Abstract: The present invention discloses a fused heterocyclic compound of formula (I), wherein, R1, Y, Q, A, G,m and E are as defined in the detailed description. The present invention further discloses methods for their preparation and use of the compounds of formula (I) as a pest control agent.
The present invention relates to fused heterocyclic compounds. More particularly, the present invention relates to fused heterocyclic compounds of formula (I) and tothe process for the preparation thereof. The present invention further relates to theuse of fused heterocyclic compounds of formula (I) as pest control agents.
BACKGROUND OF THE INVENTION:
The currently available modern insecticides and acaricides have to satisfy many requirements, for example regarding level of efficacy, residual activity and spectrum of activity as well asfurther beneficialeffects, and the possible use thereof. Efforts have been made during the pastdecades to develop selective insecticides that are acting specifically on biochemical modes of action being present only in insects or mites, but additionally showing properties that differ from known insecticides in an advantageous way.
Heterocyclic compounds with pesticidal activity are known and described, for example, in WO2016091731, WO2016162318, WO2017061497,WO2017125340, WO2017001311, WO2018095953, WO2019068572and WO2019038195.
However, by long term use of such pesticides, many pests acquire resistance and the effective control by existing insecticides and germicides that have been used conventionally over years becomes more and more difficult and this phenomenon is even increasing during recent years. Furthermore, some of those existing pesticides are highly toxic, or remain for along time in the environment because of their residual properties, which may become a growing problem due to the disruption of the ecosystem.
Therefore, there is a continuous need for new compounds which are more effective, less toxic, and environmentally safer and/or have different modes of action.
In view of the above, the present invention envisages such compounds that satisfy or overcome drawbacks associated with the prior art.
It has now surprisingly been found that certain novel pesticidally active fused heterocyclic compounds with sulfur containing substituents being subject of this invention have favorable properties as pesticides, as desired.
SUMMARY OF THE INVENTION:
Accordingly, the present invention provides a fused heterocyclic compound of formula (I) or agriculturally acceptable salts, isomers/structural isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs or N-oxides thereof.
wherein, R1, Y, Q, A, G,m and Eare as defined in the detailed description.
In one embodiment, the present invention provides a process for preparing the compound of formula (I) or agriculturally acceptable salts thereof.
In another embodiment, the present invention provides a composition for controlling or preventing invertebrate pests comprising a biologically effective amount of compound of formula (I),agriculturally acceptable salts, isomers/structural isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, or N-oxides thereofand at least one additional component selected from the group consisting of surfactants and auxiliaries.
In yet another embodiment,the composition additionally comprises at least one additional biologically activeand compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers or nutrients.
In still another embodiment, the present invention provides use of the compound of formula (I), agriculturally acceptable salts, isomers/structural isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, or N-oxides,composition or combination thereof, for combating invertebrate pests in agricultural crops and/or horticultural crops or parasites on animals.
In yet another embodiment, 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 compound of formula (I) or agriculturally acceptable salts, isomers/structural
isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, or N-oxides,composition or combination thereof.
DETAILED DESCRIPTION OF THE INVENTION:
DEFINITIONS:
The definitions provided herein for the terminologies used in the present disclosure are for illustrative purpose only and in no manner limit the scope of the present invention disclosed in the present disclosure. As used herein, the terms "comprises", "comprising", "includes", "including", "has", "having", "contains", "containing", "characterized by" or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.
The transitional phrase "consisting of" excludes any element, step or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase "consisting of" appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.
The transitional phrase "consisting essentially of" is used to define a composition or method that includes materials, steps, features, components or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term "consisting essentially of" occupies a middle ground between "comprising" and "consisting of".
Further, unless expressly stated to the contrary, "or" refers to an inclusive "or" and not to an exclusive "or". For example, a condition A "or" B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
Also, the indefinite articles "a" and "an" preceding an element or component of the present invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore "a" or "an" should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.
As referred to in this disclosure, the term "invertebrate pest" includes arthropods, gastropods and nematodes of economic importance as pests. The term "arthropod" includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans. The term "gastropod" includes snails, slugs and other Stylommatophora. The term "nematode" refers to a living organism of the Phylum Nematoda. The term "helminths" includes roundworms, heartworms, phytophagous nematodes (Nematoda), flukes (Tematoda), acanthocephala and tapeworms (Cestoda).
The term "agronomic" refers to the production of field crops such as for food and fiber and includes the growth of corn, soybeans and other legumes, rice, cereal (e.g., wheat, oats, barley, rye, rice, maize), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone and citrus), small fruit (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives).
The term "nonagronomic" refers to other than field crops, such as horticultural crops (e.g., greenhouse, nursery or ornamental plants not grown in a field), residential, agricultural, commercial and industrial structures, turf (e.g., sod farm, pasture, golf course, lawn, sports field, etc.), wood products, stored product, agro-forestry and vegetation management, public health (i.e. human) and animal health (e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as wildlife) applications.
Nonagronomic applications include protecting an animal from an invertebrate parasitic pest by administering a parasiticidally effective (i.e. biologically effective) amount of a compound of the present invention, typically in the form of a composition formulated for veterinary use, to the animal to be protected. As referred to in the present disclosure and claims, the terms "parasiticidal" and "parasiticidally" refers to observable effects on an invertebrate parasite pest to provide protection of an animal from the pest. Parasiticidal effects typically relate to diminishing the occurrence or activity of the target invertebrate parasitic pest. Such effects on the pest include necrosis, death, retarded growth, diminished mobility or lessened ability to remain on or in the host animal, reduced feeding and inhibition of reproduction. These effects on invertebrate parasite pests provide control (including prevention, reduction or elimination) of parasitic infestation or infection of the animal.
The compounds of the present disclosure may be present either in pure form or as mixtures of different possible isomeric forms such as stereoisomers or constitutional isomers. The various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, and geometric isomers. Any desired mixtures of these isomers fall within the scope of the claims of the present disclosure. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other isomer(s) or when separated from the other isomer(s). Additionally, the person skilled in the art knows processes or methods or technology to separate, enrich, and/or to selectively prepare said isomers.
The meaning of various terms used in the description shall now be illustrated.
The term "aliphatic compound/s" or "aliphatic group/s" used herein is an organic compound/swhose carbon atoms are linked in straight chains, branched chains, or non-aromatic rings.
The term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" or -N(alkyl) or alkylcarbonylalkyl or alkylsuphonylamino includes straight-chain or branched C1 to C24 alkyl, preferably C1 to C15 alkyl, more preferably C1 to C10 alkyl, most preferably C1 to C6 alkyl. Representative examples of alkyl include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and l-ethyl-2-methylpropyl or the different isomers. If the alkyl is at the end of a composite substituent, as, for example, in alkylcycloalkyl, the part of the composite substituent at the start, for example the cycloalkyl, may be mono- or polysubstituted identically or differently and independently by alkyl. The same also applies to composite substituents in which other radicals, for example alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy and the like, are at the end.
