Abstract: The present invention relates to novel compound of Formula I, wherein, R1, A1, A2, A3, A4, A5, L1, A, L2 and R2 are as defined in the detailed description. The present invention also relates to a combination or a composition comprising the compound of Formula I.
TITLE: Novel oxadiazoles
FIELD OF THE INVENTION:
The present invention relates to novel oxadiazoles, their N-oxides, metal complexes, isomers, polymorphs and/or the agriculturally acceptable salts thereof and to a process for preparing the same. Further, the present invention relates to a combination and to compositions comprising novel oxadiazoles of the present invention. Still further, the present invention relates to the use of novel oxadiazoles for controlling or preventing phytopathogenic fungi and to a method for controlling or preventing harmful phytopathogenic fungi.
BACKGROUND:
Oxadiazoles have already been disclosed in the literature. For example in JP56065881, JP63162680, JPS6061573, JPS6296480, JPS6051188, JP2005336101, W02005051932, EP3165093, EP3165094, EP3167716, EP3165093, JP2017190296, US4488897, WO2015185485, WO2017055469,
WO2017055473, WO2017076739, W02017076740, W02017081311, W02017085098, W02017085100, W02017093019, WO2017093348, WO2017102006, W02017103219, WO2017103223, WO2017109044, W02017110861, WO2017110862, WO2017110863, WO2017110864, WO2017110865, WO2017111152, WO2017118689, WO2017148797, WO2017157962, WO2017162868, WO2017169893, WO2017174158, WO2017178245, WO2017178549, WO2017198852, WO2017207757, WO2017211649, W02017211650, WO2017211652, WO2017213252, WO2017220485, WO201772247, WO201776742,
WO201776757, WO201776935, W0201781309, W0201781310, WO201781311, WO201781312, WO2018015447, WO2018015449, WO2018015458, W02018056340, WO2018055135,
W02018080859, WO2018118781, WO2018117034, WO2018153730 and WO2018114393, various oxadiazoles have been disclosed.
The oxadiazoles reported in the above literature have disadvantages in certain aspects, such as that they exhibit a narrow spectrum of application, or they do not have satisfactory fungicidal activity, particularly at low application rates.
Therefore, it is an object of the present invention to provide compounds having an improved/enhanced activity and/or a broader activity spectrum against phytopathogenic fungi.
This objective is achieved by the use of novel oxadiazoles of the present invention for controlling or preventing phytopathogenic fungi.
SUMMARY:
The present invention relates to novel oxadiazoles of Formula I.
wherein, R1, A1, A2, A3, A4, A5, L1, A, L2 and R2 are as defined in the detailed description.
The compound of Formula I have now been found to have advantages over the compounds reported in the literature in either of improved fungicidal activity, broader spectrum biological activity, lower application rates, biological or environmental properties, and/or enhanced plant compatibility.
More specifically, the present invention further relates to combinations comprising novel oxadiazoles and at least one further pesticidally active substance for controlling or preventing phytopathogenic fungi which are difficult to control or prevent.
The present invention still further relates to compositions comprising novel oxadiazoles or novel oxadiazoles in combination with further pesticidally active substances.
The present invention still further relates to a method and use of novel oxadiazoles, of combinations or of compositions thereof for controlling and or preventing plant diseases, particularly phytopathogenic fungi.
DETAILED DESCRIPTION:
DEFINITIONS:
The definitions provided herein for the terminologies used in the present disclosure are for illustrative purpose only and in no manner limit the scope of the present invention disclosed in the present disclosure.
As used herein, the terms “comprises”, “comprising”, “includes”, “including”, “has”, “having”, “contains”, “containing”, “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.
The transitional phrase “consisting of’ excludes any element, step or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase “consisting of’ appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.
The transitional phrase “consisting essentially of’ is used to define a composition or method that includes materials, steps, features, components or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term “consisting essentially of’ occupies a middle ground between “comprising” and “consisting of’.
Further, unless expressly stated to the contrary, “or” refers to an inclusive “or” and not to an exclusive “or”. For example, a condition A “or” B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
Also, the indefinite articles “a” and “an” preceding an element or component of the present invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore “a” or “an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.
The term “agronomic” refers to the production of field crops such as for food, feed and fiber and includes the growth of corn, soybeans and other legumes, rice, cereal (e.g., wheat, oats, barley, rye, rice, maize), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone and citrus), small fruit (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives).
The term “nonagronomic” refers to other than field crops, such as horticultural crops (e.g., greenhouse, nursery or ornamental plants not grown in a field), residential, agricultural, commercial and industrial structures, turf (e.g., sod farm, pasture, golf course, lawn, sports field, etc.), wood products, stored product, agro-forestry and vegetation management.
Compounds of the present disclosure may be present either in pure form or as mixtures of different possible isomeric forms such as stereoisomers or constitutional isomers. The various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, and geometric isomers. Any desired mixtures of these isomers fall
within the scope of the claims of the present disclosure. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other isomer(s) or when separated from the other isomer(s). Additionally, the person skilled in the art knows processes or methods or technology to separate, enrich, and/or to selectively prepare said isomers.
The meaning of various terms used in the description shall now be illustrated.
The term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” or -N(alkyl) or alkylcarbonylalkyl or alkylsuphonylamino includes straight-chain or branched C1 to C24 alkyl, preferably C1 to C15 alkyl, more preferably C1 to C10 alkyl, most preferably C1 to C6 alkyl. Non -limiting examples of alkyl include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl,
1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl or the different isomers. If the alkyl is at the end of a composite substituent, as, for example, in alkylcycloalkyl, the part of the composite substituent at the start, for example the cycloalkyl, may be mono- or polysubstituted identically or differently and independently by alkyl. The same also applies to composite substituents in which other radicals, for example alkenyl, alkynyl, hydroxy, halogen, carbonyl, carbonyloxy and the like, are at the end.
The term “alkenyl”, used either alone or in compound words includes straight-chain or branched C2 to C24 alkenes, preferably C2 to C15 alkenes, more preferably C2 to C10 alkenes, most preferably C2 to C6 alkenes. Non-limiting examples of alkenes include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-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, l-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 the different isomers. “Alkenyl” also includes polyenes such as 1 ,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl as a part of a composite substituent, for example haloalkenyl and the like, unless defined specifically elsewhere.
Non-limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 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 the different isomers. This definition also applies to alkynyl as a part of a composite substituent, for example haloalkynyl etc., unless specifically defined elsewhere. The term “alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
The term “cycloalkyl” means alkyl closed to form a ring. Non-limiting examples include cyclopropyl, cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as a part of a composite substituent, for example cycloalkylalkyl etc., unless specifically defined elsewhere.
The term “cycloalkenyl” means alkenyl closed to form a ring including monocyclic, partially unsaturated hydrocarbyl groups. Non-limiting examples include cyclopropenyl, cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as a part of a composite substituent, for example cycloalkenylalkyl etc., unless specifically defined elsewhere.
The term “cycloalkynyl” means alkynyl closed to form a ring including monocyclic, partially unsaturated groups. Non-limiting examples include cyclopropynyl, cyclopentynyl and cyclohexynyl. This definition also applies to cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere.
The term “cycloalkoxy”, “cycloalkenyloxy” and the like are defined analogously. Non limiting examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as a part of a composite substituent, for example cycloalkoxy alkyl etc., unless specifically defined elsewhere.
The term “halogen”, either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Non-limiting examples of “haloalkyl” include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl,
dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl, and 1,1,1-trifluoroprop-2-yl. This definition also applies to haloalkyl as a part of a composite substituent, for example haloalkylaminoalkyl etc., unless specifically defined elsewhere.
The terms “haloalkenyl”, “haloalkynyl” are defined analogously except that, instead of alkyl groups, alkenyl and alkynyl groups are present as a part of the substituent.
The term “haloalkoxy” means straight-chain or branched alkoxy groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1-trifluoroprop-2-oxy. This definition also applies to haloalkoxy as a part of a composite substituent, for example haloalkoxyalkyl etc., unless specifically defined elsewhere.
The term “haloalkylthio” means straight-chain or branched alkylthio groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1- fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2- fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethylthio and 1,1,1-trifluoroprop-2-ylthio. This definition also applies to haloalkylthio as a part of a composite substituent, for example haloalkylthioalkyl etc., unless specifically defined elsewhere.
Non-limiting examples of “haloalkylsulfmyl” include CF3S(O), CCl3S(O), CF3CH2S(O) and CF3CF2S(O). Non-limiting examples of “haloalkylsulfonyl” include CF3S(O)2, CCl3S(O)2, CF3CH2S(O)2 and CF3CF2S(O)2.
The term “hydroxy” means -OH, Amino means -NRR, wherein R can be H or any possible substituent such as alkyl. Carbonyl means -C(=O)- , carbonyloxy means -OC(=O)-, sulfinyl means SO, sulfonyl means S(O)2- The term “alkoxy” used either alone or in compound words included C1 to C24 alkoxy, preferably C1 to C15 alkoxy, more preferably C1 to C10 alkoxy, most preferably C1 to C6 alkoxy. Examples of alkoxy include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-
ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1 ,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy and the different isomers. This definition also applies to alkoxy as a part of a composite substituent, for example haloalkoxy, alkynylalkoxy, etc., unless specifically defined elsewhere.
The term “alkoxyalkyl” denotes alkoxy substitution on alkyl. Non-limiting examples of “alkoxyalkyl” include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2.
The term “alkoxyalkoxy” denotes alkoxy substitution on alkoxy.
The term “alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1 ,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dime thy lbu tylthio , 1-ethylbutylthio, 2-ethylbutylthio, 1 , 1 ,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio and the different isomers.
Halocycloalkyl, halocycloalkenyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylcarbonyl, cycloalkylcarbonyl, haloalkoxylalkyl, and the like, are defined analogously to the above examples.
The term “alkylthioalkyl” denotes alkylthio substitution on alkyl. Non-limiting examples of “alkylthioalkyl” include -CH2SCH2, -CH2SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and CH3CH2SCH2CH2. “Alkylthioalkoxy” denotes alkylthio substitution on alkoxy. The term “cycloalkylalkylamino” denotes cycloalkyl substitution on alkyl amino.
The terms “alkoxyalkoxyalkyl”, “alkylaminoalkyl”, “dialkylaminoalkyl”, “cycloalkylaminoalkyl”, “cycloalkylaminocarbonyl” and the like, are defined analogously to “alkylthioalkyl” or “cycloalkylalkylamino”.
The term “alkoxycarbonyl” is an alkoxy group bonded to a skeleton via a carbonyl group (-CO-). This definition also applies to alkoxycarbonyl as a part of a composite substituent, for example cycloalkylalkoxycarbonyl and the like, unless specifically defined elsewhere.
The term “alkoxy carbonylalkylamino” denotes alkoxy carbonyl substitution on alkyl amino. “Alkylcarbonylalkylamino” denotes alkyl carbonyl substitution on alkyl amino. The terms alkylthioalkoxycarbonyl, cycloalkylalkylaminoalkyl and the like are defined analogously.
