Fused heterocyclic compound and uses thereof

Abstract

The present invention provides fused heterocyclic compounds of formula (I), wherein, R1, R2, R2', R3, m, A1, A2 and Y 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 COMPOUND AND 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 to a process for the preparation thereof. The present invention further relates to the composition comprising these compounds, and to their use as pest control agents.

[0004] BACKGROUND OF THE INVENTION

[0005] The currently available modem insecticides and acaricides have to satisfy many requirements, for example, regarding the level of activity, long-lasting efficacy, broad insecticidal spectrum, as well as environmental and toxicological safety, additional beneficial effects, and the possible use thereof. Efforts have been made during the past decades to develop selective insecticides that act specifically on biochemical modes of action 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. Further, WO2021140122, W02022049141 and W02022049144 disclose isoindoline compounds having insecticidal activity.

[0007] However, there is a constant need for new pest control agents with 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 the 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, metal complexes, or N-oxides thereof, wherein, R1, R2, R2', R3, Ai, A2, m and Y are as defined in the detailed description.

[0012] The present invention also provides a process for preparing the compounds of formula (I), or salts, stereoisomers, metal complexes, polymorphs, metal complexes, or N-oxides thereof.

[0013] The present invention additionally provides a composition for controlling or preventing invertebrate pests comprising a biologically effective amount of compounds of formula (I), or salts, stereoisomers, metal complexes, polymorphs, metal complexes, or N-oxides thereof, and at least one additional component selected from the group consisting of surfactants and auxiliaries.

[0014] The composition also 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.

[0015] The present invention further provides a seed comprising compounds of formula (I), or salts, stereoisomers, metal complexes, polymorphs, or N-oxides, compositions or combinations thereof.

[0016] The present invention provides the use of compounds of formula (I), or 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.

[0017] 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 compositions or combinations thereof.

[0018] DETAILED DESCRIPTION OF THE INVENTION

[0019] DEFINITIONS: 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.

[0020] 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.

[0021] 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.

[0022] 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 .

[0023] 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).

[0024] 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.

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

[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 products, agroforestry 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" refer 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 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, retainers, tautomers, optical isomers, 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 alkylsufonylamino, includes straight-chain or branched C1 to C24 alkyl, preferably C1 to C15 alkyl, more preferably C1 to C10 alkyl, most preferably C1 to C6 alkyl. 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 1 -ethyl -2 -methylpropyl or the different isomers. If the alkyl is at the end of a composite substituent, as, for example, in alkylcycloalkyl, the part of the composite substituent at the start, for example, the cycloalkyl, may be mono- or polysubstituted identically or differently and independently by alkyl. The same also applies to composite substituents in which other radicals, for example, alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy and the like, are at the end.

[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 C(, 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- 1-propenyl, 1 -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- 1-butenyl, 1 -methyl -2 -butenyl, 2-methyl-2-butenyl, 3 -methyl -2 -butenyl, 1-methyl- 3 -butenyl, 2-methyl-3 -butenyl, 3 -methyl-3 -butenyl, 1,1 -dimethyl -2 -propenyl, 1,2-dimethyl-l- propenyl, l,2-dimethyl-2 -propenyl, 1 -ethyl- 1-propenyl, 1 -ethyl -2 -propenyl, 1 -hexenyl, 2-hexenyl, 3- hexenyl, 4-hexenyl, 5-hexenyl, 1 -methyl- 1-pentenyl, 2-methyl- 1-pentenyl, 3 -methyl- 1-pentenyl, 4- methyl- 1-pentenyl, 1 -methyl -2 -pentenyl, 2-methyl-2-pentenyl, 3 -methyl -2 -pentenyl, 4-methyl-2- pentenyl, 1 -methyl-3 -pentenyl, 2-methyl-3-pentenyl, 3 -methyl-3 -pentenyl, 4-methyl-3 -pentenyl, 1- methyl -4-pentenyl, 2-methyl -4-pentenyl, 3 -methyl -4-pentenyl, 4-methyl -4-pentenyl, 1,1 -dimethyl -2- butenyl, 1 , 1 -dimethyl-3 -butenyl, 1 ,2-dimethyl- 1 -butenyl, 1 ,2-dimethyl -2 -butenyl, 1.2-dimethyl-3- butenyl, 1.3 -dimethyl- 1 -butenyl, 1.3 -dimethyl -2 -butenyl, 1.3 -dimethyl-3 -butenyl, 2.2-dimethyl-3- butenyl, 2.3 -dimethyl- 1 -butenyl, 2.3 -dimethyl -2 -butenyl, 2.3 -dimethyl-3 -butenyl, 3.3-dimethyl-l- 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- 1 -methyl -2- propenyl, 1 -ethyl -2 -methyl- 1-propenyl and 1 -ethyl -2 -methyl -2-propenyl and the different isomers, "Alkenyl' also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl as a part of a composite substituent, for example, haloalkenyl and the like, unless defined specifically elsewhere.

[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, 1 -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, 1,1 -dimethyl -2 -propynyl, 1- ethyl -2 -propynyl, 1 -hexynyl, 2-hexynyl, 3 -hexynyl, 4-hexynyl, 5 -hexynyl, 1 -methyl -2 -pentynyl, 1- methyl-3 -pentynyl, 1 -methyl -4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-l- pentynyl, 3 -methyl -4-pentynyl, 4-methyl- 1-pentynyl, 4-methyl-2 -pentynyl, 1,1 -dimethyl -2 -butynyl, l,l-dimethyl-3 -butynyl, l,2-dimethyl-3 -butynyl, 2,2-dimethyl-3-butynyl, 3, 3 -dimethyl- 1 -butynyl, 1- ethyl -2 -butynyl, l-ethyl-3 -butynyl, 2-ethyl-3 -butynyl and 1 -ethyl- 1 -methyl -2 -propynyl and the different isomers. This definition also applies to alkynyl as a part of a composite substituent, for example, haloalkynyl etc., unless specifically defined elsewhere. The term "alkynyl" can also include moieties comprised of multiple triple bonds, such as 2,5 -hexadiynyl.

[0034] 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.

[0035] 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. Non-limiting examples include “C3-C6- cycloalkyl-C1-C6-alkyl” which refers to a group consisting of a C3-C6-cycloalkyl ring bonded to a C1- C3, linear or branched alkyl chain. The cycloalkyl ring contains 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

[0036] The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Non-limiting examples of "haloalkyl" include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,

[0037] 2.2.2-trifluoroethyl, 2-chloro-2 -fluoroethyl, 2-chloro-2,2-difluoroethyl, 2, 2-dichloro-2 -fluoroethyl,

[0038] 2.2.2-trichloroethyl, pentafluoroethyl, l,l-dichloro-2,2,2-trifluoroethyl, and 1,1,1 -trifluoroprop-2 -yl. This definition also applies to haloalkyl as a part of a composite substituent, for example, haloalkylaminoalkyl etc., unless specifically defined elsewhere.

[0039] 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.

[0040] The term "haloalkoxy" means straight-chain or branched alkoxy groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non -limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1 -chloroethoxy, 1 -bromoethoxy, 1 -fluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2- dichloro-2 -fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1 -trifluoroprop-2 -oxy. This definition also applies to haloalkoxy as a part of a composite substituent, for example, haloalkoxyalkyl etc., unless specifically defined elsewhere.

[0041] The term "haloalkylthio" means straight-chain or branched alkylthio groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non -limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1 -chloroethylthio, 1- bromoethylthio, 1- fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2- chloro-2- fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2- trichloroethylthio, pentafluoroethylthio and 1,1,1 -trifluoroprop-2 -ylthio. This definition also applies to haloalkylthio as a part of a composite substituent, for example, haloalkylthioalkyl etc., unless specifically defined elsewhere.

[0042] Non-limiting examples of "haloalkylsulfinyl" include CF3S(O), CC13S(O), CF.CTbSiO) and CF3CF2S(O). Examples of "haloalkylsulfonyl" include CF3S(O)2, CC13S(O)2, CF3CH2S(O)2and CF3CF2S(O)2.

[0043] The term "hydroxy" means -OH, "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)-, "sulfinyl" means SO and "sulfonyl" means S(O)2.

[0044] The term “oxo” means a =0 group, “cyano” means -CN and the term “C1-C6-cyanoalkyl” refers to a C1-C6alkyl radical as generally defined above substituted with one or more cyano groups.

[0045] The term "alkoxy" used either alone or in compound words includes C1 to CM alkoxy, preferably C1 to C15 alkoxy, more preferably C1 to C1o alkoxy, most preferably C1 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 1 -ethyl -2- methylpropoxy and the different isomers. This definition also applies to alkoxy as part of a composite substituent, for example, haloalkoxy, alkynylalkoxy, etc., unless specifically defined elsewhere.

[0046] The term "alkoxyalkyl" or “C1-C3-alkoxy-C1-C3-alkyl” denotes an alkoxy substitution on alkyl. Nonlimiting examples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2and CH3CH2OCH2CH2. 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,

[0047] 1.2-dimethylbutylthio, 1,3 -dimethylbutylthio, 2,2-dimethylbutylthio, 2,3 -dimethylbutylthio, 3,3- dimethylbutylthio, 1 -ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2- trimethylpropylthio, 1 -ethyl- 1 -methylpropylthio and 1 -ethyl -2 -methylpropylthio and the different isomers.

[0048] Halocycloalkyl, halocycloalkenyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl, alkylsulfmylalkyl, alkylsulfonylalkyl, haloalkylcarbonyl, cycloalkylcarbonyl, haloalkoxylalkyl, and the like, are defined analogously to the above examples.

[0049] The terms alkoxyalkoxyalkyl, alkylaminoalkyl, dialkylaminoalkyl, cycloalkylaminoalkyl, cycloalkylaminocarbonyl and the like, are defined analogously to "alkylthioalkyl" or cycloalkylalkylamino .

[0050] The term "alkoxy carbonyl" is an alkoxy group bonded to a skeleton via a carbonyl group (-CO-). This definition also applies to alkoxy carbonyl as a part of a composite substituent, for example, cycloalkylalkoxy carbonyl and the like, unless specifically defined elsewhere.

[0051] The term C1-C6alkylsulfonyl denotes a radical -S(O)2R in which R is a C1-C6alkyl radical as generally defined above.

[0052] 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,

[0053] 1.2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3- dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1 -ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2- trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1 -ethyl- 1 -methylpropylsulfonyl and 1 -ethyl -2- methylpropylsulfonyl and the different isomers. The term "arylsulfonyl" includes Ar-S(O)2, wherein Ar can be any carbocycle or heterocylcle. This definition also applies to alkylsulfonyl as a part of a composite substituent, for example, alkylsulfonylalkyl etc., unless defined elsewhere.

[0054] "Alkylamino", "dialkylamino", and the like, are defined analogously to the above examples. The term ‘"optionally substituted” as used herein means that the group referenced is either unsubstituted or is substituted by a designated substituent. For example, “CrC+cycloalkyl is optionally substituted with 1 or 2 halo atoms” means C3-Chcycloalkyl, C3-Chcycloalkyl substituted with 1 halo atom and (>,- C4cycloalkyl substituted with 2 halo atoms. The term '‘optionally substituted” can be used interchangeably with “unsubstituted or substituted”.

[0055] As used herein, the term “phenyl” refers to a monocyclic aromatic ring of six carbon atoms with alternating double bonds (benzene ring), and said phenyl ring may be optionally substituted.

[0056] As used herein, the term “phenyl-C1-C6-alkyl” refers to a substituent in which a phenyl ring is bonded to a C1-C6linear or branched alkyl group. The alkyl chain contains 1 to 6 carbon atoms and may include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, or hexyl. Nonlimiting examples of phenyl-C1-C6-alkyl include benzyl, phenylethyl, phenylpropyl, etc.

[0057] The term "carbocycle" includes "aromatic carbocyclic ring systems" and "nonaromatic carbocyclic ring systems" or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which the ring may be aromatic or non-aromatic (where aromatic indicates that the Huckel rule is satisfied and nonaromatic indicates that the Huckel rule is not satisfied).

[0058] 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.

[0059] The term "aromatic" indicates that the Huckel rule is satisfied and the term "non-aromatic" indicates that the Huckel rule is not satisfied.

[0060] The terms "heterocycle" or "heterocyclic" or "heterocyclic ring system" include an "aromatic heterocycle" or "heteroaryl bicyclic ring system" and "nonaromatic heterocycle ring or ring system" or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds in which the ring may be aromatic or non-aromatic, wherein the heterocycle ring contains at least one heteroatom selected from N, O, S(0)0-2, and or the C ring member of the heterocycle may be replaced by C(=O), C(=S), C(=CR*R*) and C=NR*, * indicates integers.

[0061] The terms "non-aromatic heterocycle" or "non-aromatic heterocyclic" means three- to fifteenmembered, preferably three- to twelve-membered, saturated or partially unsaturated heterocycles 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, 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,

[0062] 1.2.4-oxadiazolidin-3-yl, l,2,4-oxadiazolidin-5-yl, l,2,4-thiadiazolidin-3-yl, l,2,4-thiadiazolidin-5-yl,

[0063] 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,

[0064] 2.4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4- dihydrothien-3-yl, pyrrolinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2- isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4- isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3- isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2- isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-l-yl, 2,3-dihydropyrazol- 2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol- 1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol- 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,

[0065] 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-

[0066] 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.

[0067] The terms "heteroaryl" or "aromatic heterocyclic" means 5 or 6-membered, fully unsaturated monocyclic ring systems 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,

[0068] 1.3.4-thiadiazolyl, 1,3,4-triazolyl, tetrazolyl; nitrogen-bonded 5-membered heteroaryl containing one to four nitrogen atoms, or benzofused nitrogen -bonded 5 -membered heteroaryl containing one to three nitrogen atoms: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms as ring members and in which two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member may be bridged by a buta-1,3- diene-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- 1-yl and 1,3,4-triazol-l-yl.

[0069] 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, 1,3, 5 -triazin-2 -yl,

[0070] 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, 1 -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.

[0071] This definition also applies to heteroaryl as a part of a composite substituent, for example, heteroarylalkyl etc., unless specifically defined elsewhere.

[0072] 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. Non-limiting examples of "alkylcarbonyl" include C(O)CH3, C(O)CH2CH2CH3 and C(O)CH(CH3)2. Non-limiting examples of "alkoxycarbonyl" include CH3OC(=O), CH3CH2OC(=O), CH3CH2CH2OC(=O), (CH3)2CHOC(=O) and the different butoxy or pentoxycarbonyl isomers. Nonlimiting examples of "alkylaminocarbonyl" include CH3NHC(=O), CH3CH2NHC(=O), CH3CH2CH2NHC(=O), (CH3)2CHNHC(=O) and the different butylamino or pentylaminocarbonyl isomers. Non-limiting examples of "dialkylaminocarbonyl" include (CH3)2NC(=O), (CH3CH2)2NC(=O), CH3CH2(CH3)NC(=O), CH3CH2CH2(CH3)NC(=O) and (CH3)2CHN(CH3)C(=O). Non-limiting examples of "alkoxyalkylcarbonyl" include CH3OCH2C(=O), CFfiOCFFCFFC^O), CH3CH2OCH2C(=O), CH3CH2CH2CH2OCH2C(=O) and CH3CH2OCH2CH2C(=O). Non-limiting examples of "alkylthioalkylcarbonyl" include CH3SCH2C(=O), CFfiSCFFCFFC^O), CH3CH2SCH2C(=O), CH3CH2CH2CH2SCH2C(=O) and CH3CH2SCH2CH2C(=O). The term haloalkylsufonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkyl amino and the like are defined analogously.

[0073] The term "amide" means A-R'C=ONR"-B, wherein R' and R" indicate substituents and A and B indicate any group.

[0074] The term "thioamide" means A-R'C=SNR"-B, wherein R' and R" indicate substituents and A and B indicate any group.

[0075] The total number of carbon atoms in a substituent group is indicated by the "C1-Cj" prefix, where i and j are numbers from 1 to 21. For example, C1-C3alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH3OCH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2. In the above recitations, when compounds of formula (I) are 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.

[0076] 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 n in (R)nindicates an integer ranging from, for example, 0 to 4, then the number of substituents may be selected from the integers between 0 and 4 inclusively.

[0077] 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 unsubstituted.

[0078] 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 the ways in which the embodiments herein may be practiced and to further enable those skilled in the art to practice the embodiments herein. Accordingly, the examples should not be construed as limiting the scope of the embodiments herein.

[0079] The description of the specific embodiments will fully reveal the general nature of the embodiments herein so 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.

[0080] 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.

[0081] The numerical values mentioned in the description and the description / claims though might form a critical part of the present invention, any deviation from such numerical values shall still fall within the scope of the present invention if that deviation follows the same scientific principle as that of the present invention disclosed in the present invention. The inventive compounds of the present invention may, if appropriate, be present as mixtures of different possible isomeric forms, especially of stereoisomers, for example E and Z, threo and erythro, and also optical isomers, but if appropriate also of tautomers. Both the E and the Z isomers, and also the threo and erythro isomers, and the optical isomers, any desired mixtures of these isomers and the possible tautomeric forms are disclosed and claimed.

[0082] 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, a pest is an animal or plant detrimental to humans or human concerns, including crops, livestock, and forestry.

[0083] 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 the plant breeders' rights. For the present disclosure, the term "plant" includes a living organism of the kind exemplified by trees, shrubs, herbs, grasses, fems, and mosses, typically growing in a site, absorbing water and required substances through its roots, and synthesizing nutrients in its leaves by photosynthesis.

[0084] 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, com, 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.

[0085] Preferably, the plant for the purpose of the present invention includes but is not limited to: cereals, com, rice, soybean and other leguminous plants, fruits and fruit trees, pome fruits, grapes and vines, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oil rape seed, 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.

[0086] 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 include but are 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, axillary buds, meristems, nodes and internodes.

[0087] 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.

[0088] Application of the compounds of the present disclosure or the compounds of the present disclosure in a composition optionally comprising other compatible compounds to a plant or plant material or locus thereof includes application by a technique known to a person skilled in the art, which includes but is not limited to spraying, coating, dipping, fumigating, impregnating, injecting and dusting. The term "applied" means adhered to a plant or plant part either physically or chemically, including impregnation.

[0089] Accordingly, the present invention provides fused heterocyclic compounds of formula (I), wherein,

[0090] R1is C1-C6-alkyl;

[0091] Y is selected from O or NRY;

[0092] 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-C3-cycloalkyl, C3-C3-cycloalkyl-C1-C3-alkyl, and -C(O)Rla;

[0093] Rlais selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, Ci-C3-alkoxy-C 1-C3- alkyl-, C3-C5-cycloalkyl, and C3-C3-cycloalkyl-C1-C3-alkyl;

[0094] R2is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3- Cx-cycloalkyl. a 5- or 6-membered heteroaryl ring, phenyl, -C(=O)NR5R6, -C(=O)ORb, -C(=O)-C1-C6- alkyl and -NR7R8; wherein said 5- or 6-membered heteroaryl ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S, and wherein each group of R2is unsubstituted or substituted with one, two, three or four groups of R2a;

[0095] R2ais independently selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C3-cycloalkyl, -S(0)0-2-C1-C6-alkyl, -S(0)0-2-C1- C6-haloalkyl, OR4, and NRaRb;

[0096] Rais selected from the group consisting of C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C2- C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C4-cycloalkyl, and OR4;

[0097] Rbis selected from the group consisting of hydrogen and C1-C6-alkyl;

[0098] R2' is independently selected from the group consisting of halogen, cyano, C1-C6-alkyl, C3-C6- cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, and C1-C6-haloalkoxy;

[0099] R3is selected from the group consisting of halogen, C1-C3-haloalkyl, -OC1-C3-haloalkyl, and -S(0)0- 2C1-C3-haloalkyl;

[0100] Ai is selected from N, C, or CH; A2 is selected from N, C, or CH;

[0101] R4is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1- C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-alkoxy-C1-C6-alkyl, and C3-Cx-cycloalkyl:

[0102] R5is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, OR5a, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-Cx-cycloalkyl. C3-C3-cycloalkyl-C1-C6-alkyl, a 3- to 6- membered non-aromatic heterocyclic ring, a 5- or 6-membered heteroaryl ring, phenyl, and phenyl-C1- C6 -alkyl; wherein said 3- to 6-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, and 5- or 6-membered heteroaryl ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S, and wherein each group of R5is unsubstituted or substituted with one to three groups of R5b;

[0103] R5ais selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, benzyl, and a 3- to 6-membered non-aromatic heterocyclic ring; wherein said 3- to 6-membered non- aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(O)0-2;

[0104] R5bis independently selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6- haloalkyl, -S(0)0-2-C1-C6-alkyl, -S(0)0-2-C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;

[0105] R6is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1- C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-cyanoalkyl, Cj-C3,-alkoxy-Ci-C3 -alkyl-, C3-C6-cycloalkyl, and a 3- to 4-membered non-aromatic heterocyclic ring; wherein said 3- to 4-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, and wherein said 3- to 4-membered non-aromatic heterocyclic ring is unsubstituted or substituted with one or two groups of R5b; or

[0106] R5and R6together with the nitrogen atom to which they are attached may form a 3 - to 6-membered non-aromatic heterocyclic ring, which optionally contains additional 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, said heterocyclic ring is optionally substituted with one to three substituents independently selected from halogen, oxo, cyano, C1-C6-alkyl, C1-C6-alkoxy, or C1-C6-haloalkyl; or

[0107] NR5R6represents -N=S(O)(RX)2, wherein Rxis independently selected from the group consisting of cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, benzyl, and a 3- to 6-membered non-aromatic heterocyclic ring; wherein said 3- to 6-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2; R7is selected from the group consisting of hydrogen, C1-C6-alkyl, cyano, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-cyanoalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-alkoxy, C3-Cx-cycloalkyl. C3-C8- cycloalkyl-C1-C6-alkyl, a 3- to 6-membered non-aromatic heterocyclic ring, a 5- or 6-membered heteroaryl ring, 5- or 6-membered heteroaryl-C1-C3-alkyl, NR5R6, C1-C6-alkylsulfonyl, -C(O)R9, and C1-C3-alkyl-C(O)R9; wherein said 3- to 6-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2 and 5- or 6-membered heteroaryl ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S, and wherein each group of R7is unsubstituted or substituted with one to three groups of R7a;

[0108] R7ais independently selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6- alkoxy, -C(O)O-C1-C3-alkyl, and hydroxyl;

[0109] R8is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1- C6-haloalkyl, C2-C6-haloalkenyl, C3-C6-cycloalkyl, and -C(O)R9a; or

[0110] R7and R8together with the nitrogen atom to which they are attached may form a 3 - to 6-membered non-aromatic heterocyclic ring, which optionally contains additional 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, said heterocyclic ring is optionally substituted with one to three substituents independently selected from halogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, or C1- C6-haloalkyl; or

[0111] -NR7R8represents -N=S(O)(RXa)2, wherein RXais independently selected from the group consisting of cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, benzyl, and a 3- to 6-membered non-aromatic heterocyclic ring; wherein said 3- to 6-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2;

[0112] R9is selected from the group consisting of C1-C6-alkyl, C3C8-cycloalkyl. C2-C6-alkenyl, C2- C6-alkynyl, C1-C6haloalkyl, C2-C6-haloalkenyl, C i-C6-alkoxy-C1 -C3, -alkyl-, and C1-C6-alkoxy;

[0113] R9ais selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2- C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C 1-C6-alkoxy-c1 -C3, -alkyl-, and C1-C6-alkoxy; and m is an integer selected from 1 or 2; or salts, stereoisomers, polymorphs, metal complexes, or N-oxides thereof.

[0114] In one embodiment, the compounds of formula (I) are represented by the compounds of formula (1-1) or salts, stereoisomers, polymorphs, metal complexes, or N-oxides thereof; wherein, R1, R2, R2, R3, Ai, A2 and Y are as defined in the detailed description.

[0115] In another embodiment, the compounds of formula (I) or (1-1) are represented by the compounds of formula (I-1A), or salts, stereoisomers, polymorphs, metal complexes, or N-oxides thereof; wherein, R1, R2, R2, R3, Ai, A2 and Y are as defined in the detailed description.

[0116] In yet another embodiment, the compounds of formula (I) are represented by the compounds of formula (1-2) or salts, stereoisomers, polymorphs, metal complexes, or N-oxides thereof; wherein, R1, R2, R2', R3, m, Ai and A2 are as defined in the detailed description.

