palladium(II)dichloride. This reaction is usually carried out in solvents such as toluene at a temperature of 50-80 °C.

The compound of formula 9 can be prepared by reacting the nitrile compound of formula 8 with hydroxylamine in polar protic solvents such as ethanol, methanol, etc. Alternatively, this reaction can also be carried out using hydroxylamine hydrochloride in the presence of organic and inorganic bases such as triethylamine, diisopropylamine, sodium bicarbonate, etc.

The compound of formula 10 can be prepared by reacting the compound of formula 9 with a carboxylic acid anhydride of formula a. Alternatively, the compound of formula 10 can also be prepared by reacting with the carboxylic acid chloride of formula b. Such reactions are typically carried out in aprotic solvents such as tetrahydrofuran, 1,4-dioxane, dichloromethane, etc., optionally in the presence of bases such as triethylamine, diisopropylamine, etc., at 0-50 °C.

The compound of formula 6 can be prepared by reacting the compound of formula 10 with a halogenating reagent such as N-bromosuccinimide in the presence of water. This reaction is typically carried out in solvents such as tetrahydrofuran at 0-25 °C.

Scheme 3

where L ¹ represents a direct link; A is aryl or pyridyl; L ² represents a direct connection; X represents Br, Cl or I and W ¹ represents O; R ¹ , R ^2f , R ^3f , R ¹⁰ and Q have the same meanings as defined in the detailed description above.

The compound of formula 12 can be prepared by reacting the nitrile compound of formula 11 with hydroxylamine in polar protic solvents such as ethanol, methanol, etc. Alternatively, this reaction can also be carried out using hydroxylamine hydrochloride in the presence of organic and inorganic bases such as triethylamine, diisopropylamine, sodium bicarbonate, etc.

The compound of formula 13 can be prepared by reacting the compound of formula 12 with a carboxylic acid anhydride of formula a. Alternatively, the compound of formula 13 can also be prepared by reacting with the carboxylic acid chloride of formula b. Such reactions are typically carried out in aprotic solvents such as tetrahydrofuran, 1,4-dioxane, dichloromethane, etc., optionally in the presence of bases such as triethylamine, diisopropylamine, etc., at 0-50 °C.

The compound of formula 14 can be prepared by reacting the compound of formula 13 with a suitable oxidizing agent such as m -chloroperoxybenzoic acid. This reaction is typically carried out in solvents such as dichloromethane at 0-30 °C.

The diol compound of formula 15 can be prepared by reacting the compound of formula 14 with a suitable hydrolyzing agent, such as water, in the presence of cerium ammonium nitrate at 10-30 °C.

The compound of formula 16 can be prepared by reacting the compound of formula 15 with a suitable oxidizing agent, such as oxon, in the presence of sodium bromide and water. This reaction is typically carried out in solvents such as acetonitrile at 0-25 °C.

The compound of formula (I) can be prepared by reacting a compound of formula 16 with a compound of formula R ¹⁰ -QH through Mitsunobu reaction conditions. This reaction is generally carried out in the presence of triphenylphosphine, diisopropyl azodicarboxylate or diethyl azodicarboxylate in solvents such as tetrahydrofuran, dichloromethane, etc.

In one embodiment, the present invention provides a compound of formula (B),

Formula (B),

Where

R ^1ia selected from ; And .

In another embodiment, the present invention provides a compound of formula (C),

Formula (C),

where G is selected from the group consisting of And ;

R ^2ia is selected from the group consisting of CH ₂ and O;

R ^2ib is selected from the group consisting of methyl and halogen.

In another embodiment, the present invention relates to a composition containing a compound of formula (I), agriculturally acceptable salts, metal complexes, constitutional isomers, stereoisomers, diastereoisomers, enantiomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers , polymorphs, geometric isomers or N-oxides thereof, optionally with one or more additional active ingredients with an excipient such as an inert carrier or any other main ingredient such as surfactants, additives, solid diluents and liquid diluents.

the compound of formula (I) and the composition of the present invention are respectively suitable as fungicides. They are characterized by exceptionally good effectiveness against a wide range of phytopathogenic fungi, including soil-borne fungi, which originate especially from the classes Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Some are systemically effective and can be used to protect crop plants as foliar fungicides, seed dressing fungicides and soil fungicides. Moreover, they are suitable for the control of harmful fungi that, among other things, occur in wood or plant roots.

the compound of formula (I) and the composition of the present invention are particularly useful for the control of a number of phytopathogenic fungi on various cultivated plants, such as cereals, for example wheat, rye, barley, triticale, oats or rice; beets, such as sugar beets or fodder beets; fruits and fruit trees such as apples, stone fruits or berries, such as apples, pears, plums, peaches, almonds, berries, strawberries, raspberries, blueberries or gooseberries, pulses such as beans, peas, alfalfa or soybeans; oil plants such as rapeseed, mustard, olives, sunflowers, coconut, cocoa beans, castor plants, oil palms, groundnuts or soybeans; cucurbits, such as pumpkins, cucumbers or melons; fibrous plants such as cotton, flax, hemp or jute, citrus fruits and citrus plants such as oranges, lemons, grapefruits or tangerines; any garden plants, vegetables such as spinach, lettuce, asparagus, types of cabbage, carrots, onions, tomatoes, potatoes, pumpkin or paprika; bay plants such as avocado, cinnamon or camphor; pumpkin; oil plants; plants used for energy and raw materials, such as cereals, corn, soybeans, other pulses, canola, sugar cane or oil palm; tobacco; nuts; coffee; tea; cocoa; bananas; peppers; grapes (table grapes and grapes for grape juice production); hop; turf; "sweet leaf" (also called stevia); natural rubber plants or ornamental and forest plants such as flowers, bushes, deciduous or evergreen trees such as conifers; and plant propagation materials, such as seeds, and the harvest of these plants. In particular, the compound of formula I and the composition in accordance with the present invention are important for the control of phytopathogenic fungi on soybean and on plant propagation material such as seeds and plant matter of soybean. Accordingly, the present invention also includes a composition containing at least one compound of formula I and a seed. The amount of compound of formula I in the composition is in the range of 0.1 g a. And. (grams per active ingredient) up to 10 kg a. And. (kilogram per active ingredient) per 100 kg of seeds.

Preferably, the compound of formula (I) and its composition are respectively used for the control of a number of fungi on field crops such as potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, beans, sunflowers , coffee or sugar cane; fruits; grapevines; ornamental plants; or vegetables such as cucumbers, tomatoes, beans or pumpkins.

The term "plant propagation material" should be understood to mean all the generative or reproductive parts of a plant, such as seeds and vegetative plant material, such as shoots and tubers (eg potatoes), that can be used to propagate the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts, branches, flowers and other parts of plants, including seedlings and young plants to be transplanted after germination or growth above the soil.

These young plants can also be protected until transplanting by full or partial treatment by dipping or watering.

Preferably, treatment of plant propagation material with a compound of formula I, a combination thereof and/or a composition thereof is respectively used to control a number of fungi on cereals such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.

The term "cultivated plants" should be understood to include plants that have been modified by crossing, mutagenesis or genetic engineering, including without limitation agricultural biotech products available on the market or under development (cf. http://cera-gmc. org/, see the database of genetically modified plants at this link). Genetically modified plants are plants whose genetic material has been modified through the use of recombinant DNA technology in such a way that it would not be readily produced under natural conditions by cross-breeding, mutation or natural recombination. Typically, one or more genes are integrated into the genetic material of a genetically modified plant to improve certain qualities of the plant. Such genetic modifications also include, but are not limited to, targeted post-translational modification of the protein(s), oligo- or polypeptides, for example by glycosylation or the addition of polymers such as prenylated, acetylated or farnesylated moieties or PEG moieties. Plants that have been modified by crossing, mutagenesis, or genetic engineering, for example, are designed to be resistant to the application of certain classes of herbicides, such as auxin-based herbicides such as dicamba or 2,4-D; decolorizing herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) or phytoene desaturase (PDS) inhibitors, acetolactate synthase (ALS) inhibitors such as sulfonylureas or imidazolinones; enolpyruvyl shikimate 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-based herbicides (i.e., bromoxynil or ioxynil) as a result of standard crossbreeding or genetic engineering techniques. In addition, plants have been engineered to be resistant to multiple classes of herbicides through several genetic modifications, such as resistance to both glyphosate and glufosinate, or both glyphosate and another class of herbicide such as ALS inhibitors, HPPD inhibitors, herbicides auxin-based or ACCase inhibitors. These herbicide resistance technologies are described, for example, 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, 1 185; and the links included therein. Several cultivated plants have been created to be resistant to herbicides through standard crossbreeding techniques (mutagenesis), for example Clearfield ^® , summer rape (Canola, BASF SE, Germany), which are resistant to imidazolines such as imazamox, or ExpressSun ^® sunflower (DuPont, USA), which is resistant to sulfonylurea compounds, such as tribenuron. Genetic engineering techniques have been used to create cultivated plants, such as soybeans, cotton, corn, beets and canola, that are resistant to herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady ^® (glyphosate resistant, Monsanto , USA), Cultivance ^® (imidazoline resistant, BASF SE, Germany) and LibertyLink ^® (glufosinate resistant, Bayer CropScience, Germany).

Also included are plants which, through the use of recombinant DNA technology, are capable of synthesizing one or more insecticidal proteins, especially proteins known from the genus Bacillus bacteria, in particular Bacillus thuringiensis, such as δ-endotoxins, for example CrylA(b), CrylA( c), CrylF, CrylF(a2), CryllA(b), CryllA, CryllB(bl) or Cry9c; vegetative insecticidal proteins (VIPs), for example VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from bacteria that colonize nematodes, such as Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins or other insect-specific neurotoxins; toxins produced by fungi such as Streptomycetes toxins, plant lectins such as pea or barley lectins; agglutinins; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIPs), such as ricin, corn ribosome-inactivating proteins, abrin, luffin, saporin or bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid IDP glycosyl transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA reductase; ion channel blockers such as sodium or calcium channel blockers; 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 should be understood explicitly as well as pre-toxins, fusion proteins, processed or otherwise modified proteins. Fusion proteins are characterized by a new combination of protein domains (see, for example, WO 02/015701). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, for example, in EP 374753, WO 93/007278, WO 95/34656, EP 427529, EP 451878, WO 03/18810 and WO 03/52073. Methods for producing such genetically modified plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. These insecticidal proteins contained in genetically modified plants give the plants producing these proteins resistance to harmful pests from all taxonomic groups of arthropods, especially beetles (Coeloptera), dipterans (Diptera), lepidoptera (Lepidoptera) and nematodes (Nematoda). Genetically modified plants capable of synthesizing one or more insecticidal proteins, for example, are described in the publications mentioned above, and some of them are commercially available, such as YieldGard ^® (maize species producing CrylAb toxin), YieldGard ^® Plus (maize species producing CrylAb and Cry3Bb1 toxins), Starlink ^® (corn species producing the Cry9c toxin), Herculex ^® RW (corn species producing Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN ^® 33B (cotton species producing CrylAc toxin), Bollgard ^® I (cotton species producing Cry1 Ac toxin), Bollgard ^® II (cotton species producing CrylAc and Cry2Ab2 toxins); VIPCOT ^® (VIP toxin-producing cotton species); NewLeaf ^® (potato species producing Cry3A toxin); Bt-Xtra ^® , Naturegard ^® , KnockOut ^® , Bitegard ^® , Protecta ^® , Bt1 1 (e.g. Agrisure ^® CB) and Bt176 from Syngenta Seeds SAS, France (maize species producing CrylAb toxin and PAT enzyme), MIR604 from Syngenta Seeds SAS, France (maize species producing a modified version of the Cry3A toxin, cf. WO 03/018810), MON 863 from Monsanto Europe SA, Belgium (maize species producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe SA, Belgium (cotton species, producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (maize species producing the Cry1 F toxin and PAT enzyme).

Also included are plants that, through the use of recombinant DNA technology, are capable of synthesizing one or more proteins to increase the resistance or resistance of those plants to bacterial pathogens, viral pathogens, or fungal pathogens. Examples of such proteins are the so-called “pathogenesis-related proteins” (PR proteins, see for example EP 392225), plant disease resistance genes (for example, potato species that express resistance genes to Phytophthora infestans obtained from wild Mexican potatoes Solanum bulbocastanum) or T4 lysozyme (for example, potato species capable of synthesizing these proteins with increased resistance to bacteria such as Erwinia amylvora). Methods for producing such genetically modified plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above.

Also included are plants that, through the use of recombinant DNA technology, are capable of synthesizing one or more proteins to increase productivity (e.g., biomass production, grain yield, starch content, oil content, or protein content), tolerance to drought, salinity, or other limiting growth of environmental factors or resistance to pests and pathogens - fungi, pathogens - bacteria or pathogens - viruses of these plants.

In addition, also included are plants which, as a result of the use of recombinant DNA technology, contain changed amounts of substances in the composition or new substances in the composition, in particular for improving human or animal nutrition, for example oilseeds that produce health-promoting omega-3 fatty acids with long chain or unsaturated omega-9 fatty acids (eg Nexera ^® canola, DOW Agro Sciences, Canada).

In addition, also included are plants which, as a result of the use of recombinant DNA technology, contain changed amounts of substances in the composition or new substances in the composition, in particular to improve the production of raw material, for example potatoes that produce increased amounts of amylopectin (for example, Amflora ^® BASF SE potatoes , Germany).

The present invention also relates to a method for controlling or preventing plant pathogenic microorganisms in crops and/or horticultural crops, wherein an effective amount of at least one compound of formula I or a combination of the present invention or a composition of the present invention is applied to the seeds of the plants. The compound, combination and composition of the present invention can be used to control or prevent plant diseases. a compound of formula I, a combination and/or composition thereof, respectively, is particularly suitable for the control of the following plant diseases:

Albugo spp. (white rust) on ornamental plants, vegetables (eg A. candida ) and sunflower plants (eg A. tragopogonis ); Altemaria spp. (alternaria blight) on vegetables, rapeseed ( A. brassicola or brassicae ), sugar beet plants ( A. tenuis ), fruits, rice, soybeans, potato plants (e.g. A. solani or A. alternata ), tomato plants (e.g. A. . solani or A. alternata ) and wheat; Aphanomyces spp. on sugar beet plants and vegetables; Ascochyta spp. on cereals and vegetables, for example A. tritici (anthracnose) on wheat and A. hordei on barley; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e.g. southern leaf spot ( D. maydis ) or northern leaf spot ( B. zeicola ) on corn, e.g. helminthosporium root rot ( B. sorokiniana ) on cereals and e.g. B. oryzae on rice and types of turf; Blumeria (formerly Erysiphe ) graminis (powdery mildew) on cereals (such as wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: gray mold) on fruits and berries (eg strawberry plants), vegetables (eg lettuce, carrot plants, celery and cabbage plants), rapeseed, flowers, vines, forest plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (synonym Ophiostoma ) spp. (rot or wilt) on deciduous trees and evergreens, e.g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (cercospora leaf spot) on corn (eg gray leaf spot: C. zeae-maydis ), rice, sugar beet plants (eg C. beticola ), sugar cane, vegetables, coffee, soybean (eg C. sojina or C . kikuchii ) and rice; Cladosporium spp. on tomato plants (eg C. fulvum : leaf mold) and cereals, eg C. herbarum (black spot) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph: Helminthosporium genus Bipolaris) spp. (leaf spot) 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 stem rot), berries, potato plants (e.g. C. coccodes : black spot rot), beans (e.g. C. lindemuthianum ) and soybean (for example, C. truncatum or C. gloeosporioides ); Corticium spp., eg C. sasakii (shell disease) on rice; Corynespora cassiicola (leaf spot) on soybean and ornamental plants; Cycloconium spp., eg C. oleaginum on olive trees; Cylindrocarpon spp. (eg fruit tree canker or wilt of young grape vines, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (eg C. liriodendri, teleomorph: Neonectria liriodendri : blackleg) and ornamental plants; Dematophora (teleomorph: Rosellinia ) necatrix (root and stem rot) on soybean; Diaporthe spp., e.g. D. phaseolorum (soaking) on soybean; Drechslera (synonym Helminthosporium, teleomorph: Pyrenophora ) spp. on corn, cereals such as barley (eg D. teres , net blight) and wheat (eg D. tritici-repentis : pyrenophorosis), rice and turf; Esca (dying back) on grapevines caused by Formitiporia (syn. Phellinus) punctata , F. mediterranea, Phaeomoniella chlamydospora (formerly Phaeoacremonium chlamydosporum ), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa ; Elsinoe spp. on pome fruits ( E. pyri ), berries (A. veneta: anthracnose ) and vines (E. ampelina: anthracnose ); Entyloma oryzae (cereal smut) on rice; Epicoccum spp. (black rot) on wheat; Erysiphe spp. (powdery mildew) on sugar beet plants (E. betae), vegetables (for example, E. pisi ), such as cucurbits (for example, E. cichoracearum ), cabbage plants, rapeseed (for example, E. cruciferarum ); Eutypa lata ( Eutypa canker or dieback, anamorph: Cytosporina lata , synonym of Libertella blepharis ) on fruit trees, vines and ornamental trees; Exserohilum (synonym Helminthosporium ) spp. on corn (for example, 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 fusarium) on cereals (e.g. wheat or barley), F. oxysporum on tomato, F. solani (f . sp. glycines, now a synonym of F. virguliforme ) and F. tucumaniae and F. brasiliense , each of which causes sudden death syndrome in soybeans, and F. verticillioides in corn; Gaeumannomyces graminis (damping off) on cereals (eg wheat or barley) and corn; Gibberella spp. on cereals (eg G. zeae ) and rice (eg G. fujikuroi : rice gibberellosis); Glomerella cingulata on grapevines, pome fruits and other plants and G. gossypii on cotton; grain coloring complex for rice; Guignardia bidwellii (black rot) on grapevines; Gymnosporangium spp. on rose plants and junipers, for example G. sabinae (rust) on pears; Helminthosporium spp. (synonym Drechslera , teleomorph: Cochliobolus ) on corn, cereals and rice; Hemileia spp., e.g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (synonym Cladosporium vitis ) on grapevines; Macrophomina phaseolina (syn. phaseoli ) (root and stem rot) on soybean and cotton; Microdochium (synonym Fusarium ) nivale (pink snow mold) on cereals (such as wheat or barley); Microsphaera diffusa (powdery mildew) on soybean; Monilinia spp., eg M. laxa, M. fructicola and M. fructigena (bud or branch dieback, brown rot) on stone fruits and other rose-shaped plants; Mycosphaerella spp. on cereals, bananas, berries and groundnuts, such as for example M. graminicola (anamorph: Septoria tritici, Septoria blotch ) on wheat or M. fijiensis (black sigatoka disease) on bananas; Peronospora spp. (powdery mildew) on cabbage (e.g. P. brassicae ), rapeseed (e.g. P. parasitica ), onion plants (e.g. P. destructor ), tobacco ( P. tabacina ) and soybean (e.g. P. manshurica ); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybean; Phialophora spp., e.g. on grapevines (e.g. P. tracheiphila and P. tetraspora ) and soybean (e.g. P. gregata : stem rot); Phoma lingam (root and stem rot) on rapeseed and cabbage and P. betae (root rot, leaf spot and damping off) on sugar beet plants; Phomopsis spp. on sunflower plants, grapevines (e.g. P. viticola : Phomopsis) and soybeans (e.g. stem rot: P. phaseoli , teleomorph: Diaporthe phaseolorum ); Physoderma maydis (brown spot) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem rot) on various plants such as capsicum and cucurbits (e.g. P. capsici ), soybeans (e.g. P. megasperma , synonym P. sojae ), soybean, potato and tomato plants (eg P. infestans : late rot) and deciduous trees (eg P. ramorum : sudden oak death); Plasmodiophora brassicae (clubroot) on cabbage, rapeseed, radish and other plants; Plasmopara spp., such as P. viticola (grapevine powdery mildew) on grapevines and P. halstedii on sunflower plants; Podosphaera spp. (powdery mildew) on rose plants, hops, pome fruits and berries, for example P. leucotricha on apples; Polymyxa spp., for example, on cereals such as barley and wheat ( P. graminis ) and sugar beet plants ( P. betae ) and the viral diseases they carry; Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapesia yallundae ) on cereals, for example; wheat or barley Pseudoperonospora (powdery mildew) on various plants, for example P. cubensis on cucurbits or P. humili on hops; Pseudopezicula tracheiphila (grape leaf rubella or Rotbrenner, anamorph: Phialophora) on grapevines; Puccinia spp. (rust species) on various plants, such as P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem rust or black rust) or P . recondita (brown or leaf rust) on cereals such as wheat, barley or rye, P. kuehnii (orange rust) on sugarcane and P. asparagi on asparagus; Pyrenophora (anamorph: Drechslera ) tritici-repentis (pyrenophora) on wheat or P. teres (net spot) on barley; Pyricularia spp., e.g. P. oryzae (teleomorph: Magnaporthe grisea , rice fungus) on rice and P. grisea on turf and grasses; Pythium spp. (soaking) on turf, rice, corn, wheat, cotton, canola, sunflower plants, soybeans, sugar beet plants, vegetables and various other plants (such as P. ultimum or P. aphanidermatum ); Ramularia spp., for example R. collocygni (ramularia leaf spot, physiological leaf spot) on barley and R. beticola on sugar beet plants; Rhizoctonia spp. on cotton, rice, tomatoes, turf, corn, canola, potato plants, sugar beet plants, vegetables and various other plants, e.g. R. solani (root and stem rot) on soybeans, R. solani (hull disease) on rice or R. cerealis (rhizoctonia blight) on wheat or barley; Rhizopus stolonifer (black rot, soft rot) on strawberry, carrot, cabbage, grapevine and tomato plants; Rhynchosporium secalis (rhynchosporium blight) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (hull rot) on rice; Sclerotinia spp. (stem rot or white rot) on vegetables and field crops such as canola, sunflower plants (e.g. S. sclerotiorum ) and soybeans (e.g. S. rolfsii or S. sclerotiorum ); Septoria spp. on various plants, for example S. glycines (brown spot) on soybeans, S. tritici (septoria) on wheat and S. (syn. Stagonospora ) nodorum ( stagonospora ) on cereals; Uncinula (syn. Erysiphe ) necator (powdery mildew, anamorph: Oidium tuckeri ) on grapevines; Setospaeria spp. (leaf spot) on corn (e.g. S. turcicum , synonym Helminthosporium turcicum ) and turf; Sphacelotheca spp. (smut) on corn, (eg S. reiliana : smut), sorghum and sugarcane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potato plants and viral diseases transmitted by them; Stagonospora spp. on cereals, e.g. S. nodorum ( stagonospora , teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potato plants (potato canker); Taphrina spp., eg T. deformans (leaf curl) on peaches and T. pruni (fruit pockets) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e.g. T. basicola (syn. Chalara elegans); Tilletia spp. (wheat smut or wheat smut) on cereals, such as, for example, T. tritici (synonym T. caries, wheat smut) and T. controversa (dwarf smut) on wheat; Typhula incarnata (gray 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 , synonym of U. phaseoli ) and sugar beet plants (e.g. U. betae ); Ustilago spp. (head smut) on cereals (eg U. nuda and U. avaenae ), corn (eg U. maydis : corn smut) and sugarcane; Venturia spp. (scab) on apples (eg V. inaequalis ) and pears; and Verticillium spp. (wilt) on various plants such as fruits and ornamental plants, vines, berries, vegetables and field crops, for example V. dahliae on strawberry plants, rapeseed, potato and tomato plants.

a compound of formula I, combination or composition thereof can be used for treatment against several fungal pathogens. Non-limiting examples of fungal pathogens that can be treated in accordance with the present invention include:

Ustilaginales such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae , rust species such as those caused by Pucciniales such as Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, Puccinia graminis, uccinia 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 types of rot 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, ephorus 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, such as Gymnosporangium species, such as Gymnosporangium sabinae ; Hemileia species, such as Hemileia vastatrix ; Phakopsora species, such as Phakopsora pachyrhizi or Phakopsora meibomiae ; Puccinia species, such as Puccinia recondita , Puccinia graminis or Puccinia striiformis ; Uromyces species, such as 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 rye); Puccinia graminis (stem rust of wheat and bluegrass, or black rust of cereals); Puccinia hemerocallidis (daylily rust); Puccinia persistens subsp. triticina (wheat rust or "brown or red rust"); Puccinia sorghi (corn rust); Puccinia striiformis (“yellow rust” of cereals); Uromyces appendiculatus (bean rust); Uromyces phaseoli (bean rust); Puccinia melanocephala (sugarcane brown rust); Puccinia kuehnii (“yellow rust” of sugar cane).

Plants that can be treated according to the present 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. (e.g. banana trees and plantations), Rubiaceae sp. (e.g. coffee), Theaceae sp. , Sterculiceae sp. , Rutaceae sp. (eg lemons, oranges and grapefruits); Vitaceae sp. (for example, grapes); Solanaceae sp. (e.g. tomatoes, peppers), Liliaceae sp. , Asteraceae sp. (e.g. lettuce), Umbelliferae sp. , Cruciferae sp. , Chenopodiaceae sp. , Cucurbitaceae sp. (e.g. cucumber), Alliaceae sp. (e.g. leeks, onions), Papilionaceae sp. (for example, peas); major crop plants such as Poaceae / Gramineae sp. (e.g. corn, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (eg sunflower), Brassicaceae sp. (e.g. white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choy, kohlrabi, radish, mustard, horse radish and watercress), Fabacae sp. (e.g. beans, peanuts), Papilionaceae sp. (e.g. soybeans), Solanaceae sp. (e.g. potatoes), Chenopodiaceae sp. (e.g. sugar beet, fodder beet, leaf beet, table beet); Malvaceae (eg cotton); useful plants and ornamental plants for gardens and woodlands; and genetically modified variations of each of these plants.

More emphasis is placed on controlling the following soybean diseases. Fungal diseases on leaves, shoots, pods and seeds caused by, for example, Alternaria leaf spot ( Altemaria spec. atrans tenuissima ), anthracnose ( Colletotrichum gloeosporoides dematium var. truncatum ), brown spot ( Septoria glycines ), cercospora leaf spot and plant diseases ( Cercospora kikuchii ), leaf diseases caused by the genus Choanephora ( Choanephora infundibulifera trispora (syn.) ), selenophoma leaf spot ( Dactuliophora glycini ), powdery mildew ( Peronospora manshurica ), diseases caused by the genus Drechslera ( Drechslera glycini ), round leaf spot ( Cercospora sojina ), leaf spot caused by the genus Leptosphaerulina trifolii , leaf spot caused by the genus Phyllosticta sojaecola , pod and stem disease ( Phomopsis sojae ), powdery mildew ( Microsphaera diffusa ), leaf spot caused by the genus Pyrenochaeta glycines , a disease of above-ground parts, foliage and roots caused by the genus Rhizoctonia solani , rust ( Phakopsora pachyrhizi , Phakopsora meibomiae ), scab ( Sphaceloma glycines ), a leaf disease caused by the genus Stemphylium botryosum , target spot ( Corynespora cassiicola ).

Fungal diseases on the roots and base of the stem, caused by, for example, black root rot ( Calonectiia crotalariae ), charcoal rot ( Macrohomina phaseolina ), wilt or Fusarium disease, root rot and pod and branch rot ( Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti ), root rot caused by the genus Mycoleptodiscus terrestri , neocosmospora ( Neocosmospora vasinfecta ), pod and stem disease ( Diaporthe phaseolorum ), stem canker ( Diaporthe phaseolorum var. caulivora ), blight caused by late blight ( Phytophthora megas perma ) , brown stem rot ( Phialophora gregata ), rot caused by the genus Pythium ( Pythium aphanidennatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum ), root rot caused by the genus Rhizoctonia, stem destruction and soaking ( Rhizoctonia solani ), destruction stem, caused by Sclerotinia sclerotiorum , southern sclerotinia rot ( Sclerotinia rolfsii ), stem rot caused by Thielaviopsis basicola .

The present invention also relates to the use of a compound of formula I, combination or composition thereof for the control or prevention of the following plant diseases: Puccinia spp. (rust species) on various plants, such as, 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, for example, wheat, barley or rye and Phakopsoraceae spp . on various plants, notably Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybean, Hemileia vastatrix (coffee rust), Uromyces appendiculatus , Uromyces fabae and Uromyces phaseoli (bean rust).

The present invention further relates to the use of a compound of formula I, a combination or composition thereof, for the control and prevention of phytopathogenic fungi, such as Phakopsora pachyrhizi, Phakopsora meibomiae , in agricultural crops and/or horticultural crops.

the compound of formula I, its combination and composition, respectively, are also suitable for the control of harmful fungi, the protection of stored products or crops and the protection of materials. The term "material protection" should be understood to mean the protection of technical and non-living materials, such as adhesives, types of adhesives, wood, paper and cardboard, types of textiles, leather, paint dispersions, types of plastics, cutting fluids, fibers or fabrics, from infection and destruction by harmful microorganisms such as fungi and bacteria.

Regarding the protection of wood and other materials, special 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., Poria 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, protection of stored products and crops from the following yeasts is noteworthy: Candida spp. and Saccharomyces cerevisae.

In one embodiment, the compound of formula I, combination and composition thereof are, respectively, particularly suitable for the control of the following plant diseases: Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybean.

The present invention further relates to a method for controlling or preventing the occurrence of phytopathogenic fungi. The method involves treating fungi or materials, plants, parts of plants, their growing location, soil or seeds to be protected from fungal attack with an effective amount of at least one compound of formula I or a combination thereof or a composition containing at least one compound of formula I.

The treatment method according to the present invention can also be used in the field of protecting stored products or crops from damage by fungi and microorganisms. For the purpose of the present invention, the term "stored products" is understood to mean natural substances of plant or animal origin and their processed forms that have been removed from the natural life cycle and for which long-term protection is required. Stored products originating from agricultural plants, such as plants or parts thereof, such as stems, leaves, tubers, seeds, fruits or grains, may be protected in freshly harvested or processed forms, such as pre-dried, moistened, crushed, ground, pressed or roasted, this method is also known as post-harvest processing. Also included within the definition of stored products is timber, whether it is in the form of unprocessed timber, such as structural timber, power poles and barriers, or in the form of finished products, such as furniture or items made from wood. Stored animal products are hides, skins, furs, wool, etc. The combination of the present invention can prevent undesirable effects such as decay, loss of color or mold. Preferably, the term "stored products" is understood to mean natural plant substances and processed forms thereof, more preferably fruits and processed forms thereof, such as apple fruits, stone fruits, berries and citrus fruits and processed forms thereof.

a compound of formula I, its combination and composition, respectively, can be used to improve the condition of the plant. The compound also relates to a method of improving the condition of a plant by treating the plant, its propagation material and/or the site where the plant is or will be planted with an effective amount of Compound I and a composition thereof, respectively.

The term "plant viability" should be understood as a designation of the state of the plant and/or its products, which is determined by several indicators individually or in combination with each other, such as yield (for example, increased biomass and/or increased content of valuable ingredients), vigor plants (eg improved plant growth and/or greener leaves (“greening effect”)), quality (eg improved content or composition of certain ingredients) and resistance to abiotic and/or biotic stress. The above indicators of the state of plant viability can be interdependent or arise from each other.

The compound of formula I may be present in the form of different crystal modifications or polymorphs, the biological activity of which may vary. They are also an object of the present invention.

The compound of formula I is used in this form or in the form of a composition for the treatment of fungi or plants, plant propagation materials such as seeds, soil, surfaces, materials or premises to be protected from fungal attack by a fungicidal effective amount of the active ingredients. Application can be carried out both before and after fungal infestation of plants, plant propagation materials such as seeds, soil, surfaces, materials or spaces.

Plant propagation materials may be treated with a compound of formula I, combination and composition thereof for protection purposes either at or after planting or replanting.