The term "alkenyl", used either alone or in compound words includes straight-chain or branched C2to C24 alkenes, preferably C2to C15 alkenes, more preferably C2to C10 alkenes, most preferably C2to C6 alkenes. Representative examples of alkenes include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-l-propenyl, l-methyl-2 -propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2 -propenyl, 1-ethyl-1-propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-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, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, l,l-dimethyl-3-butenyl, 1,2-dimethyl-l-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, l,3-dimethyl-2-butenyl, l,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-
dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, l-ethyl-3-butenyl, 2-ethyl- 1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, l,l,2-trimethyl-2-propenyl, 1-ethyl-l-methyl-2-propenyl, l-ethyl-2-methyl-l-propenyl and l-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.
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-l-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl -2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-l-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl and the different isomers. This definition also applies to alkynyl as a part of a composite substituent, for example haloalkynyl etc., unless specifically defined elsewhere. The term "alkynyl" can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
The term "cycloalkyl"means alkyl closed to form a ring. Non-limiting examples include 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.
The term "cycloalkenyl" means alkenyl closed to form a ring including monocyclic, partially unsaturated hydrocarbyl groups. Non-limiting examples include but are not limited to cyclopropenyl, cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as a part of a composite substituent, for example cycloalkenylalkyl etc., unless specifically defined elsewhere.
The term "cycloalkynyl" means alkynyl closed to form a ring including monocyclic, partially unsaturated groups. Non-limiting examples include but are not limited to cyclopropynyl, cyclopentynyl and cyclohexynyl. This definition also applies to cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere.
The term "cycloalkoxy","cycloalkenyloxy"and the like are defined analogously. Non limiting examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to
cycloalkoxy as a part of a composite substituent, for example cycloalkoxy alkyl etc., unless specifically defined elsewhere.
The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Non-limiting examples of "haloalkyl" include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl, and 1,1,1-trifluoroprop-2-yl. This definition also applies to haloalkyl as a part of a composite substituent, for example haloalkylaminoalkyl etc., unless specifically defined elsewhere.
The terms "haloalkenyl", "haloalkynyl" are defined analogously except that, instead of alkyl groups, alkenyl and alkynyl groups are present as a part of the substituent.
The term "haloalkoxy" means straight-chain or branched alkoxy groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and l,l,l-trifluoroprop-2-oxy. This definition also applies to haloalkoxy as a part of a composite substituent, for example haloalkoxyalkyl etc., unless specifically defined elsewhere.
The term "haloalkylthio" means straight-chain or branched alkylthio groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethylthio and l,l,l-trifluoroprop-2-ylthio. This definition also applies to haloalkylthio as a part of a composite substituent, for example haloalkylthioalkyl etc., unless specifically defined elsewhere.
Non-limitingexamples of "haloalkylsulfinyl" include CF3S(O), CCl3S(O), CF3CH2S(O) and CF3CF2S(O). Examples of "haloalkylsulfonyl" include CF3S(O)2, CCl3S(O)2, CF3CH2S(O)2 and CF3CF2S(O)2.
The term "hydroxy" means–OH, Amino means–NRR, wherein R can be H or any possible substituent such as alkyl. Carbonyl means -C(O)- , carbonyloxy means -OC(O)-, sulfinyl means SO, sulfonyl means S(O)2.
The term "alkoxy" used either alone or in compound words included C1 to C24 alkoxy, preferably C1 to C15 alkoxy, more preferably C1 to C10 alkoxy, most preferably C1 to C6 alkoxy. Examples of alkoxy include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and l-ethyl-2-methylpropoxy and the different isomers. This definition also applies to alkoxy as a part of a composite substituent, for example haloalkoxy, alkynylalkoxy, etc., unless specifically defined elsewhere.
The term "Alkoxyalkyl" denotes alkoxy substitution on alkyl. Non-limitingexamples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2.
The term "alkoxyalkoxy" denotes alkoxy substitution on alkoxy.
The term "alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and l-ethyl-2-methylpropylthio and the different isomers.
Halocycloalkyl, halocycloalkenyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylcarbonyl, cycloalkylcarbonyl, haloalkoxylalkyl, and the like, are defined analogously to the above examples.
The term "alkylthioalkyl" denotes alkylthio substitution on alkyl. Representative examples of "alkylthioalkyl" include -CH2SCH2, -CH2SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and
CH3CH2SCH2CH2. "Alkylthioalkoxy" denotes alkylthio substitution on alkoxy. The term "cycloalkylalkylamino" denotes cycloalkyl substitution on alkyl amino.
The terms alkoxyalkoxyalkyl, alkylaminoalkyl, dialkylaminoalkyl, cycloalkylaminoalkyl, cycloalkylaminocarbonyl and the like, are defined analogously to "alkylthioalkyl" or cycloalkylalkylamino.
The term "alkoxycarbonyl" is an alkoxy group bonded to a skeleton via a carbonyl group (-CO-). This definition also applies to alkoxycarbonyl as a part of a composite substituent, for example cycloalkylalkoxycarbonyl and the like, unless specifically defined elsewhere.
The term "alkoxycarbonylalkylamino" denotes alkoxy carbonyl substitution on alkyl amino. "Alkylcarbonylalkylamino" denotes alkyl carbonyl substitution on alkyl amino. The terms alkylthioalkoxycarbonyl, cycloalkylalkylaminoalkyl and the like are defined analogously.
Non-limiting examples of "alkylsulfinyl" include but are not limited to methylsulphinyl, ethylsulphinyl, propylsulphinyl, 1-methylethylsulphinyl, butylsulphinyl, 1-methylpropylsulphinyl, 2-methylpropylsulphinyl, 1,1-dimethylethylsulphinyl, pentylsulphinyl, 1-methylbutylsulphinyl, 2-methylbutylsulphinyl, 3-methylbutylsulphinyl, 2,2-dimethylpropylsulphinyl, 1-ethylpropylsulphinyl, hexylsulphinyl, 1,1-dimethylpropylsulphinyl, 1,2-dimethylpropylsulphinyl, 1-methylpentylsulphinyl, 2-methylpentylsulphinyl, 3-methylpentylsulphinyl, 4-methylpentylsulphinyl, 1,1-dimethylbutylsulphinyl, 1,2-dimethylbutylsulphinyl, 1,3-dimethylbutylsulphinyl, 2,2-dimethylbutylsulphinyl, 2,3-dimethylbutylsulphinyl, 3,3-dimethylbutylsulphinyl, 1-ethylbutylsulphinyl, 2-ethylbutylsulphinyl, 1,1,2-trimethylpropylsulphinyl, 1,2,2-trimethylpropylsulphinyl, 1-ethyl-1-methylpropylsulphinyl and 1-ethyl-2-methylpropylsulphinyl and the different isomers. The term "arylsulfinyl" includes Ar-S(O), wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphinyl as a part of a composite substituent, for example haloalkylsulphinyl etc., unless specifically defined elsewhere.
