Fused heterocyclic compounds and its uses thereof

Abstract

The present invention provides a fused heterocyclic compound of formula (I), or salts, stereoisomers, metal complexes, polymorphs or N-oxides thereof (I) wherein, Q, R1, Y, R2 and R2a are as defined in the detailed description. The present invention also provides methods for their preparation and use of the compounds of formula (I) as a pest control agent.

Description

[0001] FUSED HETEROCYCLIC COMPOUNDS AND ITS USES THEREOF

[0002] FIELD OF THE INVENTION

[0003] The present invention relates to compounds of formula (I). More particularly, the present invention relates to fused heterocyclic compounds of formula (I) and a process for the preparation thereof. The present invention further relates to the composition comprising those compounds, and to their use as pest control agents.

[0004] BACKGROUND OF THE INVENTION

[0005] The currently available modern insecticides and acaricides have to satisfy many requirements, for example, level of activity, long lasting efficacy, broadness of insecticidal spectrum as well as environmental and toxicological safeness and additional beneficial effects, and the possible use thereof. During the past decades, efforts to develop selective insecticides have been made that are acting specifically on biochemical modes of action being present only in insects or mites, but additionally showing properties that differ from known insecticides in an advantageous way.

[0006] Heterocyclic compounds with pesticidal activity are known and described, for example, in W02020250183. However, there is a continuous need for new compounds which are more effective, less toxic, and environmentally safer. Furthermore, some of those existing pesticides are highly toxic, or remain for a long time in the environment because of their residual properties, which may become a growing problem due to the disruption of the ecosystem.

[0007] Thus, there is a constant need for new pest control agents with improved pesticidal activity, a broader spectrum of efficacy, longer lasting activity, increased plant compatibility, better environmental safety, and improved formulation properties as well as a low risk of resistance development.

[0008] Therefore, the present invention envisages such compounds that satisfy or overcome drawbacks associated with the prior art.

[0009] Surprisingly, we have found that certain novel pesticidally active fused heterocyclic compounds with sulfur containing substituents being subject of this invention have favorable properties as pesticides and are environmentally safer, as desired.

[0010] SUMMARY OF THE INVENTION

[0011] Accordingly, the present invention provides fused heterocyclic compounds of formula (I) or salts, stereoisomers, metal complexes, polymorphs or N-oxides thereof wherein, R1, Y, Q, R2and R2aare as defined in the detailed description.

[0012] The present invention also provides a process for preparing the compound of formula (I) or salts thereof. The present invention provides a composition for controlling or preventing invertebrate pests comprising a compound of formula (I), salts, stereoisomers, metal complexes, polymorphs, or N-oxides thereof and at least one additional component selected from the group consisting of surfactants and auxiliaries.

[0013] The composition additionally comprises at least one additional biologically active and compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers or nutrients.

[0014] The present invention provides use of the compound of formula (I), salts, stereoisomers, metal complexes, polymorphs, or N-oxides, compositions or combinations thereof, for combating invertebrate pests in agricultural crops and / or horticultural crops or parasites on animals or wooden dwellings and commercial structures.

[0015] The present invention provides a method of combating invertebrate pests comprising contacting the invertebrate pests, their habitat, breeding ground, food supply, plant, seed, soil, area, material or environment in which the invertebrate pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from pest attack or infestation with a biologically effective amount of the compounds of formula (I) or salts, stereoisomers, metal complexes, polymorphs, or N- oxides thereof as well as their composition or combination thereof.

[0016] DETAILED DESCRIPTION OF THE INVENTION

[0017] DEFINITIONS:

[0018] The definitions provided herein for the terminologies used in the present disclosure are for illustrative purposes only and in no manner limit the scope of the present invention disclosed in the present disclosure.

[0019] 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 nonexclusive 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.

[0020] 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.

[0021] 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".

[0022] 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).

[0023] 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.

[0024] As referred to in this disclosure, the term "invertebrate pest" includes arthropods, gastropods and nematodes of economic importance as pests. The term "arthropod" includes but is not limited to insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans. The term "gastropod" includes but is not limited to snails, slugs and other Stylommatophora. The term "nematode" refers to a living organism of the Phylum Nematoda. The term "helminths" includes but is not limited to roundworms, heartworms, phytophagous nematodes (Nematoda), flukes (Tematoda), acanthocephala and tapeworms (Cestoda).

[0025] The term "agronomic" refers to the production of field crops such as for food and fiber and includes the growth of corn, soybeans and other legumes, rice, cereal (e.g., wheat, oats, barley, rye, rice, maize), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone and citrus), small fruit (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives).

[0026] 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.

[0027] 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.

[0028] The compounds of the present disclosure may be present either in pure form or as mixtures of different possible isomeric forms such as stereoisomers or constitutional isomers. The various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, and geometric isomers. Any desired mixtures of these isomers fall within the scope of the claims of the present disclosure. One skilled in the art will appreciate that one stereoisomer may be more active and / or may exhibit beneficial effects when enriched relative to the other isomer(s) or when separated from the other isomer(s). Additionally, the person skilled in the art knows processes or methods or technology to separate, enrich, and / or to selectively prepare said isomers.

[0029] The meaning of various terms used in the description shall now be illustrated.

[0030] The term "aliphatic compound / s" or "aliphatic group / s" used herein is an organic compound / s whose carbon atoms are linked in straight chains, branched chains, or non-aromatic rings.

[0031] The term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" or -N(alkyl) or alkylcarbonylalkyl or alkylsuphonylamino includes straight-chain or branched C1 to C24 alkyl, preferably C1 11 C15 alkyl, more preferably Ci to C10 alkyl, most preferably Ci to C6 alkyl. Representative examples of alkyl include methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2- dimethylpropyl, 1 -ethylpropyl, hexyl, 1,1 -dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3 -dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1 -ethyl- 1 -methylpropyl and l-ethyl-2-methylpropyl or the different isomers. If the alkyl is at the end of a composite substituent, as, for example, in alkylcycloalkyl, the part of the composite substituent at the start, for example the cycloalkyl, may be mono- or polysubstituted identically or differently and independently by alkyl. The same also applies to composite substituents in which other radicals, for example alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy and the like, are at the end.

[0032] The term "alkenyl", used either alone or in compound words includes straight-chain or branched C2 to C24 alkenes, preferably C2 to C15 alkenes, more preferably C2 to C10 alkenes, most preferably C2 to C6 alkenes. Representative 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-l - butenyl, 3-methyl-l -butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl- 3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, l,l-dimethyl-2-propenyl, 1,2-dimethyl-l- propenyl, 1 ,2-dimethyl-2 -propenyl, 1 -ethyl- 1 -propenyl, l-ethyl-2-propenyl, 1 -hexenyl, 2-hexenyl, 3- hexenyl, 4-hexenyl, 5-hexenyl, 1 -methyl- 1 -pentenyl, 2-methyl-l -pentenyl, 3-methyl-l -pentenyl, 4- methyl-1 -pentenyl, l-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2- pentenyl, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1- methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2- butenyl, 1 , 1 -dimethyl-3-butenyl, 1 ,,,dimethyl- 1 -butenyl, 1.2-dimethyl-2-butenyl, 1,2-dimethyl-3- butenyl, 1 , 3 -dimethyl- 1 -butenyl, 1 ,3-dimethyl-2-butenyl, 1.3-dimethyl-3-butenyl, 2.2-dimethyl-3- butenyl, 2 , 3 -dimethyl- 1 -butenyl, 2 , 3 -dimethyl-2-butenyl, 2 , 3 -dimethyl-3 -butenyl, 3, 3 -dimethyl- 1- butenyl, 3,3-dimethyl-2-butenyl, 1 -ethyl- 1 -butenyl, 1 -ethyl-2-butenyl, l-ethyl-3-butenyl, 2-ethyl- 1- butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1 -ethyl- l-methyl-2- propenyl, l-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.

[0033] The term "alkynyl", used either alone or in compound words includes straight-chain or branched C2 to C24 alkynes, preferably C2 to C15 alkynes, more preferably C2 to C10 alkynes, most preferably C2 to C6 alkynes. Non-limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2- butynyl, 3-butynyl, l-methyl-2-propynyl, 1 -pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2- butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 3 -methyl- 1-butynyl, l,l-dimethyl-2-propynyl, 1- ethyl-2-propynyl, 1 -hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l-methyl-2-pentynyl, 1- methyl-3-pentynyl, l-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-l - pentynyl, 3-methyl-4-pentynyl, 4-methyl-l -pentynyl, 4-methyl-2-pentynyl, l,l-dimethyl-2-butynyl, l,l-dimethyl-3-butynyl, l,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl, 1- ethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1 -ethyl- l-methyl-2-propynyl and the different isomers. This definition also applies to alkynyl as a part of a composite substituent, for example haloalkynyl etc., unless specifically defined elsewhere. The term "alkynyl" can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. The term "cycloalkyl" means alkyl closed to form a ring. Non-limiting examples include but are not limited to 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.

[0034] The term "cycloalkylalkyl" denotes cycloalkyl substitution on an alkyl group. It refers to a cycloalkyl group attached via an alkyl linkage to the rest of the molecule.

[0035] For example, as used herein, the term “C3-C6-cycloalkyl-C1-Cn-alkyl-” refers to a C1-Cn-alkyl radical as generally defined above substituted by one or more C CT-cycloalkyl groups as generally defined above. C3-C6-cycloalkyl-C1-C3-alkyl is to be construed accordingly. Examples include but are not limited to, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclopentylethyl and cyclohexylmethyl.

[0036] The term "cycloalkenyl" means alkenyl closed to form a ring including monocyclic, partially unsaturated hydrocarbyl groups. Non-limiting examples include but are not limited to 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.

[0037] The term "cycloalkynyl" means alkynyl closed to form a ring including monocyclic, partially unsaturated groups. Non-limiting examples include but are not limited to 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.

[0038] 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.

[0039] 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 one or more 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 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,

[0040] 2.2.2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,

[0041] 2.2.2-trichloroethyl, pentafluoroethyl, l,l-dichloro-2,2,2-trifluoroethyl, and l,l,l-trifluoroprop-2-yl. This definition also applies to haloalkyl as a part of a composite substituent, for example haloalkylaminoalkyl etc., unless specifically defined elsewhere.

[0042] 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.

[0043] The term "haloalkoxy" means straight-chain or branched alkoxy groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1 -chloroethoxy, 1 -bromoethoxy, 1 -fluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2- dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and l,l,l-trifluoroprop-2-oxy. This definition also applies to haloalkoxy as a part of a composite substituent, for example haloalkoxyalkyl etc., unless specifically defined elsewhere.

[0044] The term "haloalkylthio" means straight-chain or branched alkylthio groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1 -chloroethylthio, 1- bromoethylthio, 1- fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2- chloro-2- fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2- trichloroethylthio, pentafluoroethylthio and l,l,l-trifluoroprop-2-ylthio. This definition also applies to haloalkylthio as a part of a composite substituent, for example haloalkylthioalkyl etc., unless specifically defined elsewhere.

[0045] Non-limiting examples of "haloalkylsulfinyl" include CF3S(O), CC13S(O), CF3CH2S(O) and CF3CF2S(O). Examples of "haloalkylsulfonyl" include CF3S(O)2, CC13S(O)2, CF3CH2S(O)2and CF3CF2S(O)2.

[0046] The term "hydroxy" means -OH, and "Amino" means -NRR, wherein R can be H or any possible substituent such as alkyl. The term "carbonyl " means -C(O)-, "carbonyloxy" means -OC(O)-, “oxo” means =0, "sulfinyl" means SO, and "sulfonyl" means S(0)2.

[0047] The term "alkoxy" used either alone or in compound words included Ci to C24 alkoxy, preferably Ci to C15 alkoxy, more preferably Ci to Cw alkoxy, most preferably Ci to C alkoxy. Examples of alkoxy include methoxy, ethoxy, propoxy, 1 -methylethoxy, butoxy, 1 -methylpropoxy, 2-methylpropoxy, 1,1- dimethylethoxy, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3 -methylbutoxy, 2,2-dimethylpropoxy, 1- ethylpropoxy, hexoxy, 1,1 -dimethylpropoxy, 1,2-dimethylpropoxy, 1 -methylpentoxy, 2- methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1 -dimethylbutoxy, 1 ,2-dimethylbutoxy, 1,3- dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2- ethylbutoxy, 1 , 1 ,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1 -ethyl- 1 -methylpropoxy and l-ethyl-2- methylpropoxy and the different isomers. This definition also applies to alkoxy as a part of a composite substituent, for example haloalkoxy, alkynylalkoxy, etc., unless specifically defined elsewhere.

[0048] The term "Alkoxyalkyl" denotes alkoxy substitution on alkyl. Non-limiting examples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2and CH3CH2OCH2CH2. The term "alkoxy alkoxy" denotes alkoxy substitution on alkoxy. The term "alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1 -methylethylthio, butylthio, 1 -methylpropylthio, 2-methylpropylthio, 1,1- dimethylethylthio, pentylthio, 1 -methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2- dimethylpropylthio, 1 -ethylpropylthio, hexylthio, 1,1 -dimethylpropylthio, 1 ,2-dimethylpropylthio, 1- methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1 -dimethylbutylthio,

[0049] 1.2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3- dimethylbutylthio, 1 -ethylbutylthio, 2-ethylbutylthio, 1 , 1 ,2-trimethylpropylthio, 1,2,2- trimethylpropylthio, 1 -ethyl- 1 -methylpropylthio and l-ethyl-2-methylpropylthio and the different isomers.

[0050] Halocycloalkyl, halocycloalkenyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylcarbonyl, cycloalkylcarbonyl, haloalkoxylalkyl, and the like, are defined analogously to the above examples.

[0051] The term "alkylthioalkyl" denotes alkylthio substitution on alkyl. Representative examples of "alkylthioalkyl" include -CH2SCH2, -CH2SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2and CH3CH2SCH2CH2. The term "Alkylthioalkoxy" denotes alkylthio substitution on alkoxy. The term "cycloalkylalkylamino" denotes cycloalkyl substitution on alkyl amino.

[0052] The terms alkoxyalkoxyalkyl, alkylaminoalkyl, dialkylaminoalkyl, cycloalkylaminoalkyl, cycloalkylaminocarbonyl and the like, are defined analogously to "alkylthioalkyl" or cycloalkylalkylamino.

[0053] 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.

[0054] 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.

[0055] Non-limiting examples of "alkylsulfinyl" include but are not limited to methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1 -methylethylsulfinyl, butylsulfinyl, 1 -methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1 -dimethylethylsulfinyl, pentylsulfinyl, 1 -methylbutylsulfinyl, 2-methylbutylsulfinyl, 3- methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1 -ethylpropylsulfinyl, hexylsulfinyl, 1,1- dimethylpropylsulfinyl, 1 ,2-dimethylpropylsulfinyl, 1 -methylpentylsulfinyl, 2-methylpentylsulfinyl, 3- methylpentylsulfinyl, 4-methylpentylsulfinyl, 1 , 1 -dimethylbutylsulfinyl, 1 ,2-dimethylbutylsulfinyl,

[0056] 1.3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3- dimethylbutylsulfinyl, 1 -ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1 , 1 ,2-trimethylpropylsulfinyl, 1,2,2- trimethylpropylsulfinyl, 1 -ethyl- 1 -methylpropylsulfinyl and l-ethyl-2-methylpropylsulfinyl and the different isomers. The term "arylsulfinyl" includes Ar-S(O), wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulfinyl as a part of a composite substituent, for example haloalkylsulfinyl etc., unless specifically defined elsewhere. The term C1-C6 alkylsulfonyl denotes a radical of the formula -S(O)2R in which R is C1-C6 alkyl radical as generally defined above.

[0057] Non-limiting examples of "alkylsulfonyl" include but are not limited to methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1 -methylethylsulfonyl, butylsulfonyl, 1 -methylpropylsulfonyl, 2- methylpropylsulfonyl, 1,1 -dimethylethylsulfonyl, pentylsulfonyl, 1 -methylbutylsulfonyl, 2- methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1 -ethylpropylsulfonyl, hexylsulfonyl, 1,1 -dimethylpropylsulfonyl, 1 ,2-dimethylpropylsulfonyl, 1 -methylpentylsulfonyl, 2- methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1 , 1 -dimethylbutylsulfonyl, 1 ,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3- dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1 -ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2- trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1 -ethyl- 1 -methylpropylsulfonyl and l-ethyl-2- methylpropylsulfonyl and the different isomers. The term "arylsulfonyl" includes Ar-S(O)2, wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulfonyl as a part of a composite substituent, for example alkylsulfonylalkyl etc., unless defined elsewhere.

[0058] "Alkylamino", "dialkylamino", and the like, are defined analogously to the above examples.

[0059] The term C1-C6-hydroxy alkyl denotes a radical of the formula in which C1-C6 alkyl is substituted with hydroxy group. Non-limiting examples include -CH2OH, -CH(CH3)-0H, CH2CH2-OH.

[0060] Tire term “optionally substituted” as used herein means that the group referenced is either unsubstituted or is substituted by a designated substituent, for example, “Cs-Ca-cycloalkyl is optionally substituted with 1 or 2 halo atoms” means C3-C4-cycloalkyl, C3-C.4-cycloalkyl substituted with 1 halo atom and C3- CAcycloalkyl substituted with 2 halo atoms. The term “optionally substituted” can be used interchangeably with “unsubstituted or substituted”

[0061] The term "carbocycle" includes "aromatic carbocyclic ring system" and "non aromatic carbocyclic 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 satisfied).

[0062] The term "phenylalkyl" denotes phenyl substitution on an alkyl group. It refers to a phenyl group attached via an alkyl linkage to the rest of the molecule. For example, non-limiting examples of phenyl- C1-C6-alkyl include phenyl methyl (benzyl), phenyl ethyl, and phenyl propyl.

[0063] The term "hetero" in connection with rings refers to a ring in which at least one ring atom is not carbon and which can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs.

[0064] The term "aromatic" indicates that the Huckel rule is satisfied and the term "non aromatic" indicates that the Huckel rule is not satisfied.

[0065] The term "heterocycle" or "heterocyclic" or "heterocyclic ring system " includes "aromatic heterocycle" or "heteroaryl bicyclic ring system" and "non aromatic heterocycle ring or ring system" or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds in which ring may be aromatic or nonaromatic, wherein the heterocycle ring contains at least one heteroatom selected from N, O, S(0)o 2, and or C ring member of the heterocycle may be replaced by C(=O), C(=S), C(=CR*R*) and C=NR*, * indicates integers.

[0066] The term "non aromatic heterocycle" or "non aromatic heterocyclic" means three- to fifteen-membered, preferably three- to twelve -membered, saturated or partially unsaturated heterocycle containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur: mono, bi- or tricyclic heterocycles which contain, in addition to carbon ring members, one to three nitrogen atoms and / or one oxygen or sulphur atom or one or two oxygen and / or sulphur atoms; if the ring contains more than one oxygen atom, they are not directly adjacent; for example (but not limited to) oxiranyl, aziridinyl,oxetanyl, thietanyl, azetidinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl,

[0067] 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3- isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1 -pyrazolidinyl, 3-pyrazolidinyl, 4- pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4- thiazolidinyl, 5-thiazolidinyl, 1-imidazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4- oxadiazolidin-3-yl, l,2,4-oxadiazolidin-5-yl, l,2,4-thiadiazolidin-3-yl, l,2,4-thiadiazolidin-5-yl, 1,2,4- triazolidin-l-yl, l,2,4-triazolidin-3-yl, l,3,4-oxadiazolidin-2-yl, l,3,4-thiadiazolidin-2-yl, 1,3,4- triazolidin-l-yl, l,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl,

[0068] 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-

[0069] 2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol- 1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol- 1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2- yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,

[0070] 3.4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4- dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, pyrazynyl, morpholinyl, thiomorphlinyl, l,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2- tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4- hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, l,3,5-hexahydrotriazin-2-yl, 1,2,4- hexahydrotriazin-3-yl, cycloserines, 2,3,4,5-tetrahydro[lH]azepin-l- or -2- or -3- or -4- or -5- or -6- or -7- yl, 3,4,5,6-tetra-hydro[2H]azepin-2- or -3- or -4- or -5- or -6- or-7-yl, 2,3,4,7-tetrahydro[lH]azepin- 1- or -2- or -3- or -4- or -5- or -6- or-7- yl, 2,3,6,7-tetrahydro[lH]azepin-l- or -2- or -3- or -4- or -5- or -6- or -7- yl, hexahydroazepin- 1- or -2- or -3- or -4- yl, tetra- and hexahydrooxepinyl such as 2, 3,4,5- tetrahydro[l H]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, 2,3,4,7-tetrahydro[lH]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, 2,3,6,7-tetrahydro[lH]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, hexahydroazepin- 1- or -2- or -3- or -4- yl, tetra- and hexahydro- 1,3-diazepinyl, tetra- and hexahydro-

[0071] 1.4-diazepinyl, tetra- and hexahydro- 1,3-oxazepinyl, tetra- and hexahydro- 1 ,4-oxazepinyl, tetra- and hexahydro- 1,3-dioxepinyl, tetra- and hexahydro- 1 ,4-dioxepinyl. This definition also applies to heterocyclyl as a part of a composite substituent, for example, heterocyclylalkyl etc., unless specifically defined elsewhere.

[0072] The term "heteroaryl" or "aromatic heterocyclic" means 5 or 6-membered, fully unsaturated monocyclic ring system containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur; if the ring contains more than one oxygen atom, they are not directly adjacent; 5 -membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom as ring members, for example (but not limited thereto) furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl,

[0073] 1.3.4-triazolyl, tetrazolyl; nitrogen-bonded 5-membered heteroaryl containing one to four nitrogen atoms, or benzofused nitrogen-bonded 5-membered heteroaryl containing one to three nitrogen atoms:

[0074] 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms as ring members and in which two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member may be bridged by a buta-l,3-diene-l,4-diyl group in which one or two carbon atoms may be replaced by nitrogen atoms, where these rings are attached to the skeleton via one of the nitrogen ring members, for example (but not limited to) 1 - pyrrolyl, 1-pyrazolyl, 1,2,4-triazol-l-yl, 1-imidazolyl, 1,2,3-triazol-l-yl and 1,3,4-triazol-l-yl.

[0075] 6-membered heteroaryl which contains one to four nitrogen atoms: 6 -membered heteroaryl groups which, in addition to carbon atoms, may contain, respectively, one to three and one to four nitrogen atoms as ring members, for example (but not limited thereto) 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3- pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, l,3,5-triazin-2-yl,

[0076] 1.2.4-triazin-3-yl and l,2,4,5-tetrazin-3-yl; benzofused 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulphur atom: for example (but not limited to) indol-l-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, benzimidazol-l-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, indazol-l-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl, indazol-7-yl, indazol-2-yl, l-benzofuran-2-yl, l-benzofuran-3-yl, 1- benzofuran-4-yl, l-benzofuran-5-yl, l-benzofuran-6-yl, l-benzofuran-7-yl, l-benzothiophen-2-yl, 1- benzothiophen-3-yl, l-benzothiophen-4-yl, l-benzothiophen-5-yl, l-benzothiophen-6-yl, 1- benzothiophen-7-yl, l,3-benzothiazol-2-yl, 1,3- benzothiazol-4-yl, l,3-benzothiazol-5-yl, 1,3- benzothiazol-6-yl, l,3-benzothiazol-7-yl, l,3-benzoxazol-2-yl, l,3-benzoxazol-4-yl, l,3-benzoxazol-5- yl, l,3-benzoxazol-6-yl and l,3-benzoxazol-7-yl; benzofused 6-membered heteroaryl which contains one to three nitrogen atoms: for example (but not limited to) quinolin-2-yl, quinolin-3-yl, quinolin-4- yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin- 1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl and isoquinolin-8-yl.

[0077] This definition also applies to heteroaryl as a part of a composite substituent, for example heteroarylalkyl etc., unless specifically defined elsewhere.

[0078] The term "heteroarylalkyl" denotes heteroaryl substitution on an alkyl group. It refers to a heteroaryl group attached via an alkyl linkage to the rest of the molecule.

[0079] The term "Trialkylsilyl" includes three branched and / or straight-chain alkyl radicals attached to and linked through a silicon atom such as trimethylsilyl, triethylsilyl and t-butyl-dimethylsilyl. "Halotrialkylsilyl" denotes at least one of the three alkyl radicals is partially or fully substituted with halogen atoms which may be the same or different. The term "alkoxytrialkylsilyl" denotes at least one of the three alkyl radicals is substituted with one or more alkoxy radicals which may be the same or different. The term "trialkylsilyloxy" denotes a trialkylsilyl moiety attached through oxygen.

[0080] Non-limiting examples of "alkylcarbonyl" include C(0)CH3, CYOjCt Cl CH; and C(O)CH(CH3)2- Non-limiting examples of "alkoxycarbonyl" include CH30C(=0), CH3CH2OC(=O), CH3CH2CH2OC(=O), (CH3)2CHOC(=O) and the different butoxy or pentoxycarbonyl isomers. Nonlimiting examples of "alkylaminocarbonyl" include CH3NHC(=0), CH3CH2NHC(=O), CH3CH2CH2NHC(=O), (CH3)2CHNHC(=O) and the different butylamino -or pentylaminocarbonyl isomers. Non-limiting examples of "dialkylaminocarbonyl" include (CH3)2NC(=O), (CH3CH2)2NC(=O), CH3CH2(CH3)NC(=O), CH3CH2CH2(CH3)NC(=O) and (CH3)2CHN(CH3)C(=O). Non-limiting examples of "alkoxy alkylcarbonyl" include CH3OCH2C(=O), CH3OCH2CH2C(=O), CH3CH2OCH2C(=O), CH3CH2CH2CH2OCH2C(=O) and CH3CH2OCH2CH2C(=O). Non-limiting examples of "alkylthioalkylcarbonyl" include CH3SCH2C(=O), CH3SCH2CH2C(=O), CH3CH2SCH2C(=O), CH3CH2CH2CH2SCH2C(=O) and CH3CH2SCH2CH2C(=O). The term haloalkylsufonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkyl amino and the like are defined analogously.

[0081] Non-limiting examples of "alkylaminoalkylcarbonyl" include CH3NHCH2C(=O), CH3NHCH2CH2C(=O), CH3CH2NHCH2C(=O), CH3CH2CH2CH2NHCH2C(=O) and CH3CH2NHCH2CH2C(=O).

[0082] The term "amide" means A-R'C(=O)NR"-B, wherein R' and R" indicates substituents and A and B indicate any group.

[0083] The term "thioamide" means A-R'C(=S)NR"-B, wherein R' and R” indicates substituents and A and B indicate any group.

[0084] The total number of carbon atoms in a substituent group is indicated by the "Q-Cj" prefix where i and j are numbers from 1 to 21. For example, C1-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH3OCH2; C3 alkoxyalkyl designates, for example, CH3CWOCH3). CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2. In the above recitations, when a compound of formula (I) is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

[0085] When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents. Further, when the subscript m in (R)mindicates an integer ranging from for example 0 to 4 then the number of substituents may be selected from the integers between 0 and 4 inclusive.

[0086] When a group contains a substituent that can be hydrogen, then, when this substituent is taken as hydrogen, it is recognized that said group is being un-substituted.

[0087] The embodiments herein, and the various features and advantageous details thereof are explained with reference to the non-limiting embodiments in the description. Descriptions of well-known components and processing techniques are omitted so as to not unnecessarily obscure the embodiments herein. The examples used herein are intended merely to facilitate an understanding of ways in which the embodiments herein may be practiced and to further enable those of skilled in the art to practice the embodiments herein. Accordingly, the examples should not be construed as limiting the scope of the embodiments herein.

[0088] The description of the specific embodiments will so fully reveal the general nature of the embodiments herein that others can, by applying current knowledge, readily modify and / or adapt for various applications such specific embodiments without departing from the generic concept, and, therefore, such adaptations and modifications should and are intended to be comprehended within the meaning and range of equivalents of the disclosed embodiments. It is to be understood that the phraseology or terminology employed herein is for the purpose of description and not of limitation. Therefore, while the embodiments herein have been described in terms of preferred embodiments, those skilled in the art will recognize that the embodiments herein can be practiced with modification within the spirit and scope of the embodiments as described herein.

[0089] Any discussion of documents, acts, materials, devices, articles and the like that has been included in this specification is solely for the purpose of providing a context for the disclosure. It is not to be taken as an admission that any or all of these matters form a part of the prior art base or were common general knowledge in the field relevant to the disclosure as it existed anywhere before the priority date of this application.

[0090] The numerical values mentioned in the description and the description / claims though might form a critical part of the present invention of the present invention, any deviation from such numerical values shall still fall within the scope of the present invention if that deviation follows the same scientific principle as that of the present invention disclosed in the present invention.The inventive compound of the present invention may, if appropriate, be present as mixtures of different possible isomeric forms, especially of stereoisomers, for example E and Z, threo and erythro, and also optical isomers, but if appropriate also of tautomers. Both the E and the Z isomers, and also the threo and erythro isomers, and the optical isomers, any desired mixtures of these isomers and the possible tautomeric forms are disclosed and claimed.

[0091] The term "pest" for the purpose of the present disclosure includes but is not limited to fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, insects and rodents. Also pest is an animal or plant detrimental to humans or human concerns including crops, livestock, and forestry.

[0092] The term "plant" is understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and the plant cultivars which are protectable and non-protectable by plant breeders' rights.

[0093] For the purpose of the present disclosure the term "plant" includes a living organism of the kind exemplified by trees, shrubs, herbs, grasses, ferns, and mosses, typically growing in a site, absorbing water and required substances through its roots, and synthesizing nutrients in its leaves by photosynthesis.

[0094] Examples of "plant" for the purpose of the present invention include but are not limited to agricultural crops such as wheat, rye, barley, triticale, oats or rice; beet, e.g. sugar beet or fodder beet; fruits and fruit trees, such as pomes, stone fruits or soft fruits, e.g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit and citrus trees, such as oranges, lemons, grapefruits or mandarins; any horticultural plants, vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; cucurbitaceae; oleaginous plants; energy and raw material plants, such as cereals, corn, soybean, other leguminous plants, rape, sugar cane or oil palm; tobacco; nuts; coffee; tea; cacao; bananas; peppers; vines (table grapes and grape juice grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broadleaved trees or evergreens, e.g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants.

