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Novel Oxadiazole Compounds For Controlling Or Preventing Phytopathogenic Fungi

Abstract: The present invention discloses a compound of formula(I), Formula (I) wherein, R1, L1,A, k, R8, R9L2 and R5 are as defined in the detailed description. The present invention also discloses a process for preparing the compound of formula (I).

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Patent Information

Application #
Filing Date
18 November 2021
Publication Number
14/2022
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
PRABHAKAR@VUTTS.COM
Parent Application

Applicants

PI INDUSTRIES LIMITED
Udaisagar Road 313001 Udaipur-Rajasthan

Inventors

1. BHUJADE, Paras Raybhan
House no- 189, Bhujade Vasti, Apegaon, Taluka-Kopargaon 423603 Ahmednagar - Maharashtra
2. NAIK, Maruti N
Bunder road 6th cross, Hanuman Nagar 581320 Bhatkal - Karnataka
3. TEMBHARE, Nitin Ramesh
At-Mendha, PO-Thanegaon, Tehsil-Tirora 441911 Gondia - Maharashtra
4. AUTKAR, Santosh Shridhar
At Post: Vyala, Taluka: Balapur 444302 Akola - Maharashtra
5. GARG, Ruchi
B 38/47 C-1-K, Tulsipur, Mahmoorganj 221010 Varanasi - UP
6. GADE, Vishwanath
Flat No. 2504, J wing, Rustimjee Azziano, Majiwada, Nasik Road 400601 Thane West - Maharashtra
7. KLAUSENER, Alexander G.M.
Schiffgesweg 18, 50259 Pulheim
8. RAMAKRISHNA, Visannagari
Village-Papireddyguda, Mandal-Keshampet 509216 Rangareddy - Telangana
9. SWARNKAR, Sonali
Near Kailash talkies, Dhamana Road Kapasan- Rajasthan
10. WAGHMARE, Vinod Sunil
At-Navdare, Po-Walchandnagar, Tal-Indapur 413114 Pune - Maharashtra

Specification

The present invention relates to novel oxadiazolecompounds useful for combatingphytopathogenic fungi, a combination thereof and to a composition comprising novel oxadiazole compounds. The present invention also relates to a method for controlling or preventing phytopathogenic fungi.

BACKGROUNDOF THE INVENTION:

Oxadiazoles have already been disclosed in the literature. For example in JPS5665881, JPS63162680, JPS6296480, JPS6051188, W02005051932, EP3165093, EP3167716, EP3165093, W02017076740, W02017102006.W02017110861, WO2017110862, WO2017110864, WO2017157962,

WO2017174158, WO2017198852, WO2017207757, W02017211650, WO2017211652,

WO2017220485, WO2017072247, WO2017076742, WO2017076757, WO2017076935,

WO2018015447, WO2018065414, WO2018118781, WO2018187553 and WO2018202491 various oxadiazoles have been disclosed.

The oxadiazole compounds reported in the above literature have disadvantages in certain aspects, such as that they exhibit a narrow spectrum of application or that 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 using a compound of formula (I) of the present invention for controlling or preventing phytopathogenic fungi.

SUMMARY OF THE INVENTION:

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

wherein, R1, L1,A, k, R8, R9,L2 and Rsare as defined in the detailed description. The present invention also relates to a process for preparing the compound of formula (I).

The compounds of formula (I) have now been found to be advantages over the compounds reported in the literature in either of improved fungicidal efficacy, broader spectrum of biological activity, lower application rates, more favourable biological or environmental properties, or enhanced plant compatibility.

The present invention further relates to a combination comprising the compound of formula (I) of the present invention and at least one further pesticidally active substance for effectively controlling or preventing phytopathogenic fungi which are difficult to combat.

The present invention still further relates to a composition comprising the compound of formula (I) or the compound of formula (I) in combination with a furtherpesticidally active substance.

The present invention still further relates to a method and use of the compound of formula (I), the combination or the composition thereof for controlling and or preventing plant diseases, particularly phtopathogenic fungi.

DETAILED DESCRIPTIONOF THE INVENTION:

DEFINITIONS:

The definitions provided herein for the terminologies used in the present disclosure are for illustrative purpose only and in no manner limit the scope of the present invention disclosed in the present disclosure.

As used herein, the terms “comprises”, “comprising”, “includes”, “including”, “has”, “having”, “contains”,“containing”,“characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.

The transitional phrase“consisting of’ excludes any element, step or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase“consisting of’ appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.

The transitional phrase“consisting essentially of’ is used to define a composition or method that includes materials, steps, features, components or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term“consisting essentially of’ occupies a middle ground between“comprising” and“consisting of’.

Further, unless expressly stated to the contrary,“or” refers to an inclusive“or” and not to an exclusive “or”. For example, a condition A“or” B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).

Also, the indefinite articles“a” and“an” preceding an element or component of the present invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore“a” or“an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.

As referred to in this disclosure, the term“invertebrate pest” includes arthropods, gastropods and nematodes of economic importance as pests. The term“arthropod” includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans. The term“gastropod” includes snails, slugs and other Stylommatophora. The term“nematode” refers to a living organism of the Phylum Nematoda. The term “helminths” includes roundworms, heartworms, phytophagous nematodes (Nematoda), flukes (Tematoda), acanthocephala and tapeworms (Cestoda).

In the context of this disclosure“invertebrate pest control” means inhibition of invertebrate pest development (including mortality, feeding reduction, and/or mating disruption), and related expressions are defined analogously.

The term“agronomic” refers to the production of field crops such as for food, feed and fiber and includes the growth of com, soybeans and other legumes, rice, cereal (e.g., wheat, oats, barley, rye, rice, maize), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone and citrus), small fruit (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives).

The term “nonagronomic” refers to other than field crops, such as horticultural crops (e.g., greenhouse, nursery or ornamental plants not grown in a field), residential, agricultural, commercial and industrial structures, turf (e.g., sod farm, pasture, golf course, lawn, sports field, etc.), wood products, stored product, agro-forestry and vegetation management, public health (i.e. human) and animal health (e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as wildlife) applications.

Nonagronomic applications include protecting an animal from an invertebrate parasitic pest by administering a parasiticidally effective (i.e. biologically effective) amount of a compound of the present invention, typically in the form of a composition formulated for veterinary use, to the animal to be protected. As referred to in the present disclosure and claims, the terms“parasiticidal” and “parasiticidally” refers to observable effects on an invertebrate parasite pest to provide protection of an animal from the pest. Parasiticidal effects typically relate to diminishing the occurrence or activity of the target invertebrate parasitic pest. Such effects on the pest include necrosis, death, retarded growth, diminished mobility or lessened ability to remain on or in the host animal, reduced feeding and inhibition of reproduction. These effects on invertebrate parasite pests provide control (including prevention, reduction or elimination) of parasitic infestation or infection of the animal.

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 Ci to C24 alkyl, preferably Ci to Cis alkyl, more preferably Ci to Cio 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, hydroxyl, 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 Cz to C24 alkenes, preferably Cz to Cis alkenes, more preferably Cz to Cio alkenes, most preferably C2 to C6 alkenes. Non-limiting examples of alkenes include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1 -methyl- 1-propenyl, 2-methyl-l-propenyl, l-methyl-2 -propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl- 1 -butenyl, 2-methyl-1-butenyl, 3-methyl- 1 -butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1 , 1 -dimethyl-2-propenyl, 1, 2-dimethyl- 1-propenyl, l,2-dimethyl-2 -propenyl, 1 -ethyl- 1 -propenyl, 1-ethy-l2 -propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4- hexenyl, 5-hexenyl, 1 -methyl- 1-pentenyl, 2-methyl- 1 -pentenyl, 3-methyl- 1-pentenyl, 4-methyl- 1-pentenyl, l-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, l-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, l,l-dimethyl-3-butenyl, 1 ,2 -dimethyl- 1-butenyl, &,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-l-butenyl, 1,3-dimethyl-2-butenyl, l,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl- 1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-2-butenyl, 1-tihyl- 1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl- 1-butenyl, 2-tihyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl -l-methyl-2-propenyl, 1-ethyl-2-methyl-l-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, l-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, 1 , 1 -dimethyl-2-propynyl, 1 -ethyl -2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1 -methyl-2-pentynyl, l-methyl-3-pentynyl, 1 -methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-l-pentynyl, 3-methyl-4-pentynyl, 4-methyl-l-pentynyl, 4-methyl-2-pentynyl, 1 , 1 -dimethyl-2-butynyl, l,l-dimethyl-3-butynyl, l,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl1,-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. Nonlimiting examples of “haloalkyl” include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1-bromoethyl, 1-fluorotihyl, 2-fluorotihyl, 2,2-difluoroethyl, 2,2,2-trifluorotihyl, 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 chloromtihoxy, bromomethoxy, dichloromethoxy, trichloromtihoxy, fluoromethoxy, difluoromethoxy, trifluoromtihoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromtihoxy, 1-chlorotihoxy, 1-bromoethoxy, 1-fluorotihoxy, 2-fluorotihoxy, 2,2-difluorotihoxy, 2,2,2-trifluorotihoxy, 2-chloro-2-fluorotihoxy, 2-chloro-2,2-difluorotihoxy, 2,2-dichloro-2-fluorotihoxy, 2,2,2-trichlorotihoxy, pentafluorotihoxy and l,l,l-trifluoroprop-2-oxy. This definition also apphes 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-difluorotihylthio, 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 “haloalkylsulfinyl” include CF3S(O), CCl3SC(O), CFsCHzSCO) and CF3CF2S(O). Non-limiting examples of “haloalkylsulfonyl” include CF3S(0)2, CCl3S(0)2, CF3CH2S(0)2 and CF3CF2S(0)2.