Non-limiting examples of "alkylsulfonyl" include but are not limited to methylsulphonyl, ethylsulphonyl, propylsulphonyl, 1-methylethylsulphonyl, butylsulphonyl, 1-methylpropylsulphonyl, 2-methylpropylsulphonyl, 1,1-dimethylethylsulphonyl, pentylsulphonyl, 1-methylbutylsulphonyl, 2-methylbutylsulphonyl, 3-methylbutylsulphonyl, 2,2-dimethylpropylsulphonyl, 1-ethylpropylsulphonyl, hexylsulphonyl, 1,1-dimethylpropylsulphonyl, 1,2-dimethylpropylsulphonyl, 1-methylpentylsulphonyl, 2-methylpentylsulphonyl, 3-methylpentylsulphonyl, 4-methylpentylsulphonyl, 1,1-dimethylbutylsulphonyl, 1,2-dimethylbutylsulphonyl, 1,3-dimethylbutylsulphonyl, 2,2-dimethylbutylsulphonyl, 2,3-dimethylbutylsulphonyl, 3,3-dimethylbutylsulphonyl, 1-ethylbutylsulphonyl, 2-ethylbutylsulphonyl, 1,1,2-trimethylpropylsulphonyl, 1,2,2-trimethylpropylsulphonyl, 1-ethyl-1-methylpropylsulphonyl and l- ethyl-2-methylpropylsulphonyl and the different isomers. The term "arylsulfonyl" includes Ar-S(O)2, wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphonyl as a part of a composite substituent, for example alkylsulphonylalkyl etc., unless defined elsewhere.
"Alkylamino", "dialkylamino", and the like, are defined analogously to the above examples.
The term "carbocycle" includes "aromatic carbocyclic ring system" and "nonaromatic carbocylic ring system" or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which ring may be aromatic or non-aromatic (where aromatic indicates that the Huckel rule is satisfied and non-aromatic indicates that the Huckel rule is not statisfied).
The term "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.
The term "aromatic" indicates that the Huckel rule is satisfied and the term "non-aromatic" indicates that the Huckel rule is not satisfied.
The term "heterocycle" or "heterocyclic" or "heterocyclicring system " includes "aromatic heterocycle" or "heteroaryl bicyclicring system" and "nonaromatic heterocycle ring system" or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds in which ring may be aromatic or non-aromatic, wherein the heterocycle ring contains at least one heteroatom selected from N, O, S(O)0-2, and or C ring member of the heterocycle may be replaced by C(=O), C(=S), C(=CR*R*) and C=NR*, * indicates integers.
The term "non-aromatic heterocycle" or "non-aromatic heterocyclic" means three- to fifteen-membered, preferably three- to twelve-membered, saturated or partially unsaturated heterocycle containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur: mono, bi- or tricyclic heterocycles which contain, in addition to carbon ring members, one to three nitrogen atoms and/or one oxygen or sulphur atom or one or two oxygen and/or sulphur atoms; if the ring contains more than one oxygen atom, they are not directly adjacent; for example (but not limited to) oxetanyl, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 1-imidazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, l,2,4-oxadiazolidin-5-yl, l,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, l,2,4-triazolidin-1-yl, l,2,4-triazolidin-3-yl, l,3,4- oxadiazolidin-2-yl, l,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-1-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, pyrrolinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-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-l-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-l-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, pyrazynyl, morpholinyl, thiomorphlinyl, l,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, l,3,5-hexahydrotriazin-2-yl, l,2,4-hexahydrotriazin-3-yl, cycloserines, 2,3,4,5-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or -7- yl, 3,4,5,6-tetra-hydro[2H]azepin-2- or -3- or -4- or -5- or -6- or-7-yl, 2,3,4,7-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or-7- yl, 2,3,6,7-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or -7- yl, hexahydroazepin-1- or -2- or -3- or -4- yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[1 H]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, 2,3,4,7-tetrahydro[1H]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, 2,3,6,7-tetrahydro[1H]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, hexahydroazepin-1- or -2- or -3- or -4- yl, tetra- and hexahydro-1,3-diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl, tetra- and hexahydro-1,3-dioxepinyl, tetra- and hexahydro-1,4-dioxepinyl. This definition also applies to heterocyclyl as a part of a composite substituent, for example heterocyclylalkyl etc., unless specifically defined elsewhere.
The term "heteroaryl" or "aromatic heterocyclic" means 5 or 6-membered, fully unsaturated monocyclic ring system containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur; if the ring contains more than one oxygen atom, they are not directly adjacent; 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom as ring members, for example (but not limited thereto) furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, l,2,4-oxadiazolyl, l,2,4-thiadiazolyl, l,2,4-triazolyl, l,3,4-oxadiazolyl, l,3,4-thiadiazolyl, l,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-l,3-diene-l,4-diyl group in which one or two carbon atoms may be replaced by nitrogen atoms, where these rings are attached to the skeleton via one of the nitrogen ring members, for example (but not limited to) 1-pyrrolyl, 1-pyrazolyl, 1,2,4-triazol-l- yl, 1-imidazolyl, 1,2,3-triazol-l-yl and 1,3,4-triazol-l-yl.
6-membered heteroaryl which contains one to four nitrogen atoms: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain, respectively, one to three and one to four nitrogen atoms as ring members, for example (but not limited thereto) 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, l,3,5-triazin-2-yl, l,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, l-benzofuran-4-yl, l-benzofuran-5-yl, 1-benzofuran- 6-yl, l-benzofuran-7-yl, l-benzothiophen-2-yl, l-benzothiophen-3-yl, l-benzothiophen-4-yl, 1-benzothiophen-5-yl, l-benzothiophen-6-yl, l-benzothiophen-7-yl, l,3-benzothiazol-2-yl, 1,3- benzothiazol-4-yl, l,3-benzothiazol-5-yl, l,3-benzothiazol-6-yl, l,3-benzothiazol-7-yl, l,3-benzoxazol-2-yl, l,3-benzoxazol-4-yl, l,3-benzoxazol-5-yl, 1,3-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-l-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl and isoquinolin-8-yl.
This definition also applies to heteroaryl as a part of a composite substituent, for example heteroarylalkyl etc., unless specifically defined elsewhere.
The term "Trialkylsilyl" includes three branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom such as trimethylsilyl, triethylsilyl and t-butyl-dimethylsilyl. "Halotrialkylsilyl" denotes at least one of the three alkyl radicals is partially or fully substituted with halogen atoms which may be the same or different. The term "alkoxytrialkylsilyl" denotes at least one of
the three alkyl radicals is substituted with one or more alkoxy radicals which may be the same or different. The term "trialkylsilyloxy" denotes a trialkylsilyl moiety attached through oxygen.