The present invention also relates to an agrochemical composition containing an auxiliary substance and at least one compound of formula I.

The agrochemical composition contains a fungicidal effective amount of a compound of Formula I. The term "effective amount" means an amount of a composition or compound of Formula I that is sufficient to control harmful fungi on crop plants or protect materials and that does not cause significant damage to the plants being treated. Such amount may vary widely and depends on various factors such as the species of fungi to be controlled, the plant or material being cultivated, the climatic conditions and the particular compound of formula I that is used.

The compounds of formula I, their N-oxides, metal complexes, isomers, polymorphs or agriculturally acceptable salts can be converted into conventional types of agrochemical compositions, for example, solutions, emulsions, suspensions, sprays, powders, pastes, granules, extracts, capsules and their mixtures. Examples of 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, lozenges, wettables powders or powder (e.g. WP, SP, WS, DP, DS), compressed forms (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal products (e.g. , LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (eg GF). These and additional composition types are defined in the "Catalog 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 those described in 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 excipients are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, auxiliaries, solubilizers, penetration aids, protective colloids, adhesive additives, thickeners, humectants, water repellents , attractants, eating stimulants, compatibility agents, bactericidal agents, antifreeze agents, defoamers, dyes, tackifiers and binders.

Suitable solvents and liquid carriers include water and organic solvents such as medium to high boiling point mineral oil fractions, eg kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, for example, toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, eg ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, such as cyclohexanone; esters, for example lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acid; phosphonates; amines; amides, for example N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof. Suitable solid carriers or fillers are mineral substances, for example silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, for example cellulose, starch; fertilizers, for example ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; products of plant origin, for example, cereal flour, tree bark flour, wood flour, nut shell flour, and mixtures thereof.

Suitable surfactants are surfactants such as anionic, cationic, nonionic and amphoteric surfactants, block copolymers, polyelectrolytes and mixtures thereof. Such surfactants may be used as an emulsifier, dispersant, solubilizer, wetting agent, penetration aid, 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 alkaline, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, fatty acid and oil sulfonates, ethoxylated alkyl phenols sulfonates, alkoxylated aryl phenols sulfonates, condensed naphthalene sulfonates, dodecyl and tridecyl benzene sulfonates, naphthalene and alkyl naphthalene sulfonates, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols or fatty acid esters. Examples of phosphates are esters of phosphoric acid. Examples of carboxylates are alkyl carboxylates and carboxylated alcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants include 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 that have been alkoxylated using 1-50 equivalents. For alkoxylation, ethylene oxide and/or propylene oxide can be used, 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-glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, 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 alkyl betaines and imidazolines. Suitable block copolymers are A-B or A-B-A type block copolymers containing polyethylene oxide and polypropylene oxide blocks, or A-B-C type block copolymers containing an alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid graft comb copolymers. Examples of polybases are polyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds that themselves have negligible or no pesticidal activity and improve the biological performance of the compound of formula I on the target. Examples are surfactants, mineral or vegetable oils and other excipients. Further examples are listed in Knowles, Adjuvants and additives, Agrow Reports DS256, T&F lnforma UK, 2006, chapter 5.

Suitable thickeners include polysaccharides (eg xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates.

Suitable germicidal agents are derivatives of bronopol and isothiazolinone, such as alkyl isothiazolinones and benzisothiazolinones.

Suitable antifreeze agents include ethylene glycol, propylene glycol, urea and glycerin.

Suitable defoamers include silicones, long chain alcohols and fatty acid salts.

Suitable colorants (eg red, blue or green) are pigments having low water solubility and water-soluble dyes. Examples are inorganic colorants (eg, iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (eg, alizarin-, azo-, and phthalocyanine-based dyes).

Suitable tackifiers or binders are polyvinylpyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes and cellulose ethers.

Examples of the types of compositions and their preparation are as follows.

i) Water-soluble concentrates (SL, LS)

10-60 wt. % compound of formula I and 5-15 wt. % of the wetting agent (eg, alcohol alkoxylates) is dissolved in water and/or water-soluble solvent (eg, alcohols) at 100 wt. %. The active substance dissolves when diluted with water.

ii) Dispersible concentrates (DC)

5-25 wt.% of a compound of formula I and 1-10 wt. % dispersant (for example, polyvinylpyrrolidone) is dissolved in an organic solvent (for example, cyclohexanone) at 100 wt. %. Dilution with water provides dispersion.

iii) Emulsifiable concentrates (EC)

15-70 wt. % compound of formula I and 5-10 wt. % emulsifiers (for example, calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (for example, an aromatic hydrocarbon) at 100 wt. %. Dilution with water provides an emulsion.

iv) Emulsions (EW, EO, ES)

5-40 wt. % compound of formula I and 1-10 wt. % emulsifiers (for example, calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt. % water-insoluble organic solvent (for example, an aromatic hydrocarbon). This mixture is added to water up to 100 wt. % using an emulsifying device and turn into a homogeneous emulsion. Dilution with water provides an emulsion.

v) Suspensions (SC, OD, FS)

In a mixing ball mill 20-60 wt. % of the compound of formula I is crushed with the addition of 2-10 wt. % dispersants and wetting agents (for example, sodium lignosulfonate and alcohol ethoxylate), 0.1-2 wt. % thickener (for example, xanthan gum) and water at 100 wt. % to obtain a fine suspension of the active substance. Dilution with water ensures a stable suspension of the active substance. For composition type FS, add no more than 40 wt. % binder (for example, polyvinyl alcohol).

vi) Water dispersible granules and water soluble granules (WG, SG)

50-80 wt. % of the compound of formula I is finely ground with the addition of dispersing agents and wetting agents (for example, sodium lignosulfonate and alcohol ethoxylate) at 100 wt. % and obtain water-dispersible or water-soluble granules using technological devices (for example, using extrusion, irrigation scrubber, fluidized bed). Dilution with water provides a stable dispersion or solution of the active substance. vii) Water dispersible and water soluble powders (WP, SP, WS) 50-80 wt. % of the compound of formula I is ground in a rotary mill with the addition of 1-5 wt. % dispersing agents (for example, sodium lignosulfonate), 1-3 wt. % wetting agents (eg alcohol ethoxylate) and solid carriers (eg silica gel) at 100 wt. %. Dilution with water provides a stable dispersion or solution of the active substance.

viii) Gel (GW, GF)

In a mixing ball mill 5-25 wt. % of the compound of formula I is crushed with the addition of 3-10 wt. % dispersing agents (for example, sodium lignosulfonate), 1-5 wt. % thickener (for example, carboxymethylcellulose) and water at 100 wt. % to obtain a fine suspension of the active substance. Dilution with water ensures a stable suspension of the active substance.

ix) Microemulsion (ME)

5-20 wt. % of the compound of formula I is added to 5-30 wt. % mixture of organic solvents (for example, fatty acid dimethylamide and cyclohexanone), 10-25 wt. % mixture of surfactants (eg alcohol ethoxylate and arylphenol ethoxylate) and water at 100%. This mixture is stirred for 1 hour to spontaneously obtain a thermodynamically stable microemulsion.

x) Microcapsules (CS)

Fat phase containing 5-50 wt. % compound of formula I, 0-40 wt. % water insoluble organic solvent

(for example, aromatic hydrocarbon), 2-15 wt. % acrylic monomers (eg methyl methacrylate, methacrylic acid and di- or triacrylate) are dispersed in an aqueous solution of a protective colloid (eg polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate microcapsules. Alternatively, a fat phase containing 5-50 wt. % of the compound of formula I of the present invention, 0-40 wt. % water-insoluble organic solvent (eg, an aromatic hydrocarbon) and an isocyanate monomer (eg, diphenylmethylene-4,4'-diisocyanate) are dispersed in an aqueous solution of a protective colloid (eg, polyvinyl alcohol). The addition of a polyamine (eg hexamethylenediamine) results in the formation of polyurea microcapsules. The number of monomers is up to 1-10 wt. %. Weight. % refers to the entire CS composition.

xi) Dust-like powders (DP, DS)

1-10 wt. % of the compound of formula I is finely ground and thoroughly mixed with a solid carrier (for example, finely ground kaolin) at 100 wt. %.

xii) Granules (GR, FG)

0.5-30 wt. % of the compound of formula I is finely ground and bonded to a solid carrier (for example, silicate) at 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 is dissolved in an organic solvent (for example, an aromatic hydrocarbon) at 100 wt. %.

Compositions of types i) - xiii) may optionally contain additional excipients, for example, 0.1-1 wt. % bactericidal substances, 5-15 wt. % of substances that prevent freezing, 0.1-1 wt. % defoamers and 0.1-1 wt. % dyes.

Agrochemical compositions typically contain from 0.01 to 95%, preferably from 0.1 to 90% and in particular from 0.5 to 75% by weight of active ingredient (a.i.). Active ingredients (a.i.) are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

For the treatment of plant propagation materials, in particular seeds, seed treatment solutions (LS), suspoemulsions (SE), liquid concentrates (FS), dry treatment powders (DS), water-dispersible suspension treatment powders (WS) are commonly used. ), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF). The compositions under consideration, after dilution by two to ten times, give concentrations of the active substance from 0.01 to 60 wt. %, preferably from 0.1 to 40%, in ready-to-use preparations.

Application can be done before or during sowing. Methods for applying a compound of formula I, combinations thereof and compositions, respectively, to plant propagation material, especially seeds, include dressing, pelleting, granulating, spraying and soaking, as well as in-furrow methods. Preferably, the compound of formula I, the combination and composition thereof are respectively applied to the plant propagation material by a method that does not cause seed germination, for example, by dressing, granulating, pelleting and spraying.

When used for plant protection, the amount of active substances used, depending on the desired effect, is from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 1.0 kg per ha and, in particular, from 0.1 to 1.0 kg per hectare.

When treating plant propagation materials such as seeds, for example by spraying on the seeds, pelleting or soaking the seeds, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 1000 g are generally required. 100 g and most preferably from 5 to 100 g per 100 kg of plant propagation material (preferably seeds).

When used to protect materials or stored products, the amount of active substance applied depends on the type of application site and the desired effect. The amount typically used to protect materials is from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg of active substance per cubic meter of material treated.

Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients, as well as additional pesticides (for example, herbicides, insecticides, fungicides, growth regulators, antidotes, biopesticides) can be added to the active substances or compositions containing them in the form of an additive or, if necessary, only immediately before use (tank mix). These agents can be mixed with the compositions of the present 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 pesticide active ingredient, compound, composition, virus, bacterium, antimicrobial or disinfectant) that acts to repel, neutralize, kill or otherwise interfere with pests. Target pests may include insects, plant pathogens, weeds, shellfish, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease, or carry disease. The term "pesticide" also includes plant growth regulators that alter the expected rate of growth, flowering or reproduction of plants; defoliants, which cause the leaves or other covering of plants to fall off, usually to facilitate harvesting; desiccants, which help dry out living tissue such as unwanted plant tops; plant activators, which activate plant physiological processes to protect against certain pests; and plant growth stimulants that affect plant physiology, for example, to increase plant growth, biomass, yield or any other quality parameter of harvestable crop products.

The user typically applies the composition of the present invention from a pre-dosage device, backpack sprayer, spray tank, spray plane or irrigation system. Typically, the agrochemical composition is formulated with water, buffer and/or other excipients to the desired application concentration, thereby obtaining a ready-to-use spray solution or agrochemical composition of the present invention. Typically, 20 to 2000 liters, preferably 50 to 400 liters of ready-to-use spray liquid are applied per hectare of agricultural usable area.

In one embodiment, the individual components of the composition of the present invention, such as parts of a kit or parts of a two-part or three-part mixture, can be mixed by the user in a spray tank or in any other type of tank used for application (eg, seed treatment drums, equipment for seed granulation, backpack sprayer), and other auxiliaries can be added if necessary.

Therefore, in one embodiment of the present invention, a kit is provided for preparing a suitable pesticide composition, the kit comprising a) a composition comprising component 1) as defined herein, and at least one excipient; and b) a composition containing component 2) as defined herein, and at least one excipient; and optionally c) a composition containing at least one excipient and optionally an additional active component 3) as defined herein.

A compound of formula I, a combination thereof and a composition containing them, when used as fungicides with other fungicides, can lead to a broadening of the resulting fungicidal spectrum of activity or to the prevention of the development of fungicide resistance. In addition, in many cases unusual effects are achieved.

The present invention also relates to a combination containing at least one compound of formula I and at least one substance having additional activity as a pesticide selected from the group of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, antidotes, plant growth regulators, antibiotics , fertilizers and nutrients. The pesticide active substances described in WO 2015185485, pages 36-43 and WO 2017093019, pages 42-56 can be used in combination with a compound of formula (I).

The active substances called component 2, their preparation and their activity, for example, against harmful fungi are known (cf. http://www.alanwood.net/pesticides/); such substances are commercially available. The compounds are described using IUPAC nomenclature, and their preparation and their activity as pesticides are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP 141317; EP 152031; EP 226917; EP 243970; EP 256503; EP 532025; EP 1201648; JP2002316902; 09458; US3325503; WO 9924413; WO 0046148; WO 0065913; WO 0222583; WO 0310143; 0361388; WO 0374491; WO 0483193; WO 05123690; WO 0587773; WO 0687343; WO 2012168188; WO 201177514; WO 10069882; WO 0316303; WO 13007762; WO 13024009; WO 13047441; 4 and WO 11135833.

Furthermore, the present invention relates to an agrochemical mixture containing at least one compound of formula I (component 1) and at least one additional active substance useful for plant protection,

By applying a compound of formula I together with at least one active compound having pesticide activity, an additional effect can be achieved.

This can be achieved by co-applying a compound of formula I and at least one substance having additional activity as a pesticide, either simultaneously (for example, as a tank mixture), separately or sequentially, where the time interval between individual applications is so chosen to ensure that the first applied active substance is still present in sufficient quantity at the site of action during application of additional substance(s) having pesticide activity. The order of application is not important for the practice of the present invention.

When applying a compound of formula I and a substance having pesticide activity sequentially, the time between the two applications may vary, for example from 2 hours to 7 days. A wider range of 0.25 hours to 30 days, preferably 0.5 hours to 14 days, especially 1 hour to 7 days or 1.5 hours to 5 days, even more preferably 2 hours to 1 day is also possible . In the two-component mixtures and compositions according to the invention, the weight ratio of component 1) to component 2) usually depends on the properties of the active components used, usually in the range from 1:1000 to 1000:1, often in the range from 1:100 to 100:1, typically 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 from 1:2 to 2:1.

According to a further embodiment of binary mixtures and their composition, the weight ratio of component 1) to component 2) is typically in the range of 1000:1 to 1:1000, often in the range of 100:1 to 1:100, typically in the range of 50:1 to 1:50, preferably in the range from 20:1 to 1:20, more preferably in the range from 10:1 to 1:10, even more preferably in the range from 4:1 to 1:4 and, in particular, in the range from 2:1 to 1:2.

In three-component mixtures, that is, in the composition according to the invention containing component 1) and component 2) and compound III (component 3), the weight ratio of component 1) and component 2) depends on the properties of the active substances used, usually in the range from 1 :100 to 100:1, typically 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 from 1:4 to 4:1, and the weight ratio of component 1) to component 3) is usually in the range of 1:100 to 100:1, usually in the range of 1:50 to 50:1, preferably in the range of 1: 20 to 20:1, more preferably in the range from 1:10 to 10:1 and in particular in the range from 1:4 to 4:1.

If necessary, any other active components are added in a ratio of 20:1 to 1:20 to component 1).

Such ratios are also suitable for the mixtures of the present invention useful in seed treatment.

The present invention also relates to a method for producing the compound of the present invention. The method for preparing the compound of the present invention is described in the experimental section in more detail.

The present invention disclosed herein is now to be made clearer by means of non-limiting diagrams and examples.