The term“hydroxy” means -OH, Amino means -NRR, wherein R can be H or any possible substituent such as alkyl. Carbonyl means -C(=0)-, carbonyloxy means -0C(=0)-, sulfinyl means SO, sulfonyl means S(0)z.

The term“alkoxy” used either alone or in compound words included Ci to C24 alkoxy, preferably Ci to Cis alkoxy, more preferably Ci to Cm alkoxy, most preferably Ci 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 -2- 1-ethyl 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“alkyhhio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1 -methylethylthio, butylthio, 1 -methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1 -methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hexylthio, 1 , 1 -dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1 , 1 -dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1 , 1 ,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1 -ethyl- 1 -methylpropylthio and 1-eth-y2l-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 “alkyhhioalkyl” include -CH2SCH2, -CH2SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and

CH3CH2SCH2CH2. “Alkyhhioalkoxy” denotes alkylthio substitution on alkoxy. The term “cycloalkylalkylamino” denotes cycloalkyl substitution on alkyl amino.

The terms“alkoxyalkoxyalkyl”, “alkylaminoalkyl”, “dialkylaminoalkyl”,“cycloalkylaminoalkyl”, “cycloalkylaminocarbonyl” and the like, are defined analogously to “alkylthioalkyl” or “cycloalkylalkylamino”.

The term“alkoxycarbonyl” is an alkoxy group bonded to a skeleton via a carbonyl group (-CO-). This definition also applies to alkoxycarbonyl as a part of a composite substituent, for example cycloalkylalkoxycarbonyl and the like, unless specifically defined elsewhere.

The term “alkoxycarbonylalkylamino” denotes alkoxy carbonyl substitution on alkyl amino. “Alkylcarbonylalkylamino” denotes alkyl carbonyl substitution on alkyl amino. The terms alkylthioalkoxycarbonyl, cycloalkylalkylaminoalkyl and the like are defined analogously.

Non-limiting examples of“alkylsulfinyl” include methylsulphinyl, ethylsulphinyl, propylsulphinyl, 1-methylethylsulphinyl, butylsulphinyl, 1-methylpropylsulphinyl, 2-methylpropylsulphinyl, 1,1-dimethylethylsulphinyl, pentylsulphinyl, 1 -methylbutylsulphinyl, 2-methylbutylsulphinyl, 3-methylbutylsulphinyl, 2,2-dimethylpropylsulphinyl, 1 -ethylpropylsulphinyl, hexylsulphinyl, 1,1-dimethylpropylsulphinyl, 1 ,2-dimethylpropylsulphinyl, 1 -methylpentylsulphinyl, 2-methylpentylsulphinyl, 3-methylpentylsulphinyl, 4-methylpentylsulphinyl, 1,1-dimethylbutylsulphinyl, 1 ,2-dimethylbutylsulphinyl, 1,3-dimethylbutylsulphinyl, 2,2-dimethylbutylsulphinyl, 2,3-dimethylbutylsulphinyl, 3,3-dimethylbutylsulphinyl, 1-ethylbutylsulphinyl, 2-ethylbutylsulphinyl, 1 , 1 ,2-trimethylpropylsulphinyl, 1,2,2-trimethylpropylsulphinyl, 1 -ethyl- 1 -methylpropylsulphinyl and 1 -ethyl-2-methylpropylsulphinyl and the different isomers. The term“arylsulfinyl” includes Ar-S(O), wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphinyl as a part of a composite substituent, for example haloalkylsulphinyl etc., unless specifically defined elsewhere.

Non-limiting examples of“alkylsulfonyl” include methylsulphonyl, ethylsulphonyl, propylsulphonyl, 1 -methylethylsulphonyl, butylsulphonyl, 1-methylpropylsulphonyl, 2-methylpropylsulphonyl, 1,1-dimethylethylsulphonyl, pentylsulphonyl, 1 -methylbutylsulphonyl, 2-methylbutylsulphonyl, 3-methylbutylsulphonyl, 2,2-dimethylpropylsulphonyl, 1 -ethylpropylsulphonyl, hexylsulphonyl, 1,1-dimethylpropylsulphonyl, 1,2-dimethylpropylsulphonyl, 1-methylpentylsulphonyl, 2-methylpentylsulphonyl, 3-methylpentylsulphonyl, 4-methylpentylsulphonyl, 1,1-dimethylbutylsulphonyl, 1,2-dimethylbutylsulphonyl, 1,3-dimethylbutylsulphonyl, 2,2-dimethylbutylsulphonyl, 2,3-dimethylbutylsulphonyl, 3,3-dimethylbutylsulphonyl, 1-ethylbutylsulphonyl, 2-ethylbutylsulphonyl, 1 , 1 ,2-trimethylpropylsulphonyl, 1,2,2-trimethylpropylsulphonyl, 1 -ethyl- 1-methylpropylsulphonyl and 1-et-2h-yml ethylpropylsulphonyl and the different isomers. The term“arylsulfonyl” includes Ar-S(0)2, wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphonyl as a part of a composite substituent, for example alkylsulphonylalkyl etc., unless defined elsewhere.

“Alkylamino”,“dialkylamino”, and the like, are defined analogously to the above examples.

The term“carbocycle or carbocyclic” includes“aromatic carbocyclic ring system” and“non-aromatic carbocylic ring system” or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which ring may be aromatic or non-aromatic (where aromatic indicates that the Huckel rule is satisfied and non-aromatic indicates that the Huckel rule is not statisfied).

The term‘¾eterocycle or heterocyclic” includes“aromatic heterocycle or heteroaryl ring system” and “non-aromatic heterocycle ring system” or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which ring may be aromatic or non-aromatic, wherein the heterocycle ring contains at least one heteroatom selected from N, O, S(0)o-z, and or C ring member of the heterocycle may be replaced by C(=0), C(=S), C(=CR*R*) and C=NR*, * indicates integers.

The term“non-aromatic heterocycle” or “non-aromatic heterocyclic” means three- to fifteen-membered, preferably three- to twelve- member ed, 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 -tetr ahydrofur any 1, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 1-imidazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, l,2,4-oxadiazolidin-5-yl, l,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-l-yl, l,2,4-triazolidin-3-yl, l,3,4-oxadiazolidin-2-yl, l,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-l-yl, l,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, pyrrolinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3 -isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-l-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3 ,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-l-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-

yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, pyrazynyl, morpholinyl, thiomorphlinyl, l,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5 -hexahydropyrimidiny 1, 2-piperazinyl, l,3,5-hexahydrotriazin-2-yl, 1,2,4-hexahydrotriazin-3-yl, cycloserines, 2,3,4,5-tetrahydro[lH]azepin-l- or -2- or -3- or -4- or -5- or -6-or -7- yl, 3,4,5,6-tetra-hydro[2H]azepin-2- or -3- or -4- or -5- or -6- or-7-yl, 2, 3,4,7-tetrahydro[lH]azepin-l- or -2- or -3- or -4- or -5- or -6- or-7- yl, 2,3,6,7-tetrahydro[lH]azepin-l- or -2- or -3- or -4- or -5- or -6- or -7- yl, hexahydroazepin-1- or -2- or -3- or -4- yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[lH]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, 2,3 ,4,7 -tetrahydro[ 1 H] oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, 2,3,6,7-tetrahydro[lH]oxepin-2-or -3- or -4- or -5- or -6- or -7- yl, hexahydroazepin-1- or -2- or -3- or -4- yl, tetra- and hexahydro-1,3-diazepinyl, tetra- and hexahydro-l,4-diazepinyl, tetra- and hexahydro-l,3-oxazepinyl, tetra- and hexahydro- 1 ,4-oxazepinyl, tetra- and hexahydro-l,3-dioxepinyl, tetra- and hexahydro-l,4-dioxepinyl. This definition also applies to heterocyclyl as a part of a composite substituent, for example heterocyclylalkyl etc., unless specifically defined elsewhere.