[0095] Preferably, the plant for the purpose of the present invention includes but is not limited to cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and vegetables, ornamentals, any floricultural plants and other plants for use of human and animals. The term "plant parts" is understood to mean all parts and organs of plants above and below the ground. For the purpose of the present disclosure, the term plant parts includes but is not limited to cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots including taproots, lateral roots, root hairs, root apex, root cap, rhizomes, slips, shoots, fruits, fruit bodies, bark, stem, buds, auxiliary buds, meristems, nodes and internodes.

[0096] The term "locus thereof" includes soil, surroundings of plant or plant parts and equipment or tools used before, during or after sowing / planting a plant or a plant part.

[0097] Application of the compounds of the present disclosure or the compound of the present disclosure in a composition optionally comprising other compatible compounds to a plant or a plant material or locus thereof include application by a technique known to a person skilled in the art which include but is not limited to spraying, coating, dipping, fumigating, impregnating, injecting and dusting.

[0098] The term "applied" means adhered to a plant or plant part either physically or chemically including impregnation.

[0099] Embodiments according to the invention are provided as set out below:

[0100] Embodiment 01:

[0101] Accordingly, the present invention provides fused heterocyclic compounds of formula (I), wherein,

[0102] R1is C1-C6-alkyl;

[0103] Y is selected from oxygen (O) or NRY;

[0104] RYis selected from the group consisting of hydrogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2- C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C3-C5-cycloalkyl, C3-C5-cycloalkyl-C1-C3- alkyl and -C(O)Rla;

[0105] Rlais selected from the group consisting of C i-CT-alkyl, C1-C6-haloalkyl, C3-C5-cycloalkyl and C3-C5-cycloalkyl-C1-C3-alkyl;

[0106] R2is C(=W)R7; wherein W is selected from oxygen (O) or sulfur (S);

[0107] R7is selected from the group consisting of OR4and NR5R6;

[0108] R2ais selected from the group consisting of halogen, cyano, C i-CT-alkyl, C3-C6-cycloalkyl, C1-C6- alkoxy, C1-C6-alkoxy-C3-C6-cycloalkyl, Ci-CT-haloalkyl and Ci-CT-haloalkoxy;

[0109] R4is selected from the group consisting of hydrogen, Ci-CT-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, Ci-CT-haloalkyl, C2-C6-haloalkenyl and CT-CVcycloalkyl; R5is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkcnyl, C2-C6- alkynyl, OR5a, NR5cR5d, C1-C6-haloalkyl, C2-C6-haloalkcnyl, C3-C8-cycloalkyl, C3-C8- cycloalkyl- C1-C6-alkyl, -C(O)OR5d, -Ci-C3-alkyl-C(O)OR5d, -Ci-C3-alkyl-C(O)N(R5d)2, 3- to 6- membered non aromatic heterocyclic ring, 3- to 6- membered non aromatic heterocyclic ring- C1-C6-alkyl, phenyl and phenyl-C1-C6-alkyl; wherein each group may optionally be substituted with one or more groups of R5b;

[0110] R5ais selected from the group consisting of C1-C6-alkyl, C2-C6-alkcnyl, C2-C6-alkynyl, C1-C6- haloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, phenyl-C1-C6-alkyl, and 3- to 6- membered non aromatic heterocyclic ring; wherein said heterocyclic ring and phenyl-C1-C6-alkyl groups may optionally be substituted with one or more groups selected from C 1-C6-alkyl, C1-C6-alkoxy or halogen;

[0111] R5bis selected from the group consisting of halogen, cyano, oxo, hydroxy, C1-C6-alkyl, C1-C6- alkylthio, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, -C(O)O-Ci-C6-alkyl and C1-C6-alkoxy;

[0112] R5Cis selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkcnyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkcnyl and C3-C8-cycloalkyl;

[0113] R5dis independently selected from the group consisting of hydrogen and C1-C6-alkyl;

[0114] R6is selected from the group consisting of hydrogen, C 1-C6-alkyl, C2-C6-alkcnyk C2-C6-alkynyl, C1- C6-alkoxy, C1-C6-haloalkyl, C2-C6-haloalkcnyl and C3-C6-cycloalkyl; or

[0115] R5and R6together with the nitrogen atom to which they are attached may form a 3 - to 6- membered non aromatic heterocyclic ring; wherein said heterocyclic ring optionally contains 1 or 2 heteroatoms independently selected from N, O or S(0)o -2; said heterocyclic ring is optionally substituted by one or more substituents independently selected from halogen, cyano, oxo, C1-C6-alkyl, C1-C6-alkoxy or C1-C6-haloalkyl; or

[0116] NR5R6represents -N=S(O)RxRXa, wherein Rxand RXaare independently selected from the group consisting of cyano, C1-C6-alkyl, C2-C6-alkcnyl, C2-C6-alkynyk phenyl, benzyl and 3- to 6- membered non aromatic heterocyclic ring; wherein said phenyl and benzyl rings are may optionally be substituted by one or more groups selected from halogen or C 1-C6-alkyl; or

[0117] Rxand RXatogether with the sulfur atom to which they are attached may form a 3 - to 6- membered non aromatic heterocyclic ring; wherein said heterocyclic ring optionally contains 1 or 2 heteroatoms independently selected from N, O or S(0)o -2; said heterocyclic ring is optionally substituted by one or more substituents independently selected from halogen, cyano, oxo, C1-C6-alkyl, C1-C6-alkoxy or C1-C6-haloalkyl;

[0118] Q represents partially saturated or unsaturated 5- to 12-membered heterocyclic ring which is substituted by one or more groups of R3and optionally substituted by one group of R10; preferably Q is 6- to 12- membered heteroaryl ring which is substituted by one or more groups of R3and optionally substituted by one group of R10;

[0119] R3is selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-haloalkoxy, - S(O)0-2C1-C3-haloalkyl and -S(O)o iR8=NR9;

[0120] R8is selected from the group consisting of C1-C6-alkyl, C2-C6-alkcnyl, C2-C6-alkynyl, C1-C6- haloalkyl, C2-C6-haloalkcnyl and C3-C8- cycloalkyl;

[0121] R9is selected from the group consisting of hydrogen, cyano, C1-C6-alkyl, C2-C6-alkcnyl, C2- Ce-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, CVCVcycloalkyl and C(=O)R';

[0122] R10is selected from hydrogen or C1-C6-alkyl; or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof.

[0123] Embodiment-02: In an embodiment of the present invention, the compounds of formula (I) are represented by the compounds of formula (1-1), (1-2) or (1-3); wherein, m is 1 or 2; R2ais selected from hydrogen, halogen, cyano, C1-C6-alkyl, C3-C6-cycloalkyl, C1- C6-alkoxy, C1-C6-alkoxy-C3-C6-cycloalkyl, C1-C6-haloalkyl or C1-C6-haloalkoxy; R1, Q, R2, and RYare as defined above for the compounds of formula (I).

[0124] Embodiment-03: According to embodiment 01, the compounds of formula (I) are represented by the compounds of formula (IA); wherein, R1, Q, R2, R2aand Y are as defined above for the compounds of formula (I).

[0125] Embodiment-04: According to embodiments 01 or 03, the compounds of formula (I) are preferably represented by the compounds of formula (IA-1), (IA-1X) (IA-2) or (IA-2X); wherein, R1, Q, R2, R2aand Y are as defined above for the compounds of formula (I).

[0126] Embodiment-05: According to embodiments 01 or 03, the compounds of formula (I) are preferably represented by the compounds of formula (IA-3), (IA-4) or (IA-5); wherein, R1, Q, R2and Y are as defined above for the compounds of formula (I).

[0127] The following list provides definitions, including preferred definitions, for the substituents Q, Y, RY, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, Rla, R2a, Rx, RXa, R5a, R5bR5cand R5dwith reference to the compounds of formula (I), (1-1 to 1-3), (IA), (IA-1), (IA-1X), (IA-2), (IA-2X), (IA-3), (IA-4) or (IA-5) (IB), (IBX), (IC), (ICT) of the present invention. For any one of these substituents, any of the definitions given below may be combined with any definition of any other substituent given below or elsewhere in this document.

[0128] Embodiment 06: According to any of the above embodiments, Q is selected from 6- to 12-membered heteroaryl ring which is substituted by one or more groups of R3and optionally substituted by one group of R10; Preferably Q is selected from the group consisting of Qla to Qlp, wherein R10is selected from hydrogen or Ci-CT-alkyl and R3and n have the same meaning as described above: wherein, # denotes the point of attachment to pyrazolopyrimidine ring.

[0129] Embodiment 07: According to embodiment 06, Q is selected from the group consisting of Qla-1 to Qlp-1, wherein R3is the same as defined above:

[0130]

[0131] Embodiment 08: According to embodiments 01 or 06 or 07, R3is selected from the group consisting of halogen, C1-C6-haloalkyl and C1-C6-haloalkoxy.

[0132] Embodiment 09: According to any of the embodiments 01 or 06 to 08, preferably R3is selected from the group consisting of halogen, C1-C3-haloalkyl and C1-C3-haloalkoxy.

[0133] Embodiment 10: According to any of the embodiments 01 or 06 to 09, more preferably R3is selected from fluoro, fluoromethyl group, a difluoromethyl group, a chlorofluoromethyl group, a dichlorofluoromethyl group, a chlorodifluoromethyl group, a trifluoromethyl group, a pentafluoropropoxy group, a trifluoropropoxy group or a pentafluoroethoxy group.

[0134] Embodiment 11: According to any of the above embodiments, more preferably when Q is Qlg or Qlg- 1 , R3is fluoro.

[0135] Embodiment 12: According to any of the above embodiments, more preferably when Q is QI Z to Qlp, Q1Z-1, Qlm-1, Qln-1, Qlo-1 or Qlp-1, R3is a pentafluoropropoxy group.

[0136] Embodiment 13: According to any of the above embodiments, more preferably when Q is Qla to Qlf, Qlh, Qli, Qlj, Qlk, Qla-1, Qlb-1, Qlc-1, Qld-1, Qle-1, Qle-2, Qlf-1, Qlf-2, Qlh-1 or Qli-1, Qlj- 1, Qlk-1, R3is a a trifluoromethyl group.

[0137] Embodiment 14: According to embodiments 01 or 06, preferably R10is C1-C3-alkyl, more preferably R10methyl.

[0138] Embodiment 15: According to embodiments 01 or 06, preferably n is 1.

[0139] Embodiment 16: According to any of the above embodiments, R1is C1-C3-alkyl.

[0140] Embodiment 17: According to embodiment 16, preferably R1is C1-C3-alkyl selected from methyl, ethyl, n-propyl or isopropyl.

[0141] Embodiment 18: According to embodiments 16 or 17, more preferably R1is ethyl.

[0142] Embodiment 19: According to any of the above embodiments, preferably Y is oxygen (O).

[0143] Embodiment 20: According to any of the above embodiments, preferably Y is NRY. Embodiment 21: According to embodiment 20, RYis selected from the group consisting of hydrogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C3-C5-cycloalkyl, C3-C5-cycloalkyl-C1-C3-alkyl and -C(O)Rla.

[0144] Embodiment 22: According to embodiments 20 or 21, RYis selected from the group consisting of hydrogen, cyano, C1-C3-alkyl, C1-C3-haloalkyl, C3-C5-cycloalkyl, C3-C5-cycloalkyl-C1-C3-alkyl and - C(O)Rla.

[0145] Embodiment 23: According to embodiments 20 or 21 or 22, preferably RYis selected from the group consisting of hydrogen, cyano, C1-C3-alkyl, C1-C3-haloalkyl and -C(O)Rla.

[0146] Embodiment 24: According to embodiments 21 or 22 or 23, Rlais selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C3-C5-cycloalkyl and C3-C5-cycloalkyl-C1-C3-alkyl.

[0147] Embodiment 25: According to embodiments 21 or 22 or 23 or 24, preferably Rlais selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C3-C5-cycloalkyl and C3-C5-cycloalkyl-C1-C3-alkyl. Embodiment 26: According to embodiments 21 or 22 or 23 or 24 or 25, more preferably Rlais selected from C1-C3-alkyl or C1-C3-haloalkyl.

[0148] Embodiment 27: According to any of the above embodiments, R2is C(=W)R7; wherein W is selected from oxygen (O) or sulfur (S).

[0149] Embodiment 28: According to embodiments 01 or 27, preferably W is oxygen (O).

[0150] Embodiment 29: According to embodiments 01 or 27 or 28, preferably R7is OR4.

[0151] Embodiment 30: According to embodiments 01 or 27 or 28, preferably R7is NR5R6.

[0152] Embodiment 31: According to embodiments 01 or 29, R4is selected from the group consisting of hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl and C3-C6- cycloalkyl.

[0153] Embodiment 32: According to embodiments 01 or 29 or 31, R4is selected from hydrogen or C1-C4- alkyl.

[0154] Embodiment 33: According to embodiments 01 or 30, R5is selected from the group consisting of hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, OR5a, NR5cR5d, C1-C4-haloalkyl, C3-C6- cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, -C(O)OR5d, Ci-C3-alkyl-C(O)OR5d, Ci-C3-alkyl- C(O)N(R5d)2, 4- to 6- membered non aromatic heterocyclic ring, 4- to 6- membered non aromatic heterocyclic ring-C1-C4-alkyl, phenyl and phenyl-C1-C4-alkyl; wherein each group may optionally be substituted with one or more groups of R5b.

[0155] Embodiment 34: According to embodiments 01 or 33, R5ais selected from the group consisting of Ci- C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, phenyl-C1-C4- alkyl, and 3- to 6- membered non aromatic heterocyclic ring; wherein said heterocyclic ring and phenyl- C1-C4-alkyl groups may optionally be substituted with one or more groups selected from C1-C4-alkyl, C1-C4-alkoxy or halogen.

[0156] Embodiment 35: According to embodiments 01 or 33 or 34, R5ais selected from the group consisting of C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C3-C6-cycloalkyl-C1-C3-alkyl, phenyl- C1-C3-alkyl, and 5- to 6- membered non aromatic heterocyclic ring; wherein said heterocyclic ring and phenyl-C1-C3-alkyl groups may optionally be substituted with one or more groups selected from C1-C3- alkyl, C1-C3-alkoxy or halogen.

[0157] Embodiment 36: According to embodiments 01 or 33, R5bis selected from the group consisting of halogen, cyano, oxo, hydroxy, C1-C4-alkyl, C1-C4-alkylthio, C1-C4-haloalkyl, C1-C4-hydroxy alkyl, - C(O)O-C1-C4-alkyl and C1-C4-alkoxy.

[0158] Embodiment 37: According to embodiments 01 or 33, R5cis selected from the group consisting of hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl and C3-C6- cycloalkyl.

[0159] Embodiment 38: According to embodiments 01 or 33 or 37, R5cis selected from hydrogen or C1-C4- alkyl.

[0160] Embodiment 39: According to embodiments 01 or 33, R5dis selected hydrogen or C1-C4-alkyl.

[0161] Embodiment 40: According to embodiments 01 or 30, R6is selected from the group consisting of hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy, C1-C4-haloalkyl, C2-C4- haloalkenyl and C3-C6-cycloalkyl.

[0162] Embodiment 41: According to embodiments 01 or 30 or 40, R6is selected from the group consisting of hydrogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl and C3-C6-cycloalkyl.

[0163] Embodiment 42: According to embodiments 01 or 30 or 40 or 41, R6is selected from the group consisting of hydrogen, C1-C3-alkyl and C1-C3-alkoxy.

[0164] Embodiment 43: According to embodiments 01 or 30, NR5R6represents -N=S(O)RxRXa, wherein Rxand RXaare independently selected from the group consisting of cyano, C1-C4-alkyl, C2-C4-alkenyl, C2- C4-alkynyl, phenyl, benzyl and 3- to 6- membered non aromatic heterocyclic ring; wherein said phenyl and benzyl rings are may optionally be substituted by one or more groups selected from halogen or Ci- C4-alkyl; or

[0165] Rxand RXatogether with the sulfur atom to which they are attached may form a 3 - to 6-membered non aromatic heterocyclic ring; wherein said heterocyclic ring optionally contains 1 or 2 heteroatoms independently selected from N, O or S(0)o-2j said heterocyclic ring is optionally substituted by one or more substituents independently selected from halogen, cyano, oxo, C1-C6- alkyl, C1-C6-alkoxy or C1-C6-haloalkyl.

[0166] Embodiment 44: According to embodiments 01 or 30 or 43, NR5R6represents -N=S(O)RxRXa, wherein Rxand RXaare independently selected from cyano, C i-Cs-alkyl, phenyl or benzyl; wherein said phenyl and benzyl rings are may optionally be substituted by one or more groups selected from halogen or C1-C3-alkyl; or Rxand RXatogether with the sulfur atom to which they are attached may form a 5 - to 6-membered non aromatic heterocyclic ring; wherein said heterocyclic ring optionally contains 1 or 2 heteroatoms independently selected from N, O or S(0)o 2.

[0167] Embodiment 45: According to embodiments 01 or 30, R5andR6together with the nitrogen atom to which they are attached may form a 3- to 6-membered non aromatic heterocyclic ring; wherein said heterocyclic ring optionally contains 1 or 2 heteroatoms independently selected from N, O or S(0)o 2; said heterocyclic ring is optionally substituted by one or more substituents independently selected from halogen, cyano, oxo, C11C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkyl.

[0168] Embodiment 46: According to embodiments 01 or 30 or 45, R5and R6together with the nitrogen atom to which they are attached may form a 3- to 6-membered non aromatic heterocyclic ring; wherein said heterocyclic ring optionally contains 1 or 2 heteroatoms independently selected from N, O or S(O)0-2; said heterocyclic ring is optionally substituted by one or more substituents independently selected from halogen, cyano, oxo, C1-C3-alkyl, C1-C3-alkoxy or C1-C3-haloalkyl.

[0169] Embodiment 47: According to any of the above embodiments, R2ais selected from the group consisting of halogen, cyano, C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C3-C6-cycloalkyl, Ci- C4-haloalkyl and C1-C4-haloalkoxy.

[0170] Embodiment 48: According to embodiment 47, R2ais selected from the group consisting of halogen, cyano, C1-C3-alkyl, C3-C5-cycloalkyl, C1-C3-alkoxy, C1-C3-alkoxy- C3-C6-cycloalkyl, C1-C3-haloalkyl and C1-C3-haloalkoxy.

[0171] Embodiment 49: According to embodiments 47 or 48, R2ais selected from the group consisting of halogen, C1-C3-alkyl and C3-C5-cycloalkyl.

[0172] Embodiment 50: According to embodiment 1, R8is selected from the group consisting of C1-C3-alkyl, C2-C3-alkenyl, C2-C3-alkynyl, C1-C3- aloalkyl, C2-C3-haloalkenyl and C3-C6-cycloalkyl.

[0173] Embodiment 51: According to embodiment 1, R9is selected from the group consisting of hydrogen, cyano, C1-C3-alkyl, C2-C3-alkenyl, C2-C3-alkynyl, C1-C3-haloalkyl, C2-C3-haloalkenyl, C3-C6- cycloalkyl and C(=O)R'.

[0174] Embodiment 52: According to this embodiment, for compounds of formula (I) or (IA) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof; values of each group are as follows: wherein,

[0175] R1is C1-C3-alkyl;

[0176] Y is selected from oxygen (O) or NRY;

[0177] RYis selected from the group consisting of hydrogen, cyano, C1-C3-alkyl, C1-C3-haloalkyl, C2- C4-haloalkenyl, C3-C5-cycloalkyl, C3-C5-cycloalkyl-C1-C3-alkyl and -C(O)Rla;

[0178] Rlais selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C3-C5-cycloalkyl and C3-C5-cycloalkyl-C1-C3-alkyl;

[0179] R2is C(=W)R7; wherein W is oxygen (O);

[0180] R7is selected from the group consisting of OR4and NR5R6; R2ais selected from the group consisting of halogen, cyano, Ci-C3-alkyl, C3-C6-cycloalkyl;

[0181] R4is selected from hydrogen or C1-C4-alkyl;

[0182] R5is selected from the group consisting of hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, OR5a, NR5cR5d, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, -C(O)OR5d, Ci-C3-alkyl- C(O)OR5d, Ci-C3-alkyl-C(O)N(R5d)2, 4- to 6- membered non aromatic heterocyclic ring, 4- to 6- membered non aromatic heterocyclic ring-C1-C4-alkyl, phenyl and phenyl-C1-C4-alkyl; wherein each group may optionally be substituted with one or more groups of R5b;

[0183] R5ais selected from the group consisting of C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4- haloalkyl, C3-C6-cycloalkyl-Ci-C3-alkyl, phenyl-Ci-C3-alkyl, and 5- to 6- membered non aromatic heterocyclic ring; wherein said heterocyclic ring and phenyl-Ci-C3-alkyl groups may optionally be substituted with one or more groups selected from Ci-C3-alkyl, Ci-C3-alkoxy or halogen;

[0184] R5bis selected from the group consisting of halogen, cyano, oxo, hydroxy, C1-C4-alkyl, C1-C4- alkylthio, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, -C(O)O-C1-C4-alkyl and C1-C4-alkoxy;

[0185] R5cis selected from hydrogen or C1-C4-alkyl;

[0186] R5dis independently selected from hydrogen or C1-C4-alkyl;

[0187] R6is selected from the group consisting of hydrogen, Ci-C3-alkyl and Ci-C3-alkoxy; or

[0188] R5and R6together with the nitrogen atom to which they are attached may form a 3 - to 6- membered non aromatic heterocyclic ring; wherein said heterocyclic ring optionally contains 1 or 2 heteroatoms independently selected from N, O or S(0)o -2; said heterocyclic ring is optionally substituted by one or more substituents independently selected from halogen, cyano, oxo, Ci-C3-alkyl, Ci-C3-alkoxy or Ci-C3-haloalkyl; or

[0189] NR5R6represents -N=S(O)RxRXa, wherein Rxand RXaare independently selected from cyano, Ci-C3- alkyl, phenyl or benzyl; wherein said phenyl and benzyl rings are may optionally be substituted by one or more groups selected from halogen or Ci-C3-alkyl; or

[0190] Rxand RXatogether with the sulfur atom to which they are attached may form a 5 - to 6- membered non aromatic heterocyclic ring; wherein said heterocyclic ring optionally contains 1 or 2 heteroatoms independently selected from N, O or S(0)o 2;

[0191] Q is selected from the group consisting of QI a to Q Ip;

[0192] wherein, # denotes the point of attachment to the pyrazolopyrimidine ring;

[0193] R3is selected from halogen, C1-C3-haloalkyl or C1-C3-haloalkoxy;

[0194] R10is Ci-C3-alkyl; "n" is an integer ranging from 1 to 2.

[0195] Embodiment 53: According to any of the above embodiments, Q is preferably selected from embodiment 06; wherein R3is fluoro for Qlg-1 and for other Q, R3is selected from C1-C3-haloalkyl or C1-C3-haloalkoxy.

[0196] Embodiment 54: According to this embodiment, the compounds of formula (I) or (IA) are preferably represented by the compounds of formula (IB) or (IBX); wherein, Q, R1, RYand R7are as defined for the compounds of formula (I) or as defined in any of the above embodiments.

[0197] Embodiment 55: According to this embodiment, the compounds of formula (I) or (IA) are preferably represented by the compounds of formula (IC) or (ICX); wherein, Q, R1, RY, R5and R6are as defined for the compounds of formula (I) or as defined in any of the above embodiments.

[0198] Embodiment 56: According to this embodiment, the present invention provides the compounds of formula (Z); wherein, R1, Q, R2and R2aare as defined above for the compounds of formula (I) or as defined in any of the above embodiments.

[0199] Embodiment 57: According to this embodiment, the present invention provides the compounds of formula (A); wherein, R1and Q are as defined above for the compounds of formula (I) or as defined in any of the above embodiments with the proviso that 2-(ethylthio)-3-(6-(2, 2,3,3, 3-pentafluoropropoxy)pyridazin- 3-yl)pyrazolo[l,5-a]pyrimidin-7(4H)-one, 2-(ethylthio)-3-(5-(2, 2,3,3, 3-pentafluoropropoxy)pyrazin- 2-yl)pyrazolo[l ,5-a]pyrimidin-7(4H)-one, and 2-(ethylthio)-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidin-7(4H)-one are excluded from the definition of compound of formula (A).

[0200] Embodiment 58: According to this embodiment, the present invention provides the compounds of formula (B); wherein, Q is as defined above for the compounds of formula (I) or as defined in any of the above embodiments with the proviso that 3-(ethylthio)-4-(5-(2, 2,3,3, 3-pentafluoropropoxy)pyrazin-2-yl)- lH-pyrazol-5-amine, and 3-(ethylthio)-4-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)-lH-pyrazol-5-amine are excluded from the definition of compound of formula (B).

[0201] Embodiment-59: According to this embodiment, the compounds of formula (Z), (A) and (B) are intermediates for preparing the compounds of formula (I).

[0202] Embodiment-60: According to a preferred embodiment of the present invention, the compound of formula (I) of the present invention disclosed in Table-A are selected from ethyl 2-(ethylsulfonyl)-3- (3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxylate; 2-(ethylsulfonyl)-N-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin- 2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(2,2-difluoroethyl)-2-(ethylsulfonyl)-3-(3-methyl-

[0203] 6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N- ethyl-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylic acid; N-cyclopropyl-2-(ethylsulfonyl)-3-(3- methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyr azoIofl, 5-a]pyrimidine-7-carboxamide; N-(cyclopropylmethyl)-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin- 2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)- 3H-imidazo[4,5-b]pyridin-2-yl)-N-(prop-2-yn-l-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-N-isobutyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; (3,3-difluoroazetidin-l-yl)(2-(ethylsulfonyl)-3-(3- methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidin-7-yl)methanone; 2-(ethylsulfonyl)-N,N-dimethyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-allyl-2-(ethylsulfonyl)-3-(3-methyl-6-

[0204] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-(3,3,3- trifluoropropyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-

[0205] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-(2,2,2-trifluoroethyl)pyrazolo[l,5-a]pyrimidine-

[0206] 7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-

[0207] (2,2,3,3,3-pentafluoropropyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; (2-(ethylsulfonyl)-3-(3- methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidin-7-yl)(3- fluoroazetidin-l-yl)methanone; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-

[0208] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-(l-methylcyclopropyl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-methoxy-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine -7-carboxamide; N-(cyanomethyl)-2-

[0209] (ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)-N-phenylpyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(l-cyanocyclopropyl)-2-

[0210] (ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-methyl-3-(6-(trifluoromethyl)imidazo[l,2- a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(6-(2,2,3,3,3- pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N- methyl-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N,N-dimethyl-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; (2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidin-7-yl)(morpholino)methanone; 2-(ethylsulfonyl)-N-isopropyl- 3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(ethylsulfonyl)-N,N-dimethyl-3-(6-(trifluoromethyl)imidazo[l,2-a]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)-N-(2-methylcyclopropyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-(l,l,l- trifluoropropan-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-ethyl-2-(ethylsulfonyl)-N-methyl- 3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyr azolof l,5-a]pyrimidine-7- carboxamide; N-cyclobutyl-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-

[0211] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-propylpyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-methyl-3-(5-(2, 2, 3, 3, 3-pentafluoropropoxy )pyrazin-2-yl)pyrazolo[l, 5- a]pyrimidine-7-carboxamide; ethyl 2-(ethylsulfonyl)-3-(5-(2, 2,3,3, 3 -pentafluoropropoxy )pyrazin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate; 2-(ethylsulfonyl)-N,N-dimethyl-3-(5-(2,2,3,3,3- pentafluoropropoxy)pyrazin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N,N- dimethyl-3-(7-(trifluoromethyl)imidazo[l,2-a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(tert-butyl)-2-(ethylsulfonyl)-3-(5-(2, 2, 3, 3, 3-pentafluoropropoxy )pyrazin-2-yl)pyrazolo[l, 5- a]pyrimidine-7-carboxamide; N-ethyl-2-(ethylsulfonyl)-3-(5-(2, 2, 3, 3, 3-pentafluoropropoxy )pyrazin- 2-yl)pyrazolo[l,5-a]pyrim dine-7-carboxamide; N-cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3- pentafluoropropoxy)pyrazin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(l,l-dioxidothietan-3- yl)-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; N-(cyclopropylmethyl)-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3- pentafluoropropoxy)pyrazin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-ethyl-2-

[0212] (ethylsulfonyl)-N-methyl-3-(5-(2, 2, 3, 3, 3-pentafluoropropoxy )pyrazin-2-yl)pyrazolo[l, 5- a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(8-(2,2,3,3,3-pentafluoropropoxy)imidazo[l,5- a]pyrazin-3-yl)-N-(2,2,2-trifluoroethyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-

[0213] (cyclopropylmethyl)-2-(ethylsulfonyl)-3-(8-(2, 2,3,3, 3-pentafluoropropoxy)imidazo[l, 5-a]pyrazin-3- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-cyclopropyl-2-(ethylsulfonyl)-3-(8-(2,2,3,3,3- pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-3-(5-(2, 2, 3, 3, 3-pentafluoropropoxy )pyrazin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxylic acid; N,N-diethyl-2-(ethylsulfonyl)-3-(5-(2, 2, 3, 3, 3-pentafluoropropoxy )pyrazin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; (3,3-difluoroazetidin-l-yl)(2-(ethylsulfonyl)-3-(5- (2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[l,5-a]pyrimidin-7-yl)methanone; 2-

[0214] (ethylsulfonyl)-N-(3-methylbutan-2-yl)-3-(5-(2, 2,3,3, 3-pentafluoropropoxy)pyr azin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)-N-(oxetan-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-

[0215] (ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-(thietan-3- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-cyclopropyl-2-(ethylsulfonyl)-N-methyl-3-(3- methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-ethyl-2-(ethylsulfonyl)-3-(8-(2,2,3,3,3-pentafluoropropoxy)imidazo[l,5-a]pyrazin-3- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N,N-diethyl-2-(ethylsulfonyl)-3-(3-methyl-6-

[0216] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N- benzyl-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-methoxy-N-methyl-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5-a]pyrimidine-7- carboxylic acid; (2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5- a]pyrimidin-7-yl)(3-fluoroazetidin-l-yl)methanone; N-(cyclopropylmethyl)-2-(ethylsulfonyl)-3-(6- (2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-