Non-limiting examples of “alkylsulfmyl” include methylsulphinyl, ethylsulphinyl, propylsulphinyl, 1-methylethylsulphinyl, butylsulphinyl, 1-methylpropylsulphinyl, 2-methylpropylsulphinyl, 1,1-dimethylethylsulphinyl, pentylsulphinyl, 1-methylbutylsulphinyl, 2-methylbutylsulphinyl, 3-methylbutylsulphinyl, 2,2-dimethylpropylsulphinyl, 1-ethylpropylsulphinyl, hexylsulphinyl, 1,1-dimethylpropylsulphinyl, 1,2-dimethylpropylsulphinyl, 1-methylpentylsulphinyl, 2-methylpentylsulphinyl, 3-methylpentylsulphinyl, 4-methylpentylsulphinyl, 1,1-dimethylbutylsulphinyl, 1,2-dimethylbutylsulphinyl, 1,3-dimethylbutylsulphinyl, 2,2-dimethylbutylsulphinyl, 2,3-dimethylbutylsulphinyl, 3,3-dimethylbutylsulphinyl, 1-ethylbutylsulphinyl, 2-ethylbutylsulphinyl, 1,1,2-trimethylpropylsulphinyl, 1,2,2-trimethylpropylsulphinyl, 1-ethyl-1-methylpropylsulphinyl and 1-ethyl-2-methylpropylsulphinyl and the different isomers. The term “arylsulfmyl” includes Ar-S(O), wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphinyl as a part of a composite substituent, for example haloalkylsulphinyl etc., unless specifically defined elsewhere.
Non-limiting examples of “alkylsulfonyl” include methylsulphonyl, ethylsulphonyl, propylsulphonyl, 1-methylethylsulphonyl, butylsulphonyl, 1-methylpropylsulphonyl, 2-methylpropylsulphonyl, 1,1-dimethylethylsulphonyl, pentylsulphonyl, 1-methylbutylsulphonyl, 2-methylbutylsulphonyl, 3-methylbutylsulphonyl, 2,2-dimethylpropylsulphonyl, 1-ethylpropylsulphonyl, hexylsulphonyl, 1,1-dimethylpropylsulphonyl, 1 ,2-dimethylpropylsulphonyl, 1-methylpentylsulphonyl, 2-methylpentylsulphonyl, 3-methylpentylsulphonyl, 4-methylpentylsulphonyl, 1,1-dimethylbutylsulphonyl, 1,2-dimethylbutylsulphonyl, 1,3-dimethylbutylsulphonyl, 2,2-dimethylbutylsulphonyl, 2,3-dimethylbutylsulphonyl, 3,3-dimethylbutylsulphonyl, 1-ethylbutylsulphonyl, 2-ethylbutylsulphonyl, 1,1,2-trimethylpropylsulphonyl, 1,2,2-trimethylpropylsulphonyl, 1-ethyl-1-methylpropylsulphonyl and 1-ethyl-2-methylpropylsulphonyl and the different isomers. The term “arylsulfonyl” includes Ar-S(O)2, wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphonyl as a part of a composite substituent, for example alkylsulphonylalkyl etc., unless defined elsewhere.
“Alkylamino”, “dialkylamino”, and the like, are defined analogously to the above examples.
The term “carbocycle or carbocyclic” includes “aromatic carbocyclic ring system” and “non-aromatic carbocylic ring system” or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which ring may be aromatic or non-aromatic (where aromatic indicates that the Huckel rule is satisfied and non-aromatic indicates that the Huckel rule is not statisfied).
The term “heterocycle or heterocyclic” includes “aromatic heterocycle or heteroaryl ring system” and “non-aromatic heterocycle ring system” or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which ring may be aromatic or non-aromatic, wherein the heterocycle ring contains at least one heteroatom selected from N, O, S(O)0-2, and or C ring member of the heterocycle may be replaced by C(=O), C(=S), C(=CR*R*) and C=NR*, * indicates integers.
The term “non-aromatic heterocycle” or “non-aromatic heterocyclic” means three- to fifteen-membered, preferably three- to twelve- membered, saturated or partially unsaturated heterocycle containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur: mono, bi- or tricyclic heterocycles which contain, in addition to carbon ring members, one to three nitrogen atoms and/or one oxygen or sulphur atom or one or two oxygen and/or sulphur atoms; if the ring contains more than one oxygen atom, they are not directly adjacent; non-limiting examples oxetanyl, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 1-imidazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-1-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-1-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl,
2.4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, pyrrolinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-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, pyrazynyl, morpholinyl, thiomorphlinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl, 1,2,4-hexahydrotriazin-3-yl, cycloserines, 2,3,4,5-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6-or -7- yl, 3,4,5,6-tetra-hydro[2H]azepin-2- or -3- or -4- or -5- or -6- or-7-yl, 2, 3, 4, 7-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or-7- yl, 2,3,6,7-tetrahydro[1H]azepin-1- or - 2- or -3- or -4- or -5- or -6- or -7- yl, hexahydroazepin-1- or -2- or -3- or -4- yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[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, hexahydroazepin-1- or -2- or -3- or -4- yl, tetra- and hexahydro-1,3- diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl, tetra- and hexahydro-1,3-dioxepinyl, tetra- and hexahydro-1,4-dioxepinyl. This definition also applies to heterocyclyl as a part of a composite substituent, for example heterocyclylalkyl etc., unless specifically defined elsewhere.
The term “heteroaryl” or “aromatic heterocyclic” means 5 or 6-membered, fully unsaturated monocyclic ring system containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur; if the ring contains more than one oxygen atom, they are not directly adjacent; 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom; 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom as ring members, non-limiting examples furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,3,4-triazolyl, tetrazolyl; nitrogen-bonded 5-membered heteroaryl containing one to four nitrogen atoms, or benzofused nitrogen-bonded 5-membered heteroaryl containing one to three nitrogen atoms:
5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms as ring members and in which two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member may be bridged by a buta-1,3-diene-1,4-diyl group in which one or two carbon atoms may be replaced by nitrogen atoms, where these rings are attached to the skeleton via one of the nitrogen ring members, non-limiting examples 1-pyrrolyl, 1-pyrazolyl, 1,2,4-triazol-1- yl, 1-imidazolyl, 1,2,3-triazol-1-yl and 1,3,4-triazol-1-yl.
6-membered heteroaryl which contains one to four nitrogen atoms: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain, respectively, one to three and one to four nitrogen atoms as ring members, non-limiting examples 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl; benzofused 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulphur atom: non-limiting examples indol-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; benzofused 6-membered heteroaryl which contains one to three nitrogen atoms: non-limiting examples quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl and isoquinolin-8-yl.
The term “trialkylsilyl” includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom such as trimethylsilyl, triethylsilyl and t-butyl-dimethylsilyl. “Halotrialkylsilyl” denotes at least one of the three alkyl radicals is partially or fully substituted with halogen atoms which may be the same or different. The term”alkoxytrialkylsilyl” denotes at least one of the three alkyl radicals is substituted with one or more alkoxy radicals which may be the same or different. The term “trialkylsilyloxy” denotes a trialkylsilyl moiety attached through oxygen.
Non-limiting examples of “alkylcarbonyl” include C(=O)CH3, C(=O)CH2CH2CH3 and C(=O)CH(CH3)2- Non-limiting examples of “alkoxycarbonyl” include CH3OC(=O), CH3CH2OC(=O), CH3CH2CH2OC(=O), (CH3)2CH0C(=O) and the different butoxy -or pentoxycarbonyl isomers. Non-limiting examples of “alkylaminocarbonyl” include CH3NHC(=O), CH3CH2NHC(=O), CH3CH2CH2NHC(=O), (CH3)2CHNHC(=O) and the different butylamino -or pentylaminocarbonyl isomers. Non-limiting examples of “dialkylaminocarbonyl” include (CH3)2NC(=O), (CH3CH2)2NC(=O), CH3CH2(CH3)NC(=O), CH3CH2CH2(CH3)NC(=O) and (CH3)2CHN(CH3)C(=O). Non-limiting examples of “alkoxyalkylcarbonyl” include CH3OCH2C(=O), CH3OCH2CH2C(=O), CH3CH2OCH2C(=O), CH3CH2CH2CH2OCH2C(=O) and CH3CH2OCH2CH2C(=O). Non-limiting examples of “alkylthioalkylcarbonyl” include CH3SCH2C(=O), CH3SCH2CH2C(=O), CH3CH2SCH2C(=O), CH3CH2CH2CH2SCH2C(=O) and CH3CH2SCH2CH2C(=O). The term haloalkylsufonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkyl amino and the like are defined analogously
Non-limiting examples of “alkylaminoalkylcarbonyl” include CThNHCH2C(=O), CH3NHCH2CH2C(=O), CH3CH2NHCH2C(=O), CH3CH2CH2CH2NHCH2C(=O) and CH3CH2NHCH2CH2C(=O).
The term “amide” means A-R'C=ONR"-B, wherein R' and R" indicates substituents and A and B indicate any group.
The term “thioamide” means A-R'C=SNR"-B, wherein R' and R" indicates substituents and A and B indicate any group.
The total number of carbon atoms in a substituent group is indicated by the “Ci-Cj” prefix where i and j are numbers from 1 to 21. For example, C1-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH3OCH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2. In the above recitations, when a compound of Formula I is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents. Further, when the subscript m in (R)m indicates an integer ranging from for example 0 to 4 then the number of substituents may be selected from the integers between 0 and 4 inclusive.
When a group contains a substituent which can be hydrogen, then, when this substituent is taken as hydrogen, it is recognized that said group is being un-substituted.
The embodiments herein and the various features and advantageous details thereof are explained with reference to the non-limiting embodiments in the description. Descriptions of well -known components and processing techniques are omitted so as to not unnecessarily obscure the embodiments herein. The examples used herein are intended merely to facilitate an understanding of ways in which the embodiments herein may be practiced and to further enable those of skilled in the art to practice the embodiments herein. Accordingly, the examples should not be construed as limiting the scope of the embodiments herein.
The description of the specific embodiments will so fully reveal the general nature of the embodiments herein that others can, by applying current knowledge, readily modify and/or adapt for various applications such specific embodiments without departing from the generic concept, and, therefore, such adaptations and modifications should and are intended to be comprehended within the meaning and range of equivalents of the disclosed embodiments. It is to be understood that the phraseology or terminology employed herein is for the purpose of description and not of limitation. Therefore, while the embodiments herein have been described in terms of preferred embodiments, those skilled in the art will recognize that the embodiments herein can be practiced with modification within the spirit and scope of the embodiments as described herein.
Any discussion of documents, acts, materials, devices, articles and the like that has been included in this specification is solely for the purpose of providing a context for the disclosure. It is not to be taken as an admission that any or all of these matters form a part of the prior art base or were common general knowledge in the field relevant to the disclosure as it existed anywhere before the priority date of this application.