CHEMICAL EXAMPLES

Example 1. Preparation of 2-(2-chloro-5-methylphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (compound no. 33)

a) Step 1. 4-(2-Methyl-1,3-dioxolan-2-yl)benzonitrile

Trimethyl orthoformate (50 mL, 0.9 mol) and N-bromosuccinimide (1.2 g, 7 mmol) were added to a stirred solution of 4-acetylbenzonitrile (10 g, 69 mmol) and ethylene glycol (80 ml, 1.4 mol). at 25°C. The resulting reaction mixture was stirred at 65°C for 12 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane (120 ml) and washed with water (80 ml). The dichloromethane layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 4-(2-methyl-1,3-dioxolan-2-yl)benzonitrile (12 g, 92% yield).

b) Step 2. N'-Hydroxy-4-(2-methyl-1,3-dioxolan-2-yl)benzimidamide

Sodium bicarbonate (9.6 g, 114 mmol) and hydroxylamine hydrochloride ( 5.3 g, 76 mmol) at 0°C. The resulting reaction mixture was stirred at 65°C for 4 hours. After completion of the reaction, the reaction mixture was filtered and concentrated under reduced pressure to obtain N'-hydroxy-4-(2-methyl-1,3-dioxolan-2-yl)benzimidamide (12 g, yield 85 %).

c) Step 3. 3-(4-(2-Methyl-1,3-dioxolan-2-yl)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole

Trifluoroacetic anhydride (0.25 ml, 1.8 mmol) at 0°C and stirred at 25°C for 16 hours. The reaction mixture was diluted with ethyl acetate (40 ml) and washed twice with sodium bicarbonate solution (40 ml). The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography using 30% ethyl acetate in hexane as eluent on silica gel to give 3-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-(trifluoromethyl)- 1,2,4-oxadiazole (0.2 g, 49% yield).

d) Step 4. 1-(4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one

Into a stirred solution of 3-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole (10 g, 33 mmol) and acetone (50 ml) iodine (0.5 g, 2 mmol) was added at 25°C for 3 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, diluted with ethyl acetate (80 ml) and washed with water (40 ml). The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude residue was purified by column chromatography using 30% ethyl acetate in hexane as eluent on silica gel to give 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane-1 -ona (6 g, yield 70%).

e) Step 5. 2-Bromo-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one

Bromine ( 2.3 ml, 43 mmol) at 0°C. The resulting reaction mixture was stirred for 3 hours at 25°C. After completion of the reaction, the reaction mixture was diluted with dichloromethane (120 ml) and washed with water (80 ml). The dichloromethane layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by column chromatography using 10% ethyl acetate in hexane as eluent on silica gel to give 2-bromo-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl )ethan-1-one (11 g, 53% yield).

f) Step 6. 2-(2-Chloro-5-methylphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one

Into a stirred solution of 2-bromo-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (0.2 g, 0.6 mmol) and acetonitrile (8 ml), potassium carbonate (0.18 g, 1.3 mmol) and 2-chloro-5-methylphenol (0.17 g, 1.2 mmol) were added at 0°C under nitrogen atmosphere. The resulting reaction mixture was stirred for 1 hour at 25°C. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (10 ml) and washed with water (10 ml). The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by column chromatography using 20% ethyl acetate in hexane as eluent on silica gel to give 2-(2-chloro-5-methylphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4 -oxadiazol-3-yl)phenyl)ethan-1-one (0.15 g, 63% yield). ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.26-8.21 (m, 4H), 7.30 (d, 1H), 7.00 (d, 1H), 6.77 (dd, 1H), 5.75 (s, 2H), 2.24 (s, 3H).

Table 1. The following compounds were prepared by applying a similar procedure to that described in Example 1

Example 2. Preparation of 2-((4-methoxyphenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (compound 23)

Into a stirred solution of 2-bromo-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (0.3 g, 0.9 mmol) and acetonitrile (8 ml), potassium carbonate (0.27 g, 2 mmol) and 4-methoxybenzenethiol (0.13 g, 0.9 mmol) were added at 0°C. The resulting reaction mixture was stirred for 1 hour at 25°C. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (10 ml) and washed with water (10 ml). The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by column chromatography using 20% ethyl acetate in hexane as eluent on silica gel to give 2-((4-methoxyphenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4- Oxadiazol-3-yl)phenyl)ethan-1-one (0.19 g, 54% yield).

Table 2. The following compounds were prepared using a similar procedure described in example 2

Connection no. IUPAC name Analytical data 13 2-((2,6-Dichlorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.23 (dd, 4H), 7.67 (d, 1H), 7.55 (d, 1H), 7.35 (dd, 1H), 4 .90 (s, 2H); LCMS (M−1): 430.80 14 2-((3-methoxyphenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.24-8.19 (m, 4H), 7.23-7.19 (m, 1H), 6.91-6.89 (m, 2H ), 6.78-6.75 (m, 1H), 4.73 (s, 2H), 3.72 (s, 3H); LCMS (M−H): 392.9 22 2-(p-Tolylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.24-8.19 (m, 4H), 7.27 (d, 2H), 7.13 (d, 2H), 4.63 (s, 2H), 2.27 (s, 3H); LCMS (M−H): 377 24 2-(Cyclopentylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.24-8.19 (m, 4H), 4.09 (s, 2H), 3.13-3.06 (m, 1H), 1, 99-1.91 (m, 2H), 1.68-1.38 (m, 6H); LCMS (M−H): 354.7 25 2-(Benzo[d]oxazol-2-ylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.33-8.27 (m, 4H), 7.67-7.60 (m, 2H), 7.36-7.31 (m, 2H ), 5.27 (s, 2H); LCMS (M+H): 406.1 26 2-((4-Methylthiazol-2-yl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.28-8.23 (m, 4H), 7.18 (t, 1H), 5.01 (s, 2H), 2.26 (d, 3H); LCMS (M+H): 386.35 52 2-((3,4-Dichlorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.23 (dd, 4H), 7.67 (d, 1H), 7.55 (d, 1H), 7.35 (dd, 1H), 4 .90 (s, 2H); LCMS (M−1): 430.80 53 2-((4-Chlorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.21 (s, 4H), 7.35-7.39 (m, 4H), 4.77 (s, 2H); LCMS (M−1): 396.80 54 2-((3-Chlorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.20-8.26 (m, 4H), 7.45-7.46 (m, 1H), 7.31-7.32 (m, 2H ), 7.23-7.26 (m, 1H), 4.86 (s, 2H); LCMS (M−1): 396.70 55 2-((3,4-Difluorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.17-8.23 (m, 4H), 7.51-7.56 (m, 1H), 7.34-7.42 (m, 1H ), 7.18-7.22 (m, 1H), 4.81 (s, 2H); LCMS (M−1): 398.95 56 2-(Benzylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.15-8.21 (m, 4H), 7.22-7.32 (m, 5H), 3.95 (s, 2H), 3, 73 (d, 2H); LCMS (M−1): 376.80 57 2-((4-Methoxybenzyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.17-8.23 (m, 4H), 7.22-7.27 (m, 2H), 6.87-6.90 (m, 2H ), 3.95 (s, 2H), 3.74 (d, 3H), 3.70 (d, 2H); LCMS (M−1): 406.80 58 2-((1-Phenylethyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.16-8.19 (m, 2H), 8.09-8.12 (m, 2H), 7.29-7.35 (m, 4H ), 7.21-7.26 (m, 1H), 3.98-4.08 (m, 2H), 3.72 (d, 1H), 1.51 (d, 3H); LCMS (M−1): 390.80 59 2-(Cyclohexylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.17-8.23 (m, 4H), 4.07 (s, 2H), 2.66-2.72 (m, 1H), 1, 88-1.91 (m, 2H), 1.52-1.66 (m, 3H), 1.16-1.30 (m, 5H); LCMS (M−1): 368.80 60 2-(Phenylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.18-8.23 (m, 4H), 7.28-7.37 (m, 4H), 7.18-7.22 (m, 1H ), 4.72 (s, 2H); LCMS (M−1): 362.80 61 2-(Allylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.17-8.23 (m, 4H), 5.71-5.81 (m, 1H), 5.09-5.17 (m, 2H ), 4.00 (s, 2H), 3.14 (ddt, 2H); LCMS (M−1): 326.80 62 1-(4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3-(trifluoromethyl)phenyl)thio)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.20-8.25 (m, 4H), 7.71 (d, 1H), 7.64-7.67 (m, 1H), 7. 50-7.55 (m, 2H), 4.87-4.95 (m, 2H); LCMS (M−1): 430.80 63 2-((2-Methoxyphenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.18-8.22 (m, 4H), 7.18-7.26 (m, 2H), 6.87-6.99 (m, 2H ), 4.56 (s, 2H), 3.78 (s, 3H); LCMS (M−1): 392.75 64 2-((3-Fluorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.23 (qd, 4H), 7.33 (td, 1H), 7.26 (dt, 1H), 7.17 (dq, 1H), 6 .98-7.03 (m, 1H), 4.85 (s, 2H); LCMS (M−1): 380.90 65 2-((2-Fluorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.17-8.21 (m, 4H), 7.42 (td, 1H), 7.12-7.30 (m, 3H), 4, 70 (s, 2H); LCMS (M−1): 380.95 66 2-(o-Tolylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 7.37-7.42 (m, 4H), 6.50 (dd, 1H), 6.37-6.38 (m, 1H), 6, 27-6.36 (m, 2H), 3.85 (s, 2H), 1.44 (s, 3H); LCMS (M−1): 376.75 67 2-(m-Tolylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.18-8.23 (m, 4H), 7.13-7.20 (m, 3H), 7.00-7.02 (m, 1H ), 4.69 (s, 2H), 2.25 (s, 3H); LCMS (M−1): 376.95 68 2-(Pyridin-4-ylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.36 (dd, 2H), 8.27-8.30 (m, 2H), 8.22-8.25 (m, 2H), 7, 32 (dd, 2H), 4.98 (s, 2H); LCMS (M−1): 363.95 69 2-(Isopropylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.20 (s, 4H), 4.09 (s, 2H), 2.87-2.94 (m, 1H), 1.20 (d, 6H); LCMS (M−1): 329.00 70 2-(tert-Butylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.16-8.22 (m, 4H), 4.13 (s, 2H), 1.29 (s, 9H); LCMS (M−1): 343.00 71 1-(4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethyl)phenyl)thio)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.21-8.27 (m, 4H), 7.63 (d, 2H), 7.54 (d, 2H), 4.94 (s, 2H); LCMS (M−1): 430.90 72 1-(4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethyl)pyrimidin-2-yl)thio)ethan-1-one ^1H -NMR (400 MHz, DMSO -d6 ) δ 8.94 (d, 1H), 8.23-8.28 (m, 4H), 7.69 (d, 1H), 4.93 (s, 2H); LCMS (M−1): 432.90 73 2-(Thiazol-2-ylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.24 (dd, 4H), 7.67 (d, 1H), 7.64 (d, 1H), 5.05 (s, 2H); LCMS (M−1): 369.90 74 2-(Pyridin-2-ylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.30 (dq, 1H), 8.17-8.27 (m, 4H), 7.62-7.66 (m, 1H), 7, 37-7.42 (m, 1H), 7.09 (ddd, 1H), 4.85 (s, 2H); LCMS (M−1): 363.70 75 2-((4-Methyl-4H-1,2,4-triazol-3-yl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl )ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.53 (s, 1H), 8.22 (s, 4H), 4.91 (s, 2H), 3.60 (s, 3H); LCMS (M−1): 367.75 76 2-((1,3,4-Thiadiazol-2-yl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.50 (s, 1H), 8.24-8.29 (m, 4H), 5.21 (s, 2H); LCMS (M+1): 372.95 149 2-((1H-1,2,4-Triazol-5-yl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane-1 -He ^1H -NMR (400 MHz, DMSO -d6 ) δ 13.98 (s, 1H), 8.39 (s, 1H), 8.22 (s, 4H), 4.85 (s, 2H), LCMS (M−1): 353.70 150 2-((5-Methyl-1,3,4-oxadiazol-2-yl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane -1-he ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.25 (s, 4H), 5.13 (s, 2H), 2.47 (s, 3H); LCMS (M+1): 370.95 151 2-((4-Methylpyridin-2-yl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.21-8.26 (m, 4H), 8.16 (dd, 1H), 7.22 (t, 1H), 6.92-6, 93 (m, 1H), 4.82 (s, 2H), 2.25 (s, 3H); LCMS (M+1): 380.00 152 2-((2-Hydroxyethyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.17-8.22 (m, 4H), 4.80 (t, 1H), 4.08 (s, 2H), 3.50-3, 55 (m, 2H), 2.57 (t, 2H); LCMS (M−1): 330.95

Example 3. Preparation of 2-((3,4-difluorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (compound 27)

Sodium bicarbonate (0.11 g, 1.3 mmol) and potassium iodide (0.02 g, 0.1 mmol) at 0°C. The mixture was stirred for 15 minutes. at 25°C. Then 2-bromo-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (0.22 g, 0.7 mmol) was added at 0 °C and the resulting reaction mixture was stirred at 25°C for 1 hour. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (10 ml) and washed with water (10 ml). The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by column chromatography using 20% ethyl acetate in hexane as eluent on silica gel to give 2-((3,4-difluorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2. 4-oxadiazol-3-yl)phenyl)ethan-1-one (0.12 g, 0.3 mmol, 47% yield).

Table 3. The following compounds were prepared using a similar procedure described in example 3

Connection no. IUPAC name Analytical data 28 1-(4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethyl)phenyl)amino)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.31-8.25 (m, 4H), 7.40 (d, 2H), 6.83 (d, 2H), 6.71-6, 68 (m, 1H), 4.87 (d, 2H); LCMS (M+H): 415.95

Example 4 Synthesis of 2-(phenylamino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (compound 137)

Into a stirred solution of 2-bromo-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (0.2 g, 0.6 mmol) and ethanol (10 ml) under nitrogen atmosphere, aniline (0.056 g, 0.6 mmol) and sodium bicarbonate (0.060 g, 0.72 mmol) were added at 25°C. The resulting reaction mixture was stirred at 25°C for 12 hours. After completion of the reaction, the reaction mixture was quenched by adding water (10 ml) and the product was extracted three times with ethyl acetate (20 ml). The combined ethyl acetate layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by preparative HPLC to give 2-(phenylamino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (0.14 g, 0.4 mmol, yield 67%).