[0117] In yet another embodiment, the compounds of formula (I) or (1-2) are represented by the compounds of formula (I-2A), or salts, stereoisomers, polymorphs, metal complexes, or N-oxides thereof; wherein, R1, R2, R3, Ai and A2 are as defined in the detailed description.

[0118] In yet another embodiment, the compounds of formula (I) are represented by the compounds of formula (IB), or salts, stereoisomers, polymorphs, metal complexes, or N-oxides thereof; wherein, R1, R2, R2', R3, Ai, A2 and RYare as defined in the detailed description.

[0119] In yet another embodiment, the compounds of formula (I) or (IB) are represented by the compounds of formula (IB-1), or salts, stereoisomers, polymorphs, metal complexes, or N-oxides thereof; wherein, R1, R2, R3, Ai, A2 and RYare as defined in the detailed description. In yet another embodiment, the present invention provides the compounds of formula (Z) or salts thereof; wherein, R1, R2, R2, R3, Ai and A2 are as defined in the detailed description.

[0120] In yet another embodiment, the present invention provides the compounds of formula (I-w) or salts thereof; wherein, R1, R3, Ai and A2 are as defined in the detailed description.

[0121] In yet another embodiment, the present invention provides the compounds of formula (I-x), (I-y) or (I- z) or salts thereof; wherein, Boc represents group, and represents point of attachment to an atom, to which it is attached; R2and R2' are as defined in the detailed description.

[0122] In yet another embodiment, the compounds of formula (Z) and (I-w) to (I-z) are intermediates for preparing compounds of formula (I) of the present invention.

[0123] The following list provides definitions, including preferred definitions, for the substituents, Ai, A2, Y, RY, R1, R2, R2', R3, R4, R5, R6, R7, R8, R9, R9a, m, Rla, R2a, R2b, Ra, Rb, R5a, R5b, and R7awith reference to the compounds of formula (I) or (1-1) (1-1 A) or (1-2) or (I-2A) or (IB) or (IB-1) or (Z) or (I-w) to (I-z) 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.

[0124] In one embodiment of the present invention, R1is C1-C6-alkyl.

[0125] In another embodiment of the present invention, R1is C 1-C3 -alkyl.

[0126] In a preferred embodiment of the present invention, R1is C2-alkyl.

[0127] In a more preferred embodiment of the present invention, R1is ethyl.

[0128] In one embodiment of the present invention, Y is selected from O or NRY.

[0129] In another embodiment of the present invention, Y is selected from O or NRY, wherein 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-C3-cycloalkyl, C3-C3-cycloalkyl-C1-C3-alkyl, and -C(O)Rla. In yet another embodiment of the present invention, RYis selected from the group consisting of hydrogen, cyano, C1-C-ralkyl, C1-C4-haloalkyl, C3-C3-cycloalkyl, C3-C3-cycloalkyl-C1-C3-alkyl, and - C(O)Rla.

[0130] In a preferred embodiment of the present invention, RYis selected from the group consisting of hydrogen, cyano, Ci-C’, -alkyl. Ci-CYhaloalkyl. C3-C3-cycloalkyl, C3-C3-cycloalkyl-C1-C3-alkyl, and - C(O)Rla.

[0131] In another preferred embodiment of the present invention, RYis selected from the group consisting of hydrogen, cyano, Ci-C\-alkyl. Ci-CYhaloalkyl. C3-C3-cycloalkyl, and -C(O)Rla.

[0132] In a preferred embodiment of the present invention, Y is O.

[0133] In another preferred embodiment of the present invention, Y is NRY.

[0134] In one embodiment of the present invention, Rlais selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C3-alkoxy-C1-C3-alkyl-, C3-C5-cycloalkyl, and C3-C3-cycloalkyl-C1-C3-alkyl.

[0135] In a preferred embodiment of the present invention, Rlais selected from the group consisting of C1-C3- alkyl, C1-C3-haloalkyl, C1-C3-alkoxy-C1-C3-alkyl-, CYC3-cycloalkyl. and C3-C3-cycloalkyl-C1-C3- alkyl.

[0136] In another preferred embodiment of the present invention, Rlais selected from the group consisting of C1-C3-alkyl, C1-C3-haloalkyl, C1-C3-alkoxy-C1-C3-alkyl-, and CYC's -cycloalkyl.

[0137] In a more preferred embodiment of the present invention, Rlais selected from the group consisting of C1-C3-alkyl, C1-C3-haloalkyl, and CYC3-cycloalkyl.

[0138] In one embodiment of the present invention, R2is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, CYCx-cycloalkyl. a 5- or 6-membered heteroaryl ring, phenyl, -C(=O)NR5R6, -C(=O)ORb, -C(=O)-C1-C6-alkyl and -NR7R8; wherein said 5- or 6-membered heteroaryl ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S, and wherein each group of R2is unsubstituted or substituted with one, two, three or four groups of R2a.

[0139] In another embodiment of the present invention, R2is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, CYC, -cycloalkyl. a 5- or 6-membered heteroaryl ring, phenyl, -C(=O)NR5R6, -C(=O)ORb, -C(=O)-C1-C3-alkyl and -NR7R8; wherein said 5- or 6-membered heteroaryl ring contains 1 or 2 heteroatoms, each independently selected from N, O or S, and wherein each group of R2is unsubstituted or substituted with one or two groups of R2a.

[0140] In yet another embodiment of the present invention, R2is selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, CYCYcycloalkyl. a 5- or 6-membered heteroaryl ring, phenyl, -C(=O)NR5R6, -C(=O)ORb, -C(=O)-C1-C3-alkyl and -NR7R8; wherein said 5- or 6-membered heteroaryl ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S, and wherein each group of R2is unsubstituted or substituted with one or two groups of R2a.

[0141] In a preferred embodiment of the present invention, R2is C1-C6-alkyl, preferably C 1-C3 -alkyl; wherein said group is unsubstituted or substituted with one or two groups of R2a.

[0142] In another preferred embodiment of the present invention, R2is C1-C6-haloalkyl, preferably C1-C3- haloalkyl; wherein said group is unsubstituted or substituted with one or two groups of R2a.

[0143] In yet another preferred embodiment of the present invention, R2is C3-Cx-cycloalkyl: preferably cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; more preferably cyclopropyl.

[0144] In yet another preferred embodiment of the present invention, R2is a 5- or 6-membered heteroaryl ring selected from pyrazolyl, thienyl, imidazolyl, triazolyl, pyridinyl, pyrimidinyl, pyridazinyl, or pyrazinyl; preferably thienyl, pyrazolyl, A'-mcthylpyrazolyl. pyridinyl, pyrimidinyl; wherein said 5- or 6-membered heteroaryl ring is unsubstituted or substituted with one or two groups of R2a.

[0145] In yet another preferred embodiment of the present invention, R2is phenyl; wherein said phenyl is unsubstituted or substituted with one or two groups of R2a.

[0146] In yet another preferred embodiment of the present invention, R2is -C(=O)NR5R6; wherein said group is unsubstituted or substituted with one or two groups of R2a.

[0147] In yet another preferred embodiment of the present invention, R2is -C(=O)ORb; wherein said group is unsubstituted or substituted with one or two groups of R2a.

[0148] In yet another preferred embodiment of the present invention, R2is -NR7R8; wherein said group is unsubstituted or substituted with one or two groups of R2a.

[0149] In yet another preferred embodiment of the present invention, R2is -C(=O)-C1-C3-alkyl; wherein said group is unsubstituted or substituted with one or two groups of R2a.

[0150] In one embodiment of the present invention, R2ais independently selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-Cx-cycloalkyl. -S(0)0- 2-C1-C3-alkyl, -S(0)0-2-C1-C3-haloalkyl, OR4, and NRaRb.

[0151] In yet another embodiment of the present invention, R2ais independently selected from the group consisting of halogen, cyano, C1-C3-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C3-haloalkyl, C3-C6- cycloalkyl, OR4, and NRaRb.

[0152] In a preferred embodiment of the present invention, R2ais independently selected from the group consisting of halogen, cyano, C1-C3-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C3-haloalkyl, C3-C6- cycloalkyl and OR4wherein R4is selected from C1-C3-alkyl or C1-C3-haloalkyl.

[0153] In a more preferred embodiment of the present invention, R2ais independently selected from the group consisting of halogen, cyano, C1-C3-alkyl, C1-C3-haloalkyl, C3-C6-cycloalkyl and OR4. In one embodiment of the present invention, Rais selected from the group consisting of C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-Cu-cycloalkyl. and OR4.

[0154] In another embodiment of the present invention, Rais selected from the group consisting of C 1 -C3 -alkyl, C1-C3-alkoxy-C1-C3-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C3-haloalkyl, C3-C4-cycloalkyl, and OR4.

[0155] In one embodiment of the present invention, Rbis selected from the group consisting of hydrogen, and C1-C6-alkyl.

[0156] In another embodiment of the present invention, Rbis selected from the group consisting of hydrogen, and C1-C4-alkyl.

[0157] In one embodiment of the present invention, R2' is independently selected from the group consisting of halogen, cyano, C1-C6-alkyl, C3-C6, -cycloalkyl. C1-C6-alkoxy, C1-C6-haloalkyl, and C1-C6-haloalkoxy.

[0158] In another embodiment of the present invention, R2' is independently selected from the group consisting of halogen, cyano, C1-C3-alkyl, C3-C3-cycloalkyl. C1-C3-alkoxy, C1-C6-haloalkyl, and C1-C6- haloalkoxy.

[0159] In a preferred embodiment of the present invention, R2' is C1-C4-alkyl.

[0160] In another preferred embodiment of the present invention, R2' is C1-C2-alkyl.

[0161] In a more preferred embodiment of the present invention, R2' is methyl.

[0162] In one embodiment of the present invention, R3is selected from the group consisting of halogen, C1- C3-haloalkyl, -OC1-C3-haloalkyl, and -S(0)0-2C1-C3-haloalkyl.

[0163] In another embodiment of the present invention, R3is selected from the group consisting of halogen, C1-C3-haloalkyl, and -OC1-C3-haloalkyl.

[0164] In a preferred embodiment of the present invention, R3is C1-C3-haloalkyl.

[0165] In a more preferred embodiment of the present invention, R3is trifluoromethyl.

[0166] In one embodiment of the present invention, R4is selected from the group consisting of hydrogen, C1- C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-alkoxy-C1-C6-alkyl, and C3-C3-cycloalkyl.

[0167] In another embodiment of the present invention, R4is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, and C3-C6- cycloalkyl.

[0168] In yet another embodiment of the present invention, R4is selected from the group consisting of hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, and C3-C5-cycloalkyl. In a preferred embodiment of the present invention, R4is selected from the group consisting of hydrogen, C1-C3-alkyl, C1-C3-haloalkyl, and C3-C6-cycloalkyl.

[0169] In one embodiment of the present invention, OR4is selected from the group consisting of -OH, -OC1- C6-alkyl, -OC2-C6-alkenyl, -OC2-C6-alkynyl, -OC1-C6-haloalkyl, -OC1-C6-alkoxy-C1-C6-alkyl, and - OC3-C6-cycloalkyl.

[0170] In another embodiment of the present invention, OR4is selected from the group consisting of -OH, - OC1-C3-alkyl, -OC2-C4-alkenyl, -OC2-C4-alkynyl, -OC1-C3-haloalkyl, -OC1-C3-alkoxy-C1-C3-alkyl, and -OC3-C6-cycloalkyl.

[0171] In one embodiment of the present invention, R5is selected from the group consisting of hydrogen, C1- C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, OR5a, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-Cx-cycloalkyl. C3-C3-cycloalkyl-C1-C6-alkyl, a 3- to 6-membered non-aromatic heterocyclic ring, phenyl, and phenyl- C1-C6-alkyl; wherein said 3- to 6-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, and wherein each group of R5is unsubstituted or substituted with one to three groups of R5b.

[0172] In another embodiment of the present invention, R5is selected from the group consisting of hydrogen, C1-C3-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, OR5a, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8- cycloalkyl, C3-Cx-cycloalkyl-C i-C6-alkyl, a 3- to 6-membered non- aromatic heterocyclic ring, phenyl, and phenyl-C1-C6-alkyl; wherein said 3- to 6-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, and wherein each group of R5is unsubstituted or substituted with one or two groups of R5b.

[0173] In yet another embodiment of the present invention, R5is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, OR5a, C1-C6-haloalkyl, C\-C(, -cycloalkyl. C3-C6- cycloalkyl-C1-C3-alkyl and a 3- to 4-membered non-aromatic heterocyclic ring; wherein said 3- to 4- membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, and wherein each group of R5is unsubstituted or substituted with one to three groups of R5b.

[0174] In a preferred embodiment of the present invention, R5is selected from the group consisting of hydrogen, C1-C3-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, OR5a, C1-C4-haloalkyl, C\-C(, -cycloalkyl. C3-C6- cycloalkyl-C1-C3-alkyl, a 3- to 5-membered non-aromatic heterocyclic ring and phenyl; wherein said 3- to 5-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, and wherein each group of R5is unsubstituted or substituted with one or two groups of R5b.

[0175] In a preferred embodiment of the present invention, R5is selected from the group consisting of hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, OR5a, C1-C4-haloalkyl, C\-C(, -cycloalkyl. C3-C6- cycloalkyl-C1-C3-alkyl, a 3- to 5-membered non-aromatic heterocyclic ring and phenyl; wherein said 3- to 5 -membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, and wherein each group of R5is unsubstituted or substituted with one or two groups of R5b.

[0176] In another preferred embodiment of the present invention, R5is selected from the group consisting of hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, OR5a, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6- cycloalkyl-C1-C3-alkyl, a 3- to 4-membered non-aromatic heterocyclic ring and phenyl; wherein said 3- to 4-membered non-aromatic heterocyclic ring contains 1 or 2 heteroatoms, each independently selected from N, O or S, and wherein each group of R5is unsubstituted or substituted with one or two groups of R5b.

[0177] In one embodiment of the present invention, R5ais selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, benzyl, and a 3- to 6-membered non-aromatic heterocyclic ring; wherein said 3- to 6-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2.

[0178] In another embodiment of the present invention, R5ais selected from the group consisting of C1-C4- alkyl, C2-C4 -alkenyl, C2-C4-alkynyl, benzyl, and a 3- to 5 -membered non-aromatic heterocyclic ring wherein said 3- to 6-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2.

[0179] In a preferred embodiment of the present invention, R5ais selected from the group consisting of C1-C4- alkyl, C2-C4-alkenyl, and C2-C4-alkynyl.

[0180] In another preferred embodiment of the present invention, R5ais selected from the group consisting of C1-C4-alkyl and C2-C4 -alkenyl.

[0181] In one embodiment of the present invention, -OR5ais selected from the group consisting of -OC1-C6- alkyl, -OC2-C6-alkenyl, -OC2-C6-alkynyl, -Obenzyl, and -O-(3- to 6-membered non-aromatic heterocyclic ring); wherein said 3- to 6-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2.

[0182] In another embodiment of the present invention, -OR5ais selected from the group consisting of -OC1- C4-alkyl, -OC2-C4-alkenyl, and -OC2-C4-alkynyl.

[0183] In one embodiment of the present invention, R5bis selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy.

[0184] In another embodiment of the present invention, R5bis selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, -S(0)0-2-C1-C4-alkyl, -S(0)0-2-C1-C4-haloalkyl, and C1-C4-alkoxy. In yet another embodiment of the present invention, R5bis independently selected from the group consisting of halogen, cyano, C1-C3-alkyl, C1-C3-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy.

[0185] In yet another embodiment of the present invention, R5bis independently selected from the group consisting of halogen, cyano, C1-C3-alkyl, Ci-C\-haloalkyl. C1-C4-alkoxy and C1-C4-haloalkoxy.

[0186] In one embodiment of the present invention, R6is selected from the group consisting of hydrogen, C1- C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-cyanoalkyl, C1-C6- alkoxy-C i-C’, -alkyl. C\-C(, -cycloalkyl. and a 3- to 4-membered non-aromatic heterocyclic ring; wherein said 3- to 4-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, and wherein said 3- to 4-membered non-aromatic heterocyclic ring is unsubstituted or substituted with one or two group of R5b.

[0187] In another embodiment of the present invention, R6is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C1-C3-alkoxy-C1-C3- alkyl, C3-C6-cycloalkyl, and a 3- to 4-membered non-aromatic heterocyclic ring; wherein said 3- to 4- membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, and wherein said 3- to 4-membered non-aromatic heterocyclic ring is unsubstituted or substituted with one or two groups of R5b, wherein R5bis independently selected from halogen, cyano, Ci-C\-alkyl. Ci-C\-haloalkyl. C 1-C3 -alkoxy or C1-C3-haloalkoxy.

[0188] In yet another embodiment of the present invention, R6is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C1-C3- alkoxy-C1-C3-alkyl, -cycloalky I. and a 3- to 4-membered non-aromatic heterocyclic ring; wherein said 3- to 4-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, and wherein said 3- to 4-membered non-aromatic heterocyclic ring is unsubstituted or substituted with one or two substituents independently selected from halogen, cyano, C1-C3-alkyl, C1-C3-haloalkyl, C1-C3-alkoxy or C1-C3-haloalkoxy.

[0189] In a preferred embodiment of the present invention, R6is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C6- cycloalkyl, and a 3- to 4-membered non-aromatic heterocyclic ring; wherein said 3- to 4-membered non-aromatic heterocyclic ring is unsubstituted or substituted with one or two substituents independently selected from halogen, cyano, C1-C3-alkyl, C1-C3-haloalkyl, C1-C3-alkoxy or C1-C3- haloalkoxy.

[0190] In another preferred embodiment of the present invention, R6is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C1-C3-alkoxy-C1-C3-alkyl- and C3-C6- cycloalkyl. In one embodiment of the present invention, R5and R6together with the nitrogen atom to which they are attached may form a 3- to 6-membered non-aromatic heterocyclic ring, which optionally contains additional 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, said heterocyclic ring is optionally substituted with one to three substituents independently selected from halogen, oxo, cyano, C1-C3-alkyl, C1-C3-alkoxy, or Ci-C\-haloalkyl.

[0191] In another embodiment of the present invention, R5and R6together with the nitrogen atom to which they are attached may form a 3- to 5-membered non-aromatic heterocyclic ring, which optionally contains additional 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, said heterocyclic ring is optionally substituted with one to three substituents independently selected from halogen, cyano, Ci-C\-alkyl. C1-C3-alkoxy, or C1-C3-haloalkyl.

[0192] In one embodiment of the present invention, NR5R6represents -N=S(O)(RX)2, wherein Rxis independently selected from the group consisting of cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, benzyl, and a 3- to 6-membered heterocyclic ring; wherein said 3- to 6-membered non- aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2.

[0193] In another embodiment of the present invention, NR5R6represents -N=S(O)(RX)2, wherein Rxis independently selected from the group consisting of cyano, C1-C6-alkyl, and a 3- to 6-membered heterocyclic ring.

[0194] In a preferred embodiment of the present invention, NR5R6represents -N=S(O)(RX)2, wherein Rxis independently selected from C1-C6-alkyl.

[0195] In a more preferred embodiment of the present invention, NR5R6represents -N=S(O)(RX)2, wherein Rxis independently selected from C1-C-ralkyl.

[0196] In one embodiment of the present invention, R7is selected from the group consisting of hydrogen, C1- C6-alkyl, cyano, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-cyanoalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-alkoxy, C3-Cx-cycloalkyl. C-Cx-cycloalkyl-Ci-C6-alkyl. a 3- to 6-membered non- aromatic heterocyclic ring, a 5- or 6-membered heteroaryl ring, 5- or 6-membered heteroaryl-C1-C3-alkyl, NR5R6, C1-C6-alkylsulfonyl, -C(O)R9, and C1-C3-alkyl-C(O)R9; wherein said 3- to 6-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2 and 5- or 6-membered heteroaryl ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S, and wherein each group of R7is unsubstituted or substituted with one to three groups of R7a.

[0197] In another embodiment of the present invention, R7is selected from the group consisting of hydrogen, C1-C6-alkyl, cyano, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-cyanoalkyl, C1-C6-haloalkyl, C2-C6- haloalkenyl, C1-C6-alkoxy, C3-Cx-cycloalkyl. C-Cx-cycloalkyl-Ci-C6-alkyl. a 3- to 6-membered non- aromatic heterocyclic ring, C1-C6-alkylsulfonyl, and -C(O)R9; wherein said 3- to 6-membered non- aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2 and wherein each group of R7is unsubstituted or substituted with one to two groups of R7a.

[0198] In a preferred embodiment of the present invention, R7is selected from the group consisting of hydrogen, C1-C3-alkyl, cyano, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-cyanoalkyl, C1-C4-haloalkyl, C2- C6-haloalkenyl, C1-C4-alkoxy, C3-C6-cycloalkyl, C’.-C6-cycloalkyl-Ci-C’, -alkyl, and -C(O)R9; wherein each group of R7is unsubstituted or substituted with one to three groups of R7a.

[0199] In a preferred embodiment of the present invention, R7is selected from the group consisting of hydrogen, C1-C4-alkyl, cyano, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-cyanoalkyl, C1-C4-haloalkyl, C2- C6-haloalkenyl, C1-C4-alkoxy, C3-C6-cycloalkyl, C’.-C6-cycloalkyl-Ci-C’, -alkyl, and -C(O)R9; wherein each group of R7is unsubstituted or substituted with one to three groups of R7a.

[0200] In another preferred embodiment of the present invention, R7is selected from the group consisting of hydrogen, C1-C4-alkyl, cyano, C1-C4-cyanoalkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C3-C6-cycloalkyl, C3- C6-cycloalkyl-C1-C3-alkyl, and -C(O)R9; wherein each group of R7is unsubstituted or substituted with one to two groups of R7a.

[0201] In one embodiment of the present invention, R7ais independently selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, -C(O)O-C1-C3-alkyl, and hydroxyl.

[0202] In another embodiment of the present invention, R7ais independently selected from the group consisting of halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, -C(O)O-C1-C3-alkyl, and hydroxyl.

[0203] In yet another embodiment of the present invention, R7ais independently selected from the group consisting of halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy and hydroxyl.

[0204] In one embodiment of the present invention, R8is selected from the group consisting of hydrogen, C1- C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, -cycloalkyl. and - C(O)R9a.

[0205] In another embodiment of the present invention, R8is selected from the group consisting of hydrogen, C1-C3-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, and -C(O)R9a.

[0206] In yet another embodiment of the present invention, R8is selected from the group consisting of hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C3-C6- cycloalkyl, and -C(O)R9a.

[0207] In a preferred embodiment of the present invention, R8is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C\-C(, -cycloalkyl. and -C(O)R9a.

[0208] In one embodiment of the present invention, R7and R8together with the nitrogen atom to which they are attached may form a 3- to 6-membered non-aromatic heterocyclic ring, which optionally contains additional 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, said heterocyclic ring is optionally substituted with one to three substituents independently selected from halogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, or C1-C6-haloalkyl.

[0209] In one embodiment of the present invention, R7and R8together with the nitrogen atom to which they are attached may form a 3- to 5 -membered non-aromatic heterocyclic ring, which optionally contains additional 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, said heterocyclic ring is optionally substituted with one to three substituents independently selected from halogen, cyano, Ci-C\-alkyl. C1-C3-alkoxy, or Ci-C\-haloalkyl.

[0210] In one embodiment of the present invention, -NR7R8represents -N=S(O)(RXa)2, wherein RXais independently selected from the group consisting of cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, benzyl, and a 3- to 6-membered non-aromatic heterocyclic ring; wherein said 3- to 6- membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2.

[0211] In another embodiment of the present invention, -NR7R8represents -N=S(O)(RXa)2, wherein RXais independently selected from the group consisting of cyano, C1-C4-alkyl, C2-C4 -alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, benzyl, and a 3- to 6-membered non-aromatic heterocyclic ring; wherein said 3- to 6- membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2.

[0212] In a preferred embodiment of the present invention, -NR7R8represents -N=S(O)(RXa)2, wherein RXais independently selected from C1-C6-alkyl.

[0213] In a more preferred embodiment of the present invention, -NR7R8represents -N=S(O)(RXa)2, wherein RXais independently selected from C1-C4-alkyl.

[0214] In one embodiment of the present invention, R9is selected from the group consisting of C1-C6-alkyl, C3-Cx-cycloalkyl. C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-alkoxy-C1- C3-alkyl-, and C1-C6-alkoxy.