[0217] (ethylsulfonyl)-N-methyl-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-N-(prop-2-yn-l- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-methoxy-N-methyl-3-(6-(2,2,3,3,3- pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(2,2-difluoroethyl)- 2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(ethylsulfonyl)-3-(6-(2, 2,3,3, 3-pentafluoropropoxy)pyridazin-3-yl)-N-(thietan-3- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; (3,3-difluoroazetidin-l-yl)(2-(ethylsulfonyl)-3-(6- (2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5-a]pyrimidin-7-yl)methanone; N,N-diethyl- 2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; N-cyclobutyl-2-(ethylsulfonyl)-3-(6-(2, 2,3,3, 3 -pentafluoropropoxy )pyridazin-3- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-neopentyl-3-(6-(2,2,3,3,3- pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(cyanomethyl)-2- (ethylsulfonyl)-3-(6-(2, 2,3,3, 3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(ethylsulfonyl)-N-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin- 2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-ethyl-2-(ethylsulfonyl)-3-(3-methyl-6-

[0218] (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; ethyl 2- (ethylsulfonyl)-3-(8-(2,2,3,3,3-pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)pyrazolo[l,5- a]pyrimidine-7-carboxylate; 2-(ethylsulfonyl)-N-(2-methylcyclopropyl)-3-(6-(2,2,3,3,3- pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(l- cyanocyclopropyl)-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- c]pyridin-2-yl)-N-(prop-2-yn-l-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3- methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)-N-(2,2,3,3,3- pentafluoropropyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)-N-propylpyrazolo[l,5-a]pyrimidine-7-carboxamide; N-cyclopropyl-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-c]pyridin-2-yl)-N-(2,2,2-trifluoroethyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N,N- diethyl-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(cyanomethyl)-2-(ethylsulfonyl)-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-3-(8-(2,2,3,3,3-pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-methyl-3-(8-(2,2,3,3,3- pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-3-(8-(2,2,3,3,3-pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)pyrazolo[l,5- a]pyrimidine-7-carboxylic acid; (3,3-difluoroazetidin-l-yl)(2-(ethylsulfonyl)-3-(8-(2,2,3,3,3- pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)pyrazolo[l,5-a]pyrimidin-7-yl)methanone; 2- (ethylsulfonyl)-N-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-(2,2,2- trifluoroethyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(8-(2,2,3,3,3- pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)-N-(prop-2-yn-l-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; (2-(ethylsulfonyl)-3-(8-(2,2,3,3,3-pentafluoropropoxy)imidazo[l,5-a]pyrazin-3- yl)pyrazolo[ 1 ,5-a]pyrimidin-7-yl)(3-fluoroazetidin- 1 -yl)methanone; N-( 1 -cyanocyclopropyl)-2- (ethylsulfonyl)-3-(8-(2,2,3,3,3-pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; N-(cyanomethyl)-2-(ethylsulfonyl)-3-(8-(2,2,3,3,3- pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; ethyl 3- (2,2-difluoro-5-methyl-5H-[l,3]dioxolo[4',5':4,5]benzo[l,2-d]imidazol-6-yl)-2- (ethylsulfonyl)pyrazolo[l,5-a]pyrimidine-7-carboxylate; 3-(2,2-difluoro-5-methyl-5H-

[0219] [l,3]dioxolo[4',5':4,5]benzo[l,2-d]imidazol-6-yl)-2-(ethylsulfonyl)pyrazolo[l,5-a]pyrimidine-7- carboxylic acid; 3-(2,2-difluoro-5-methyl-5H-[l,3]dioxolo[4',5':4,5]benzo[l,2-d]imidazol-6-yl)-2- (ethylsulfonyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(l-cyanocyclopropyl)-2-(ethylsulfonyl)- 3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)-N- (l,l,l-trifluoropropan-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N,N- dimethyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-

[0220] 7-carboxamide; N-(l-cyclopropylethyl)-2-(ethylsulfonyl)-3-(8-(2,2,3,3,3- pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-allyl-2- (ethylsulfonyl)-3-(8-(2,2,3,3,3-pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-isopropyl-3-(8-(2,2,3,3,3- pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-N-methoxy-3-(8-(2, 2,3,3, 3-pentafluoropropoxy)imidazo[l, 5-a]pyrazin-3- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(cyclobutylmethyl)-2-(ethylsulfonyl)-3-(8-(2,2,3,3,3- pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-3-(8-(2,2,3,3,3-pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)-N-(2,2,3,3,3- pentafluoropropyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 3-(2,2-difluoro-5-methyl-5H-

[0221] [1.3]dioxolo[4',5':4,5]benzo[l,2-d]imidazol-6-yl)-N-ethyl-2-(ethylsulfonyl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; 3-(2,2-difluoro-5-methyl-5H-[l,3]dioxolo[4',5':4,5]benzo[l,2- d]imidazol-6-yl)-2-(ethylsulfonyl)-N-(2,2,2-trifluoroethyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 3-(2,2-difluoro-5-methyl-5H-[l,3]dioxolo[4',5':4,5]benzo[l,2-d]imidazol-6-yl)-N-(2,2-difluoroethyl)-

[0222] 2-(ethylsulfonyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 3-(2,2-difluoro-5-methyl-5H-

[0223] [1.3]dioxolo[4',5':4,5]benzo[l,2-d]imidazol-6-yl)-2-(ethylsulfonyl)-N-(2,2,3,3,3- pentafluoropropyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 3-(2,2-difluoro-5-methyl-5H-

[0224] [1.3]dioxolo[4',5':4,5]benzo[l,2-d]imidazol-6-yl)-2-(ethylsulfonyl)-N-(thietan-3-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; N-(cyanomethyl)-3-(2,2-difluoro-5-methyl-5H-

[0225] [1.3]dioxolo[4',5':4,5]benzo[l,2-d]imidazol-6-yl)-2-(ethylsulfonyl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; N-(l-cyanocyclopropyl)-3-(2,2-difluoro-5-methyl-5H-[l,3]dioxolo[4',5':4,5]benzo[l,2- d]imidazol-6-yl)-2-(ethylsulfonyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 3-(2,2-difluoro-5- methyl-5H-[l,3]dioxolo[4',5':4,5]benzo[l,2-d]imidazol-6-yl)-2-(ethylsulfonyl)-N- methoxypyrazolo[l,5-a]pyrimidine-7-carboxamide; (3-(2,2-difluoro-5-methyl-5H-

[0226] [1.3]dioxolo[4',5':4,5]benzo[l,2-d]imidazol-6-yl)-2-(ethylsulfonyl)pyrazolo[l,5-a]pyrimidin-7- yl)(3,3-difluoroazetidin-l-yl)methanone; N-ethoxy-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)- 3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-ethyl-2-(ethylsulfonyl)- N-methyl-3-(8-(2,2,3,3,3-pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)pyrazolo[l,5-a]pyrimidine- 7-carboxamide; N-(tert-butyl)-2-(ethylsulfonyl)-3-(8-(2,2,3,3,3-pentafluoropropoxy)imidazo[l,5- a]pyrazin-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-isobutyl-3-(8-

[0227] (2,2,3,3,3-pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(3,3-difluorocyclobutyl)-2-(ethylsulfonyl)-3-(8-(2,2,3,3,3-pentafluoropropoxy)imidazo[l,5- a]pyrazin-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-(l-methylcyclopropyl)-

[0228] 3-(8-(2,2,3,3,3-pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(ethylsulfonyl)-3-(8-(2,2,3,3,3-pentafluoropropoxy)imidazo[l,5-a]pyrazin-3-yl)-N- (l,l,l-trifluoropropan-2-yl)pyrazolo[l,5-a]pyrimidine -7-carboxamide; N-(allyloxy)-2-(ethylsulfonyl)- 3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; N-(benzyloxy)-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(tert-butoxy)-2-(ethylsulfonyl)-3-(3- methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(tert-butoxy)-2-(ethylsulfonyl)-3-(8-(2, 2,3,3, 3-pentafluoropropoxy)imidazo[l, 5-a]pyrazin-3- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 3-(2,2-difluoro-5-methyl-5H-

[0229] [1.3]dioxolo[4',5':4,5]benzo[l,2-d]imidazol-6-yl)-2-(ethylsulfonyl)-N-methylpyrazolo[l,5- a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-isopropoxy-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine -7-carboxamide; N-cyclopropyl-3-(2,2-difluoro- 5-methyl-5H-[l,3]dioxolo[4',5':4,5]benzo[l,2-d]imidazol-6-yl)-2-(ethylsulfonyl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; 3-(2,2-difluoro-5-methyl-5H-[l,3]dioxolo[4',5':4,5]benzo[l,2- d]imidazol-6-yl)-2-(ethylsulfonyl)-N-(prop-2-yn-l-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 3- (2,2-difluoro-5-methyl-5H-[l,3]dioxolo[4',5':4,5]benzo[l,2-d]imidazol-6-yl)-N-ethoxy-2- (ethylsulfonyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-

[0230] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-((tetrahydro-2H-pyran-2-yl)oxy)pyrazolo[l,5- a]pyrimidine-7-carboxamide; 3-(2,2-difluoro-5-methyl-5H-[l,3]dioxolo[4',5':4,5]benzo[l,2- d]imidazol-6-yl)-2-(ethylsulfonyl)-N-(l-methylcyclopropyl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(ethylsulfonyl)-N-isopropoxy-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(allyloxy)-2-(ethylsulfonyl)-3-(3-methyl- 6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(tert- butoxy)-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-((4-chlorobenzyl)oxy)-2-(ethylsulfonyl)-3-(3-methyl- 6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-((3- chlorobenzyl)oxy)-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-((2-chlorobenzyl)oxy)-2-(ethylsulfonyl)-3-(3-methyl- 6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)-N-((4- methylbenzyl)oxy)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)-N-((3-methylbenzyl)oxy)pyr azolof 1,5- a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- c]pyridin-2-yl)-N-((2-methylbenzyl)oxy)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)- N-((4-fluorobenzyl)oxy)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-((3-fluorobenzyl)oxy)-3-(3-methyl- 6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-N-((2-fluorobenzyl)oxy)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(benzyloxy)-2-(ethylsulfonyl)-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-((3- chlorobenzyl)oxy)-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-((3-methoxybenzyl)oxy)-3-(3- methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide;

[0231] 2-(ethylsulfonyl)-N-((4-methoxybenzyl)oxy)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-

[0232] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-phenethoxypyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(ethylsulfonimidoyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; methyl 2-(N-(2,2-difluoroacetyl)ethylsulfonimidoyl)-3- (3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxylate; methyl 3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-2-(N-(2,2,2- trifluoroacetyl)ethylsulfonimidoyl)pyrazolo[l ,5-a]pyrimidine-7-carboxylate; methyl 2-(N- acetylethylsulfonimidoyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate; 2-(ethylsulfonyl)-N-(2-methoxyethyl)-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-N-(2-(ethylthio)ethyl)-3-(3-methyl-6-(tifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-(3-methoxypropyl)-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-(2- (methylthio)ethyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-(2-hydroxy-2- methylpropyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; N-(2,2-difluoropropyl)-2-(ethylsulfonyl)-3-(3-methyl-6-

[0233] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-N-(l-methoxypropan-2-yl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-(2-hydroxypropyl)-3-

[0234] (3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N- (oxetan-2-ylmethyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; (S)-N-(2-ethyl-3-oxoisoxazolidin-4- yl)-2-(ethylsulfonyl)-3-(3-methyl-6-(tifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; (S)-N-(2-ethyl-3-oxoisoxazolidin-4-yl)-2-(ethylsulfonyl)-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-N-methoxy-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-ethoxy-2-(ethylsulfonyl)-3-(3-methyl-6-

[0235] (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; ethyl 2- (ethylsulfonyl)-2'-(trifluoromethyl)-[3,5'-bipyrazolo[l,5-a]pyrimidine]-7-carboxylate; N-(2- cyanopropan-2-yl)-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(dimethyl(oxo)-16-sulfaneylidene)-2-(ethylsulfonyl)- 3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(ethylsulfonyl)-2'-(trifluoromethyl)-[3,5'-bipyrazolo[l,5-a]pyrimidine]-7-carboxylic acid; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)-N-(2- (trifluoromethyl)cyclopropyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-2'-

[0236] (trifluoromethyl)-[3,5'-bipyrazolo[l,5-a]pyrimidine]-7-carboxamide; N-cyclopropyl-2-(ethylsulfonyl)- 2'-(trifluoromethyl)-[3,5'-bipyrazolo[l,5-a]pyrimidine]-7-carboxamide; N-(cyanomethyl)-2-

[0237] (ethylsulfonyl)-2'-(trifluoromethyl)-[3,5'-bipyrazolo[l,5-a]pyrimidine]-7-carboxamide; N-

[0238] (ethyl(methyl)(oxo)-16-sulfaneylidene)-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; methyl (2-(ethylsulfonyl)-3-(3- methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carbonyl)glycinate; N-(l-cyanocyclopropyl)-2-(ethylsulfonyl)-2'-(trifluoromethyl)-[3,5'- bipyrazolo[l,5-a]pyrimidine]-7-carboxamide; N-(2-cyanoethyl)-2-(ethylsulfonyl)-2'-(trifluoromethyl)- [3,5'-bipyrazolo[l,5-a]pyrimidine]-7-carboxamide; methyl (2-(ethylsulfonyl)-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carbonyl)glycinate; 2- (ethylsulfonyl)-N-(2,2,2-trifluoroethyl)-2'-(trifluoromethyl)-[3,5'-bipyrazolo[l,5-a]pyrimidine]-7- carboxamide; N-(allyloxy)-2-(ethylsulfonyl)-2'-(trifluoromethyl)-[3,5'-bipyrazolo[l,5-a]pyrimidine]- 7-carboxamide; ethyl (2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carbonyl)glycinate; 2-(ethylsulfonyl)-N-isopropoxy-2'-

[0239] (trifluoromethyl)-[3,5'-bipyrazolo[l,5-a]pyrimidine]-7-carboxamide; 2-(ethylsulfonyl)-N-methoxy-2'- (trifluoromethyl)-[3,5'-bipyrazolo[l,5-a]pyrimidine]-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)-N-(2-(methylamino)-2-oxoethyl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; methyl 1 -(2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamido)cyclopropane-l-carboxylate; N-(2-(tert-butylamino)-2-oxoethyl)-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; ethyl 2-(ethylsulfonyl)-3-(7- (trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate; 2- (ethylsulfonyl)-3-(7-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxylic acid; 2-(ethylsulfonyl)-N-methoxy-3-(7-(trifluoromethyl)-[l ,2,4]triazolo[l ,5-a]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-ethoxy-2-(ethylsulfonyl)-3-(7-(trifluoromethyl)- [l,2,4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonimidoyl)- 3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(N-cyanoethylsulfonimidoyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(2-(dimethylamino)-2-oxoethyl)-2- (ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-methoxy-3-(5-(2,2,3,3,3- pentafluoropropoxy)pyrazin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-ethoxy-2-

[0240] (ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(ethylsulfonyl)-N-methoxy-N-methyl-3-(5-(2, 2,3,3, 3 -pentafluoropropoxy )pyrazin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(5-(2,2,3,3,3- pentafluoropropoxy)pyrazin-2-yl)-N-(prop-2-yn-l-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; ethyl

[0241] 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-6-carboxylate; N-(allyloxy)-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3- pentafluoropropoxy)pyrazin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(5- (2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-N-(l-(trifluoromethyl)cyclopropyl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-isopropoxy-3-(5-(2,2,3,3,3- pentafluoropropoxy)pyrazin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; ethyl 2-(ethylsulfonyl)-

[0242] 3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6- carboxylate; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-6-carboxylic acid; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)- 3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(tert-butyl)-2-

[0243] (ethylsulfonyl)-3-(7-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; N-(cyclopropylmethoxy)-2-(ethylsulfonyl)-3-(5-(2, 2,3,3, 3 -pentafluoropropoxy )pyrazin- 2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-isobutoxy-3-(5-(2,2,3,3,3- pentafluoropropoxy)pyrazin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; (2-(ethylsulfonyl)-3-(5- (2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[l,5-a]pyrimidin-7-yl)(3-isopropoxyazetidin-l- yl)methanone; 2-(ethylsulfonyl)-N-(3-methyloxetan-3-yl)-3-(5-(2,2,3,3,3- pentafluoropropoxy)pyrazin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(cyanomethyl)-2- (ethylsulfonyl)-3-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(ethylsulfonyl)-N-methoxy-3-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N'-(tert-butyl)-2-(ethylsulfonyl)-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carbohydrazide; N-(2- cyanopropan-2-yl)-2-(ethylsulfonyl)-3-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(6-(trifluoromethyl)-

[0244] [1.2.4]triazolo[l,5-a]pyridin-2-yl)-N-(l-(trifluoromethyl)cyclopropyl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(ethylsulfonyl)-N-(l,l,l-trifluoro-2-methylpropan-2-yl)-3-(6-(trifluoromethyl)-

[0245] [1.2.4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(l-cyclopropylethyl)-

[0246] 2-(ethylsulfonyl)-3-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine- 7-carboxamide; 2-(ethylsulfonyl)-N-methoxy-N-methyl-3-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5- a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-(2,2,3,3,3- pentafluoropropyl)-3-(6-(trifluoromethyl)-[l, 2, 4]triazolo[l,5-a]pyridin-2-yl)pyr azolof 1,5- a]pyrimidine-7-carboxamide; N'-(tert-butyl)-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carbohydrazide; N-(2-cyanoethyl)-2- (ethylsulfonyl)-3-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; N-(cyclopropylmethoxy)-2-(ethylsulfonyl)-3-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5- a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-

[0247] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-(2,2,2-trifluoroethoxy)pyrazolo[l,5- a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- c]pyridin-2-yl)-N-(2,2,2-trifluoroethoxy)pyrazolo[l,5-a]pyrimidine-7-carboxamide; ethyl 7- cyclopropyl-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-6-carboxylate; ethyl 7-cyclopropyl-2-(ethylsulfonyl)-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l ,5-a]pyrimidine-6-carboxylate; ethyl 2- (ethylsulfonyl)-7-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-6-carboxylate; 7-cyclopropyl-2-(ethylsulfonyl)-3-(3-methyl-6-

[0248] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l ,5-a]pyrimidine-6-carboxylic acid; N- (tert-butoxy)-2-(ethylsulfonyl)-3-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; N-cyclopropyl-2-(ethylsulfonyl)-3-(6-(trifluoromethyl)-

[0249] [l,2,4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-7- methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6- carboxylic acid; N-cyclopropyl-2-(ethylsulfonyl)-7-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide; 2-(ethylsulfonyl)-3-(7- (trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2-yl)-N-(l-(trifluoromethyl)cyclopropyl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; N-cyclopropyl-2-(ethylsulfonyl)-3-(7-(trifluoromethyl)-

[0250] [l,2,4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N- isopropoxy-3-(7-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(ethylsulfonyl)-N-isobutoxy-3-(7-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-ethoxy-2-(ethylsulfonyl)-7-methyl-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l ,5-a]pyrimidine-6-carboxamide; ethyl 2- (ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate; ethyl 2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate; 2-

[0251] (ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylic acid; 2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylic acid; 2- (ethylsulfonyl)-N,N-dimethyl-3-(7-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; N-(dimethyl(oxo)-16-sulfaneylidene)-2-(ethylsulfonyl)-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-(4-oxido-l,416- oxathian-4-ylidene)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-ethoxy-2-(ethylsulfonyl)-3-(3- methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide; 2-(ethylsulfonyl)-N-(methyl(oxo)(phenyl)-16-sulfaneylidene)-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(benzyl(methyl)(oxo)-16- sulfaneylidene)-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-methyl-3-(3-methyl-6-

[0252] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide; N- cyclopropyl-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide; 2-(ethylsulfonyl)-N-isopropoxy-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide; N-ethyl- 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-6-carboxamide; N-(cyanomethyl)-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl- 6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-(2,2,2-trifluoroethyl)pyrazolo[l,5- a]pyrimidine-6-carboxamide; N-(cyclopropylmethyl)-2-(ethylsulfonyl)-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide; 2- (ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N- neopentylpyrazolo[l,5-a]pyrimidine-6-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-

[0253] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-(l-methylcyclopropyl)pyrazolo[l,5- a]pyrimidine-6-carboxamide; N-(l-cyanocyclopropyl)-2-(ethylsulfonyl)-3-(3-methyl-6-

[0254] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide; 2- (ethylsulfonyl)-N-methoxy-N-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide; 2-(ethylsulfonyl)-N-methoxy-3-(3-methyl-6-

[0255] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide; 2- (ethylsulfonyl)-N,N-dimethyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide; N-cyclopropyl-2-(ethylsulfonyl)-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide; 2- (ethylsulfonyl)-N-isopropoxy-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide; N,N-diethyl-2-(ethylsulfonyl)-3-(3-methyl-6-

[0256] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide; N-ethyl-

[0257] 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-6-carboxamide; N-ethoxy-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide; N-(cyanomethyl)-2-

[0258] (ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-6-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- c]pyridin-2-yl)-N-(l-methylcyclopropyl)pyrazolo[l,5-a]pyrimidine-6-carboxamide; 2-(ethylsulfonyl)- N-(methyl(oxo)(p-tolyl)-16-sulfaneylidene)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-3-(3-methyl-6-

[0259] (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)-N-neopentylpyrazolo[l,5-a]pyrimidine-6- carboxamide; N-(ethyl(methyl)(oxo)-16-sulfaneylidene)-2-(ethylsulfonyl)-3-(3-methyl-6-

[0260] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N- (diethyl(oxo)-16-sulfaneylidene)-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-cyclopropyl-2-(ethylsulfonyl)-6-methyl-

[0261] 3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; N-ethoxy-2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-ethyl-2-(ethylsulfonyl)-6-methyl-3-(3- methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; isobutyl (2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carbonyl)(methoxy)carbamate; 2-(ethylsulfonyl)-6-methyl-3-(3- methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-neopentylpyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(ethylsulfonyl)-N-methoxy-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l ,5-a]pyrimidine-7-carboxamide; isobutyl ethoxy(2- (ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carbonyl)carbamate; ethyl ethoxy(2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-

[0262] 3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carbonyl)carbamate; N-(2,2- difluoropropyl)-2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N,N,6-trimethyl-3-(3- methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(tert-butyl)-2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin- 2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(cyanomethyl)-2-(ethylsulfonyl)-6-methyl-3-(3- methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-(l- methylcyclopropyl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-methoxy-N,6- dimethyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine- 7-carboxamide; N-(dimethyl(oxo)-16-sulfaneylidene)-2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N,6-dimethyl-3-(3-methyl-6-

[0263] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; methyl 2- (ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate; 2-(ethylsulfonimidoyl)-N-methoxy-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; isobutyl (2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carbonyl)(methoxy)carbamate; ethyl (2-(ethylsulfonyl)-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carbonyl)(methoxy)carbamate; methyl (2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carbonyl)(methoxy)carbamate; N-

[0264] (cyclopropylmethoxy)-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonimidoyl)-N-methoxy-N-methyl-3-(3- methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-isopropyl-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-cyclopropyl-2-(ethylsulfonyl)-6-methyl-3-(3-methyl- 6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)-N- propylpyrazolo[l,5-a]pyrimidine-7-carboxamide; N-ethyl-2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(tert- butyl)-2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-methoxy-6-methyl-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(l- cyanocyclopropyl)-2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(cyclopropylmethyl)-2-(ethylsulfonyl)-6- methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin- 2-yl)-N-neopentylpyrazolo[l,5-a]pyrimidine-7-carboxamide; N-ethoxy-2-(ethylsulfonyl)-6-methyl-3- (3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(ethylsulfonyl)-N-isopropoxy-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-methoxy- N,6-dimethyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N,N,6-trimethyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(2-cyanopropan-2-yl)-2- (ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-(l-(hydroxymethyl)cyclopropyl)-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2- (ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N- propylpyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-isopropoxy-6-methyl-3-(3- methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyr azoIofl, 5-a]pyrimidine-7-carboxamide; ethyl l-(2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamido)cyclopropane-l-carboxylate; N-cyclopropyl-2-

[0265] (ethylsulfonimidoyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-

[0266] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-N-(2,2,2-trifluoroethyl)pyrazolo[l,5-a]pyrimidine- 7-carboxamide; N-ethyl-2-(ethylsulfonimidoyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-isopropyl-

[0267] 6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-

[0268] 7-carboxamide; N-(l-cyclopropylethyl)-2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)- 3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N- isobutyl-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide; N-(tert-butoxy)-2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-

[0269] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(l- cyanocyclopropyl)-2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-((l-cyanocyclopropyl)methyl)-2- (ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-ethoxy-2-(ethylsulfonimidoyl)-6-methyl-3-(3- methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-(cyclopropylmethyl)-2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; 2-(ethylsulfonyl)-N-(2-methoxyethyl)-6- methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; 2-(ethylsulfonyl)-N-methoxy-5-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; N-ethoxy-2-(ethylsulfonyl)-5- methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; N-ethoxy-2-(ethylsulfonyl)-7-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-5-carboxamide; N-cyclopropyl-2-(ethylsulfonyl)-5-methyl- 3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide; N-cyclopropyl-2-(ethylsulfonyl)-7-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-5-carboxamide; N-ethyl-2-(ethylsulfonyl)-3-(2- (trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyrimidin-5-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide; and 2-(ethylsulfonyl)-N-methyl-3-(2-(trifluoromethyl)imidazo[l,2-a]pyrimidin-7-yl)pyrazolo[l,5- a] pyrimidine-7 -carboxamide .

[0270] The compounds of the present invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and / or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and / or selectively prepare said stereoisomers. The compounds of the present invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.

[0271] An anion part of the salt in case the compound of formula (I) is a cationic or capable of forming a cation can be inorganic or organic. Alternatively, a cation part of the salt in case the compound of formula (I) is an anionic or capable of forming an anion can be inorganic or organic. Examples of inorganic anion parts of the salt include but are not limited to chloride, bromide, iodide, fluoride, sulfate, phosphate, nitrate, nitrite, hydrogen carbonates and hydrogen sulfate. Examples of organic anion part of the salt include but are not limited to formate, alkanoates, carbonates, acetates, trifluoroacetate, trichloroacetate, propionate, glycolate, thiocyanate, lactate, succinate, malate, citrates, benzoates, cinnamates, oxalates, alkylsulphates, alkylsulphonates, arylsulphonates aryldisulphonates, alkylphosphonates, arylphosphonates, aryldiphosphonates, p-toluenesulphonate, and salicylate. Examples of inorganic cation part of the salt include but are not limited to alkali and alkaline earth metals. Examples of organic cation part of the salt include but are not limited to pyridine, methyl amine, imidazole, benzimidazole, phosphazene, tetramethyl ammonium, tetrabutylammonium, choline and trimethylamine.

[0272] Metal ions in metal complexes of the compound of formula (I) are especially the ions of the elements of the second main group, especially calcium and magnesium, of the third and fourth main group, especially aluminium, tin and lead, and also of the first to eighth transition groups, especially chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Particular preference is given to the metal ions of the elements of the fourth period and the first to eighth transition groups. Here, the metals can be present in the various valencies that they can assume.

[0273] In one embodiment, the present invention provides a compound of formula (I), salts, metal complexes, stereoisomers, or N-oxides thereof and its composition with the excipient, inert carrier or any other essential ingredient such as surfactants, additives, solid diluents and liquid diluents.

[0274] Salts of the compounds of the formula (I) are preferably veterinary and / or agriculturally acceptable salts, preferably agriculturally acceptable salts. They can be formed in a customary manner, e.g. by reacting the compound with an acid of the anion in question if the compound of formula (I) has a basic functionality.

[0275] The term "N-oxide" includes any compound of formula (I) which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety.

[0276] The compounds of formula (I), (including all stereoisomers, N-oxides, and salts thereof), typically exist in more than one form, and formula (I) thus includes all crystalline and non-crystalline forms of the compounds that formula (I) represents. Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts. Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types). The term "polymorph" refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and / or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due to the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability. One skilled in the art will appreciate that a polymorph of a compound represented by formula (I) can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound represented by formula (I). Preparation and isolation of a particular polymorph of a compound represented by formula (I) can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures.

[0277] In an embodiment, the present invention provides a process for preparing the compound of formula (I) or salts thereof.

[0278] The compound of the present invention as defined by formula (I) may be prepared, in a known manner, in a variety of ways as described in the following schemes, in which, unless otherwise stated, the definition of each variable is as defined above for a compound of formula (I). The compound of formula (I) can be prepared according to schemes: 1-12 / chemistry examples described herein.

[0279] The process for preparing a compound of formula (Z), more specifically a compound of formula (Za) comprises reacting a compound of formula (2a), with a compound of formula (3), wherein M is NR10to obtain the compound of formula (Za). The process is summarized in scheme 1:

[0280] Scheme: 1 wherein, R1, R2, R3and n have the meanings as described above and A'= M, A4 and As= N or C.

[0281] The compound of formula (3) is either commercially available or can be prepared by using the methods known or analogously described in W0200665703, WO2009131237, WO2010125985, WO2011043404, WO2011040629, WO2012086848, WO2013018928 and W02015000715.

[0282] In scheme 1, the carboxylic acid group in the compound of formula (2a) can be converted to a more reactive functional group, such as an acyl halide, mixed anhydride, acyl azide, A- Acylbenzotriazoles, active esters, or via an in situ activation by peptide coupling reagents such as bis(2-oxo-3- oxazolidinyl)phosphinic chloride (BOP-CI); dicyclohexyl carbodiimide (DCC) or l-ethyl-3-(3- dimethylaminopropyl)carbodiimide (EDC), followed by amide bond formation with compound of formula (3) in solvents such as dichloromethane, dichloroethane, / V, / V-dimcthylacctamidc, tetrahydrofuran, acetonitrile or a mixture thereof to obtain a compound of formula (4). Organic non- nucleophilic bases such as triethyl amine, ethyldiisopropyl amine, pyridine, / V-mcthyl pyrrolidine, 1,8- diazabicyclo[5.4.0]undec-7-ene may be used. The reaction can be conducted at a temperature in the range of O °C to 150 °C.

[0283] The compound of formula (4) can be converted to a compound of formula (Za) by dehydration, following conventional or under microwave conditions, in the presence of an acid catalyst, for example, methane sulfonic acid, or para-toluene sulfonic acid, in an inert solvent such as / V-mcthyl pyrrolidine at a temperature in the range of 25 °C to 185 °C. Such processes have been described previously in WO2009131237, WO2010125985, WO2011043404, WO2011040629, WO2012086848,

[0284] WO2013018928, W02015000715 and WO2015121136.