The numerical values mentioned in the description and the description/claims though might form a critical part of the present invention of the present invention, any deviation from such numerical values shall still fall within the scope of the present invention if that deviation follows the same scientific principle as that of the present invention disclosed in the present invention.
The inventive compound of the present invention may, if appropriate, be present as mixtures of different possible isomeric forms, especially of stereoisomers, for example E and Z, threo and erythro, and also optical isomers, but if appropriate also of tautomers. Both the E and the Z isomers, and also the threo and erythro isomers, and the optical isomers, any desired mixtures of these isomers and the possible tautomeric forms are disclosed and claimed.
The term “pest” for the purpose of the present disclosure includes but is not limited to fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, insects and rodents.
The term “plant” is understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which are protectable and non-protectable by plant breeders’ rights.
For the purpose of the present disclosure the term “plant” includes a living organism of the kind exemplified by trees, shrubs, herbs, grasses, ferns, and mosses, typically growing in a site, absorbing water and required substances through its roots, and synthesizing nutrients in its leaves by photosynthesis.
Examples of “plant” for the purpose of the present invention include but are not limited to agricultural crops such as wheat, rye, barley, triticale, oats or rice; beet, e.g. sugar beet or fodder beet; fruits and fruit trees, such as pomes, stone fruits or soft fruits, e.g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit and citrus trees, such as oranges, lemons, grapefruits or mandarins; any horticultural plants, vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; cucurbitaceae; oleaginous plants; energy and raw material plants, such as cereals, corn, soybean, other leguminous plants, rape, sugar cane or oil palm; tobacco; nuts; coffee; tea; cacao; bananas; peppers; vines (table grapes and grape juice grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, e.g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants.
Preferably, the plant for the purpose of the present invention includes but is not limited to cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and vegetables, ornamentals, any floricultural plants and other plants for use of human and animals.
The term “plant parts” is understood to mean all parts and organs of plants above and below the ground. For the purpose of the present disclosure the term plant parts includes but is not limited to cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots including taproots, lateral roots, root hairs, root apex, root cap, rhizomes, slips, shoots, fruits, fruit bodies, bark, stem, buds, auxillary buds, meristems, nodes and internodes.
The term “locus thereof’ includes soil, surroundings of plant or plant parts and equipment or tools used before, during or after sowing/planting a plant or a plant part.
Application of the compounds of the present disclosure or the compound of the present disclosure in a composition optionally comprising other compatible compounds to a plant or a plant material or locus thereof include application by a technique known to a person skilled in the art which include but is not limited to spraying, coating, dipping, fumigating, impregnating, injecting and dusting.
The term “applied” means adhered to a plant or plant part either physically or chemically including impregnation.
Accordingly, novel oxadiazoles of the present invention are represented by Formula I and include N-oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof.
The present invention relates to a compound of Formula I:
wherein, the substituents and definitions are as defined hereinafter.
R1 is selected from the group consisting of C1-C2-monohaloalkyl, C1-C2-dihaloalkyl, C1-C2-trihaloalkyl, C1-C2-tetrahaloalkyl, and C1-C2-pentahaloalkyl.
In one embodiment R1 is difluoromethyl or trifluoromethyl. In a particular embodiment, R1 is trifluoromethyl.
A1 is C or N. In a particular embodiment, A1 is C.
A2 is C or N.
A3 is C or N. In a particular embodiment, A3 is C.
A4 is C or N.
A5 is C or N.
In some of the embodiments, no more than two of A1, A2, A3, A4, and A5 are nitrogen.
In another embodiment, no more than one of A2, A4, and A5 are nitrogen.
In yet another embodiment, no more than one of A2 and A4 are nitrogen.
In some of the embodiments, A1, A2, A3, A4, and A5 are independently and optionally substituted with one or more RG selected from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl , C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl , and C1-C6-haloalkoxy.
In another embodiment, A1, A2, A3, A4, and A5 are independently and optionally substituted with RG selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, and C1-C6-haloalkoxy.
In a particular embodiment, A1, A2, A3, A4, and A5 are independently and optionally substituted with RG selected from the group consisting of hydrogen, halogen, methyl, ethyl, propyl, isopropyl, methoxy, trifluoro methoxy, trifluoro methyl, difluoro methyl, and cyclopropyl.
Alternatively, two RG together with the atoms to which they are attached may form a 3-, 4-, 5-, or 6-membered carbocyclic ring or ring system or 4-, 5-, or 6- membered heterocyclic ring or ring system; wherein C atom ring members of the carbocyclic or the heterocyclic ring or ring system may be replaced by C(=O) or C(=S); and heteroatom in the heterocyclic ring or ring system is selected from N, O or S(O)0-2; wherein, the carbocyclic or the heterocyclic ring or ring system formed by two RG may optionally further be substituted with one or more of halogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl , C1-C6-alkoxy, and C1-C6-haloalkoxy.
In some of the embodiments, L1 is O, S(=O)0-2, NR6, or
In another embodiment, L1 is O, S(=O)0-2, or NR6.
In a particular embodiment, L1 is O, S, S(=O)2, N-methyl, N-ethyl, N-propyl, N-isopropyl, and N-cyclopropyl.
L1 may be attached to either of A2, A4, or A5.
In some of the embodiments, A is a nitrogen containing 3-, 4-, 5- or 6- membered nonaromatic heterocyclic ring; wherein, ring A additionally may comprise a hetero atom selected from N, O, and S(=O)0-1, wherein, ring A may be optionally substituted with one or more RA.
In another embodiment, A is a nitrogen containing 4-, 5- or 6- membered nonaromatic heterocyclic ring; wherein, ring A may be optionally substituted with one or more RA.
In some embodiments, the substituent RA on A is independently selected from hydrogen, halogen, cyano, nitro, amino, hydroxy, oxo, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-haloalkylsulfinyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylsulfinyl, C1-C6-alkylsuIfonyl, C1-C6-alkylamino, C1-C6-dialkylamino, C3-C8-cycloalkylamino, C1-C6-alkyl-C3-C8-cycloalkylamino, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl, C1-C6-dialkylaminocarbonyl, C1-C6-alkoxycarbonyloxy, C1-C6-alkylaminocarbonyloxy, C1-C6-dialkylaminocarbonyloxy, sulfilimines, sulfoximines, sulfonamide, and sulfonamide.
In another embodiment, the substituent RA on A is independently selected from halogen, cyano,C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, and C3-C8-cycloalkyl.
In a particular embodiment, the substituent RA on A is independently selected from fluorine, bromine, chlorine, iodine, cyano, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, and cyclopropyl.
In some of the embodiments, L2 is (C(=O))1-2, (CR8R9)1-3, S(=O)0-2, NR18, or
In another embodiment, L2is C(=O), (CR8R9), S(=O)2, or NR18.
In a particular embodiment, L2is C(=O), (CH2), (CHCH3), or S(=O)2- Alternatively, RA and R18; or RA and R8 or R9; together with the atom to which they are attached may form a saturated or unsaturated or partially unsaturated 4-, 5-, or 6- membered heterocyclic ring or ring system comprising one or more N; wherein, the heterocyclic ring or ring system may optionally further be substituted with one or more of halogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy , C1-C6-alkylaminocarbonyl, C1-C6-haloalkoxy, -(CR12R13)0-1-C(=O)-NR14R15, -(CR12R13)0-1 -NR14-C(=O)-(C1-C6-alkyl) , -(CR12R13)0-1-NR14-S(=O)0-2-(C1-C6-alkyl), and -(CR12R13)0-1-NR14-C(=O)-NR14;
In some of the embodiments, R2 is selected from hydrogen, halogen, cyano, nitro, amino, hydroxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-hydroxy alkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, aryloxy, heteroaryloxy, C4-C8-heterocyclyloxy, C3-C8-cycloalkyloxy, C1-C6-haloalkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-haloalkylsulfinyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, C4-C8-heterocyclylamino, heteroarylamino, arylamino, C1-C6-dialkylamino, C3-C8-cycloalkylamino, C1-C6-alkyl-C3-C8-cycloalkylamino, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl, C1-C6-dialkylaminocarbonyl, C1-C6-alkoxycarbonyloxy, C1-C6-alkylaminocarbonyloxy, or C1-C6-dialkylaminocarbonyloxy, sulfilimines, sulfoximines, sulfonamide, and sulfinamide; R2 may optionally further be substituted with one or more R7.
In another embodiment, R2 is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-hydroxyalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, aryloxy, heteroaryloxy, C4-C8-heterocyclyloxy, C3-C8-cycloalkyloxy, C1-C6-haloalkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-haloalkylsulfinyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, C4-C8-heterocyclylamino, heteroarylamino, arylamino; R2 may optionally further be substituted with one or more R7.
In a particular embodiment, R2 is selected from hydrogen, C1-C6-alkyl, C3-C8-cycloalkyl, C1-C6-haloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, heteroarylamino, and arylamino; R2 may optionally further be substituted with one or more R7.
In the first alternate embodiment, R2 is phenyl, benzyl, naphthyl, a 5- or 6-membered aromatic ring, an 8- to l1-membered aromatic multi-cyclic ring system, an 8- to l1-membered aromatic fused ring system, a 5- or 6-membered heteroaromatic ring, an 8- to l1-membered heteroaromatic multi-cyclic ring system or an 8- to l1-membered heteroaromatic fused ring system; wherein heteroatom of the heteroaromatic ring or ring system is selected from N, O or S, and each aromatic or heteroaromatic ring or ring system may be optionally substituted with one or more substituents selected from R3.
In another first alternate embodiment, R2 is phenyl, benzyl, a 5- or 6-membered aromatic ring, a 5- or 6-membered heteroaromatic ring; wherein heteroatom of the heteroaromatic ring or ring system is N, and each aromatic or heteroaromatic ring or ring system may be optionally substituted with one or more substituents selected from R3.
In a particular first alternate embodiment, R2 is phenyl, benzyl, a 5- or 6-membered heteroaromatic ring; wherein heteroatom of the heteroaromatic ring or ring system is N, and each aromatic or heteroaromatic ring or ring system may be optionally substituted with one or more substituents selected from R3.
In the second alternate embodiment, R2 is a 3- to 7-membered nonaromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered nonaromatic heterocyclic ring, an 8- to l5-membered nonaromatic multi-cyclic ring system, an 5- to 15 membered spirocyclic ring system, or an 8- to l5-membered nonaromatic fused ring system, wherein, the heteroatom of the nonaromatic heterocyclic ring or ring system is selected from N, O or S(O)0-2, and C ring member of the nonaromatic carbocyclic or nonaromatic heterocyclic ring or ring system may be replaced with C(=O), C(=S), C(=CR20R21) or C(=NR19) and each nonaromatic carbocyclic or nonaromatic heterocyclic ring or ring system may be optionally substituted with one or more substituents selected from R3.