CLAIMS:

1) A compound offormula (I),

wherein,

R1 is Ci-Cz-haloalkyl;

L1 is a direct bond, -CR2R3-, -C(=W')-, -CR2R3C(=W1)-, -O, -S(=0)o-2-, or -NR4*-; wherein, the expression at the start and the end of the group indicates the point of attachment to either oxadiazole ring or A;

W1 is O or S;

A is a fused heterobicyclic ring having N at one or more bridgehead; wherein said ring is optionally substituted with one or more identical or different groupsof RA;

RA is selected from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy, SF5, 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, Cz- 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, and 3- to 6- membered carbocyclic or hetCTOcyclic ring, wherein, said 3- to 6- membered carbocyclic or heterocyclic ring may be optionally substituted with one or more identical or different substituents selected fromthe group consisting of halogen, cyano, nitro, hydroxy, Ci- C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, Ci- C6-haloalkyl, C1-C6-alkoxyalkyl, C1-C6-hydroxyalkyl, C2-C6-haloalkenyl, C2-C6- haloalkynyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-haloalkylsulfinyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylsulfinyl, C1-C6- alkylsulfonyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C3-C6-cycloalkylamino, C1-C6- alkyl-C3-C6-cycloalkylamino, C1-C6 alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-

alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkoxycarbonyloxy, C1-C6- alkylaminocarbonyloxyand di-C1-C6-alkylaminocarbonyloxy;

L2 is a direct bond or is selected from the group consisting of -C(=0)-, -C(=S)-, -0-, -S(=0)o-2-, -

5

Y is a direct bond or -NR10-, or -0-, or -S(0)0-2-or -C(=NOR11)-;

k is an integer ranging from 0 to 4; expressions “#” and indicate point of attachments;

W2is O or S;

L3 is a direct bond or is selected from the group consisting of

R10is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2- C6-alkynyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, Cs-C6-cycloalkyl- C1-C6-alkyl, phenyl-C1-C6-alkyl, phenyl, pyridinyl, C(=0)-(Ci-C6-alkyl), C(=0)-(Ci- C6-alkoxy) and -N(R10a)2-; wherein, R10ais independently selected from the group consisting of hydrogen, hydroxyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6- cycloalkyl, C3-C6-cycloalkeny,C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl and C1-C6- alkylthio; each group ofR 10isoptionally substituted with identical or different radical selected from the group consisting of halogen, hydroxy, oxo, cyano, C1-C6-alkyl, Ci- C6-alkoxy and C3-C6-cycloalkyl;

R11isselected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C1-C6-alkylthio, C3- Cg-cycloalkenyl, phenyl-C1-C6-alkyl, heteroaryl-C1-C6- alkyl, phenyl and naphthyl;

R12is selected from the group consisting of hydrogen, NRgRh, wherein, Rg and Rhare independently selected from the group consisting of hydrogen, hydroxyl, cyano, Ci-

R12may optionally be substituted with one or more identical or different substituents selected firomthe group consisting ofhydrogen, halogen, cyano, nitro, hydroxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cg-C6-cycloalkyl, Cg-C6-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6- hydroxyalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Cg-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-haloalkylsulfinyl, C1-C6-haloalkylsulfonyl, C1-C6- alkylsulfmyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C3-C8-cycloalkylamino, C1-C6-alkyl-C3-C8-cycloalkylamino, C1-C6- alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl, di-C1-C6- alkylaminocarbonyl, C1-C6-alkoxycarbonyloxy, C1-C6- alkylaminocarbonyloxy, diC1-C6-alkylaminocarbonyloxy, 5- to 11- membered spirocyclic ring, and 3- to 6- membered carbocyclic or heterocyclic ring;

R8and R9are independently selected from the group consisting of hydrogen, halogen, cyano, Ci-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C1-C6-alkylthio, C3-C8-cycloalkenyl, phenyl-C1-C6-alkyl, heteroaryl-C1-C6-alkyl, phenyl, naphthyl and a 3- to 10- membered saturated, partially unsaturated or aromatic mono- or bicyclic carbocyclic ring or heterocyclic ring, wherein the ring members of the heteroaryl of the heteroaryl-C1-C6-alkyl and the heterocyclic ring include C, N, O and S(0)o-zand the C ring members of the carbocylic ring or the heterocyclic ring may be replaced by one or more C(=0) and C(=S); and wherein R8and R9are independently unsubstituted or substituted with one or more identical or different R8aorR9a; wherein R8aandR9a areselected from the group consisting of halogen, cyano, nitro, hydroxyl,

sulfanyl, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, Ci-C6-haloalkylthio,C3-C8-cycloalkyl,amino-Ci-C6-alkyl, di-C1-C6-alkylamino, NHSOz-C1-C6-alkyl, -C(=0)-Ci-C6-alkyl, C(=0)-C1-C6-alkoxy, C1-C6-alkylsulfonyl, hydroxy-C1-C6-alkyl, -C(=0)-NH2, C(=0)-NH(Ci-C6-alkyl), Ci-C6-alkylthio-Ci-C6-alkyl, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, aminocarbonyl-C1-C6-alkyl andC1-C6-alkoxy-C1-C6-alkyl; or

R8 and R9 together with the atoms to which they are bound form C(=0) or a vinyl group or a saturated, monocyclic 3- to 7-member ed heterocyclicring or carbocyclic ring, wherein the ring members of heterocyclic includeC, N, O and S(0)o-z; and wherein the vinyl group, the heterocyclic ring or the carbocyclic ring is unsubstituted or substituted with one or more identical or different R8b, whereinR8b is selected from the group consisting of halogen, cyano, nitro, hydroxyl, sulfanyl, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, Ci-C6-haloalkylthio,C3-C8-cycloalkyl, SOz-C1-C6-alkyl, NHSOz-C1-C6-alkyl, -C(=0)-C1-C6-alkyl, C(=0)-C1-C6-alkoxy, C1-C6-alkylsulfonyl, SO2-C6H4CH3 and SOz-aryl;

R5 is selected from the group consisting ofhydrogen,Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkyl-C3-C8-cycloalkyl, C3-C8-halocycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, C3-C8-cycloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkyl-C1-C6-thioalkyl, 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, C3-C8-halocycloalkoxy, C3-C8-cycloalkyl-C 1 -C6-alkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, Cz-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, 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, tri-C1-C6-alkylsilyl, C1-C6-alkylsulfonylamino, C1-C6-haloalkylsulfonylamino, C1-C6-alkylcarbonylthio, C1-C6-alkylsulfonyloxy, C1-C6-alkylsulfinyloxy, C6-C10-arylsulfonyloxy, C6-C10-arylsulfinyloxy, C6-C10-arylsulfonyl, C6-C10-arylsulfinyl, C6-C10-arylthio, C1-C6-cyanoalkyl, C2-C6-alkenylcarbonyloxy, C1-C6-alkoxy-C1-C6-alkylthio, C1-C6-alkylthio-C1-C6-alkoxy, C2-C6-haloalkenylcarbonyloxy, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxy-C2-C6-alkynyl, C2-C6-alkynylthio, C3-C8-halocycloalkylcarbonyloxy, C2-C6-alkenylamino, C2-C6-alkynylamino, C1-C6-haloalkylamino, C3-C8-cycloalkyl-C1-C6-alkylamino, C1-C6-alkoxyamino, C1-C6-haloalkoxyamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylcarbonyl-C1-C6-alkylamino, Ci-

C6-haloalkylcarbonyl-C1-C6-alkylamino, C1-C6-alkoxycarbonyl-C1-C6-alkylamino, C2-C6-alkenylthio, C1-C6-alkoxy-C1-C6-alkylcarbonyl, C1-C6-haloalkoxycarbonylamino, di(C1-C6-haloalkyl)amino-Ci-C6-alkyl, Cg-C6-halocycloalkenyloxy-C1-C6-alkyl, Ci-C6-alkoxy(C1-C6-alkyl)aminocarbonyl, C1-C6-haloalkylsulfonylaminocarbonyl, C1-C6-alkylsulfonylaminocarbonyl, C1-C6-alkoxycarbonylalkoxy, C1-C6-alkylaminothiocarbonylamino, Cg-C6-cycloalkyl-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-alkylthiocarbonyl, Cg-C6-cycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxycarbonyl, di-C1-C6-alkylaminothiocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-haloalkoxy, Cg-C6-halocycloalkoxy-C1-C6-alkybdi-C1-C6-alkylaminocarbonylamino, C1-C6-alkoxy-C2-C6-alkenybC1-C6-alkylthiocarbonyloxy^i-C6-haloalkoxy-C1-C6-alkoxy, C1-C6-haloalkylsulfonyloxy, C1-C6-alkoxy-C1-C6-haloalkyl, di(C1-C6-haloalkyl)amino, di-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylaminocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkylamino, tri-C1-C6-alkylsilyl-C2-C6-alkynyloxy, tri-C1-C6-alkylsilyloxy, tri-C1-C6-alkylsilyl-C2-C6-alkynyl, cyano(Ci-C6-alkoxy)-Ci-C6-alkyl,di- C1-C6-alkyltbio-C1-C6-alkyl, C1-C6-alkoxysulfonyl, C3-C8-halocycloalkoxycarbonylC1-C6-alkyl-C3-C8-cycloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, C2-C6-alkenyloxycarbonyl, C2-C6-alkynyloxycarbonyl, C1-C6-cyanoalkoxycarbonyl, C1-C6-alkylthio-C1-C6-alkoxycarbonyl, C2-C6-alkynylcarbonyloxy, C2-C6-haloalkynylcarbonyloxy, cyanocarbonyloxy, C1-C6-cyanoalkylcarbonyloxy, C3-C8-cycloalkylsulphonyloxy, C3-C8-cycloalkyl-C1-C6-alkylsulphonyloxy, C3-C8-halocycloalkylsulphonyloxy, C2-C6-alkenylsulphonyloxy, C2-C6-alkynylsulphonyloxy, C1-C6-cyanoalkylsulphonyloxy, C2-C6-haloalkenylsulphonyloxy, C2-C6-haloalkynylsulphonyloxy, C2-C6-alkynylcycloalkyloxy, C2-C6-cyanoalkenyloxy, C2-C6-cyanoalkynyloxy, C1-C6-alkoxycarbonyloxy, C2-C6-alkenyloxycarbonyloxy, C2-C6-alkynyloxycarbonyloxy, C1-C6-alkoxy-C1-C6-alkylcarbonyloxy, sulfilimines, sulfoximines and SF5 or Z'Q1; R5may be optionally substituted with one or more R6;