[0215] In another embodiment of the present invention, R9is selected from the group consisting of C1-C4-alkyl, C3-C3-cycloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C1-C3-alkoxy-C1- C3-alkyl-, and C1-C4-alkoxy.

[0216] In a preferred embodiment of the present invention, R9is selected from the group consisting of C1-C4- alkyl, C3-C6-cycloalkyl, C1-C4-haloalkyl, C1-C3-alkoxy-C1-C3-alkyl- and C1-C3-alkoxy.

[0217] In another preferred embodiment of the present invention, R9is selected from the group consisting of C1-C4-alkyl, C3-C3-cycloalkyl, C1-C4-haloalkyl, and C1-C3-alkoxy. In one embodiment of the present invention, R9ais selected from the group consisting of C1-C6-alkyl, C3-C3, -cycloalkyl. C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-alkoxy-C1- C’, -alkyl-. and C1-C6-alkoxy.

[0218] In another embodiment of the present invention, R9ais selected from the group consisting of C1-C4- alkyl, C3-C3-cycloalkyl. C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C1-C4- alkoxy-C3-C3-alkyl-. and C1-C4-alkoxy.

[0219] In yet another embodiment of the present invention, R9ais selected from the group consisting of C1-C4- alkyl, C3-C3-cycloalkyl, C1-C4-haloalkyl, and C1-C4-alkoxy.

[0220] In a preferred embodiment of the present invention, R9ais selected from the group consisting of C1-C3- alkyl and C3-C3-cycloalkyl.

[0221] In a more preferred embodiment of the present invention, R9ais C3-C5-cycloalkyl.

[0222] In one embodiment of the present invention, m is an integer selected from 1 or 2.

[0223] In a preferred embodiment of the present invention, m is 1.

[0224] In one embodiment of the present invention, Ai is selected from N, C, or CH.

[0225] In another embodiment of the present invention, Ai is N.

[0226] In yet another embodiment of the present invention, Ai is C.

[0227] In yet another embodiment of the present invention, Ai is CH.

[0228] In one embodiment of the present invention, A2 is selected from N, C, or CH.

[0229] In another embodiment of the present invention, A2 is N.

[0230] In yet another embodiment of the present invention, A2 is C.

[0231] In yet another embodiment of the present invention, A2 is CH.

[0232] In one embodiment of the present invention, Ai and A2 is C or CH.

[0233] In another embodiment of the present invention, one of Ai or A2 is nitrogen (N).

[0234] For the substituents defined herein above, any or more of the definitions provided above may be combined with any definition of any other substituent defined herein above. Such combinations include all variations within the scope of the definitions provided. For example, but not limited to, the present invention provides compounds of formula (I) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof, wherein R1is C 1-C3 -alkyl; Y is selected from O or NRY;

[0235] RYis selected from the group consisting of hydrogen, cyano, C1-C3-alkyl, C1-C3-haloalkyl, C3- C3-cycloalkyl, and -C(O)Rla; Rlais selected from the group consisting of C1-C3-alkyl, C’l-CAhaloalkyl. C1-C3- alkoxy-C1-C3-alkyl-, and C3-C3-cycloalkyl;

[0236] R2is selected from the group consisting of hydrogen, halogen, cyano, C1-C-ralkyl, C1-C4-haloalkyl, C3- C6-cycloalkyl, a 5- or 6-membered heteroaryl ring, phenyl, -C(=O)NR5R6, -C(=O)ORb, -C(=O)-C1-C3- alkyl and -NR7R8; wherein said 5- or 6-membered heteroaryl ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S, and wherein each group of R2is unsubstituted or substituted with one or two groups of R2a;

[0237] R2ais independently selected from the group consisting of halogen, cyano, C1-C3-alkyl, C1-C3- haloalkyl, C3-C6-cycloalkyl and OR4;

[0238] Rbis selected from the group consisting of hydrogen and C1-C-ralkyl;

[0239] R2is C1-C4-alkyl;

[0240] R3is C1-C3-haloalkyl;

[0241] Ai is selected from N, C, or CH;

[0242] A2 is selected from N, C, or CH;

[0243] R4is selected from the group consisting of hydrogen, C1-C3-alkyl, C1-C3-haloalkyl and C3-C6- cycloalkyl;

[0244] R5is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, OR5a, C1-C6-haloalkyl, C3-C6-cycloalkyl, O-C6-cycloalkyl-Ci-C’, -alkyl and a 3- to 4-membered non-aromatic heterocyclic ring; wherein said 3- to 4-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, and wherein each group of R5is unsubstituted or substituted with one to three groups of R5b;

[0245] R5ais selected from the group consisting of C1-C4-alkyl and C2-C4-alkenyl;

[0246] R5bis independently selected from the group consisting of halogen, cyano, C1-C3-alkyl, C1-C3- haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;

[0247] R6is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C1-C3-alkoxy-C1-C3-alkyl- and C3-C6-cycloalkyl; or

[0248] NR5R6represents -N=S(O)(RX)2, wherein Rxis independently selected from C1-C6-alkyl;

[0249] R7is selected from the group consisting of hydrogen, C1-C4-alkyl, cyano, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-cyanoalkyl, C1-C4-haloalkyl, C2-C6-haloalkenyl, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6- cycloalkyl-C1-C3-alkyl, and -C(O)R9; wherein each group of R7is unsubstituted or substituted with one to three groups of R7a; R7ais independently selected from the group consisting of halogen, cyano, C1-C3-alkyl, C1-C3- alkoxy, and hydroxyl;

[0250] R8is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, and -C(O)R9a; or

[0251] -NR7R8represents -N=S(O)(RXa)2, wherein RXais independently selected from C1-C6-alkyl;

[0252] R9is selected from the group consisting of C1-C4-alkyl, C3-C6-cycloalkyl, C i-Ohaloalkyl. C1- C3-alkoxy-C1-C3-alkyl- and C1-C3-alkoxy;

[0253] R9ais selected from the group consisting of C1-C3-alkyl and C3-C5-cycloalkyl; and m is 1.

[0254] 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.

[0255] An anion part of the salt in case of the compounds of formula (I) is cationic or capable of forming a cation which can be inorganic or organic. Alternatively, a cation part of the salt, in case the compounds 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 an organic anion part of the salt include but are not limited to formate, alkanoates, carbonates, acetates, trifluoroacetate, trichloroacetate, propionate, glycolate, thiocyanate, lactate, succinate, malate, citrates, benzoates, cinnamates, oxalates, alkylsulphates, alkylsulphonates, arylsulphonates aryldisulphonates, alkylphosphonates, arylphosphonates, aryldiphosphonates, p-toluenesulphonate, and salicylate. Examples of an inorganic cation part of the salt include but are not limited to alkali and alkaline earth metals. Examples of an organic cation part of the salt include but are not limited to pyridine, methyl amine, imidazole, benzimidazole, hitidine, phosphazene, tetramethyl ammonium, tetrabutylammonium, choline and trimethylamine.

[0256] Metal ions in metal complexes of the compounds of formula (I) are especially the ions of the elements of the second main group, especially calcium and magnesium, of the third and fourth main group, especially aluminium, tin and lead, and also of the first to eighth transition groups, especially chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Particular preference is given to the metal ions of the elements of the fourth period and the first to eighth transition groups. Here, the metals can be present in the various valencies that they can assume.

[0257] In one embodiment, the present invention provides the compounds of formula (I), or salts, metal complexes, stereoisomers, or N-oxides thereof and its composition with an excipient, inert carrier or any other essential ingredient such as surfactants, additives, solid diluents and liquid diluents.

[0258] 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 compounds with an acid of the anion in question if the compounds of formula (I) have a basic functionality.

[0259] 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.

[0260] 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 that represent essentially a single crystal type and embodiments that 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 the compounds 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 compounds represented by formula (I). Preparation and isolation of a particular polymorph of the compounds 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.

[0261] In an embodiment, the present invention provides a process for preparing the compounds of formula (I), or salts, stereoisomers polymorphs, metal complexes, or N-oxides thereof.

[0262] The compounds of the present invention can be made as shown in the following schemes, in which, unless otherwise stated, the definition of each variable is as defined above for the compounds of formula (I). The compounds of formula (I) can be prepared according to schemes 1-12 and the chemistry examples described herein.

[0263] General synthetic schemes: wherein, R1, R2, R3Ai and A2 have the meanings as described above.

[0264] The compounds of formula (3) are either commercially available or can be prepared by using the methods known or analogously described in W02004089919, Bioorganic & Medicinal Chemistry Letters (2016), 26(10), 2526-2530 and WO2022049146.

[0265] Compounds of formula (4a / 4b) can be prepared by reacting an amine derivative of formula (2a / 2b) with a halide (preferably bromide) of formula (3), in the presence of a base such as sodium or potassium or cesium carbonate, N, A'-di isopropyl ethylamine, sodium hydride, sodium or potassium tert butoxide and in the presence of a suitable solvent such as tetrahydrofuran, acetonitrile, N, A'-dimcthylfonnamidc or DMSO (dimethyl sulfoxide). The reaction can be carried out at a temperature ranging from about 0 °C to 150 °C.

[0266] Deprotection of the ‘PG’ in compounds of formula (4a), can lead to an in-situ cyclization reaction to provide compounds of formula (Za). Protection groups such as -Boc will be deprotected under acidic conditions, for example, in the presence of acetic acid or trifluoroacetic acid or cone, hydrochloric acid, in the presence of a suitable solvent such as dichloromethane, tetrahydrofuran or dichloromethane, at a temperature in the range of 0 °C to 120 °C. Protection groups such as -Fmoc or -COCF3, will be deprotected under basic conditions such as treating them with sodium or potassium hydroxide, sodium or potassium carbonate or piperidine, in the presence of a suitable solvent such as methanol, ethanol, tetrahydrofuran, dioxane or water, at a temperature in the range of 0 °C to 120 °C. Such in situ cyclization through deprotection reactions is reported in the literature, for example in WO2014191929, US20050096323 and Journal of Organic Chemistry (2011), 76(11), 4582-4590.

[0267] Alternatively, compounds of formula (Za) can be prepared by reacting an amine of formula (2b) with halides (preferably bromide) of formula (3), in the presence of a base such as sodium or potassium or cesium carbonate, N, A'-di isopropyl ethylamine, sodium hydride, sodium or potassium tert butoxide, and in the presence of a suitable solvent such as tetrahydrofuran, acetonitrile, A'.A'-dimcthylfonnamidc. toluene or DMSO. The reaction is carried out at a temperature in the range of 0 °C to 150 °C. Such types of nucleophilic substitution and subsequent cyclization reactions are described previously in WO 2011087776 and WO 2011057022.

[0268] In another approach, subjecting the compounds of formula (4b) to ester hydrolysis conditions, in the presence of lithium or sodium or potassium hydroxide, in a suitable solvent such as methanol, ethanol, tetrahydrofuran, water or a mixture thereof, provides an acid of formula (5). The compounds of formula (Za) can be prepared by cyclizing compounds of formula (5) in the presence of POCE, SOCh or any other amide coupling reagent such as HATU, EDC.HC1 or T3P (Propanephosphonic acid anhydride), optionally in the presence of a base such as triethylamine, diisopropylamine or pyridine, in the presence of a suitable solvent such as dichloromethane, tetrahydrofuran, toluene, xylene or N,N- dimethylformamide, at a temperature in the range of 0 °C to 150 °C.

[0269] Scheme: 2 wherein, R1, R2, R3, Ai and A2 have the meanings as described above

[0270] Compounds of formula (6) can be prepared by treating halides (preferably chloride or bromide) of formula (3) with ammonia or an ammonia source, optionally in the presence of a suitable solvent such as ethanol, methanol, isopropanol or dioxane, at a temperature in the range of 25 °C to 100 °C. Such examples are reported in the literature, for example, in WO2021143927 and Bioorganic & Medicinal Chemistry Letters (2012), 22(2), 814-819.

[0271] Compounds of formula (Za) can be prepared by reacting the compounds of formula (6) with the compounds of formula (2c), in the presence of a base. Examples of the base include but is not limited to sodium, potassium or cesium carbonate, sodium or potassium tert-butylate, or diisopropylethylamine or triethylamine or DBU, or pyridine, in a solvent selected from tetrahydrofuran, A, N- dimethylformamide, acetonitrile and dimethyl sulfoxide, at a temperature in the range of 25 °C to 130

[0272] Alternatively, compounds of formula (Za) can be prepared by reacting compounds of formula (6) under transition metal-catalyzed conditions. The reaction may be catalyzed by a palladium -based catalyst, involving for example bis(dibenzylideneacetone)palladium(0) (Pd(dba)2), tris(dibenzylideneacetone)dipalladinm(0) (Pd2(dba)3); optionally in the form of its chloroform adduct) or palladium(II) acetate , and a ligand, for example XantPhos ((5-di-phenylphosphanyl-9,9-dimethyl- xanthen-4yl)diphenylphosphane), XPhos (2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl), RuPhos (2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl), BINAP (2,2’- bis(diphenylphosphino)-l,l’-binaphthalene), in the presence of a base, like sodium, potassium or cesium carbonate, or sodium, potassium tert-butylate, or potassium phosphate, in a solvent or a solvent mixture, like, for example dioxane, 1,2-dimethoxyethane or toluene, preferably under an inert atmosphere. The reaction temperature can preferentially range from 25 °C to the boiling point of the reaction mixture, or the reaction may be performed under microwave irradiation. Such reactions, and alternative conditions such as iron or copper catalysis, have been described, for example, in WO2018 / 099812.

[0273] Alternatively, compounds of formula (Za) can also be prepared by copper or nickel catalysis. Examples of the such catalysts to be used in the reaction include copper catalysts such as copper(I) iodide, copper(I) bromide, copper(I) chloride, copper(I) oxide, trifluromethanesulfonicacid copper(I)salt benzene complex, 2-thiophenecarboxylic acid copper(I)salt; and nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel chloride, and a ligand, for example, 1,10-phenanthroline, 8- hydroquinoline, trans- 1,2-cyclohexanediamine, trans- l,2-bis(methylamino)cyclohexane, N,N- dimethylethylenediamine, 2,2'-bipyridine, 2-aminoethanol, triphenyl phosphine, 1 ,2- bis(diphenylphosphino)ethane, l,3-bis(diphenylphosphino)propane, XantPhos ((5-di- phenylphosphanyl-9,9-dimethyl-xanthen-4yl)diphenylphosphane), XPhos (2-Dicyclohexylphosphino- 2',4',6'-triisopropylbiphenyl), RuPhos (2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl), BINAP (2, 2’-bis(diphenylphosphino)-l,l ’-binaphthalene), l,l’-bis(diphenylphosphino)ferrocene. Examples of the base include but are not limited to, alkali metal carbonates, diisopropylethylamine, pyridine, 1, 8- Diazabicyclo [5.4.0] undec-7-ene or 4 -(dimethylamino) pyridine, in an appropriate solvent such as acetonitrile, dimethyl sulfoxide (DMSO), A'.A'-dimcthylfonnamidc. A'.A'-dimcthylacctamidc or N- methyl-2 -pyrrolidone, at a temperature in the range of 25 °C to 120 °C.

[0274] Scheme: 3 wherein, R1and R2have the meanings as described above.

[0275] Carbamates of formula (2a) can be prepared by treating an acid of formula (2) under Curtins rearrangement conditions. This involves reacting an organoazide derived from an acid of formula (2), with suitable alcohol such as methanol, ethanol, tert butanol or Fmoc-OH, optionally in the presence of a base such as triethylamine or N, A-diisopropylamine or pyridine, in the presence of a suitable solvent such as toluene, xylene or 1,4-dioxane, at a temperature in the range of 60 °C to 150 °C. Organoazide compounds can be derived from an acid of formula (2), by reacting the acid with an azide source, preferably diphenylphosphoryl azide, or any other azides such as sodium azide, tosyl azide or trimethylsilyl azide, in the presence of a base such as triethylamine or N, A-diisopropylamine or pyridine, in the presence of a suitable solvent such as toluene, xylene or dioxane, at a temperature in the range of 0 °C to 25 °C. Typically the process will be performed in one pot or optionally in two separate steps.

[0276] Amine derivatives of formula (2b), can be obtained by deprotection of the carbamate of formula (2a) under either acidic or basic conditions based on the R’ group of the carbamate. Carbamates where R’ = tBu can be deprotected under acidic conditions such as acetic acid or trifluoroacetic acid or hydrochloric acid, in a suitable solvent, for example, dichloromethane, tetrahydrofuran or dichloromethane, at a temperature in the range of 0 °C to 120 °C. Carbamates where R’ = Me, Et or Fmoc groups can be deprotected under basic conditions such as sodium or potassium hydroxide, sodium or potassium carbonate or piperidine, in the presence of a suitable solvent such as methanol, ethanol, tetrahydrofuran, dioxane or water, at a temperature in the range of 0 °C to about 120 °C.

[0277] A conversion of amino-substituted compounds of formula (2b) to halo-substituted compounds (preferably bromide or iodide) of formula (2c) can be carried out under Sandmeyer reaction conditions, known to one skilled in the art, under reaction conditions such as, for example, the treatment of an amine with a diazonium reagent such as tert-butyl nitrite or isoamyl nitrite or NaNCE / HCI or a NaNCf / HBr mixture, followed by the addition of any halide source including but not limited to copper (I) bromide or chloride or iodide, potassium bromide or iodide, in the presence of a suitable solvent such as acetonitrile, tetrahydrofuran, 1,2-dichloroethane, A. A-dimcthylfonnamidc. water or a mixture thereof, at a temperature in the range of 0 °C to 100 °C. Alternatively, halo-substituted compounds of formula (2c) can be prepared from compounds of formula (2) through decarboxylative halogenation conditions, including but not limited to using a halogenating agent such as potassium or sodium bromide, potassium or sodium iodide, bromine, iodine, A-bromo succinamide or A-iodo succinamide, optionally in the presence of an additive such as AgzCCE, HgO, AgOAc or LiOAc, or in the presence of a base such as sodium or potassium hydroxide, potassium phosphate or sodium bicarbonate, in a suitable solvent such as methanol, ethanol, dichloromethane, tetrahydrofuran, toluene, xylene, A, A-dimethylformamide or DMSO, at a temperature in the range of 0 °C to 160 °C. Such reactions are described previously; see for example Chem. Rev. 2021, 121, 412-484.

[0278] A process for the synthesis of compounds of formula (2aa-2ac) is depicted in the schemes 4a-c:

[0279] Scheme: 4a wherein, X is halogen, R1and R2have the meanings as described above.

[0280] The pyrazole derivative of formula (7) can undergo a cyclocondensation reaction when treated with dielectrophilic compounds of formula (8) or its protected / masked (e.g. aldehyde masked as a ketal) version to provide the compounds of formula (9). The condensation can be effected in a solvent, in the presence of an acid. Examples of the acid include but are not limited to 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, ethylene glycol and the like. The reaction can be carried out at a temperature in the range of 0 °C to 150 °C.

[0281] Compounds of formula (10) can be obtained by treating compounds of formula (9) with a halogenating agent, in the presence or absence of a base and a solvent. Examples of the solvents include but are not limited to acetonitrile, chloroform, tetrahydrofuran, 1,4-dioxane, toluene, N, A-dimethylformamide and the like. Examples of halogenating agents include but are not limited to phosphorus oxychloride, thionyl chloride, phosphorus pentachloride and the like. Examples of bases include but are not limited to N, N- dimethylaniline, diisopropylethylamine, A-mcthylmorpholinc and the like. The reaction can be carried out at a temperature in the range of 50 °C to 200 °C.

[0282] Halo compounds of formula (10) can be conveniently coupled under Suzuki cross-coupling conditions with boronic acids or boronic ester compounds of formula (11) to obtain the compounds of formula (13). The Suzuki cross-coupling reaction can be catalyzed by a palladium based catalyst, including but are not limited to l,T-bis(diphenylphosphino)ferrocene] dichloropalladium (II) or tetrakis(triphenylphosphine) palladium (0), in a suitable solvent for example, tetrahydrofuran, N,N- dimethylformamide, 1,2-dimethoxyethane, 1,4-dioxane or a solvent system such as a mixture of tetrahydrofuran / water, 1,2-dimethoxyethane / water, 1,4-dioxane / water, or the like. The reaction is usually carried out in the presence of a suitable base, for example, potassium carbonate, cesium carbonate or potassium phosphate. The reaction temperature can preferentially range from the ambient temperature (20 °C) to the boiling point of the reaction mixture as precedented in the literature, see for example ('hem. Soc. Rev. 2014, 43, 412-443 or W02014070978.

[0283] Alternatively, compounds of formula (13) can be obtained by Stille reaction conditions using a reagent of formula (12), in the presence of a catalyst such as bis(triphenylphosphine)palladium(II)dichloride, tetrakis(triphenylphosphine)palladium(0), 1,1’ -bis(diphenylphosphino)ferrocene palladium(II)chloride, tris(dibenzylideneacetone)dipalladinm(0), and palladium(II)acetate; nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride; and copper catalyst such as copper(I) iodide and copper(I) chloride, in the presence of a base such as alkali metal hydrides, alkali metal carbonates, and organic bases, in a suitable solvent such as acetonitrile, tetrahydrofuran, N,N- dimethylformamide, 1,2-dimethoxyethane or 1,4-dioxane, at a temperature between 25 °C and the reflux temperature of the solvent, or under microwave irradiation at a temperature ranging from 70 °C to 150 °C. A ligand and / or an inorganic halogenated compound may be added to the reaction as needed. Examples of ligands to be used in the reaction include triphenylphosphine, XantPhos, 2,2’- bis(diphenylphosphino)- 1 , l’-binaphthyl, 1,1’ -bis(diphenylphosphino)ferrocene, 2-

[0284] (dicyclohexylphosphino)-2’, 4’, 6 ’-triisopropyl- 1,1’ -biphenyl, 2-aminoethanol, 8 -hydroxy quinoline and 1,10-phenanthroline. Examples of inorganic halogenated compounds include alkali metal fluorides such as potassium fluoride, and sodium fluoride; and alkali metal halides such as lithium chloride and sodium chloride.

[0285] The hydrolysis of the compounds of formula (13) can be achieved by using a base such as sodium hydroxide, potassium hydroxide, lithium hydroxide, Bis(tributyltin) oxide and the like; in a suitable solvent such as tetrahydrofuran, water, methanol, ethanol, toluene or a mixture thereof, to obtain the compounds of formula (2aa). The reaction can be carried out at a temperature in the range of 50 °C to 150 °C.

[0286] A process for the synthesis of the compounds of formula (2ab) is depicted in scheme 4b:

[0287] Scheme: 4b wherein, R1and R2have the meanings as described above.

[0288] Compounds of formula (15) can be prepared by the cyclization of the pyrazole derivative of formula (7) with commercially available 2-halo-malonaldehydes of formula (14) under acid-catalyzed conditions in the presence of a solvent. Examples of 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, ethylene glycol and the like. The reaction can be carried out at a temperature in the range of 0 °C to 150 °C. The compounds of formula (15) can be further conveniently coupled under Suzuki cross-coupling conditions or Stille cross-coupling conditions using the reagents of formula (16) to obtain the compounds of formula (17) as described in step 3 or step 4 of scheme 4a. A subsequent alkaline hydrolysis of the compounds of formula (17) can be achieved as described in step 5 of scheme 4a to obtain the compounds of formula (2ab).

[0289] The compounds of formula (2ac) can be prepared according to the following scheme 4c: wherein, R1and R2have the meanings as described above.

[0290] Pyrazole derivatives of formula (7) can undergo cyclocondensation with the 1,3 -dimethyluracil of formula (18) or alkoxyacrylate derivatives of formula (19) in the presence of a suitable base to obtain pyrimidin-5-one derivatives of formula (20). Examples of suitable bases include sodium ethoxide, sodium methoxide, potassium tert-butoxide, potassium carbonate, sodium carbonate, cesium carbonate, potassium phosphate and the like. The reaction is carried out in the presence of a solvent selected from but not limited to methanol, ethanol, isopropanol, ethylene glycol, N, A-dimcthylacctamidc or N,N- dimethylformamide. 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; W02018081417. A halogenation of compounds of formula (20) with phosphorus oxychloride or phosphorus oxybromide provides compounds of formula (21). The compounds of formula (21) can be conveniently coupled under Suzuki cross-coupling conditions or Stille cross-coupling conditions to obtain the compounds of formula (22) as described in step 3 or step 4 of scheme 4a. A subsequent alkaline hydrolysis of compounds of formula (22), as described in step 5 of scheme 4a, provides compounds of formula (2ac). wherein, R1, R7and R8have the meanings as described above.