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. Non-limiting examples of "alkylaminocarbonyl" include CH3NHC(=O), CH3CH2NHC(=O), CH3CH2CH2NHC(=O), (CH3)2CHNHC(=O) and the different butylamino -or pentylaminocarbonyl isomers. Non-limiting examples of "dialkylaminocarbonyl" include (CH3)2NC(=O), (CH3CH2)2NC(=O), CH3CH2(CH3)NC(=O), CH3CH2CH2(CH3)NC(=O) and (CH3)2CHN(CH3)C(=O). Non-limiting examples of "alkoxyalkylcarbonyl" include CH3OCH2C(=O), CH3OCH2CH2C(=O), CH3CH2OCH2C(=O), CH3CH2CH2CH2OCH2C(=O) and CH3CH2OCH2CH2C(=O). Non-limiting examples of "alkylthioalkylcarbonyl" include CH3SCH2C(=O), CH3SCH2CH2C(=O), CH3CH2SCH2C(=O), CH3CH2CH2CH2SCH2C(=O) and CH3CH2SCH2CH2C(=O). The term haloalkylsufonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkyl amino and the like are defined analogously.
Non-limiting examples of "alkylaminoalkylcarbonyl" include CH3NHCH2C(=O), CH3NHCH2CH2C(=O), CH3CH2NHCH2C(=O), CH3CH2CH2CH2NHCH2C(=O) and CH3CH2NHCH2CH2C(=O).
The term "amide" means A-R¢C=ONR¢¢-B, wherein R¢ and R¢¢ indicates substituents and A and B indicate any group.
The term "thioamide" means A-R¢C=SNR¢¢-B, wherein R¢ and R¢¢ indicates substituents and A and B indicate any group.
The total number of carbon atoms in a substituent group is indicated by the "Ci-Cj" prefix where i and j are numbers from 1 to 21. For example, C1-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH3OCH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2. In the above recitations, when a compound of formula (I) is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
When a compound is substituted with a substituent bearing a subscript that indicatesthe number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents. Further, when the subscript m in (R)m indicates an integer ranging from for example 0 to 4 then the number of substituents may be selected from the integers between 0 and 4 inclusive.
When a group contains a substituent which can be hydrogen, then, when this substituent is taken as hydrogen, it is recognized that said group is being un-substituted.
The embodiments herein and the various features and advantageous details thereof are explained with reference to the non-limiting embodiments in the description. Descriptions of well-known components and processing techniques are omitted so as to not unnecessarily obscure the embodiments herein. The examples used herein are intended merely to facilitate an understanding of ways in which the embodiments herein may be practiced and to further enable those of skilled in the art to practice the embodiments herein. Accordingly, the examples should not be construed as limiting the scope of the embodiments herein.
The description of the specific embodiments will so fully reveal the general nature of the embodiments herein that others can, by applying current knowledge, readily modify and/or adapt for various applications such specific embodiments without departing from the generic concept, and, therefore, such adaptations and modifications should and are intended to be comprehended within the meaning and range of equivalents of the disclosed embodiments. It is to be understood that the phraseology or terminology employed herein is for the purpose of description and not of limitation. Therefore, while the embodiments herein have been described in terms of preferred embodiments, those skilled in the art will recognize that the embodiments herein can be practiced with modification within the spirit and scope of the embodiments as described herein.
Any discussion of documents, acts, materials, devices, articles and the like that has been included in this specification is solely for the purpose of providing a context for the disclosure. It is not to be taken as an admission that any or all of these matters form a part of the prior art base or were common general knowledge in the field relevant to the disclosure as it existed anywhere before the priority date of this application.
The numerical values mentioned in the description and the description/claims though might form a critical part of the present invention of the present invention, any deviation from such numerical values shall still fall within the scope of the present invention if that deviation follows the same scientific principle as that of the present invention disclosed in the present invention.The inventive compound of the present invention may, if appropriate, be present as mixtures of different possible isomeric forms, especially of stereoisomers, for example E and Z, threo and erythro, and also optical isomers, but if appropriate also of tautomers. Both the E and the Z isomers, and also the threo and erythro isomers, and the optical isomers, any desired mixtures of these isomers and the possible tautomeric forms are disclosed and claimed.
The term "pest" for the purpose of the present disclosure includes but is not limited to fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, insects and rodents. Also pest is an animal or plant detrimental to humans or human concerns including crops, livestock, and forestry.
The term "plant" is understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which are protectable and non-protectable by plant breeders¢ rights.
For the purpose of the present disclosure the term "plant" includes a living organism of the kind exemplified by trees, shrubs, herbs, grasses, ferns, and mosses, typically growing in a site, absorbing water and required substances through its roots, and synthesizing nutrients in its leaves by photosynthesis. Examples of "plant" for the purpose of the present invention include but are not limited to agricultural crops such as wheat, rye, barley, triticale, oats or rice; beet, e.g. sugar beet or fodder beet; fruits and fruit trees, such as pomes, stone fruits or soft fruits, e.g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit and citrus trees, such as oranges, lemons, grapefruits or mandarins; any horticultural plants, vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; cucurbitaceae; oleaginous plants; energy and raw material plants, such as cereals, corn, soybean, other leguminous plants, rape, sugar cane or oil palm; tobacco; nuts; coffee; tea; cacao; bananas; peppers; vines (table grapes and grape juice grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, e.g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants.
Preferably, the plant for the purpose of the present invention includes but is not limited to cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and vegetables, ornamentals, any floricultural plants and other plants for use of human and animals.
The term "plant parts" is understood to mean all parts and organs of plants above and below the ground. For the purpose of the present disclosure the term plant parts includes but is not limited to cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots including taproots, lateral roots, root hairs, root apex, root cap, rhizomes, slips, shoots, fruits, fruit bodies, bark, stem, buds, auxillary buds, meristems, nodes and internodes.
The term "locus thereof" includes soil, surroundings of plant or plant parts and equipment or tools used before, during or after sowing/planting a plant or a plant part.
Application of the compounds of the present disclosure or the compound of the present disclosure in a composition optionally comprising other compatible compounds to a plant or a plant material or locus thereof include application by a technique known to a person skilled in the art which include but is not limited to spraying, coating, dipping, fumigating, impregnating, injecting and dusting.
The term "applied" means adhered to a plant or plant part either physically or chemically including impregnation.