Table 4. The following compounds were prepared using a similar procedure described in example 4

Connection no. IUPAC name Analytical data 32 2-((3-Methoxyphenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.27-8.29 (m, 2H), 8.22 (dd, 2H), 6.97 (t, 1H), 6.27-6, 30 (m, 2H), 6.15 (ddd, 1H), 5.90 (t, 1H), 4.72 (d, 2H), 3.67 (s, 3H); LCMS (M+H) 377.95 138 2-((4-Fluorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.25 (ddd, 4H), 6.89-6.95 (m, 2H), 6.67-6.72 (m, 2H), 5, 86 (t, 1H), 4.72 (d, 2H); LCMS (M−H): 363.75 139 2-((2,4-Difluorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.25 (dd, 4H), 7.09-7.15 (m, 1H), 6.83-6.87 (m, 1H), 6, 76 (td, 1H), 5.49 (s, 1H), 4.79 (d, 2H); LCMS (M+H) 384 140 2-((4-Chloro-3-(trifluoromethyl)phenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.17-8.31 (m, 5H), 7.37 (d, 1H), 7.21 (d, 1H), 6.98 (dd, 1H), 6.66 (t, 1H), 4.87 (t, 2H); LCMS (M+H) 450 141 1-(4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3-(trifluoromethyl)phenyl)amino)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.29 (dd, 2H), 8.24 (dd, 2H), 7.28 (t, 1H), 7.03 (s, 1H), 6 .96-6.99 (m, 1H), 6.85 (d, 1H), 6.43 (t, 1H), 4.85 (d, 2H); LCMS (M+H): 415.95 143 2-((3-Fluorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.28 (dd, 2H), 8.23 (dd, 2H), 7.04-7.10 (m, 1H), 6.50-6, 56 (m, 2H), 6.30-6.34 (m, 1H), 6.26 (t, 1H), 4.77 (d, 2H); LCMS (M+H): 366 144 2-(m-Tolylamino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.26-8.29 (m, 2H), 8.21-8.24 (m, 2H), 6.95 (t, J = 7.7 Hz, 1H), 6.48-6.51 (m, 2H), 6.39 (d, 1H), 5.78 (t, 1H), 4.72 (d, 2H), 2.18 (s , 3H); LCMS (M+H): 361.75 145 2-((4-Methoxyphenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.26-8.28 (m, 2H), 8.21-8.23 (m, 2H), 6.70-6.74 (m, 2H ), 6.62-6.67 (m, 2H), 5.50 (t, 1H), 4.68 (d, 2H), 3.63 (s, 3H); LCMS (M+H): 377.75 146 2-(o-Tolylamino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.29 (ddd, 4H), 7.01 (t, 2H), 6.54-6.58 (m, 2H), 5.18 (t, 1H), 4.79 (d, 2H), 2.18 (s, 3H); LCMS (M+H): 361.75 147 2-((2-Methoxyphenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.28-8.31 (m, 2H), 8.23 (dd, 2H), 6.85 (dd, 1H), 6.78 (td, 1H), 6.64 (dd, 1H), 6.60 (td, 1H), 5.32 (t, 1H), 4.77 (d, 2H), 3.83-3.88 (m, 3H ); LCMS (M+H) 377.8 148 4-Amino-1-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyridinium-1-ium bromide ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.30 (dd, 2H), 8.24 (dd, 2H), 7.62-7.65 (m, 2H), 7.23-7, 27 (m, 2H), 7.16 (t, 1H), 6.96 (t, 1H), 6.82-6.84 (m, 1H), 6.72 (dd, 1H), 6.01 (t, 1H), 4.84 (d, 2H); LCMS (M+H) 441.95

Example 5. Preparation of 2-((4-chlorophenyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (compound 78)

Into a stirred solution of 2-((4-chlorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (0.2 g , 0.502 mmol) in methanol (6 ml), an aqueous (1 ml) solution of oxon (0.262 g, 0.426 mmol) was added at 0°C. The reaction mixture was stirred for 30 minutes. at 0°C. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (8 ml) and washed with water (10 ml). The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude residue was purified by column chromatography using 15% ethyl acetate in hexane as eluent on silica gel to give 2-((4-chlorophenyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4- Oxadiazol-3-yl)phenyl)ethan-1-one (115 mg, 0.277 mmol, 55% yield). ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.15-8.20 (m, 4H), 7.76 (dt, 2H), 7.66 (dt, 2H), 4.91 (d, 1H), 4.80 (d, 1H); LCMS (M−1) 412.85.

Table 5. The following compounds were prepared using a similar procedure described in example 5

Connection no. IUPAC name Analytical data 79 2-((3,4-Difluorophenyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO-D6) δ 8.16-8.21 (m, 4H), 7.83-7.88 (m, 1H), 7.66-7.73 (m, 1H ), 7.60-7.64 (m, 1H), 4.94 (d, 1H), 4.85 (d, 1H); LCMS (M−1): 414.80 80 2-(Benzylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO-D6) δ 8.19-8.25 (m, 4H), 7.33-7.42 (m, 5H), 4.71 (d, 1H), 4, 60 (d, 1H), 4.35 (d, 1H), 4.16 (d, 1H); LCMS (M−1): 393 81 2-((4-Methoxybenzyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO-D6) δ 8.18-8.25 (m, 4H), 7.26-7.35 (m, 2H), 6.92-6.98 (m, 2H ), 4.66 (d, 1H), 4.54 (d, 1H), 4.28 (d, 1H), 4.10 (d, 1H), 3.74 (s, 3H); LCMS (M−1): 422.85 82 2-((1-Phenylethyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO-D6) δ 8.18-8.22 (m, 2H), 8.12-8.16 (m, 2H), 7.32-7.42 (m, 5H ), 4.52 (d, 1H), 4.42 (d, 1H), 4.33 (q, 1H), 1.67 (dd, 3H); LCMS (M−1): 406.80 83 2-((5-Methylthiazol-2-yl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO-D6) δ 8.16-8.21 (m, 4H), 7.69 (d, 1H), 5.11 (dd, 2H), 2.41 (dd, 3H); LCMS (M−1): 399.75 84 2-(Phenylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO-D6) δ 8.15-8.20 (m, 4H), 7.72-7.75 (m, 2H), 7.52-7.60 (m, 3H ), 4.85 (d, 1H), 4.79 (d, 1H); LCMS (M−1): 378.85 85 1-(4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3-(trifluoromethyl)phenyl)sulfinyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO-D6) δ 8.14-8.19 (m, 4H), 8.03-8.08 (m, 2H), 7.92 (dd, 1H), 7. 82 (t, 1H), 4.99 (d, 1H), 4.90 (d, 1H); LCMS (M−1): 446.80 86 2-(p-Tolylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO-D6) δ 8.14-8.20 (m, 4H), 7.61-7.63 (m, 2H), 7.38 (d, 2H), 4, 78 (dd, 2H), 2.32-2.39 (m, 3H); LCMS (M−1): 392.80 87 2-((3-Fluorophenyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO-D6) δ 8.16-8.21 (m, 4H), 7.57-7.66 (m, 3H), 7.37-7.41 (m, 1H ), 4.92 (d, 1H), 4.84 (d, 1H); LCMS (M−1): 396.85 88 2-((2-Fluorophenyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO-D6) δ 8.15-8.20 (m, 4H), 7.74 (td, 1H), 7.60-7.66 (m, 1H), 7. 46 (td, 1H), 7.36-7.40 (m, 1H), 4.97 (d, 1H), 4.84 (d, 1H); LCMS (M−1): 396.85 89 2-(o-Tolylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO-D6) δ 8.14-8.20 (m, 4H), 7.78 (dt, 1H), 7.41-7.46 (m, 2H), 7. 29-7.32 (m, 1H), 4.81 (d, 1H), 4.66 (d, 1H), 2.38 (s, 3H); LCMS (M−1): 392.90 90 2-(m-Tolylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ^1H -NMR (400 MHz, DMSO-D6) δ 8.15-8.20 (m, 4H), 7.55 (s, 1H), 7.51 (d, 1H), 7.45 (t, 1H), 7.34 (d, 1H), 4.79 (dd, 2H), 2.37 (d, 3H); LCMS (M−1): 392.90 91 2-(tert-Butylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO-D6) δ 8.26 (s, 4H), 4.55 (d, 1H), 4.30 (d, 1H), 1.27 (s, 9H); LCMS (M−1): 359.05 92 1-(4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethyl)phenyl)sulfinyl)ethan-1-one ^1H -NMR (400 MHz, DMSO-D6) δ 8.17-8.22 (m, 4H), 7.98 (s, 4H), 5.00 (d, 1H), 4.88 (d, 1H); LCMS (M−1): 446.95 93 2-(Isopropylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO-D6) δ 8.24 (s, 4H), 4.64 (d, 1H), 4.50 (d, 1H), 3.02-3.09 (m, 1H), 1.24 (dd, 6H); LCMS (M+1) 347

Example 6. Preparation of 2-((3-fluorophenyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (compound 105)

Into a stirred solution of 2-((3-fluorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (0.15 g , 0.39 mmol) in a mixture of methanol (8 ml) and water (2 ml) was added oxon (0.482 g, 0.785 mmol) at 0°C. The result was a reaction mixture, which was further stirred at 25°C for 30 minutes. and then heated at 60°C for 3 hours. Once complete, the reaction mixture was quenched with water (50 ml) and extracted three times with ethyl acetate (50 ml). The combined ethyl acetate layer was washed twice with brine (25 ml), dried over sodium sulfate and evaporated under reduced pressure to dryness to give 2-((3-fluorophenyl)sulfonyl)-1-(4-(5-(trifluoromethyl) -1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (120 mg, 0.29 mmol, 75% yield).¹H-NMR (400 MHz, DMSO-d6) δ 8.16-8.21 (m, 4H), 7.77-7.80 (m, 2H), 7.71 (td, 1H), 7.60-7.64 (m, 1H), 5.55(s, 2H); LCMS (M−1): 412.95.

Table 6. The following compounds were prepared using a similar procedure described in example 6

Connection no. IUPAC name Analytical data 94 2-((3,4-Dichlorophenyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ^1H -NMR (400 MHz, DMSO -d6 ) δ 8.15-8.22 (m, 5H), 7.95 (d, 1H), 7.89 (dd, 1H), 5.62 (s, 2H); LCMS (M−1) 462.70 95 2-((4-Chlorophenyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.15-8.21 (m, 4H), 7.92-7.97 (m, 2H), 7.73 (dt, 2H), 5, 51 (s, 2H); LCMS (M−1): 428.75 96 2-((3,4-Difluorophenyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.16-8.22 (m, 4H), 8.05-8.10 (m, 1H), 7.81-7.84 (m, 1H ), 7.72-7.78 (m, 1H), 5.56 (s, 2H); LCMS (M−1): 430.80 97 2-(Benzylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.16-8.30 (m, 4H), 7.40-7.50 (m, 5H), 5.09 (s, 2H), 4, 70 (d, 2H); LCMS (M−1): 409 98 2-((4-Methoxybenzyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.25 (d, 4H), 7.33-7.35 (m, 2H), 6.96-6.99 (m, 2H), 5, 04 (s, 2H), 4.63 (d, 2H), 3.74 (d, 3H); LCMS (M−1): 438.80 99 2-((1-Phenylethyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.15-8.23 (m, 4H), 7.37-7.56 (m, 5H), 4.96 (t, 2H), 4, 81 (q, 1H), 1.65-1.72 (m, 3H); LCMS (M−1): 422.85 100 2-(Cyclohexylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.15-8.35 (m, 4H), 5.11-5.28 (m, 2H), 3.32-3.35 (m, 1H ), 3.26-3.32 (m, 1H), 2.11-2.17 (m, 2H), 1.84 (dd, 2H), 1.65 (d, 1H), 1.11- 1.46 (m, 5H); LCMS (M−1): 400.95 101 2-((5-Methylthiazol-2-yl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.16-8.21 (m, 4H), 7.86 (d, 1H), 5.70 (d, 2H), 2.41 (dd, 3H); LCMS (M−1): 415.80 102 2-(Phenylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.15-8.19 (m, 4H), 7.90-7.93 (m, 2H), 7.71-7.75 (m, 1H ), 7.61-7.66 (m, 2H), 5.43 (s, 2H); LCMS (M−1): 394.80 103 1-(4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3-(trifluoromethyl)phenyl)sulfonyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.24-8.26 (m, 2H), 8.13-8.20 (m, 5H), 7.91 (t, 1H), 5, 65 (s, 2H); LCMS (M−1): 462.75 104 2-(o-Tolylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.15-8.20 (m, 4H), 7.80 (dd, 1H), 7.61 (td, 1H), 7.40-7, 46 (m, 2H), 5.34 (s, 2H), 2.67 (s, 3H); LCMS (M−1): 408.95 106 2-(Isopropylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.23-8.28 (m, 4H), 5.14 (s, 2H), 3.49-3.56 (m, 1H), 1, 30-1.34 (m, 6H); LCMS (M−1): 360.75 107 2-(Thiazol-2-ylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.30 (d, 1H), 8.14-8.22 (m, 5H), 5.70 (d, 2H); LCMS (M−1): 401.70 108 2-(tert-Butylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.24 (s, 4H), 5.03 (s, 2H), 1.39 (s, 9H); LCMS (M−1): 374.80 109 1-(4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethyl)phenyl)sulfonyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.18 (dd, 6H), 8.05 (d, 2H), 5.62 (s, 2H); LCMS (M−1): 462.85 110 2-(m-Tolylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.14-8.19 (m, 4H), 7.68-7.72 (m, 2H), 7.49-7.55 (m, 2H ), 5.39 (s, 2H), 2.38 (s, 3H); LCMS (M−1): 408.85 111 2-((2-Fluorophenyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.20 (s, 4H), 7.79-7.86 (m, 2H), 7.50-7.55 (m, 1H), 7. 44-7.48 (m, 1H), 5.46 (s, 2H): LCMS (M−1): 412.75 112 2-(Pyridin-4-ylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.93 (dd, 2H), 8.16-8.22 (m, 4H), 7.91 (dd, 2H), 5.67 (s, 2H). LCMS (M−1): 395.85

Example 7. Preparation of 2-((3-fluorophenyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one (connection no. 115)

a) Stage-1. 6-(1-Ethoxyvinyl)nicotinonitrile

To a stirred solution of 6-chloronicotinonitrile (15 g, 108 mmol) in toluene (120 ml) was added (1-ethoxyvinyl)tributyl stannane (40 ml, 119 mmol) and bis(triphenylphosphine) palladium(II) dichloride (3.8 g, 5 .4 mmol) at 25°C. The reaction mixture was degassed with nitrogen for 15 minutes. and then the reaction mixture was heated at 80°C for 16 hours. The reaction mixture was filtered through a pad of celite, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using 10% ethyl acetate in hexane as eluent to give 6-(1-ethoxyvinyl)nicotinonitrile (16 g, 87% yield).

b) Stage-2. 6-(1-Ethoxyvinyl)-N'-hydroxynicotinimidamide

Hydroxylamine (7 mL, 114 mmol) was added to a stirred solution of 6-(1-ethoxyvinyl)nicotinonitrile (16 g, 95 mmol) in ethanol (120 mL) at 25°C. The reaction mixture was then stirred at 25°C for 12 hours. The reaction mixture was concentrated under reduced pressure to obtain 6-(1-ethoxyvinyl)-N'-hydroxynicotinimidamide (19 g, 98% yield).

c) Stage-3. 3-(6-(1-Ethoxyvinyl)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole

To a stirred solution of 6-(1-ethoxyvinyl)-N'-hydroxynicotinimidamide (18 g, 87 mmol) in tetrahydrofuran (160 ml), triethylamine (15 ml, 104 mmol) was slowly added at 0°C, then trifluoroacetic anhydride (15 ml, 104 mmol) at 0°C. The reaction mixture was stirred for 12 hours at 25°C. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (200 ml) and washed twice with saturated sodium bicarbonate solution (200 ml); the organic layer was separated, dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using 15% ethyl acetate in hexane as eluent to give 3-(6-(1-ethoxyvinyl)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4- oxadiazole (11 g, 40 mmol, yield 46%).

d) Stage-4. 2-Bromo-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one

To a stirred solution of 3-(6-(1-ethoxyvinyl)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole (11 g, 38.6 mmol) in tetrahydrofuran (100 ml) was added slowly water (4 ml), N-bromosuccinimide (5.8 g, 33 mmol) at 0°C, the reaction mixture was stirred for 2 hours at 25°C. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (200 ml) and washed with water (200 ml), the organic layer was separated, dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using 10% ethyl acetate in hexane as eluent to give 2-bromo-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridine -2-yl)ethan-1-one (8 g, 24 mmol, 63% yield).

e) Stage-6. 2-((3-Fluorophenyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one

To a stirred solution of 3-fluorobenzenethiol (0.06 ml, 0.71 mmol) in acetonitrile (8 ml) was added potassium carbonate (0.1 g, 0.7 mmol) at 25°C, then 2-bromo-1- (5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one (0.2 g, 0.6 mmol) at 25°C. The reaction was stirred at 25°C for 4 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane (20 ml) and washed twice with water (20 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative HPLC to give 2-((3-fluorophenyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl) ethan-1-one (65 mg, 28% yield).