[0285] Alternatively, the compound of formula (4) can be converted to a compound of formula (Za) wherein M is oxygen under Mitsunobu reaction conditions well known to those skilled in the art using diisopropyl azodicarboxylate, triphenyl phosphine in an inert solvent such as diethyl ether, tetrahydrofuran at a temperature in the range of 25 °C to 50 °C. This process is described previously in WO2009131237. The compound of formula (I) wherein Y=O or Y=NRYcan be obtained by sulfoxidation / sulfoximination of the corresponding sulfide compound of formula (Za) by using the analogous procedure as described in Org. Lett., 1999, 1, 189-191; J. Am. Chem. Soc., 2006, 128, 6012- 6013; Tetrahedron Lett. 2005, 46, 8007-8008 and W02015071180A1.

[0286] Scheme 2 provides a process for preparing a compound of formula (Zb):

[0287] Scheme: 2 wherein, R1, R2, R3and n have the meanings as described above and Ai= N or C.

[0288] The carboxylic acid of formula (2a) can be converted to the Weinreb amide of formula (5) upon reaction with N, O-dimethylhydroxylamine by methods as described in WO201175643 and EP2671582. Subsequent treatment of the Weinreb amide of formula (5) with Grignard reagents of formula (R’CHzMgHal) according to the method described in Tetrahedron Letters 1981, 22, 3815 to obtain a compound of formula (6).

[0289] Cyclization of the compound of formula (6) to obtain the compound of formula (Zb) using an amine of formula (7) can be effected in the presence of a Lewis acid, such as Indium (III) triflate or Zinc (II) iodide, in solvents such as 1,2 -dichlorobenzene, chlorobenzene, in the presence of catalytic copper (II) salts, such as copper (II) acetate, under oxygen or air atmosphere. The reaction can be carried out at a temperature in the range of 100 °C to 180 °C. Such reaction has precedence in the literature, for example in (Adv. Synth. Catalysis, 2013, 355, 1741; J. Org. Chem, 2013, 78, 12494).

[0290] Alternatively, the compound of formula (6) can be converted to a compound of formula (8) wherein X is a halogen (preferably chlorine or bromine) with a halogenating agent such as / V-chloro succinimide, / V-bromo succinimide, / V-iodo succinimide, E, CuB . B in acetic acid or PhNMe3+Br3 , typically in a solvent such as methanol, acetonitrile, tetrahydrofuran, ethylacetate, chloroform or dichloromethane, or mixtures thereof, at a temperature in the range of 0 °C to 150 °C, preferably between 25 °C to 120 °C, optionally under microwave heating conditions. Such processes have been described previously, for example, in W02016 / 071214. The compound of formula (Zb) can be obtained by condensing the compound of formula (8) with compounds of formula (7), in an inert solvent, for example, ethanol or acetonitrile, optionally in the presence of a suitable base, such as sodium, potassium or cesium carbonate, at a temperature in the range of 80 °C to 150 °C, optionally under microwave heating conditions. Such processes have been described previously, for example, in W02003 / 031587. The compound of formula (7) is either commercially available or may be prepared by known methods to those skilled in the art.

[0291] The compound of formula (I) wherein Y=O or Y=NRYcan be obtained by sulfoxidation / sulfoximination of the corresponding sulfide compound of formula (Zb) by using the analogous procedure as described in Org. Lett., 1999, 1, 189-191; J. Am. Chem. Soc., 2006, 128, 6012- 6013; Tetrahedron Lett. 2005, 46, 8007-8008 and W02015071180A1.

[0292] Scheme 3 provides a process for preparing a compound of formula (Zc) and (Zd):

[0293] Scheme: 3 wherein, Ai = N or C, R1, R2, R3and n have the meanings as described above.

[0294] The compound of formula (Zc) can be prepared by reacting a compound of formula (9) with a compound of formula (11), optionally in the presence of a suitable base and in an inert solvent. The compound of formula (Zd) can be prepared by reacting a compound of formula (10), in which Y is a halide ion or mesityl sulfonate with the compound of formula (11), optionally in the presence of a suitable base and in an inert solvent.

[0295] The compound of formula (9) or (10) can be prepared via / V-ami nation by reacting the compound of formula (7) <7> with O-mesitylenesulfonylhydroxylamine (MSH) as an amination reagent or one of its equivalent, as described for example in WO201334506.

[0296] The compound of formula (I) wherein Y=O or Y=NRYcan be obtained by sulfoxidation / sulfoximination of the corresponding sulfide compound of formula (Zc) or (Zd) by using the analogous procedure as described in Org. Lett., 1999, 1, 189-191; J. Am. Chem. Soc., 2006, 128, 6012-6013; Tetrahedron Lett. 2005, 46, 8007-8008 and W02015071180A1.

[0297] Schemes 4 to 11 provide processes for the preparation of pyrzolo pyrimidine. A process for the synthesis of a compound of formula (2aa-2ab) is depicted in scheme 4:

[0298] Scheme: 4 wherein, R1and R2have the meanings as described above.

[0299] The compound of formula (2aa) depicted in scheme-4 can be prepared from the pyrazole derivative of formula (12) using alken-one reagents of formula (13) under cyclocondensation conditions, in the presence of a solvent or an acid. Examples of the acids include acetic acid, sulfonic acid (e.g. PTSA), sulfuric acid, and hydrochloric acid which liberate the reactive functional group. Examples of the solvents include but are not limited to methanol, ethanol, isopropanol or ethylene glycol or the like. The reaction can be carried out at a temperature in the range of 0 °C to 150 °C. The preparation of the compound of formula (12) has been described in the literature such as Journal of Heterocyclic Chemistry 2016, 53, 1231.

[0300] In a similar way, a compound of formula (2ab) depicted in scheme-4 can be prepared from the pyrazole derivative of formula (12) using protected 2-formyl-3-oxopropanoic acid of formula (15) in the presence of a solvent like ethanol, 2-propanol and in the presence of an acid such as acetic acid. The reaction can be carried out at a temperature in the range of 50 °C to 130 °C.

[0301] The compound of formula (2aa) can be obtained through acid hydrolysis of the cyano functional group of the compound of formula (14). Examples of an acid include sulfuric acid or hydrochloric acid and the reaction can be carried out at a temperature in the range of 60 °C to 150 °C.

[0302] A process for the synthesis of a compound of formula (20a-b) is depicted in the scheme 5a:

[0303] Scheme: 5a wherein, R1has the meanings as described above

[0304] The pyrazole derivative of formula (17 or 12) can undergo a cyclocondensation reaction when treated with a dielectrophilic compound of formula (18) or it’s protected / masked (e.g. aldehyde masked as a ketal) version to provide a compound of formula (19). The condensation can be carried out in a solvent and in the presence of an acid. Examples of an acids include but are not limited to acetic acid, sulfonic acid (e.g. PTSA), sulfuric acid or hydrochloric acid which liberate the reactive functional group. Examples of the solvents include but are not limited to methanol, ethanol, isopropanol or ethylene glycol or the like. The reaction can be carried out at a temperature in the range of 0 °C to 150 °C.

[0305] The conversion of the compound of formula (19) to the compound of formula (20) can be carried out in a solvent, in the presence of a halogenating agent and in the presence or absence of a base. Examples of the solvent include but are not limited to acetonitrile, chloroform, tetrahydrofuran, 1,4-dioxane, toluene or A,A-dimethylformamide or the like. Examples of halogenating agents include but are not limited to phosphorus oxychloride, thionyl chloride, phosphorus pentachloride or oxalyl chloride or the like. Examples of the base include but are not limited to A,A-dimethylaniline, diisopropylethylamine or / V- methyl morpholine or the like. The reaction can be carried out at a temperature in the range of 50 °C to 200 °C.

[0306] A process for the synthesis of a compound of formula (22a-b) is depicted in the scheme 5b:

[0307] Scheme: 5b wherein, R1and X have the meanings as described above.

[0308] The compound of formula (22) can be prepared by the cyclization of the pyrazole derivative of formula (17 or 12) with commercially available 2-halo-malonaldehydes of formula (21) under acid catalyzed conditions. Examples of an acids include but are not limited to acetic acid, sulfonic acid (e.g PTSA), sulfuric acid, and hydrochloric acid. Examples of the solvents include but are not limited to methanol, ethanol, isopropanol, ethyleneglycol or the like. The reaction can be carried out at a temperature in the range of 0 °C to 150 °C.

[0309] A process for the synthesis of a compound of formula (26a-b) is depicted in the scheme 5c:

[0310] Scheme: 5c wherein, R1and X have the meanings as described above. The pyrazole derivative of formula (17 or 12) can undergo a cyclocondensation with 1,3 -dimethyluracil of formula (23) or alkoxyacrylate derivatives of formula (24) in the presence of a suitable base to obtain pyrimidin-5-one derivatives of formula (25). Examples of the suitable base include sodium ethoxide, sodium methoxide, potassium tert-butoxide, potassium carbonate, sodium carbonate, cesium carbonate or potassium phosphate or the like. Examples of the solvent include methanol, ethanol, isopropanol, ethyleneglycol, / V, / V-dimcthylacctamidc or / V, / V-dinicthylfornianiidc or the like. The reaction can be carried out at a temperature in the range of 50 °C to 150 °C. Such a reaction is well known in the literature, and also alternative reactions are well described in the literature, for example, J. Org. Chem 2007, 72, 1046; WO2018081417. Halogenation of a compound of formula (25) with phosphorous oxychloride or phosphorous oxybromide can provide a compound of formula (26).

[0311] Scheme: 6 wherein, R1and X have the meanings as described above.

[0312] Compounds of formula (27-29) can be prepared from the halide compounds of formula (20 / 22 / 26) by a palladium catalysed carbonylation reaction, in the presence of a suitable palladium catalyst, organic base and suitable alcohol solvent at elevated temperature under an atmosphere of CO. When R” is methyl or ethyl or n-butyl or tert-butyl in the compound of formula (27 / 28 / 29), the preferred reaction condition comprises reaction of the bromide of formula (20 / 22 / 26) under an atmosphere of CO, pressure ranges vary from 1 bar to 20 bar in the presence of a suitable palladium catalyst such as Pd(dppf)C12, PdC12(ACN)2, PdC12(PhCN)2 or Pd(OAc)2, using a catalyst such as triphenyl phosphine or diphenyl phosphino ferrocene or 1,3-diphenyl phosphino propane or 1,3-dicylcohexyl phosphino propane, in the presence of an organic base such as triethyl amine or diisopropyl ethyl amine or DBU, in a solvent such as MeOH or EtOH or nBuOH or tBuOH and at a temperature in the range of 80 °C to 130 °C. Such kind of transformations are precedent in the literature such as in Angew. Chem., Int. Ed. 2009, 48, 4114.

[0313] Alternatively, when R” is phenyl or phenyl derivatives, compounds of formula (27 / 28 / 29) may be prepared from the halide compounds of formula (20 / 22 / 26) by a palladium catalyzed reaction with CO surrogates such phenyl formate or formate of any active phenyl derivatives such as 2,4,6- trichlorophenyl, in the presence of a suitable palladium catalyst such as Pd(OAc)2 with a phosphinebased ligand such as BINAP or XantPhos or XPHOS, in the presence of a base such as N,N- diethylethanamine or triethyl amine, in a solvent such as MeCN, toluene or xylene and at a temperature in the range of 80 to 130 °C. Such reactions are precedent in the literatures such as as in Org. Lett. 2012, 20, 5370; Angew. Chem., Int. Ed. 2004, 43, 5580; Modem Carbonylation Methods', Kollar, L. Ed.; 2008, pp 93-114.

[0314] Ester hydrolysis of formula (27-29) can be carried out selectively with respect to the group R’. Alkaline hydrolysis can be carried out using a base such as sodium hydroxide, potassium hydroxide, lithium hydroxide or Bis(tributyltin) oxide or the like; in the solvent such as tetrahydrofuran, water, methanol, ethanol, toluene or a mixture thereof, to obtain the compounds of formula (2aa / 2ab / 2ac). Acidic hydrolysis can be carried out using an acid such as hydrochloric acid or acetic acid or trifluoro acetic acid, in the presence of a solvent such as dichloromethane, 1 ,2-dichlorethane, toluene, xylene or dioxane, at a temperature in the range of 0 to 100 °C to obtain the compound of formula (2aa / 2ab / 2ac).

[0315] Scheme: 7 wherein, R1and Q have the meanings as described above

[0316] A process for the synthesis of a compound of formula (33a-c) and (Z-1) is depicted in the scheme-7. Organo sulfanylalkenes of formula (31) can be formed by reacting a cyano compound of formula (30) with CS2 in the presence of a base such as alkali metal carbonates, alkali metal hydrides, lithium, sodium or potassium hexamethyl disilazane, sodium or potassium hydroxide, in a suitable solvent such as tetrahydrofuran, acetonitrile or / V, / V-dimcthylfromamidc, at a temperature in the range of 0 to 50 °C. The compound of formula (31) can be cyclized to an aminopyrazole derivative of formula (32) using hydrazine. Such method is described in the literature, for example, Russian Journal of Organic Chemistry, 2014, 50(3), 412-421. The aminopyrazole derivative can be converted to the compound of formula (33a-c) using the methods described in scheme 5a (Steps 1&2) or scheme 5b (Step 2 or Step 5) or scheme 5c (Steps 1&2).

[0317] The compound of formula (Z-1) can be prepared by reacting the compound of formula (33a-c) using the conditions described in step-1 of scheme-6.

[0318] Ester hydrolysis of formula (Z-1) can be carried out selectively with respect to the group R”. Alkaline hydrolysis can be carried out using a base such as sodium hydroxide, potassium hydroxide, lithium hydroxide or Bis(tributyltin) oxide or the like; in a suitable solvent such as tetrahydrofuran, water, methanol, ethanol or toluene or mixtures thereof, to obtain the corresponding carboxylic acids. Acidic hydrolysis can be carried out using an acid such as hydrochloric acid, acetic acid or trifluoro acetic acid, in the presence of a suitable solvent such as dichloromethane, 1 ,2-dichlorethane, toluene, xylene or dioxane, at a temperature in the range of 0 to 100 °C to obtain the corresponding carboxylic acids.

[0319] Scheme: 8

[0320] The compound of formula (Z-2) can be prepared according to scheme-8 by cyclocondensing the pyrazole derivative of formula (32) and keto ester compound of formula (34) with dimethylformamide - dimethylacetal or triethyl orthoformate or the like, in the presence of a suitable solvent such as ethanol or acetic acid, at a temperature in the range of 60 to 150 °C.

[0321] Scheme: 9

[0322] The compound of formula (32) can be condensed with pyruvates of formula (35) according to scheme- 9, in the presence of a suitable solvent such as ethanol or methanol, at a temperature in the range of 60 to 150 °C to provide a separable mixture of regio isomers (Z-3) and (Z-4). Alternatively, the same product can be prepared by carrying the reaction in the presence of an acid such as hydrochloric acid or acetic acid at a temperature in the range of 60 to 150 °C.

[0323] Scheme: 10

[0324] The compound of formula (32) can be condensed with olefines of formula (36) according to scheme- 10, in the presence of a suitable solvent such as ethanol or methanol, at a temperature in the range of 60 to 150 °C to provide compounds of formula (Z-T) or (Z-2’). Alternatively, the same product can be prepared by carrying the reaction in the presence of an acid such as hydrochloric acid or acetic acid at a temperature in the range of 60 to 150 °C.

[0325] Scheme: 11 wherein, Q, R1, R2and R2ahave the meanings as described above.

[0326] The compound of formula (1-1) wherein m=l (sulfoxide) and / or m=2 (sulfone), can be obtained by the oxidation of the corresponding sulfide compound of formula (Z) while applying appropriate oxidizing agents and conditions well known to those skilled in the art. Oxidizing agents such as m- chloroperoxybenozic acid (mCPBA), hydrogenperoxide / glacial acetic acid, hydrogenperoxide / trifluroacetic acid, hydrogenperoxide / potassium permanganate, hydrogenperoxide / p-toluenesuflonylimidazole, urea hydrogen peroxide / trifluoroacetic acid, oxone, sodium periodate, sodium hypochlorite or other organic peracids or the like can be used for this, at a temperature in the range of 0 to 100 °C. Examples of the solvent used in this reaction include aliphatic halogenated hydrocarbons such as dichloromethane, chloroform, alcohols such as methanol or ethanol or the mixtures thereof.

[0327] Scheme: 12 wherein, Q, R1R2, R2aand RYhave the meanings as described above and R2acan be absent also.

[0328] The compound of formula (1-2) wherein RY= H, can be obtained by reacting the compound of formula (Z) with a suitable nitrogen source, such as, for example, ammonia, ammonium carbamate or ammonium acetate, in the presence of hypervalent iodine reagents, such as diacetoxyiodobenzene PhI(OAc)2, in a suitable solvent such as toluene, acetonitrile or alcohols (preferably methanol, 2,2,2- trifluoromethanol or 2,2,3,3,4,4,5,5-octafluorpentan-l-ol, among others), at a temperature in the range of 0 to 100 °C, preferably around 25 °C.

[0329] The compound of formula (1-3) wherein RYis other than ‘H’ can be prepared using a reagent RY-X, wherein X is a leaving group, for example, halides such as chloro, bromo or iodo, or an aryl or alkylsulfonate such as trifluoromethanesulfonate. Alkylation reaction can be performed in the presence of base such as sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, cesium carbonate or triethylamine and in the presence of suitable solvents such as dichloromethane, dichloroethane, DMF, DMSO, ethanol or methanol and at a temperature in the range of 0 to 150 °C. Metal catalyzed coupling for the preparation of compounds of formula (1-3; RY= other than ‘H’) can be performed in the presence of a base, such as potassium carbonate, sodium carbonate, cesium carbonate or sodium hydroxide, in an inert solvent, such as toluene, DMF, N-methyl pyrrolidine (NMP), DMSO, dioxane or THF or the like, optionally in the presence of a catalyst, for example palladium(II)acetate, his(dibenzylideneacetone)palladium(0) (Pd(dba)2), tris(dibenzylideneacetone)dipalladium(0) (Pdz(dba)3 optionally in form of its chloroform adduct, or a palldium pre-catalyst such as for example tert-BuBrettPhos Pd G3 [(2 Di-tert-butylphosphino-3,6- dimethoxy-2 ’ ,4 ’ ,6 ’ -triisopropyl- 1,1’ -biphenyl)-2-(2 ’ -amino- 1,1’ -biphenyl)]palladium(II) methanesulfonate or BrettPhos Pd G3 [(2-di-cyclohexylphosphino-3,6-dimethoxy-2’,4’,6’- triisopropyl- 1,1’ -biphenyl)-2-(2 ’ -amino- 1,1’ -biphenyl)]palladium(II) methanesulfonate, and optionally in the presence of a ligand, for example SPhos, t-BuBrettPhos or XantPhos, at a temperature in the range of 50 to 120 C°, optionally under microwave heating conditions.

[0330] CHEMISTRY EXAMPLES:

[0331] The following examples set forth the manner and process of making compounds of the present invention without being a limitation thereof and include the best mode contemplated by the inventors for carrying out the invention.

[0332] Example-1: Synthesis of 2-(ethylsulfonyl)-N-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (Compound-02)

[0333] Step-1: Synthesis of 2-Cyano-A-(2-(methylamino)-5-(trifluoromethyl)pyridin-3-yl)acetamide

[0334] To a stirred solution of 2-cyanoacetic acid (33.4 g, 392 mmol) in dichloromethane (300 mL), l-(3- dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (48.1 g, 251 mmol) and N,N- diisopropylethylamine (82 mL, 471 mmol) were added and stirred at 0 °C for 0.5 h followed by the addition of A-2-methyl-5-(trifluoromethyl)pyridine-2,3-diamine (30.0 g, 157 mmol) at 0 °C. The resulting reaction mixture was stirred at 25 °C for 24 h under nitrogen atmosphere. After the completion of the reaction, the reaction mixture was concentrated and diluted with water (500 L). The aqueous layer was extracted with ethyl acetate (4 x 250 L). The combined organic layers were washed with water (250 mL), brine (250 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a residue which was further washed with hexane to obtain 2-cyano-A-(2- (methylamino)-5-(trifluoromethyl)pyridin-3-yl)acetamide (39 g, 151 mmol; 96 % yield). 'H-NMR (400 MHz, DMSO-c / r,) 3 9.63 (s, 1H), 8.26 (d, J = 1.0 Hz, 1H), 7.64 (d, J = 2.2 Hz, 1H), 6.96 (d, J = 4.6 Hz, 1H), 3.85 (s, 2H), 2.87 (d, J = 4.6 Hz, 3H); ESI MS (m / z) 258.95 (MH)+.

[0335] Step-2: Synthesis of 2-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)acetonitrile A solution of 2-cyano-A-(2-(methylamino)-5-(trifluoromethyl)pyridin-3-yl)acetamide (39 g, 151 mmol) in acetic acid (230 mL) was heated at 110 °C for 2 h. After the completion of the reaction, the reaction mixture was evaporated under reduced pressure and diluted with ethyl acetate (250 mL) and water (250 mL). The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain a crude product which was further washed with hexane to obtain 2-(3-methyl- 6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)acetonitrile (31 g, 129 mmol; 85 % yield). 'H-NMR (400 MHz, DMSO-cL) 3 8.74 (d, J = 1.2 Hz, 1H), 8.54 (d, J = 1.7 Hz, 1H), 4.67 (s, 2H), 3.80 (s, 3H); ESI MS (m / z) 241.10 (MH)+.

[0336] Step-3: Synthesis of 3,3-bis(ethylthio)-2-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)acrylonitrile

[0337] To a mixture of potassium hydroxide (KOH) (17.0 g, 258 mmol) in acetonitrile (300 mL), 2-(3-methyl- 6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)acetonitrile (31 g, 129 mmol) was added at 0 °C. The resulting reaction mixture was stirred at 25 °C for 1 h and then cooled to 0 °C, followed by dropwise addition of carbon disulfide (8.60 mL, 142 mmol) over 10 minutes. The resulting reaction mixture was stirred at 0 °C for 1 h and then ethyl iodide (20.80 mL, 258 mmol) was added at the same temperature in a dropwise manner over 15 minutes. The resulting reaction mixture was stirred at 0 °C for 2 h and then warmed to 25 °C and stirred further at the same temperature for 12-15 h. After the completion of the reaction, the reaction mixture was evaporated under reduced pressure to obtain a crude compound which was purified by flash column chromatography to obtain 3,3-bis(ethylthio)-2-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)acrylonitrile (41 g, 110 mmol; 85 % yield). 'H-NMR (400 MHz, DMSO-<76) 3 8.84 (d, J = 1.5 Hz, 1H), 8.62 (d, J = 1.7 Hz, 1H), 3.87 (s, 3H), 3.25 (q, J = 7.3 Hz, 2H), 2.84 (q, J = 7.3 Hz, 2H), 1.36 (t, J = 7.3 Hz, 3H), 1.14 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 473.00 (MH)+.

[0338] Step-4: Synthesis of 3-(Ethylthio)-4-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)-lH-pyrazol-5-amine

[0339] To a stirred solution of 3,3-bis(ethylthio)-2-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin- 2-yl)acrylonitrile (34.0 g, 91 mmol) in acetonitrile (150 mL) and ethanol (300 mL), hydrazine monohydrate (5.40 mL, 110 mmol) was added dropwise at 0 °C. The resulting reaction mixture was stirred at 0 °C for 1 h and then ice-cold water was added to the reaction mixture. The solid obtained was filtered and purified by flash column chromatography to obtain 3-(ethylthio)-4-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-lH-pyrazol-5-amine (16 g, 46.7 mmol; 51.2 % yield). ’H-NMR (400 MHz, DMSO-t6) 3 12.00 (s, 1H), 8.68 (s, 1H), 8.39 (s, 1H), 5.73 (s, 2H), 3.76 (s, 3H), 2.88 (q, J = 7.1 Hz, 2H), 1.21-1.14 (m, 3H); ESI MS (m / z) 343.40 (MH)+.

[0340] Step-5: Synthesis of Ethyl 2-(ethylthio)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate To a stirred solution of 3-(ethylthio)-4-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)- lH-pyrazol-5-amine (3 g, 8.7 mmol) in acetic acid (40 mL), ethyl (E)-4-ethoxy-2-oxobut-3-enoate (2.26 g, 13.1 mmol) was added. The resulting reaction mixture was stirred at 110 °C for 4.5 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C, the reaction mixture was concentrated under reduced pressure to obtain a residue, which was suspended in ice cold water and stirred for 0.5 h. The solid obtained was filtered, washed with ice cold water (500 mL) followed by hexane (250 mL) and dried to obtain ethyl 2-(ethylthio)-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate (2.2 g, 4.8 mmol, 55.7 % yield). 'H-NMR (400 MHz, CHLOROFORM-tf) 5 8.68 (q, J = 0.9 Hz, 1H), 8.63 (d, J = 4.4 Hz, 1H), 8.36 (d, J = 1.5 Hz, 1H), 7.34 (d, J = 4.4 Hz, 1H), 4.60 (q, J = 7.2 Hz, 2H), 4.01 (d, J = 14.4 Hz, 3H), 3.36-3.30 (m, 2H), 1.53-1.46 (m, 6H); ESI MS (m / z) 450.70 (MH)+1.

[0341] Step-6: Synthesis of 2-(Ethylthio)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylic acid

[0342] To a stirred solution of ethyl 2-(ethylthio)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin- 2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate (2 g, 4.4 mmol) in tetrahydrofuran (40 mL), lithium hydroxide, monohydrate (0.75 g, 17.7 mmol) in water (6.0 mL) was added. The resulting reaction mixture was stirred at 25 °C for 3 h. After the completion of the reaction, the reaction mixture was diluted with water (20 mL) and neutralized to pH=4 with IN HC1 solution. The aqueous layer was extracted with ethyl acetate (3 x 25 mL). The combined organic layers were dried over anhydrous sodium sulphate, evaporated under reduced pressure to obtain a crude 2-(ethylthio)-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l ,5-a]pyrimidine-7-carboxylic acid (1.6 g, 3.8 mmol, 85 % yield), which was used in the next step without any purification.1H-NMR (400 MHz, DMSO-<76) 5 8.78-8.77 (m, 2H), 8.55 (t, J = 1.1 Hz, 1H), 7.47 (d, J = 4.3 Hz, 1H), 3.91 (d, J = 14.7 Hz, 3H), 3.24-3.18 (m, 2H), 1.40-1.33 (m, 3H); ESI MS (m / z) 423.08 (MH)+.

[0343] Step-7: Synthesis of 2-(Ethylthio)-N-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide

[0344] To a stirred solution of 2-(ethylthio)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylic acid (300 mg, 0.7 mmol) in / V, / V-dimcthyl formamide (5 mL), pyridine (0.46 mL, 5.7 mmol), 1 -propylphosphonic anhydride (0.63 mL, 1.06 mmol) and methanamine (0.89 mL, 1.8 mmol) were added at 0 °C. The resulting reaction mixture was stirred at 25 °C for 16 h. After the completion of the reaction, the reaction mixture was diluted with ice cold water (20 mL). The precipitate obtained was filtered, washed with diethyl ether (2 x 5 mL) and dried to obtain 2-(ethylthio)-A-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide (250 mg, 0.6 mmol, 81 % yield). 'H-NMR (400 MHz, DMSO-cL) 5 9.59 (d, J = 4.9 Hz, 1H), 8.83 (d, J = 4.4 Hz, 1H), 8.78 (d, J = 1.2 Hz, 1H), 8.56 (d, J = 1.5 Hz, 1H), 7.61 (d, J = 4.4 Hz, 1H), 3.92 (s, 3H), 3.27 (t, J = 7.3 Hz, 2H), 3.01 (d, J = 4.9 Hz, 3H), 1.40-1.34 (m, 3H); ESI MS (m / z) 435.55 (MH)+.

[0345] Step-8: Synthesis of 2-(Ethylsulfonyl)-N-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide

[0346] To a stirred solution of 2-(ethylthio)-A-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (160 mg, 0.4 mmol) in dichloromethane (15 mL), m-chloroperbenzoic acid (244 mg, 0.9 mmol) was added at 0 °C. The reaction mixture was stirred at 25 °C for 16 h. After the completion of the reaction, the reaction mixture was quenched with sodium thiosulphate solution (120 mL) and extracted with dichloromethane (4 x 10 mL). The combined organic layers were washed with aqueous NaHCCL solution (120 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain a crude compound which was purified by flash column chromatography to obtain 2-(ethylsulfonyl)-A-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (95 mg, 0.2 mmol, 55.3 % yield) as a white solid. ’H-NMR (400 MHz, DMSO-J6) 5 9.31 (d, J = 4.9 Hz, 1H), 8.98 (d, J = 4.2 Hz, 1H), 8.86 (t, J = 1.0 Hz, 1H), 8.63 (d, J = 1.5 Hz, 1H), 7.83 (d, J = 4.4 Hz, 1H), 3.81-3.76 (m, 5H), 3.01 (d, J = 4.6 Hz, 3H), 1.26 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 467.10 (MH)+1.

[0347] Example-02: Synthesis 2-(Ethylsulfonyl)-N-methyl-3-(6-(trifluoromethyl)imidazo[l,2-a]pyridin- 2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (Compound-23)

[0348] Step-1: Synthesis of 2-(Chloromethyl)-6-(trifluoromethyl)imidazo[l,2-a]pyridine

[0349] To a stirred solution of 5-(trifluoromethyl)pyridin-2-amine (13.0 g, 80.0 mmol) in ethanol (150 mL), l,3-dichloropropan-2-one (20.36 g, 160.0 mmol) was added, and the resulting reaction mixture was stirred at 90 °C for 24 h. After the completion of the reaction, the reaction mixture was poured into aqueous saturated sodium bicarbonate (400 mL) solution. The aqueous layer was extracted with ethyl acetate (2 X 200 mL). The combined organic layers were washed with brine solution (200 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain a crude product which was purified by flash column chromatography to obtain 2-(chloromethyl)-6- (trifluoromethyl)imidazo[l,2-a]pyridine (10.54 g, 44.9 mmol, 56 % yield) as a liquid. 'H-NMR (400 MHz, CHLOROFORM-t / ) 3 8.46 (td, J = 2.1, 1.1 Hz, 1H), 7.72 (d, J = 0.5 Hz, 1H), 7.67 (dd, J = 9.5, 0.7 Hz, 1H), 7.34 (dd, J = 9.5, 1.7 Hz, 1H), 4.76 (d, J = 0.5 Hz, 2H); ESI MS (m / z) 235.80 (MH)+.