In one embodiment, the present invention provides a compound offormula (I),
wherein,
R1 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl and C3-C8-cycloalkyl-C1-C6-alkyl;
Y is independently 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-C5-cycloalkyl and C3-C5-cycloalkyl-C1-C3-alkyl; A represents N or CR2;
G represents N or C; provided that both G are not nitrogen simultaneously;
R2 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2- C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)0-2R7,
C(=O)R8, S(O)0-1R9=NR10, N=S(O)0-1(R9)2, P(=O)(OR¢)2,Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3- C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more groups of R2a and cyclic groups of R2 may be optionally substituted with one or more groups of R2b;
R2a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl,C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)0- 1R9=NR10, N=S(O)0-1(R9)2, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R2b is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)0- 2R7, C(=O)R8, Si(R¢)3, S(O)0-1R9=NR10 and N=S(O)0-1(R9)2; or
two R2a or two R2b substituents together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)0-2 and Si(R¢)2, may form a 3- to 7-membered ring, which for its part may be substituted by one or more groups of R2ab;
R2ab is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, NR5R6, S(O)0- 2R7, S(O)0-1R9=NR10, N=S(O)0-1(R9)2, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10- heterocyclyl;
Q represents partially saturated or unsaturated, 5 to 12 memberedheterocyclic ring system which may optionally be substituted by one or more groups of R3; wherein said heterocyclicring system does not represent unsubstituted benzothiazolyl and unsubstituted N-methyl benzimidazolyl;
R3 is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)0-1R9=NR10, N=S(O)0-1(R9)2, P(=O)(OR¢)2, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3- C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more groups of R3a and cyclic groups of R3 may be optionally substituted with one or more groups of R3b;
R3a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl,C1-C6-haloalkyl, C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)0- 1R9=NR10, N=S(O)0-1(R9)2, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R3b is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, C(R¢)2-NR5R6, C(R¢)2-OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)0-1R9=NR10, N=S(O)0-1(R9)2, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
two R3a or two R3b substituents together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)m and Si(R¢)2, may form a 3- to 7-membered ring, which for its part may be substituted by one or more groups of R3ab; wherein R3ab is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR4, NR5R6 and S(O)0-2R7; two R3 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)m and Si(R¢)2 may form a three to seven membered ring, which for its part may be substituted by one or more groups selected from the group consisting of halogen, cyano, R3c, OR3c, SR3c, NR3c2, Si(R3c)3, COOR3c and CONR3c2;
R3c is selected from the group consisting of hydrogen, halogen, straight chain or branched chain C1-C6-alkyl and cyclic C3-8-alkyl; wherein each group of R3c is optionally substituted by one or more halogen;
ring E represents a 5 or 6 membered heterocyclic ring fused with ring D; wherein ring E is optionally substituted by one or more groups of R11;
R11 is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)0-1R9=NR10, N=S(O)0-1(R9)2, P(=O)(OR¢)2, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more groups of R11a and cyclic groups of R11 may be optionally substituted with one or more groups of R11b;
R11a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)0-1R9=NR10, N=S(O)0-1(R9)2, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3- C10-heterocyclyl;
R11b is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, C(R¢)2- NR5R6, C(R¢)2-OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)0-1R9=NR10, N=S(O)0- 1(R9)2, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R4 is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, S(O)2R7, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with R4a and cyclic groups of R4 may be optionally substituted with one or more groups of R4b;
R4a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR¢, NR¢R¢¢, S(O)0-2R¢, C(=O)R¢, Si(R¢)3, C6-C10- aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R4b is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR¢, NR¢R¢¢, S(O)0-2R¢, C(=O)R¢, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R5 is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, NR¢R¢¢, S(O)0-2R7, C(=O)R8, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with R5a and cyclic groups of R5 may be optionally substituted with one or more groups of R5b;
R5a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR¢, NR¢R¢¢, S(O)0-2R¢, C(=O)R¢, Si(R¢)3, C6-C10- aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R5b is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR¢, NR¢R¢¢, S(O)0-2R¢, Si(R¢)3, C(=O)R¢, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R6 is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-cycloalkyl and C(=O)R8;
R7 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, NR5R6, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more groups of R7a and cyclic groups of R7 may be optionally substituted with one or more groups of R7b;
R7a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR¢, NR¢R¢¢, S(O)0-2R¢, C(=O)R¢, C6-C10-aryl, C7- C14-aralkyl and C3-C10-heterocyclyl;
R7b is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR¢, NR¢R¢¢, S(O)0-2R¢, C(=O)R¢, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R8 is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, NR5R6, N=S(O)0-1(R9)2, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more groups of R8a and cyclic groups of R8 may be optionally substituted with one or more groups of R8b;
R8a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR¢, NR¢R¢¢, S(O)0-2R¢, C(=O)R¢, C6-C10-aryl, C7- C14-aralkyl and C3-C10-heterocyclyl;
R8b is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR¢, NR¢R¢¢, S(O)0-2R¢, C(=O)R¢, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R9 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl and C(=O)R8;
R10 is selected from the group consisting of hydrogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, Si(R¢)3, S(O)0-2R7 and C(=O)R8;
R¢ is selected from the group consisting of halogen, cyano, R¢¢, OR¢¢, N(R¢¢)2, S(O)0-2R¢¢, C(=O)R¢¢, C(=O)OR¢¢ and C(=O)N(R¢¢)2R8;
R¢¢ is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl,C1-C6-haloalkyl and C3-C8-cycloalkyl; wherein each may be optionally substituted with halogen;
each group of R1 to R11, R2a, R2b, R2ab, R3a, R3b, R3ab, R3c, R4a, R4b, R5a, R5b, R7a, R7b, R8a and R8b may be optionally substituted by one or more groups selected from the group consisting of halogen, cyano, R¢, OR¢, SR¢, N(R¢)2, COOR¢ and CON(R¢)2;
"m" is an integer ranging from 0 to 2;
or agrochemically acceptable salts, isomers/structural isomers, stereo-isomers, diastereoisomers, enantiomers, tautomers, polymorphs, metal complexes or N-oxides thereof.
In another embodiment, the compound of formula (I) is represented by compound of formula (IA);
Formula (IA)
In yet another embodiment, the compound of formula (I) is represented by compound of formula (IB);
Formula (IB)
In one embodiment, Q is selected from the group consisting of formula Q1 to Q10:
wherein, G1,G2,G4 and G5 are independently represents N or CR3; G3 is NR6, O or S; Z is O or S; and "n" is an integer ranging from 0 to 4.
In a preferred embodiment, Q is selected from the group consisting of Q1a to Q10b:
wherein, # denotes the point of attachment to the ring D,R6is selected from the group consisting of hydrogen, C1-C6-alkyland cyclic C3-10-alkyl; wherein each group of R6 is optionally substituted by one or more halogen and "n" is an integer ranging from 0 to 4.
In one embodiment, the present invention provides a compound of formula (I), wherein at least one nitrogen is present in the fused ringsystem DE.
In another embodiment, the fused ringsystem DE is selected from the group consisting of DE-1 to DE-15:
wherein, # denotes the point of attachment to the ring Q and denotes the point of attachment to the group -S(Y)mR1.
In a preferred embodiment, the present invention provides a compound of formula (I) wherein, Q is selected from Q1a, Q1b, Q1c,Q1h, Q2b, Q3a, Q5b, Q5d, Q6aQ6b, Q9a, Q9b
Q7a or Q8a;
wherein, # denotes the point of attachment to the ring D;
R3 is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl and S(Y)0-2R7;
R6 is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C10-cycloalkyl;
R7 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl;
fused rings DE are selected from the group consisting of
wherein, # denotes the point of attachment to the ring Q and denotes the point of attachment to the group -S(Y)mR1;
R2 is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl,C6-C8-aryl, C7-C9-aralkyl and C3-C6-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more groups of R2a and cyclic groups of R2 may be optionally substituted with one or more groups of R2b;
"m" is an integer ranging from 0 to 2;
"n" is an integer ranging from 0to 4;
R11 is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR4, NR5R6, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more groups of R11a and cyclic groups of R11 may be optionally substituted with one or more groups of R11b.