Table 7. The following compounds were prepared using a similar procedure described in example 7

Connection no. IUPAC name Analytical data 115 2-((3-Fluorophenyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.36 (q, 1H), 8.65 (dd, 1H), 8.20 (dd, 1H), 7.34 (td, 1H), 7 .26 (dt, 1H), 7.18 (dq, 1H), 7.05-6.99 (m, 1H), 4.80 (s, 2H); LCMS (M+1): 383.95 116 2-((4-Methoxyphenyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.31 (q, 1H), 8.64 (dd, 1H), 8.17 (dd, 1H), 7.35-7.31 (m, 2H), 6.91-6.87 (m, 2H), 4.49 (s, 2H), 3.78-3.73 (m, 3H); LCMS (M+1) : 396.00 117 2-((4-Methoxybenzyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.33 (q, 1H), 8.65 (dd, 1H), 8.22 (dd, 1H), 7.26-7.22 (m, 2H), 6.88-6.84 (m, 2H), 3.97 (s, 2H), 3.72-3.69 (m, 5H); LCMS (M+1) : 409.75 118 2-(Benzylthio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.33 (q, 1H), 8.65 (dd, 1H), 8.22 (dd, 1H), 7.35-7.22 (m, 5H), 3.99 (s, 2H), 3.76 (s, 2H); LCMS (M+1): 379.95 119 2-(Cyclopentylthio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.33 (q, 1H), 8.64 (dd, 1H), 8.22 (dd, 1H), 4.11 (s, 2H), 3 .16-3.10 (m, 1H), 1.99-1.91 (m, 2H), 1.69-1.59 (m, 2H), 1.58-1.47 (m, 2H) , 1.45-1.37 (m, 2H); LCMS (M+1): 357.70 120 2-((2,6-Dichlorophenyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.23 (q, 1H), 8.64 (dd, 1H), 8.18 (dd, 1H), 7.56 (dd, 2H), 7 .42 (dd, 1H), 4.47 (s, 2H); LCMS (M+1): 435.65 121 2-(Benzo[d]oxazol-2-ylthio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.43 (q, 1H), 8.69 (dd, 1H), 8.24 (dd, 1H), 7.67-7.56 (m, 2H), 7.33-7.29 (m, 2H), 5.28 (d, 2H); LCMS (M+1): 406.70 122 2-((4-(Trifluoromethoxy)phenyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.34 (q, 1H), 8.65 (dd, 1H), 8.19 (dd, 1H), 7.51-7.48 (m, 2H), 7.31 (dd, 2H), 4.77 (s, 2H); LCMS (M−1): 447.90 123 2-((4-Methoxyphenyl)sulfonyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.26 (q, 1H), 8.63 (dd, 1H), 8.15 (dd, 1H), 7.82-7.78 (m, 2H), 7.13-7.09 (m, 2H), 5.35 (s, 2H), 3.83 (s, 3H); LCMS (M+1): 428.05 124 2-((4-Methoxybenzyl)sulfonyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.39 (q, 1H), 8.69 (dd, 1H), 8.26 (dd, 1H), 7.36-7.27 (m, 2H), 6.98-6.92 (m, 2H), 5.10 (s, 2H), 4.62 (d, 2H), 3.75 (d, 3H); LCMS (M−1): 439.75 125 2-(Benzylsulfonyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.38 (dq, 1H), 8.70-8.65 (m, 1H), 8.28-8.20 (m, 1H), 7, 45-7.37 (m, 5H), 5.13 (d, 2H), 4.79-4.63 (m, 2H); LCMS (M−1): 409.75 126 2-(Cyclopentylsulfonyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.41 (q, 1H), 8.68 (dd, 1H), 8.26 (dd, 1H), 5.16 (s, 2H), 3 .91-3.83 (m, 1H), 2.02-1.90 (m, 4H), 1.58-1.67 (m, 4H); LCMS (M−1): 387.90 127 2-((3-Fluorophenyl)sulfonyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.29 (q, 1H), 8.64 (dd, 1H), 8.17 (dd, 1H), 7.80-7.76 (m, 2H), 7.73-7.68 (m, 1H), 7.65-7.59 (m, 1H), 5.53 (s, 2H); LCMS (M−1): 413.70 128 2-((3-Fluorophenyl)sulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.29 (q, 1H), 8.64 (dd, 1H), 8.18 (dd, 1H), 7.65-7.55 (m, 3H), 7.40-7.35 (m, 1H), 4.90 (dd, 2H); LCMS (M+1): 399.70 129 2-((4-Methoxyphenyl)sulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.29 (q, 1H), 8.62 (dd, 1H), 8.14 (dd, 1H), 7.65-7.61 (m, 2H), 7.09 (dt, 2H), 4.86 (d, 1H), 4.75 (d, 1H), 3.78 (s, 3H); LCMS (M+1): 411.95 130 2-((4-Methoxybenzyl)sulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.36 (q, 1H), 8.66 (dd, 1H), 8.20 (dd, 1H), 7.29-7.27 (m, 2H), 6.93 (dd, 2H), 4.73 (d, 1H), 4.59 (d, 1H), 4.29 (d, 1H), 4.12 (d, 1H), 3, 75 (s, 3H); LCMS (M+1): 425.95 131 2-(Benzylsulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.36 (q, 1H), 8.67 (dd, 1H), 8.21 (dd, 1H), 7.40-7.34 (m, 5H), 4.77 (d, 1H), 4.64 (d, 1H), 4.36 (d, 1H), 4.19 (d, 1H); LCMS (M+1): 396.05 132 2-((2,6-Dichlorophenyl)sulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.32 (q, 1H), 8.65 (dd, 1H), 8.19 (dd, 1H), 7.59-7.52 (m, 3H), 5.50 (d, 1H), 5.16 (d, 1H); LCMS (M−1): 449.50 133 2-(cyclopentylsulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.38 (q, 1H), 8.67 (dd, 1H), 8.23 (dd, 1H), 4.71 (d, 1H), 4 .55 (d, 1H), 3.41-3.34 (m, 1H), 2.06-1.85 (m, 3H), 1.65-1.57 (m, 5H); LCMS (M−1): 372.00

Example 8. Preparation of 2-(2-fluorophenoxy)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one (compound 114 )

Potassium carbonate (0.18 g, 1.3 mmol) was added to a stirred solution of 2-fluorophenol (0.08 g, 0.71 mmol) in acetonitrile (8 ml) under nitrogen atmosphere at 0°C. The reaction mixture was stirred for 15 minutes. at 0°C, then added 2-bromo-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one (0.2 g, 0.6 mmol) at 0°C. The reaction mixture was stirred for 4 hours at 25°C. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (10 ml) and washed with water (20 ml). The organic layer was dried over anhydrous sodium sulfate; the solvent was evaporated under reduced pressure to obtain the crude product. The crude product was purified by preparative HPLC to give 2-(2-fluorophenoxy)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethane-1 -ona (55 mg, yield 25%). ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.37 (t, 1H), 8.68 (dd, 1H), 8.19 (d, 1H), 7.26-7.20 (m, 1H), 7.14 (td, 1H), 7.06 (t, 1H), 6.97-6.92 (m, 1H), 5.85 (s, 2H); LCMS (M+1): 367.95.

Example 9. Preparation of 2-((2-fluorophenyl)amino)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one (connection 153)

In a solution of 2-bromo-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one (0.35 g, 1.04 mmol) in ethanol (8 ml), sodium bicarbonate (0.17 g, 2.08 mmol) and 2-fluoroaniline (0.14 g, 1.25 mmol) were added at 25°C, the reaction was stirred at 25°C for 12 hours After completion of the reaction, the reaction mixture was diluted with ethyl acetate (25 ml) and washed with water (30 ml); the organic layer was separated, dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel flash column chromatography using 10% ethyl acetate in hexane as eluent to give 2-((2-fluorophenyl)amino)-1-(5-(5-(trifluoromethyl)-1,2. 4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one (60 mg, 0.164 mmol, 16% yield). ¹ H-NMR (400 MHz, DMSO -d6 ) δ 9.39 (q, 1H), 8.67 (dd, 1H), 8.19 (dd, 1H), 7.05 (ddd, 1H), 6 .93 (t, 1H), 6.70-6.66 (m, 1H), 6.61-6.55 (m, 1H), 5.59-5.56 (m, 1H), 4.92 (d, 2H); LCMS (M+1): 366.85.

Example 10. Preparation of N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide (compound 77)

To a stirred solution of benzenesulfonohydrazide (0.2 g, 1.15 mmol) in methanol (5 ml) was added 3-bromobenzaldehyde (0.135 ml, 1.15 mmol). The reaction mixture was stirred at 65°C for 2 hours. The reaction mixture was concentrated under reduced pressure to obtain the crude product, then the crude compound was dissolved in acetonitrile (5 ml), 2-bromo-1-(4-(5-(trifluoromethyl) -1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (0.35 g, 1.04 mmol), cesium carbonate (0.034 g, 0.104 mmol), then the reaction mixture was stirred at 25°C within 30 min. The reaction mixture was diluted with ethyl acetate (25 ml) and washed with water (20 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel flash column chromatography using 30% ethyl acetate in hexane as eluent to give N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)ethyl)benzenesulfonamide (67 mg, 0.16 mmol, 16% yield). ^1H -NMR (400 MHz, DMSO- d6 ) δ 8.10-8.19 (m, 5H), 7.84 (dt, J = 6.6, 1.7 Hz, 2H), 7.55- 7.65 (m, 3H), 4.54 (d, J = 5.6 Hz, 2H); LCMS (M−1): 409.85.

Table 8. The following compounds were prepared using a similar procedure to that described in Example 10

Connection no. IUPAC name Analytical data 134 4-Methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.17 (dd, J = 6.8, 2.0 Hz, 2H), 8.11 (dd, J = 6.7, 2.1 Hz, 2H), 8.05 (t, J = 5.7 Hz, 1H), 7.72 (dd, J = 6.5, 1.8 Hz, 2H), 7.36-7.38 (m, 2H ), 4.49 (d, J = 5.9 Hz, 2H), 2.37 (s, 3H); LCMS (M−1): 425.95

Example 11. Preparation of 2-hydroxy-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (compound 154)

a) Stage-1. N'-Hydroxy-4-vinylbenzimidamide

To a stirred solution of 4-vinylbenzonitrile (10 g, 77 mmol) and ethanol (200 ml) was added a 50% aqueous solution of hydroxylamine (4.74 ml, 77 mmol) at 0°C. The result was a reaction mixture, which was stirred at 65°C for 12 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain hydroxy-4-vinylbenzimidamide (10.5 g, 84% yield).

d) Stage-2. 5-(Trifluoromethyl)-3-(4-vinylphenyl)-1,2,4-oxadiazole

To a stirred solution of hydroxy-4-vinylbenzimidamide (10.5 g, 64.7 mmol) and tetrahydrofuran (100 ml) was added trifluoroacetic anhydride (13.5 ml, 97 mmol) at 0°C and stirred at 25°C for 12 hours. The reaction mixture was diluted with ethyl acetate (150 ml) and washed with sodium bicarbonate solution (40 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 5-(trifluoromethyl)-3-(4-vinylphenyl)-1,2,4-oxadiazole (11.6 g, 75% yield).

c) Stage-3. 3-(4-(Oxiran-2-yl)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole

To a stirred solution of 5-(trifluoromethyl)-3-(4-vinylphenyl)-1,2,4-oxadiazole (12 g, 50 mmol) and dichloromethane (150 ml) was added 3-chloroperoxybenzoic acid (33.2 g, 125 mmol ) at 25°C for 12 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, diluted with hexane (80 ml) and filtered. The organic layer was washed twice with 10% sodium hydroxide solution (50 ml), and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 3-(4-(oxiran-2-yl)phenyl)-5-(trifluoromethyl)-1 ,2,4-oxadiazole (10.5 g, 91% yield).

d) Stage-5. 1-(4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane-1,2-diol

Cerium nitrate was added to a stirred solution of 3-(4-(oxiran-2-yl)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole (0.3 g, 1.171 mmol) and water (20 ml). ammonium (0.128 g, 0.234 mmol) at 25°C. The resulting reaction mixture was stirred for 6 hours at 25°C. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (50 ml) and washed with water (50 ml). The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by trituration with hexane (100 ml) to give 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane-1,2-diol (0. 25 g, yield 92%).

e) Stage-6. 2-Hydroxy-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one

Into a stirred solution of 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane-1,2-diol (0.5 g, 1.823 mmol) in acetonitrile (5 ml ) and water (5 ml), sodium bromide (0.375 g, 3.65 mmol) and oxon (1.121 g, 1.823 mmol) were added at 0°C under nitrogen atmosphere. The result was a reaction mixture, which was stirred for 6 hours at 25°C. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (10 ml) and washed with sodium thiosulfate solution (80 ml) (10 ml). The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by column chromatography using 18% ethyl acetate in hexane as eluent on silica gel to give 2-hydroxy-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl )ethane-1-one. (0.20 g, 40% yield). ¹ H-NMR (400 MHz, DMSO -d6 ) δ 8.19-8.23 (d, 2H), 8.13 (d, 2H), 5.23 (t, 1H), 4.84 (d, 2H); LCMS (M−1): 270.75.

BIOLOGICAL EXAMPLES

As described herein, the compounds of general formula (I) exhibit fungicidal activity against numerous plant pathogenic fungi that attack important crops. The compounds of the present invention were evaluated for their activity as described in the following tests.

Biological test cases against fungal pathogens

Example 1. Pyricularia oryzae (rice blast)

The compounds were dissolved in 0.3% dimethyl sulfoxide solution and then added to potato dextrose agar medium immediately before distributing it into Petri dishes. 5 ml of medium with the compound at the required concentration were distributed into 60 mm sterile Petri dishes. After the medium solidified, each plate was seeded with a 5 mm mycelial disk taken from the peripheral zone of the plate with an actively growing virulent culture. The plates were incubated in growth chambers at 25°C and 60% relative humidity for seven days and then radial growth was measured in comparison with the radial growth of the untreated control. Compounds 49 66 69 70 71 73 80 83 91 106 110 112 114 118 119 128 133 145 148 149 150 at 300 ppm in these trials demonstrated at least 70% control over the untreated group, which showed extensive disease progression .

Example 2. Botrytis cinerea (gray mold)

The compounds were dissolved in 0.3% dimethyl sulfoxide solution and then added to potato dextrose agar medium immediately before distributing it into Petri dishes. 5 ml of medium with the compound at the required concentration were distributed into 60 mm sterile Petri dishes. After the medium solidified, each plate was seeded with a 5 mm mycelial disk taken from the peripheral zone of the plate with an actively growing virulent culture. The plates were incubated in growth chambers at 22°C and 90% relative humidity for seven days and then radial growth was measured in comparison with the radial growth of the untreated control. Compound 114 at 300 ppm in these trials demonstrated at least 70% control over the untreated group, which showed extensive disease development.

Example 3. Alternaria solani (tomato/potato Alternaria blight)

The compounds were dissolved in 0.3% dimethyl sulfoxide solution and then added to potato dextrose agar medium immediately before distributing it into Petri dishes. 5 ml of medium with the compound at the required concentration were distributed into 60 mm sterile Petri dishes. After the medium solidified, each plate was seeded with a 5 mm mycelial disk taken from the peripheral zone of the plate with an actively growing virulent culture. The plates were incubated in growth chambers at 25°C and 60% relative humidity for seven days and then radial growth was measured in comparison with the radial growth of the untreated control. Compounds 17 18 21 27 39 61 68 69 80 91 112 119 128 132 133 135 140 149 150 at 300 ppm in these trials demonstrated at least 70% control over the untreated group, which showed extensive disease progression.

Example 4. Colletotrichum capsici (anthracnose)

The compounds were dissolved in 0.3% dimethyl sulfoxide solution and then added to potato dextrose agar medium immediately before distributing it into Petri dishes. 5 ml of medium with the compound at the required concentration were distributed into 60 mm sterile Petri dishes. After the medium solidified, each plate was seeded with a 5 mm mycelial disk taken from the peripheral zone of the plate with an actively growing virulent culture. The plates were incubated in growth chambers at 25°C and 60% relative humidity for seven days and then radial growth was measured in comparison with the radial growth of the untreated control. Compounds 15 107 129 135 141 144 145 146 149 at 300 ppm in these trials demonstrated at least 70% control over the untreated group, which showed extensive disease progression.