[0291] Compounds of formula (24a / 24b / 24c) can be prepared by reacting compounds of formula (10 / 15 / 21) with a reagent of formula (23), in the presence of a base. Examples of the base include but are not limited to sodium, potassium or cesium carbonate, or sodium or potassium tert-butylate, or diisopropylethylamine or triethylamine or DBU, or pyridine, in a suitable solvent such as tetrahydrofuran, A'.A'-dimcthylfonnamidc. acetonitrile and dimethyl sulfoxide. The reaction can be carried out at a temperature in the range of 25 °C to 130 °C.

[0292] Alternatively, compounds of formula (24a / 24b / 24c) can be prepared by reacting compounds of formula (10 / 15 / 21) under transition metal catalyzed conditions. The reaction may be catalyzed by a palladium based catalyst, for example, bis(dibenzylideneacetone)palladium(0) (Pd(dba)2), tris(dibenzylideneacetone)dipalladinm(0) (Pd2(dbaf,: optionally in the form of its chloroform adduct or palladium(II) acetate , and a ligand, for example XantPhos ((5-di-phenylphosphanyl-9,9-dimethyl- xanthen-4yl)diphenylphosphane), XPhos (2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl), RuPhos (2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl), BINAP (2,2’- bis(diphenylphosphino)-l,l’-binaphthalene), in the presence of a base, like sodium, potassium or cesium carbonate, or sodium, potassium tert-butylate, or potassium phosphate, in a solvent or a solvent mixture, for example, 1,4-dioxane, 1,2-dimethoxyethane or toluene, preferably under an inert atmosphere. The reaction temperature can preferentially range from 25 °C to the boiling point of the reaction mixture, or the reaction may be performed under microwave irradiation. Such reactions, and alternative conditions such as iron or copper catalysis, have been described, for example, in WO2018 / 099812.

[0293] Alternatively, compounds of formula (24a / 24b / 24c) can be prepared by copper or nickel catalysis. Examples of such catalysts to be used in the reaction include copper catalysts such as copper(I)iodide, copper(I)bromide, copper(I)chloride, copper(I)oxide, trifluromethanesulfonicacid copper(I)salt benzene complex , 2 -thiophenecarboxy lie acid copper(I)salt; and nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel chloride, and a ligand, for example 1,10-phenanthroline, 8- hydroquinoline, trans- 1,2-cyclohexanediamine, trans- l,2-bis(methylamino)cyclohexane, N,N- dimethylethylenediamine, 2,2'-bipyridine, 2-aminoethanol, triphenyl phosphine, 1,2- bis(diphenylphosphino)ethane, l,3-bis(diphenylphosphino)propane, XantPhos ((5-di- phenylphosphanyl-9,9-dimethyl-xanthen-4yl)diphenylphosphane), XPhos (2-Dicyclohexylphosphino- 2',4',6'-triisopropylbiphenyl), RuPhos (2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl), BINAP (2,2 ’ -bis(diphenylphosphino)- 1 , 1 ’ -binaphthalene), 1,1’ -bis(diphenylphosphino)ferrocene . Examples of the base include but are not limited to alklaimetal carbonates, or diisopropylethylamine or pyridine or 1, 8 -Diazabicyclo [5.4.0] undec-7-ene or 4-(dimethylamino) pyridine, in an appropriate solvent such as acetonitrile, dimethyl slufoxide, A'.A'-dimcthylfonnamidc. A'.A'-dimcthyl acetamide or A-methyl-2- pyrrolidone, at a temperature in the range of 25 °C to 120 °C.

[0294] A subsequent alkaline hydrolysis of compounds of formula (24a / 24b / 24c), as described in step 5 of scheme 4a, provides compounds of formula (2ad / 2ae / 2af). wherein, Ai, A2, R1, R2, R3, R7and R8have the meanings as described above.

[0295] Compounds of formula (Za) can be prepared by reacting with the compounds of formula (25a / 25b / 25c) using conditions described in step-3 or step-4 of scheme-4a. Similarly, compounds of formula (Za-1) can be prepared from the compounds of formula (25a / 25b / 25c) using the conditions as described in step-1 of scheme-5.

[0296] Scheme: 7

[0297] wherein, Ai, A2, R1, R2and R3have the meanings as described above

[0298] A process for the synthesis of compounds of formula (25a / 25b / 25c) is depicted in scheme-7.

[0299] Organo sulfanylalkenes of formula (27) can be obtained by reacting cyano compounds of formula (26) 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 an appropriate solvent such as tetrahydrofuran, acetonitrile and AA'-dimcthylfromamidc. at a temperature in the range of 0 to 50 °C. The compounds of formula (27) can be cyclized to aminopyrazole derivative of formula (28) using hydrazine. The aminopyrazole derivative (28) can be converted in to compounds of formula (25a-c) using the methods described in scheme 4a (Step 1&2) or scheme 4b (Step 1) or scheme 4c (Step 1&2).

[0300] Alternatively, a pyrazole derivative (28) can be obtained by treating compounds of formula (Za’) with hydrazine hydrate in the presence of a solvent such as methanol, ethanol, isopropanol, tetrahydrofuran, acetonitrile or dioxane, at a temperature in the range of 25 °C to 120 °C. wherein, Ai, A2, R1, R2and R3have the meanings as described above. Formula (28), shown above, is also referred to as formula (I-w) in the description and claims; both designations represent the same compound.

[0301] In another process, compounds of formula (Z-l) can be prepared by reacting the pyrazole derivative of formula (28) with compounds of formula (29) under cyclocondensation conditions, in the presence of a solvent or an acid. Examples of acids include acetic acid, sulfonic acid (e.g. PTSA), sulfuric acid and hydrochloric acid, which liberate the reactive functional group. Examples of solvents include but are not limited to methanol, ethanol, isopropanol, ethylene glycol and the like. The reaction can be carried out at a temperature in the range of 50 °C to 150 °C.

[0302] Synthetic methods to prepare the reagents of formula (29) are known in the literature. wherein, Ai, A2, R1, R2, R2' and R3have the meanings as described above.

[0303] The compounds of formula (Z-2) can be prepared according to scheme-8 by cyclocondensing the pyrazole derivative of formula (28) and keto ester of formula (30) 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 °C to 150 °C. wherein, Ai, A2, R1, R2, R2' and R3have the meanings as described above.

[0304] The compounds of formula (28) can be condensed with the compounds of formula (31) 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 out 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. wherein, Ai, A2, R1, R2, R2' and R3have the meanings as described above. The compounds of formula (IA), wherein n=l (sulfoxide) and / or n=2 (sulfone), can be obtained by the oxidation of the corresponding sulfide compounds 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 and other organic peracids and the like can be used for this . The oxidation is carried out at a temperature in the range of 0 to 100 °C. Examples of solvents used in this reaction include aliphatic halogenated hydrocarbons such as dichloromethane, chloroform: alcohols such as methanol and ethanol and mixtures thereof. wherein, Ai, A2, R1, R2, R2' and R3have the meanings as described above.

[0305] The compounds of formula (IB), wherein RY= H represented as formula (IB1), can be obtained by reacting compounds 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.

[0306] Compounds of formula (IB), wherein RYis other than ‘H’ represented as formula (IB") 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 trifluoromethane sulfonate. The alkylation reaction can be performed in the presence of bases such as sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, cesium carbonate or trimethylamine, in the presence of a solvent such as dichloromethane, dichloromethane, A'.A'-dimcthylformamidc. 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 (IB) wherein RY= other than ‘H’ can be performed in the presence of a base, such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydroxide, in an inert solvent, such as toluene, N,N- dimethylformamide, N-methyl pyrrolidine (NMP), DMSO, 1,4-dioxane, tetrahydrofuran and the like, optionally in the presence of a catalyst, for example palladium(II)acetate, bis(dibenzylideneacetone)palladium(0) (Pd(dba)2), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3 optionally in form of its chloroform adduct, or a palladium pre -catalyst such as for example tert-BuBrettPhos Pd G3 [(2 Di-tert-butylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-l,l’- biphenyl)-2-(2’-amino-l,l’-biphenyl)]palladium(II) methanesulfonate or BrettPhos Pd G3 [(2-di- cyclohexylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-l, 1 ’-biphenyl)-2-(2’-amino-l, 1 ’- biphenyl)]palladium(II) methanesulfonate, and optionally in the presence of a ligand, for example SPhos, / -BuBrcttPhos or XantPhos, at a temperature in the range of 50 to 120 °C, optionally under micro wave heating conditions.

[0307] As used herein, the compounds of formula (Z) represents a general structure from which the specific compounds of formulas (Za), (Za-1), (Za'), (Z-l), (Z-2), (Z-3) and (Z-4) are derived. These formulas are considered subsets or species encompassed within the scope of compounds of formula (Z).

[0308] CHEMISTRY EXAMPLES:

[0309] 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.

[0310] Example-1: Synthesis of 2-(7-cyclopropyl-2-(ethylsulfonyl)pyrazolo[l,5-a]pyrimidin-3-yl)-6- (trifluoromethyl)isoindolin-l-one (Compound No. 1)

[0311] Step-1: Synthesis of methyl 2-(bromomethyl)-5-(trifluoromethyl)benzoate

[0312] To a stirred solution of methyl 2-methyl-5-(trifluoromethyl)benzoate (10.0 g, 45.8 mmol) in carbon tetrachloride (lOO mL), A-bromosuccinimide (9.79 g, 55.0 mmol) was added at 25 °C for 10-15 minutes. To this reaction mixture, AIBN (0.90 g, 5.50 mmol) was added. The resulting mixture was stirred at 70 °C for 12 h. After the completion of the reaction, the reaction mixture was cooled to 25 °C and slowly quenched with saturated sodium bicarbonate solution (200 mL). The aqueous layer was extracted with dichloromethane (200 mL), the organic layer was washed with water (3 x 200 mL), saturated brine solution (200 mL), dried over anhydrous sodium sulphate, filtered and evaporated to get the crude product (12.5 g; 45.8 mmol; 92% yield). The crude product was used in the next step without any further purification. ’H-NMR (400 MHz, CHLOROFORM-D) 5 8.23 (d, J = 1.7 Hz, 1H), 7.74 (dd, J = 8.1, 1.5 Hz, 1H), 7.64-7.60 (m, 1H), 4.97 (s, 2H), 3.96 (d, J = 8.6 Hz, 3H); ESI MS (m / z) 297.9 (GCMS).

[0313] Step-2: Synthesis of methyl 2-(((tert-butoxycarbonyl)(7-cyclopropyl-2-(ethylthio)pyrazolo[l,5- a]pyrimidin-3-yl)amino)methyl)-5-(trifluoromethyl)benzoate To a stirred solution of tert-butyl (7-cyclopropyl-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)carbamate (1.7 g, 5.08 mmol) in acetonitrile (20 mb), cesium carbonate (2.48 g, 7.62 mmol) and methyl 2- (bromomethyl)-5-(trifluoromethyl)benzoate (2.26 g, 7.62 mmol) were added at 25 °C. The resulting mixture was heated to 50 °C and stirred for 14 h. After the completion of the reaction, the mixture was cooled to 25 °C and poured into ice water (150 mL). The aqueous layer was extracted with ethyl acetate (3 x 75 mL), and the combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to get the crude compound which was purified by flash column chromatography to obtain methyl 2-(((tert-butoxycarbonyl)(7-cyclopropyl-2-(ethylthio)pyrazolo[l,5- a]pyrimidin-3-yl)amino)methyl)-5-(trifluoromethyl)benzoate (2.35 g, 4.27 mmol, 84 % yield).1H- NMR (400 MHz, DMSO-J6) 5 8.36 (d, J = 4.6 Hz, 1H), 8.06 (d, J = 8.6 Hz, 1H), 8.01-7.94 (m, 2H), 6.62 (d, J = 4.4 Hz, 1H), 5.22 (d, J = 16.9 Hz, 2H), 3.71-3.64 (m, 3H), 3.19-3.00 (m, 2H), 2.80-2.73 (m, 1H), 1.40-1.25 (m, 12H), 1.23-1.07 (m, 4H); ESI MS (m / z) 551.65 (MH)+.

[0314] Step-3: Synthesis of 2-(7-cyclopropyl-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)-6-

[0315] (trifluoromethyl) isoindolin-l-one

[0316] To an ice-cold solution of methyl 2-(((tert-butoxycarbonyl)(7-cyclopropyl-2-(ethylthio)pyrazolo[l,5- a]pyrimidin-3-yl)amino)methyl)-5-(trifluoromethyl)benzoate (2.3 g, 4.18 mmol) in dichloromethane (25 mL), TFA (3.2 mL, 41.8 mmol) was added dropwise over 10 minutes. The resulting reaction mixture was gradually warmed to 25 °C and stirred for 16 h at the same temperature. After the completion of the reaction, the resulting mixture was diluted with dichloromethane (150 mL) and washed with saturated sodium bicarbonate solution (2 x 100 mL), followed by saturated brine solution (100 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to get a crude compound which was purified by flash column chromatography to obtain 2-(7-cyclopropyl-2- (ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)isoindolin-l-one (1.3 g, 3.11 mmol, 74.4 % yield). ’H-NMR (400 MHz, DMSO-J6) 5 8.38 (d, J = 4.4 Hz, 1H), 8.08 (d, J = 6.6 Hz, 2H), 7.93 (d, J = 8.3 Hz, 1H), 6.74 (d, J = 4.6 Hz, 1H), 4.99 (s, 2H), 3.16 (q, J = 7.3 Hz, 2H), 2.86-2.79 (m, 1H), 1.37- 1.28 (m, 5H), 1.26-1.20 (q, 2H); ESI MS (m / z) 419.6 (MH)+.

[0317] Step-4: Synthesis of 2-(7-cyclopropyl-2-(ethylsulfonyl)pyrazolo[l,5-a]pyrimidin-3-yl)-6- (trifluoromethyl)isoindolin-l-one (compound No. 1)

[0318] To an ice cold solution of 2-(7-cyclopropyl-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)-6- (trifluoromethyl)isoindolin-l-one (260 mg, 0.621 mmol) in dichloromethane (10 mL), 3- chloroperoxybenzoic acid (393 mg, 1.37 mmol) was added and the reaction mixture was stirred at 25 °C for 2 h. After the completion of the reaction, the resulting mixture was diluted with dichloromethane (100 mL). The organic layer was washed with saturated sodium bicarbonate solution (100 mL), saturated sodium thiosulfate 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 2-(7-cyclopropyl-2-(ethylsulfonyl) pyrazolo[l,5-a]pyrimidin-3-yl)-6- (trifluoromethyl)isoindolin-l-one (185 mg, 0.411 mmol, 66.1 % yield). ’H-NMR (400 MHz, DMSO- d6) 5 8.63 (d, J = 4.6 Hz, 1H), 8.11 (d, J = 4.9 Hz, 2H), 7.96 (d, J = 8.6 Hz, 1H), 7.07 (d, J = 4.6 Hz, 1H), 5.01 (s, 2H), 3.53 (q, J = 7.4 Hz, 2H), 2.88-2.81 (m, 1H), 1.43-1.38 (m, 2H), 1.27-1.23 (m, 5H); ESI MS (m / z) 451.55 (MH)+.

[0319] Example-2: Synthesis of 2-(7-cyclopropyl-2-(N-methylethylsulfonimidoyl)pyrazolo[l,5- a]pyrimidin-3-yl)-6-(trifluoromethyl)isoindolin-l-one (Compound No. 4)

[0320] Step-1: Synthesis of 2-(7-cyclopropyl-2-(ethylsulfonimidoyl)pyrazolo[l,5-a]pyrimidin-3-yl)-6- (trifluoromethyl)isoindolin-l-one (Compound 2)

[0321] A stirred solution of 2-(7-cyclopropyl-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)-6- (trifluoromethyl)isoindolin-l-one (1.0 g, 2.39 mmol; Step-3: Example-1) in methanol (20 mL) was cooled to 0 °C, and treated with iodobenzene diacetate (1.92 g, 5.97 mmol). Ammonium carbamate (0.93 g, 11.95 mmol) was added in portions, and the resulting reaction mixture was stirred at 0 °C for 10 minutes. The mixture was then gradually warmed to 25 °C and continued to stir further at the same temperature for 12 h. After completion of the reaction, methanol was evaporated under reduced pressure to obtain a crude compound, which was purified by flash column chromatography to obtain 2-(7- cyclopropyl-2-(ethylsulfonimidoyl)pyrazolo [1,5 -a]pyrimidin-3 -yl)-6-(trifluoromethyl)isoindolin- 1 - one (750 mg, 1.669 mmol, 69.8 % yield). ’H-NMR (400 MHz, DMSCM,) 5 8.58-8.55 (m, 1H), 8.09- 8.08 (m, 2H), 7.96-7.94 (m, 1H), 7.00 (d, J = 4.6 Hz, 1H), 5.00 (s, J = 18.3 Hz, 2H), 3.43-3.34 (q, 2H), 2.89-2.82 (m, 1H), 1.42-1.35 (m, 2H), 1.28-1.16 (m, 5H); ESI MS (m / z) 450.45 (MH)+.

[0322] Step-2: Synthesis of 2-(7-cyclopropyl-2-(N-methylethylsulfonimidoyl)pyrazolo[l,5-a]pyrimidin- 3-yl)-6-(trifluoromethyl)isoindolin-l-one (Compound No. 4)

[0323] To a stirred solution of 2-(7-cyclopropyl-2-(ethylsulfonimidoyl)pyrazolo[l,5-a]pyrimidin-3-yl)-6- (trifluoromethyl)isoindolin-l-one (220 mg, 0.49 mmol) in 1,4-dioxane (8 mL), under atmospheric air, copper (II) acetate (133 mg, 0.74 mmol) and pyridine (0.1 mL, 1.175 mmol) were added at 25 °C. The resulting reaction mixture was purged with zero air for 10-15 minutes at 25 °C, treated with methylboronic acid (59 mg, 0.98 mmol) and stirred at 100 °C for 3 h under zero air balloon. After the completion of the reaction, the resulting mixture was cooled to 25 °C and 1,4-dioxane was evaporated. The residue was diluted with water (50 mL) and the aqueous layer was extracted with ethyl acetate (3 x 25 mL). The combined organic layers were washed with saturated brine solution (50 mL), dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to obtain a crude compound which was purified by flash column chromatography to obtain 2-(7-cyclopropyl-2-(N- methylethylsulfonimidoyl)pyrazolo[ 1 ,5 -a]pyrimidin-3-yl)-6-(trifluoromethyl)isoindolin- 1 -one (100 mg, 0.216 mmol, 44.1 % yield). ’H-NMR (400 MHz, DMSO-J6) 58.56 (dd, J = 11.3, 4.6 Hz, 1H), 8.17- 8.04 (m, 2H), 7.94 (t, J = 9.0 Hz, 1H), 6.98 (dd, J = 20.6, 4.4 Hz, 1H), 4.99 (s, J = 28.9, 17.9 Hz, 2H), 3.50-3.37 (q, 2H), 2.88-2.81 (m, 1H), 2.63 (s, J = 12.2 Hz, 3H), 1.42-1.36 (q, 2H), 1.31-1.20 (m, 5H) ESI MS (m / z) 463.55 (MH)+.

[0324] Example-3: Synthesis of 2-(2-(ethylsulfonyl)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidin-3-yl)-6- (trifluoromethyl)-2,3-dihydro-lH-pyrrolo[3,4-c]pyridin-l-one (Compound No. 54)

[0325] Step-1: Synthesis of Methyl 5-(bromomethyl)-2-(trifluoromethyl)isonicotinate

[0326] The titled compound methyl 5-(bromomethyl)-2-(trifluoromethyl)isonicotinate (34 g, 114 mmol, 93.0 % yield) was prepared from methyl 5 -methyl -2-(trifluoromethyl)isonicotinate (27 g, 123 mmol) using the procedure as mentioned in step-1 of the example- 1.

[0327] ’H-NMR (400 MHz, CHLOROFORM-D) 58.85 (s, 1H), 8.13 (s, 1H), 4.93 (s, 2H), 4.02 (d, J = 3.4 Hz, 3H); ESI MS (m / z) 299.65 (MH)+.

[0328] Step-2: Synthesis of Methyl 5-(((tert-butoxycarbonyl)(2-(ethylthio)-7-(pyrimidin-2- yl)pyrazolo[l,5-a] pyrimidin-3-yl)amino)methyl)-2-(trifluoromethyl)isonicotinate

[0329] The titled compound methyl 5-(((tert-butoxycarbonyl)(2-(ethylthio)-7-(pyrimidin-2-yl) pyrazolo[l,5-a] pyrimidin-3-yl)amino)methyl)-2-(trifluoromethyl)isonicotinate (2.1 g, 3.56 mmol, 41.5 % yield) was prepared from tert-butyl (2-(ethylthio)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidin-3-yl)carbamate (3.2 g, 8.59 mmol) and methyl 5-(bromomethyl)-2-(trifluoromethyl)isonicotinate (5.12 g, 17.18 mmol), using the procedure as mentioned in step-2 of the example-1. ESI MS (m / z) 590.25(MH)+.

[0330] Step-3: Synthesis of 2-(2-(ethylthio)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidin-3-yl)-6- (trifluoromethyl)-2,3-dihydro-lH-pyrrolo[3,4-c]pyridin-l-one

[0331] The titled compound 2-(2-(ethylthio)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidin-3-yl)-6- (trifluoromethyl)-2,3-dihydro-lH-pyrrolo[3,4-c]pyridin-l-one (850 mg, 1.858 mmol, 54.8 % yield) was prepared from methyl 5-(((tert-butoxycarbonyl)(2-(ethylthio)-7-(pyrimidin-2-yl)pyrazolo[l,5-a] pyrimidin-3-yl)amino)methyl)-2-(trifluoromethyl)isonicotinate (2.0 g, 3.39 mmol) using the procedure as mentioned in step-3 of the example- 1. ’H-NMR (400 MHz, DMSO-J6) 59.20 (s, 1H), 9.13 (d, J = 4.9 Hz, 2H), 8.74 (d, J = 4.3 Hz, 1H), 8.26 (s, 1H), 7.78 (t, J = 5.0 Hz, 1H), 7.44 (d, J = 4.3 Hz, 1H), 5.19 (s, 2H), 3.00 (q, J = 7.3 Hz, 2H), 1.24 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 457.9 (MH)+.

[0332] Step-4: Synthesis of 2-(2-(ethylsulfonyl)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidin-3-yl)-6- (trifluoromethyl)-2,3-dihydro-lH-pyrrolo[3,4-c]pyridin-l-one (Compound No. 54)

[0333] The titled compound 2-(2-(ethylsulfonyl)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidin-3-yl)-6- (trifluoromethyl)-2,3-dihydro-lH-pyrrolo[3,4-c]pyridin-l-one (200 mg, 0.409 mmol, 93 % yield) was prepared from 2-(2-(ethylthio)-7-(pyrimidin-2-yl)pyrazolo[l,5-a] pyrimidin-3-yl)-6-(trifluoromethyl)- 2,3-dihydro-lH-pyrrolo[3,4-c]pyridin-l-one (200 mg, 0.437 mmol) using the procedure as mentioned in step-4 of the example- 1.

[0334] ’H-NMR (400 MHz, DMSO-J6) 59.24 (s, 1H), 9.17 (d, J = 5.1 Hz, 2H), 8.98 (d, J = 4.2 Hz, 1H), 8.30 (s, 1H), 7.82 (dd, J = 5.7, 4.5 Hz, 2H), 5.18 (s, 2H), 3.47 (q, J = 7.3 Hz, 2H), 1.21 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 490 (MH)+.