In another preferred embodiment, the compound of formula (I) is selected from 2-(1-(3,5-dichlorophenyl)-2-(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)imidazo[1,2-a]pyridin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 6-(1-bromo-2-(ethylsulfonyl)indolizin-3-yl)-7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine; 2-(2-(ethylsulfonyl)imidazo[1,2-a]pyridin-3-yl)-5-(trifluoromethyl)benzo[d]oxazole; 2-(2-(ethylsulfonyl)-7-(trifluoromethyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(8-(3,5-dichlorophenyl)-2-(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(1-(3,5-dichlorophenyl)-2-(ethylsulfonyl)-7-(trifluoromethyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-(3,5-dichlorophenyl)-2-(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-
b]pyridine; 2-(2-(ethylthio)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)thio)benzo[d]oxazole; 2-(2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)thio)benzo[d]oxazole; 2-(2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(2-(ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)thio)benzo[d]oxazole; 2-(2-(ethylsulfonyl)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(2-(ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)thio)benzo[d]oxazole; 2-(2-(ethylsulfonyl)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(7-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(4-chlorophenyl)-2-
(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)thio)benzo[d]oxazole; 2-(7-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)thio)benzo[d]oxazole; 2-(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(2-(ethylthio)-5-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-5-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-5-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(6-chloro-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-6-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-chloro-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(6-chloro-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(6-chloro-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-6-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-5-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-5-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-5-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl- 6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-6-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(5-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-6-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(5-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(5-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(5-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(6-bromo-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-bromo-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(6-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(6-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(6-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-6-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(5-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(5-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-6-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-7-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(5-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(5-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 3-(7-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine; 2-(2-(ethylthio)-7-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 3-(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine; 2-(2-(ethylthio)-6-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-6-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3,5-difluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3,5-difluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3-chloro-5-fluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3-chloro-5-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3,4-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 7-(3,5-dichlorophenyl)-2-(ethylthio)-3-(1-methyl-5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)pyrazolo[1,5-a]pyrimidine; 2-(ethylthio)-3-(1-methyl-5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)pyrazolo[1,5-a]pyrimidine; 7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)-3-(1-methyl-5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)pyrazolo[1,5-a]pyrimidine; 2-(ethylsulfonyl)-3-(1-methyl-5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)pyrazolo[1,5-a]pyrimidine; 2-(2-(ethylsulfonyl)-6-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 3-(7-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine; 3-(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine; 2-(7-(2,3-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(2,3-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-
(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(4-chloro-3-fluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(4-chloro-3-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(4-chloro-3-fluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(2,4-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(2,4-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(2,4-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3-chloro-5-fluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3-chloro-5-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3,5-bis(trifluoromethyl)phenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3,5-bis(trifluoromethyl)phenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-methylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-methylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; (7-(3,5-dichlorophenyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(imino)- 6-sulfanone; 2-(2-(ethylsulfonyl)-7-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-7-methylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3-chloro-4-fluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5,7-bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5,7- bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(ethylthio)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one; 2-(7-bromo-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(ethylsulfonyl)-N-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine; 6-(8-(4-chloro-3-fluorophenyl)-2-(ethylsulfonyl)indolizin-3-yl)-7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine; 2-(2-(ethylsulfonyl)-7-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(ethylthio)-N-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine; 2-(2-(ethylsulfonyl)-7-(3-fluorophenoxy)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 6-(8-(4-chloro-3-fluorophenyl)-2-(ethylsulfonyl)imidazo[1,2-a]pyridin-3-yl)-7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine; 2-(6-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyrazine; 4-(2-(ethylsulfonyl)-3-(7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazin-6-yl)indolizin-8-yl)-2-fluorobenzonitrile; 2-(8-(cyclopropylmethyl)-2-(ethylsulfonyl)imidazo[1,2-a]pyridin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(4-chloro-1H-pyrazol-1-yl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(5-methyl-1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(1-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-cyclopropyl-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrazine; 2-(2-(ethylsulfonyl)-7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)imidazo[1,2-c]pyrimidine; 4-(2-(ethylsulfonyl)-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)morpholine; 2-(7-(4-chloro-3-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-c]pyrimidine; 2-(2-(ethylsulfonyl)-7-(1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-c]pyrimidine; 2-(2-(ethylsulfonyl)-5,7-bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 6-(1-bromo-2-(ethylsulfonyl)-8-methylindolizin-3-yl)-7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine; 6-(8-bromo-2-(ethylsulfonyl)indolizin-3-yl)-3-(difluoromethyl)-7-methyl-7H-imidazo[4,5-c]pyridazine; 2-(2-(ethylsulfonyl)-7-methoxypyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(methylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(ethylsulfonyl)-3-(3-
methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[1,5-a]pyrimidine-7(4H)-thione; 2-(2-(ethylsulfonyl)-7-(1,1,2,2-tetrafluoroethoxy)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-ethoxy-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyrazine; diethyl((2-(ethylsulfonyl)-3-(6-(trifluoromethyl)imidazo[1,2-a]pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)imino)-l6-sulfanone; 2-(ethylsulfonyl)-N,N-dimethyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)imidazo[1,2-a]pyridin-8-amine; 6-(2-(ethylsulfonyl)-7-(5-(trifluoromethyl)pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine; 2-(7-(4-chloro-3-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3,5-dimethyl-6-(trifluoromethyl)-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one; 2-(2-(ethylsulfonyl)-7-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3,5-dimethyl-6-(trifluoromethyl)-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one; 2-(7-(3-chloro-5-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrazine; 2-(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)imidazo[1,2-c]pyrimidine; 2-(7-(4-chloro-3-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-methyl-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one; 2-(7-(5-chloropyridin-2-yl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine; 2-(2-(ethylsulfonyl)-7-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-methyl-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one; 2-(2-(ethylsulfonyl)-7-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-c]pyrimidine; ethyl(3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(methylimino)-l6-sulfanone.
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 to 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.
An anion part of the salt in case the compound of formula (I) is a cationic or capable of forming a cation can be inorganic or organic. Alterntively, a cation part of the salt in case the compound of formula (I) is an anionic or capable of forming anion can be inorganic or organic. Examples of inorganic anion part of the salt include but are not limited to chloride, bromide, iodide, fluoride, sulfate, phosphate, nitrate, nitrite, hydrogen carbonates and hydrogen sulfate. Examples of organic anion part of the salt include but are not limited to formate, alkanoates, carbonates, acetates, trifluoroacetate, trichloroacetate, propionate, glycolate, thiocyanate, lactate, succinate, malate, citrates, benzoates, cinnamates, oxalates, alkylsulphates, alkylsulphonates, arylsulphonates aryldisulphonates, alkylphosphonates, arylphosphonates, aryldiphosphonates, p-toluenesulphonate, and salicylate. Examples of inorganic cation part of the salt include but are not limited to alkali and alkaline earth metals. Examples of organic cation part of the salt include but are not limited to pyridine, methyl amine, imidazole, benzimidazole, hitidine, phosphazene, tetramethyl ammonium, tetrabutylammonium, choline and trimethylamine.