[0350] Step-2: Synthesis of 2-(6-(Trifluoromethyl)imidazo[l,2-a]pyridin-2-yl)acetonitrile

[0351] To a stirred solution of 2-(chloromethyl)-6-(trifluoromethyl)imidazo[l,2-a]pyridine (18.0 g, 77.0 mmol) in acetonitrile (180 mL), trimethylsilyl cyanide (15.43 mL, 115.0 mmol) and tetra butyl ammonium fluoride (115 mL, 115.0 mmol) were added. The resulting reaction mixture was stirred at 25 °C for 48 h. After the completion of the reaction, the reaction mixture was poured into water (300 mL). The aqueous layer was extracted with ethyl acetate (3 x 100 mL), the combined organic layers were washed with saturated brine solution (50 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain a crude product which was purified by flash column chromatography to obtain the desired 2-(6-(trifluoromethyl)imidazo[l,2-a]pyridin-2-yl)acetonitrile (14.2 g, 63.1 mmol, 82 % yield) as solid. 'H-NMR (400 MHz, DMSO-t6) 3 8.50-8.49 (m, 1H), 7.76 (d, J = 0.7 Hz, 1H), 7.67 (d, J = 9.5 Hz, 1H), 7.38 (dd, J = 9.4, 1.8 Hz, 1H), 3.96 (d, J = 0.7 Hz, 2H); ESI MS (m / z) 226.0 (MH)+.

[0352] Step-3: Synthesis of 3,3-bis(ethylthio)-2-(6-(trifluoromethyl)imidazo[l,2-a]pyridin-2- yl)acrylonitrile

[0353] To a stirred solution of potassium hydroxide (7.47 g, 133 mmol) in acetonitrile (300 mL) at 25 °C, 2- (6-(trifluoromethyl)imidazo[l,2-a]pyridin-2-yl)acetonitrile (15.0 g, 66.6 mmol) was added. The resulting reaction mixture was stirred for 1 h at 25 °C and it was cooled to -5 °C followed by dropwise addition of carbon disulfide (4.0 mL, 66.6 mmol) over 10 minutes. The resulting reaction mixture was stirred for 1 h at -5 °C and then ethyl iodide (10.8 mL, 133.0 mmol) was added in a dropwise manner over 15 minutes. The reaction mixture was stirred for 2 h at 0 °C and then at 25 °C for 16 h. After the completion of the reaction, the volatiles were evaporated under reduced pressure to get a crude product which was purified by flash column chromatography to obtain 3,3-bis(ethylthio)-2-(6- (trifluoromethyl)imidazo[l ,2-a]pyridin-2-yl)acrylonitrile (17.14 g, 48.0 mmol, 72 % yield) as solid. ESI MS (m / z) 358.2 (MH)+.

[0354] Step-4: Synthesis of 3-(Ethylthio)-4-(6-(trifluoromethyl)imidazo[l,2-a]pyridin-2-yl)-lH-pyrazol- 5-amine

[0355] To a stirred solution of 3,3-bis(ethylhio)-2-(6-(trifluoromethyl)imidazo[l,2-a]pyridin-2-yl)acrylonitrile (19.0 g, 53.2 mmol) in acetonitrile (200 mL) and ethanol (200 mL) at 0 °C, hydrazine hydrate (3.9 mL, 80.0 mmol) was added in a dropwise manner. The reaction mixture was stirred at 25 °C for 1 h and then at 75 °C for 16 h. After the completion of the reaction, the solvents were evaporated under reduced pressure. Water (200 mL) was added to the residue and extracted with ethyl acetate (3 X 200 mL). The combined organic layers were washed with saturated brine solution (100 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain 3-(ethylthio)-4-(6- (trifluoromethyl)imidazo[l,2-a]pyridin-2-yl)-lH-pyrazol-5-amine (13 g, 39.7 mmol, 74.7 % yield) as solid. ’H-NMR (400 MHz, DMSO-t / 6) 3 11.88 (s, 1H), 9.26 (s, 1H), 8.25 (s, 1H), 7.68 (d, J = 9.3 Hz, 1H), 7.42 (dd, J = 9.5, 1.7 Hz, 1H), 6.05 (s, 2H), 2.95 (d, J = 6.1 Hz, 2H), 1.27 (t, J = 7.2 Hz, 3H); ESI MS (m / z) 328.0 (MH)+.

[0356] Step-5: Synthesis of Ethyl 2-(ethylthio)-3-(6-(trifluoromethyl)iniidazo[l,2-a]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate

[0357] To a stirred solution of 3-(ethylthio)-4-(6-(trifluoromethyl)imidazo[l,2-a]pyridin-2-yl)-lH-pyrazol-5- amine (4.0 g, 12.22 mmol) in acetic acid (100 mL), ethyl (E)-4-ethoxy-2-oxobut-3-enoate (3.16 g, 18.33 mmol) was added and the resulting reaction mixture was stirred at 110 °C for 3 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C, evaporated the solvent under reduce pressure to obtain a residue. The residue was diluted with ethylacetate (100 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution (2 x 100 mL), brine solution (2 x 50 mL), dried over anhydrous sodium sulphate, filtered and evapoarted to obtain a crude product which was purified by flash column chromatography to obtain ethyl 2-(ethylthio)-3-(6-(trifluoromethyl)imidazo[l,2- a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate (2.0 g, 4.59 mmol, 37.6 % yield) as a powder. ESI MS (m / z) 436.3 (MH)+1.

[0358] Step-6: Synthesis of 2-(Ethylthio)-3-(6-(trifluoromethyl)imidazo[l,2-a]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carboxylic acid

[0359] To a stirred solution of ethyl 2-(ethylthio)-3-(6-(trifluoromethyl)imidazo[l,2-a]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate (1.6 g, 3.67 mmol) in tetrahydrofuran (80 mL). Lithium hydroxide monohydrate (0.46 g, 11.02 mmol) in water (13 mL) was added and the resulting reaction mixture was stirred at 25 °C for 1 h. After the completion of the reaction, the reaction mixture was diluted with water (20 mL) and neutralized to pH=4 using with LO N aqueous hydrochloride solution. The aqueous layer was extracted with ethyl acetate (2 x 25 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered, and evaporated under reduced pressure to obtain a crude product which was further washed with diethylether to obtain 2-(ethylthio)-3-(6- (trifluoromethyl)imidazo[l,2-a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylic acid (1.272 g, 3.12 mmol, 85 % yield) as a solid. ESI MS (m / z) 407.7 (MH)+.

[0360] Step-7: Synthesis of 2-(Ethylthio)- / V-methyl-3-(6-(trifluoroniethyl)iniidazo[l,2-a]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide

[0361] To a stirred solution of 2-(ethylthio)-3-(6-(trifluoromethyl)imidazo[l,2-a]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carboxylic acid (400 mg, 0.98 mmol) in / V, / V-dinicthylfornianiidc (6 mL), pyridine (0.63 mL, 7.86 mmol), 1 -propylphosphonic anhydride (0.88 mL, 1.47 mmol) and methanamine (1.23 mL, 2.45 mmol) were added at 0 °C. The resulting reaction mixture was stirred at 25 °C for 16 h. After the completion of the reaction, the reaction mixture was poured into ice water (20 mL). The solid obtained was filtered, washed with diethyl ether (5 mL) and dried to get the desired 2-(ethylthio)-A-methyl-3-(6- (trifluoromethyl)imidazo[l,2-a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (360 mg, 0.856 mmol, 87 % yield) as a solid. 'H-NMR (400 MHz, DMSO-cL) 5 9.78 (d, J = 4.8 Hz, 1H), 9.36 (s, 1 H), 8.82 (d, J = 4.4 Hz, 1H), 8.73 (s, 1H), 7.80 (d, J = 9.2 Hz, 1H), 7.57 (d, J = 4.4 Hz, 1H), 7.49-7.47 (m, 1H), 3.34-3.29 (m, 2H), 3.02 (d, J = 4.4 Hz, 3H), 1.46 (t, J = 7.2 Hz, 3H); ESI MS (m / z) 420.9 (MH)+.

[0362] Step-8: Synthesis of 2-(Ethylsulfonyl)-N-methyl-3-(6-(trifluoromethyl)imidazo[l,2-a]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide

[0363] To a stirred solution of 2-(ethylthio)-N-methyl-3-(6-(trifluoromethyl)imidazo[l,2-a]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (310 mg, 0.74 mmol) in dichloromethane (20 mL), 3- chloroperoxybenzoic acid (489 mg, 1.84 mmol) was added slowly at 0 °C. The resulting reaction mixture was stirred at 25 °C for 2 h. After the completion of the reaction, the reaction mixture was quenched with aqueous sodium thiosulphate solution (200 mL). The aqueous layer was extracted with dichloromethane (2x 50 mL). The combined organic layers were washed with aqueous saturated sodium bicarbonate solution (2 x 50 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain a crude product which was purified by flash column chromatography to obtain 2-(ethylsulfonyl)-N-methyl-3-(6-(trifluoromethyl)imidazo[l,2-a]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carboxamide (105 mg, 0.232 mmol, 31.5 % yield) as a yellow solid. 'H-NMR (400 MHz, DMSO-de) 5 9.42 (t, J = 4.8 Hz, 1H), 9.39 (s, 1H), 8.98 (d, J = 4.4 Hz, 1H), 8.69 (d, J = 0.5 Hz, 1H), 7.83 (d, J = 8.8 Hz, 1H), 7.77 (d, J = 4.4 Hz, 1H), 7.52 (dd, J = 9.4, 1.8 Hz, 1H), 4.11 (q, J = 7.4 Hz, 2H), 2.99 (d, J = 4.6 Hz, 3H), 1.25 (q, J = 7.4 Hz, 3H); ESI MS (m / z) 453.10 (MH)+.

[0364] Example-03: Synthesis of N-cyclopropyl-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide (Compound-247)

[0365] Step-1: Synthesis of 5-(ethylsulfonyl)-4-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin- 2-yl)- lH-pyrazol-3-amine

[0366] The desired 5-(ethylsulfonyl)-4-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-lH- pyrazol-3-amine (3.5 g, 9.35 mmol, 64.0 % yield) was prepared from of 5-(ethylthio)-4-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-lH-pyrazol-3-amine (5.0 g, 14.61 mmol), using the similar procedure mentioned in step-8 of Example- 1. ESI MS (m / z) 374.9 (MH)+

[0367] Step-2: Synthesis of ethyl 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxylate To a stirred solution of 5-(ethylsulfonyl)-4-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)-lH-pyrazol-3-amine (3.5 g, 9.35 mmol) in ethanol (35 mL), ethyl-2-formyl-3-oxopropionate (1.47 mL, 11.22 mmol) was added and the resulting mixture was stirred at 80 °C for 3 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C and ethanol was evaporated. The crude was diluted with ethyl acetate (50 mL), and the solid obtained was filtered, and dried under reduced pressure to obtain the desired ethyl 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxylate (4.1 g, 8.50 mmol, 91 % yield). 'H-NMR (400 MHz, DMSO-de) 5 10.05 (d, J = 2.2 Hz, 1H), 9.17 (d, J = 2.0 Hz, 1H), 8.86 (q, J = 0.9 Hz, 1H), 8.64 (d, J = 1.5 Hz, 1H), 4.43 (q, J = 7.1 Hz, 2H), 3.78 (q, J = 7.3 Hz, 5H), 1.38 (t, J = 7.1 Hz, 3H), 1.26 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 483.05 (MH)+.

[0368] Step-3: Synthesis of 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-

[0369] 2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxylic acid

[0370] To a stirred solution of ethyl 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxylate (3.6 g, 7.46 mmol) in 1,4-dioxane (45 mL), cone, hydrochloric acid (9.72 ml, 112 mmol) was added dropwise. The resulting mixture was stirred at 25 °C for 10 minutes then at 95 °C for 16 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C and the solvents were evaporated to get a residue. The residue was diluted with ice water (250 mL) to get a white precipitate, which was filtered, washed with water and dried to obtain 2- (ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-6-carboxylic acid (3.6 g, 7.92 mmol) as a mixture with it's corresponding decarboxylated product, which was not further purified and used in the next step as it is. ESI MS (m / z) 454.95 (MH)+.

[0371] Step-4: Synthesis of N-cyclopropyl-2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide

[0372] To a stirred solution of 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-6-carboxylic acid (200 mg, 0.44 mmol) in dichloromethane (4 mL) at 0 °C, cyclopropanamine (35 μL, 0.46 mmol) and pyridine (0.22 mL, 2.64 mmol) were added and for 10 minutes at 0 °C followed by the addition of 1-propanephosphonic acid cyclic anhydride (0.38 mL, 0.66 mmol). The resulting reaction mixture was warmed to 25 °C and stirred for 16 h. After the completion of the reaction, the reaction mixture was diluted with water (25 mL) and was extracted with dichloromethane (4 x 20 mL). The combined organic layers were washed with saturated brine solution (25 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to get a crude product which was purified by flash chromatography to obtain A-cyclopropyl-2-(ethylsulfonyl)-

[0373] 3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6- carboxamide (110 mg, 0.223 mmol, 50.6 % yield). 'H-NMR (400 MHz, DMSO-A) 5 9.79 (d, J = 2.0 Hz, 1H), 9.15 (d, J = 2.2 Hz, 1H), 8.89 (d, J = 3.9 Hz, 1H), 8.85 (d, J = 1.2 Hz, 1H), 8.63 (d, J = 1.5 Hz, 1H), 3.79-3.74 (m, 5H), 2.93-2.88 (m, 1H), 1.25 (t, J = 7.3 Hz, 3H), 0.80-0.75 (m, 2H), 0.64-0.60 (m, 2H); ESI MS (m / z) 494.25 (MH)+.

[0374] Example-4: Synthesis of N-ethoxy-2-(ethylsulfonyl)-7-methyl-3-(3-methyl-6-(trifluoromethyl)- 3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide (Compound-235)

[0375] Step-1: Synthesis of ethyl 2-(ethylthio)-7-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxylate

[0376] To a stirred solution of ethyl (Z)-2-((dimethylamino)methylene)-3-oxobutanoate (9.74 g, 52.6 mmol) in ethanol (100 mL), 3-(ethylthio)-4-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)- lH-pyrazol-5-amine (9 g, 26.3 mmol) was added and the resulting mixture was stirred at 85 °C for 16 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C, the solvents were evaporated under reduced pressure to obtain a residue. The residue was triturated with water (300 mL) and the resulting solid was filtered, washed with hexane (30 mL) to obtain desired ethyl 2-(ethylthio)- 7-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine- 6-carboxylate (11.0 g, 23.68 mmol, 90 % yield). ). ’H-NMR (400 MHz, CHLORFORM-d ) δ 9.03 (s, 1H), 8.68 (d, J = 1.2 Hz, 1H), 8.38 (d, J = 1.2 Hz, 1H), 4.45 (q, J = 7.2 Hz, 2H), 4.03 (s, 3H), 3.35 (q, J = 3.6 Hz, 2H), 3.22 (s, 3 H), 1.51 (t, J = 7.6 Hz, 3H), 1.44 (t, J = 7.2 Hz, 3H); ESI MS (m / z) 465.20 (MH)+.

[0377] Step-2: Synthesis of ethyl 2-(ethylsulfonyl)-7-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxylate

[0378] The desired ethyl 2-(ethylsulfonyl)-7-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxylate (6.5 g, 13.09 mmol, 60.8 % yield) was prepared from ethyl 2-(ethylthio)-7-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxylate (10 g, 21.53 mmol), using the similar procedure mentioned in step-8 of Example-1. 'H-NMR (400 MHz, DMSO-d6) 5 9.11 (s, 1H), 8.85 (q, J = 0.9 Hz, 1H), 8.63 (q, J = 0.9 Hz, 1H), 4.42 (q, J = 7.1 Hz, 2H), 3.81-3.75 (m, 5H), 3.19 (s, 3H), 1.38 (t, J = 7.0 Hz, 3H), 1.27 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 497.20 (MH)+.

[0379] Step-3: Synthesis of 2-(ethylsulfonyl)-7-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxylic acid

[0380] To a stirred solution of ethyl ethyl 2-(ethylsulfonyl)-7-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxylate (3 g, 6.04 mmol) in tetrahydrofuran (30 mL), lithium hydroxide monohydrate (0.56 g, 13.29 mmol) in water (3 mL) was added slowly at 25 °C and stirred for 3 h. After the completion of the reaction, the reaction mixture was diluted with water (5 mL) and acidified (pH=4) using 10% hydrochloric acid solution. The aqueous layer was extracted with ethyl acetate (3 x 20 mL), dried over anhydrous sodium sulphate, filtered, and evaporated under reduced pressure to obtain 2-(ethylsulfonyl)-7-methyl-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l ,5-a]pyrimidine-6-carboxylic acid (2.41 g, 5.15 mmol, 85 % yield) which was used in the next step without any further purification. 'H-NMR (400 MHz, DMSO-de) 5 8.85 (t, J = 1.1 Hz, 1H), 8.62 (d, J = 1.8 Hz, 2H), 3.72 (s, 3H), 3.57 (q, J = 7.3 Hz, 2H), 2.61 (s, 3H), 1.22 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 468.95 (MH)+.

[0381] Step-4: Synthesis of N-ethoxy-2-(ethylsulfonyl)-7-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxamide

[0382] To a stirred solution of 2-(ethylsulfonyl)-7-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-6-carboxylic acid (200 mg, 0.43 mmol) in N,N- dimethylformamide (2 mL), HATU (406 mg, 1.07 mmol), DIPEA (0.37 ml, 2.14 mmol) and O- ethylhydroxylamine hydrochloride (62.5 mg, 0.64 mmol) were added at 25 °C and stirred at 60 °C for 16 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C and diluted with water (50 mL). The aqueous layer was extracted with ethyl acetate (4 x 25 mL), the combined organic layers were washed with saturated brine solution (100 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product which was purified by flash column chromatography to obtain N-ethoxy-2-(ethylsulfonyl)-7-methyl-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l ,5-a]pyrimidine-6-carboxamide (81 mg, 0.158 mmol, 37.1 % yield. 'H-NMR (400 MHz, DMSO-J6) 5 8.81 (d, J = 1.2 Hz, 1H), 8.57 (d, J = 1.5 Hz, 1H), 8.06 (s, 1H), 4.11 (q, J = 7.0 Hz, 2H), 3.74 (s, 3H), 3.65-3.57 (m, 2H), 2.18 (s, 3H), 1.25-1.18 (m, 6H); ESI MS (m / z) 512.00 (MH)+.

[0383] Example-5: Synthesis of N-ethyl-2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (Compound-297)

[0384] Step-1: Synthesis of 2-cyano-N-(5-(methylamino)-2-(trifluoromethyl)pyridin-4-yl)acetamide

[0385] To a stirred solution of N3-methyl-6-(trifluoromethyl)pyridine-3,4-diamine (40 g, 209 mmol) in dichloromethane (400 mL) at 0 °C, under nitrogen, 2-cyanoacetic acid (44.5 g, 523 mmol) and l-(3- dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (64.2 g, 335 mmol) were added followed by the addition of / V, / V-diisopropylcthylaminc (110 mL, 628 mmol). The resulting reaction mixture was stirred at 25 °C for 24 h under nitrogen. After the completion of the reaction, the reaction mixture was concentrated to obtain a residue which was diluted with water (1000 mL). The aqueous layer was extracted with dichloromethane (3 x 300 mL), the combined organic layers were washed with brine solution (800 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain the crude 2-cyano-N-(5-(methylamino)-2-(trifluoromethyl)pyridin-4-yl)acetamide (40 g, 155 mmol, 74.0 % yield), which further used in next step without purification. ESI MS (m / z) 259.05 (MH)+.

[0386] Step-2: Synthesis of 2-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)acetonitrile

[0387] A stirred solution of 2-cyano-A-(5-(methylamino)-2-(trifluoromethyl)pyridin-4-yl)acetamide (40 g, 155 mmol) in acetic acid (400 mL) was stirred at 110 °C for 3 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C, and the solvent was evaporated under reduced pressure. The residue was diluted with water (800 mL) and the aqueous layer was extracted with ethyl acetate (3 x 300 mL). The combined organic layers were washed with aqueous sodium bicarbonate solution (800 mL), saturated brine solution (800 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain the crude compound which was purified by flash column chromatography to obtain the desired 2-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)acetonitrile (30 g, 125 mmol, 81 % yield). 'H-NMR (400 MHz, DMSO-tfc) 5 9.10 (s, 1H), 8.17 (s, 1H), 4.68 (s, 2H), 3.91 (s, 3H); ESI MS (m / z) 240.90 (MH)+

[0388] Step-3: Synthesis of 3,3-bis(ethylthio)-2-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin- 2-yl)acrylonitrile

[0389] To a stirred solution of KOH (22.53 g, 341 mmol) in acetonitrile (550 mL) at 0 °C, 2-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)acetonitrile (41 g, 171 mmol) was added. The resulting reaction mixture was stirred for 1 h at 25 °C and it was cooled to -5 °C followed by dropwise addition of carbon disulfide (11.35 mL, 188 mmol). The reaction mixture was stirred for 1 h at -5 °C, followed by the addition of ethyl iodide (27.4 mL, 341 mmol) at 0 °C. The reaction mixture was stirred for 2 h at 0 °C and then at 25 °C for 16 h. After the completion of the reaction, the volatiles were evaporated under reduced pressure. The residue was diluted with water (800 mL) and the aqueous layer was extracted with ethyl acetate (3 x 200 mL). The combined organic layers were washed with saturated brine solution (800 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain the crude compound which was purified by flash column chromatography to obtain the desired 3,3-bis(ethylthio)-2-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)acrylonitrile (51 g, 137 mmol, 80 % yield). 'H-NMR (400 MHz, DMSO-cL) 9.20 (s, 1H), 8.24 (s, 1H), 3.97 (s, 3H), 3.24 (q, J = 7.3 Hz, 2H), 2.80 (q, J = 7.4 Hz, 2H), 1.36 (t, J = 7.5 Hz, 3H), 1.13 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 372.90 (MH)+.

[0390] Step-4: Synthesis of 3-(ethylthio)-4-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)-lH-pyrazol-5-amine To a stirred solution of 3,3-bis(ethylthio)-2-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)acrylonitrile (25 g, 67.1 mmol) in ethanol (250 mL) and acetonitrile (125 mL) at 0 °C, hydrazine hydrate (3.95 mL, 81 mmol) was added and the resulting reaction mixture was stirred for 1-1.5 h. After the completion of the reaction, the reaction mixture was poured into ice-cold water (1.5 L). The resulting yellow solid was filtered and dried. The yellow crude compound was purified by flash column chromatography to obtain the desired 3-(ethylthio)-4-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- c]pyridin-2-yl)-lH-pyrazol-5-amine (13 g, 38.0 mmol, 56.6 % yield). 'H-NMR (400 MHz, DMSO-A) 5 12.01 (s, 1H), 9.03 (s, 1H), 8.07 (s, 1H), 5.73 (s, 2H), 3.84 (s, 3H), 2.87 (q, J = 7.3 Hz, 2H), 1.16 (t, J = 7.1 Hz, 3H); ESI MS (m / z) 343.15 (MH)+

[0391] Step-5: Synthesis of ethyl 2-(ethylthio)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate

[0392] To a stirred solution of 3-(ethylthio)-4-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)- lH-pyrazol-5-amine (9 g, 26.3 mmol) in ethanol (90 mL), ethyl (Z)-4-ethoxy-3-methyl-2-oxobut-3- enoate (7.34 g, 39.4 mmol) was added at 25 °C. The resulting reaction mixture was stirred at 85 °C for 4-5 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C, poured into water (100 mL) and extracted with ethyl acetate (4 x 50 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and evaporated to obtain the crude compound which was purified by flash column chromatography to obtain ethyl 2-(ethylthio)-6-methyl-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate (8.2 g, 17.65 mmol, 67.2 % yield); ’H-NMR (400 MHz, DMSO-J6) 5 9.14 (s, 1H), 8.75 (s, 1H), 8.19 (s, 1H), 4.58 (q, J = 6.8 Hz, 2H), 4.01 (s, 3H), 3.15 (q, J = 7.2 Hz, 2H), 2.37 (s, 3H), 1.40 (t, J = 6.8 Hz, 3H), 1.35 (t, J = 7.2 Hz, 3H); ESI MS (m / z) 465.5 (MH)+

[0393] Step-6: Synthesis of ethyl 2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate

[0394] The desired ethyl 2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate (8.75 g, 17.62 mmol, 82 % yield) was prepared from ethyl 2-(ethylthio)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate (10 g, 21.53 mmol), using the similar procedure mentioned in step-8 of Example-1. 'H-NMR (400 MHz, DMSO-t e) 5 9.22 (s, 1H), 8.91 (s, 1H), 8.26 (d, J = 1.0 Hz, 1H), 4.62 (q, J = 7.1 Hz, 2H), 3.90 (s, 3H), 3.70 (q, J = 7.4 Hz, 2H), 2.45 (s, 3H), 1.41 (t, J = 7.1 Hz, 3H), 1.23 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 497.15 (MH)+

[0395] Step-7: Synthesis of 2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-iniidazo[4,5- c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylic acid

[0396] The desired 2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylic acid (1.6 g, 3.42 mmol, 56.5 % yield) was prepared from ethyl 2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate (3 g, 6.04 mmol), using the similar procedure mentioned in step-6 of Example-1. 'H-NMR (400 MHz, DMSO-t e) 5 9.22 (s, 1H), 8.89 (s, 1H), 8.26 (d, J = 0.6 Hz, 1H), 3.89 (s, 3H), 3.71 (q, J = 7.4 Hz, 2H), 2.44 (s, 3H), 1.23 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 468.85 (MH)+

[0397] Step-8: Synthesis of N-ethyl-2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide

[0398] To a stirred solution of 2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylic acid (300 mg, 0.64 mmol) in N,N- dimethylformamide (3 mL), pyridine (0.26 ml, 3.20 mmol), PyBOP (500 mg, 0.96 mmol) were added at 25 °C followed by the addition of ethanamine hydrochloride (54.8 mg, 0.67 mmol). The resulting reaction mixture was stirred at 25 °C for 16 h. After the completion of the reaction, the reaction mixture was diluted with water (25 mL) and extracted with ethyl acetate (4 x 20 mL). The combined organic layers were washed with saturated brine solution (25 mL), dried over anhydrous sodium sulphate, filtered and concentrated to obtain the crude compound which was purified using flash column chromatography to obtain the desired product A-ethyl-2-(ethylsulfonyl)-6-methyl-3-(3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (65 mg, 0.131 mmol, 20.48 % yield). ’H-NMR (400 MHz, DMSO-J6) 5 9.23 (s, 1H), 9.10 (t, J = 5.4 Hz, 1H), 8.88 (s, 1H), 8.26 (s, 1H), 3.89 (s, 3H), 3.68 (q, J = 7.4 Hz, 2H), 3.46-3.40 (m, 2H), 2.38 (s, 3H), 1.22 (dt, J = 17.0, 7.3 Hz, 6H); ESI MS (m / z) 496.20 (MH)+.

[0399] Example-6: Synthesis of 2-(ethylsulfonyl)-N,N-dimethyl-3-(6-(2,2,3,3,3- pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (Compound-26)

[0400] Step-1: Synthesis of 3-methyl-6-(2,2,3,3,3-pentafluoropropoxy)pyridazine

[0401] To a stirred solution of 3-chloro-6-methylpyridazine (15 g, 117 mmol) in A,A-dimethylformamide (200 mL), 2,2,3,3,3-pentafluoropropan-l-ol (26.3 g, 175 mmol) and NaH (55% by wt; 7.00 g, 175 mmol) were added at 0 °C. The resulting reaction mixture was stirred at 80 °C for 14 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C and quenched with water (300 mL). The aqueous layer was extracted with ethyl acetate (3 x 500 mL), the combined organic layers were washed with saturated brine solution (500 mL), dried over anhydrous sulphate, filtered and concentrated under reduced pressure to obtain the crude compound which was purified by flash column chromatography to obtain 3-methyl-6-(2,2,3,3,3-pentafluoropropoxy)pyridazine (19 g, 78.0 mmol, 67.2 % yield).1H-NMR (400 MHz, CHLOROFORM-<7) 5 7.31 (d, J = 9.2 Hz, 1H), 7.01 (d, J = 9.2 Hz, 1H), 5.02-4.95 (m, 2H), 2.64 (s, 3H); ESI MS (m / z) 242.95 (MH)+.

[0402] Step-2: Synthesis of 3-(chloromethyl)-6-(2,2,3,3,3-pentafluoropropoxy)pyridazine

[0403] To a strried solution of 3-methyl-6-(2,2,3,3,3-pentafluoropropoxy)pyridazine (5 g, 20.65 mmol) in chloroform (50 mL) at 65 °C, l,3,5-trichloro-[l,3,5]triazinane-2,4,6-trione (3.36 g, 14.45 mmol) was added. The reaction mixture was stirred at 65 °C for 1 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C and diluted with dichloromethane (250 mL). The organic layer was washed with an aqueous solution of IN NaOH (250 mL), saturated brine solution (200 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain the crude compound which was purified by flash column chromatography to obtain 3-(chloromethyl)-6- (2,2,3,3,3-pentafluoropropoxy)pyridazine (40 g, 145 mmol, 62.5 % yield). 'H-NMR (400 MHz, CHLOROFORM-<7) 5 7.68 (d, J = 9.2 Hz, 1H), 7.16 (d, J = 9.2 Hz, 1H), 5.06-4.99 (m, 2H), 4.82 (s, 2H); GC MS (m / z) 275.9.

[0404] Step-3: 2-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)acetonitrile

[0405] To a stirred solution of 3-(chloromethyl)-6-(2,2,3,3,3-pentafluoropropoxy)pyridazine (35 g, 127 mmol) in acetonitrile (700 mL), trimethylsilyl cyanide (25.4 mL, 190 mmol) and TBAF (190 mL, 190 mmol) were added at 0 °C. The reaction mixture was stirred at 25 °C for 14 h. After the completion of the reaction, the reaction mixture was poured into water (1000 mL) and extracted with ethyl acetate (2 x 2000 mL). The combined organic layers were washed with saturated brine solution (1500 mL), dried over anhydrous sodium sulphate, filtered and concentrated to obtain a crude product which was purified by flash column chromatography to obtain 2-(6-(2, 2,3,3, 3-pentafluoropropoxy)pyridazin-3- yl)acetonitrile (20.5 g, 77 mmol, 60.6 % yield). 'H-NMR (400 MHz, DMSO-A) 5 7.73 (d, J = 9.2 Hz, 1H), 7.45 (d, J = 9.2 Hz, 1H), 5.32-5.25 (m, 2H), 4.36 (s, 2H); ESI MS (m / z) 267.5 (MH)+.