[0335] Example-4: Synthesis of tert-butyl (2-(ethylthio)-7-(pyrimidin-2-yl)pyrazolo[l,5-a] pyrimidin-3- yl)carbamate

[0336] Step-1: Synthesis of 3-(dimethylamino)-l-(pyrimidin-2-yl)prop-2-en-l-one

[0337] To a stirred solution of l-(pyrimidin-2-yl)ethan-l-one (5.0 g, 40.9 mmol) in A. A-dimcthylfonnamidc (50 mL) under a nitrogen atmosphere, DMF-DMA (6.6 mL, 49.1 mmol) was added dropwise. The resulting reaction mixture was stirred at 110 °C for 12 h. After the completion of the reaction, the resulting mixture was evaporated under reduced pressure to obtain crude 3 -(dimethylamino)- 1- (pyrimidin-2-yl)prop-2-en-l-one (7.1 g, 40.1 mmol, 98 % yield) which was used as it is for the next step without further purification. ’H-NMR (400 MHz, DMSO-t / e) 5 8.89 (d, J = 4.9 Hz, 2H), 7.77-7.72 (m, 1H), 7.55 (t, J = 4.9 Hz, 1H), 6.14 (s, 1H), 3.24-3.13 (m, 3H), 2.89 (s, 3H); ESI MS (m / z) 177.60(MH)+.

[0338] Step-2: Synthesis of ethyl 2-(ethylthio)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidine-3- carboxylate

[0339] To a stirred solution of ethyl 3-amino-5-(ethylthio)-lH-pyrazole-4-carboxylate (7.2 g, 33.4 mmol) in acetic acid (70 mL) under nitrogen atmosphere, 3 -(dimethylamino)- l-(pyrimidin-2-yl)prop-2-en-l -one (7.1 g, 40.1 mmol) was added and the resulting mixture was stirred at 110 °C for 1.5 h. After the completion of the reaction, the solvent was evaporated. The residue was dissolved in ethyl acetate (200 mL), and washed with saturated brine solution (3 x 200 mL). The organic layer was dried over anhydrous sodium sulfate, fdtered and concentrated under reduced pressure to get the crude product. The crude product was purified by flash column chromatography to obtain ethyl 2-(ethylthio)-7- (pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidine-3-carboxylate (9.0 g, 27.3 mmol, 82% yield). ’H-NMR (400 MHz, DMSO-J6) 5 9.10 (d, J = 4.9 Hz, 2H), 8.91 (d, J = 4.6 Hz, 1H), 7.76 (t, J = 4.9 Hz, 1H), 7.52 (d, J = 4.3 Hz, 1H), 4.31 (q, J = 7.1 Hz, 2H), 2.98 (q, J = 7.3 Hz, 2H), 1.34-1.25 (m, 6H); ESI MS (m / z) 330.05 (MH)+.

[0340] Step-3: Synthesis of 2-(ethylthio)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidine-3-carboxylic acid

[0341] To a stirred solution of ethyl 2-(ethylthio)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidine-3-carboxylate (6.2 g, 18.8 mmol) in ethanol (80 mL), lithium hydroxide monohydrate (2.4 g, 56.5 mmol) in water (20 mL) was added. The resulting reaction mixture was stirred at 60 °C for 3 h. After the completion of the reaction, the mixture was cooled to 25 °C, diluted with water and acidified with 10% hydrochloric acid solution. The resulting mixture was then extracted with ethyl acetate (2 x 100 mL), the combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to get the desired 2-(ethylthio)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidine-3-carboxylic acid (2.0 g, 6.64 mmol, 35.3 % yield), which was used in the next step without any further purification. ’H- NMR (400 MHz, DMSCM,) 5 9.09 (q, J = 5.1 Hz, 2H), 8.90-8.86 (m, 1H), 7.75 (t, J = 5.0 Hz, 1H), 7.48 (d, J = 4.4 Hz, 1H), 2.96 (q, J = 7.3 Hz, 2H), 1.28 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 301.45 (MH)+.

[0342] Step-4: Synthesis of tert-butyl (2-(ethylthio)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidin-3- yl)carbamate

[0343] To a stirred solution of 2-(ethylthio)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidine-3-carboxylic acid (1.3 g, 4.31 mmol) in t-butanol (30 mL) and triethylamine (0.96 mL, 6.90 mmol) at 90 °C, diphenylphosphoryl azide (1.48 mL, 6.90 mmol) was added dropwise. The resulting reaction mixture was stirred at 90 °C for 3 h. After the the completion of the reaction, the reaction mixture was cooled to 25 °C and poured in to an ice water (100 mL). The aqueous layer was extracted with ethyl acetate (2 x 100 mL), the combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to get the crude compound which was purified by flash column chromatography to obtain tert-butyl (2-(ethylthio)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidin-3- yl)carbamate (350 mg, 0.940 mmol, 21.78% yield). ESI MS (m / z) 372.95(MH)+. Example-5: Synthesis of tert-butyl (7-cyclopropyl-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3- yl)carbamate

[0344] Step-1: Synthesis of l-cyclopropyl-3-(dimethylamino)prop-2-en-l-one

[0345] The titled compound l-cyclopropyl-3-(dimethylamino)prop-2-en-l-one (32 g, 230 mmol, 64.5 % yield) was prepared from 1-cyclopropylethan-l-one (35.3 ml, 357 mmol) using the procedure as mentioned in step-1 of the example-4 ’H-NMR (400 MHz, CHLOROFORM-D) 5 7.50 (d, J = 12.7 Hz, 1H), 5.15 (d, J = 12.7 Hz, 1H), 2.91-2.83 (m, 6H), 1.76-1.72 (m, 1H), 0.94 (dd, J = 20.4, 18.7 Hz, 2H), 0.75-0.68 (m, 2H); ESI MS (m / z) 139.75 (MH)+.

[0346] Step-2: Synthesis of ethyl 7-cyclopropyl-2-(ethylthio)pyrazolo[l,5-a]pyrimidine-3-carboxylate

[0347] The titled compound ethyl 7-cyclopropyl-2-(ethylthio)pyrazolo[l,5-a]pyrimidine-3-carboxylate (18.5 g, 63.5 mmol, 91 % yield) was prepared from ethyl 3-amino-5-(ethylthio)-lH-pyrazole-4-carboxylate (15 g, 69.7 mmol) and l-cyclopropyl-3-(dimethylamino)prop-2-en-l-one (11.15 g, 80 mmol) using the procedure as mentioned in step-2 of the example-4. ’H-NMR (400 MHz, CHLOROFORM-D) 5 8.51 (d, J = 4.6 Hz, 1H), 6.38 (d, J = 4.9 Hz, 1H), 4.46 (q, J = 7.0 Hz, 2H), 3.26 (q, J = 7.3 Hz, 2H), 2.94- 2.87 (m, 1H), 1.51-1.42 (m, 6H), 1.40-1.35 (m, 2H), 1.22-1.12 (m, 2H); ESI MS (m / z) 292.25 (MH)+.

[0348] Step-3: Synthesis of 7-cyclopropyl-2-(ethylthio)pyrazolo[l,5-a]pyrimidine-3-carboxylic acid

[0349] The titled compound ethyl 7-cyclopropyl-2-(ethylthio)pyrazolo[l, 5 -a]pyrimidine-3 -carboxylic acid (10.0 g, 38.0 mmol, 92 % yield) was prepared from ethyl 7-cyclopropyl-2-(ethylthio)pyrazolo[l,5-a] pyrimidine-3 -carboxylate (12 g, 41.2 mmol) using the procedure as mentioned in step-3 of the example- 4 ’H-NMR (400 MHz, DMSO-J6) 5 12.26 (s, 1H), 8.51 (d, J = 4.6 Hz, 1H), 6.81 (d, J = 4.9 Hz, 1H), 3.18 (q, J = 7.4 Hz, 2H), 2.85-2.78 (m, 1H), 1.39 (q, J = 7.5 Hz, 3H), 1.35-1.31 (m, 2H), 1.23-1.19 (m, 2H); ESI MS (m / z) 263.95 (MH)+.

[0350] Step-4: Synthesis of tert-butyl (7-cyclopropyl-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3- yl)carbamate

[0351] The titled compound tert-butyl (7-cyclopropyl-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)carbamate (2.1 g, 6.28 mmol, 41.3 % yield) was prepared from 7-cyclopropyl-2-(ethylthio)pyrazolo[l,5-a] pyrimidine-3 -carboxylic acid (4.0 g, 15.19 mmol) using the procedure as mentioned in step-4 of the example-4. ‘H-NMR (400 MHz, CHLOROFORM-D) 5 8.27 (d, J = 4.4 Hz, 1H), 7.27 (t, J = 1.3 Hz, 1H), 6.22 (d, J = 4.4 Hz, 1H), 3.20 (q, J = 7.3 Hz, 2H), 2.90-2.83 (m, 1H), 1.55-1.48 (m, 9H), 1.41 (t, J = 7.5 Hz, 3H), 1.37-1.28 (m, 2H), 1.13-1.09 (m, 2H); ESI MS (m / z) 334.95 (MH)+.

[0352] Example-6: Synthesis of tert-butyl (2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)carbamate

[0353] Step-1: Synthesis of ethyl 2-(ethylthio)pyrazolo[l,5-a]pyrimidine-3-carboxylate

[0354] To a stirred solution of ethyl 5-amino-3-(ethylthio)-lH-pyrazole-4-carboxylate (30 g, 139 mmol) in acetic acid (150 mL), 3-(dimethylamino)prop-l-en-l-one (16.7 mL, 167 mmol) was added. The resulting reaction mixture was stirred at 110 °C for 12 h. After the completion of the reaction, the mixture was quenched with ice cold water (500 mL), the precipitated solid product was filtered, washed with water (500 mL) followed by 10% ethyl acetate in hexane (250 mL) and dried under vacuum to obtain ethyl 2-(ethylthio) pyrazolo[l,5-a] pyrimidine -3 -carboxylate (31.0 g, 123 mmol, 89 % yield) as a brown solid product. ’H-NMR (400 MHz, CHLOROFORM-D) 5 8.69 (q, J = 2.0 Hz, 1H), 8.61 (dd, J = 6.9, 1.7 Hz, 1H), 6.91 (dd, J = 6.7, 4.3 Hz, 1H), 4.47 (q, J = 7.1 Hz, 2H), 3.23 (q, J = 7.4 Hz, 2H), 1.45 (q, J = 7.3 Hz, 6H); ESI MS (m / z) 252.10 (MH)+.

[0355] Step-2: Synthesis of 2-(ethylthio)pyrazolo[l,5-a]pyrimidine-3-carboxylic acid

[0356] To a stirred solution of ethyl 2-(ethylthio)pyrazolo[l,5-a]pyrimidine-3-carboxylate (32 g, 127 mmol) in ethanol (150 mL), lithium hydroxide monohydrate (53.4 g, 1273 mmol) in water (150 mL) was added. The resulting reaction mixture was stirred at 70 °C for 4 h. After the completion of the reaction, the mixture was concentrated under reduced pressure, diluted with water, and acidified with cone. HC1 (pH= 1). The solid residue was filtered and dried under reduced pressure to obtain 2- (ethylthio)pyrazolo[l,5-a]pyrimidine-3-carboxylic acid (26.5 g, 119 mmol, 93 % yield). ’H-NMR (400 MHz, DMSO-J6) 5 12.41 (s, 1H), 9.16-9.11 (m, 1H), 8.70-8.64 (m, 1H), 7.16 (dd, J = 6.7, 4.3 Hz, 1H), 3.13 (q, J = 7.3 Hz, 2H), 1.35 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 223.95 (MH)+.

[0357] Step-3: Synthesis of tert-butyl (2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)carbamate

[0358] To a stirred solution of 2-(ethylthio)pyrazolo[l,5-a]pyrimidine-3-carboxylic acid (26.0 g, 116 mmol) in tert-butanol (167 mL, 1747 mmol), triethylamine (26 mL, 186 mmol) was added and the reaction mixture was stirred at 90 °C. Diphenylphosphoryl azide (40. 1 mL, 186 mmol) was added to the mixture at 90 °C dropwise over 10 minutes. The reaction mixture was continued to stir at 90 °C for 3 h. After the completion of the reaction, the resulting mixture was cooled to 25 °C and poured into ice water (200 mL). The aqueous layer was extracted with ethyl acetate (2 x 150 mL), and the combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude compound which was purified by flash column chromatography to obtain the desired tertbutyl (2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)carbamate (13 g, 44.2 mmol, 37.9 % yield). ’H-NMR (400 MHz, CHLOROFORM-D) 5 8.55-8.44 (m, 1H), 8.38 (s, 1H), 7.16 (d, J = 21.8 Hz, 1H), 6.68 (dd, J = 6.4, 3.9 Hz, 1H), 3.23-3.09 (m, 2H), 1.57-1.44 (m, 9H), 1.43-1.36 (m, 3H); ESI MS (m / z) 294.90 (MH)+.

[0359] Example-7: Synthesis of ethyl 2-(ethylsulfonyl)-6-methyl-3-(5-oxo-3-(trifluoromethyl)-5,7- dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate (Compound No. 147)

[0360] Step-1: Synthesis of methyl 2-(bromomethyl)-5-(trifluoromethyl)nicotinate

[0361] The titled compound methyl 2 -(bromomethyl) -5 -(trifluoromethyl)nicotinate (20 g, 67.1 mmol, 82 % yield) was prepared from methyl 2-methyl-5 -(trifluoromethyl) nicotinate (18 g, 82 mmol) using the procedure as mentioned in step-1 of the example-1. ESI MS (m / z) 299.65(MH)+.

[0362] Step-2: Synthesis of methyl 2-(((tert-butoxycarbonyl)(2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3- yl)amino) methyl)-5-(trifluoromethyl)nicotinate

[0363] The titled compound (7.0 g, 13.68 mmol, 50.4 % yield) was prepared from tert-butyl (2- (ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)carbamate (8.0 g, 27.2 mmol) and methyl 2 -(bromomethyl) - 5-(trifluoromethyl)nicotinate (20.25 g, 67.9 mmol) using the procedure as mentioned in step-2 of the example-1. ESI MS (m / z) 512.15 (MH)+.

[0364] Step-3: Synthesis of 6-(2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)-3-(trifluoromethyl)-6,7- dihydro-5H-pyrrolo [3,4-b] pyridin-5-one

[0365] The titled compound (3.2 g, 8.44 mmol, 50.8 % yield) was prepared from methyl 2-(((tert- butoxycarbonyl)(2-(ethylthio)pyrazolo [1,5 -a]pyrimidin-3 -yl)amino)methyl)-5 -(trifluoromethyl) nicotinate (8.5 g, 16.62 mmol) using the procedure as mentioned in step-3 of the example-1. ’H-NMR (400 MHz, DMSO-J6) 5 9.29 (d, J = 1.5 Hz, 1H), 9.15 (dd, J = 7.0, 1.6 Hz, 1H), 8.63 (d, J = 1.7 Hz, 1H), 8.57 (q, J = 2.0 Hz, 1H), 7.10 (dd, J = 7.0, 4.0 Hz, 1H), 5.06 (s, 2H), 3.15 (q, J = 7.3 Hz, 2H), 1.32 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 380.60 (MH)+. Step-4: Synthesis of 6-(5-amino-3-(ethylthio)-lH-pyrazol-4-yl)-3-(trifluoromethyl)-6,7-dihydro- 5H-pyrrolo[3,4-b] pyridin-5-one

[0366] To a stirred solution of 6-(2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)-3-(trifluoromethyl)-6,7- dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (3.0 g, 7.91 mmol) in ethanol (30 mL), hydrazine hydrate (7.92 mL, 158 mmol) was added and the resulting reaction mixture was stirred at 90 °C for 3 h. After the completion of the reaction, the resulting mixture was cooled to 25 °C and poured into ice-cold water (100 mL). The aqueous layer was extracted with ethyl acetate (2 x 100 mL), and the combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain crude 6-(5-amino-3-(ethylthio)-lH-pyrazol-4-yl)-3-(trifluoromethyl)-6,7-dihydro-5H- pyrrolo[3,4-b]pyridin-5-one (2.4 g, 6.99 mmol, 88 % yield). The crude product was taken to the next step without further purification. ESI MS (m / z) 344.05(MH)+.

[0367] Step-5: Synthesis of ethyl 2-(ethylthio)-6-methyl-3-(5-oxo-3-(trifluoromethyl)-5,7-dihydro-6H- pyrrolo[3,4-b] pyridin-6-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate

[0368] To a stirred solution of 6-(5-amino-3-(ethylthio)-lH-pyrazol-4-yl)-3-(trifluoromethyl)-6,7-dihydro-5H- pyrrolo[3,4-b]pyridin-5-one (440 mg, 1.28 mmol) in ethanol (10 mL), ethyl 4-ethoxy-3-methyl-2- oxobut-3 -enoate (358 mg, 1.92 mmol) was added. The resulting reaction mixture was stirred at 85 °C for 2 h. After the completion of the reaction, the resulting mixture was cooled to 25 °C and poured into ice-cold water (100 mL). The aqueous layer was extracted with ethyl acetate (2 x 100 mL), the combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by flash column chromatography to obtain ethyl 2-(ethylthio)-6-methyl-3-(5-oxo-3-(trifluoromethyl)-5,7-dihydro-6H-pyrrolo[3,4- b]pyridin-6-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate (430 mg, 0.924 mmol, 72.1 % yield). ’H-NMR (400 MHz, CHLOROFORM-D) 5 9.07 (s, 1H), 8.48 (s, 1H), 7.26 (s, 1H), 5.11 (s, 2H), 4.45-4.40 (m, 2H), 3.25-3.18 (m, 2H), 2.50 (s, 3H), 1.40 (tt, J = 7.3, 1.9 Hz, 6H); ESI MS (m / z) 466.00 (MH)+.

[0369] Step-6: Synthesis of ethyl 2-(ethylsulfonyl)-6-methyl-3-(5-oxo-3-(trifluoromethyl)-5,7-dihydro- 6H-pyrrolo[3,4-b]pyridin-6-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate (Compound No. 147)

[0370] The titled compound (320 mg, 0.64 mmol, 94 % yield) was prepared from ethyl 2-(ethylthio)-6-methyl- 3 -(5 -oxo-3 -(trifluoromethyl) -5 ,7-dihydro-6H-pyrrolo [3 ,4-b]pyridin-6-yl)pyrazolo [ 1 ,5 -a]pyrimidine-7 - carboxylate (320 mg, 0.69 mmol) using the procedure as mentioned in step-4 of the example-1. ’H- NMR (400 MHz, DMSO-J6) 5 9.46 (d, J = 1.2 Hz, 1H), 9.32 (d, J = 1.2 Hz, 1H), 8.69 (d, J = 2.0 Hz, 1H), 5.07 (s, 2H), 4.44-4.35 (m, 2H), 3.55-3.47 (m, 2H), 2.46-2.43 (m, 3H), 1.30 (t, J = 7.1 Hz, 3H), 1.23 (td, J = 7.3, 2.7 Hz, 3H) ESI MS (m / z) 498.65 (MH)+.

[0371] Example-8: Synthesis of N-(2-cyanopropan-2-yl)-2-(ethylsulfonyl)-3-(5-oxo-2-(trifluoromethyl)-

[0372] 5,7-dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (Compound No. 163)

[0373] Step-1: Synthesis of ethyl 2-(ethylthio)-3-(5-oxo-2-(trifluoromethyl)-5,7-dihydro-6H-pyrrolo[3,4- b] pyridin-6-yl) pyrazolo[l,5-a]pyrimidine-7-carboxylate

[0374] To a stirred solution of ethyl (E)-4-ethoxy-2-oxobut-3-enoate (1.339 g, 7.78 mmol) in acetic acid (15 mL), 6-(5-amino-3-(ethylthio)-lH-pyrazol-4-yl)-2-(trifluoromethyl)-6,7-dihydro-5H-pyrrolo[3,4-b] pyridin-5-one (1.78 g, 5.18 mmol) (prepared using a similar way as described in the Example 7) was added and the reaction mixture was stirred at 100 °C for 2 h. After the completion of the reaction, the resulting mixture was evaporated to obtain a residue. The residue was dissolved in ethyl acetate (100 mL), washed with saturated brine solution (2 x 150 mL), dried over anhydrous sodium sulfate, filtered and evaporated to get a crude product. The crude product was purified by flash column chromatography to obtain ethyl 2-(ethylthio)-3-(5-oxo-2-(trifluoromethyl)-5,7-dihydro-6H-pyrrolo[3,4-b]pyridin-6- yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate (1.8 g, 3.99 mmol, 77 % yield) as brown solid. ESI MS (m / z) 452.20 (MH)+.

[0375] Step-2: Synthesis of ethyl 2-(ethylsulfonyl)-3-(5-oxo-2-(trifluoromethyl)-5,7-dihydro-6H- pyrrolo[3,4-b]pyridin-6-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate (Compound No. 159)

[0376] The titled compound (1.3 g, 2.69 mmol, 98 % yield) was prepared from ethyl 2-(ethylthio)-3-(5-oxo-2- (trifluoromethyl)-5,7-dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl) pyrazolo[l,5-a]pyrimidine-7- carboxylate (1.24 g, 2.75 mmol) using the procedure as mentioned in step-4 of the example-1. ’H-NMR (400 MHz, DMSO-J6) 5 9.24 (s, 1H), 9.17 (d, J = 5.1 Hz, 2H), 8.98 (d, J = 4.2 Hz, 1H), 8.30 (s, 1H), 7.82 (dd, J = 5.7, 4.5 Hz, 2H), 5.18 (s, 2H), 3.47 (q, J = 7.3 Hz, 2H), 1.21 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 490 (MH)+. ’H-NMR (400 MHz, DMSO-J6) 5 8.94 (d, J = 4.2 Hz, 1H), 8.57 (d, J = 8.1 Hz, 1H), 8.15 (d, J = 8.1 Hz, 1H), 7.86 (t, J = 4.2 Hz, 1H), 5.09 (d, J = 7.3 Hz, 2H), 4.52 (q, J = 7.1 Hz, 2H), 3.56-3.50 (m, 2H), 1.41-1.37 (m, 3H), 1.26 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 484.05 (MH)+.

[0377] Step-3: Synthesis of 2-(ethylsulfonyl)-3-(5-oxo-2-(trifluoromethyl)-5,7-dihydro-6H-pyrrolo[3,4- b]pyridin-6-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylic acid (Compound No. 160)

[0378] To an ice cooled solution of ethyl 2-(ethylsulfonyl)-3-(5-oxo-2-(trifluoromethyl)-5,7-dihydro-6H- pyrrolo[3,4-b]pyridin-6-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylate (1.1 g, 2.27 mmol) in tetrahydrofuran (10 mL), lithium hydroxide monohydrate (0.14 g, 3.41 mmol) in water (5 mL) was added. The resulting reaction mixture was warmed to 25 °C and stirred for 10 minutes. After the completion of the reaction, the resulting mixture was acidified to pH =1, using cone. HC1, to get a solid precipitate, which was filtered and dried under vacuum to obtain 2-(ethylsulfonyl)-3-(5-oxo-2- (trifluoromethyl)-5,7-dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylic acid (1.0 g, 2.196 mmol, 97 % yield). ’H-NMR (400 MHz, DMSO-J6) 5 8.91 (d, J = 4.2 Hz, 1H), 8.56 (d, J = 7.8 Hz, 1H), 8.15 (d, J = 7.8 Hz, 1H), 7.75 (d, J = 4.2 Hz, 1H), 5.08 (s, 2H), 3.51 (q, J = 7.3 Hz, 2H), 1.24 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 455.85 (MH)+.

[0379] Step-4: Synthesis of N-(2-cyanopropan-2-yl)-2-(ethylsulfonyl)-3-(5-oxo-2-(trifluoromethyl)-5,7- dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl)pyrazolo[l,5-a]pyrimidine-7-carboxamide (Compound No. 163)

[0380] To a stirred solution of 2-(ethylsulfonyl)-3-(5-oxo-2-(trifluoromethyl)-5,7-dihydro-6H-pyrrolo[3,4-b] pyridin-6-yl)pyrazolo[l,5-a]pyrimidine-7-carboxylic acid (180 mg, 0.395 mmol) in N,N- dimethylformamide (2 mb), pyridine (0.16 mb, 1.98 mmol), 2-amino-2 -methylpropanenitrile hydrochloride (95 mg, 0.79 mmol) and 1-propylphosphonic anhydride (0.36 mb, 0.59 mmol) were added sequentially at 25 °C. The resulting reaction mixture was stirred at 25 °C for 16 h. After the completion of the reaction, the mixture was quenched with water (25 mb). The precipitated solid product was fdtered, washed with water (100 mb) followed by 10% ethyl acetate in hexane (100 mb), and dried under vacuum to obtain N-(2-cyanopropan-2-yl)-2-(ethylsulfonyl)-3-(5-oxo-2- (trifluoromethyl)-5 ,7-dihydro-6H-pyrrolo[3 ,4-b]pyridin-6-yl)pyrazolo [ 1 ,5 -a]pyrimidine-7 - carboxamide (90 mg, 0.173 mmol, 43.7 % yield) ’H-NMR (400 MHz, DMSO-J6) 5 9.83 (s, 1H), 8.96 (d, J = 4.2 Hz, 1H), 8.57 (d, J = 7.8 Hz, 1H), 8.16 (d, J = 8.1 Hz, 1H), 7.78 (d, J = 4.2 Hz, 1H), 5.10 (s, 2H), 3.55 (q, J = 7.3 Hz, 2H), 1.76 (s, 6H), 1.29 (t, J = 7.3 Hz, 3H) ESI MS (m / z) 521.85 (MH)+.