Metal ions in metal complexes of the compound of formula (I) are especially the ions of the elements of the second main group, especially calcium and magnesium, of the third and fourth main group, especially aluminium, tin and lead, and also of the first to eighth transition groups, especially chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Particular preference is given to the metal ions of the elements of the fourth period and the first to eighth transition groups. Here, the metals can be present in the various valencies that they can assume.
In one embodiment, the present invention provides a compound of formula (I), agriculturally acceptable salts, metal complexes, constitutional isomers, stereo-isomers, diastereoisomers, enantiomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, geometric isomers, or N-oxides thereof and its composition with the excipient, inert carrier or any other essential ingredient such as surfactants, additives, solid diluents and liquid diluents.
The compounds of formula (I), (including all stereoisomers, N-oxides, and salts thereof), typically exist in more than one form, and formula (I) thus includes all crystalline and non-crystalline forms of the compounds that formula (I) represents. Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts. Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types). The term "polymorph" refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due to the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability. One skilled in the art will appreciate that a polymorph of a compound represented by formula (I) can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound represented by formula (I). Preparation and isolation of a particular polymorph of a compound represented by formula (I) can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures.
In an embodiment, the present invention provides a process for preparing the compound of formula (I) or agriculturally acceptable salts.
The compound of formula (I) can be prepared according to schemes: 1-23/examples described herein. The process for preparing compound of formula (I), more specifically compound of formula (Ia) or compound of formula (Ib) wherein Q is Q1 or Q2 comprises the reaction of compound of formula (2), with compound of formula (3) or (4), wherein M is O, S, NR¢to obtain compound of formula (Ia) and (Ib). The process is summarized in scheme 1:
Scheme: 1
wherein, R1, R3,A, G, G1,G2,G3, G4, G5, E, mand n have the meanings as described above.
The compound of formula (3) and formula (4) are either commercially available or can be prepared by using the methods known or analogously described in US200369257, WO200665703, WO2009131237, WO2010125985, WO2011043404, WO2011040629, WO2012086848, WO2013018928 and WO2015000715.
In scheme 1, carboxylic acid group present in the compound of formula (2) can be converted to a more reactive functional group, such as an acyl halide, mixed anhydride, acyl azide, N-acylbenzotriazoles, active esters, or via an in situ activation by peptide coupling reagents such as bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl); dicyclohexyl carbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), followed by amide bond formation with compound of formula (3) in solvents such as dichloromethane, dichloroethane, N,N-dimethylacetamide, tetrahydrofuran, acetonitrile or a mixture thereof to obtain compound of formula (5). Organic non-nucleophilic bases such as triethyl amine, ethyldiisopropyl amine, pyridine, N-methyl pyrrolidine, 1,8-diazabicyclo[5.4.0]undec-7-enemay be used. The reaction can be carried out at a temperature ranging from about 0 °Cand about 150 °C.
The compound of formula (5) can be converted to a compound of formula (Ia) by dehydration, following conventional or under microwave conditions, in the presence of an acid catalyst, for example methane sulfonic acid, or para-toluene sulfonic acid, in an inert solvent such as N-methyl pyrolidine at temperature ranging from about 25 °Cand about 185 °C. Such processes have been described previously in WO2009131237, WO2010125985, WO2011043404, WO2011040629, WO2012086848, WO2013018928, WO2015000715 and WO2015121136.
Alternatively, the compound of formula (5) can be converted to a compound of formula (Ia) wherein M is oxygen under Mitsunobu conditions well known to those skilled in the art using di-isopropyl azodicarboxylate, triphenyl phosphine in an inert solvent such as diethyl ether, tetrahydrofuran at a temperature ranging from about 25 °C and about 50 °C. This process is described previously in WO2009131237.
Application of methods of scheme 1 in the reaction of compound of formula (2) with compound of formula (4), can lead to compound of formula (Ib).
A process for the synthesis of compound of formula (I) represented by compound of formula (Ic and Id) is depicted in scheme 2. The compound of formula (Ic) or (Id) can be prepared by reacting compound of formula (6) with compound of formula (3) or (4) to obtain compound of formula (7) or (8). Further, the compound of formula (7) and (8) (wherein X is a halogen, for example fluorine, chlorine or bromine) can be reacted with a compound of formula (9) or with a compound of formula (10), wherein M1 is for example sodium or potassium, optionally in the presence of a suitable base, such as alkali metal carbonates, for example sodium carbonate or potassium carbonate, or alkali metal hydrides such as sodium hydride, or alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, in an inert solvent at temperatures ranging from about 25 °C and about 110 °C to obtain compound of formula (Ic) or (Id).