Z1 is a direct bond,

Q'is selected from the group consisting of phenyl, benzyl, naphthalenyl, a 5- or 6- membered aromatic ring, an 8- to 11-membered aromatic multi-cyclic ring system, an 8- to 11-membered aromatic fused ring system, a 5- or 6-member ed heteroaromatic ring, an 8- to 11-membered heteroaromatic multi-cyclic ring system and an 8- to 11- membered heteroaromatic fused ring system; wherein the heteroatom of the heteroaromatic rings is selected from N, O or S, and each ring or ring system may be optionally substituted with one or more substituents independently selected from R13, or

Q'is selected from the group consisting ofa 3- to 7-membered non-aromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered non-aromatic heterocyclic ring, an 8- to 15 -member ed non-aromatic multi-cyclic ring system, an 5- to 15 member ed spirocyclic ring system, and an 8- to 15 -member ed non-aromatic fused ring system, wherein, the heteroatom of the non-aromatic rings is selected from N, O or S(0)o-2, and C ring member of the nonaromatic carbocylic or non-aromatic heterocyclic rings or ring systems may be replaced with and each ring or ring system may be
optionally substituted with one or more substituents independently selected from R13;

R2, R3,R2a, R3*, R2b and R3b are independently selected from the group consisting of hydrogen, halogen, cyano, Ci-C4-alkyl, Cz-C4-alkenyl, C2-C4- alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkoxy andCi-C4-haloalkoxy;

R2 and R3; R2 and R3 ; and or R2 and R3btogether with the atoms to which they are attached may form 3- to 5- member ed non-aromatic carbocylic ring or heterocyclic ring which may be optionally substituted with halogen, C1-C2- alkyl, Ci-Cz-haloalkyl or Ci-Cz-alkoxy;

R4aand R4b are independentlyselected from the group consisting of hydrogen, cyano, hydroxy, NRbRc, (C=0)-Rd, S(0)o-2Re, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, tri- C1-C6-alkylamino and CgC8-cycloalkyl;

Rb and Rcare independentlyselected from the group consisting ofhydrogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4- alkoxy, C3-C8-cycloalkyl and C3-C8-halocycloalkyl;

Rdis selected from the group consisting ofhydrogen, hydroxy, halogen, NRbRc, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6- haloalkoxy, C3-C8-cycloalkyl and C3-C8-halocycloalkyl;

R'isselected from the group consisting ofhydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy and C3-C8-cycloalkyl and C3-C8-halocycloalkyl;

R6 and R13 are independently selected from the group consisting of hydrogen, halogen, hydroxy, cyano, nitro,Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkyl-C3-C8-cycloalkyl, C3-C8-halocycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, C3-C8-cycloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkyl-C1-C6-thioalkyl, 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, Ci-C6-alkylcarbonyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-hydroxyalkenyl, C2-C6-hydroxyalkynyl, C3-C8-halocycloalkoxy, C3-C8-cycloalkyl-C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, 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, tri-C1-C6-alkylsilyl, C1-C6-alkylsulfonylamino, C1-C6-haloalkylsulfonylamino, C 1 -C6-alkylcarbonylthio, C1-C6-alkylsulfonyloxy, C1-C6-alkylsulfinyloxy, C6-C10-arylsulfonyloxy, C6-C10-arylsulfinyloxy, C6-Cio-arylsulfonyl, C6-C10-arylsulfinyl, C6-C10-arylthio, C1-C6-cyanoalkyl, C2-C6-alkenylcarbonyloxy, C1-C6-alkoxy-C1-C6-alkylthio, C1-C6-alkylthio-C1-C6-alkoxy, C2-C6-haloalkenylcarbonyloxy, C1-C6-alkoxycarbonyl-C1-C6-alkyl, Ci-C6-alkoxy-C2-C6-alkynyl, C2-C6-alkynylthio, C3-C8-halocycloalkylcarbonyloxy, C2-C6-alkenylamino, C2-C6-alkynylamino, C1-C6-haloalkylamino, C3-C8-cycloalkyl-C1-C6-alkylamino, C1-C6-alkoxyamino, C1-C6-haloalkoxyamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylcarbonyl-C1-C6-alkylamino, Ci-C6-haloalkylcarbonyl-C1-C6-alkylamino, C1-C6-alkoxycarbonyl-C1-C6-alkylamino, C2-C6-alkenylthio, C1-C6-alkoxy-C1-C6-alkylcarbonyl, C1-C6-haloalkoxycarbonylamino, di(C1-C6-haloalkyl)amino-Ci-C6-alkyl, C3-C8-halocycloalkenyloxy-C1-C6-alkyl, Ci-C6-alkoxy(C1-C6-alkyl)aminocarbonyl, C1-C6-haloalkylsulfonylaminocarbonyl, C1-C6-alkylsulfonylaminocarbonyl, C1-C6-alkoxycarbonylalkoxy, C1-C6-alkylaminothiocarbonylamino, C3-C8-cycloalkyl-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-alkylthiocarbonyl, C3-C8-cycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxycarbonyl, di-C1-C6-alkylaminothiocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-haloalkoxy, C3-C8-halocycloalkoxy-C i -C6-alkyl,di-C1-C6-alkylaminocarbonylamino, Ci-C6-alkoxy-C2-C6-alkenyl,Ci-C6-alkylthiocarbonyloxy,Ci-C6-haloalkoxy-Ci-C6-alkoxy, Ci-C6-haloalkylsulfonyloxy, C1-C6-alkoxy-C1-C6-haloalkyl, di(Ci-C6-haloalkyl)amino, di-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylaminocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkyl, Ci-C6-alkylaminocarbonyl-C1-C6-alkylamino, C1-C6-alkylsilyl-C2-C6-alkynyloxy, tri-C1-C6-alkylsilyloxy, tri-Ci-C6-alkylsilyl-C2-C6-alkynyl, cyano(C1-C6-alkoxy)-Ci-C6-alkyl,di- C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkoxysulfonyl, C3-C8-halocycloalkoxycarbonylC1-C6-alkyl-C3-C8-cycloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, C2-C6-alkenyloxycarbonyl, C2-C6-alkynyloxycarbonyl, C1-C6-cyanoalkoxycarbonyl, C1-C6-alkylthio-C1-C6-alkoxycarbonyl, C2-C6-alkynylcarbonyloxy, C2-C6-haloalkynylcarbonyloxy, cyanocarbonyloxy, C1-C6-cyanoalkylcarbonyloxy, C3-C8-cycloalkylsulphonyloxy, C3-C8-cycloalkyl-C1-C6-alkylsulphonyloxy, C3-C8-halocycloalkylsulphonyloxy, C2-C6-alkenylsulphonyloxy, C2-C6-alkynylsulphonyloxy, C1-C6-cyanoalkylsulphonyloxy, C2-C6-haloalkenylsulphonyloxy, C2-

C6-haloalkynylsulphonyloxy, C2-C6-alkynylcycloalkyloxy, C2-C6-cyanoalkenyloxy, C2-C6- cyanoalkynyloxy, C1-C6-alkoxycarbonyloxy, C2-C6-alkenyloxycarbonyloxy, C2-C6- alkynyloxycarbonyloxy, C1-C6-alkoxy-C1-C6-alkylcarbonyloxy, sulfilimines, sulfoximines and SFs;

and/or N-oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof;

with the proviso that following compounds are excluded from the definition of compound of formula (I);

N-(2-methoxyethyl)-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2- carboxamide and ethyl 6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2- carboxylate.

2) The compound of formula (I) as claimed in claim 1, wherein

R1 selected from the group consisting of CF3, CHFz, CFzCl, CFzCF3 CHzF, CHzCF3, CHClCF3 and CClzCF3;

L1 is a direct bond, -CR2R3-;

A is a fused heterobicyclic ring having N at one or more bridgehead; wherein said ring is optionally substituted with one or more identical or different groupsof RA;

RA is selected from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy, SFs, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8- cycloalkylalkyl and C1-C6-haloalkyl;

R8and R9are independently selected from the group consisting of hydrogen, halogen, cyano, Ci- C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl andCi- C6-alkylthio; or

R8 and R9 together with the atoms to which they are bound form C(=0) or a vinyl group or a saturated, monocyclic 3- to 7-member ed heterocyclicring or carbocyclic ring, wherein the ring members of heterocyclic includeC, N, O and S(0)o-z; and wherein the vinyl group, the heterocyclic ring or the carbocyclic ring is unsubstituted or substituted with one or more identical or different R8b, whereinR8b is selected from the group consisting of halogen, cyano, nitro, hydroxyl, sulfanyl, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6- alkylthio, C1-C6-haloalkylthio andC3-C8-cycloalkyl.