Example 5. Septoria lycopersici / Corynespora cassicola (CORYCA) (Tomato leaf spot)

The compounds were dissolved in 0.3% dimethyl sulfoxide solution and then added to potato dextrose agar medium immediately before distributing it into Petri dishes. 5 ml of medium with the compound at the required concentration were distributed into 60 mm sterile Petri dishes. After the medium solidified, each plate was seeded with a 5 mm mycelial disk taken from the peripheral zone of the plate with an actively growing virulent culture. The plates were incubated in growth chambers at 25°C and 70% relative humidity for seven days and then radial growth was measured in comparison with the radial growth of the untreated control. Compounds 68 and 150 at 300 ppm in these trials demonstrated at least 70% control over the untreated group, which showed extensive disease development.

Example 6. Fusarium culmorum (root rot of cereals)

The compounds were dissolved in 0.3% dimethyl sulfoxide solution and then added to potato dextrose agar medium immediately before distributing it into Petri dishes. 5 ml of medium with the compound at the required concentration were distributed into 60 mm sterile Petri dishes. After the medium solidified, each plate was seeded with a 5 mm mycelial disk taken from the peripheral zone of the plate with an actively growing virulent culture. The plates were incubated in growth chambers at 25°C and 60% relative humidity for seven days and then radial growth was measured in comparison with the radial growth of the untreated control. Compound 140 at 300 ppm in these trials demonstrated at least 70% control over the untreated group, which showed extensive disease development.

Example 7: Test of Phakopsora pachyrhizi on soybean

The compounds were dissolved in 2% dimethyl sulfoxide/acetone solution and then mixed with water containing the emulsifier to an exact spray volume of 50 ml. Pour 50 ml of this solution into spray bottles for additional uses.

To test the preventive activity of the compounds, healthy young soybean plants grown in a greenhouse were sprayed with the active compound formulation at the indicated application rates inside spray chambers using hollow cone nozzles. One day after treatment, plants were inoculated with a spore suspension containing 2 × ¹⁰⁵ Phakopsora pachyrhizi conidia . The inoculated plants were then kept in a greenhouse chamber at 22-24°C and 80-90% relative humidity for disease expression.

Visual assessment of the effectiveness of the compounds was carried out by assessing the severity of the disease (scale 0-100%) on the example of treated plants 3, 7, 10 and 15 days after application. The potency (% control) of the compounds was calculated by comparing the extent of disease in the treated plant with that of the untreated control. Sprayed plants were also assessed for plant compatibility by recording symptoms such as necrosis, chlorosis and stunting. Connections 1 2 3 4 5 6 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 33 34 35 36 40 41 42 44 45 46 47 49 50 52 53 54 56 57 58 60 63 64 65 66 67 78 82 83 84 85 86 87 88 94 95 96 98 100 103 135 136 at 500 ppm in these trials demonstrated control of at least 70% compared to the untreated group, which showed extensive disease development.

Having described the present invention with reference to certain preferred aspects, other aspects will become apparent to one skilled in the art in light of the description. It will be apparent to those skilled in the art that many modifications to both materials and methods may be practiced without departing from the scope of the present invention.

Claims (106)