In another second alternate embodiment, R2 is a 3- to 7- membered nonaromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered nonaromatic heterocyclic ring, the heteroatom of the nonaromatic heterocyclic ring or ring system is selected from N, O or S(O)0-2, and each nonaromatic carbocyclic or nonaromatic heterocyclic ring or ring system may be optionally substituted with one or more substituents selected from R3.
In a particular second alternate embodiment, R2 is a 3- to 6- membered nonaromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered nonaromatic heterocyclic ring, the heteroatom of the nonaromatic heterocyclic ring or ring system is selected from N, O or S(O)0-2, and each nonaromatic carbocyclic or nonaromatic heterocyclic ring or ring system may be optionally substituted with one or more substituents selected from R3.
In some of the embodiments, R3 is independently selected from halogen, cyano, nitro, hydroxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkyl-C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C8-cycloalkoxy-C1-C6-alkyl, C1-C6-alkylsuIfinyl-C1-C6-alkyl, C1-C6-alkylsuIfonyl-C1-C6-alkyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-haloalkylamino-C1-C6-alkyl, C3-C8-cycloalkylamino, C3-C8-cycloalkylamino-C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-hydroxyalkenyl, C2-C6-hydroxyalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylcarbonylalkoxy, C1-C6-alkylthio, C1-CVhaloalkylthio, C3-C8-cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonylamino, C1-C6-haloalkylsulfonylamino, C1-C6-a1kylsulfonyloxy, C6-C10-arylsulfonyloxy, C6-C10-arylsulfonyl, C6- C10-arylsulfinyl, C6-C10-arylthio, C1-C6-cyanoalkyl, C1-C6-haloalkylamino, C1-C6-alkoxyamino, C1-C6-haloalkoxyamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylcarbonyl-C1-C6-alkylamino, C2-C6-alkenylthio, di(C1-C6-haloalkyl)amino-C1-C6-alkyl, C1-C6-alkylaminocarbonylamino, di(C1-C6-haloalkyl)amino, sulfilimines, sulfoximines, or SF5; wherein, R3 may be optionally substituted with halogen, cyano, amino, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, and C3-C8-cycloalkyl.
In another embodiment, R3 is independently selected from halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, and C1-C6-haloalkoxy.
In a particular embodiment, R3 is independently selected from halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, and C1-C6-alkoxy.
In some of the embodiments, R7 is selected from C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C4-alkyl, aryloxy, heteroaryloxy, arylamino, heteroarylamino, arylthio, heteroarylthio, C1-C6-hydroxyalkyl , C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylamino-C1-C6-alky1, C1-C6-haloalkoxycarbonyl, and amino-C1-C6-alkyl.
In another embodiment, R7 is selected from halogen, hydroxy, amino, C1-C6-alkyl, and C3-C8-cycloalkyl.
In an alternate embodiment, two R7 together with the atoms to which they are attached may form a 3-, 4-, 5-, or 6- membered carbocyclic ring or ring system or 4-, 5-, or 6- membered heterocyclic ring or ring system; wherein C atom ring members of the carbocyclic or the heterocyclic ring or ring system may be replaced by C(=O) or C(=S); and heteroatom in the heterocyclic ring or ring system is selected from N, O or S; or
In the first alternate embodiment, R7 is phenyl, benzyl, a 5-membered aromatic ring, a 5- or 6-membered heteroaromatic ring; wherein heteroatom of the heteroaromatic ring is selected from N, O or S.
CLAIMS:
1. A compound of Formula I,
wherein,
R1 is selected from the group consisting of C1-C2-monohaloalkyl,C1-C2-dihaloalkyl, C1-C2- trihaloalkyl,C1-C2-tetrahaloalkyl, and C1-C2-pentahaloalkyl;
A1 is C or N;
A2 is C or N;
A3is C or N;
A4 is C or N; and
A5 is C or N; wherein no more than two of A1, A2, A3, A4, and A5 are nitrogen,
wherein, A1, A2, A3, A4, and A5 are independently and optionally substituted with one or more RG selected from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl , C1-C6-alkoxy, C1-C6- alkoxy-C1-C6-alkyl, and C1-C6-haloalkoxy;
L1 is O, S(=O)0-2, NR6, or
wherein, L1 may be attached to either of A2, A4, or A5;
A is a nitrogen containing 3-, 4-, 5- or 6- membered nonaromatic heterocyclic ring; wherein, ring A additionally may comprise a hetero atom selected from N, O, and S(=O)0-2, wherein, ring A may be optionally substituted with one or more RA,
wherein, RA is independently selected from hydrogen, halogen, cyano, nitro, amino, hydroxy, oxo, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1- C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-haloalkenyl, C2-C6- haloalkynyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6- haloalkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-haloalkylsulfinyl, C1-C6- haloalkylsulfonyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, C1-C6- dialkylamino, C3-C8-cycloalkylamino, C1-C6-alkyl-C3-C8-cycloalkylamino, C1-C6- alkylcarbonyl, C1-C6-alkoxycarbonyl , C1-C6-alkylaminocarbonyl, C1-C6- dialkylaminocarbonyl, C1-C6-alkoxycarbonyloxy, C1-C6-alkylaminocarbonyloxy, C1-C6- dialkylaminocarbonyloxy, sulfilimines, sulfoximines, sulfonamide, and sulfinamide;
L2 is (C(=O))1-2, (CR8R9)1-3, S(=O)0-2, NR18, or
wherein, R2 is selected from hydrogen, halogen, cyano, nitro, amino, hydroxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-hydroxy alkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, aryloxy, heteroaryloxy, C4-C8-heterocyclyloxy, C3-C8-cycloalkyloxy, C1-C6-haloalkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-haloalkylsulfinyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, C4-C8-heterocyclylamino, heteroarylamino, arylamino, C1-C6-dialkylamino, C3-C8-cycloalkylamino, C1-C6-alkyl-C3-C8-cycloalkylamino, C1-C6-alkylcarbonyl , C1-C6-alkoxycarbonyl , C1-C6-alkylaminocarbonyl, C1-C6-dialkylaminocarbonyl, C1-C6-alkoxycarbonyloxy, C1-C6-alkylaminocarbonyloxy, or C1-C6-dialkylaminocarbonyloxy, sulfilimines, sulfoximines, sulfonamide, and sulfinamide; R2 may optionally further be substituted with one or more R7; or
R2 is phenyl, benzyl, naphthyl, a 5- or 6-membered aromatic ring, an 8- to l1-membered aromatic multi-cyclic ring system, an 8- to l1-membered aromatic fused ring system, a 5- or 6-membered heteroaromatic ring, an 8- to l1-membered heteroaromatic multi-cyclic ring system or an 8- to ll-membered heteroaromatic fused ring system; wherein heteroatom of the heteroaromatic ring or ring system is selected from N, O or S, and each aromatic or heteroaromatic ring or ring system may be optionally substituted with one or more substituents selected from R3; or
R2 is a 3- to 7-membered nonaromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered nonaromatic heterocyclic ring, an 8- to l5-membered nonaromatic multi-cyclic ring system, an 5- to 15 membered spirocyclic ring system, or an 8- to l5-membered nonaromatic fused ring system, wherein, the heteroatom of the nonaromatic heterocyclic ring or ring system is selected from N, O or S(O)0-2, and C ring member of the nonaromatic carbocyclic or nonaromatic heterocyclic ring or ring system may be replaced with C(=O), C(=S), C(=CR20R21) or C(=NR19) and each nonaromatic carbocyclic or nonaromatic heterocyclic ring or ring system may be optionally substituted with one or more substituents selected from R3,
wherein, R3 is independently selected from halogen, cyano, nitro, hydroxy, C1-C6-alkyl, C2- C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8- cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl- C1-C6-alkyl, C3-C8-cycloalkyl-C3-C8- cycloalkyl, C3-C8-cycloalkenyl, C1-C6-alkoxy-C1-C6-alkyl , C3-C8-cycloalkoxy-C1-C6-alkyl, C1-C6-alkylsulfinyl -C1-C6-alkyl , C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylamino, di-C1- C6-alkylamino, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, C1-C6- haloalkylamino-C1-C6-alkyl, C3-C8-cycloalkylamino, C3-C8-cycloalkylamino-C1-C6-alkyl, C1- C6-alkylcarbonyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-hydroxyalkenyl, C2-C6-hydroxyalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C1-C6- alkylcarbonylalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C1-C6- alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl,C1-C6-haloalkylsulfonyl, C3-C8- cycloalkylsulfonyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonylamino, C1-C6- haloalkylsulfonylamino, C1-C6-alkylsulfonyloxy, C6-C10-alkylsulfonyloxy, C6-C10-arylsulfonyl, C6-C10-arylsulfinyl,C6-C10-arylthio, C1-C6-cyanoalkyl, C1-C6-haloalkylamino, C1-C6- alkoxyamino, C1-C6-haloalkoxyamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylcarbonyl-C1- C6-alkylamino, C2-C6-alkenylthio, di(C1-C6-haloalkyl)amino-C1-C6-alkyl, C1-C6- alkylaminocarbonylamino, di(C1-C6-haloalkyl)amino, sulfilimines, sulfoximines, or SF5; wherein, R3 may be optionally substituted with halogen, cyano, amino, C1-C6-alkyl, C1-C6- alkoxy, C1-C6-alkylthio, and C3-C8-cycloalkyl;
R7 is selected from C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8- cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-Ci-C4-alkyl, aryloxy, heteroaryloxy, arylamino, heteroarylamino, arylthio, heteroarylthio, C1-C6-hydroxyalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6- alkylamino-C1-C6-alky1, C1-C6-haloalkoxycarbonyl, and amino-C1-C6-alkyl; or
R7 is phenyl, benzyl, a 5-membered aromatic ring, a 5- or 6-membered heteroaromatic ring; wherein heteroatom of the heteroaromatic ring is selected from N, O or S; or
R7 is a 3- to 7-membered nonaromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered nonaromatic heterocyclic ring, wherein, the heteroatom of the nonaromatic heterocyclic ring is selected from N, O or S(O)0-2, and C ring member of the nonaromatic carbocyclic or nonaromatic heterocyclic ring may be replaced with C(=O), C(=S), C(=CR22R23), or C(=NR24);
wherein, R7 may be further substituted with one or more R16 on C atom and with one or more R17 on N atom,
R4, R5, R8, R9, R16, R20, R21, R22, and R23 are independently selected from hydrogen, halogen, cyano, nitro, NR10R11,C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4- haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl,C1-C4-alkoxy, C3-C8-cycloalkoxy, or C1-C4-haloalkoxy,
R6, R10, R11, R17, R18, R19, and R24 are independently selected from the group of hydrogen, cyano, hydroxy, NRbRc, (C=O)-Rd, S(O)0-2Re, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-cycloalkyl, phenyl, aryl-C1-C6-alkyl, heteroaryl, hctcroaryl -C1-C6-alkyl , C1-C6-alkylamino, di- C1-C6-alkylamino, tri-C1-C6- alkylamino, or C3-C8-cycloalkyl;
Rb and Rc represent hydrogen, hydroxyl, cyano, amino,C1-C4-alkyl, C1-C4- haloalkyl,C1-C4-alkoxy, C3-C8-cycloalkyl, or C3-C8-halocycloalkyl;
Rd represents hydrogen, hydroxy, halogen, NRbRc, C1-C6-alkyl, C1-C6- haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, or C3-C8- halocycloalkyl; and
Re represents hydrogen, halogen, cyano, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, or C3-C8-halocycloalkyl; or N-oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof, proviso that the following compounds are excluded from the definition of Formula I:
1-[4-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-pyrimidinyl]amino]-1-piperidinyl]- ethanone, (2360451-15-4);
3-[2-chloro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenoxy] -4-hydroxy-4-methyl-1,1-dimethylethyl ester-1-piperidinecarboxylic acid, (2127083-53-6);
3-hydroxy-3-methyl-4-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-pyridinyl]oxy]-1,1-dimethylethyl ester-1-piperidinecarboxylic acid, (2125466-28-4);
N-[1-[(1-methyl-1H-indol-3-yl)methyl]-4-piperidinyl]-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-pyrimidinamine, (1434044-32-2);
N-[1-[(1-methyl-1H-indol-3-yl)methyl]-4-piperidinyl]-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-pyridinamine, (1434044-31-1);
4-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl] -2-pyrimidinyl] amino]-1,1-dimethylethyl ester-1-piperidinecarboxylic acid, (1433958-20-3);
4-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl] -2-pyridinyl] amino]-1,1-dimethylethyl ester-1-piperidinecarboxylic acid, (1433958-19-0);
N-[1-[(1-methyl-1H-indol-3-yl)methyl]-4-piperidinyl]-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-pyrimidinamine, hydrochloride, (1433958-05-4); and
N-[1-[(1-methyl-1H-indol-3-yl)methyl]-4-piperidinyl]-5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-pyridinamine, hydrochloride, (1433958-02-1).