3) The compound of formula (I) as claimed in claim 1, wherein

R1 selected from the group consisting of CF3, CHFz, CFzCl, CHClCF3 and CClzCF3;

L1 is a direct bond;

A is
; wherein“#” and indicate point of attachments and said ring is rationally substituted with one or more identical or different groupsof RA;

RA is selected from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy, SF5, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8- cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C4-alkyl and C1-C6-hydroxyalkyl;

R8and R9are independently selected from the group consisting of hydrogen, halogen, cyano, Ci- C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl and C3-C8-cycloalkyl; or

R8 and R9 together with the atoms to which they are bound form C(=0) or a vinylgroup.

4) The compound of formula (I) as claimed in claim 1, wherein said compound of formula (I) is selected from N-(3-methoxyphenyl)-7-(5-(trifluoromethyl)-l ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2- a]pyridine-2-carboxamide; N-(4-methoxyphenyl)-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)imidazo[l,2-a]pyridine-2-carboxamide; N-(p-tolyl)-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)imidazo[l,2-a]pyridine-2-carboxamide; N-(3-fluorophen l 7-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)imidazo[l,2-a]pyridine-2 -carboxamide; N-(2,4-difluorophenyl)-7-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N-(4- chlorophenyl)-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[1,2-a]pyridine-2- carboxamide; N-(2-fluorophen l )-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2- a]pyridine-2-carboxamide; 7 -(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)-N-(4- (trifluoromethyl)benzyl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N-(pyridin-3-yl)-7-(5- (fluorophen l )- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N-benzyl-7-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N-(pyridin-4-yl)- 7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N-(4- chlorophenyl)-N-methyl-7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3 -yl)imidazo[ 1 ,2-a]pyridine-2- carboxamide; N-methyl-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2- carboxamide; N-methyl-N-(2-phenoxyethyl)-7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3- yl)imidazo[l,2-a]pyridine-2-carboxamide; N-(4-cyanophenyl)-7-(5-(trifluoromethyl)- 1 ,2,4- oxadiazol-3-yl)imidazo[l,2-a]pyridine-2 -carboxamide; N-(3-methoxyphenyl)-6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N-(2,4- difluorophenyl)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2- carboxamide; N-(4-chlorophenyl)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2- a]pyridine-2-carboxamide; N-(p-tolyl)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2- a]pyridine-2-carboxamide; N-(2-fluorophen l )-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)imidazo[l,2-a]pyridine-2-carboxamide; N-methyl-6-(5-(trifluoromrthyl)-1,2,4-oxadiazol-3- yl)imidazo[l,2-a]pyridine-2-carboxamide; N-(4-methoxyphenyl)-6-(5-(trifluoromethyl)-1,2,4-

-xadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-benzyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2 -carboxamide; N-(3-fluorophenyl)-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N,N-dimethyl-6-(5-(trifluoromethyl)-l, 2, 4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2 -carboxamide; N-(4-chloro-2-fluorophenyl)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-(4-cyanophenyl)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-(2-methoxyphenyl)-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N-(pyridin-3-yl)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-(2,6-difluorophenyl)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2 -carboxamide; N-(3-fluorobenzyl)-6-(5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2 -carboxamide; N-(pyridin-4-yl)-6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; azetidin-l-yl(7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methanone; N-(2-methoxyethyl)-7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l ,2-a]pyridine-2-carboxamide; N-isobutyl-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-neopentyl-7 -(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-isopentyl-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-(4-chlorobenzyl)-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-(4-methoxybenzyl)-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-(3-chlorobenzyl)-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2 -carboxamide; N-(3-methoxybenzyl)-7-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N-(2-fluorobenzyl)-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-(4-(dimethylamino)benzyl)-7 -(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l ,2-a]pyridine-2-carboxamide; N-(3,4-dichlorobenzyl)-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; ethyl 7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxylate hydrobromide; 3-(2-(((3-methoxyphenyl)thio)methyl)imidazo[ 1 ,2-a]pyridin-7-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-(((4- chlorophenyl)thio)methyl)imidazo[l,2-a]pyridin-7-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(2-(((4-fluorophen l )thio)methyl)imidazo[l,2-a]pyridin-7-yl)-5-(trifluoromethyl)- 1,2,4-oxadiazole; 3-(2-(((4-methoxyphenyl)thio)methyl)imidazo[l,2-a]pyridin-7-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-((phenylthio)methyl)imidazo[l,2-a]pyridin-7-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-(((2 fluorophen l )thio)methyl)imidazo[l,2-a]pyridin-7-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 5-(trifluoromethyl)-3-(2-(((4-(trifluoromethyl)phenyl)thio)methyl)imidazo[ 1 ,2-a]pyridin-7-yl)- 1 ,2,4-oxadiazole; 3-(2-(((4-methoxybenzyl)thio)methyl)imidazo[l,2-a]pyridin-7-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(2-((propylthio)methyl)imidazo[ 1 ,2-a]pyridin-7 -yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2- (((4-chlor<¾)henyl)sulfonyl)methyl)imidazo[l,2-a]pyridin-7-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(2-(((4-methoxyphenyl)sulfonyl)methyl)imidazo[l,2-a]pyridin-7-yl)-5- (trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-(((4- uorop en )henyl)sulfonyl)methyl)imidazo[l,2-a]pyridin-7-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-((phenylsulfonyl)methyl)imidazo[l ,2-a]pyridin-7-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-(((2-fluorophenyl)sulfonyl)methyl)imidazo[l,2-a]pyridin-7-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(2-(((4-methoxybenzyl)sulfonyl)methyl)imidazo[l,2-a]pyridin-7-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(2-((propylsulfonyl)methyl)imidazo[l,2-a]pyridin-7 -yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 5-(trifluoromethyl)-3-(2-(((4-(trifluoromethyl)phenyl)sulfonyl)methyl)imidazo[ 1 ,2-a]pyridin-7-yl)- 1 ,2,4-oxadiazole; 6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)-N-(4- (trifluoromethyl)benzyl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; morpholino(6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methanone; N-(2-methoxyethyl)-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N-isobutyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N -cyclopentyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l ,2-a]pyridine- 2-carboxamide; (3-methoxypyrrolidin- 1 -yl)(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methanone; azetidin- 1 -yl(6-(5 -(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methanone; N-(cyclopropylmethyl)-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2 -carboxamide; N-benzyl-N-methyl-6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N-( 1 -phenylethyl)-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N-(l-cyanocyclopropyl)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)miidazo[l,2-a]pyridine-2-carboxamide; N-(2-methoxyethyl)-N-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-(3-chlorobenzyl)-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2 -carboxamide; N-(3-methoxybenzyl)-6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N-(4-chlorobenzyl)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-isobutyl-N-methyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l ,2-a]pyridine-2-carboxamide; ethyl 6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxylate; 3-(2-(ethoxymethyl)imidazo[l ,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; N-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)benzamide; 4-methoxy-N-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)benzamide; 4-chloro-N-((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)benzamide; 2-(4- chlorophenyl)-N-((6-(5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)acetamide; 3-chloro-N-((6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)benzamide; 3,4-dichloro-N-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-

yl)methyl)benzamide; N-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)iimclazo[l,2-a]pyridm-2-yl)methyl)picolinamide; N-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)iimclazo[l,2-a]pyridm-2-yl)methyl)propionamide; 4-(trifluoromtihoxy)-N-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)benzamide; 4-fluoro-N-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)benzamide; 2-fluoro-N-((6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)benzamide; N-((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)oxazole-4-carboxamide; 3-fluoro-N-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)benzamide; 2-phenyl-N-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)acetamide; 4-(dimethylamino)-N-((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)benzamide; 3-methyl-N-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)butanamide; 4-(trifluoromethyl)-N-((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)benzamide; N-((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)nicotinamide; N-((6-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridm-2-yl)methyl)isonicotinamide; 3-(2-(((4-methoxyphenyl)thio)methyl)imidazo[ 1 ,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-((phenylthio)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(2-(((4-chlorophenyl)thio)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1,2,4-oxadiazole; 3-(2-(((3-chlorophenyl)thio)methyl)iimclazo[l,2-a]pyridm-6-yl)-5-(trifluoromethyl)- 1,2,4-oxadiazole; 3-(2-(((3-fluorophenyl)thio)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1,2,4-oxadiazole; 3-(2-(((4-fluorophenyl)thio)methyl)iimclazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-(((2-fluorophenyl)thio)methyl)imidazo[ 1 ,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-((propylthio)methyl)imidazo[ 1 ,2-a]pyridin-6-yl)-5-(trifluoroinethyl)-l ,2,4-oxadiazole; 3-(2-((benzylthio)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(2-(((4-methoxybenzyl)thio)methyl)imidazo[ 1 ,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-(((3,4-dichlorophenyl)thio)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(2-(((3,5-dichlorophenyl)thio)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-((isobutylthio)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-((cyclopentylthio)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-((cyclohexylthio)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1,2,4-oxadiazole; 3-(2-(((2-ethylphenyl)thio)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1,2,4-oxadiazole; 3-(2-((phenylsulfonyl)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-(((3,4-dichlorophenyl)sulfonyl)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(2-(((3-chlorophenyl)sulfonyl)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-(((4-chlorophenyl)sulfonyl)methyl)iimclazo[l,2-