[0406] Step-4: Synthesis of 3,3-bis(ethylthio)-2-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3- yl)acrylonitrile

[0407] The desired 3,3-bis(ethylthio)-2-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)acrylonitrile (21 g, 52.6 mmol, 70.2 % yield) was prepared from 2-(6-(2, 2,3,3, 3-pentafluoropropoxy)pyridazin-3- yl)acetonitrile (20 g, 74.9 mmol), using the similar procedure mentioned in step-3 of Example-1. 'H- NMR (400 MHz, CHLOROFORM-tf) 5 7.80 (d, J = 9.6 Hz, 1H), 7.17 (d, J = 9.6 Hz, 1H), 5.11-5.04 (m, 2H), 3.13 (q, J = 7.6 Hz, 2H), 3.02 (q, J = 7.2 Hz, 2H), 2.80 (q, J = 7.4 Hz, 2H), 1.42 (t, J = 7.6 Hz, 3H), 1.28 (t, J = 7.6 Hz, 3H); ESI MS (m / z) 399.65 (MH)+.

[0408] Step-5: 3-(ethylthio)-4-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-lH-pyrazol-5-amine The desired 3-(ethylthio)-4-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-lH-pyrazol-5-amine (16 g, 43.3 mmol, 87 % yield) was prepared from 3,3-bis(ethylthio)-2-(6-(2,2,3,3,3- pentafluoropropoxy)pyridazin-3-yl)acrylonitrile (20 g, 50.1 mmol), using the similar procedure mentioned in step-4 of Example-1. ESI MS (m / z) 369.55 (MH)+.

[0409] Step-6: ethyl 2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5- a]pyrimidine-7-carboxylate

[0410] The desired ethyl 2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5- a]pyrimidine-7-carboxylate (3.4 g, 7.12 mmol, 49.0 % yield) was prepared from 3-(ethylthio)-4-(6- (2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-lH-pyrazol-5-amine (4.29 g, 11.62 mmol), using the similar procedure mentioned in step-5 of Example- l.'H-NMR (400 MHz, CHLOROFRM-t / ) 5 8.21 (d, J = 9.2 Hz, 12H), 8.58 (d, J = 4.4 Hz, 1H), 7.26 (d, J = 4.4 Hz, 1H), 7.18 (d, J = 9.2 Hz, 1H), 5.12-5.06 (m, 2H), 4.58 (q, J = 6.8 Hz, 2H), 3.33 (q, J = 7.6 Hz, 2H), 1.53-1.47 (m, 6H); ESI MS (m / z) 478.3 (MH)+.

[0411] Step-7: 2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5- a]pyrimidine-7-carboxylic acid

[0412] To a stirred solution of ethyl 2-(ethylthio)-3-(6-(2, 2,3,3, 3-pentafluoropropoxy)pyridazin-3- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate (3.5 g, 7.33 mmol) in ethanol (50 mL), lithium hydroxide (1.76 g, 73.3 mmol) in water (50.0 ml) was added and stirred at 25 °C for 1.5 h. After the completion of the reaction, the solvents were evaporated and the residue obtained was acidified using 6 N aqueous HC1 solution and extracted with ethylacetate (2 x 50 mL). The combined organic layers were washed with brine solution (2 x 50 mL), dried over anhydrous sodium sulphate, filtered and evapoarated under reduced pressure to obtain 2-(ethylthio)-3-(6-(2, 2,3,3, 3-pentafluoropropoxy)pyridazin-3- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylic acid (2.8 g, 6.23 mmol, 85 % yield). 'H-NMR (400 MHz, CHLOROFORM-t ) 8.83 (d, J = 9.2 Hz, 1H), 8.80 (d, J = 4.4 Hz, 1H), 7.76 (d, J = 4.4 Hz, 1H), 7.24 (d, J = 9.2 Hz, 1H), 5.14-5.07 (m, 2 H), 3.23 (q, J = 7.6 Hz, 2H), 1.54 (t, J = 7.6 Hz, 3H); ESI MS (m / z) 450.5 (MH)+.

[0413] Step-8: 2-(ethylthio)-N,N-dimethyl-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide

[0414] To a stirred solution of 2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5- a]pyrimidine-7-carboxylic acid (500 mg, 1.113 mmol) in N, A-dimethylformamide (5 mL), pyridine (0.9 mL, 11.13 mmol), 1-propylphosphonic anhydride (1.0 mL, 1.669 mmol) and dimethylamine hydrochloride (100 mg, 1.224 mmol) were added at 0 °C. The reaction mixture was stirred for 16 h at 25 °C. After the completion of the reaction, the reaction mixture was poured into ice water. The resulting solid was filtered and washed with water, diethyl ether and dried to obtain the desired 2-(ethylthio)- A,A-dimethyl-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide (250 mg, 0.524 mmol, 47.2 % yield). 'H-NMR (400 MHz, CHLOROFORM-t / ) 8.82 (d, J = 9.2 Hz, 1H), 8.57 (d, J = 4.4 Hz, 1H), 7.18 (d, J = 9.2 Hz, 1H), 6.88 (d, J = 4.4 Hz, 1H), 5.09 (t, J = 12.8 Hz, 2H), 3.28-3.22 (m, 5 H), 2.92 (s, 1H), 1.46 (t, J = 7.6 Hz, 3H); ESI MS (m / z) 477.5 (MH)+.

[0415] Step-9: 2-(ethylsulfonyl)-N,N-dimethyl-3-(6-(2, 2,3,3, 3-pentafluoropropoxy)pyridazin-3- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide

[0416] To a stirred solution of 2-(cthylthio)- / V, / V-dimcthyl-3-(6-(2, 2,3,3, 3-pentafluoropropoxy)pyridazin-3- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (200 mg, 0.420 mmol) in dichloromethane (10 mL), mCPBA (217 mg, 0.88 mmol) was added at 25 °C. The reaction mixture was stirred for 4 h at 25 °C. After the completion of the reaction, the reaction mixture was diluted with dichloromethane (15 mL), washed with aqueous saturated sodium thiosulfate solution (25 mL), aqueous IN NaOH (10 mL), dried over anhydrous sodium sulphate, filtered and concentrated to obtain the crude compound which was purified by using flash column chromatography to obtain 2-(ethylsulfonyl)-A,A-dimethyl-3-(6- (2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (105 mg, 0.207 mmol, 49.2 % yield). ’H-NMR (400 MHz, DMSO- d ) 58.91 (d, J = 4.4 Hz, 1H), 8.22 (d, J = 9.3 Hz, 1H), 7.60 (d, J = 9.0 Hz, 1H), 7.55 (d, J = 4.2 Hz, 1H), 5.36 (t, J = 13.3 Hz, 2H), 3.80 (q, J = 7.3 Hz, 2H), 3.13 (s, 3H), 2.90 (s, 3H), 1.24 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 509.00 (MH)+.

[0417] Example-7: Synthesis of N-cyclopropyl-2-(ethylsulfonyl)-3-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5- a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (Compound-228)

[0418] Step-1 : l,2-diamino-5-(trifluoromethyl)pyridin-l-ium diphenylphosphinate

[0419] To a stirred solution of 5-(trifluoromethyl)pyridin-2-amine (30 g, 185 mmol) in dichloromethane (500 mL), (aminooxy)diphenylphosphine oxide (43.2 g, 185 mmol) was added at 25 °C. The resulting reaction mixture was stirred at 25 °C for 18 h. After the completion of the reaction, the reaction mixture was diluted with hexane (250 mL) and the resulting white precipitate was filtered, washed with diethyl ether (200 mL), and dried to obtain l,2-diamino-5-(trifluoromethyl)pyridin-l-ium diphenylphosphinate (44 g, 111 mmol, 60.1 % yield) as off white solid.; ESI MS (m / z) 178.10 (MH)+.

[0420] Step-2: 2-(ethylthio)-3-(6-(trifhioromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5- a]pyrimidin-7(4H)-one

[0421] To a stirred solution of 2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-3-carboxylic acid (20 g, 84 mmol) and l,2-diamino-5-(trifluoromethyl)pyridin-l-ium diphenylphosphinate (33.0 g, 84 mmol) in pyridine (300 mL), l-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (24.04 g, 125 mmol) and lH-l,2,3-benzotriazol-l-ol hydrate (14.31 g, 84 mmol) were added. The resulting reaction mixture was stirred at 85 °C for 16 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C and solvents were evaporated. The residue was diluted with water (I L) and extracted with ethyl acetate (3 x 500 mL). The combined organic layers were washed with IN HC1 solution (500 mL), dried over anhydrous sodium sulphate, filtered and concentrated to obtain a crude product which was purified by flash column chromatography to obtain 2-(ethylthio)-3-(6- (trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidin-7(4H)-one (10 g, 26.3 mmol, 31.5 % yield). 'H-NMR (400 MHz, DMSO-t6) 3 11.93 (brs, 1H), 9.60 (d, J = 1.2 Hz, 1H), 7.98 (d, J = 1.2 Hz, 2H), 7.85 (d, J = 6.0 Hz, 1H), 5.89 (d, J = 3.2 Hz, 1H), 3.24 (q, J = 7.6 Hz, 2H), 1.39 (t, J = 7.6Hz, 3H); ESI MS (m / z) 380.9 (MH)+.

[0422] Step-3: Synthesis of 2-(7-chloro-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)-

[0423] [1.2.4] triazolo[ 1 ,5-a] pyridine

[0424] To a stirred solution of 2-(ethylthio)-3-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2- yl)pyrazolo[l,5-a]pyrimidin-7(4H)-one (20 g, 84 mmol) in toluene (100 mL) and acetonitrile (100 mL), POCk (24.5 mL, 263 mmol) was added at 25 °C. The reaction mixture was stirred at 100 °C for 12 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C and poured into ice-water (I L) and extracted with ethyl acetate (2 x 500 mL). The combined organic layers were washed with saturated sodium bicarbonate solution (2 x 500 mL), dried over anhydrous sodium sulphate, filtered and concentrated to obtain a crude compound which was purified by flash column chromatography to obtain 2-(7-chloro-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)-[l,2,4]triazolo[l,5- a]pyridine (7 g, 17.55 mmol, 66.8 % yield). 'H-NMR (400 MHz, DMSO-t e) 5 9.74 (d, J = 1.2 Hz, 1H), 8.64 (d, J = 4.4 Hz, 1H), 8.06 (d, J = 9.6 Hz, 1H), 7.94 (dd, J = 9.6 Hz, 2.0 Hz, 1H), 7.50 (d, J = 4.4 HZ, 1H), 3.17 (q, J = 9.6 Hz, 2H), 1.43 (t, J = 7.2 Hz, 3H); ESI MS (m / z) 398.85 (MH)+

[0425] Step-4: Synthesis of 2-(7-chloro-2-(ethylsulfonyl)pyrazolo[l,5-a]pyrimidin-3-yl)-6-

[0426] (trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridine

[0427] The desired 2-(7-chloro-2-(ethylsulfonyl)pyrazolo[l ,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)-

[0428] [1.2.4]triazolo[l,5-a]pyridine (12.5 g, 29.0 mmol, 96 % yield) was prepared from 2-(7-chloro-2- (ethylthio)pyrazolo[l ,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)-[l ,2,4]triazolo[l ,5-a]pyridine (12 g, 30.1 mmol), using the similar procedure mentioned in step-8 of Example- 1. 'H-NMR (400 MHz, CHLOROFRM-tf) 5 9.09 (s, 1H), 8.78 (d, J = 4.8 Hz, 1H), 7.98 (d, J = 9.6 Hz, 1H), 7.73 (dd, J = 9.6 Hz, 2.0 Hz, 1H), 7.33 (d, J = 4.4 HZ, 1H), 3.97 (q, J = 9.6 Hz, 2H), 1.52 (t, J = 7.2 Hz, 3H); ESI MS (m / z) 431.1 (MH)+

[0429] Step-5: Synthesis of 3-(ethylsulfonyl)-4-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2-yl)- lH-pyrazol-5-amine To a stirred solution of 2-(7-chloro-2-(ethylsulfonyl)pyrazolo[l,5-a]pyrimidin-3-yl)-6- (trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridine (12 g, 27.9 mmol) in / V, / V-dimcthylfomiamidc (180 mL), / VI , / V2-dimcthylcthanc- l ,2-diaminc (30.0 mL, 279 mmol) was added at 25 °C. The resulting reaction mixture was stirred at 25 °C for 12 h. After the completion of the reaction, the reaction mixture was poured into ice-cold water (250 mL). The precipitated solid product was filtered, washed with water (1 L) followed by hexane (200 mL) and dried to obtain 3-(ethylsulfonyl)-4-(6-(trifluoromethyl)- [l,2,4]triazolo[l,5-a]pyridin-2-yl)-lH-pyrazol-5-amine (10 g, 27.8 mmol, 100 % yield). 'H-NMR (400 MHz, DMSO-de) 5 12.85 (brs, 1H), 9.61 (s, 1H), 7.99-7.92 (m, 2H), 6.44 (s, 2H), 3.82 (q, J = 7.2 Hz, 2H), 1.19 (t, J = 7.6 Hz, 3H).; ESI MS (m / z) 361.05 (MH)+

[0430] Step-6: ethyl 2-(ethylsulfonyl)-3-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate

[0431] The desired ethyl 2-(ethylsulfonyl)-3-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate (6.6 g, 14.09 mmol, 52.9 % yield) was prepared from 3- (ethylsulfonyl)-4-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2-yl)-lH-pyrazol-5-amine (9.6 g,

[0432] 26.6 mmol), using the similar procedure mentioned in step-5 of Example- l.'H-NMR (400 MHz, DMSO-de) 5 9.82 (s, 1H), 8.98 (d, J = 4.4 Hz, 1H), 8. 14 (d, J = 9.2 Hz, 1H), 8.04-8.01 (m, 1H), 7.86 (d, J = 4.4 Hz, 1H), 4.52 (q, J = 7.2 Hz, 2H), 3.89 (q, J = 7.2 Hz, 2H), 1.85 (t, J = 6.8 Hz, 3H), 1.28 (t, J =

[0433] 7.6 Hz, 3H).; ESI MS (m / z) 469.05 (MH)+

[0434] Step-7: 2-(ethylsulfonyl)-3-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5- a]pyrimidine-7-carboxylic acid

[0435] To a stirred solution of ethyl 2-(ethylsulfonyl)-3-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate (800 mg, 1.71 mmol) in tetrahydrofuran (10 mL), lithium hydroxide, monohydrate (143 mg, 3.42 mmol) in water (10.0 mL) was added at 0 °C. The resulting reaction mixture was stirred at 0 °C for 15 minutes. After the completion of the reaction, the reaction mixture was acidified with 2N aqueous HC1 solution (pH 2-3) and the volatiles were evaporated. The solid obtained was filtered, washed with 50% ethyl acetate in hexane (50 ml) and dried to obtain 2- (ethylsulfonyl)-3-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxylic acid (700 mg, 1.590 mmol, 93 % yield). ESI MS (m / z) 440.85 (MH)+

[0436] Step-8: / V-cyclopropyl-2-(ethylsulfonyl)-3-(6-(trifluoromethyl)-[ l,2,4]triazolo[ l,5-a]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide

[0437] To a stirred solution of 2-(ethylsulfonyl)-3-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylic acid (150 mg, 0.341 mmol) in A,A-dimethylformamide (2 mL), pyridine (0.14 mL, 1.70 mmol), cyclopropanamine (38.9 mg, 0.681 mmol) and 1- propylphosphonic anhydride (0.31 mL, 0.511 mmol) were added at 25 °C. The resulting reaction mixture was stirred at 25 °C for 16 h. After the completion of the reaction, the reaction mixture was quenched with water (25 mL) and the precipitated solid product was filtered, washed with water (100 mL) followed by 20% ethyl acetate in hexane (100 mL) and dried to obtain / V-cyclopropyl-2- (ethylsulfonyl)-3-(6-(trifluoromethyl)-[l,2,4]triazolo[l,5-a]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7- carboxamide (100 mg, 0.209 mmol, 61.2 % yield). 'H-NMR (400 MHz, DMSO-t e) 5 9.82 (d, J = 0.9 Hz, 1H), 9.45 (d, J = 4.3 Hz, 1H), 8.98 (d, J = 4.3 Hz, 1H), 8.15-8.11 (m, 1H), 8.03 (dd, J = 9.5, 1.8 Hz, 1H), 7.74 (d, J = 4.0 Hz, 1H), 3.97-3.88 (m, 2H), 3.03-2.98 (m, 1H), 1.29 (t, J = 7.3 Hz, 3H), 0.86 (td, J = 7.0, 5.1 Hz, 2H), 0.65-0.61 (m, 2H); ESI MS (m / z) 480.05 (MH)+

[0438] Example-8: Synthesis of 2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-3-carboxylic acid

[0439] Step-1: Synthesis of ethyl 2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-3- carboxylate

[0440] A mixture of ethyl 5-amino-3-(ethylthio)-lH-pyrazole-4-carboxylate (25 g, 116 mmol) and methyl 3,3- dimethoxypropanoate (19.76 mL, 139 mmol) in acetic acid (250 mL) was stirred at 110 °C for 18 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C and acetic acid was removed under reduced pressure. The residue was diluted with cold water (IL) to obtain a light yellow precipitate which was filtered and washed with water (1 L), hexane (500 mL) and dried to obtain ethyl 2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-3-carboxylate (30 g, 112 mmol, 97 % yield). ESI MS (m / z) 268.0 (MH)+

[0441] Step-2: Synthesis of 2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-3-carboxylic acid

[0442] To a stirred solution of ethyl 2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-3-carboxylate (20 g, 74.8 mmol) in ethanol (250 mL), sodium hydroxide (29.9 g, 748 mmol) in water (250 mL) was added at 25 °C. The resulting reaction mixture was stirred at 70 °C for 16 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C. The solvents were evaporated to get a residue which was acidified with cone HC1 ( pH= l).,The resulting white precipitate was filtered and dried to obtain 2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-3-carboxylic acid (15.5 g, 64.8 mmol, 87 % yield). ESI MS (m / z) 239.85 (MH)+.

[0443] Example-9: Synthesis of 2-(ethylsulfonimidoyl)-N-methoxy-N-methyl-3-(3-methyl-6-

[0444] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (Compound-293)

[0445] Step-1: Synthesis of 2-(ethylthio)-N-methoxy-N-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide

[0446] To a stirred solution of 2-(ethylthio)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylic acid (1.2 g, 2.84 mmol) in / V, / V-dimcthylfbrmairiidc (10 mL), pyridine (1.84 mL, 22.73 mmol), HATU (2.160 g, 5.68 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.291 g, 2.98 mmol) were added at 25 °C. The resulting reaction mixture was stirred for 16 h at 25 °C. After the completion of the reaction, the reaction mixture was poured into water (100 mL) and extracted with ethyl acetate (2 x 50 mL). The combined organic layers were washed with saturated brine solution (50 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain a crude product which was purified by flash column chromatography to obtain the desired 2-(ethylthio)-A-methoxy-A-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (600 mg, 1.289 mmol, 45.4 % yield). 1H-NMR (400 MHz, DMSO-d6)d6) 5 8.79 (d, J = 4.4 Hz, 1H), 8.77 (d, J = 1.2 Hz, 1H), 8.54 (d, J = 1.2 Hz, 1H), 7.44 (d, J = 4.4 Hz, 1H), 2.96 (s, 3H), 3.59 (s, 3H), 3.42 (s, 3H), 3.08 (q, J = 6.8 Hz, 2H), 1.34 (t, J = 7.2 Hz, 3H); ESI MS (m / z) 465.5 (MH)+.

[0447] Step-2: Synthesis of 2-(ethylsulfonimidoyl)-N-methoxy-N-methyl-3-(3-methyl-6-

[0448] (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide

[0449] To a stirred solution of 2-(ethylthio)-A-methoxy-A-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (500 mg, 1.07 mmol) in methanol (20 mL), iodobenzene diacetate (1038 mg, 3.22 mmol) was added followed by carbamic acid ammonium salt (335 mg, 4.30 mmol) at 0 °C. The resulting reaction mixture was stirred at 25 °C for 5 h. After the completion of the reaction, the reaction mixture was poured into water (100 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organic layers were washed with saturated brine solution (50 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product which was purified by flash column chromatography to obtain the desired 2-(ethylsulfonimidoyl)-A-methoxy-A-methyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (270 mg, 0.544 mmol, 50.6 % yield). 1H-NMR (400 MHz, DMSO-d6) 5 8.92 (d, J = 4.2 Hz, 1H), 8.84 (s, 1H), 8.61 (s, 1H), 7.70 (d, J = 3.9 Hz, 1H), 4.86 (s, 1H), 3.80 (s, 3H), 3.62 (s, 3H), 3.58-3.49 (m, 2H), 3.44 (s, 3H), 1.22 (t, J = 7.2 Hz, 3H); ESI MS (m / z) 497.05 (MH)+.

[0450] Example-10: Synthesis of 2-(ethylsulfonyl)-N-isopropoxy-2'-(trifluoromethyl)-[3,5'- bipyrazolo[l,5-a]pyrimidine]-7-carboxamide (Compound 181)

[0451] Step-1: Synthesis of tert-butyl 2-cyano-2-(2-(trifluoromethyl)pyrazolo[l,5-a]pyrimidin-5- yl)acetate

[0452] To a stirred solution of tert-butyl cyanoacetate (14.33 g, 101 mmol) in / V, / V-dimcthylfbmiamidc (200 mL), sodium hydride (60% by wt.; 4.06 g, 101 mmol) was added slowly at 0 °C, and the resulting mixture was stirred at 0 °C for 10 minutes followed by the addition of 5-bromo-2- (trifluoromethyl)pyrazolo[l,5-a]pyrimidine (WO2021165834) (18 g, 67.7 mmol) and the resulting mixture was stirred at 25 °C for 14 h. After the completion of the reaction, the reaction mixture was poured slowly into water (I L). The aqueous layer was extracted with ethyl acetate (4 x 250 mL) and the combined organic layers were washed with saturated brine solution (250 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product which was purified using flash column cromatography to obtain tert-butyl 2-cyano-2-(2- (trifluoromethyl)pyrazolo[l,5-a]pyrimidin-5-yl)acetate (15 g, 46.0 mmol, 67.9 % yield).1H-NMR (400 MHz, DMSO-de) 5 13.00 (s, 1H), 8.63 (d, J = 8.0 Hz, 1H), 6.84 (s, 1H), 6.71 (d, J = 8.4 Hz, 1H), 3.89 (s, 1H), 1.51 (s, 9H); ESI MS (m / z) 324.85 (MH) .

[0453] Step-2: Synthesis of 2-(2-(trifluoromethyl)pyrazolo[l,5-a]pyrimidin-5-yl)acetonitrile

[0454] To a stirred solution of tert-butyl 2-cyano-2-(2-(trifluoromethyl)pyrazolo[l,5-a]pyrimidin-5-yl)acetate (13 g, 39.8 mmol) in acetonitrile (130 mL), p-toluenesulfonic acid monohydrate (7.73 g, 39.8 mmol) was added and the resulting mixture was stirred at 80 °C for 3 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C and poured into water (250 mL). The aqueous layer was extracted with ethyl acetate (2 x 200 mL) and the combined organic layers were washed with satuarted aqueous NaHCCL solution (200 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product which was purified by flash column chromatography to obtain desired 2-(2-(trifluoromethyl)pyrazolo[l,5-a]pyrimidin-5-yl)acetonitrile (7.3 g, 32.3 mmol, 81 % yield). ’H-NMR (400 MHz, CHLOROFORM-tf) 5 8.77 (d, J = 7.2 Hz, 1H), 7.11 (d, J = 7.6 Hz, 1H), 6.97 (s, 1H), 4.03 (s, 2H); ESI MS (m / z) 224.95 (MH) .

[0455] Step-3: Synthesis of 3,3-bis(ethylthio)-2-(2-(trifluoromethyl)pyrazolo[l,5-a]pyrimidin-5- yl)acrylonitrile To a solution of potassium hydroxide (4.47 g, 80 mmol) in acetonitrile (150 mL), added 2-(2- (trifluoromethyl)pyrazolo[l,5-a]pyrimidin-5-yl)acetonitrile (9 g, 39.8 mmol) at 0 °C and the resulting mixture was stirred for 1 h at 25 °C. Then the reaction mixture was cooled to -5 °C and added dropwise, carbon disulfide (2.4 mL, 39.8 mmol) over 10 minutes. The resulted mixture was stirred for 1 h at -5 °C before the addition of ethyl iodie (6.43 mL, 80 mmol). The resulting reaction mixture was stirred for 2 h at 0 °C and then at 25 °C for 16 h. After the completion of the reaction, the reaction mixture was diluted with water (250 mL). Aqueous layer was extracted with ethyl acetate (2 x 250 mL) and the combined organic layers were washed with saturated brine solution (200 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product which was purified by flash column chromatography to obtain 3,3-bis(ethylthio)-2-(2- (trifluoromethyl)pyrazolo[l,5-a]pyrimidin-5-yl)acrylonitrile (11 g, 30.7 mmol, 77 % yield) as solid. 'H- NMR (400 MHz, DMSO-J6) 5 8.67 (d, J = 7.6 Hz, 1H), 7.38 (d, J = 7.6 Hz, 1H), 7.00 (s, 1H), 3.19 (q, J = 7.2 Hz, 2H), 3.08 (d, J = 7.2 Hz, 2H), 1.43 (t, J = 7.6 Hz, 3H), 1.32 (t, J = 7.6 Hz, 3H); ESI MS (m / z) 358.95 (MH)+

[0456] Step-4: Synthesis of 3-(ethylthio)-4-(2-(trifhioromethyl)pyrazolo[l,5-a]pyrimidin-5-yl)-lH- pyrazol-5-amine

[0457] To a stirred solution of 3,3-bis(ethylthio)-2-(2-(trifluoromethyl)pyrazolo[l,5-a]pyrimidin-5- yl)acrylonitrile (9 g, 25.1 mmol) in acetonitrile (90 mL) and ethanol (90 mL), hydrazine hydrate (1.37 mL, 27.6 mmol) was added dropwise at 0 °C and the resulting mixture was stirred at 25 °C for 1 h and then stirred at 75 °C for 14 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C and poured into water (I L). Aqueous layer was extracted with ethyl acetate (4 x 200 mL) and the combined organic layers were washed with saturated brine solution (250 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product which was washed with a solution of 20% ethylacetate in hexane to obatin the desired 3-(ethylthio)-4-(2- (trifluoromethyl)pyrazolo[l,5-a]pyrimidin-5-yl)-lH-pyrazol-5-amine (6.9 g, 21.02 mmol, 84 % yield) as solid. ’H-NMR (400 MHz, DMSO-J6) 5 12.09 (s, 1H), 9.02 (d, J = 7.6 Hz, 1H), 7.70 (d, J = 7.6 Hz, 1H), 6.94-6.89 (m, 3H), 3.04 (q, J = 6.8 Hz, 2H), 1.32 (t, J = 7.6 Hz, 3H); ESI MS (m / z) 329.00 (MH)+.

[0458] Step-5: Synthesis of ethyl 2-(ethylthio)-2'-(trifluoromethyl)-[3,5'-bipyrazolo[l,5-a]pyrimidine]- 7-carboxylate

[0459] To a stirred solution of 3-(ethylthio)-4-(2-(trifluoromethyl)pyrazolo[l,5-a]pyrimidin-5-yl)-lH-pyrazol- 5-amine (8 g, 24.37 mmol) in acetic acid (50 mL). ethyl (E)-4-ethoxy-2-oxobut-3-enoate (8.39 g, 48.7 mmol) was added at 25 °C and the reaction mixture was stirred at 100 °C for 4 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C then poured into water (500 mL). The aqueous layer was extracted with ethyl acetate (4 x 200 mL), and the combined organic layers were washed with saturated brine solution (250 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product which was purified by flash column chromatography to obtain the desired ethyl 2-(ethylthio)-2'-(trifluoromethyl)-[3,5'-bipyrazolo[l,5-a]pyrimidine]-7- carboxylate (5.6 g, 12.83 mmol, 52.7 % yield) as solid.. 'H-NMR (400 MHz, DMSO-t / 6) 5 8.67-8.64 (m, 2H), 8.49 (d, J = 7.6 Hz, 1H), 7.33 (d, J = 4.4 Hz, 1H), 6.95 (s, 1H), 4.59 (q, J = 7.2 Hz, 2H), 3.33 (q, J = 7.2 Hz, 2H), 1.57-1.49 (m, 6H); ESI MS (m / z) 437.10 (MH)+.