2. The compound of Formula I as claimed in claim 1,
wherein,
R1 is difluoromethyl or trifluoromethyl;
A1 is C;
A2 is C or N;
A3 is C;
A4 is C or N; and
A5 is C or N; wherein no more than one of A2, A4, and A5 are nitrogen,
wherein, A1, A2, A3, A4, and A5 are independently and optionally substituted with one or more RG selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6- alkoxy, C3-C6-cycloalkyl, and C1-C6-haloalkoxy;
L1 is O, S(=O)0-2, or NR6,
wherein, L1 may be attached to either of A2, A4, or A5;
A is a nitrogen containing 4-, 5- or 6- membered nonaromatic heterocyclic ring; wherein, ring A may be optionally substituted with one or more RA,
wherein, RA is independently selected from halogen, cyano,C1- G, -alkyl, C2-C6-alkenyl, C2- C6-alkynyl, C1-C6-alkoxy, and C3-C8-cycloalkyl;
L2 is C(=O), (CR8R9), S(=O)2, or NR18;
wherein, R2 is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-hydroxyalkyl , C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, aryloxy, heteroaryloxy, C4-C8-heterocyclyloxy, C3-C8-cycloalkyloxy, C1-C6-haloalkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-haloalkylsulfinyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl , C1-C6-alkylamino, C4-C8-heterocyclylamino, heteroarylamino, and arylamino; R2 may optionally further be substituted with one or more R7; or
R2 is phenyl, benzyl, a 5- or 6-membered aromatic ring, a 5- or 6-membered heteroaromatic ring; wherein heteroatom of the heteroaromatic ring or ring system is N, and each aromatic or heteroaromatic ring or ring system may be optionally substituted with one or more substituents selected from R3; or
R2 is a 3- to 7- membered nonaromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered nonaromatic heterocyclic ring, the heteroatom of the nonaromatic heterocyclic ring or ring system is selected from N, O or S(O)0-2, and each nonaromatic carbocyclic or nonaromatic heterocyclic ring or ring system may be optionally substituted with one or more substituents selected from R3,
wherein, R3 is independently selected from halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2- C6-haloalkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, and C1-C6-haloalkoxy;
R7 is selected from halogen, hydroxy, amino, C1-C6-alkyl, and C3-C8-cycloalkyl; or
R7 is phenyl, benzyl, a 5-membered aromatic ring, a 5- or 6-membered heteroaromatic ring; wherein heteroatom of the heteroaromatic ring is selected from N, O or S; or
R7 is a 3- to 7-membered nonaromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered nonaromatic heterocyclic ring, wherein, the heteroatom of the nonaromatic heterocyclic ring is selected from N;
wherein, R7 may be further substituted with one or more R16 on C atom and with one or more R17 on N atom,
R4, R8, R9 and R16 are independently selected from hydrogen, halogen, cyano, C1-C4- alkyl,C1-C4- haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1C- 4-alkoxy, C3-C8- cycloalkoxy, andC1-C4-haloalkoxy,
R6, R17, and R18 are selected from the group of hydrogen, cyano, (C=O)-Rd, S(O)0-2Re, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, and C3-C6-cycloalkyl;
Rd represents hydrogen, hydroxy, halogen, NRbRc, C1-C6-alkyl, C1-C6- haloalkyl, C1-C6-alkoxy, or C3-C8-cycloalkyl;
Rb and Rc represent hydrogen,C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, or C3-C8-cycloalkyl; and
Re represents hydrogen, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, or C3-C8-cycloalkyl;
or N-oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof.
3. The compound of Formula I as claimed in claim 1,
wherein,
R1 is trifluoromethyl;
A1 is C;
A2 is C or N;
A3 is C;
A4 is C or N; and
A5 is C; wherein no more than one of A2 & A4 are nitrogen,
wherein, A1, A2, A3, A4, and A5 are independently and optionally substituted with one or more RG selected from the group consisting of hydrogen, halogen, methyl, ethyl, propyl, isopropyl, methoxy, trifluoro methoxy, trifluoro methyl, difluoro methyl, and cyclopropyl;
L1 is O, S, S(=O)2, N-methyl, N-ethyl, N-propyl, N-isopropyl and N-cyclopropyl,
wherein, L1 may be attached to either of A2, A4 or A5;
A is a nitrogen containing 4-, 5- or 6- membered nonaromatic heterocyclic ring; wherein, ring A may be optionally substituted with one or more RA,
wherein, RA is independently selected from fluorine, bromine, chlorine, iodine, cyano, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy and cyclopropyl;
L2 is C(=O), (CH2), (CHCH3), or S(=O)2;
wherein, R2 is selected from hydrogen, C1-C6-alkyl, C3-C8-cycloalkyl, C1-C6-haloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, heteroarylamino, arylamino; R2 may optionally further be substituted with one or more R7; or
R2 is phenyl, benzyl, a 5- or 6-membered heteroaromatic ring; wherein heteroatom of the heteroaromatic ring or ring system is N, and each aromatic or heteroaromatic ring or ring system may be optionally substituted with one or more substituents selected from R3; or
R2 is a 3- to 6- membered nonaromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered nonaromatic heterocyclic ring, the heteroatom of the nonaromatic heterocyclic ring or ring system is selected from N, O or S(O)0-2, and each nonaromatic carbocyclic or nonaromatic heterocyclic ring or ring system may be optionally substituted with one or more substituents selected from R3;
wherein, R3 is independently selected from halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3- C8-cycloalkyl, and C1-C6-alkoxy;
R7 is selected from halogen, hydroxy, amino, C1-C6-alkyl, and C3-C8-cycloalkyl; or
R7 is phenyl, benzyl, a 5-membered aromatic ring, a 5- or 6-membered heteroaromatic ring; wherein heteroatom of the heteroaromatic ring is selected from N, O or S; or
R7 is a 3- to 6-membered nonaromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered nonaromatic heterocyclic ring, wherein, the heteroatom of the nonaromatic heterocyclic ring is selected from N;
wherein, R7 may be further substituted with one or more R16 on C atom and with one or more R17 on N atom;
R16 is independently selected from hydrogen, halogen, cyano,C1-C4-alkyl, C1-C4- haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, C3-C8-cycloalkoxy, and C1-C4-haloalkoxy,
R17 is independently selected from the group of hydrogen, cyano, (C=O)-Rd, S(O)0- 2Re, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, and C3-C6- cycloalkyl;
Rd represents hydrogen, hydroxy, halogen, NRbRc, C1-C6-alkyl, C1-C6- haloalkyl, C1-C6-alkoxy, or C3-C8-cycloalkyl;
Rb and Rc represent hydrogen,C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, or C3-C8-cycloalkyl; and
Re represents hydrogen, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, or C3-C8-cycloalkyl;
or N-oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof.