a]pyridin-6-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-(((3-fluorophenyl)sulfonyl)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)-l,2,4-oxadiazole; 3-(2-(((4-fluor<¾)henyl)sulfonyl)methyl)miidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(2-(((4-methoxybenzyl)sulfonyl)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-((cyclohexylsulfonyl)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole; 3-(2-(((2-fluorophenyl)sulfonyl)inethyl)iimclazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-(((4-methoxyphenyl)sulfonyl)methyl)imidazo[ 1 ,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-(((3,4-dichlorophenyl)sulfinyl)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; 3-(2-(((3-chlorophenyl)sulfinyl)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)-1,2,4-oxadiaz(Ae; 3-(2-(((2-fluorophenyl)sulfinyl)methyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole; N-(methyl(oxo)(phenyl)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)acetamide; N-((2-fluor(¾)henyl)(methyl)(oxo)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)acetamide; N-((3-fluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)acetamide; N-((4-fluor(¾)henyl)(methyl)(oxo)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)acetamide; N-((3-methoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)acetamide; N -(dimethyl(oxo)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)acetamide; N-( 1 -oxidotetrahydro-2H- 1 l6-thiopyran- 1 -ylidene)-2-(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)acetamide; N-((4-chlorophenyl)(2-methoxyethyl)(oxo)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)acetamide; N-(isopropyl(methyl)(oxo)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)acetamide; N-((4-methoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)acetamide; N-(methyl(oxo)(4-(trifluorometh)d)phenyl)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)acetamide; N-((3,5-dichlorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)acetamide; N-( 1 -oxidotetrahydro- 1 l6-thiophen- 1 -ylidene)-2-(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)acetamide; N-((4-bromophenyl)(methyl)(oxo)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)acetamide; N-((3,4-dichlor<¾)henyl)(methyl)(oxo)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)acetamide; N-(4-oxido- 1 ,4l6-oxathian-4-ylidene)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)acetamide; N-((2-mtihoxyphenylXmethyl)(oxo)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl)imidazo[l,2-a]pyridin-2-yl)acetamide; N-((4-methoxypyridin-2-yl)(methyl)(oxo)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)acetamide; N-((4- chlorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)acetamide; N-(methyl(oxo)(o-tolyl)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)acetamide; N-((3-chlorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-2-(6-(5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)acetamide; (3-fluoryl)henyl)(methyl)((2-methyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-3 -yl)imino)-l6-sulfanone; N-((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)butyramide; immo(methyl)((7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyri3-trifluoropropyl)-l6-sulfanone; methyl(( 1 -methyl- 1 H-imidazol-4-yl)methyl)((2- methyl-7 -(5 -(trifluoromethyl)- 1.2.4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)imino)-l6-sulfanone; dimethyl((2-methyl-7-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-3-yl)imino)-l6-sulfanone;

(cyclopropylmethyl)(methyl)((2-methyl-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)imino)-l6-sulfanone; (2,6-dichlorophenyl)(methyl)((2-methyl-7-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-3-yl)imino)-l6-sulfanone; (2-chloro-4-fluorophenyl)(methyl)((2-methyl-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)imino)-l6-sulfanone; (2-chloro-4-(trifluoromethyl)phenyl)(methyl)((2-methyl-7-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-3-yl)imino)-l6-sulfanone;

methyl((2-methyl-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)imino)(4-(trifluoromethoxy)phenyl)-l6-sulfanone; methyl((2- methyl-7 -(5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)imino)(4-methylbenzyl)-l6-sulfanone; (4-methoxyphenyl)(methyl)((2-methyl-7 -(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-3-yl)imino)-l6-sulfanone; benzyl(methyl)((2-methyl-7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)imino)-l6-sulfanone; methyl((2-methyl-7-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-3-yl)imino)(pyridin-3-yl)-l6-sulfanone; (isoxazol-4-ylmethyl)(methyl)((2-methyl-7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-3-yl)imino)-l6-sulfanone; ((1,2,4-oxadiazol-3-yl)methyl)(methyl)((2-methyl-7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-3-yl)imino)-l6-sulfanone; methyl((2-methyl-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)imino)(oxazol-4-ylmethyl)-l6-sulfanone; methyl((2-methyl-7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)imino)(thiazol-4-ylmethyl)-l6-sulfanone; (2-chloro-6-methoxyphenyl)(methyl)((2-methyl-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)imino)-l6-sulfanone; methyl((2-methyl-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)imino)(pyrimidin-5-yl)-l6-sulfanone; (3-chloro-4-(trifluoromethyl)phenyl)(methyl)((2-methyl-7-(5-(trifluoromethyl)-1,2,4-oxacliazol-3-yl)imidazo[ 1 ,2-a]pyridin-3-yl)imino)-l6-sulfanone; isopropyl(methyl)((2-methyl-7-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-3-yl)imino)-l6-sulfanone;

ethyl(methyl)((2-methyl-7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l ,2-a]pyridin-3-yl)imino)-l6-sulfanone; (2-methoxyethyl)(methyl)((2-methyl-7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)imino)-l6-sulfanone; (isopropylimino)(methyl)(2-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)-l6-sulfanone; ((cyclopropylmethyl)imino)(methyl)(2-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)-l6-sulfanone; ((isoxazol-4-ylmethyl)imino)(methyl)(2-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)miidazo[l,2-a]pyridin-3-yl)-l6-sulfanone; ((2-methoxyethyl)imino)(methyl)(2-methyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-3-yl)-l6-sulfanone; methyl(2-methyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)(methylimino)-l6-sulfanone; (ethylimino)(methyl)(2-methyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-3-yl)-l6-sulfanone; methyl(((l-methyl-lH-imidazol-4-yl)methyl)imino)(2-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)-l6-sulfanone; methyl(2-methyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridm-3-yl)((3,3,3-trifluoropropyl)mimo)-l6-sulfanone; ((4-methoxybenzyl)imino)(methyl)(2-methyl-6-(5-(tiifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)-l6-sulfanone; methyl((( 1 -methyl- 1 H-pyrazol-4-yl)methyl)imino)(2-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3- yl)-l6-sulfanone; ((4-chlorobenzyl)imino)(methyl)(2-methyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)-l6-sulfanone; methyl((( 1 -methyl- 1 H- 1 ,2,4-triazol-3-yl)methyl)imino)(2-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)-l6-sulfanone; methyl(2-methyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-3-yl)(phenylimino)-l6-sulfanone; ((2,4-difluo!Ophenyl)immo)(methyl)(2-methyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-3-yl)-l6-sulfanone; ((4-fluorophenyl)imino)(methylX2-methyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l ,2-a]pyridin-3-yl)-l6-sulfanone; (tert-butylimino)(methyl)(2-methyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridm-3-yl)-l6-sulfanone; methyl(2-methyl-6-(5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl)imidazo[l,2-a]pyridm-3-yl)(pyridin-3-ylimino)-l6-sulfanone;

(benzylimino)(methyl)(2-methyl-6-(5-(trifIuOTomethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-3-yl)-l6-sulfanone ; ((4-methoxyphenyl)imino)(methyl)(2-methyl-6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-3-yl)-l6-sulfanone; methyl(2-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)((4-methylbenzyl)imino)-l6-sulfanone; methyl(2-methyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)((4-(trifluoromethoxy)phenyl)imino)-l6-sulfanone; ((2-chloro-4-(trifluoromethjd)phenyl)iinino)(rnethyl)(2-rnethyl-6-(5-(trifluorornethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)-l6-sulfanone; ((2-chloro-4-fluorophenyl)imino)(methylX2-methyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-3 -yl)-l6-sulfanone; ((2,6-dichlorophenyl)miino)(methyl)(2-methyl-6-(5-(tiifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)-l6-sulfanone; ((2-chloro-6-methoxyphenyl)imino)(methyl)(2-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)-l6-sulfanone; methyl(2-methyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-3-yl)((thiazol-4-ylmethyl)imino)-l6-sulfanone; methyl(2-methyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)((oxazol-4-ylmethyl)imino)-l6-sulfanone; (((1,2,4-oxadiazol-3-yl)methyl)imino)(methyl)(2-methyl-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l ,2-a]pyridin-3-yl)-l6-sulfanone ; methyl(2-methyl-6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)(pyrimidin-5-ylimino)-l6-sulfanone; ((3-chloro-4-(trifluoromethjd)phenyl)iinino)(rnethyl)(2-rnethyl-6-(5-(trifluorornethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-3-yl)-l6-sulfanone; (isopropyliminoXmethylX(6-(5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)-l6-sulfanone;