[0460] Step-6: Synthesis of ethyl 2-(ethylsulfonyl)-2'-(trifluoromethyl)-[3,5'-bipyrazolo[l,5- a]pyrimidine] -7 -carboxylate

[0461] The desired ethyl 2-(ethylsulfonyl)-2'-(trifluoromethyl)-[3,5'-bipyrazolo[l,5-a]pyrimidine]-7- carboxylate (4.2 g, 8.97 mmol, 93 % yield) was prepared from of ethyl 2-(ethylthio)-2'- (trifluoromethyl)-[3,5'-bipyrazolo[l,5-a]pyrimidine]-7-carboxylate (4.2 g, 9.62 mmol), using the similar procedure mentioned in step-8 of Example-1. 'H-NMR (400 MHz, DM SO-cT) 5 9.38 (dd, J = 7.3, 0.7 Hz, 1H), 9.06 (d, J = 4.2 Hz, 1H), 7.97 (d, J = 7.3 Hz, 1H), 7.88 (d, J = 4.2 Hz, 1H), 7.33 (s, 1H), 4.53 (q, J = 7.1 Hz, 2H), 3.92 (q, J = 7.4 Hz, 2H), 1.40 (t, J = 7.1 Hz, 3H), 1.32 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 468.90 (MH)+

[0462] Step-7: Synthesis of 2-(ethylsulfonyl)-2'-(trifluoromethyl)-[3,5'-bipyrazolo[l,5-a]pyrimidine]-7- carboxylic acid

[0463] The desired 2-(ethylsulfonyl)-2'-(trifluoromethyl)-[3,5'-bipyrazolo[l,5-a]pyrimidine]-7-carboxylic acid (3.5 g, 7.95 mmol, 93 % yield) was prepared from of ethyl 2-(ethylsulfonyl)-2'-(trifluoromethyl)- [3,5'-bipyrazolo[l,5-a]pyrimidine]-7-carboxylate (4 g, 8.54 mmol), using the similar procedure mentioned in step-6 of Example-1. 'H-NMR (400 MHz, DMSO-A) 5 9.36 (dd, J = 7.5, 0.8 Hz, 1H), 8.99 (d, J = 4.3 Hz, 1H), 8.01 (d, J = 7.3 Hz, 1H), 7.68 (d, J = 4.3 Hz, 1H), 7.31 (s, 1H), 3.94 (q, J = 7.4 Hz, 2H), 1.33-1.29 (m, 3H); ESI MS (m / z) 440.85 (MH)+

[0464] Step-8: Synthesis of 2-(ethylsulfonyl)-N-isopropoxy-2'-(trifluoromethyl)-[3,5'-bipyrazolo[l,5- a]pyrimidine] -7 -carboxamide

[0465] The desired 2-(ethylsulfonyl)-N-isopropoxy-2'-(trifluoromethyl)-[3,5'-bipyrazolo[l,5-a]pyrimidine]-7- carboxamide (90 mg, 0.181 mmol, 39.8 % yield) was prepared from of 2-(ethylsulfonyl)-2'- (trifluoromethyl)-[3,5'-bipyrazolo[l,5-a]pyrimidine]-7-carboxylic acid (200 mg, 0.454 mmol), using the similar procedure mentioned in step-7 of Example-1. 'H-NMR (400 MHz, DM SO-cT) 5 12.00 (s, 1H), 9.39 (dd, J = 7.5, 0.8 Hz, 1H), 9.05 (d, J = 4.3 Hz, 1H), 8.00 (d, J = 7.6 Hz, 1H), 7.78 (d, J = 4.3 Hz, 1H), 7.33 (s, 1H), 4.32-4.26 (m, 1H), 3.99-3.91 (m, 2H), 1.37-1.26 (m, 9H); ESI MS (m / z) 498.15 (MH)+.

[0466] Table-A: Representative compounds of the present disclosure were prepared according to the suitable methods as described in the respective schemes and chemistry examples.

[0467] Ill

[0468] * Compound names generated using Chemdraw Professional 23.1

[0469] In one embodiment, the present invention provides a composition for controlling or preventing invertebrate pests. The composition comprises a biologically effective amount of the compound of formula (I) and at least one additional component selected from the group consisting of surfactants and auxiliaries.

[0470] In yet another embodiment, the present invention provides a compound of formula (I) or its N-oxides and salts into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further composition types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6thEd. May 2008, CropLife International.

[0471] In one another embodiment of present invention provides a agrochemical compositions compound of formula (I), which comprise active substance between 0.01 and 95% by weight, preferably between 0.1 and 90%, and more preferably between 1 and 70 %, in particular between 10 and 60 by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

[0472] Water-soluble concentrates (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing.

[0473] Methods for applying or treating compound I and compositions thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and infurrow application methods of the propagation material. Preferably, compound I or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.

[0474] When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, in particular from 0.1 to 0.75 kg per ha.

[0475] In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 500 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seed) are generally required.

[0476] When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.

[0477] Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the present invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0478] The user can apply the composition according to the present invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and / or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the present invention is thus obtained. Usually, 20 to 6000 liters, preferably 35 to 1000 litres, more preferably 50 to 500 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.

[0479] According to one embodiment, individual components of the composition according to the present invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate. The compounds and compositions of the present invention are thus useful agronomically for protecting field crops from phytophagous invertebrate pests, and also nonagronomically for protecting other horticultural crops and plants from phytophagous invertebrate pests. This utility includes protecting crops and other plants (i.e. both agronomic and nonagronomic) that contain genetic material introduced by genetic engineering (i.e. transgenic) or modified by mutagenesis to provide advantageous traits.

[0480] The compounds of the present invention are characterized by favorable metabolic and / or soil residual patterns and exhibit activity controlling a spectrum of agronomic and non-agronomic invertebrate pests. The compounds of the present invention are preventively and / or curatively valuable active ingredients in the field of pest control, even at low rates of application, which can be used against insecticide resistant pests such as insects and mites, and are well tolerated by warm-blooded species, fish and plants. In the context of the present invention "invertebrate pest control" means inhibition of invertebrate pest development (including mortality) that causes significant reduction in feeding or other injury or damage caused by the pest; (related expressions are defined analogously.) As referred to in the present invention, 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.

[0481] The term "gastropod" includes snails, slugs and other Stylommatophora. The term "nematode" includes all of the helminths, such as: roundworms, heartworms, and phytophagous nematodes (Nematoda), flukes (Tematoda), Acanthocephala, and tapeworms (Cestoda). Those skilled in the art will recognize that not all compounds are equally effective against all pests.

[0482] The compounds of the present invention display activity against economically important agronomic pests in forest, greenhouse, nursery, ornamentals, turfgrass, food and fiber, public and animal health, domestic and commercial structure, household, and stored product pests. These include larvae of the order Lepidoptera, such as armyworms, cutworms, loopers, and heliothines in the family Noctuidae (e.g., fall armyworm (Spodoptera fugiperda J. E. Smith), beet armyworm (Spodoptera exigua Hubner), black cutworm (Agrotis ipsilon Hufnagel), cabbage looper (Trichoplusia ni Hubner), tobacco budworm (Heliothis virescens Fabricius)); borers, casebearers, webworms, coneworms, cabbageworms and skeletonizers from the family Pyralidae (e.g., European corn borer (Ostrinia nubilalis Hubner), navel orangeworm (Amyelois transitella Walker), corn root webworm (Crambus caliginosellus Clemens), sod webworm (Herpetogramma licarsisalis Walker)); leafrohers, budworms, seed worms, and fruit worms in the family Tortricidae (e.g., codling moth (Cydia pomonella Linnaeus), grape berry moth (Endopiza viteana Clemens), oriental fruit moth (Grapholita molesta Busck)); and many other economically important lepidoptera (e.g., diamondback moth (Plutella xylostella Linnaeus), pink bollworm (Pectinophora gossypiella Saunders), gypsy moth (Lymantria dispar Linnaeus)); nymphs and adults of the order Blattodea mcluding cockroaches from the families Blattellidae and Blattidae (e.g., oriental cockroach (Blatta orientalis Linnaeus), Asian cockroach (Blatella asahinai Mizukubo), German cockroach (Blattella gemnanica Linnaeus), brownbanded cockroach (Supella longipalpa Fabricius), American cockroach (Periplaneta americana Linnaeus), brown cockroach (Periplaneta brunnea Burmeister), Madeira cockroach (Leitcophaea maderae Fabricius)); foliar feeding larvae and adults of the order Coleoptera including weevils from the families Anthribidae, Bruchidae, and Curculionidae (e.g., boll weevil (Anthonomus grandis Boheman), rice water weevil (Lissorhoptrus oryzophilus Kuschel), granary weevil (Sitophilus granarius Linnaeus), rice weevil (Sitophilus oryzae Linnaeus)); flea beetles, cucumber beetles, rootworms, leaf beetles, potato beetles, and leafminers in the family Chrysomelidae (e.g., Colorado potato beetle (Leptinotarsa decemlineata Say), western corn rootworm (Diabrotica virgifera virgifera LeConte)); chafers and other beetles from the family Scaribaeidae (e.g., Japanese beetle (Popillia japonica Newman) and European chafer (Rhizotrogus majalis Razoumowsky)); carpet beetles from the family Dermestidae; wireworms from the family Elateridae; bark beetles from the family Scolytidae and flour beetles from the family Tenebrionidae. In addition it includes: adults and larvae of the order Dermaptera including earwigs from the family Forficulidae (e.g., European earwig (Forficula auricularia Linnaeus), black earwig (Chelisoches mono Fabricius)); adults and nymphs of the orders Hemiptera and Homoptera such as, plant bugs from the family Miridae, cicadas from the family Cicadidae, leafhoppers (e.g. Empoasca spp.) from the family Cicadellidae, planthoppers from the families Fulgoroidae and Delphacidae, treehoppers from the family Membracidae, psyllids from the family Psyllidae, whitefiies from the family Aleyrodidae, aphids from the family Aphididae, phylloxera from the family Phylloxeridae, mealybugs from the family Pseudococcidae, scales from the families Coccidae, Diaspididae and Margarodidae, lace bugs from the family Tingidae, stink bugs from the family Pentatomidae, cinch bugs (e.g., Blissus spp.) and other seed bugs from the family Lygaeidae, spittlebugs from the family Cercopidae squash bugs from the family Coreidae, and red bugs and cotton Stainers from the family Pyrrhocoridae. Also included are adults and larvae of the order Acari (mites) such as spider mites and red mites in the family Tetranychidae (e.g., European red mite (Panonychus ulmi Koch), two spotted spider mite (Tetranychus urticae Koch), McDaniel mite (Tetranychus mcdanieli McGregor)), flat mites in the family Tenuipalpidae (e.g., citrus flat mite (Brevipalpus lewisi McGregor)), rust and bud mites in the family Eriophyidae and other foliar feeding mites and mites important in human and animal health, i.e. dust mites in the family Epidermoptidae, follicle mites in the family Demodicidae, grain mites in the family Glycyphagidae, ticks in the order Ixodidae (e.g., deer tick (Ixodes scapularis Say), Australian paralysis tick (Ixodes holocyclus Neumann), American dog tick (Dermacentor variabilis Say), lone star tick (Amblyomma americanum Linnaeus) and scab and itch mites in the families Psoroptidae, Pyemotidae, and Sarcoptidae; adults and immatures of the order Orthoptera including grasshoppers, locusts and crickets (e.g., migratory grasshoppers (e.g., Melanoplus sanguinipes Fabricius, M. differentialis Thomas), American grasshoppers (e.g., Schistocerca americana Drury), desert locust (Schistocerca gregaria Forskal), migratory locust (Locusta migratoria Linnaeus), house cricket (Acheta domesticus Linnaeus), mole crickets (Gryllotalpa spp. ', adults and immatures of the order Diptera including leafminers, midges, fruit flies (Tephritidae), frit flies (e.g., Oscinella frit Linnaeus), soil maggots, house flies (e.g., Musca domestica Linnaeus), lesser house flies (e.g., Fannia canicularis Linnaeus, F.femoralis Stein), stable flies (e.g., Stomoxys calcitrans Linnaeus), face flies, horn flies, blow flies (e.g., Chiysomya spp., Phonnia spp.), and other muscoid fly pests, horse flies (e.g., Tabanus spp.), botflies (e.g., Gastrophilus spp., Oestrus spp.), cattle grubs (e.g., Hypoderma spp.), deer flies (e.g., Chrysops spp.), keds (e.g., Melophagus ovinus Linnaeus) and other Brachycera, mosquitoes (e.g., Aedes spp., Anopheles spp., Culex spp.), black flies (e.g., Prosimulium spp., Simulium spp.), biting midges, sand flies, sciarids, and other Nematocera; adults and immatures of the order Thysanoptera including onion thrips (Thrips tabaci Lindeman) and other foliar feeding thrips; insect pests of the order Hymenoptera including ants (e.g., red carpenter ant (Camponotus ferrugineus Fabricius), black carpenter ant (Camponotus pennsylvanicus De Geer), Pharaoh ant (Monomorium pharaonis Linnaeus), little fire ant (Wasmannia auropunctata Roger), fire ant (Solenopsis geminata Fabricius), red imported fire ant (Solenopsis Invicta Buren), Argentine ant (Iridomyrmex humilis Mayr), crazy ant (Paratrechina longicornis Latreille), pavement ant (Tetramorium caespitum Linnaeus), cornfield ant (Las ins alienus FSrster), odorous house ant (Tapinoma sessile Say)), bees (including carpenter bees), hornets, yellow jackets and wasps; insect pests of the order Isoptera including the eastern subterranean termite (Reticulitermes flavipes Kollar), western subterranean termite (Reticulitermes hesperus Banks), Formosan subterranean termite (Coptotermes formosanus Shiraki), West Indian dry wood termite ( Incisite rmes immigrans Snyder) and other termites of economic importance; insect pests of the order Thysanura such as silverfish (Lepisma saccharina Linnaeus) and firebrat (Thermobia domestica Packard); insect pests of the order Mallophaga including the head louse (Pediculus humanus capitis De Geer), body louse (Pediculus humanus humanus Linnaeus), chicken body louse (Menacanthus stramineus Nitszch), dog biting louse (Trichodectes cams De Geer), fluff louse (Goniocotes gallinae De Geer), sheep body louse (Bovicola ovis Schrank), short-nosed cattle louse (Haematopinus eurystemus Nitzsch), long-nosed cattle louse (Linognathus vituli Linnaeus) and other sucking and chewing parasitic lice that attack man and animals; insect pests of the order Siphonoptera including the oriental rat flea (Xenopsylla cheopis Rothschild), cat flea (Ctenocephalides felis Bouche), dog flea (Ctenocephatides canis Curtis), hen flea (Ceratophyllus gallinae Schrank), sticktight flea (Echidnophaga gallinacea Westwood), human flea (Pulex irritans Linnaeus) and other fleas afflicting mammals and birds. Additional arthropod pests covered include: spiders in the order Araneae such as the brown recluse spider (Loxosceles reclusa Gertsch and Mulaik) and the black widow spider (Latrodectus mactans Fabricius), and centipedes in the order Scutigeromorpha such as the house centipede ( Scuti gera coleoptrata Linnaeus). Activity also includes members of the Classes Nematoda, Cestoda, Trematoda, and Acanthocephala including economically important members of the orders Strongylida, Ascaridida, Oxyurida, Rhabditida, Spirurida, and Enoplida such as but not limited to economically important agricultural pests (i.e. root knot nematodes in the genus Meloidogyne, lesion nematodes in the genus Pratylenchus, stubby root nematodes in the genus Trichodorus, etc.) and animal and human health pests (i.e. all economically important flukes, tapeworms, and roundworms, such as Strongylus vulgaris in horses, Toxocara canis in dogs, Haemonchus contortus in sheep, Dirofllaria immitis Leidy in dogs, Anoplocephala peifoliata in horses, Fasciola hepatica Linnaeus in ruminants, etc.).

[0483] The compounds of the present invention show particularly high activity against pests in the order of Lepidoptera (e.g., Alabama argillacea Hubner (cotton leaf worm), Archips argyrospila Walker (fruit tree leaf roller), A. rosana Linnaeus (European leaf roller) and other Archips species, Chilo suppressalis Walker (rice stem borer), Cnaphalocrosis medinalis Guenee (rice leaf roller), Crambus caliginosellus Clemens (corn root webworm), Crambus teterrellus Zincken (bluegrass webworm), Cydia pomonella Linnaeus (codling moth), Earias insulana Boisduval (spiny bollworm), Earias vittella Fabricius (spotted boll worm), Helicoveipa armigera Hubner (American bollworm), Helicoverpa z.ea Boddie (corn earworm), Heliothis virescens Fabricius (tobacco budworm), Herpetogramma licarsisalis Walker (sod webworm), Lobesia botrana Denis and Schiffermuller (grape berry moth), Pectinophora gossypiella Saunders (pink bollworm), Phyllocnistis citrella Stainton (citrus leafminer), Pieris brassicae Linnaeus (large white butterfly), Pieris rapae Linnaeus (small white butterfly), Plutella xylostella Linnaeus (diamondback moth), Spodoptera exigua Hubner (beet armyworm), Spodoptera litura Fabricius (tobacco cutworm, cluster caterpillar), Spodoptera frugiperda J. E. Smith (fall armyworm), Trichoplusia ni Hubner (cabbage looper) and Tula absoluta Meyrick (tomato leafminer)). Compounds of the present invention also have commercially significant activity on members from the order Homoptera including: Acyrthisiplionpisum Harris (pea aphid), Aphis craccivora Koch (cowpea aphid), Aphis fabae Scopoli (black bean aphid), Aphis gossypii Glover (cotton aphid, melon aphid), Aphis pomi De Geer (apple aphid), Aphis spiraecola Patch (spirea aphid), Aulacorthum solani Kaltenbach (foxglove aphid), Chaetosiphon fragaefolii Cockerell (strawberry aphid), Diuraphis noxia Kurdjumov / Mordvilko (Russian wheat aphid), Dysaphis plantaginea Paaserini (rosy apple aphid), Eriosoma lanigerum Hausmann (woolly apple aphid), Hyalopterus pruni Geoffroy (mealy plum aphid), Lipaphis erysimi Kaltenbach (tarnip aphid), Metopolophium dirrhodum Walker (cereal aphid), Macrosipum euphorbiae Thomas (pqtato aphid), Myzus persicae Sulzer (peach-potato aphid, green peach aphid), Nasonovia ribisnigri Mosley (lettuce aphid), Pemphigus spp. (root aphids and gall aphids), Rhopalosiphum maidis Fitch (corn leaf aphid), Rhopalosiphum padi Linnaeus (bird cherry-oat aphid), Schizaphis graminum Rondani (greenbug), Sitobion avenae Fabricius (English grain aphid), Therioaphis maculata Buckton (spotted alfalfa aphid), Toxoptera aurantii, Boyer de Fonscolombe (black citrus aphid), and Toxoptera citiicida Kirkaldy (brown citrus aphid); Adelges spp. (adelgids); Phylloxera devastatrix Pergande (pecan phylloxera); Bemisia tabaci Gennadius (tobacco whitefly, sweetpotato whitefly), Bemisia argentifolii Bellows and Perring (silverleaf whitefly), Dialeurodes citri Ashmead (citrus whitefly) and Trialeurodes vaporariorum Westwood (greenhouse whitefly); Empoasca fabae Harris, (potato leafhopper), Laodelphax striatellus Fallen (smaller brown planthopper), Macrolestes quadrilineatus Forbes (aster leafhopper), Nephotettix cinticeps Uhler (green leafhopper), Nephotettix nigr opictus Stal (rice leafhopper), Nilaparvata lugens Stal (brown planthopper), Peregrinus maidis Ashmead (corn planthopper), Sogatella furcifera Horvath (white - backed planthopper), Sogatodes orizicola Muir (rice delphacid), Typhlocyba pomaria McAfee white apple leafhopper, Erythroneoura spp. (grape leafhoppers); Magicidada septendecim Linnaeus (periodical cicada); Icerya purchasi Maskell (cottony cushion scale), Quadraspidiotus perniciosus Comstock (San Jose scale); Pianococcus citri Risso (citrus mealybug); Pseudococcus spp. (other mealybug complex); Cacopsylla pyricola Foerster (pear psylla), Trioz.a diospyri Ashmead (persimmon psylla).

[0484] These compounds also have activity on members from the order Hemiptera including: Acrostemum hilare Say (green stink bug), Anasa tristis De Geer (squash bug), Blissus leucopterus leucopterus Say (chinch bug), Corythuca gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), Dysdercus suturellus Herrich-S chaffer (cotton Stainer), Euchistus servus Say (brown stink bug), Euchistus variolrius Palisot deBeauvois (one-spotted stink bug), Graptosthetus spp. (complex of seed bugs), Leptoglossus corculus Say (leaf- footed pine seed bug), Lygus lineolaris Palisot de Beauvois (tarnished plant bug), Nezara viridula Linnaeus (southern green stink bug), Oebalus pugnax Fabricius (rice stink bug), Oncopeltus fasciatus DaEas (large milkweed bug), Pseudatomoscelis seriatus Reuter (cotton fleahopper).

[0485] Other insect which are controlled by compounds of formula (I) of the present invention include: Thysanoptera (e.g., Frankliniella occidentalis Pergande (western flower thrip), Scirthothrips citri Moulton (citrus thrip), Sericothrips variabilis Beach (soybean thrip), and Thrips tabaci Lindeman (onion thrip); and the order Coleoptera (e.g., Leptinotarsa decemlineata Say (Colorado potato beetle), Epilachna varivestis Mulsant (Mexican bean beetle) and wireworms of the genera Agriotes, Athous or Limonius).

[0486] Particularly, the compounds of formula (I), their N-oxides, their isomers, their polymorphs and their salts are especially suitable for efficiently combating the following pests: Insects from the order of the lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Chilo infuscatellus, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Earias vittella, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholita funebrana, Grapholita molesta, Helicoverpa armigera, Helicoverpa virescens, Helicoverpa zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Leucinodes orbonalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scirpophaga incertulas, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Spodoptera exigua, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis', and

[0487] Beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscuras, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aphthona euphoridae, Athous haemorrhoidalis, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Ctenicera ssp., Diabrotica longicornis, Diabrotica semipunctata, Diabrotica undecimpunctata Diabrotica speciosa, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius califomicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllobius pyri, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popilliajaponica, Sitona lineatus and Sitophilus granaria; flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inomata, Culiseta melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga haemorrhoidalis, Sarcophaga spp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, Tipula oleracea, and Tipula paludosa; termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes grassei, Termes natalensis, and Coptotermes formosanus; cockroaches (Blattaria Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalist ants, bees, wasps, sawflies (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Atta capiguara, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Lasius niger, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex californicus, Pheidole megacephala, Dasymutilla occidentalis, Bombus spp., Vespula squamosa, Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolichovespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile; crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta domestica, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Calliptamus italicus, Chortoicetes terminifera, and Locustana pardalina; Araneida, e.g. Latrodectus mactans, and Loxosceles reclusa; fleas (Siphonaptera), e.g. Ctenocephalidesfelis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus, silverfish, firebrat (Thysanura), e.g. Lepisma saccharina and Thermobia domestica, centipedes (Chilopoda), e.g. Scutigera oleoptrata, millipedes (Diplopoda), e.g. Narceus spp., Earwigs (Dermaptera), e.g. forficula auricularia, lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon allinae, Menacanthus stramineus and Solenopotes capillatus. Collembola (springtails), e.g. Onychiurus ssp.

[0488] The compounds of formula (I) of the present invention are also suitable for controlling Nematodes: plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes, Rotylenchus robustus and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species.

[0489] The compounds of formula (I) and their salts are also useful for controlling arachnids (Arachnoidea), such as acarians (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis.

[0490] In one embodiment of the present invention, the present invention provides the compound of formula (I) is useful for controlling insects selected form sucking or piercing insects such as insects from the genera Thysanoptera, Diptera and Hemiptera, in particular the following species:

[0491] Thysanoptera: Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,

[0492] Diptera: Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freebomi, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga haemorrhoidalis, Sarcophaga spp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, Tipula oleracea, and Tipula paludosa;

[0493] Hemiptera, in particular aphids: Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus homi, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mail, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantiiand, and Viteus vitifolii.

[0494] In one embodiment, the present invention provides a composition comprising a biologically effective amount of the compound of formula (I) and at least one additional biological active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients.

[0495] In one embodiment, the present invention provides a combination comprising a biologically effective amount of the compound of formula (I) according to claim 1 and at least one additional biological active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers or nutrients.

[0496] The compounds used in the composition and in combination with the compound of formula (I) are also termed as active compatible compounds.

[0497] The known and reported fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics and nutrients can be combined with at least one compound of the formula (I) of the present disclosure. For example, fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients disclosed and reported in WO2016156129 and / or W02017153200 can be combined with at least one compound of formula (I) of the present disclosure.

[0498] The fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients reported in WO2016156129 and or W02017153200 are incorporated herein by way of reference as non-limiting examples to be combined with at least one compound of the formula (I) of the present disclosure.

[0499] Particularly, the compounds of the present invention can be mixed with at least one additional biological active compatible compound (mixing partner) which includes but is not limited to insecticides, fungicides, nematocides, bactericides, acaricides, growth regulators such as rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural utility.

[0500] Examples of such biologically active compounds or agents / mixing partners with which compound of formula (I) of the present invention can be combined / formulated are disclosed in the W02019072906A1 (pages 27 to 37).

[0501] In one embodiment, the biological agents for mixing with compounds of the present invention include Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin as well as naturally occurring and genetically modified viral insecticides including members of the family Baculoviridae as well as entomophagous fungi.

[0502] In certain instances, combinations with other invertebrate pest control compounds or agents having a similar spectrum of control but a different mode of action will be particularly advantageous for resistance management. Thus, compositions of the present invention can further comprise a biologically effective amount of at least one additional invertebrate pest control compounds or agents having a similar spectrum of control but a different mode of action. Contacting a plant genetically modified to express a plant protection compound (e.g., protein) or the locus of the plant with a biologically effective amount of a compound of the invention can also provide a broader spectrum of plant protection and be advantageous for resistance management.

[0503] In one embodiment of the present invention, the biologically effective amount of the compound of formula (I) in the compositions ranges from 0.1 % to 99% by weight with respect to the total weight of the composition, preferably from 5% to 50% by weight with respect to the total weight of the composition.

[0504] The present invention furthermore provides a method of combating invertebrate pests, said method comprising contacting the invertebrate pests, their habitat, breeding ground, food supply, plant, seed, soil, area, material or environment in which the invertebrate pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from pest attack or infestation with a biologically effective amount of the compound or the composition of the present invention.

[0505] Invertebrate pests are controlled and protection of agronomic, horticultural and specialty crops, animal and human health is achieved by applying one or more of the compounds of the present invention, in an effective amount, to the environment of the pests including the agronomic and / or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled. Thus, the present invention further comprises a method for the control of foliar- and soil-inhabiting invertebrates and protection of agronomic and / or nonagronomic crops, comprising contacting the invertebrates or their environment with a biologically effective amount of one or more of the compounds of the present invention, or with a composition comprising at least one such compound or a composition comprising at least one such compound and an effective amount of at least one additional biologically active compound or agent. A preferred method of contact is by spraying. Alternatively, a granular composition comprising a compound of the present invention can be applied to the plant foliage or the soil. Compounds of the present invention are effective in delivery through plant uptake by contacting the plant with a composition comprising a compound of the present invention applied as a soil drench of a liquid formulation, a granular formulation to the soil, a nursery box treatment or a dip of transplants. Other methods of contact include application of a compound or a composition of the present invention by direct and residual sprays, aerial sprays, seed coats, microencapsulations, systemic uptake, baits, eartags, boluses, foggers, fumigants, aerosols, dusts and many others.

[0506] The compounds of the present invention can be incorporated into baits that are consumed by the invertebrates or within devices such as traps and the like. Granules or baits comprising between 0.01- 5% active ingredient, 0.05-10% moisture retaining agent(s) and 40-99% vegetable flour are effective in controlling soil insects at very low application rates, particularly at doses of active ingredient that are lethal by ingestion rather than by direct contact. The compounds of the present invention can be applied in their pure state, but most often application will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use. A preferred method of application involves spraying a water dispersion or refined oil solution of the compounds. Combinations with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butpxide often enhance compound efficacy.

[0507] The rate of application required for effective control (i.e. "biologically effective amount") will depend on such factors as the species of invertebrate to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal circumstances, application rates of about 0.01 to 2 kg of active ingredient per hectare are sufficient to control pests in agronomic ecosystems, but as little as 0.0001 kg / hectare may be sufficient or as much as 8 kg / hectare may be required. For nonagronomic applications, effective use rates will range from about 1.0 to 50 mg / square meter but as little as 0.1 mg / square meter may be sufficient or as much as 150 mg / square meter may be required. One skilled in the art can easily determine the biologically effective amount necessary for the desired level of invertebrate pest control. The animal pest, i.e. the insects, arachnids and nematodes, the plant, soil or water in which the plant is growing can be contacted with compounds of formula (I), their N-oxides and salts or composition(s) containing them by any application method known in the art. As such, "contacting" includes both direct contact (applying the compounds / compositions directly on the animal pest or plant typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds / compositions to the locus of the animal pest or plant).

[0508] The compounds of the present invention or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by animal pests, especially insects, acaridae or arachnids by contacting the plant / crop with a pesticidally effective amount of at least one compound of the present invention. The term "crop" refers both to growing and harvested crops.

[0509] In one embodiment, the present invention provides a method for protecting crops from attack or infestation by invertebrate pests, which comprises contacting the crop with a biologically effective amount of the compound or the composition of the present invention, isomer, polymorph, N-oxide or salt thereof.

[0510] The compounds of the present invention are employed as such or in form of compositions by treating the insects or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from insecticidal attack with an insecticidally effective amount of the active compounds. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the insects.

[0511] In one embodiment, the present invention provides to a method for the protection of seeds from soil insects and of the seedlings roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and / or after pre-germination with the compound or the composition of the present invention, N-oxide or salt thereof.

[0512] Furthermore, the present invention provides a method for treating or protecting animals against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the animals a biologically effective amount of compound or composition of the present invention, isomer, polymorph, N-oxide or veterinary acceptable salt thereof.

[0513] For use in treating crop plants, the rate of application (applying effective dosages) of the compound of the present invention may be in the range of 1 gai to 5000 gai per hectare in agricultural or horticultural crops, preferably from 25 g to 600 g per hectare, more preferably from 50 g to 500 g per hectare.

[0514] The compounds and the compositions of the present invention are particularly useful in the control of a multitude of insects on various cultivated plants, such as cereal, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin / squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium / pelargoniums, pansies and impatiens.

[0515] Particularly, the compound or the composition of the present invention are useful in protecting agricultural crops such as cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and other vegetables, and ornamentals.

[0516] The compounds of the present invention are effective through both contact (via soil, glass, wall, bed net, carpet, plant parts or animal parts), and ingestion (bait or plant part). The compounds of the present invention may also be applied against non-crop invertebrate pests, such as ants, termites, wasps, flies, mosquitos, crickets, or cockroaches. For use against said non-crop pests, compounds of the present invention are preferably used in a bait composition.

[0517] The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks. Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources. Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickyness, moisture retention or aging characteristics. The bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, from animal and / or plant proteins (meat-, fish or blood meal, insect parts, egg yolk), from fats and oils of animal and / or plant origin, or mono-, oligo or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.

[0518] For use in bait compositions, the typical content of active ingredient is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active compound.

[0519] Formulations of compounds of the present invention as aerosols (e.g in spray cans), oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents such as lower alcohols (e.g. methanol, ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocarbons (e.g. kerosenes) having boiling ranges of approximately 50 to 250 °C, Ai,A imethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.

[0520] The oil spray formulations differ from the aerosol recipes in that no propellants are used. For use in spray compositions, the content of active ingredient is from 0.001 to 80 weights %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %.