4. The compound of Formula I is selected from the group consisting of:
(S)-(3-methoxyphenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-1-(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; (S)-(3-bromophenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-4-(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carbonyl)benzonitrile; (S)-2-(3,4-dimethoxyphenyl)-1-(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; (S)-(2-fluorophenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-pyridin-2-yl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-(4-(dimethylamino)phenyl)(3-(4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-cyclobutyl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-(4-methoxyphenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-2-phenyl-1-(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; (S)-pyridin-3-yl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-pyridin-4-yl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-(4-fluorophenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-phenyl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (3-bromophenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)azetidin-1-yl)methanone; (3-methoxyphenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)azetidin-1-yl)methanone; (3-fluorophenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)azetidin-1-yl)methanone; (3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)azetidin-1-yl)(4- (trifluoromethyl)phenyl)methanone; (2-fluorophenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)azetidin-1-yl)methanone; phenyl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)azetidin-1-yl)methanone; 3-(4-((1-(benzylsulfonyl)azetidin-3-yl)oxy)phenyl)-5- (trifluoromethyl)-1,2,4-oxadiazole; tert-butyl (S)-3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxylate; (S)-2-(3-methoxyphenyl)-1-(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; (S)-3-(4-((1-(phenylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(4-((1-((3-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; tert-butyl
(S)-3-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)oxy)pyrrolidine-1-carboxylate; (S)-(2-fluorophenyl)(3-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)oxy)pyrrolidin-1-yl)methanone; (S)-(4-methoxyphenyl)(3-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-
yl)oxy)pyrrolidin-1-yl)methanone; (S)-(3-fluorophenyl)(3-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)oxy)pyrrolidin-1-yl)methanone; (S)-pyridin-3-yl(3-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)oxy)pyrrolidin-1-yl)methanone; (S)-pyridin-4-yl(3-((6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)oxy)pyrrolidin-1-yl)methanone; (S)-3-(4-((1-((2-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(4-((1-((4-methoxyphenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(4-((1-((4-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-(4-(trifluoromethoxy)phenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-N-(2-fluorophenyl)-3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxamide; (S)-N-(4-fluorophenyl)-3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxamide; (S)-N-(4-methoxyphenyl)-3-(4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxamide; (S)-3-(4-((1- (ethylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(4-((1- (cyclopropylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(4-((1-((2,4-difluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-cyclopropyl(3-(4-(5-(tifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-(4-chlorophenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-(2-fluorophenyl)(3-((5-(5-(trilluoromethyl)-1,2,4-oxadiazol-3-yl)pyiidin-2-yl)oxy)pyrrolidin-1-yl)methanone; (S)-(4-methoxyphenyl)(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (S)-(3-fluorophenyl)(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (S)-pyridin-3-yl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (S)-pyridin-4-yl(3-((5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (S)-3-(6-((1-(ethylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-1,1-dimethyl-3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-ium 2,2,2-trifluoroacetate; (S)-(3-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(2-fluorophenyl)methanone; (S)-(3-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(4-methoxyphenyl)methanone; (S)-(3-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(3-fluorophenyl)methanone; (S)-2-(pyridin-2-yl)-1-(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; (S)-(6-methoxypyridin-3-yl)(3-(4-(5-(tifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-pyrimidin-5-yl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-(3-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(pyridin-3-yl)methanone; (S)-(3-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(pyridin-4-yl)methanone; tert-butyl (S)-3-(2-fluoro-4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxylate; (S)-3-(4-((1-
(ethylsulfonyl)pyrrolidin-3-yl)oxy)-3-fluorophenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; tert-butyl (S)-3-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxylate; (S)-(3-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(2-fluorophenyl)methanone; (S)-(3-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(3-fluorophenyl)methanone; (S)-(3-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(pyridin-3-yl)methanone; (S)-(3-(3-fluoro-4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(pyridin-4-yl)methanone; (S)-3-(4-((1-(ethylsulfonyl)pyrrolidin-3-yl)oxy)-2-fluorophenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-1-(3-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; (S)-1-(3-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; tert-butyl (R)-3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidine-1-carboxylate; (R)-3-(6-((1-(phenylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(6-((1-(ethylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(6-((1-((4-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-(2-fluorophenyl)(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (R)-(4-mcthoxyphenyl)(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (R)-3-(6-((1-(cyclopropylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-(3-fluorophenyl)(3-((5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (R)-pyridin-4-yl(3-((5-(5-(tifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (R)-pyridin-3-yl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; tert-butyl 3-(methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)azetidine-1-carboxylate; phenyl(4-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-1-yl)methanone; tert-butyl 4-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidine-1-carboxylate; (3-(methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)azetidin-1-yl)(phenyl)methanone; (3-chlorophenyl)(3-(methyl(4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)azetidin-1-yl)methanone; 1-(3-(methyl(4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)azetidin-1-yl)ethan-1-one; (2-fluorophenyl)(4-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-1-yl)methanone; tert-butyl 3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidine-1-carboxylate; 1-(4-(4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-1-yl)ethan-1-one; (3-fluorophenyl)(3-(methyl(4-(5-(tifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)azetidin-1-yl)methanone; (3-(methyl(4-(5-(tifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)azetidin-1-yl)(p-tolyl)methanone; (4-methoxyphenyl)(3-(methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)azetidin-1-yl)methanone; 1-(3-(methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)azetidin-1-yl)-2-phenylethan-1-one; 1-(3-(methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-
yl)phenyl)amino)azetidin-1-yl)propan-1-one; (3-(methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)azetidin-1-yl)(4-(trifluoromethyl)phenyl)methanone; (4-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-1-yl)(4-(trifluoromethyl)phenyl)methanone; p-tolyl(4-(4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-1-yl)methanone; (S)-3-(6-((1- (phenylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(6-((1-((4-methoxyphenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(6-((1-(cyclopropylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(6-((1-tosylpyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(6-((1-((3-chlorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-5-(trifluoromethyl)-3-(6-((1-((4-(trifluoromethyl)phenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-1,2,4-oxadiazole; (S)-3-(6-((1-(propylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(6-((1-(methylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(6-((1-(m-tolylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-5-(trifluoromethyl)-3-(4-((1- ((trifluoromethyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-1,2,4-oxadiazole; (S)-3-(4-((1- (propylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(4-((1-((4-bromophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(4-((1-(pyridin-3-ylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-5- (trifluoromethyl)-3-(4-((1-((4-(trifluoromethyl)phenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-1,2,4-oxadiazole; (S)-3-(4-((1-tosylpyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(4-((1-((2,4-dichlorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-4-((3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)sulfonyl)benzonitrile; (S)-3-(4-((1-((3-chlorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5- (trifluoromethyl)-1,2,4-oxadiazole; (4-(dimethylamino)phenyl)(3-(methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)azetidin-1-yl)methanone; (4-fluorophenyl)(3-(methyl(4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)azetidin-1-yl)methanone; (2-fluorophenyl)(3-(methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)azetidin-1-yl)methanone; (3-(methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)azetidin-1-yl)(m-tolyl)methanone; tert-butyl 3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxylate; 2,2-dimethyl-1-(3-(methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)azetidin-1-yl)propan-1-one; 2,2-dimethyl-1-(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)propan-1-one; (3-chlorophenyl)(4-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-1-yl)methanone; (2-fluorophenyl)(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (3-fluorophenyl)(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (4-fluorophenyl)(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; p-tolyl(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-
yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-3-(4-((1-(isopropylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(4-((1-benzylpyrrolidin-3-yl)oxy)phenyl)-5- (trifluoromethyl)-1,2,4-oxadiazole; 2-phenyl-1-(4-(4-(5-(trifluoromethyl)- 1,2, 4-oxadiazol-3-yl)phenoxy)piperidin-1-yl)ethan-1-one; 2,2-dimethyl-1-(4-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-1-yl)propan-1-one; (4-methoxyphenyl)(4-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-1-yl)methanone; m-tolyl(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (4-fluorophenyl)(4-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-1-yl)methanone; (3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(4-(trifluoromethyl)phenyl)methanone; (3-chlorophenyl)(3-(3-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; 2-(4-chlorophenyl)-1-(4-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-1-yl)ethan-1-one; (4-methoxyphenyl)(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-3-(4-((1-((3-methylthiophen-2-yl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(4-((1-((1-methyl-1H-imidazol-4-yl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5- (trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(6-((1-((3-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-4-((3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)sulfonyl)benzonitrile; (S)-5-(trifluoromethyl)-3-(6-((1-((3-(trifluoromethyl)phenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-1,2,4-oxadiazole; (S)-3-(6-((1-((2-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(6-((1-(pyridin-3-ylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(6-((1-(benzylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(6-((1-(isopropylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; tert-butyl (R)-3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidine-1-carboxylate; m-tolyl(4-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-1-yl)methanone; (S)-3-(6-((1-((2-chlorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(6-((1-((4-chlorobenzyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(6-((1-((2-methoxyethyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(4-((1-(4-methylbenzyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; N-methyl-1-(phenylsulfonyl)-N-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)azetidin-3-amine; (R)-1-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)ethan-1-one; tert-butyl 3-(methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)pyrrolidine-1-carboxylate; N-methyl-1-tosyl-N-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)azetidin-3-amine; 1-((2-fluorophenyl)sulfonyl)-N-methyl-N-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)azetidin-3-amine; 1-((4-methoxyphenyl)sulfonyl)-N-methyl-N-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)azetidin-3-amine; N-methyl-N-(4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-1-((3-(trifluoromethyl)phenyl)sulfonyl)azetidin-3-amine; (R)-m-tolyl(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; N-methyl-N-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-1-((4- (trifluoromethyl)phenyl)sulfonyl)azetidin-3-amine; 1-((3-chlorophenyl)sulfonyl)-N-methyl-N-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)azeddin-3-amine; (S)-3-(6-((1- (phenethylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-(4-methoxyphenyl)(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; (R)-phenyl(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; (R)-2-phenyl-1-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)ethan-1-one; pyridin-4-yl(4-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-1-yl)methanone; (S)-3-(4-((1-(4-chlorobenzyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(4-((1-isopropylpyrrolidin-3-yl)oxy)phenyl)-5- (trifluoromethyl)-1,2,4-oxadiazole; (R)-2-phenyl-1-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)sulfonyl)pyrrolidin-1-yl)ethan-1-one; (R)-(2-fluorophenyl)(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; (S)-1-(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)ethan-1-one; (S)-1-(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)propan-1-one; (R)-pyridin-4-yl(3-((4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; (R)-2-(4-chlorophenyl)-1-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)ethan-1-one; 2-(4-methoxyphenyl)-1-(4-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-1-yl)ethan-1-one; (R)-2-(4-chlorophenyl)-1-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)sulfonyl)pyrrolidin-1-yl)ethan-1-one; (R)-2-(4-methoxyphenyl)-1-(3-((4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)sulfonyl)pyrrolidin-1-yl)ethan-1-one; (S)-(1-methyl-lH-pyrazol-3-yl)(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (S)-isoxazol-3-yl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (4-(dimethylamino)phenyl)(4-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-1-yl)methanone; N-methyl-1-(propylsulfonyl)-N-(4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)azetidin-3-amine; N-methyl-N-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-1-((trifluoromethyl)sulfonyl)azetidin-3-amine; (R)-(4- (dimethylamino)phenyl)(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; 1-((3-methoxyphenyl)sulfonyl)-N-methyl-N-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)azetidin-3-amine; (S)-oxazol-4-yl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (S)-thiazol-4-yl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; 3-(4-((1-(phenylsulfonyl)azetidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(4-((1-(methylsulfonyl)azetidin-3-yl)oxy)phenyl)-5- (trifluoromethyl)-1,2,4-oxadiazole; 2-(4-methoxyphenyl)-1-(3-((4-(5-(trifluoromethyl)-1,2,4-
oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)ethan-1-one; (R)-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)(4-(trifluoromethyl)phenyl)methanone; (4-chlorophenyl)(4-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-1-yl)methanone; (R)-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)sulfonyl)pyrrolidin-1-yl)(4-(trifluoromethyl)phenyl)methanone; (3-(methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)pyrrolidin-1-yl)(phenyl)methanone; pyridin-2-yl(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; pyridin-4-yl(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; pyridin-3-yl(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-2-methyl-1-(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)propan-1-one; (S)-cyclopropyl(3-((5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (4-chloro-3-(trifluoromethyl)phenyl)(4-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)piperidin-1-yl)methanone; (R)-(3-methoxyphenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-1-(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; (R)-(3-bromophenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-4-(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carbonyl)benzonitrile; (R)-2-(3,4-dimethoxyphenyl)-1-(3-(4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; (R)-(2-fluorophenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-pyridin-2-yl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-(4- (dimethylamino)phenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-cyclobutyl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-(4-methoxyphenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-2-phenyl-1-(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; (R)-pyridin-3-yl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-pyridin-4-yl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-(4-fluorophenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-phenyl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; tert-butyl (R)-3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxylate; (R)-2-(3-methoxyphenyl)-1-(3-(4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; (R)-3-(4-((1- (phenylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(4-((1-((3-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; tert-butyl
(R)-3-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)oxy)pyrrolidine-1-carboxylate; (R)-(2-fluorophenyl)(3-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)oxy)pyrrolidin-1-yl)methanone; (R)-(4-methoxyphenyl)(3-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-
yl)oxy)pyrrolidin-1-yl)methanone; (R)-(3-fluorophenyl)(3-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)oxy)pyrrolidin-1-yl)methanone; (R)-pyridin-3-yl(3-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)oxy)pyrrolidin-1-yl)methanone; (R)-pyridin-4-yl(3-((6-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)oxy)pyrrolidin-1-yl)methanone; (R)-3-(4-((1-((2-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(4-((1-((4-methoxyphenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(4-((1-((4-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-(4-(trifluoromethoxy)phenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-N-(2-fluorophenyl)-3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxamide; (R)-N-(4-fluorophenyl)-3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxamide; (R)-N-(4-methoxyphenyl)-3-(4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxamide; (R)-3-(4-((1- (ethylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(4-((1- (cyclopropylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(4-((1-((2,4-difluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-cyclopropyl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-(4-chlorophenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-(2-fluorophenyl)(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (R)-(4-methoxyphenyl)(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (R)-(3-fluorophenyl)(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (R)-pyridin-3-yl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (R)-pyridin-4-yl(3-((5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (R)-3-(6-((1-(ethylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-1,1-dimethyl-3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-ium 2,2,2-trifluoroacetate; (R)-(3-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(2-fluorophenyl)methanone; (R)-(3-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(4-methoxyphenyl)methanone; (R)-(3-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(3-fluorophenyl)methanone; (R)-2-(pyridin-2-yl)-1-(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; (R)-(6-methoxypyridin-3-yl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-pyrimidin-5-yl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-(3-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(pyridin-3-yl)methanone; (R)-(3-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(pyridin-4-yl)methanone; tert-butyl (R)-3-(2-fluoro-4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxylate; (R)-3-(4-((1-
(ethylsulfonyl)pyrrolidin-3-yl)oxy)-3-fluorophenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; tert-butyl
(R)-3-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxylate; (R)- (3-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(2-fluorophenyl)methanone; (R)-(3-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(3-fluorophenyl)methanone; (R)-(3-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(pyridin-3-yl)methanone; (R)-(3-(3-fluoro-4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(pyridin-4-yl)methanone; (R)-3-(4-((1-(ethylsulfonyl)pyrrolidin-3-yl)oxy)-2-fluorophenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-1-(3-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; (R)-1-(3-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; tert-butyl (S)-3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidine-1-carboxylate;
(S)-3-(6-((1-(phenylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole;
(S)-3-(6-((1-(ethylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-3-(6-((1-((4-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-(2-fluorophenyl)(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (S)-(4-methoxyphenyl)(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (S)-3-(6-((1-(cyclopropylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-(3-fluorophenyl)(3-((5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (S)-pyridin-4-yl(3-((5-(5-(tifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (S)-pyridin-3-yl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (R)-3-(6-((1-(phenylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(6-((1-((4-methoxyphenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(6-((1-(cyclopropylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(6-((1-tosylpyrrolidin-3-yl)oxy)pyridin-3-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(6-((1-((3-chlorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-5-(trifluoromethyl)-3-(6-((1-((4- (trifluoromethyl)phenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-1,2,4-oxadiazole; (R)-3-(6-((1-(propylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(6-((1-(methylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(6-((1-(m-tolylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-5- (trifluoromethyl)-3-(4-((1-((trifluoromethyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-1,2,4-oxadiazole; (R)-3-(4-((1-(propylsulfonyl) pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(4-((1-((4-bromophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(4-((1-(pyridin-3-ylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-5-(trifluoromethyl)-3-(4-((1-((4-(trifluoromethyl)phenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)- 1,2,4-oxadiazole; (R)-3-(4-((1-tosylpyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(4-((1-((2,4-dichlorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-4-((3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)sulfonyl)benzonitrile; (R)-3-(4-((1-((3-chlorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5- (trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(4-((1-(isopropylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5- (trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(4-((1-benzylpyrrolidin-3-yl)oxy)phenyl)-5- (trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(4-((1-((3-methylthiophen-2-yl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(4-((1-((1-methyl- lH-imidazol-4-yl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(6-((1-((3-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-4-((3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)sulfonyl)benzonitrile; (R)-5-(trifluoromethyl)-3-(6-((1-((3- (trifluoromethyl)phenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-1,2,4-oxadiazole; (R)-3-(6-((1-((2-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(6-((1-(pyridin-3-ylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(6-((1-(benzylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole;
(R)-3-(6-((1-(isopropylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; tert-butyl (S)-3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidine-1-carboxylate; (R)-3-(6-((1-((2-chlorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5- (trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(6-((1-((4-chlorobenzyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(6-((1-((2-methoxyethyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(4-((1-(4-methylbenzyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-1-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)ethan-1-one; (S)-m-tolyl(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; (R)-3-(6-((1- (phenethylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (S)-(4-methoxyphenyl)(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; (S)-phenyl(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; (S)-2-phenyl-1-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)ethan-1-one; (R)-3-(4-((1-(4-chlorobenzyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (R)-3-(4-((1-isopropylpyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole;
(S)-2-phenyl-1-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)sulfonyl)pyrrolidin-1-yl)ethan-1-one; (S)-(2-fluorophenyl)(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; (R)-1-(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)ethan-1-one; (R)-1-(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)propan-1-one; (S)-pyridin-4-yl(3-((4-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; (S)-2-(4-chlorophenyl)-1-(3-((4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)ethan-1-one; (S)-2-(4-chlorophenyl)-1-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)sulfonyl)pyrrolidin-1-yl)ethan-1-one; (S)-2-(4-methoxyphenyl)-1-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)sulfonyl)pyrrolidin-1-yl)ethan-1-one; (R)-(1-methyl-1H-pyrazol-3-yl)(3-((5-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (R)-isoxazol-3-yl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (S)-(4-(dimethylamino)phenyl)(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; (R)-oxazol-4-yl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (R)-thiazol-4-yl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (S)-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)(4-(trifluoromethyl)phenyl)methanone; (S)-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)sulfonyl)pyrrolidin-1-yl)(4-(trifluoromethyl)phenyl)methanone; (R)-2-methyl-1-(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)propan-1-one; (R)-cyclopropyl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (3-methoxyphenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; 1-(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; (3-bromophenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; 4-(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carbonyl)benzonitrile; 2-(3,4-dimethoxyphenyl)-1-(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; (2-fluorophenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; pyridin-2-yl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (4-(dimethylamino)phenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; cyclobutyl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (4-methoxyphenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; 2-phenyl-1-(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; pyridin-3-yl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; pyridin-4-yl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (4-fluorophenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; phenyl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; tert-butyl-3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxylate; 2-(3-methoxyphenyl)-1-(3-(4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; 3-(4-((1- (phenylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(4-((1-((3-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; tert-butyl-3-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)oxy)pyrrolidine-1-carboxylate; (2-