((cyclopropylmethyl)iminoXmethylX(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)-l6-sulfanone; ((isoxazol-4-ylmethyl)imino)(methyl)((6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)-l6-sulfanone; ((2-methoxyethyl)imino)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin- 2-yl)methyl)-l6-sulfanone; methyl(methylimino)((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)-l6-sulfanone; (ethylimino)(methyl)((6-(5-

(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)-l6-sulfanone;

methyl((( 1 -methyl- 1 H-imidazol-4-yl)methyl)imino)((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)-l6-sulfanone; methyl((6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)((3,3,3-trifluoropropyl)imino)-l6-sulfanone; ((4-methoxybenzyl)imino)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxacliazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)-l6-sulfanone; methyl((( 1 -methyl- 1 H-pyrazol-4-yl)methyl)imino)((6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)-l6-sulfanone; ((4-chlorobenzyl)iminoXmethyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)-l6-sulfanone; methyl(((l-methyl-lH-1,2,4-triazol-3-yl)methyl)imino)((6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)-l6-sulfanone;

methyl(phenylimino)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)-l6-sulfanone; ((2,4-difluorophenyl)imino)(methyl)((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)-l6-sulfanone; ((4-fluorophenyl)iminoXmethyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)-l6-sulfanone; (tert-butylimino)(methyl)((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)-l6-sulfanone; methyl(pyridin-3-ylimino)((6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)-l6-sulfanone;

(benzylimino)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)-l6-sulfanone; ((4-methoxyphenyl)imino)(methyl)((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)-l6-sulfanone; methyl((4-methylbenzyl)immo)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)-l6-sulfanone; niethyl((4-(trifluoromethoxy)phenyl)imino)((6-(5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)-l6-sulfanone; ((2-chloro-4-(trifluoromethyl)phenyl)miino)(methyl)((6-(5-(tiifluoromethyl)-1,2,4-oxadiazol-3-yl)miidazo[l,2-a]pyridin-2-yl)methyl)-l6-sulfanone; ((2-chloro-4-fluorophenyl)imino)(methyl)((6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)-l6-sulfanone; ((2,6-dichlorophenyl)imino)(methyl)((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)-l6-sulfanone; ((2-chloro-6-methoxyphenyl)imino)(methyl)((6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)-l6-sulfanone ; methyl((thiazol-4-ylmethyl)imino)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)-l6-sulfanone; methyl((oxazol-4-ylmethyl)imino)((6-(5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)-l6-sulfanone; (((1 ,2,4-oxadiazol-3-yl)methyl)imino)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)-l6-sulfanone; methyl(pyrimidin-5-ylimino)((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)-l6-sulfanone; ((3-chloro-4-(trifluoromethyl)phenyl)iminoXmethylX(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)-l6-sulfanone; N-(methyl(oxo)(phenyl)-l6-sulfaneylidene)-7-(5-

(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N-((4-chlorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N-((4-methoxyphenyl)(methyl)(oxo)-l6-sulfaneylidene)-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-(methyl(oxo)(m-tolyl)-l6-sulfaneylidene)-7-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-((2-fluorophenyl)(methyl)(oxo)-l6-sulfaneylidene)-7-(5-(trifIuoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N -((2,4-difluorophenyl)(methyl)(oxo) -l6-sulfaneylidene)-7 -(5 -(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2 -carboxamide; N-((3-(dimethylamino)phenyl)(methyl)(oxo)-l6-sulfaneylidene)-7-(5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-(dimethyl(oxo)-l6-sulfaneylidene)-7-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N- (ethyl(methyl)(oxo)-l6-sulfaneylidene)-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N -(tert-buty l(methyl)(oxo) -l6-sulfaneylidene)-7 -(5 -(trifluoromethyl)- 1.2.4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2 -carboxamide; N-((cyclopropylmethyl)(methyl)(oxo)-l6-sulfaneylidene)-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-(benzyl(methyl)(oxo)-l6-sulfaneylidene)-7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; N-(methyl(oxo)(pyrimidin-5-yl)-l6-sulfaneylidene)-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-(methyl(oxo)(pyridazin-4-yl)-l6-sulfaneylidene)-7-(5-(trifIuoromethyl)-l, 2, 4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2 -carboxamide; N-(methyl(oxo)(pyrazin-2-yl)-l6-sulfaneylidene)-7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carboxamide; N-(methyl(oxo)(pyridin-4-yl)-l6-sulfaneylidene)-7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxamide; methyl(phenyl)((7 -(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)imino)-l6-sulfanone; (4-chlorophenyl)(methyl)((7 -(5-(trifluoromethyl)-l ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)imino)-l6-sulfanone; (4-methoxyphenyl)(methyl)((7 -(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)imino)-l6-sulfanone; methyl(m-tolyl)((7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)imino)-l6-sulfanone; (2-fluorophenyl)(methyl)((7-(5-(trifluoromethjd)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)imino)-l6-sulfanone; (2,4-difluorophenyl)(methyl)((7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)imino)-l6-sulfanone; (3-(dimethyLamino)phenyl)(methyl)((7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)imino)-l6-sulfanone; dimethyl((7 -(5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)imino)-l6-sulfanone; ethyl(methyl)((7 -(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)imino)-l6-sulfanone; tert-butyl(methyl)((7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)imino)-l6-sulfanone; (cyclopropylmethyl)(methyl)((7 -(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-

yl)imidazo[ 1 ,2-a]pyridin-2-yl)imino)-l6-sulfanone; benzyl(methyl)((7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)imino)-l6-sulfanone; methyl(pyrimidin-5-yl)((7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)imino)-l6-sulfanone;

methyl(pyridazin-4-yl)((7 -(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)imino)-l6-sulfanone; methyl(pyrazin-2-yl)((7 -(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)imino)-l6-sulfanone; methyl(pyridin-4-yl)((7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)imino)-l6-sulfanone; methyl(phenyl)(((7 -(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; methyl(3-methylbenzyl)(((7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3 -yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; methyl(pyridin-4-ylmethyl)(((7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; methyl(pyrimidin-4-ylmethyl)(((7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; methyl(pyridin-3-yl)(((7 -(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; methyl(pyridin-2-yl)(((7 -(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; methyl(((7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l ,2-a]pyridin-2-yl)methyl)imino)(5-(trifluoromethyl)pyridin-2-yl)-l6-sulfanone; (5-methoxypyridin-2-yl)(methyl)(((7 -(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; (5-fluoropyridin-2-yl)(methyl)(((7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; methyl(pyrimidin-5-yl)(((7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; methyl(pyridazin-4-yl)(((7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; methyl( 1 -methyl- 1 H-pyrazol-4-yl)(((7 -(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; isoxazol-4-yl(methylX((7 -(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; (2-methoxythiazol-4-yl)(methyl)(((7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; dimethyl(((7-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; ethyl(methyl)(((7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; tert-butyl(methyl)(((7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; (cyclopropylmethyl)(methyl)(((7-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; methyl(((7 -(5 -(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l ,2-a]pyridin-2-yl)methyl)imino)(3,3,3-trifluoropropyl)-l6-sulfanone; (2-methoxyethyl)(methyl)(((7-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; benzyl(methyl)(((7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; (3-methoxybenzyl)(methyl)(((7-(5-(trifluoromethyl)- 1 ,2,4-

oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; (3-fluorobenzyl)(methyl)(((7-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; isopropyl(methyl)(((6-(5-(trifluo!Omethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; (cyclopropylmethyl)(methyl)(((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; (isoxazol-4-ylmethyl)(methyl)(((6-(5-(trifluoromethyl)-l ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; (2-methoxyethyl)(methyl)(((6-(5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; dimethyl(((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; ethyl(methyl)(((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone methyl(( 1 -methyl- 1 H-imidazol-4-yl)methyl)(((6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; methyl(((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)(3,3,3-trifluo!OpiOpyl)-l6-sulfanone; (4-methoxybenzyl)(methyl)(((6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; methyl(( 1 -methyl- 1 H-pyrazol-4-yl)methyl)(((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; (4-chlorobenzyl)(methyl)(((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; methyl((l-methyl-lH-1,2,4-triazol-3-yl)methyl)(((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; methyl(phenyl)(((6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; (2,4-difluorophenyl)(methyl)(((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; (4-fluo«¾)henyl)(methyl)(((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; tert-butyl(methyl)(((6-(5 -(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; methyl(pyridin-3-yl)(((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; benzyl(methyl)(((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; (4-methoxyphenyl)(methyl)(((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; methyl(4-methylbenzyl)(((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3 -yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; mrthyl(4-(trifluoromethoxy)phenyl)(((6-(5-(trifluorornethyl)-1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; (2-chloro-4- (trifluoromethyl)phenyl)(methyl)(((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; (2-chloro-4-fluorophenyl)(methyl)(((6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; (2,6-dichlorophenyl)(methyl)(((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; (2-chloro-6-methoxyphenyl)(methyl)(((6-(5-

(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; methyl(thiazol-4-ylmethyl)(((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin- 2-yl)methyl)imino)-l6-sulfanone; methyl(oxazol-4-ylmethyl)(((6-(5-(trifluoromethyl)- 1 ,2,4- oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone; ((1 ,2,4-oxadiazol-3- yl)methyl)(methyl)(((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2- yl)methyl)imino)-l6-sulfanone; methyl(pyrimidin-5-yl)(((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol- 3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)methyl)imino)-l6-sulfanone and (3-chloro-4- (trifluoromethyl)phenyl)(methyl)(((6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2- a]pyridin-2-yl)methyl)imino)-l6-sulfanone.