[0381] Example-9: Synthesis of 6-(2-(ethylsulfonyl)-7-((l-methylcyclopropyl)amino)pyrazolo[l,5- a]pyrimidin-3-yl)-3-(trifluoromethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (Compound

[0382] No. 269)

[0383] Step-1: Synthesis of tert-butyl 3-((tert-butoxycarbonyl)amino)-2-(ethylthio)-7-oxopyrazolo[l,5- a] pyrimidine-4(7H)-carboxylate

[0384] To a stirred suspension of tert-butyl (2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidin-3- yl)carbamate (6.0 g, 19.33 mmol) in A. A-dimcthylfonnamidc (60 mb), sodium hydride (0.85 g, 21.26 mmol) and di-tert-butyl dicarbonate (4.90 mb, 21.26 mmol) were added in sequence and in portion wise at 0 °C under nitrogen atmosphere. The resulting reaction mixture was stirred at 25 °C for 1 h. After completion of the reaction, the reaction mixture was quenched with ice water (25 mb), and stirred for 10-15 minutes at the same temperature and obtained solid was filtered and dried under vacuum to obtain tert-butyl 3 -((tert-butoxycarbonyl)amino) -2-(ethylthio) -7 -oxopyrazolo [ 1 ,5 -a] pyrimidine -4(7H) - carboxylate (6 g, 14.62 mmol, 76 % yield) as an off-white solid. ’H-NMR (400 MHz, CHLOROFORM- D) 5 7.96 (d, J = 8.3 Hz, 1H), 6.26 (s, 1H), 5.91 (d, J = 8.3 Hz, 1H), 3.28-3.23 (m, 2H), 1.62 (s, 9H), 1.48-1.43 (m, 9H), 1.40-1.37 (m, 3H); ESI MS (m / z) 411.00 (MH)+.

[0385] Step-2: Synthesis of tert-butyl 3-((tert-butoxycarbonyl)((3-(methoxycarbonyl)-5-

[0386] (trifluoromethyl)pyridin-2-yl)methyl)amino)-2-(ethylthio)-7-oxopyrazolo[l,5-a]pyrimidine- 4(7H)-carboxylate

[0387] To a stirred solution of tert-butyl 3-((tert-butoxycarbonyl)amino)-2-(ethylthio)-7-oxopyrazolo[l,5- a]pyrimidine-4(7H)-carboxylate (6.5 g, 15.83 mmol) in A. A-dimcthylfonnamidc (50 mb), sodium hydride (1.267 g, 31.7 mmol) and methyl 2-(bromomethyl)-5-(trifhioromethyl)nicotinate (11.80 g, 15.83 mmol) were added sequentially at 0 °C. The resulting reaction mixture was warmed to 25 °C and stirred for Ih, at the same temperature. After completion of the reaction, the reaction mixture was poured into ice water ( 10 mL) . The aqueous layer was extracted with ethyl acetate (2 x15 mL) and the combined organic layers were dried over anhydrous sodium sulphate, filtered and evaporated to get a crude compound, which was purified by flash chromatography to obtain tert-butyl 3-((tert- butoxycarbonyl)((3-(methoxycarbonyl)-5-(trifluoromethyl)pyridin-2-yl)methyl)amino)-2-(ethylthio)- 7-oxopyrazolo[l,5-a]pyrimidine-4(7H)-carboxylate (7 g, 11.15 mmol, 70.4 % yield). ESI MS (m / z) 628.35 (MH)+.

[0388] Step-3: Synthesis of 2-(ethylthio)-3-(5-oxo-3-(trifluoromethyl)-5,7-dihydro-6H-pyrrolo[3,4- b]pyridin-6-yl)pyrazolo[l,5-a]pyrimidin-7(4H)-one

[0389] To an ice-cold solution of tert-butyl 3 -((tert-butoxycarbonyl) ((3 -(methoxy carbonyl) -5-

[0390] (trifluoromethyl)pyridin-2-yl)methyl)amino) -2-(ethylthio) -7 -oxopyrazolo [ 1 , 5 -a] pyrimidine -4(7H) - carboxylate (8.0 g, 12.75 mmol) in dichloromethane (100 mL), trifluoroacetic acid (9.82 mL, 127 mmol) was added dropwise over 10 minutes, at 0 °C. After complete addition, the reaction mixture was warmed to 25 °C and stirred for 12 h. After completion of the reaction, the reaction mixture was diluted with dichloromethane (200 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution (2 x 100 mL), saturated brine solution (200 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to get a crude compound 2-(ethylthio)-3-(5- oxo-3-(trifluoromethyl)-5,7-dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl)pyrazolo[l,5-a]pyrimidin-7(4H)- one (3.20 g, 8.09 mmol, 63.5 % yield) as a brown solid, which was used in the next step without any further purification. ESI MS (m / z) 396.05 (MH)+.

[0391] Step-4: Synthesis of 6-(7-chloro-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)-3-(trifluoromethyl)- 6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one To a stirred solution of 2-(ethylthio)-3-(5-oxo-3-(trifluoromethyl)-5,7-dihydro-6H-pyrrolo[3,4- b]pyridin-6-yl)pyrazolo[l,5-a]pyrimidin-7(4H)-one (2.5 g, 6.32 mmol) in acetonitrile (25 mL), POCI , (3.54 mL, 37.9 mmol) was added slowly and the resulting reaction mixture was stirred at 95 °C for 4 h. After completion of the reaction, the reaction mixture was cooled to 25 °C, and concentrated under reduced pressure. The residue was poured in to ice cold water (50 mL) and the aqueous layer was extracted with ethyl acetate (2 x 50 mL). The combined organic layers were washed with saturated brine solution (30 mL), dried over anhydrous sodium sulphate, filtered and evaporated to get a crude compound, which was purified by flash chromatography to obtain 6-(7-chloro-2- (ethyfthio)pyrazolo[l,5-a]pyrimidin-3-yl)-3-(trifluoromethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin- 5-one (1.6 g, 3.87 mmol, 61.1 % yield). ’H-NMR (400 MHz, CHLOROFORM- / )) 59.08-9.08 (m, 1H), 8.48 (d, J = 1.7 Hz, 1H), 8.35-8.33 (m, 1H), 6.96 (d, J = 4.5 Hz, 1H), 5.07 (s, 2H), 3.32-3.26 (m, 2H), 1.46-1.42 (m, 3H); ESI MS (m / z) 413.80 (MH)+.

[0392] Step-5: Synthesis of 6-(7-chloro-2-(ethylsulfonyl)pyrazolo[l,5-a]pyrimidin-3-yl)-3-

[0393] (trifluoromethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (Compound 240)

[0394] To an ice-cold solution of 6-(7-chloro-2-(ethyfthio)pyrazolo[l,5-a]pyrimidin-3-yl)-3-(trifluoromethyl)- 6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (500 mg, 1.21 mmol) in dichloromethane (20 mL), 3- chloroperoxybenzoic acid (695 mg, 2.417 mmol) was added and the reaction mixture was allowed to stir at 25 °C for 1 h. After completion of the reaction, the reaction mixture was diluted with dichloromethane (200 mL). The organic layer was washed with saturated sodium thiosulfate solution (150 mL), saturated sodium bicarbonate solution (2 x 100 mL), dried over anhydrous sodium sulfate, filtered and evaporated to get a crude compound. The crude product was triturated with diethyl ether, and the resulted solid was filtered, dried under vacuum to obtain 6-(7-chloro-2- (ethylsulfonyl)pyrazolo[ 1 ,5 -a]pyrimidin-3 -y 1) -3 -(trifluoromethyl)-6,7-dihydro-5H-pyrrolo [3 ,4- b]pyridin-5-one (430 mg, 0.965 mmol, 80 % yield) as a desired product. ’H-NMR (400 MHz, CHLOROFORM- / )) 5 9.11 (d, J = 1.2 Hz, 1H), 8.58 (d, J = 4.4 Hz, 1H), 8.47 (d, J = 1.6 Hz, 1H), 7.31 (d, J = 4.4 Hz, 1H), 5.14 (s, 2H), 3.57 (q, J = 7.4 Hz, 2H), 1.47 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 445.80 (MH)+.

[0395] Step-6: Synthesis of 6-(2-(ethylsulfonyl)-7-((l-methylcyclopropyl)amino)pyrazolo[l,5- a]pyrimidin-3-yl)-3-(trifluoromethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (Compound No. 269)

[0396] To a stirred solution of 6-(7-chloro-2-(ethylsulfonyl)pyrazolo[l,5-a]pyrimidin-3-yl)-3- (trifluoromethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (120 mg, 0.27 mmol) in N,N- dimethylformamide (2 mL), 1-methylcyclopropan-l -amine hydrochloride (87 mg, 0.808 mmol) and triethylamine (0.12 mL, 0.81 mmol) were added in sequence, and the resulting reaction mixture was stirred at 25 °C for 1 h. After completion of the reaction, the reaction mixture was diluted with water (25 mL). The aqueous layer was extracted with ethyl acetate (2 x 25 mL) and the combined organic layers were dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain a crude compound which was purified by flash column chromatography to obtain 6-(2- (ethylsulfonyl)-7 -(( 1 -methylcyclopropyl)amino)pyrazolo [1,5 -a]pyrimidin-3 -y 1) -3 -(trifluoromethyl) - 6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (70 mg, 0.146 mmol, 54.1 % yield). ’H-NMR (400 MHz, CHLOROFORM- / )) 5 9.08 (s, 1H), 8.44 (d, J = 2.0 Hz, 1H), 8.38 (d, J = 5.1 Hz, 1H), 6.99 (d, J = 6.6 Hz, 1H), 6.51 (d, J = 5.1 Hz, 1H), 5.09 (s, 2H), 3.51 (q, J = 7.4 Hz, 2H), 3.11 (s, OH), 1.53 (s, 3H), 1.44 (t, J = 7.5 Hz, 3H), 1.06-1.03 (m, 2H), 0.94-0.91 (m, 2H); ESI MS (m / z) 480.80 (MH)+.

[0397] Example-10: Synthesis of tert-butyl (2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidin-3- yl)carbamate

[0398] Step-1: Synthesis of ethyl 2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-3- carboxylate

[0399] A mixture of ethyl 5-amino-3-(ethylthio)-lH-pyrazole-4-carboxylate (30 g, 139 mmol) and methyl 3,3- dimethoxypropanoate (23.71 mL, 167 mmol) in acetic acid (200 mL) was heated at 110 °C for 18 h. After completion of the reaction, the reaction mixture was cooled to 25 °C, and solvents were removed under reduced pressure. The residue was diluted with ice-cold water (IL) and the resulted light-yellow precipitate was filtered and washed with water (1000 mL) followed by hexane (200 mL) and dried under vacuum to obtain ethyl 2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-3-carboxylate (35 g, 131 mmol, 94 % yield).1H-NMR (400 MHz, CHLOROFORM- / )) 5 10.01 (s, 1H), 7.56-7.52 (m, 1H), 6.05 (d, J = 6.1 Hz, 1H), 4.44-4.37 (m, 2H), 3.34 (q, J = 7.4 Hz, 2H), 1.49-1.35 (m, 6H); ESI MS (m / z) 267.80 (MH)+.

[0400] Step-2: Synthesis of 2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-3-carboxylic acid

[0401] To a stirred solution of ethyl 2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-3-carboxylate (30 g, 112 mmol) in ethanol (250 mL), sodium hydroxide (44.9 g, 1122 mmol) in water (250 mL) was added at 25 °C. The resulted reaction mixture was stirred at 70 °C for 16 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and evaporated the solvents under reduced pressure. The residue was acidified with cone. HC1 (pH= 1), and the precipitated solid was filtered, washed with 50% ethyl acetate in hexane (200 mL) and dried under vacuum to obtain 2-(ethylthio)-7-oxo-4,7- dihydropyrazolo[l,5-a]pyrimidine-3-carboxylic acid (22 g, 92 mmol, 82 % yield). ESI MS (m / z) 239.80 (MH)+.

[0402] Step-3: Synthesis of 2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-3-carbonyl azide To a stirred solution of 2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-3-carboxylic acid (15 g, 62.7 mmol) and triethylamine (8.75 mL, 62.7 mmol) in acetonitrile (300 mL), diphenyl phosphoryl azide (13.48 mL, 62.7 mmol) was added slowly at 25 °C, and the resulting mixture was stirred at 25 °C for 14 h. After completion of the reaction, the reaction mixture was diluted with dichloromethane (500 mL) and washed with aqueous sodium bicarbonate solution (250 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated (below 30 °C) to obtain crude 2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-3-carbonyl azide (12 g, 45.4 mmol, 72.4 % yield), which was used in the next reaction as it is. ESI MS (m / z) 264.80 (MH)+.

[0403] Step-4: Synthesis of tert-butyl (2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidin-3- yl)carbamate

[0404] A solution of 2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-3-carbonyl azide (12 g, 45.4 mmol) in tert-butanol (130 mL, 1362 mmol) was heated at 95 °C for 8 h. After completion of the reaction, the reaction mixture was cooled to 25 °C, and concentrated under reduced pressure to get a crude compound which was purified by flash chromatography to obtain tert-butyl (2-(ethylthio)-7-oxo- 4,7-dihydropyrazolo[l,5-a]pyrimidin-3-yl)carbamate (3.2 g, 10.31 mmol, 22.71 % yield). ESI MS (m / z) 311.00 (MH)+.

[0405] Example-11: Synthesis of 6-(7-(3,5-difluorophenyl)-2-(ethylsulfonyl)pyrazolo[l,5-a]pyrimidin-3- yl)-3-(trifluoromethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (Compound No. 298)

[0406] Step-1: Synthesis of 6-(7-(3,5-difluorophenyl)-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)-3- (trifluoromethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

[0407] To a stirred solution of 6-(5-amino-3-(ethylthio)-lH-pyrazol-4-yl)-3-(trifluoromethyl)-6,7-dihydro-5H- pyrrolo[3,4-b]pyridin-5-one (500 mg, 1.456 mmol) (Example-7 : Step-4) in acetic acid (10 mL), under nitrogen atmosphere, l-(3,5-difluorophenyl)-3-(dimethylamino)prop-2-en-l-one (461 mg, 2.184 mmol) (J. Org. Chem. 2024, 89, 15, 10538) was added at 25 °C. The resulting reaction mixture was heated to 110 °C for 2 h. After completion of the reaction, the reaction mixture was cooled to 25 °C, and solvents were evaporated to dryness. The residue was dissolved in ethyl acetate (100 mL), washed with saturated brine solution (2 x 150 mL), dried over anhydrous sodium sulfate, filtered and evaporated to get a crude compound which was purified using flash column chromatography to obtain 6-(7-(3,5- difluorophenyl)-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)-3-(trifluoromethyl)-6,7-dihydro-5H- pyrrolo[3,4-b]pyridin-5-one (390 mg, 0.794 mmol, 54.5 % yield) as a brown solid.1H-NMR (400 MHz, CHLOROFORM- / )) 5 9.09 (s, 1H), 8.52-8.50 (m, 2H), 7.71-7.66 (m, 2H), 7.07 (tt, J = 8.6, 2.3 Hz, 1H), 6.93 (d, J = 4.4 Hz, 1H), 5.12 (d, J = 15.6 Hz, 2H), 3.26-3.19 (m, 2H), 1.43 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 492.20 (MH)+.

[0408] Step-2 : Synthesis of 6-(7-(3,5-difluorophenyl)-2-(ethylsulf onyl)pyrazolo [1 ,5-a] pyrimidin-3-yl)-3- (trifluoromethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (Compound 298)

[0409] The titled compound (95 mg, 0.181 mmol, 59.5 % yield) was prepared from 6-(7-(3,5-difluorophenyl)- 2-(ethylthio)pyrazolo [1,5 -a]pyrimidin-3 -y 1) -3 -(trifluoromethyl)-6,7-dihydro-5H-pyrrolo [3,4- b]pyridin-5-one (150 mg, 0.305 mmol) using the procedure as mentioned in step-4 of the example-1. ’H-NMR (400 MHz, CHLOROFORM- / )) 5 9.11 (s, 1H), 8.74 (d, J = 4.4 Hz, 1H), 8.48 (s, 1H), 7.64- 7.62 (m, 2H), 7.23 (d, J = 4.2 Hz, 1H), 7.14-7.09 (m, 1H), 5.16 (s, 2H), 3.53 (q, J = 7.5 Hz, 2H), 1.46 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 523.90 (MH)+.

[0410] Example-12: Synthesis of N-(2-(ethylsulfonyl)-3-(l-oxo-6-(trifluoromethyl)-l,3-dihydro-2H- pyrrolo[3,4-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidin-7-yl)isobutyramide (Compound No. 68)

[0411] Step-1: Synthesis of methyl 5-(((tert-butoxycarbonyl) (7-(tert-butylamino)-2-

[0412] (ethylthio)pyrazolo[l,5-a]pyridin-3-yl)amino)methyl)-2-(trifluoromethyl)isonicotinate

[0413] To a stirred solution of tert-butyl (7-(tert-butylamino)-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3- yl)carbamate (6.54 g, 17.89 mmol) in acetonitrile (70 mL), CS2CO3 (14.58 g, 44.7 mmol) and methyl 5-(bromomethyl)-2-(trifluoromethyl)isonicotinate (8.0 g, 26.8 mmol) were added sequentially at 25 °C. The resulting reaction mixture was heated at 55 °C for 14 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and poured into ice water (200 mL). The aqueous layer was extracted with ethyl acetate (2 x 150 mL) and the combined organic layers were dried over anhydrous sodium sulphate, filtered and evaporated to get a crude compound which was purified by flash chromatography to obtain methyl 5 -(((tert-butoxy carbonyl) (7-(tert-butylamino)-2-

[0414] (ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)amino)methyl)-2-(trifluoromethyl)isonicotinate (6.5 g, 11.16 mmol, 62.3 % yield). ESI MS (m / z) 583.50 (MH)+.

[0415] Step-2: Synthesis of 2-(7-(tert-butylamino)-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)-6- (trifluoromethyl)-2,3-dihydro-lH-pyrrolo[3,4-c]pyridin-l-one

[0416] To an ice-cold solution of methyl 5-(((tert-butoxycarbonyl)(7-(tert-butylamino)-2- (ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)amino)methyl)-2-(trifluoromethyl)isonicotinate (6.0 g, 10.30 mmol) in dichloromethane (60 mL), trifluoroacetic acid (7.93 mL, 103 mmol) was added dropwise at 25 °C. The resulting reaction mixture was stirred at 50 °C for 12 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and diluted with dichloromethane (200 mL). The organic layer was washed with saturated NaHCCL solution (2 x 150 mL), saturated brine solution (200 mL), dried over anhydrous sodium sulphate, filtered and evaporated to get a crude compound which was purified by flash chromatography to obtain 2-(7-(tert-butylamino)-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)- 6-(trifluoromethyl)-2,3-dihydro-lH-pyrrolo[3,4-c]pyridin-l-one (4.1 g, 9.10 mmol, 88 % yield).1H- NMR (400 MHz, CHLOROFORM- / )) 5 8.98 (s, 1H), 8.22 (d, J = 1.0 Hz, 1H), 8.15 (d, J = 5.9 Hz, 1H), 6.73 (s, 1H), 6.20 (d, J = 5.9 Hz, 1H), 5.11 (s, 2H), 3.18 (q, J = 7.4 Hz, 2H), 1.59-1.56 (m, 9H), 1.42- 1.38 (m, 3H); ESI MS (m / z) 450.95 (MH)+.

[0417] Step-3: Synthesis of 2-(7-amino-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)- 2,3-dihydro-lH-pyrrolo[3,4-c]pyridin-l-one

[0418] To a stirred solution of 2-(7-(tert-butylamino)-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)-6- (trifluoromethyl)-2,3-dihydro-lH-pyrrolo[3,4-c]pyridin-l-one (4.0 g, 8.88 mmol) in MeOH (20 mL), Cone. HC1 (82 mL, 888 mmol) was added at 25 °C dropwise over 5 minutes. The resulting reaction mixture was allowed to stir at 120 °C for 12 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and concentrated under reduced pressure to get a residue. The residue was diluted with ethyl acetate (200 mL) and the organic layer was washed with saturated NaHCCL solution (2 x 150 mL), saturated brine solution (200 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to get a crude compound which was purified by flash chromatography to obtain 2-(7-amino-2-(ethylthio)pyrazolo[l, 5-a]pyrimidin-3-yl)-6-(trifluoromethyl)- 2,3-dihydro-lH-pyrrolo[3,4-c]pyridin-l-one (3.1 g, 7.86 mmol, 89 % yield) as a solid. ’H-NMR (400 MHz, DMSO-J6) 5 9.15 (s, 1H), 8.22 (d, J = 1.0 Hz, 1H), 8.04 (d, J = 5.1 Hz, 1H), 7.95 (s, 2H), 6.15 (d, J = 5.1 Hz, 1H), 5.08 (s, 2H), 3.13 (q, J = 7.3 Hz, 2H), 1.29 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 395.05 (MH)+.

[0419] Step-4: Synthesis of 2-(7-amino-2-(ethylsulfonyl)pyrazolo[l,5-a]pyrimidin-3-yl)-6-

[0420] (trifluoromethyl)-2,3-dihydro-lH-pyrrolo[3,4-c]pyridin-l-one (Compound 61)

[0421] The titled compound (1.7 g, 3.99 mmol, 79 % yield) was prepared from 2-(7-amino-2- (ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)-2,3-dihydro-lH-pyrrolo[3,4-c]pyridin- l-one (2.0 g, 5.07 mmol) using the procedure as mentioned in step-4 of the example-1. ’H-NMR (400 MHz, DMSO-J6) 5 9.19 (s, 1H), 8.36 (s, 2H), 8.25-8.23 (m, 2H), 6.39 (d, J = 5.4 Hz, 1H), 5.08 (s, 2H), 3.50 (q, J = 7.4 Hz, 2H), 1.24 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 427.05 (MH)+.

[0422] Step-5: Synthesis of N-(2-(ethylsulfonyl)-3-(l-oxo-6-(trifluoromethyl)-l,3-dihydro-2H- pyrrolo[3,4-c]pyridin-2-yl)pyrazolo[l,5-a]pyrimidin-7-yl)isobutyramide (Compound 68) To a stirred solution of 2-(7-amino-2-(ethylsulfonyl)pyrazolo[l,5-a]pyrimidin-3-yl)-6- (trifluoromethyl)-2,3-dihydro-lH-pyrrolo[3,4-c]pyridin-l-one (200 mg, 0.469 mmol) in dichloromethane (10 mL), triethylamine (0.20 mL, 1.407 mmol) was added at 0 °C and stirred for 10 minutes. Then isobutyryl chloride (75.0 mg, 0.704 mmol) was added to the above reaction mixture at 0 °C and the resulting reaction mixture was stirred at 25 °C for 3 h. After completion of the reaction, the reaction mixture was added to brine solution (2 x 50 mL). The aqueous layer was extracted with dichloromethane (2 x 50 mL) and the combined organic layers were dried over anhydrous Na2SC>4, filtered and evaporated to get a crude compound which was purified by flash column chromatography to obtain N-(2-(ethylsulfonyl)-3-(l-oxo-6-(trifluoromethyl)-l,3-dihydro-2H-pyrrolo[3,4-c]pyridin-2- yl)pyrazolo[l,5-a]pyrimidin-7-yl)isobutyramide (105 mg, 0.211 mmol, 45.1 % yield) as off white solid. ’H-NMR (400 MHz, DMSCM,) 5 11.13 (s, 1H), 9.21 (s, 1H), 8.68 (d, J = 5.1 Hz, 1H), 8.28 (d, J = 1.0 Hz, 1H), 7.95 (d, J = 4.9 Hz, 1H), 5.12 (s, 2H), 3.58 (q, J = 7.4 Hz, 2H), 3.26 (m, J = 6.8 Hz, 1H), 1.27- 1.23 (t, 3H), 1.18 (d, J = 6.8 Hz, 6H); ESI MS (m / z) 497.15 (MH)+.