[0521] The compounds of the present invention and their respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems. The methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of formula (I) and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like. Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder. Suitable repellents for example are N, JV-diethyl-meta-toluamide (DEET), / V, / V-dicthylphcnylacctamidc (DEP A), 1 -(3-cyclohexan-l-yl- carbonyl)-2-methylpiperine, (2hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-l ,3-hexandiol, indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insect control such as {(+ / -)-3- allyl-2-methyl4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate (Esbiothrin), a repellent derived from or identical with plant extracts like limonene, eugenol, (+)-Eucamalol (1 ), (-)-l-epi-eucamalol or crude plant extracts from plants like Eucalyptus maculata, Vitex rotundifolia, Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogan nartdus (citronella). Suitable binders are selected for example from polymers and copolymers of vinyl esters of aliphatic acids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2- ethylhexylacrylate, and methyl acrylate, monoand di-ethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadiene.

[0522] The impregnation of curtains and bednets is done in general by dipping the textile material into emulsions or dispersions of the insecticide or spraying them onto the nets.

[0523] The compounds of the present invention and their compositions can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electrie wires and cables etc. from ants and / or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities). The compounds of the present invention are applied not only to the surrounding soil surface or into the under-floor soil in order to protect wooden materials but it can also be applied to lumbered articles such as surfaces of the underfloor concrete, alcove posts, beams, plywoods, furniture, etc., wooden articles such as particle boards, half boards, etc. and vinyl articles such as coated electric wires, vinyl sheets, heat insulating material such as styrene foams, etc.

[0524] In case of application against ants doing harm to crops or human beings, a compound of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like.

[0525] In one embodiment, the present invention provides a method for combating insects and mite pests comprising contacting the insects and mite pests, their habitat, breeding ground, food supply, plant, seed, soil, area, material or environment in which the insect and mite pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from pest attack or infestation with a biologically effective amount of compound of formula (I) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof, composition and combination thereof comprising the compound of formula (I).

[0526] In another embodiment, the present invention provides a method for protecting crops from attack or infestation by insects and mite pests comprises contacting the crop with the compound of formula (I) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof according to claim 1, composition and combination thereof comprising the compound of formula (1).

[0527] In yet another embodiment, the present invention provides a method, wherein said method comprises applying effective dosages of the compound of formula (I) in amounts ranging from 1 gai to 5000 gai per hectare in agricultural or horticultural crops.

[0528] In yet another embodiment, the present invention provides a method for the protection of seeds, plants and plant parts from soil insects and of the seedlings roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and / or after pre -germination with the compound of formula (I) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof, composition and combination thereof comprising the compound of formula (I).

[0529] In yet another embodiment, the present invention provides use of the compound of formula (I) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof, composition and combination thereof comprising the compound of formula (I), for combating insects and mite pests in agricultural crops, horticultural crops, household and vector control and parasites on animals.

[0530] Seed treatment

[0531] The present invention further provides a treated seed comprising the compounds of the present invention, particularly in an amount ranging from about 0.0001% to about 1% by weight of the seed before treatment.

[0532] The compounds of the present invention are also suitable for the treatment of seeds in order to protect the seed from insect pests, in particular from soil-living insect and mite pests and the resulting plant's roots and shoots against soil pests and foliar insects.

[0533] The compounds of the present invention are particularly useful for the protection of the seed from soil pests and the resulting plants roots (white grub, termites, wire worms) and shoots against soil pests and foliar insects. The protection of the resulting plants roots and shoots is preferred. More preferred is the protection of resulting plants shoots from piercing and sucking insects, wherein the protection from aphids, jassids, thrips and white fly is most preferred.

[0534] The present invention therefore comprises a method for the protection of seeds from insects, in particular from soil insects and of the seedling roots and shoots from insects, in particular from soil and foliar insects, said method comprising contacting the seeds before sowing and / or after pregermination with a compound of the present invention thereof. Particularly preferred is a method, wherein the plants roots and shoots are protected, more preferably a method, wherein the plants shoots are protected from piercing and sucking insects, most preferably a method, wherein the plants shoots are protected from aphids.

[0535] The term seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like and means in a preferred embodiment true seeds.

[0536] The term seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting.

[0537] The present invention also comprises seeds coated with or containing the active compound. The seeds can be coated with seed coating compositions containing the compounds of the present invention. For example, seed coating compositions reported in EP3165092, EP3158864, WO2016198644, WO2016039623, WO2015192923, CA2940002, US2006150489, US2004237395, WO2011028115, EP2229808, W02007067042, EP1795071, EP1273219, W0200178507, EP1247436, NL1012918 and CA2083415.

[0538] The term "coated with and / or containing" generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the propagation product is (re)planted, it may absorb the active ingredient along with moisture.

[0539] Suitable seed is seeds of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin / squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium / pelargoniums, pansies and impatiens.

[0540] In addition, the compounds of the present invention may be used for treating seed from plants, which tolerate the action of herbicides or fungicides or insecticides owing to breeding, including genetic engineering methods.

[0541] For example, the compound of the present invention can be employed in treatment of seeds from plants, which are resistant to herbicides from the group consisting of the sulfonylureas, imidazolinones, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active substances (see for example, EP0242236, EP0242246) (W092 / 00377) (EP0257993, US5013659) or in transgenic crop plants, for example cotton, with the capability of producing Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP0142924, EP0193259).

[0542] Furthermore, the compound of the present invention can be used for the treatment of seeds from plants, which have modified characteristics in comparison with existing plants, which can be generated for example by traditional breeding methods and / or the generation of mutants, or by recombinant procedures). For example, a number of cases have been described of recombinant modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g. WO92 / 11376, WO92 / 14827, WO91 / 19806) or of transgenic crop plants having a modified fatty acid composition (WO91 / 13972).

[0543] The seed treatment application of the compound of the present invention is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.

[0544] Compositions which are especially useful for seed treatment are e.g.:

[0545] A. Soluble concentrates (SL, LS)

[0546] B. Emulsions (EW, EO, ES)

[0547] C. Suspensions (SC, OD, FS)

[0548] D. Water-dispersible granules and water-soluble granules (WG, SG)

[0549] E. Water-dispersible powders and water-soluble powders (WP, SP, WS)

[0550] F. Gel-Formulations (GF)

[0551] G. Dustable powders (DP, DS)

[0552] Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter.

[0553] In one embodiment an FS formulation is used for seed treatment. Typcially, a FS formulation may comprise 1-800 g / 1 of active ingredient, 1-200 g / 1 Surfactant, 0 to 200 g / 1 antifreezing agent, 0 to 400 g / 1 of binder, 0 to 200 g / 1 of a pigment and up to 1 liter of a solvent, preferably water.

[0554] Especially FS formulations of compounds of the present invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g / 1) of the active ingredient, from 0.1 to 20 % by weight (1 to 200 g / 1) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and / or a dye, from 0 to 40 % by weight, e.g. 1 to 40 % by weight of a binder (sticker / adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler / vehicle up to 100 % by weight.

[0555] Seed treatment formulations may additionally comprise binders and optionally colorants.

[0556] Binders can be added to improve the adhesion of the active materials on the seeds after treatment. Suitable binders are homo and copolymers from alkylene oxides like ethylene oxide or propylene oxide, polyvinylacetate, polyvinylalcohols, polyvinylpyrrolidones, and copolymers thereof, ethylene -vinyl acetate copolymers, acrylic homo and copolymers, polyethyleneamines, polyethyleneamides and polyethylenepyrimidines, polysaccharides like celluloses, tylose and starch, polyolefin homo and copolymers like olefin / maleic anhydride copolymers, polyurethanes, polyesters, polystyrene homo and copolymers.

[0557] Optionally, also colorants can be included in the formulation. Suitable colorants or dyes for seed treatment formulations are Rhodamin B, C.I. Pigment Red 1 12, C.I. Solvent Red 1 , pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.

[0558] An example of a gelling agent is carrageen (Satiagel®).

[0559] In the treatment of seed, the application rates of the compounds of the present invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed. The present invention therefore also provides to seeds comprising a compound of formula (I), or an agriculturally useful salt of I, as defined herein. The amount of the compound I or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.

[0560] In one embodiment, the present invention provides a seed comprising a compound of formula (I) or salts, metal complexes, N-oxides, stereoisomers, polymorphs thereof, composition and combination thereof comprising the compound of formula (I), wherein the amount of compound of formula (I) in said seed ranging from about 0.0001 % to about 1 % by weight.

[0561] Animal health

[0562] The present invention also provides an agricultural and / or veterinary composition comprising at least one compound of the present invention.

[0563] The present invention still further relates to a use of the compound, N-oxide or veterinarily acceptable salt thereof or the composition of the present invention in the preparation of a medicament for treating or protecting animals against infestation or infection by invertebrate pests or parasites.

[0564] The compounds of formula (I), their N-oxides and / or veterinarily acceptable salts thereof are in particular also suitable for being used for combating parasites in and on animals.

[0565] One object of the present invention is therefore to provide new methods to control parasites in and on animals. Another object of the present invention is to provide safer pesticides for animals. Another object of the present invention is to provide pesticides for animals that may be used in lower doses than existing pesticides. Another object of the present invention is to provide pesticides for animals, which provide a long residual control of parasites. The present invention also relates to compositions containing a parasiticidally effective amount of at least one compound of formula (I), N-oxide or veterinarily acceptable salt thereof and an acceptable carrier, for combating parasites in and on animals.

[0566] The present invention also provides a method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises orally, topically, or parenteral administering or applying to the animals a parasiticidally effective amount of a compound of the present invention or a composition comprising it.

[0567] The present invention also provides a process for the preparation of a composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises a parasiticidally effective amount of a compound of the present invention or a composition comprising it.

[0568] Activity of compounds against agricultural pests does not suggest their suitability for control of endo and ectoparasites in and on animals which requires, for example, low, non-emetic dosages in the case of oral application, metabolic compatibility with the animal, low toxicity, and a safe handling.

[0569] Surprisingly it has now been found that compounds of the present invention are suitable for combating endo and ectoparasites in and on animals.

[0570] Compounds of the present invention and compositions comprising them are preferably used for controlling and preventing infestations and infections in animals including warm-blooded animals (including humans) and fish. They are for example suitable for controlling and preventing infestations and infections in mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as freshand salt-water fish such as trout, carp and eels.

[0571] Compounds of the present invention and compositions comprising them are preferably used for controlling and preventing infestations and infections in domestic animals, such as dogs or cats.

[0572] Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal hots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.

[0573] The compounds of the present invention and compositions comprising them are suitable for systemic and / or non-systemic control of ecto and / or endoparasites. They can be active against all or some stages of development.

[0574] The compounds of the present invention are especially useful for combating ectoparasites.

[0575] The compounds of the present invention are especially useful for combating parasites of the following orders and species, respectively: fleas (Siphonaptera), e.g. Ctenocephalides fells, Ctenocephalides cams, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus, cockroaches (Blattaria Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis, flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya be~~iana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pi pi ens, Culex nigripalpus, Culex quinquefasciatus, Culex tar salts, Culiseta inornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Ly coria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus. ticks and parasitic mites (Parasitiform.es): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti and Dermanyssus gallinae, Actinedida (Prostigmata) und Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptes spp, Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Arilus critatus, Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp, Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.

[0576] Roundworms Nematoda:

[0577] Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae,) Trichuris spp., Capillaria spp, Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp, Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus., Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus , Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylus abstrusus, and Dioctophyma renale, Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi, Camallanida, e.g. Dracunculus medinensis (guinea worm) Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp. a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp, Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp, Planarians (Plathelminthes): Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria a lata, Paragonimus spp., and Nanocyetes spp, Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp.

[0578] The compounds of formula (I) and compositions containing them are particularly useful for the control of pests from the orders Diptera, Siphonaptera and Ixodida.

[0579] In one embodiment, the present invention provides use of the compounds of formula (I) and compositions containing them for combating mosquitoes.

[0580] In one embodiment, the present invention provides use of the compounds of formula (I) and compositions containing them for combating flies.

[0581] In one embodiment, the present invention provides use of the compounds of of formula (I) and compositions containing them for combating fleas.

[0582] The use of the compounds of the present invention and compositions containing them for combating ticks is still another embodiment of the present invention.

[0583] The compounds of the present invention are also especially useful for combating endoparasites (roundworms nematoda, thorny headed worms and planarians).

[0584] In one embodiment, the administration of the compounds of the present invention can be carried out both prophylactically and therapeutically.

[0585] In another embodiment, administration of the compounds of the present invention is carried out directly or in the form of suitable preparations, orally, topically / dermally or parenterally.

[0586] For oral administration to warm-blooded animals, compounds of the present invention may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the compounds of the present invention may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg / kg to 100 mg / kg of animal body weight per day of the compound of the present invention, preferably with 0.5 mg / kg to 100 mg / kg of animal body weight per day. Alternatively, the compounds of the present invention may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The compounds of the present invention may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds of the present invention may be formulated into an implant for subcutaneous administration. In addition, the compound of the present invention may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg / kg to 100 mg / kg of animal body weight per day of the compound of the present invention.

[0587] The compounds of the present invention may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the compound of the present invention. In addition, the compounds of the present invention may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.

[0588] Suitable preparations are: Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels; Emulsions and suspensions for oral or dermal administration; semi-solid preparations; Formulations in which the active compound is processed in an ointment base or in an oil-inwater or water-in-oil emulsion base; Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.

[0589] The compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further ingredients such as acids, bases, buffer salts, preservatives, and solubilizers.

[0590] The solutions are filtered and filled sterile.

[0591] Suitable solvents are physiologically tolerable solvents such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, / V-mcthyl yrrolidone, 2-pyrrolidone, and mixtures thereof.

[0592] The active compounds can optionally be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.

[0593] Suitable solubilizers are solvents which promote the dissolution of the active compound in the main solvent or prevent its precipitation. Examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester.

[0594] Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n- butanol.

[0595] Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the used concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary. Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.

[0596] Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.

[0597] Further suitable solvents are polypropylene glycol, phenyl ethanol, phenoxy ethanol, ester such as ethyl or butyl acetate, benzyl benzoate, ethers such as alkyleneglycol alkylether, e.g. dipropylenglycol monomethylether, ketons such as acetone, methylethylketone, aromatic hydrocarbons, vegetable and synthetic oils, N, A imethylformamide, dimethylacetamide, transcutol, solketal, propylencarbonate, and mixtures thereof.

[0598] It may be advantageous to add thickeners during preparation. Suitable thickeners are inorganic thickeners such as bentonites, colloidal silicic acid, aluminium monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates.

[0599] Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment-like consistency result. The thickeners employed are the thickeners given above.

[0600] Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically. Pour -on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added.

[0601] Suitable solvents which are for example, water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol mono-butyl ether, ketones such as acetone, methyl ethyl ketone, cyclic carbonates such as propylene carbonate, ethylene carbonate, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, n-alkylpyrrolidones such as methylpyrrolidone, n-butylpyrrolidone or noctylpyrrolidone, / V-mcthyl yrrolidone, 2-pyrrolidone, 2,2-dimethyl-4-oxy-methylene-l ,3-dioxolane or glycerol formal.

[0602] Suitable colorants are for example, all colorants permitted for use on animals and which can be dissolved or suspended.

[0603] Suitable absorption-promoting substances are for example, dimethyl sulfoxide, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and copolymers thereof with poly ethers, fatty acid esters, triglycerides or fatty alcohols.

[0604] Suitable antioxidants are for example, sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole or tocopherol.

[0605] Suitable light stabilizers are for example, novantisolic acid. Suitable adhesives are, for example, cellulose derivatives, starch derivatives, polyacrylates or natural polymers such as alginates, gelatin. Emulsions can be administered orally, dermally or as injections. Emulsions are either of the water-in- oil type or of the oil-in-water type.

[0606] They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances.

[0607] Suitable hydrophobic phases (oils) are for example, Liquid paraffins, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic / capric biglyceride, triglyceride mixture with vegetable fatty acids of the chain length C1-C12 or other specially selected natural fatty acids, partial glyceride mixtures of saturated or unsaturated fatty acids possibly also containing hydroxyl groups, monoand diglycerides of the Cs-do fatty acids, fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol perlargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length Cie-Cis, isopropyl myristate, isopropyl palmitate, caprylic / capric acid esters of saturated fatty alcohols of chain length C12- Cis, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters such as synthetic duck coccygeal gland fat, dibutyl phthalate, diisopropyl adipate, and ester mixtures related to the latter, fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol, and fatty acids such as oleic acid and mixtures thereof. Suitable hydrophilic phases are: water, alcohols such as propylene glycol, glycerol, sorbitol and mixtures thereof.

[0608] Suitable emulsifiers are for example, non-ionic surfactants, e.g. polyethoxylated castor oil, polyethoxylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether; ampholytic surfactants such as di-sodium N-lauryl-p- iminodipropionate or lecithin.

[0609] Suitable anionic surfactants are for example, sodium lauryl sulfate, fatty alcohol ether sulfates, mono / dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt; suitable cation-active surfactants are cetyltrimethylammonium chloride.

[0610] Suitable further auxiliaries are for example, substances which enhance the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes, colloidal silicic acid or mixtures of the substances mentioned.

[0611] Suspensions can be administered orally or topically / dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers. Liquid suspending agents are all homogeneous solvents and solvent mixtures.

[0612] Suitable wetting agents (dispersants) are the emulsifiers given above. Other auxiliaries which may be mentioned are those given above.

[0613] Semi-solid preparations can be administered orally or topically / dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.

[0614] For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.

[0615] Suitable excipients are all physiologically tolerable solid inert substances. Those used are inorganic and organic substances. Inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, hydrogencarbonates, aluminium oxides, titanium oxide, silicic acids, argillaceous earths, precipitated or colloidal silica, or phosphates. Organic substances are, for example, sugar, cellulose, foodstuffs and feeds such as milk powder, animal meal, grain meals and shreds, starches.

[0616] Suitable auxiliaries are preservatives, antioxidants, and / or colorants which have been mentioned above. Other suitable auxiliaries are lubricants and glidants such as magnesium stearate, stearic acid, talc, bentonites, disintegration-promoting substances such as starch or crosslinked polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyrrolidone, and dry binders such as microcrystalline cellulose.

[0617] In general, "parasiticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds / compositions used in the present invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like. The compositions which can be used in the present invention generally comprise from about 0.001 to 95% of the compound of the present invention.

[0618] Generally, it is favorable to apply the compounds of the present invention in total amounts of 0.5 mg / kg to 100 mg / kg per day, preferably 1 mg / kg to 50 mg / kg per day. Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 per cent by weight, preferably from 0.1 to 65 per cent by weight, more preferably from 1 to 50 per cent by weight, most preferably from 5 to 40 per cent by weight. Preparations are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 per cent by weight, preferably of 1 to 50 per cent by weight. Furthermore, the preparations comprise the compounds of the present invention against endoparasites in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 per cent by weight, very particularly preferably of 0.005 to 0.25 per cent by weight.

[0619] In one embodiment, the compositions comprising the compounds of the present invention are applied dermally / topically.

[0620] In another embodiment, the topical application is conducted in the form of compound-containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils. Generally, it is favorable to apply solid formulations which release compounds of the present invention in total amounts of 10 mg / kg to 300 mg / kg, preferably 20 mg / kg to 200 mg / kg, most preferably 25 mg / kg to 160 mg / kg body weight of the treated animal in the course of three weeks.

[0621] For the preparation of the shaped articles, thermoplastic and flexible plastics as well as elastomers and thermoplastic elastomers are used. Suitable plastics and elastomers are polyvinyl resins, polyurethane, polyacrylate, epoxy resins, cellulose, cellulose derivatives, polyamides and polyester which are sufficiently compatible with the compounds of the present invention. A detailed list of plastics and elastomers as well as preparation procedures for the shaped articles is given e.g. in WO 2003 / 086075.

[0622] Positive crop response:

[0623] The compounds of the present invention not only control insect and mite pests effectively but also show positive crop response such as plant growth enhancement effects like enhanced root growth, enhanced tolerant to drought, high salt, high temperature, chill, forst or light radiation, improved flowering, enhanced nutrient utilization (such as improved nitrogen assimilation), enhanced quality plant product, more number of productive tillers, enhanced resistan...

Claims

WE CLAIM:

1. A compound of formula (I)wherein,R1is C1-C6-alkyl;Y is selected from oxygen (O) or NRY;RYis selected from the group consisting of hydrogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2- Cralkynyl, Ci-C haloalkyl, C2-C4-haloalkenyl, C3-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C3- alkyl and -C(O)Rla;Rlais selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C3-Cs-cycloalkyl and C3-Cs-cycloalkyl-Ci-C3-alkyl;R2is C(=W)R7; wherein W is selected from oxygen (O) or sulfur (S);R7is selected from the group consisting of OR4and NR5R6;R2ais selected from the group consisting of halogen, cyano, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6- alkoxy, C1-C6-alkoxy-C3-C6-cycloalkyl, C1-C6-haloalkyl and C1-C6-haloalkoxy;R4is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl and C3-Cs-cycloalkyl;R5is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, OR5a, NR5cR5d, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-Cs-cycloalkyl, C3-Cs- cycloalkyl-C1-C6-alkyl, -C(O)OR5d, -Ci-C3-alkyl-C(O)OR5d, -Ci-C3-alkyl-C(O)N(R5d)2, 3- to 6- membered non aromatic heterocyclic ring, 3- to 6- membered non aromatic heterocyclic ring-C1-C6-alkyl, phenyl and phenyl -C1-C6-alkyl; wherein each group may optionally be substituted with one or more groups of R5b;R5ais selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- haloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, phenyl -C1-C6-alkyl, and 3- to 6- membered non aromatic heterocyclic ring; wherein said heterocyclic ring and phenyl-C1-C6-alkyl groups may optionally be substituted with one or more groups selected from C1-C6-alkyl, C1-C6-alkoxy or halogen;R5bis selected from the group consisting of halogen, cyano, oxo, hydroxy, C1-C6-alkyl, C1-C6- alkylthio, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, -C(O)O-Ci-C6-alkyl and C1-C6-alkoxy;R5Cis selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkcnyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkcnyl and CT-CVcycloalkyl;R5dis independently selected from the group consisting of hydrogen and Ci-CT-alkyl;R6is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkcnyl, C2-C6- alkynyl, C1-C6-alkoxy, C1-C6-haloalkyl, C2-C6-haloalkenyl and C3-C6-cycloalkyl; orR5and R6together with the nitrogen atom to which they are attached may form a 3 - to 6- membered non aromatic heterocyclic ring; wherein said heterocyclic ring optionally contains 1 or 2 heteroatoms independently selected from N, O or S(0)o -2; said heterocyclic ring is optionally substituted by one or more substituents independently selected from halogen, cyano, oxo, C1-C6-alkyl, C1-C6-alkoxy or C1-C6-haloalkyl; orNR5R6represents -N=S(O)RxRXa, wherein Rxand RXaare independently selected from the group consisting of cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl, benzyl and 3- to 6- membered non aromatic heterocyclic ring; wherein said phenyl and benzyl rings are may optionally be substituted by one or more groups selected from halogen or C1-C6-alkyl; orRxand RXatogether with the sulfur atom to which they are attached may form a 3 - to 6- membered non aromatic heterocyclic ring; wherein said heterocyclic ring optionally contains 1 or 2 heteroatoms independently selected from N, O or S(0)o -2; said heterocyclic ring is optionally substituted by one or more substituents independently selected from halogen, cyano, oxo, C1-C6-alkyl, C1-C6-alkoxy or C1-C6-haloalkyl;Q represents partially saturated or unsaturated 5- to 12-membered heterocyclic ring which is substituted by one or more groups of R3and optionally substituted by one group of R10;R3is selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6- haloalkoxy, -S(O)0-2Ci-C3-haloalkyl and -S(0)o iR8=NR9;R8is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- haloalkyl, C2-C6-haloalkenyl and C CVcycloalkyl;R9is selected from the group consisting of hydrogen, cyano, C i-CT-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C CVcycloalkyl and C(=O)R';R10is selected from hydrogen or C1-C6-alkyl; or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof.

2. The compound of formula (I) according to claim 1, represented by a compound of formula (IA),wherein, R1, Q, R2, R2aand Y are as defined in claim 1.

3. The compounds of formula (I) according to claim 1 or 2, wherein Q is selected from the groupwherein, # denotes the point of attachment to the pyrazolopyrimidine ring; R10is selected from hydrogen or Ci-CT-alkyl; "n" is an integer ranging from 1 to 2; and R3is as defined in claim 1.

4. The compound of formula (I) according to claim 1 or 2, wherein R1is C1-C3-alkyl.

5. The compound of formula (I) according to claim 1 or 2, wherein Y is O.

6. The compound of formula (I) according to claim 1 or 2, wherein Y is NRY.

7. The compound of formula (I) according to claim 1 or 2, wherein W is oxygen (O).

8. The compound of formula (I) according to claim 1 or 2, wherein R2is C(=O)OR4; wherein R4are as defined in claim 1.

9. The compound of formula (I) according to claim 1 or 2, wherein R2is C(=O)NR5R6; wherein R5and R6are as defined in claim 1.

10. The compound of formula (I) according to claim 1 or 2, whereinR1is C1-C3-alkyl;Y is selected from oxygen (O) or NRY;RYis selected from the group consisting of hydrogen, cyano, C1-C3-alkyl, C1-C3-haloalkyl, C2- C4-haloalkenyl, C3-C5-cycloalkyl, C3-C5-cycloalkyl-C1-C3-alkyl and -C(O)Rla;Rlais selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C3-C5-cycloalkyl and C3-C5-cycloalkyl-C1-C3-alkyl;R2is C(=W)R7; wherein W is oxygen (O);R7is selected from the group consisting of OR4and NR5R6;R2ais selected from the group consisting of halogen, cyano, Ci-C3-alkyl, C3-C6-cycloalkyl;R4is selected from hydrogen or C1-C4-alkyl;R5is selected from the group consisting of hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4- alkynyl, OR5a, NR5cR5d, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, - C(O)OR5d, Ci-C3-alkyl-C(O)OR5d, Ci-C3-alkyl-C(O)N(R5d)2, 4- to 6- membered non aromatic heterocyclic ring, 4- to 6- membered non aromatic heterocyclic ring-C1-C4-alkyl, phenyl and phenyl-C1-C4-alkyl; wherein each group may optionally be substituted with one or more groups of R5b;R5ais selected from the group consisting of C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4- haloalkyl, C3-C6-cycloalkyl-Ci-C3-alkyl, phenyl-Ci-C3-alkyl, and 5- to 6- membered non aromatic heterocyclic ring; wherein said heterocyclic ring ans phenyl-Ci-C3-alkyl groups may optionally be substituted with one or more groups selected from Ci-C3-alkyl, Ci-C3-alkoxy or halogen;R5bis selected from the group consisting of halogen, cyano, oxo, hydroxy, C1-C4-alkyl, C1-C4- alkylthio, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, -C(O)O-C1-C4-alkyl and C1-C4-alkoxy;R5cis selected from hydrogen or C1-C4-alkyl;R5dis independently selected from hydrogen or C1-C4-alkyl;R6is selected from the group consisting of hydrogen, Ci-C3-alkyl and Ci-C3-alkoxy; orR5and R6together with the nitrogen atom to which they are attached may form a 3 - to 6- membered non aromatic heterocyclic ring; wherein said heterocyclic ring optionally contains 1 or 2 heteroatoms independently selected from N, O or S(0)o -2; said heterocyclic ring is optionally substituted by one or more substituents independently selected from halogen, cyano, oxo, Ci-C3-alkyl, Ci-C3-alkoxy or Ci-C3-haloalkyl; orNR5R6represents -N=S(O)RxRXa, wherein Rxand RXaare independently selected from cyano, Ci-C3-alkyl, phenyl or benzyl; wherein said phenyl and benzyl rings are may optionally be substituted by one or more groups selected from halogen or Ci-C3-alkyl; orRxand RXatogether with the sulfur atom to which they are attached may form a 5- to 6-membered non aromatic heterocyclic ring; wherein said heterocyclic ring optionally contains 1 or 2 heteroatoms independently selected from N, O or S(0)o -2;s selected from the group consisting of QI a to Q Ip;wherein, # denotes the point of attachment to the pyrazolopyrimidine ring;R3is selected from halogen, C 1-C3-haloalkyl or C 1-C3-haloalkoxy;R10is Ci-C3-alkyl;"n" is an integer ranging from 1 to 2; or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof.

11. A composition comprising the compound of formula (I) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof according to claim 1 and at least one additional component selected from the group consisting of surfactants and auxiliaries.

12. The composition according to claim 11, wherein said composition additionally comprises at least one biological active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers or nutrients.

13. The composition according to claim 11, wherein said compound of formula (I) ranges from 0.1 % to 99 % by weight with respect to the total weight of the composition.

14. A combination comprising a biologically effective amount of the compound of formula (I) according to claim 1 and at least one additional biological active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers or nutrients.

15. A method for protecting crops from attack or infestation by insects and mite pests comprises contacting the crop with the compound of formula (I) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof according to claim 1, composition thereof according to claim 11, or combination thereof according to claim 14.

16. The method according to claim 15, wherein said method comprises applying effective dosages of compound of formula (I) in amounts ranging from 1 gai to 5000 gai per hectare in agricul tural or horticultural crops.

7. A method for the protection of seeds, plants and plant parts from soil insects and of the seedlings roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and / orafter pre-germination with the compound of formula (I) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof according to claim 1, composition thereof according to claim 11, or combination thereof according to claim 14.

18. Use of the compound of formula (I) or salts, stereoisomers, polymorphs, metal complexes or N- oxides thereof according to claim 1, composition thereof according to claim 11, or combination thereof according to claim 14, for combating insects and mite pests in agricultural crops, horticultural crops, household and vector control and parasites on animals.

19. A seed comprising a compound of formula (I) or salts, metal complexes, N-oxides, stereoisomers, polymorphs thereof according to claim 1, composition thereof according to claim 11 or combination thereof according to claim 14, wherein the amount of compound of formula (I) in said seed ranging from about 0.0001 % to about 1 % by weight.

20. A compound of formula (Z), (A) or (B):wherein, Q is selected from the group consisting of Qla to Qlp:R1, R2, R2a, R3, R10and n are as defined in claim 1, with the proviso that 2-(ethylthio)-3-(6-(2,2,3,3,3- pentafluoropropoxy)pyridazin-3-yl)pyrazolo[l,5-a]pyrimidin-7(4H)-one;2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[l,5-a]pyrimidin-7(4H)-one and 2-(ethylthio)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[l,5- a]pyrimidin-7(4H)-one are excluded from the definition of compound of formula (A) and 3-(ethylthio)- 4-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-lH-pyrazol-5-amine and 3-(ethylthio)-4-(3-methyl- 6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-lH-pyrazol-5-amine are excluded from the definition of compound of formula (B).

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