5) The compound of formula (I) as claimed in claim 1, wherein said compound is used as fungicide.

6) A combination comprising the compound of formula (I) as claimed in claim 1 and at least one further pesticidally active substance selected from the group consisting of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertilizers and nutrients.

7) A composition for controlling or preventing plant diseases comprising the compound of formula

(I) as claimed in claim 1 and at least one agrochemically acceptable auxiliary.

8) The composition as claimed in claim 7, wherein said compoision may further comprises at least one additional active ingredient.

9) The composition as claimed in claim 7, wherein said composition is applied to seedand the amount of compound of the formula (I)in said composition is ranges from 0.1 gai to 10 kgai per 100 kg of seeds.

10) The composition as claimed in claim 7, wherein the plant diseases is caused by rust pathogens selected from the group comprising of Hemileia vastatrix (Coffee rust), Uromyces appendiculatus/fabae/ phaseoli (rust of beans) Puccinia spp. (rusts) on various plants selected from P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. Hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals selected from wheat, barley or rye and Phakopsora spp. on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans.

11) 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 6 or the composition claimed in claim 7.

12) 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 6 or the composition claimed in claim 7, is applied to the seeds of plants.

13) A process for the preparation of the compound of formula (I) as claimed in claim 1, wherein said process comprising the steps of:

a) reacting a compound of formula i with a alpha-halo carbonyl compound of formula vto afford a compound of formula ii;

ii

I X= Br, Cl, I

wherein, L1 is direct bond;
b) reacting the compound of formula ii with a hydroxyl amine to afford a compound of formula in;

ii ill

wherein, L1 is direct bond; and A is

c) reacting a compound of formula iii with anacid anhydride of formula (d) orwith anacid chloride compound of formula (e) to afford compound of formula iv;

iv

wherein, L1 is direct bond;A is ; andX is Cl, Br or I.

d) reacting the compound of formula iv with sulphoximine compound of formula (a) to afford compound of formula (I);

Iv Formula I

wherein, L1 is direct bond; and A is

14) A process for the preparation of compound of formula (I) as claimed in claim 1, wherein said process comprising the steps of:

a) reacting a compound of formula i with a compound of formula ixto afford a compound of formula vi;

X= Br, Cl, I

wherein, L1 is direct bond; and A is

b) reacting the compound of formula vi with a hydroxyl amine to afford a compound of formula vn;

vii

wherein, L1 is direct bond; and A is

c) reacting the compound of formula vii with anacid anhydride of formula (d) orwith anacid chloride compound of formula (e) to afford compound of formula viii;

vil viii

wherein, L1 is direct bond;
d) reacting the compound of formula viii with a compound of formula (a) to afford compound of formula (I);

wherein, L1 is direct bond;
15) A process for the preparation of compound of formula (I) as claimed in claim 1, wherein said process comprising the steps of:

a) reacting a compound of formula i with a compound of formula xto afford a compound of formula xi;

wherein, L1 is direct bond; A

b) reacting the compound of formula xi with a hydroxyl amine to afford a compound of formula

X11;

wherein, L1 is direct bond;

c) reacting the compound of formula xii with anacid anhydride of formula (d) orwith anacid chloride compound of formula (e) to afford compound of formula xiii;

wherein, L1 is direct bond;

d) reacting the compound of formula xiii with a compound of formula (f) to afford compound of formula xiv;

wherein, L1 is direct bond;
e) oxidizingthe compound of formula xiv with a suitbale oxidizing agent to afford a compound of formula (I);

wherein, L1 is direct bond;
16) A process for the preparation of compound of formula (I) as claimed in claim 1, wherein said process comprising the steps of:

a) reacting a compound of formula xii with a suitable alkali metal azide compoundto afford a compound of formula xv;

L1 is direct bond;

b) reacting the compound of formula xv with a suitable reducing agentto afford a compound of formula xvi;

L1 is direct bond;
c) reacting the compound of formula xvi with a carboxylic acid of formula (b) orwith a carboxylic acid chloride compound of formula (c) to afford compound of formula (I);

L1 is direct bond; A i in which Yis -NR10 and

17) A process for the preparation of compound of formula (I) as claimed in claim 1, wherein said process comprising the steps of:

a) reacting a compound of formula iv with a suitable reducing reagentto afford a compound of formula xvii;

wherein, L1 is direct bond; A

b) reacting the compound of formula xvii with a suitable oxidizing reagentto afford a compound of formula xviii;

wherein, L1 is direct bond;

c) reacting the compound of formula xviii with a sulphoximine compound of formula (a)to afford compound of formula (I);

wherein, L1 is direct bond; A

18) A compound of formula (B);

wherein,

;wherein“#” indicate point of attachment to L1;

L1 is direct bond;

indicate point of attachments;

R8and R9are independently selected from the group consisting of hydrogen, halogen, cyano, Ci- C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl and C3-C8-cycloalkyl; k is an integer ranging from Oand 1 ;

Risselected from the group consisting of hydrogen, azide, halogen, hydroxy, C1-C6-alkyl, C1-C6- haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio.C3-C8- cycloalkyl,amino-Ci-C6-alkyl, di-C1-C6-alkylamino, NHSOz-C1-C6-alkyl, -S(=0)(=NH)-C1-C6- alkyl; -C(=0)-Ci-C6-alkyl, C(=0)-C1-C6-alkoxy, C1-C6-alkylsulfonyl, hydroxy-C1-C6-alkyl, - C(=0)-NH2, C(=0)-NH(Ci-C6-alkyl), Ci-C6-alkylthio-Ci-C6-alkyl, C1-C6-alkylamino-C1-C6- alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, aminocarbonyl-C1-C6-alkyl andC1-C6-alkoxy-C1-C6- alkyl;

with the proviso that the following compounds are excluded from the definition of compound of formula (I);

ethyl (Z)-2-(6-(N'-hydroxycarbamimidoyl)imidazo[ 1 ,2-a]pyridin-2-yl)acetate, 6-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxylic acid and ethyl (Z)-2- (7-(N'-hydroxycarbamimidoyl)imidazo[l,2-a]pyridin-2-yl)acetate.

19) The compound of formula (B) as claimed in claim 1, wherein said compound of formula (B) is selected from 7 -(N'-hydroxycarbamimidoyl)imidazo[ 1 ,2-a]pyridine-2-carboxylic acid, ethyl 2-(7- (5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)acetate, 7-(5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carboxylic acid, 7-(5- (trifluoromethyl)-4, 5-dihydro- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carbaldehyde, 7-(5- (trifluoromethyl)-4, 5-dihydro- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carbaldehyde, 2- (chloromethyl)-lV'-hydroxyimidazo[l,2-a]pyridine-7-carboximidamide, 3-(2- (chloromethyl)imidazo[l,2-a]pyridin-7-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-(2-

(azidomethyl)imidazo[ 1 ,2-a]pyridin-7-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole, ethyl 2-(6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridin-2-yl)acetate, 6 -(N'-hydroxycarbamimidoyl)imidazo[l,2-a]pyridine-2 -carboxylic acid, ethyl 2-(6-(5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)acetate, 6-(5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridine-2-carbaldehyde, 6-(5-(trifluoromethyl)-4, 5-dihydro- 1, 2, 4-oxadiazol-3-yl)imidazo[ 1 ,2-a]pyridine-2-carbaldehyde, 3-(2-(chloromethyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)- 1 ,2,4-oxadiazole, 2-(chloromethyl)-N'-hydroxyimidazo[l,2-a]pyridine-6-carboximidamide, 3-(2-(azidomethyl)imidazo[l,2-a]pyridin-6-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole and imino(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)imidazo[l,2-a]pyridin-2-yl)methyl)-l6-sulfanone.

Documents

Application Documents

# Name Date
1 202117053079.pdf 2021-11-18
2 202117053079-STATEMENT OF UNDERTAKING (FORM 3) [18-11-2021(online)].pdf 2021-11-18
3 202117053079-PRIORITY DOCUMENTS [18-11-2021(online)].pdf 2021-11-18
4 202117053079-NOTIFICATION OF INT. APPLN. NO. & FILING DATE (PCT-RO-105-PCT Pamphlet) [18-11-2021(online)].pdf 2021-11-18
5 202117053079-FORM 1 [18-11-2021(online)].pdf 2021-11-18
6 202117053079-FIGURE OF ABSTRACT [18-11-2021(online)].jpg 2021-11-18
7 202117053079-DECLARATION OF INVENTORSHIP (FORM 5) [18-11-2021(online)].pdf 2021-11-18
8 202117053079-COMPLETE SPECIFICATION [18-11-2021(online)].pdf 2021-11-18
9 202117053079-Proof of Right [15-12-2021(online)].pdf 2021-12-15
10 202117053079-FORM-26 [18-02-2022(online)].pdf 2022-02-18
11 202117053079-FORM 3 [17-05-2022(online)].pdf 2022-05-17