[0423] Example-13: Synthesis of tert-butyl (7-(tert-butylamino)-2-(ethylthio)pyrazolo[l,5-a]pyrimidin- 3-yl)carbamate

[0424] Step-1: Synthesis of ethyl 7-chloro-2-(ethylthio)pyrazolo[l,5-a]pyrimidine-3-carboxylate

[0425] To a stirred solution of ethyl 2-(ethylthio)-7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-3-carboxylate (12.5 g, 46.8 mmol) (Example 10: Step-1) in acetonitrile (120 mL), POCL (21.79 mL, 234 mmol) was added slowly and the resulting reaction mixture was heated at 95 °C for 6 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and concentrated under reduced pressure. The residue was poured into ice water (200 mL) and the aqueous layer was extracted with ethyl acetate (2 x 150 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 get a crude compound which was purified by flash column chromatography to obtain ethyl 7 -chloro-2-(ethylthio)pyrazolo [1,5- a] pyrimidine -3 -carboxylate (11.0 g, 38.5 mmol, 82 % yield). ’H-NMR (400 MHz, CHLOROLORM- D) 5 8.55 (d, J = 4.6 Hz, 1H), 7.02 (d, J = 4.6 Hz, 1H), 4.47 (q, J = 7.1 Hz, 2H), 3.29 (q, J = 7.3 Hz, 2H), 1.48 (t, J = 7.3 Hz, 3H), 1.44 (t, J = 7.2 Hz, 3H); ESI MS (m / z) 286.00 (MH)+.

[0426] Step-2: Synthesis of ethyl 7-(tert-butylamino)-2-(ethylthio)pyrazolo[l,5-a]pyrimidine-3- carboxylate

[0427] To an ice cooled solution of ethyl 7-chloro-2-(ethylthio)pyrazolo[l, 5 -a]pyrimidine-3 -carboxylate (21.5 g, 75 mmol) in A. A-dimcthylfonnamidc (200 mL), 2-methylpropan-2 -amine (23.72 mL, 226 mmol) was added at 0 °C and the reaction mixture was stirred at 25 °C for 4 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (300 mL). Organic layer was washed with cold water (2 x 200 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain ethyl 7-(tert-butylamino)-2-(ethylthio)pyrazolo[l,5-a]pyrimidine-3-carboxylate (23.5 g, 72.9 mmol, 97 % yield), which was used in the next step without any further purification. ’H-NMR (400 MHz, CHLOROFORM- / )) 5 8.33 (d, J = 5.5 Hz, 1H), 6.56 (s, 1H), 6.21 (d, J = 5.5 Hz, 1H), 4.46 (q, J = 7.1 Hz, 2H), 3.21 (q, J = 7.4 Hz, 2H), 1.56 (s, 9H), 1.48-1.41 (m, 6H); ESI MS (m / z) 323.25 (MH)+.

[0428] Step-3: Synthesis of 7-(tert-butylamino)-2-(ethylthio)pyrazolo[l,5-a]pyrimidine-3-carboxylic acid

[0429] To a stirred solution of ethyl 7-(tert-butylamino)-2-(ethylthio)pyrazolo[l,5-a]pyrimidine-3-carboxylate (23.0 g, 71.3 mmol) in ethanol (150 mL), lithium hydroxide monohydrate (23.95 g, 571 mmol) in water (150 mL) was added at 25 °C and the reaction mixture was stirred at 60 °C for 6 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and concentrated under reduced pressure to obtain a residue which was acidified with cone. HC1 (pH= 1) and the obtained solid was filtered and dried under vacuum to obtain 7-(tert-butylamino)-2-(ethylthio)pyrazolo[l, 5 -a]pyrimidine-3 -carboxylic acid (18.2 g, 61.8 mmol, 87 % yield).1H-NMR (400 MHz, DMSO-J6) 5 11.97 (d, J = 33.7 Hz, 1H), 8.21 (d, J = 5.6 Hz, 1H), 6.79 (s, 1H), 6.59 (d, J = 5.6 Hz, 1H), 3.19 (q, J = 7.3 Hz, 2H), 1.47 (d, J = 20.3 Hz, 9H), 1.35 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 294.95 (MH)+.

[0430] Step-4: Synthesis of tert-butyl (7-(tert-butylamino)-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3- yl)carbamate

[0431] A solution of 7-(tert-butylamino)-2-(ethylthio)pyrazolo[l,5-a]pyrimidine-3-carboxylic acid (18.0 g, 61.1 mmol) and triethylamine (13.64 mL, 98 mmol) in tert-butanol (175 mL, 1834 mmol) was heated to 90 °C. At this temperature, diphenyl phosphoryl azide (21.03 mL, 98 mmol) was added dropwise for 10 minutes and the resulting reaction mixture was continued to stir at 90 °C for 3 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and poured into ice water (300 mL). The aqueous layer was extracted with ethyl acetate (2 x 150 mL) and the combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to get a crude compound which was purified by flash column chromatography to obtain tert-butyl (7-(tert- butylamino)-2-(ethylthio)pyrazolo[l,5-a]pyrimidin-3-yl)carbamate (14.0 g, 38.3 mmol, 62.6 % yield). ‘H-NMR (400 MHz, CHLOROFORM -D) 5 8.13 (d, J = 5.5 Hz, 1H), 6.61 (s, 1H), 6.18 (d, J = 5.5 Hz, 1H), 6.08 (d, J = 5.5 Hz, 1H), 3.17-3.12 (m, 2H), 1.56 (dd, J = 6.7, 1.8 Hz, 9H), 1.50-1.42 (m, 9H), 1.39 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 366.15 (MH)+.

[0432] Example-14: Synthesis of N-(ethyl(oxo)(3-(l-oxo-6-(trifluoromethyl)-l,3-dihydro-2H- pyrrolo[3,4-c]pyridin-2-yl)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidin-2-yl)-X6-sulfaneylidene)- 2,2,2-trifluoroacetamide (Compound No. 56)

[0433] Step-1: Synthesis of 2-(2-(ethylsulfonimidoyl)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidin-3-yl)- 6-(trifluoromethyl)-2,3-dihydro-lH-pyrrolo[3,4-c]pyridin-l-one (Compound No. 55)

[0434] To a stirred solution of 2-(2-(ethylthio)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidin-3-yl)-6- (trifluoromethyl)-2,3-dihydro-lH-pyrrolo[3,4-c]pyridin-l-one (450 mg, 0.984 mmol) (Example-3: Step-3) in MeOH (15 mL), iodobenzene diacetate (634 mg, 1.967 mmol) was added at 0 °C. Then ammonium carbamate (384 mg, 4.92 mmol) was added in portions to the above reaction mixture, at 0 °C and stirred for additional 10 minutes at the same temperature. Then the reaction mixture was stirred at 25 °C for 16 h. After completion of the reaction, solvents were evaporated and the crude product was purified by flash column chromatography to obtain 2-(2-(ethylsulfonimidoyl)-7-(pyrimidin-2- yl)pyrazolo[l,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)-2,3-dihydro-lH-pyrrolo[3,4-c]pyridin-l-one (350 mg, 0.717 mmol, 72.8 % yield) as a pale-yellow solid. ’H-NMR (400 MHz, DMSO-t / e) 5 9.23 (s, 1H), 9.16 (d, J = 4.9 Hz, 2H), 8.94-8.91 (m, 1H), 8.28 (s, 1H), 7.81 (t, J = 5.0 Hz, 1H), 7.72 (d, J = 4.2 Hz, 1H), 5.20 (s, 2H), 3.30-3.26 (q, 2H), 1.18 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 488.85 (MH)+.

[0435] Step-2: Synthesis of N-(ethyl(oxo)(3-(l-oxo-6-(trifluoromethyl)-l,3-dihydro-2H-pyrrolo[3,4- c]pyridin-2-yl)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidin-2-yl)-X6-sulfaneylidene)-2,2,2- trifluoroacetamide (Compound No. 56)

[0436] To an ice cooled solution of 2-(2-(ethylsulfonimidoyl)-7-(pyrimidin-2-yl)pyrazolo[l,5-a]pyrimidin-3- yl)-6-(trifluoromethyl)-2,3-dihydro-lH-pyrrolo[3,4-c]pyridin-l-one (170 mg, 0.348 mmol) in N,N- dimethylformamide (5 mL), A. A-diisopropylcthylaminc (0.24 mL, 1.392 mmol) was added and stirred for 10 minutes at 0 °C. Trifluoroacetic anhydride (0.194 mL, 1.392 mmol) was added dropwise to the reaction mixture and stirred for an additional 10 minutes at 0 °C. The resulting reaction mixture was stirred at 25 °C for 3 h. After completion of the reaction, the reaction mixture was added to saturated brine solution (2 x 100 mL). The aqueous layer was extracted with ethyl acetate (2 x 100 mL) and the combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated to get a crude compound which was purified by flash column chromatography to obtain N-(ethyl(oxo)(3-(l- oxo-6-(trifluoromethyl)-l,3-dihydro-2H-pyrrolo[3,4-c]pyridin-2-yl)-7-(pyrimidin-2-yl)pyrazolo[l,5- a]pyrimidin-2-yl)-X6-sulfaneylidene)-2,2,2-trifluoroacetamide (70 mg, 0.120 mmol, 34.4 % yield) as a yellow solid. ’H-NMR (400 MHz, DMSO-J6) 5 9.26 (s, 1H), 9.14 (d, J = 4.9 Hz, 2H), 9.04 (d, J = 4.3 Hz, 1H), 8.31 (d, J = 0.9 Hz, 1H), 7.89 (d, J = 4.3 Hz, 1H), 7.81 (t, J = 4.9 Hz, 1H), 5.29 (s, J = 18.3 Hz, 1H), 5.16 (s, J = 18.6 Hz, 1H), 4.08-3.98 (q, 2H), 1.33 (t, J = 7.2 Hz, 3H); ESI MS (m / z) 585 (MH)+. Table A: The following compounds in Table A were synthesized using analogous procedures as described in the schemes 1-12 or in the chemistry examples.

[0437] * Compound names generated using Chemdraw Professional 19.1

[0438] In one embodiment, the present invention provides a composition for controlling or preventing invertebrate pests. The composition comprises a biologically effective amount of the compounds of formula (I) and at least one additional component selected from the group consisting of surfactants and auxiliaries.

[0439] In yet another embodiment, the present invention provides compounds 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 compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6thEd. May 2008, CropLife International.

[0440] The compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T and F Informa, London, 2005.

[0441] In one another embodiment, the present invention provides an agrochemical composition comprising compounds 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).

[0442] 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 in a range of 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready -to-use preparations. The application can be carried out before or during sowing.

[0443] Methods for applying or treating compounds of formula (I) and compositions thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, compounds of formula (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.

[0444] 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.

[0445] In the 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.

[0446] 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.

[0447] 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.

[0448] 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 liters, more preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.

[0449] 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.

[0450] 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.

[0451] In the context of the present invention "invertebrate pest control" means inhibition of invertebrate pest development (including mortality) that causes a 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.

[0452] 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 (C6 stoda). Those skilled in the art will recognize that not all compounds are equally effective against all pests.

[0453] 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 (Spodopiera fugiperda J. E. Smith), beet armyworm (Spodopiera exigua Hubner), black cutworm (Agrolis ipsilon Hufhagel), cabbage looper (Trichoplusia ni Hubner), tobacco budworm (Heliothis virescens Fabricius)); borers, casebearers, webworms, coneworms, cabbageworms and skeletonizers from the family Pyralidae (e.g., European com borer (Ostrinia nubilalis Hubner), navel orangeworm (Amyelois Iransiledla WAker). com root webworm (Crambus caliginosellus Clemens), sod webworm (Herpetogramma licarsisalis Walker)); leafrohers, budworms, seed worms, and fmit 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 gemnanicci Linnaeus), brownbanded cockroach (Supella longipalpci Fabricius), American cockroach (Periplaneta americcinci Linnaeus), brown cockroach (Periplaneta brunnea Burmeister), Madeira cockroach (Leucophaea madercie 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 grancirius 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 com rootworm (Diabroticci virgifera virgifera LeConte)); chafers and other beetles from the family Scaribaeidae (e.g., Japanese beetle (Popillici japonicci 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 auriculcirici 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, whiteflies 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 C6rcopidae 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 (Pcmonychus 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 leafininers, 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 (Lasius alienus Forster), 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 (ReiicuUiermes hesperus Banks), Formosan subterranean termite (Copioiermes formosanus Shiraki), West Indian drywood termite (Incisitermes immigrans Snyder) and other termites of economic importance; insect pests of the order Thysanura such as silverfish (he pis ma 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 (CienocephaUdes 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, C6stoda, 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.).

[0454] 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 (com root webworm), Crambus teterrellus Zincken (bluegrass webworm), Cydia pomonella Linnaeus (codling moth), Earias insulana Boisduval (spiny bollworm), Earias vittella Fabricius (spotted bollworm), Helicoveipa armigera Hubner (American bollworm), Helicoverpa zea Boddie (com earworm), Heliothis virescens Fabricius (tobacco budworm), Herpetogramma licarsisalis Walker (sod webworm), Lobesia botrana Denis and Schiffeimuller (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)).

[0455] 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 Geoffrey (mealy plum aphid), Lipaphis erysimi Kaltenbach (tamip 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 (com 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 auraniii. 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 nigropictus Stal (rice leafhopper), Nilaparvata lugens Stal (brown planthopper), Peregrinus maidis Ashmead (com planthopper), Sogatella furcifera Horvath (white- backed planthopper), Sogatodes orizicola Muir (rice delphacid), Typhlocyba pomarici 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), Trioza diospyri Ashmead (persimmon psylla).

[0456] 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), Oehalus pugnax Fabricius (rice stink bug), Oncopeltus fasciatus DaEas (large milkweed bug), Pseudatomoscelis seriatus Reuter (cotton fleahopper).

[0457] Other insect which are controlled by compounds of formula (I) of the present invention include: Thysanoptera (e.g., Frankliniella occidentalis Pergande (western flower thrip), Scirthothrjps citri Moulton (citrus thrip), Sericothrips variahilis Beach (soybean thrip), and Thrips tahaci 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).

[0458] 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, Phalerci bucephalci, Phthorimaeci 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

[0459] Beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, 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 californicus, 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, Popillia japonica, 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 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; termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes gras sei, 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 orientalis; 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. Ctenocephalides felis, 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.

[0460] 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.

[0461] 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.

[0462] In one embodiment of the present invention, the present invention provides the compounds 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:

[0463] Thysanoptera: Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,

[0464] Diptera: 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 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;

[0465] 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 horni, 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.

[0466] In a preferred embodiment, the present invention provides compounds of formula (I) or compositions or combinations comprising compounds of formula (I), which are effective against pest including: Lepidopteran pests, including but not limited to: Spodoptera spp. (e.g., .S' litura, S. frugiperda)'. Pluiella xylostella (diamondback moth), Helicoverpa armigera. Stem borers (e.g., Scirpophaga inceriidas)'. leaf folders, leaf rollers, leaf miners, and loopers. Hemipteran pests, including but not limited to: Myzus persicae (Aphids), Amrasca biguttula biguttula (jassids), Bemisia tabaci (whiteflies), Nilaparvata lugens (brown plant hoppers).

[0467] Thysanopteran pests, such as Thrips spp., Acarine pests, including mites, Coleopteran pests, including weevils and beetles, and soil insects.

[0468] In one embodiment, the present invention provides a composition comprising a biologically effective amount of the compounds 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.

[0469] In another embodiment, the present invention provides a combination 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 biological active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers or nutrients.

[0470] The compounds used in the composition and in combination with the compounds of formula (I) are also termed as active compatible compounds.

[0471] The known and reported fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics and nutrients can be combined with at least one compounds 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 compounds of formula (I) of the present disclosure.

[0472] 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 compounds of the formula (I) of the present disclosure.

[0473] Particularly, the compounds of the present invention can be mixed with at least one additional biological active compatible compounds (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.

[0474] Examples of such biologically active compounds or agents / mixing partners with which compounds of formula (I) of the present invention can be combined / formulated are disclosed in the W02019072906A1 (page 27 to 37).

[0475] 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.

[0476] 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 compound or agent 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.

[0477] In one embodiment of the present invention, the compounds of formula (I), or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof in the composition 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.

[0478] 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.

[0479] 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.

[0480] 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 butoxide often enhance compound efficacy.

[0481] 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.

[0482] 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).

[0483] 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.

[0484] 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.

[0485] 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, composition or combination thereof according to the present invention. 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 (1) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof, composition or combination thereof according to the present invention.

[0486] 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, or combination thereof according to the present invention, for combating insects and mite pests in agricultural crops, horticultural crops, household and vector control and parasites on animals.

[0487] In yet another embodiment, the present invention provides a seed comprising a compound of formula (I) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof, composition or combination thereof according to the present invention, wherein the amount of compound of formula (I) in said seed ranging from about 0.0001 % to about 1 % by weight.

[0488] 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.

[0489] 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.

[0490] 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.

[0491] 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 500 g per hectare, more preferably from 50 g to 250 g per hectare.

[0492] 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 com), 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.

[0493] Particularly, the compound or the composition of the present invention are useful in protecting agricultural crops such as cereals, com, 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.

[0494] The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development.

[0495] Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post -translational modification of protein(s), oligo or polypeptides for example, by glycosylation or polymer additions such as prenylated, acetylated or famesylated moieties or PEG moieties.

[0496] Plants that have been modified by breeding, mutagenesis or genetic engineering, for example, have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxylphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are e. g. described in Pest Managem. Sci. 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), for example Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, for example imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, for example tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, com, beets and rape, tolerant to herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate- tolerant, Bayer CropScience, Germany).

[0497] Furthermore, plants capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus (Bacillus), by the use of recombinant DNA techniques are within the scope of the present invention. The Bacillus are particularly from Bacillus thuringiensis, such as b-cndotoxins. e.g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect -specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre- toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. W002 / 015701). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, for example, in EP0374753, WO93 / 007278, WO95 / 34656, EP0427529, EP0451878, W003 / 18810 and W003 / 52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants, producing these proteins, tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (com cultivars producing the CrylAb toxin), YieldGard® Plus (com cultivars producing CrylAb and Cry3Bbl toxins), Starlink® (com cultivars producing the Cry9c toxin), Herculex® RW (com cultivars producing Cry34Abl, Cry35Abl and the enzyme phosphinothricin-A-acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the CrylAc toxin), Bollgard® I (cotton cultivars producing the Cryl Ac toxin), Bollgard® II (coton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT® (coton cultivars producing a VIP- toxin); NewLeaf®(potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Btl 1 (e. g. Agrisure® CB) and Btl76 from Syngenta Seeds SAS, France, (com cultivars producing the CrylAb toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (com cultivars producing a modified version of the Cry3A toxin, c.f. WO 03 / 018810), MON 863 from Monsanto Europe S.A., Belgium (com cultivars producing the Cry3Bb 1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (coton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (com cultivars producing the Cryl F toxin and PAT enzyme); Btl 1 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified Zea mays which has been rendered resistant to atack by the European com borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a tmncated CrylAb toxin. Btl 1 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium; Btl 76 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified Zea mays which has been rendered resistant to atack by the European com borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a CrylAb toxin. Btl76 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium; MIR604 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G- protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03 / 018810; MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses a Cry3Bbl toxin and has resistance to certain Coleoptera insects; IPC 531 Coton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02; 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-l 160 Bmssels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize for the expression of the protein Cryl F for achieving resistance to certain Lepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium; and NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 x MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a Cryl Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European com borer.

[0498] Furthermore, plants capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens by the use of recombinant DNA techniques are also within the scope of the present invention. Examples of such proteins are the so-called "pathogenesis-related proteins" (PR proteins, see, for example EP0392225), plant disease resistance genes (e.g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato Solcinum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.

[0499] Furthermore, plants capable to synthesize one or more proteins, by the use of recombinant DNA techniques, to increase the productivity (e. g. biomass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants are within the scope of the present invention.

[0500] Furthermore, plants that contain a modified amount of substances of content or new substances of content, by the use of recombinant DNA techniques, to improve human or animal nutrition, e.g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape, DOW Agro Sciences, Canada) are also within the scope of the present invention.

[0501] Furthermore, plants that contain a modified amount of substances of content or new substances of content, by the use of recombinant DNA techniques, to improve raw material production, e.g. potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato, BASF SE, Germany) are also within the scope of the present invention.

[0502] 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).

[0503] 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.

[0504] 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 stickiness, moisture retention or aging characteristics.

[0505] 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 polysaccharides, 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.

[0506] 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.

[0507] 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, Af, A -dim ethyl form am ide. 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.

[0508] 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 %.

[0509] 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.

[0510] The methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with the 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, knit goods, 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 A. A-dicthyl-mcta-toluamidc (DEET), A. A-dicthylphcnylacctamidc (DEP A),

[0511] 1-(3-cyclohexan-l-yl-carbonyl)-2-methylpiperine, (2-hydroxymethylcyclohexyl) acetic acid lactone,

[0512] 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, mono and di-ethylenically unsaturated hydrocarbons, such as styrene, and aliphatic dienes, such as butadiene.

[0513] The impregnation of curtains and bed nets is done in general by dipping the textile material into emulsions or dispersions of the insecticide or spraying them onto the nets.

[0514] 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, electric 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 to the under-floor soil in order to protect wooden materials but it can also be applied to lumbered articles such as surfaces of the under-floor concrete, alcove posts, beams, ply woods, 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.

[0515] 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.

[0516] Digital Technologies

[0517] The compounds of the invention can be used in combination with models e.g. embedded in computer programs for site specific crop management, satellite farming, precision farming or precision agriculture. Such models support the site specific management of agricultural sites with data from various sources such as soils, weather, crops (e.g. type, growth stage, plant health), weeds (e.g. type, growth stage), diseases, pests, nutrients, water, moisture, biomass, satellite data, yield etc. with the purpose to optimize profitability, sustainability and protection of the environment. In particular, such models can help to optimize agronomical decisions, control the precision of pesticide applications and record the work performed.

[0518] As an example, the compounds of the invention can be applied to a crop plant according to an appropriate dose regime if a model models the development of a pest and calculates that a threshold has been reached for which it is recommendable to apply the compound of the invention to the crop plant. Commercially available systems which include agronomic models are e.g. FieldScripts™ from The Climate Corporation, Xarvio™ from BASF, AGLogic™ from John Deere, etc.

[0519] The compounds of the invention can also be used in combination with smart spraying equipment such as e.g. spot spraying or precision spraying equipment attached to or housed within a farm vehicle such as a tractor, robot, helicopter, airplane, unmanned aerial vehicle (UAV) such as a drone, etc. Such an equipment usually includes input sensors (such as e.g. a camera) and a processing unit configured to analyze the input data and configured to provide a decision based on the analysis of the input data to apply the compound of the invention to the crop plants (respectively the weeds) in a specific and precise manner. The use of such smart spraying equipment usually also requires positions systems (e.g. GPS receivers) to localize recorded data and to guide or to control farm vehicles; geographic information systems (GIS) to represent the information on intelligible maps, and appropriate farm vehicles to perform the required farm action such as the spraying.

[0520] For example, pests can be detected from imagery acquired by a camera. In an example the pests can be identified and / or classified based on that imagery. Such identification and / classification can make use of image processing algorithms. Such image processing algorithms can utilize machine learning algorithms, such as trained neutral networks, decision trees and utilize artificial intelligence algorithms. In this manner, the compounds described herein can be applied only where needed.

[0521] Seed treatment

[0522] 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.

[0523] The compounds of the present invention are also suitable for the treatment of seeds in order to protect the seed from insect pest, in particular from soil -living insect and mite pests and the resulting plant's roots and shoots against soil pests and foliar insects.

[0524] The compounds of the present invention are particularly useful for the protection of the seed from soil pests and the resulting plant's roots (white grub, termites, wireworms) and shoots against soil pests and foliar insects. The protection of the resulting plant's roots and shoots is preferred. More preferred is the protection of resulting plant's shoots from piercing and sucking insects, wherein the protection from aphids, jassids, thrips and white fly is most preferred.