fluorophenyl)(3-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)oxy)pyrrolidin-1-yl)methanone; (4-methoxyphenyl)(3-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)oxy)pyrrolidin-1-yl)methanone; (3-fluorophenyl)(3-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)oxy)pyrrolidin-1-yl)methanone; pyridin-3-yl(3-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)oxy)pyrrolidin-1-yl)methanone; pyridin-4-yl(3-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)oxy)pyrrolidin-1-yl)methanone; 3-(4-((1-((2-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(4-((1-((4-methoxyphenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(4-((1-((4-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (4- (trifluoromethoxy)phenyl)(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; N-(2-fluorophenyl)-3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxamide; N-(4-fluorophenyl)-3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxamide; N-(4-methoxyphenyl)-3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxamide; 3-(4-((1-(ethylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(4-((1-(cyclopropylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(4-((1-((2,4-difluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; cyclopropyl(3-(4-(5-(tifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (4-chlorophenyl)(3-(4-(5-(tifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (2-fluorophenyl)(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (4-methoxyphenyl)(3-((5-(5-(tifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (3-fluorophenyl)(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; pyridin-3-yl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; pyridin-4-yl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; 3-(6-((1-(ethylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 1,1-dimethyl-3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-ium 2,2,2-trifluoroacetate; (3-(2-fluoro-4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(2-fluorophenyl)methanone; (3-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(4-methoxyphenyl)methanone; (3-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(3-fluorophenyl)methanone; 2-(pyridin-2-yl)-1-(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; (6-methoxypyridin-3-yl)(3-(4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; pyrimidin-5-yl(3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (3-(2-fluoro-4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(pyridin-3-yl)methanone; (3-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(pyridin-4-yl)methanone; tert-butyl-3-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxylate; 3-(4-((1-(ethylsulfonyl)pyrrolidin-3-yl)oxy)-3-fluorophenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; tert-butyl-3-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxylate; (3-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(2-fluorophenyl)methanone; (3-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(3-fluorophenyl)methanone; (3-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(pyridin-3-yl)methanone; (3-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(pyridin-4-yl)methanone; 3-(4-((1- (ethylsulfonyl)pyrrolidin-3-yl)oxy)-2-fluorophenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 1-(3-(3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; 1-(3-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)ethan-1-one; tert-butyl-3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidine-1-carboxylate; 3-(6-((1-(phenylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(6-((1-(ethylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(6-((1-((4-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (2-fluorophenyl)(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (4-methoxyphenyl)(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; 3-(6-((1-(cyclopropylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (3-fluorophenyl)(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; pyridin-4-yl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; pyridin-3-yl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; 3-(6-((1- (phenylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(6-((1-((4-methoxyphenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(6-((1-(cyclopropylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(6-((1-tosylpyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(6-((1-((3-chlorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 5-(trifluoromethyl)-3-(6-((1-((4-(trifluoromethyl)phenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-1,2,4-oxadiazole; 3-(6-((1-(propylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(6-((1-(methylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(6-((1-(m-tolylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 5-(trifluoromethyl)-3-(4-((1-((trifluoromethyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-1,2,4-oxadiazole; 3-(4-((1-(propylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(4-((1-((4-bromophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(4-((1-(pyridin-3-ylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 5-(trifluoromethyl)-3-(4-((1-((4-(trifluoromethyl)phenyl)sulfonyl)pyrrolidin-3-
yl)oxy)phenyl)-1,2,4-oxadiazole; 3-(4-((1-tosylpyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(4-((1-((2,4-dichlorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 4-((3-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)sulfonyl)benzonitrile; 3-(4-((1-((3-chlorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5- (trifluoromethyl)-1,2,4-oxadiazole; 3-(4-((1-(isopropylsulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5- (trifluoromethyl)-1,2,4-oxadiazole; 3-(4-((1-benzylpyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(4-((1-((3-methylthiophen-2-yl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5- (trifluoromethyl)-1,2,4-oxadiazole; 3-(4-((1-((1-methyl-1H-imidazol-4-yl)sulfonyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(6-((1-((3-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 4-((3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)sulfonyl)benzonitrile; 5-(trifluoromethyl)-3-(6-((1-((3-(trifluoromethyl)phenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-1,2,4-oxadiazole; 3-(6-((1-((2-fluorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(6-((1-(pyridin-3-ylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(6-((1-(benzylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(6-((1-(isopropylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; tert-butyl 3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidine-1-carboxylate; 3-(6-((1-((2-chlorophenyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(6-((1-((4-chlorobenzyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(6-((1-((2-methoxyethyl)sulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(4-((1-(4-methylbenzyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 1-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)ethan-1-one; m-tolyl(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; 3-(6-((1-(phenethylsulfonyl)pyrrolidin-3-yl)oxy)pyridin-3-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; (4-methoxyphenyl)(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; phenyl(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; 2-phenyl-1-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)ethan-1-one; 3-(4-((1-(4-chlorobenzyl)pyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(4-((1-isopropylpyrrolidin-3-yl)oxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 2-phenyl-1-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)sulfonyl)pyrrolidin-1-yl)ethan-1-one; (2-fluorophenyl)(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; 1-(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)ethan-1-one; 1-(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)propan-1-one; pyridin-4-yl(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; 2-(4-chlorophenyl)-1-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)ethan-1-one; 2-(4-chlorophenyl)-1-(3-((4-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)sulfonyl)pyrrolidin-1-yl)ethan-1-one; 2-(4-methoxyphenyl)-1-(3-((4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)sulfonyl)pyrrolidin-1-yl)ethan-1-one; (1-methyl-1H-pyrazol-3-yl)(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; isoxazol-3-yl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (4-(dimethylamino)phenyl)(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)methanone; oxazol-4-yl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; thiazol-4-yl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; (3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)(4-(trifluoromethyl)phenyl)methanone; (3-((4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)sulfonyl)pyrrolidin-1-yl)(4- (trifluoromethyl)phenyl)methanone; 2-methyl-1-(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)propan-1-one; cyclopropyl(3-((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)oxy)pyrrolidin-1-yl)methanone; tert-butyl (R)-3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidine-1-carboxylate; tert-butyl (R)-3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxylate; (R)-2,2-dimethyl-1-(3-(3-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)propan-1-one; (R)-(2-fluorophenyl)(3-(3-(5-(tifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-(3-fluorophenyl)(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-(4-fluorophenyl)(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-p-tolyl(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-m-tolyl(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-(3-(3-(5-(tifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(4-(trifluoromethyl)phenyl)methanone; (R)-(3-chlorophenyl)(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-(4-methoxyphenyl)(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; tert-butyl (R)-3-(methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)pyrrolidine-1-carboxylate; (R)-2-(4-methoxyphenyl)-1-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)ethan-1-one; (R)-(3-(methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)pyrrolidin-1-yl)(phenyl)methanone; (R)-pyridin-2-yl(3-(3-(5-(tifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-pyridin-4-yl(3-(3-(5-(tifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (R)-pyridin-3-yl(3-(3-(5-(tifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; tert-butyl (S)-3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidine-1-carboxylate; tert-butyl (S)-3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidine-1-carboxylate; (S)-2,2-dimethyl-1-(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)propan-1-one; (S)-(2-fluorophenyl)(3-(3-(5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-(3-fluorophenyl)(3- (3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-(4-fluorophenyl)(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-p-tolyl(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-m-tolyl(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)(4- (trifluoromethyl)phenyl)methanone; (S)-(3-chlorophenyl)(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-(4-methoxyphenyl)(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; tert-butyl (S)-3-(methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)pyrrolidine-1-carboxylate; (S)-2-(4-methoxyphenyl)-1-(3-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)thio)pyrrolidin-1-yl)ethan-1-one; (S)-(3-(methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)amino)pyrrolidin-1-yl)(phenyl)methanone; (S)-pyridin-2-yl(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; (S)-pyridin- 4-yl(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone; and (S)-pyridin-3-yl(3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenoxy)pyrrolidin-1-yl)methanone.
5. The compound as claimed in claim 1 in a combination with at least one further pesticidally active substance selected from the group consisting of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertilizers and nutrients.
6. The compound as claimed in claim 1 in a composition comprising at least one agrochemically acceptable auxiliary.
7. The compound as claimed in claim 6, wherein the composition further comprises at least one additional active ingredient.
8. The compound as claimed in claim 1 in a composition applied to seed, wherein the amount of the compound of the formula I is from 0.1 g ai to 10 kg ai per 100 kg of seeds.
9. The compound as claimed in claim 1 used in a method for controlling or preventing phytopathogenic fungi, wherein the method comprises treating the fungi or the materials, plants, plant parts, locus thereof, soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of formula I claimed in claim 1 or the combination claimed in claim 4 or the composition claimed in claim 5.
10. The compound as claimed in claim 1 used in a method for controlling or preventing infestation of plants by phytopathogenic micro-organisms in agricultural crops and or horticultural crops wherein an effective amount of at least one compound of formula I claimed in claim 1 or the
combination claimed in claim 4 or the composition claimed in claim 5, is applied to the seeds of plants.
11. The compound as claimed in claims 1, 5 and 6, for controlling or preventing plant diseases.
12. The compound as claimed in claims 1, 5 and 6, used as fungicides.
13. The compound as claimed in claim 9, wherein the plant diseases are rust pathogens selected from the group consisting of Puccinia spp. (rusts), comprising P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) and P. recondita (brown or leaf rust) on cereals viz., wheat, barley or rye, P. melanocephala on sugarcane; and Phakopsora spp. comprising Phakopsora pachyrhizi and P. meibomiae on soybeans, Hemileia vastatrix (Coffee rust), Uromyces spp., comprising Ufabae (rust of beans).
14. A process for preparing a compound of Formula I, said process comprising the steps of:
a. coupling a compound of Formula VIII and a compound of Formula II to obtain a compound of Formula III,
wherein, L is OH, SH or NHR6: L1 is O, S, or NR6; X is F, Cl, Br, I, OH, SH or NHR6; R6, A1, A2, A3, A4 & A5 are as defined in claim 1;
b. converting the compound of Formula III into a compound of Formula IV,
wherein, L1 is O, S, or NR6; R6, A1, A2, A3, A4 & A5 are as defined in claim 1;
c. cyclizing the compound of Formula IV with a compound of Formula V-a or V-b to obtain a compound of Formula Ia,
wherein, L1 is O, S, or NR6; R6, A1, A2, A3, A4 & A5 are as defined in claim 1;
d. converting the compound of Formula Ia into a compound of Formula VI using a suitable acid,
wherein, L1 is O, S, or NR6; R6, A1, A2, A3, A4 & A5 are as defined in claim 1;
e. reacting the compound of Formula VI with a suitable reactant selected from the group consisting of acid, acyl chloride, sulphonyl chloride, alkyl halide, benzyl halide or amine using suitable base or coupling reagent and a suitable solvent to obtain the compound of Formula I,
wherein, L1 is O, S, or NR6; L2 is (C=O), S(=O)2 and (CR8R9)1-3; R1, R2, R6, A1, A2, A3, A4 & A5 are as defined in claim 1 ;
f. oxidizing a compound of Formula Ib using a suitable oxidizing agent to obtain the compound of Formula I,
wherein, L1a is S; L1 is S(=O) or S(=O)2; R1, R2, A1, A2, A3, A4, A5 & L2 are as defined in claim 1; and
g. converting the compound of Formula Ib into the compound of Formula I using a suitable oxidizing agent and an amine source,
wherein, L1a is S; L1 is
R1, R2, R6, A1, A2, A3, A4, A5 & L2 are as defined in claim 1.
| # | Name | Date |
|---|---|---|
| 1 | 202117012145-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [22-03-2021(online)].pdf | 2021-03-22 |
| 2 | 202117012145-STATEMENT OF UNDERTAKING (FORM 3) [22-03-2021(online)].pdf | 2021-03-22 |
| 3 | 202117012145-PRIORITY DOCUMENTS [22-03-2021(online)].pdf | 2021-03-22 |
| 4 | 202117012145-FORM 1 [22-03-2021(online)].pdf | 2021-03-22 |
| 5 | 202117012145-DECLARATION OF INVENTORSHIP (FORM 5) [22-03-2021(online)].pdf | 2021-03-22 |
| 6 | 202117012145-COMPLETE SPECIFICATION [22-03-2021(online)].pdf | 2021-03-22 |
| 7 | 202117012145-FORM-26 [09-08-2021(online)].pdf | 2021-08-09 |
| 8 | 202117012145-Proof of Right [19-08-2021(online)].pdf | 2021-08-19 |
| 9 | 202117012145.pdf | 2021-10-19 |
| 10 | 202117012145-FORM 18 [22-09-2022(online)].pdf | 2022-09-22 |
| 11 | 202117012145-FER.pdf | 2023-03-22 |
| 12 | 202117012145-PETITION UNDER RULE 137 [22-09-2023(online)].pdf | 2023-09-22 |
| 13 | 202117012145-OTHERS [22-09-2023(online)].pdf | 2023-09-22 |
| 14 | 202117012145-Information under section 8(2) [22-09-2023(online)].pdf | 2023-09-22 |
| 15 | 202117012145-FORM 3 [22-09-2023(online)].pdf | 2023-09-22 |
| 16 | 202117012145-FER_SER_REPLY [22-09-2023(online)].pdf | 2023-09-22 |
| 17 | 202117012145-CLAIMS [22-09-2023(online)].pdf | 2023-09-22 |
| 18 | 202117012145-US(14)-HearingNotice-(HearingDate-03-04-2024).pdf | 2024-03-05 |
| 19 | 202117012145-FORM-26 [01-04-2024(online)].pdf | 2024-04-01 |
| 20 | 202117012145-Correspondence to notify the Controller [01-04-2024(online)].pdf | 2024-04-01 |
| 21 | 202117012145-Written submissions and relevant documents [18-04-2024(online)].pdf | 2024-04-18 |
| 22 | 202117012145-US(14)-ExtendedHearingNotice-(HearingDate-06-05-2025)-1430.pdf | 2025-03-28 |
| 23 | 202117012145-Correspondence to notify the Controller [02-05-2025(online)].pdf | 2025-05-02 |
| 24 | 202117012145-Written submissions and relevant documents [21-05-2025(online)].pdf | 2025-05-21 |
| 25 | 202117012145-PatentCertificate29-05-2025.pdf | 2025-05-29 |
| 26 | 202117012145-IntimationOfGrant29-05-2025.pdf | 2025-05-29 |
| 1 | SearchHistoryE_20-03-2023.pdf |