1. Compound of formula (I) where R ¹ represents C ₁ -C ₂ haloalkyl; L ¹ represents a direct connection; L ² represents a direct connection; A is phenyl or pyridyl; and said phenyl or pyridyl is optionally substituted with one or more identical or different R ^A groups; R ^A is selected from the group consisting of hydrogen, halogen, cyano, amino, hydroxy, C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ hydroxyalkyl, C ₃ -C ₈ halocycloalkyl, C ₁ -C ₆ alkoxy and C ₁ -C ₆ haloalkoxy; R ^4b is independently selected from the group consisting of hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy and C ₁ -C ₆ haloalkoxy; R ^2d , R ^3d , R ^2f and R ^3f are independently selected from the group consisting of hydrogen, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; W ¹ represents O; Q represents O, S(=O) _0-2 , S(=O) _0-1 (=NR ^4b ), NR ^4b , -N=S(=NR ^8a )(R ^8b )-; -N=S(=O) _0-1 (R ^8c )-; R ¹⁰ is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₂ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl , C ₂ -C ₆ haloalkynyl, C3-C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, C ₁ -C ₆ alkyl-C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkyl-C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkyl-C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkyl-C ₃ -C ₈ cycloalkyl-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylamino-C ₁ -C ₆ alkyl, di-C ₁ -C ₆ alkylamino-C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkylamino-C ₁ -C ₆ alkyl, C ₂ -C ₆ haloalkoxy- _{C 1} -C ₆ alkyl, C _{1 -C 6 hydroxyalkyl, C 1 -C 6} alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₃ -C ₈ cycloalkylsulfinyl, C ₁ -C ₆ alkylsulfonylamino, C ₁ -C ₆ haloalkylsulfonylamino, C ₁ -C ₆ cyanoalkyl, C ₁ -C ₆ alkoxycarbonyl-C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkyl-C ₁ -C ₆ alkylamino, C ₁ - C ₆ haloalkoxyamino, C ₁ -C ₆ alkylcarbonyl-C ₁ -C ₆ alkylamino, C ₁ -C ₆ haloalkylcarbonyl-C ₁ -C ₆ alkylamino, C ₁ -C ₆ alkoxycarbonyl-C ₁ -C ₆ alkylamino, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkoxycarbonylalkoxy, C ₃ -C ₈ cycloalkyl-C ₁ -C ₆ alkylamino-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkoxycarbonyl, C ₃ -C ₈ halocycloalkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy-C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkoxy-C ₁ -C ₆ haloalkyl, cyano(C ₁ -C ₆ alkoxy)-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxysulfonyl, C ₃ -C ₈ halocycloalkoxycarbonyl, C ₁ -C ₆ alkyl-C ₃ -C ₈ cycloalkylcarbonyl, C ₃ -C ₈ halocycloalkylcarbonyl, -OR ¹² , -NR ¹³ R ¹⁴ , nitro, -SH, -C(=O)R ¹⁵ , -C(=O)OR ¹² , -C(=O)NR ¹³ R ¹⁴ , -NR ¹³ C(=O)R ¹⁵ , -SO ₂ R ¹⁵ , -SO ₂ NR ¹² R ¹³ and Z ¹ Q ¹ ; Z ¹ represents a direct bond, CR ^2d R ^3d , N, O, C(O) or S(O) _0-2 ; Q ¹ is selected from phenyl, benzyl, naphthalene, 5- or 6-membered heteroaromatic ring or 8-11-membered heteroaromatic fused ring system; wherein the heteroatom within the heteroaromatic rings is selected from N, O or S and each ring or ring system may be optionally substituted with one or more R ⁷ groups; or Q ¹ is selected from a 3-7 membered non-aromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered non-aromatic heterocyclic ring or an 8-15 membered non-aromatic fused ring system, where the heteroatom in the non-aromatic rings is selected from N, O or S(O) _0-2 , and the C ring member of non-aromatic carbocyclic or non-aromatic heterocyclic rings or ring systems may be replaced by C(O), and each ring or ring system may be optionally substituted by one or more R ⁷ groups ; R ⁷ is selected from hydrogen, halogen, hydroxy, cyano, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ - C ₆ haloalkoxy, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylamino, di-C ₁ -C ₆ alkylamino or -OR ¹² ; R ^8a , R ^8b and R ^8c are independently selected from hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or C ₁ -C ₆ alkoxy; or R ^4b and R ¹⁰ together with the atoms to which they are attached can form a 3-8 membered heterocyclic ring or ring system, where the heteroatom is selected from the group consisting of N, O and S(O) _0-2 , and a ring member , representing C, of the heterocyclic ring or ring system may be replaced by C(O), and said heterocyclic ring or ring system may be optionally substituted by halogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ - C ₄ alkoxy or C ₁ -C ₄ haloalkoxy; R ¹² is selected from the group consisting of C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₈ cycloalkyl and C ₃ -C ₈ halocycloalkyl; R ¹³ and R ¹⁴ are independently selected from the group consisting of hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, phenyl and a 5- or 6-membered heterocyclic ring; wherein said phenyl, 5- or 6-membered heterocyclic ring may be optionally substituted with halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl and C ₁ -C ₆ alkoxy, or R ¹³ and R ¹⁴ together with the N atom to which they are attached can form a 3-7 membered heterocyclic ring; wherein the heteroatom of the heterocyclic ring is selected from N, O or S(O) _0-2 and the C ring member of the heterocyclic ring may be replaced by C(O), wherein said heterocyclic ring may be optionally substituted by halogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ haloalkyl or C ₁ -C ₆ alkoxy, R ¹⁵ represents hydrogen, hydroxy, halogen, amino, C ₁ -C ₆ alkylamino, di-C ₁ -C ₆ alkylamino, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₃ -C ₈ cycloalkyl, phenyl, 5- or 6-membered heterocyclic ring, wherein said phenyl, 3-6-membered heterocyclic ring may be optionally substituted with halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or C ₁ -C ₆ alkoxy; and its agriculturally acceptable salts. 2. The compound of formula (I) according to claim 1, where R ¹ represents C ₁ -haloalkyl, where halogen represents chlorine or fluorine; R ^A is selected from the group consisting of hydrogen, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy and C ₂ -C ₆ haloalkoxy; Q is O, S(=O) _0-2 , NR ^4b ; R ¹⁰ is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, C ₁ -C ₆ alkyl, C 2 -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C _{1 -C 6} haloalkyl, C ₂ -C ₆ haloalkenyl , C ₂ -C ₆ haloalkynyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, C ₁ -C ₆ alkyl-C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkyl-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylamino-C ₁ -C ₆ alkyl, di-C ₁ -C ₆ alkylamino -C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkylamino-C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkylamino, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ hydroxyalkyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, C ₃ -C ₈ cycloalkylsulfonyl, C ₁ -C ₆ cyanoalkyl, C ₁ -C ₆ haloalkylamino, C ₁ -C ₆ alkoxyamino, C ₂ -C ₆ haloalkoxyamino and Z ¹ Q ¹ . 3. The compound of formula (I) according to claim 1, where R ¹ represents C ₁ -haloalkyl, where halogen represents chlorine or fluorine; R ^A is selected from the group consisting of hydrogen, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl and C ₁ -C ₆ alkoxy; Q represents O, S(=O) _0-2 and NR ^4b ; R ¹⁰ is selected from the group consisting of hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkynyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, C ₁ -C ₆ alkyl-C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkyl-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy , C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylamino, di-C ₁ -C ₆ alkylamino, C ₁ -C ₆ alkylamino-C ₁ -C ₆ alkyl, di-C ₁ -C ₆ alkylamino-C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkylamino, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ hydroxyalkyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, C ₃ -C ₈ cycloalkylsulfonyl, C ₁ -C ₆ cyanoalkyl, C ₁ -C ₆ haloalkylamino, C ₁ -C ₆ alkoxyamino, C ₁ -C ₆ haloalkoxyamino and Z ¹ Q ¹ . 4. A compound of formula (I) according to claim 1, wherein said compound of formula (I) is selected from 2-phenoxy-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl )ethan-1-one; 2-(2-fluorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(4-methoxyphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(4-bromophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(4-chlorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2,6-dichlorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(3-bromo-4-methylphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(3-fluorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(4-fluorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(m-tolyloxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2-methoxyphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(4-bromo-3-fluorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(4-chloro-3-(trifluoromethyl)phenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2,6-dichlorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3-methoxyphenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(3,5-dichlorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2,5-dimethylphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(5-chloro-2-methylphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2,4-difluorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2-chloro-4-fluorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2,4-dichlorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(pyridin-3-yloxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(p-tolylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-methoxyphenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(cyclopentylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(benzo[d]oxazol-2-ylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-methylthiazol-2-yl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3,4-difluorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethyl)phenyl)amino)ethan-1-one; 2-((2-fluorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3-methoxyphenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2-chloro-5-methylphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(p-tolyloxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(3-chlorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-(trifluoromethyl)phenoxy)ethan-1-one; 2-(3-methoxyphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2,4-dimethylphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(o-tolyloxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(3-(trifluoromethyl)phenoxy)ethan-1-one; 2-(3-fluoro-5-methylphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(3-chloro-5-fluorophenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2-chloro-4-methoxyphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2-chloropyridin-4-yl)oxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((6-methyl-3-(trifluoromethyl)pyridin-2-yl)oxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane- 1-she; 2-((2-chloropyridin-3-yl)oxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((6-fluoropyridin-3-yl)oxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((5-bromopyridin-3-yl)oxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((6-bromopyridin-3-yl)oxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((1-methyl-1H-pyrazol-3-yl)oxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 2-((4-chloropyridin-3-yl)oxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3,4-dichlorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-chlorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3-chlorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3,4-difluorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(benzylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-methoxybenzyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((1-phenylethyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(cyclohexylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(phenylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(allylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3-(trifluoromethyl)phenyl)thio)ethan-1-one; 2-((2-methoxyphenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3-fluorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2-fluorophenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(o-tolylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(m-tolylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(pyridin-4-ylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(isopropylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(tert-butylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethyl)phenyl)thio)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethyl)pyrimidin-2-yl)thio)ethan-1-one; 2-(thiazol-2-ylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(pyridin-2-ylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-methyl-4H-1,2,4-triazol-3-yl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl )ethan-1-one; 2-((1,3,4-thiadiazol-2-yl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; 2-((4-chlorophenyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3,4-difluorophenyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(benzylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-methoxybenzyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((1-phenylethyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((5-methylthiazol-2-yl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(phenylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3-(trifluoromethyl)phenyl)sulfinyl)ethan-1-one; 2-(p-tolylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3-fluorophenyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2-fluorophenyl)sulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(o-tolylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(m-tolylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(tert-butylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethyl)phenyl)sulfinyl)ethan-1-one; 2-(isopropylsulfinyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3,4-dichlorophenyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-chlorophenyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3,4-difluorophenyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(benzylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-methoxybenzyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((1-phenylethyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(cyclohexylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((5-methylthiazol-2-yl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(phenylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3-(trifluoromethyl)phenyl)sulfonyl)ethan-1-one; 2-(o-tolylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3-fluorophenyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(isopropylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(thiazol-2-ylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(tert-butylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethyl)phenyl)sulfonyl)ethan-1-one; 2-(m-tolylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2-fluorophenyl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(pyridin-4-ylsulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-hydroxy-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2-fluorophenoxy)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((3-fluorophenyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((4-methoxyphenyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((4-methoxybenzyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-(benzylthio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-(cyclopentylthio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((2,6-dichlorophenyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-(benzo[d]oxazol-2-ylthio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((4-(trifluoromethoxy)phenyl)thio)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((4-methoxyphenyl)sulfonyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((4-methoxybenzyl)sulfonyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-(benzylsulfonyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-(cyclopentylsulfonyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((3-fluorophenyl)sulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((3-fluorophenyl)sulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((4-methoxyphenyl)sulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((4-methoxybenzyl)sulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-(benzylsulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-((2,6-dichlorophenyl)sulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 2-(cyclopentylsulfinyl)-1-(5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)ethan-1-one; 4-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; 2-(4-methylpiperazin-1-yl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-morpholino-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(phenylamino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-fluorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2,4-difluorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-chloro-3-(trifluoromethyl)phenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3-(trifluoromethyl)phenyl)amino)ethan-1-one; 2-((4-chlorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((3-fluorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(m-tolylamino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-methoxyphenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(o-tolylamino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2-methoxyphenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(pyrimidin-2-ylthio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((1H-benzo[d]imidazol-2-yl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 2-((1,3,4-thiadiazol-2-yl)sulfonyl)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 2-((4'-fluoro-[1,1'-biphenyl]-3-yl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl )ethan-1-one; 1-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyrrolidin-2-one; 1-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidin-2-one; 4-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)morpholin-3-one; 1-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)azetidin-2-one; 2-fluoro-N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; N,3-dimethyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyrimidine-5-sulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyridazine-4-sulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)methanesulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyrazine-2-sulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyridine-4-sulfonamide; N,1-dimethyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-1H-pyrazole-4-sulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-1-phenylmethanesulfonamide; 3-(dimethylamino)-N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; 4-chloro-N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; 4-methoxy-N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)ethanesulfonamide; 2,4-difluoro-N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; N,2-dimethyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)propane-2-sulfonamide; 1-cyclopropyl-N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)methanesulfonamide; N,1-dimethyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-1H-imidazole-4-sulfonamide; N-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)isoxazole-4-sulfonamide; 2-fluoro-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; 3-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyrimidine-5-sulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyridazine-4-sulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)methanesulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyrazine-2-sulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyridine-4-sulfonamide; 1-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-1H-pyrazole-4-sulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-1-phenylmethanesulfonamide; 3-(dimethylamino)-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; 4-chloro-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; 4-methoxy-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)ethanesulfonamide; 2,4-difluoro-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzenesulfonamide; 2-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)propane-2-sulfonamide; 1-cyclopropyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)methanesulfonamide; 1-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-1H-imidazole-4-sulfonamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)isoxazole-4-sulfonamide; 2-fluoro-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzamide; 3-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyrimidine-5-carboxamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyridazine-4-carboxamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)acetamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pyrazine-2-carboxamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)isonicotinamide; 1-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-1H-pyrazole-4-carboxamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-2-phenylacetamide; 3-(dimethylamino)-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzamide; 4-chloro-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzamide; 4-methoxy-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)propionamide; 2,4-difluoro-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)benzamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)pivalamide; 2-cyclopropyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)acetamide; 1-methyl-N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)-1H-imidazol-4-carboxamide; N-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)isoxazole-4-carboxamide; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(phenylamino)ethan-1-one; 2-((2-chloro-4-fluorophenyl)amino)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyridin-3-ylamino)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyrimidin-5-ylamino)ethan-1-one; 2-((2-chloro-6-methoxyphenyl)amino)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2,4-dichlorophenyl)amino)ethan-1-one; 2-((2-chloro-4-methoxyphenyl)amino)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(p-tolylamino)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2,4-difluorophenyl)amino)ethan-1-one; 2-((3-chloro-4-(trifluoromethyl)phenyl)amino)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxyphenyl)amino)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2,6-dichlorophenyl)amino)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-fluorophenyl)amino)ethan-1-one; 2-((2-chloro-4-(trifluoromethyl)phenyl)amino)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethoxy)phenyl)amino)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyrimidin-5-ylsulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2,6-dichlorophenyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3,3,3-trifluoropropyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(methylsulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-fluorophenyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyridin-3-yl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(phenylsulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(isopropylsulfonyl)ethan-1-one; 2-((2-chloro-4-(trifluoromethyl)phenyl)sulfonyl)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethoxy)phenyl)sulfonyl)ethan-1-one; 2-((2-chloro-6-methoxyphenyl)sulfonyl)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2,4-difluorophenyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxyphenyl)sulfonyl)ethan-1-one; 2-((3-chloro-4-(trifluoromethyl)phenyl)sulfonyl)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(tert-butylsulfonyl)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2-chloro-4-fluorophenyl)sulfonyl)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2-methoxyethyl)sulfonyl)ethan-1-one; 2-(benzylsulfonyl)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((cyclopropylmethyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(ethylsulfonyl)ethan-1-one; 2-((4-chlorobenzyl)sulfonyl)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methylbenzyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxybenzyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1H-pyrazol-4-yl)methyl)sulfonyl)ethane- 1-she; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1H-imidazol-4-yl)methyl)sulfonyl)ethane- 1-she; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1H-1,2,4-triazol-3-yl) methyl)sulfonyl)ethan-1-one; 2-(((1,2,4-oxadiazol-3-yl)methyl)sulfonyl)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane- 1-she; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((oxazol-4-ylmethyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((isoxazol-4-ylmethyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((thiazol-4-ylmethyl)sulfonyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyrimidin-5-ylthio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2,6-dichlorophenyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3,3,3-trifluoropropyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(methylthio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-fluorophenyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyridin-3-ylthio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(phenylthio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(isopropylthio)ethan-1-one; 2-((2-chloro-4-(trifluoromethyl)phenyl)thio)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethoxy)phenyl)thio)ethan-1-one; 2-((2-chloro-6-methoxyphenyl)thio)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2,4-difluorophenyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxyphenyl)thio)ethan-1-one; 2-((3-chloro-4-(trifluoromethyl)phenyl)thio)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(tert-butylthio)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2-chloro-4-fluorophenyl)thio)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2-methoxyethyl)thio)ethan-1-one; 2-(benzylthio)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((cyclopropylmethyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(ethylthio)ethan-1-one; 2-((4-chlorobenzyl)thio)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methylbenzyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxybenzyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1H-pyrazol-4-yl)methyl)thio)ethane- 1-she; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1H-imidazol-4-yl)methyl)thio)ethane- 1-she; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1H-1,2,4-triazol-3-yl) methyl)thio)ethan-1-one; 2-(((1,2,4-oxadiazol-3-yl)methyl)thio)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane- 1-she; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((oxazol-4-ylmethyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((isoxazol-4-ylmethyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((thiazol-4-ylmethyl)thio)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyrimidin-5-yloxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(2,6-dichlorophenoxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(3,3,3-trifluoropropoxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-methoxyethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-fluorophenoxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyridin-3-yloxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-phenoxyethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-isopropoxyethan-1-one; 2-(2-chloro-4-(trifluoromethyl)phenoxy)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-(trifluoromethoxy)phenoxy)ethan-1-one; 2-(2-chloro-6-methoxyphenoxy)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(2,4-difluorophenoxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-methoxyphenoxy)ethan-1-one; 2-(3-chloro-4-(trifluoromethyl)phenoxy)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(tert-butoxy)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2-chloro-4-fluorophenoxy)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(2-methoxyethoxy)ethan-1-one; 2-(benzyloxy)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(cyclopropylmethoxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-ethoxyethan-1-one; 2-((4-chlorobenzyl)oxy)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methylbenzyl)oxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxybenzyl)oxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-pyrazol-4-yl)methoxy)ethane-1- she; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-imidazol-4-yl)methoxy)ethan-1-one ; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-1,2,4-triazol-3-yl)methoxy )ethan-1-one; 2-((1,2,4-oxadiazol-3-yl)methoxy)-1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(oxazol-4-ylmethoxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(isoxazol-4-ylmethoxy)ethan-1-one; 1-(4-(5-(chlorodifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(thiazol-4-ylmethoxy)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyridin-3-ylthio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxybenzyl)thio)ethan-1-one; 2-((2-chloro-4-(trifluoromethyl)phenyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane- 1-she; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyrimidin-5-ylthio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxyphenyl)thio)ethan-1-one; 2-((2-chloro-4-fluorophenyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 2-(tert-butylthio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-fluorophenyl)thio)ethan-1-one; 2-(benzylthio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methylbenzyl)thio)ethan-1-one; 2-((2,6-dichlorophenyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-chlorobenzyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((2-chloro-6-methoxyphenyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-(trifluoromethoxy)phenyl)thio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1H-imidazol-4-yl)methyl) thio)ethan-1-one; 2-((3-chloro-4-(trifluoromethyl)phenyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane- 1-she; 2-((2,4-difluorophenyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1 H-pyrazol-4-yl)methyl )thio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(phenylthio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((thiazol-4-ylmethyl)thio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((oxazol-4-ylmethyl)thio)ethan-1-one; 2-(((1,2,4-oxadiazol-3-yl)methyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl) phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((isoxazol-4-ylmethyl)thio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(((1-methyl-1H-1,2,4-triazol- 3-yl)methyl)thio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((3,3,3-trifluoropropyl)thio)ethan-1-one ; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(methylthio)ethan-1-one; 2-(ethylthio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(isopropylthio)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((2-methoxyethyl)thio)ethan-1-one; 2-((cyclopropylmethyl)thio)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyridin-3-yloxy)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxybenzyl)oxy)ethan-1-one; 2-(2-chloro-4-(trifluoromethyl)phenoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyrimidin-5-yloxy)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-methoxyphenoxy)ethan-1-one; 2-(2-chloro-4-fluorophenoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(tert-butoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-fluorophenoxy)ethan-1-one; 2-(benzyloxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methylbenzyl)oxy)ethan-1-one; 2-(2,6-dichlorophenoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-chlorobenzyl)oxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2-chloro-6-methoxyphenoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-(trifluoromethoxy)phenoxy)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-imidazol-4-yl)methoxy)ethane -1-she; 2-(3-chloro-4-(trifluoromethyl)phenoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 2-(2,4-difluorophenoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-pyrazol-4-yl)methoxy)ethane -1-she; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-phenoxyethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(thiazol-4-ylmethoxy)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(oxazol-4-ylmethoxy)ethan-1-one; 2-((1,2,4-oxadiazol-3-yl)methoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane -1-she; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(isoxazol-4-ylmethoxy)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-1,2,4-triazol-3 -yl)methoxy)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(3,3,3-trifluoropropoxy)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-methoxyethan-1-one; 2-ethoxy-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-isopropoxyethan-1-one; 1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(2-methoxyethoxy)ethan-1-one; 2-(cyclopropylmethoxy)-1-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyridin-3-yloxy)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methoxybenzyl)oxy)ethan-1-one; 2-(2-chloro-4-(trifluoromethyl)phenoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(pyrimidin-5-yloxy)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-methoxyphenoxy)ethan-1-one; 2-(2-chloro-4-fluorophenoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(tert-butoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-fluorophenoxy)ethan-1-one; 2-(benzyloxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((4-methylbenzyl)oxy)ethan-1-one; 2-(2,6-dichlorophenoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-((4-chlorobenzyl)oxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 2-(2-chloro-6-methoxyphenoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(4-(trifluoromethoxy)phenoxy)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-imidazol-4-yl)methoxy)ethane -1-she; 2-(3-chloro-4-(trifluoromethyl)phenoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one ; 2-(2,4-difluorophenoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-pyrazol-4-yl)methoxy)ethane -1-she; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-phenoxyethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(thiazol-4-ylmethoxy)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(oxazol-4-ylmethoxy)ethan-1-one; 2-((1,2,4-oxadiazol-3-yl)methoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethane -1-she; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(isoxazol-4-ylmethoxy)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-((1-methyl-1H-1,2,4-triazol-3 -yl)methoxy)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(3,3,3-trifluoropropoxy)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-methoxyethan-1-one; 2-ethoxy-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-isopropoxyethan-1-one; 1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-(2-methoxyethoxy)ethan-1-one; 2-(cyclopropylmethoxy)-1-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one; 1-(2-oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperazin-2-one and 4-methyl-1-(2- oxo-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperazin-2-one. 5. The compound according to claim 1, wherein said compound is useful as a fungicide. 6. A composition for the control or prevention of plant diseases, containing an effective amount of a compound of formula (I) according to claim 1 and at least one agrochemically acceptable auxiliary substance. 7. The composition according to claim 6, wherein said composition further contains at least one additional active ingredient. 8. The composition according to claim 6, wherein said composition is applied to the seed and the amount of the compound of formula (I) in said composition is in the range of 0.1 g a.i. up to 10 kg a.i. per 100 kg of seeds. 9. The composition according to claim 6, where the plant disease is caused by rust pathogens selected from the group consisting of Hemileia vastatrix (coffee plant rust), Uromyces appendiculatus/fabae/phaseoli (bean rust), Puccinia spp. (rust species) on various plants selected from P. triticina (brown or leaf rust), P. striiformis (line 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, particularly Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybean. 10. A method for controlling phytopathogenic fungi or preventing damage by them, where the method involves treating fungi or materials, plants, parts of plants, their place of growth, soil or seeds to be protected from fungal infection with an effective amount of at least one compound of formula (I) according to item 1 or composition according to item 6. 11. A method for controlling or preventing infection of plants by phytopathogenic microorganisms of agricultural crops and/or horticultural crops, wherein an effective amount of at least one compound of formula (I) according to claim 1 or a composition according to claim 6 is applied to plant seeds. 12. A method for producing a compound of formula (I) according to claim 1, wherein said method comprises the steps of: a) introducing a protecting group on the carbonyl group of the compound of formula 1 using a suitable protecting agent, which is ethylene glycol, to obtain a compound of formula 2: , where L ¹ represents a direct bond, A represents phenyl and L ² represents a direct bond; b) reacting a compound of formula 2 with hydroxylamine to produce a compound of formula 3: , where L ¹ represents a direct bond, A represents phenyl and L ² represents a direct bond; c) reacting a compound of formula 3 with a suitable carboxylic acid anhydride of formula (a) or a carboxylic acid chloride of formula (b) to obtain a compound of formula 4: , where L ¹ represents a direct bond, A represents phenyl and L ² represents a direct bond; d) deprotecting a compound of formula 4 in the presence of a suitable deprotecting agent to obtain a compound of formula 5: , where L ¹ represents a direct bond, A represents phenyl and L ² represents a direct bond; e) halogenating the compound of formula 5 in the presence of a suitable halogenating agent to obtain the compound of formula 6: , where L ¹ represents a direct bond, A represents phenyl and L ² represents a direct bond; f) reacting a compound of formula 6 with a compound of formula (c) to obtain a compound of formula (I): , where L ¹ represents a direct bond, A represents phenyl, L ² represents a direct bond, X represents Br, O or I and W ¹ represents O; and where R ^2f R ^3f , R ¹ , R ¹⁰ and Q are defined in paragraph 1. 13. A method for synthesizing a compound of formula (I) according to claim 1, wherein said method comprises the steps of: a) reacting a compound of formula 7 with a compound of formula (e) to obtain a compound of formula 8: , where L ¹ represents a direct bond, A represents phenyl or pyridyl, L ² represents a direct bond and X represents Br, O or I; b) reacting a compound of formula 8 with hydroxylamine to produce a compound of formula 9: , where L ¹ represents a direct bond, A represents phenyl or pyridyl and L ² represents a direct bond; c) reacting a compound of formula 9 with a suitable carboxylic acid anhydride of formula (a) or a carboxylic acid chloride of formula (b) to obtain a compound of formula 10: , where L ¹ represents a direct bond, A represents phenyl or pyridyl and L ² represents a direct bond; d) halogenating the compound of formula 10 in the presence of a suitable halogenating agent to obtain the compound of formula 6: , where L ¹ represents a direct bond, A represents phenyl or pyridyl, L ² represents a direct bond and X represents Br, Cl or I; e) reacting a compound of formula 6 with a compound of formula (c) to obtain a compound of formula (I): , where L ¹ represents a direct bond, A represents phenyl or pyridyl, L ² represents a direct bond, X represents Br, Cl or I and W ¹ represents O; and where R ^2f , R ^3f , R ¹ , R ¹⁰ and Q are defined in paragraph 1. 14. A method for synthesizing a compound of formula (I) according to claim 1, wherein said method comprises the steps of: a) reacting a compound of formula 11 with hydroxylamine to produce a compound of formula 12: , where L ¹ represents a direct bond, A represents phenyl or pyridyl and L ² represents a direct bond; b) reacting a compound of formula 12 with a suitable carboxylic acid anhydride of formula (a) or a carboxylic acid chloride of formula (b) to obtain a compound of formula 13: , where L ¹ represents a direct bond, A represents phenyl or pyridyl and L ² represents a direct bond; c) reacting a compound of formula 13 with a suitable oxidizing agent to obtain a compound of formula 14: , where L ¹ represents a direct bond, A represents phenyl or pyridyl and L ² represents a direct bond; d) hydrolyzing the compound of formula 14 in the presence of a suitable hydrolyzing agent to obtain the compound of formula 15: , where L ¹ represents a direct bond, A represents phenyl or pyridyl and L ² represents a direct bond; e) oxidizing the compound of formula 15 in the presence of a suitable oxidizing agent to obtain the compound of formula 16: , where L ¹ represents a direct bond, A represents phenyl or pyridyl and L ² represents a direct bond; f) reacting a compound of formula 16 with a compound of formula (c) to obtain a compound of formula (I): , where L ¹ represents a direct bond, A represents phenyl or pyridyl, L ² represents a direct bond and W ¹ represents O; and where R ^2f , R ^3f , R ¹ , R ¹⁰ and Q are defined in paragraph 1. 15. Compound of formula (B) where R ^1ia is selected from 16. Compound of formula (C) where G is selected from the group consisting of R ^2ia is selected from the group consisting of CH ₂ and O; R ^2ib is selected from the group consisting of methyl and halogen.