[0525] 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 pre -germination with a compound of the present invention thereof. Particularly preferred is a method, wherein the plant's 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.

[0526] 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.

[0527] 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.

[0528] 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.

[0529] 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.

[0530] 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 com), 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.

[0531] 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.

[0532] For example, the compounds 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), Furthermore, the compounds 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).

[0533] The seed treatment application of the compounds 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.

[0534] 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.

[0535] Animal health

[0536] The present invention also provides an agricultural and / or veterinary composition comprising at least one compound of the present invention.

[0537] 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.

[0538] 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.

[0539] 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.

[0540] 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.

[0541] 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. 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.

[0542] 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.

[0543] Surprisingly it has now been found that compounds of the present invention are suitable for combating endo and ectoparasites in and on animals.

[0544] 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 fresh and salt-water fish such as trout, carp and eels.

[0545] 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.

[0546] Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.

[0547] 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.

[0548] The compounds of the present invention are especially useful for combating ectoparasites.

[0549] The compounds of the present invention are especially useful for combating parasites of the following orders and species, respectively: fleas (Siphonaptera) , e.g. Ctenocephalides felis, 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 hrunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis, flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes alhopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles alhimanus, Anopheles gamhiae, Anopheles freehorni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya hezziana, 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 tarsalis, Culiseta inorncita, 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, Lycoria pectoralis, Mans onia 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 (Parasitiformes) : 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.

[0550] Roundworms Nematoda:

[0551] 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 Hahronema 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 huski, Clonorchis sinensis, Schistosoma spp., Trichohilharzia 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.

[0552] The compounds of formula (I) and compositions containing them are particularly useful for the control of pests from the orders Diptera, Siphonaptera and Ixodida.

[0553] In one embodiment, the present invention provides use of the compounds of formula (I) and compositions containing them for combating mosquitoes.

[0554] In one embodiment, the present invention provides use of the compounds of formula (I) and compositions containing them for combating flies.

[0555] In one embodiment, the present invention provides use of the compounds of formula (I) and compositions containing them for combating fleas.

[0556] The use of the compounds of the present invention and compositions containing them for combating ticks is still another embodiment of the present invention.

[0557] The compounds of the present invention are also especially useful for combating endoparasites (roundworms nematoda, thorny headed worms and planarians).

[0558] In one embodiment, the administration of the compounds of the present invention can be carried out both prophy tactically and therapeutically.

[0559] 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.

[0560] 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.

[0561] 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.

[0562] 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-in water 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.

[0563] 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.

[0564] The solutions are filtered and filled sterile.

[0565] Suitable solvents are physiologically tolerable solvents such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, A-mcthylpyrrolidonc. 2-pyrrolidone, and mixtures thereof.

[0566] The active compounds can optionally be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.

[0567] 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.

[0568] Suitable preservatives are benzyl alcohol, trichlorobutanol, p -hydroxybenzoic acid esters, and n- butanol. 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.

[0569] Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.

[0570] 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.

[0571] Further suitable solvents are polypropylene glycol, phenyl ethanol, phenoxy ethanol, ester such as ethyl or butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ether, e.g. dipropylene glycol monomethyl ether, ketones such as acetone, methylethylketone, aromatic hydrocarbons, vegetable and synthetic oils, N, A-dimcthylfonnamidc. dimethylacetamide, transcutol, solketal, propylencarbonate, and mixtures thereof.

[0572] 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.

[0573] 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.

[0574] 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.

[0575] 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, A'-mcthylpyrrolidonc. 2-pyrrolidone, 2,2-dimethyl-4-oxy-methylene-l,3-dioxolane or glycerol formal.

[0576] Suitable colorants are, for example, all colorants permitted for use on animals and which can be dissolved or suspended. Suitable absorption-promoting substances are for example, dimethyl sulfoxide, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and copolymers thereof with polyethers, fatty acid esters, triglycerides or fatty alcohols.

[0577] Suitable antioxidants are for example, sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole or tocopherol.

[0578] 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.

[0579] 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.

[0580] 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.

[0581] 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.

[0582] In one embodiment, the compositions comprising the compounds of the present invention are applied dermally / topically . 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.

[0583] 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.

[0584] 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.

[0585] Positive crop response:

[0586] The compounds of the present invention not only control insect and mite pests effectively but also show positive crop responses such as plant growth enhancement effects like enhanced root growth, enhanced tolerant to drought, high salt, high temperature, chill, frost or light radiation, improved flowering, enhanced nutrient utilization (such as improved nitrogen assimilation), enhanced quality plant product, more number of productive tillers, enhanced resistance to fungi, insects, pests and the like, which results in higher yields.

[0587] As described herein, the compounds of formula (I) show insecticidal activities which are exerted with respect to numerous insects which attack on important agricultural crops. The compounds of the present invention were assessed fortheir activity as described in the following tests:

[0588] BIOLOGY EXAMPLES:

[0589] Example A: Plutella xylostella

[0590] The leaf dip method was used for testing, wherein the required quantity of the compound was weighed and dissolved in a tube containing a solvent solution. The tube was put on a vortex at 2000 rpm for 90 min for proper mixing and the mixture was then diluted with 0.01% Triton-X solution to get the desired test concentration. Cabbage leaves were dipped in the compound solution for 10 seconds, shade dried for 20 min and then transferred into the cells of bioassay trays. A single second instar larva was released into each cell and the tray was covered with a lid. The bio-assay trays were then kept under laboratory conditions at a temperature of 25 °C and a relative humidity of 65%. Observations on dead, moribund and alive larvae were recorded 96 h after the release. Percent mortality was calculated by combining dead and moribund larvae and comparing the result to the one of the untreated control. The compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 11, 12, 13, 14, 15, 16, 20, 21, 23, 24, 25, 26, 27, 28, 32, 42, 52, 53, 54, 60, 63, 195, 205, 206, 207, 208, 214, 215, 216, 217, 218, 219, 221, 222, 223, 224, 225, 227, 228, 274, 276, 295, 296, 297, 298, 299, 301, 302, 303, 304 & 305 recorded > 70 per cent mortality @ 300PPM.

[0591] Example B: Helicoverpa armigera

[0592] The diet incorporation method was used, in which the required quantity of the test compound was weighed and dissolved in a tube containing solvent solution. The tube was put on a vortex at 2000 rpm for 90 min for proper mixing. Semi-synthetic diet was incorporated into this solution when the temperature was approximately 60°C in the bioassay containers. Compound and diet were stirred thoroughly for proper mixing and allowed to cool for 30 min. The solidified diet was cut into equal pieces, and then each piece was transferred into one cell of a bio-assay tray. A single starved third instar larva was released into each of the cells of the bioassay trays and the tray was covered with the lid. The bio-assay trays were then kept under laboratory conditions at a temperature of 25 °C and a relative humidity of 65%. Observations on dead, moribund and alive larvae were recorded 168 h after the release of the larvae. Percent mortality was calculated by combining dead and moribund larvae and comparing the result to the one of the untreated control. The compounds 32, 42, 52, 53, 54, 60, 63, 195, 205, 206, 207, 208, 214, 215, 216, 217, 218, 218, 219, 221, 223, 224, 225, 227, 228, 274, 276, 277, 295, 296, 297, 298, 299, 301, 302, 304 & 305 recorded > 70 per cent mortality @ 300PPM.

[0593] Example C: Spodoptera litura

[0594] The diet incorporation method was used, in which the required quantity of the test compound was weighed and dissolved in a tube containing solvent solution. The tube was put on a vortex at 2000 rpm for 90 min for proper mixing. Semi-synthetic diet was incorporated into this solution when the temperature was approximately 60°C in the bioassay containers. Compound and diet were stirred thoroughly for proper mixing and allowed to cool for 30 min. The solidified diet was cut into equal pieces, and then each piece was transferred into one cell of a bio-assay tray. A single starved third instar larva was released into each of the cells of the bioassay trays and the tray was covered with the lid. The bio-assay trays were then kept under laboratory conditions at a temperature of 25 °C and a relative humidity of 65%. Observations on dead, moribund and alive larvae were recorded 168 h after the release of the larvae. Percent mortality was calculated by combining dead and moribund larvae and comparing the result to the one of the untreated control. The compounds 11, 42, 52, 54, 60, 63, 195, 205, 208, 214, 215, 218, 219, 221, 223, 224, 228, 295, 296, 297, 298, 299, 302, 304 and 305 recorded > 70 per cent mortality @ 300PPM.

[0595] Example D: Bemisia tabaci

[0596] The leaf dip method was used for testing, wherein the required quantity of the compound was weighed and dissolved in a tube containing a solvent solution. The tube was put on a vortex at 2000 rpm for 90 min for proper mixing and the mixture was then diluted with 0.01% Triton-X solution to the desired test concentration. Brinjal leaves were dipped in the compound solution for 10 seconds; shade dried for 20 min and then placed, with the abaxial side of the leaf up, on 4 mL of a solidified 1 % agar-agar solution in respective perforated container caps. Known numbers of freshly emerged whitefly adults were collected, using a modified aspirator, released into a perforated container in which the cap containing the treated leaf was placed. The sealed containers were kept in a plant growth chamber at a temperature of 25 °C and a relative humidity of 65%. Observations on dead, moribund and alive adults were recorded 120 h after the release. Percent mortality was calculated by combining dead and moribund adults and comparing the result to the one of the untreated control. The compounds 1, 11, 23, 24, 42, 43, 47, 57, 59, 60, 63, 66, 70, 72, 74, 75, 78, 97, 109, 113, 124, 129, 137, 141, 205, 211, 230, 234, 265, 266, 269, 285 and 286 recorded > 70 per cent mortality @ 300 PPM.

[0597] Example E: Myzus persicae

[0598] The leaf dip method was used for testing, wherein the required quantity of the compound was weighed and dissolved in a tube containing a solvent solution. The tube was put on a vortex at 2000 rpm for 90 min for proper mixing and the mixture was then diluted with a 0.01% Triton-X solution to the desired test concentration. Capsicum leaves were dipped in the compound solution for 10 seconds, shade dried for 20 min and then placed, with the abaxial side of the leaf up, in single cells of a bio -assay tray containing 4 mL of a solidified 1 % agar-agar solution. Known numbers of third instar nymphs, collected in petri plates, were released into the cell with the treated leaf and the cell was covered with a perforated lid for better aeration. The trays were kept in a plant growth chamber at a temperature of 25 °C and a relative humidity of 70%. Observations on dead, moribund and alive nymphs were recorded 120 h after the release. Percent mortality was calculated by combining dead and moribund nymphs and comparing the result with the one of the untreated control. The compounds 1, 2, 3, 4, 5, 6, 7, 8, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 34, 35, 36, 42, 44, 45, 46, 48, 54, 55, 57, 58, 59, 60, 63, 66, 67, 69, 70, 71, 74, 75, 76, 77, 78, 79, 84, 86, 91, 93, 95, 96, 97, 98, 100, 101, 102, 103,

[0599] 109, 110, 111, 113, 114, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 128, 129, 130, 131, 132,

[0600] 133, 136, 137, 140, 141, 142, 144, 145, 146, 147, 153, 154, 155, 156, 157, 161, 162, 165, 167, 170, 175,

[0601] 180, 182, 183, 187, 188, 190, 192, 193, 196, 204, 209, 213, 225, 226, 228, 229, 236, 237, 238, 239, 241,

[0602] 261, 264, 269, 270, 273, 276, 281, 282, 283, 284, 285, 287, 290, 293, 307, 310, 313, 316, 321, 328 & 329 recorded > 70 per cent mortality @ 300 PPM.

[0603] Example F : Nilaparvata lugens

[0604] The seedling dip method was used for testing, wherein the required quantity of the compound was weighed and dissolved in a tube containing a solvent solution. The tube was put on a vortex at 2000 rpm for 90 min for proper mixing and the mixture was then diluted with a 0.01% Triton-X solution to the desired test concentration. Paddy seedlings were dipped in the compound solution for 10 seconds, shade dried for 20 min and then the seedlings were placed in glass test tubes with the roots kept in water. 15 third instar nymphs were released into each test tube and the sealed tubes were kept in a plant growth chamber at a temperature of 25 °C and a relative humidity of 75%. Observations on dead, moribund and alive nymphs were recorded 72 h after the release. Percent mortality was calculated by combining dead and moribund nymphs and comparing the result to the one of the untreated control. The compounds 1, 2, 6, 7, 9, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 27, 30, 31, 32, 33, 36, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 50, 51, 54, 55, 56, 57, 58, 59, 60, 61, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 77, 78, 79, 80, 81, 83, 84, 86, 89, 91, 92, 93, 94, 95, 96, 97, 98, 100, 101, 102, 103, 104, 106, 107, 108, 109, 111, 113, 114, 116, 117, 118, 119, 121, 122, 123, 124, 125, 126, 128, 129, 130, 131, 133, 136, 137, 139, 140,

[0605] 141, 145, 146, 150, 153, 157, 167, 168, 169, 172, 173, 174, 177, 186, 190, 196, 198, 203, 204, 217, 229, 230, 231, 232, 234, 235, 237, 239, 239, 241, 243, 244, 245, 247, 248, 249, 250, 251, 252, 253, 254, 255,

[0606] 261, 262, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 278, 279, 283, 284, 285, 286, 287,

[0607] 288, 289, 290, 291, 292, 293, 299, 300, 302, 304, 306, 310, 313, 314, 316, 318, 319, 321, 322, 330, 331

[0608] & 332 recorded > 70 per cent mortality @ 300 PPM.

[0609] Having described the invention with reference to certain preferred embodiments, other embodiments will become apparent to one skilled in the art from the consideration of the specification. It will be apparent to those skilled in the art that many modifications, both to materials and methods, may be practiced without departing from the scope of the invention.

Claims

1. WE CLAIM:

1. A compound of formula (I),wherein,R1is C1-C6-alkyl;Y is selected from O or NRY;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-C3-cycloalkyl, C3-C3-cycloalkyl-C1-C3- alkyl, and -C(O)Rla;R1ais selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, Ci-C3-alkoxy-C 1-C3- alkyl-, C3-C3-cycloalkyl, and C3-C3-cycloalkyl-C1-C3-alkyl;R2is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3- C8-cycloalkyl. a 5- or 6-membered heteroaryl ring, phenyl, -C(=O)NR5R6, -C(=O)ORb, -C(=O)-C1-C6- alkyl and -NR7R8; wherein said 5- or 6-membered heteroaryl ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S, and wherein each group of R2is unsubstituted or substituted with one, two, three or four groups of R2a;R2ais independently selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C3-cycloalkyl, -S(0)0-2-C1-C6-alkyl, -S(0)0-2-C1- C6-haloalkyl, OR4, and NRaRb;Rais selected from the group consisting of C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C2- C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C4-cycloalkyl, and OR4;Rbis selected from the group consisting of hydrogen, and C1-C6-alkyl;R2' is independently selected from the group consisting of halogen, cyano, C1-C6-alkyl, C3-C6- cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, and C1-C6-haloalkoxy;R3is selected from the group consisting of halogen, C1-C3-haloalkyl, -OC1-C3-haloalkyl, and -S(0)0- 2C1-C3-haloalkyl;Ai is selected from N, C, or CH;A2 is selected from N, C, or CH;R4is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1- C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-alkoxy-C1-C6-alkyl, and O-Cx-cycloalkyl:R5is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, OR5a, C1-C6-haloalkyl, C2-C6-haloalkenyl, O-Cx-cycloalkyl. C3-C3-cycloalkyl-C1-C6-alkyl, a 3- to 6- membered non-aromatic heterocyclic ring, a 5- or 6-membered heteroaryl ring, phenyl, and phenyl-C1- C6 -alkyl; wherein said 3- to 6-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, and 5- or 6-membered heteroaryl ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S, and wherein each group of R5is unsubstituted or substituted with one to three groups of R5b;R5ais selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, benzyl, and a 3- to 6-membered non-aromatic heterocyclic ring; wherein said 3- to 6-membered non- aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(O)0-2;R5bis independently selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6- haloalkyl, -S(0)0-2-C1-C6-alkyl, -S(0)0-2-C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;R6is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1- C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-cyanoalkyl, Ci-C6-alkoxy-C’i-C’, -alkyl-. C3-C6-cycloalkyl, and a 3- to 4-membered non-aromatic heterocyclic ring; wherein said 3- to 4-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, and wherein said 3- to 4-membered non-aromatic heterocyclic ring is unsubstituted or substituted with one or two groups of R5b; orR5and R6together with the nitrogen atom to which they are attached may form a 3 - to 6-membered non-aromatic heterocyclic ring, which optionally contains additional 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, said heterocyclic ring is optionally substituted with one to three substituents independently selected from halogen, oxo, cyano, C1-C6-alkyl, C1-C6-alkoxy, or C1-C6-haloalkyl; orNR5R6represents -N=S(O)(RX)2, wherein Rxis independently selected from the group consisting of cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, benzyl, and a 3- to 6-membered non-aromatic heterocyclic ring; wherein said 3- to 6-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2;R7is selected from the group consisting of hydrogen, C1-C6-alkyl, cyano, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-cyanoalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-alkoxy, C3-Cx-cycloalkyl. C3-C8-cycloalkyl-C1-C6-alkyl, a 3- to 6-membered non-aromatic heterocyclic ring, a 5- or 6-membered heteroaryl ring, 5- or 6-membered heteroaryl-C1-C3-alkyl, NR5R6, C1-C6-alkylsulfonyl, -C(O)R9, and C1-C3-alkyl-C(O)R9; wherein said 3- to 6-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2 and 5- or 6-membered heteroaryl ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S, and wherein each group of R7is unsubstituted or substituted with one to three groups of R7a;R7ais independently selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6- alkoxy, -C(O)O-C1-C3-alkyl, and hydroxyl;R8is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1- C6-haloalkyl, C2-C6-haloalkenyl, C3-C6-cycloalkyl, and -C(O)R9a; orR7and R8together with the nitrogen atom to which they are attached may form a 3 - to 6-membered non-aromatic heterocyclic ring, which optionally contains additional 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, said heterocyclic ring is optionally substituted with one to three substituents independently selected from halogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, or C1- C6-haloalkyl; or-NR7R8represents -N=S(O)(RXa)2, wherein RXais independently selected from the group consisting of cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, benzyl, and a 3- to 6-membered non-aromatic heterocyclic ring; wherein said 3- to 6-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2;R9is selected from the group consisting of C1-C6-alkyl, C3-Cx-cycloalkyl. C2-C6-alkenyl, C2- C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C i-C6-alkoxy-C’i-C’, -alkyl-, and C1-C6-alkoxy;R9ais selected from the group consisting of C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2- C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C i-C6-alkoxy-C’i-C’, -alkyl-, and C1-C6-alkoxy; and m is an integer selected from 1 or 2; or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof.

2. The compound of formula (I) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof according to claim 1, wherein R1is C1-C3-alkyl.

3. The compound of formula (I) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof according to claim 1 or claim 2, wherein R2is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl,-cycloalkyl. a 5- or 6-memberedheteroaryl ring, phenyl, -C(=O)NR5R6, -C(=O)ORb, -C(=O)-C1-C3-alkyl and -NR7R8; wherein said 5- or 6-membered heteroaryl ring contains 1 or 2 heteroatoms, each independently selected from N, O or S, and wherein each group of R2is unsubstituted or substituted with one or two groups of R2a.

4. The compound of formula (I) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof according to any one of claims 1 to 3, wherein R2' is C1-C-ralkyl.

5. The compound of formula (I) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof according to any one of claims 1 to 4, wherein R3is C1-C3-haloalky 1.

6. The compound of formula (I) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof according to any one of claims 1 to 5, wherein the integer m is 1.

7. The compound of formula (I) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof according to claim 1, wherein, R1is C1-C3-alkyl; Y is selected from O or NRY;RYis selected from the group consisting of hydrogen, cyano, C1-C3-alkyl, C1-C3-haloalkyl, C3- C3-cycloalkyl, and -C(O)Rla;Rlais selected from the group consisting of C1-C3-alkyl, C1-C3-haloalkyl, C1-C3-alkoxy-C1-C3- alkyl-, and C3-C5-cycloalkyl;R2is selected from the group consisting of hydrogen, halogen, cyano, C1-C-4ralkyl, C1-C4-haloalkyl, C3- C6-cycloalkyl, a 5- or 6-membered heteroaryl ring, phenyl, -C(=O)NR5R6, -C(=O)ORb, -C(=O)-C1-C3- alkyl and -NR7R8; wherein said 5- or 6-membered heteroaryl ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S, and wherein each group of R2is unsubstituted or substituted with one or two groups of R2a;R2ais independently selected from the group consisting of halogen, cyano, C1-C3-alkyl, C1-C3- haloalkyl, C3-C6-cycloalkyl and OR4;Rbis selected from the group consisting of hydrogen, and C1-C-ralkyl;R2' is C1-C4-alkyl;R3is C1-C3-haloalkyl;Ai is selected from N, C, or CH;A2 is selected from N, C, or CH;R4is selected from the group consisting of hydrogen, C1-C3-alkyl, C1-C3-haloalkyl and C3-C6- cycloalkyl;R5is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, OR5a, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C’, -alkyl and a 3- to 4-membered non-aromatic heterocyclic ring; wherein said 3- to 4-membered non-aromatic heterocyclic ring contains 1, 2 or 3 heteroatoms, each independently selected from N, O or S(0)0-2, and wherein each group of R5is unsubstituted or substituted with one to three groups of R5b;R5ais selected from the group consisting of C1-C4-alkyl and C2-C4-alkenyl;R5bis independently selected from the group consisting of halogen, cyano, C1-C3-alkyl, C1-C3- haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;R6is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C1-C3-alkoxy-C1-C3-alkyl- and C3-C6-cycloalkyl; orNR5R6represents -N=S(O)(RX)2, wherein Rxis independently selected from C1-C6-alkyl;R7is selected from the group consisting of hydrogen, C1-C4-alkyl, cyano, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-cyanoalkyl, C1-C4haloalkyl. C2-C6-haloalkenyl, C1-C4-alkoxy. C3-C6-cycloalkyl, C3-C6- cycloalkyl-C1-C3-alkyl, and -C(O)R9; wherein each group of R7is unsubstituted or substituted with one to three groups of R7a;R7ais independently selected from the group consisting of halogen, cyano, C1-C3-alkyl, C1-C3- alkoxy, and hydroxyl;R8is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, and -C(O)R9a; or-NR7R8represents -N=S(O)(RXa)2, wherein RXais independently selected from C1-C6-alkyl;R9is selected from the group consisting of C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-haloalkyl, C1- C3-alkoxy-C1-C3-alkyl- and C1-C3-alkoxy;R9ais selected from the group consisting of C1-C3-alkyl and C3-C5-cycloalkyl; and m is 1.

8. 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 tlie group consisting of surfactants and auxiliaries.

9. The composition according to claim 8, 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.

10. The composition according to claim 8, wherein said compound of formula (1) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof ranges from 0.1 %to 99 % by weight with respect to the total weight of the composition.

11. A combination comprising the compound of formula (1) or salts, stereoisomers, polymorphs, metal complexes or N-oxides thereof according to claim 1 and at least one additional biological activecompatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers or nutrients.

12. 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 8, or combination thereof according to claim 11 .

13. The method according to claim 12, wherein said method comprises applying effective dosages of compound of formula (I) in amounts ranging from 1 gai to 5000 gai per hectare in agricultural or horticultural crops.

14. 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 according to claim 1, composition thereof according to claim 8, or combination thereof according to claim 11.

15. Use of the compound of formula (I) or salts, stereoisomers, polymorphs, metal complexes, or N- oxides thereof according to claim 1 , the composition thereof according to claim 8, or the combination thereof according to claim 11, for combating insects and mite pests in agricultural crops, horticultural crops, household and vector control and parasites on animals.

16. A seed comprising the compound of formula (I) or salts, stereoisomers, polymorphs, metal complexes, or N-oxides thereof according to claim 1, the composition thereof according to claim 8 or the combination thereof according to claim 11, wherein the amount of compound of formula (I) in said seed ranges from about 0.0001 % to about 1 % by weight.

17. A compound of formula (Z) or salts thereof,wherein, R1, R2, R2, R3, Ai and A2 are as defined in claim 1.

18. A compound of formula (I-w) or salts thereof,wherein, R1, R3, Ai and A2 are as defined in claim 1.

19. A compound of formula (I-x), (I-y) or (I-z) or salts thereof,wherein, R2and R2' are as defined in claim 1.

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