CLAIMS:
1. A compound of formula (I),
Formula (I)
wherein,
R1 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl and C3-C8-cycloalkyl-C1-C6-alkyl;
Y is independently 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-C5-cycloalkyl and C3-C5-cycloalkyl-C1-C3-alkyl; A represents N or CR2;
G represents N or C; provided that both G are not nitrogen simultaneously;
R2 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)0- 2R7, C(=O)R8, S(O)0-1R9=NR10, N=S(O)0-1(R9)2, P(=O)(OR¢)2,Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more groups of R2a and cyclic groups of R2 may be optionally substituted with one or more groups of R2b; R2a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)0- 1R9=NR10, N=S(O)0-1(R9)2, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R2b is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)0- 2R7, C(=O)R8, Si(R¢)3, S(O)0-1R9=NR10 and N=S(O)0-1(R9)2; or
two R2a or two R2b substituents together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)0-2 and
Si(R¢)2, may form a 3- to 7-membered ring, which for its part may be substituted by one or more groups of R2ab;
R2ab is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, NR5R6, S(O)0- 2R7, S(O)0-1R9=NR10, N=S(O)0-1(R9)2, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10- heterocyclyl;
Q represents partially saturated or unsaturated, 5 to 12 membered heterocyclic ring system which may optionally be substituted by one or more groups of R3; wherein said heterocyclic ring system does not represent unsubstituted benzothiazolyl and unsubstituted N-methyl benzimidazolyl;
R3 is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)0-1R9=NR10, N=S(O)0-1(R9)2, P(=O)(OR¢)2, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more groups of R3a and cyclic groups of R3 may be optionally substituted with one or more groups of R3b;
R3a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)0- 1R9=NR10, N=S(O)0-1(R9)2, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R3b is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, C(R¢)2-NR5R6, C(R¢)2-OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)0-1R9=NR10, N=S(O)0-1(R9)2, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
two R3a or two R3b substituents together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)m and Si(R¢)2, may form a 3- to 7-membered ring, which for its part may be substituted by one or more groups of R3ab; wherein R3ab is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR4, NR5R6, S(O)0-2R7;
two R3 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)m and Si(R¢)2 may form a three to seven membered ring, which for its part may be substituted by one or more groups selected from the group consisting of halogen, cyano, R3c, OR3c, SR3c, NR3c2, Si(R3c)3, COOR3c, and CONR3c2;
R3c is selected from the group consisting of hydrogen, halogen, straight chain or branched chain C1-C6-alkyl and cyclic C3-8-alkyl; wherein each group of R3c is optionally substituted by one or more halogen;
ring E represents a 5 or 6 membered heterocyclic ring fused with ring D; wherein ring E is optionally substituted by one or more groups of R11;
R11 is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)0-1R9=NR10, N=S(O)0-1(R9)2, P(=O)(OR¢)2, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more groups of R11a and cyclic groups of R11 may be optionally substituted with one or more groups of R11b;
R11a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)0-1R9=NR10, N=S(O)0-1(R9)2, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3- C10-heterocyclyl;
R11b is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, C(R¢)2- NR5R6, C(R¢)2-OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)0-1R9=NR10, N=S(O)0- 1(R9)2, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R4 is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, S(O)2R7, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with R4a and cyclic groups of R4 may be optionally substituted with one or more groups of R4b;
R4a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR¢, NR¢R¢¢, S(O)0-2R¢, C(=O)R¢, Si(R¢)3, C6-C10- aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R4b is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR¢, NR¢R¢¢, S(O)0-2R¢, C(=O)R¢, Si(R¢)3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R5 is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4,NR¢R¢¢, S(O)0-2R7, C(=O)R8, Si(R¢)3, C6-C10- aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with R5a and cyclic groups of R5 may be optionally substituted with one or more groups of R5b;
R5a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR¢, NR¢R¢¢, S(O)0-2R¢, C(=O)R¢, Si(R¢)3, C6-C10- aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R5b is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR¢, NR¢R¢¢, S(O)0-2R¢, Si(R¢)3, C(=O)R¢, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R6 is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-cycloalkyl and C(=O)R8;
R7 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, NR5R6, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more groups of R7a and cyclic groups of R7 may be optionally substituted with one or more groups of R7b;
R7a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR¢, NR¢R¢¢, S(O)0-2R¢, C(=O)R¢, C6-C10-aryl, C7- C14-aralkyl and C3-C10-heterocyclyl;
R7b is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR¢, NR¢R¢¢, S(O)0-2R¢, C(=O)R¢, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R8 is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, NR5R6, N=S(O)0-1(R9)2, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more groups of R8a and cyclic groups of R8 may be optionally substituted with one or more groups of R8b;
R8a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR¢, NR¢R¢¢, S(O)0-2R¢, C(=O)R¢, C6-C10-aryl, C7- C14-aralkyl and C3-C10-heterocyclyl;
R8b is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR¢, NR¢R¢¢, S(O)0-2R¢, C(=O)R¢, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl;
R9 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl and C(=O)R8;
R10 is selected from the group consisting of hydrogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, Si(R¢)3, S(O)0-2R7 and C(=O)R8; R¢ is selected from the group consisting of halogen, cyano, R¢¢, OR¢¢, N(R¢¢)2, S(O)0-2R¢¢, C(=O)R¢¢, C(=O)OR¢¢ and C(=O)N(R¢¢)2R8;
R¢¢ is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1- C6-haloalkyl and C3-C8-cycloalkyl; wherein each may be optionally substituted with halogen;
each group of R1 to R11, R2a, R2b, R2ab, R3a, R3b, R3ab, R3c, R4a, R4b, R5a, R5b, R7a, R7b, R8a and R8b may be optionally substituted by one or more groups selected from the group consisting of halogen, cyano, R¢, OR¢, SR¢, N(R¢)2, COOR¢ and CON(R¢)2;
"m" is an integer ranging from 0 to 2;
or agrochemically acceptable salts, isomers/structural isomers, stereo-isomers, diastereoisomers, enantiomers, tautomers, polymorphs, metal complexes or N-oxides thereof.
2. The compound of formula (I) according to claim 1, wherein Q is selected from the group consisting of Q1to Q10;
wherein, # denotes the point of attachment to the ring D;
G1, G2,G4 and G5 are independently represents N or CR3; G3 is NR6, O, S; Z is O or S; and "n" is an integer ranging from 0 to 4.
3. The compound of formula (I) according to claim 1, wherein Q is selected from the group consisting of Q1a to Q10b:
wherein, # denotes the point of attachment to the ring D, R6 is selected from the group consisting of hydrogen, C1-C6-alkyl, and cyclic C3-10-alkyl; wherein each group of R6 is optionally substituted by one or more halogen and "n" is an integer ranging from 0 to 4.
4. The compound of formula (I) according to claim 1, wherein fused ring DE is selected from the group consisting of DE-1 to DE-15;
wherein, #denotes the point of attachment to the ring Q and denotes the point of attachment to the group -S(Y)mR1and "n" is an integer ranging from 0 to 4.
5. The compound of formula (I) according to claim 1, wherein Q is selected from Q1a, Q1b, Q1c, Q1h,
wherein,# denotes the point of attachment to the ring D;
R3 is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8- cycloalkyl and S(Y)0-2R7;
R6 is selected from the group consisting of hydrogen, C1-C6-alkyland C3-C10-cycloalkyl;
fused rings D and E are selected from the group consisting of
wherein, #denotes the point of attachment to the ring Q and denotes the point of attachment to the group -S(Y)mR1;
R2 is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8- cycloalkyl,C6-C8-aryl, C7-C9-aralkyl and C3-C6-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more groups of R2a and cyclic groups of R2 may be optionally substituted with one or more groups of R2b;
"m" is an integer ranging from 0 to 2;
"n" is an integer ranging from 0to 4;
R11 is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8- cycloalkyl, OR4, NR5R6, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more groups of R11a and cyclic groups of R11 may be optionally substituted with one or more groups of R11b.
6. The compound of formula (I) according to claim 1, wherein said compound of formula (I) is selected from 2-(1-(3,5-dichlorophenyl)-2-(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)imidazo[1,2-a]pyridin-3-yl)-3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 6-(1-bromo-2-(ethylsulfonyl)indolizin-3-yl)-7-methyl- 3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine; 2-(2-(ethylsulfonyl)imidazo[1,2-a]pyridin-3-yl)-5- (trifluoromethyl)benzo[d]oxazole; 2-(2-(ethylsulfonyl)-7-(trifluoromethyl)indolizin-3-yl)-3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(8-(3,5-dichlorophenyl)-2-(ethylsulfonyl)indolizin-3- yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(1-(3,5-dichlorophenyl)-2- (ethylsulfonyl)-7-(trifluoromethyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridine; 2-(6-(3,5-dichlorophenyl)-2-(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)- 3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5,7-dimethylpyrazolo[1,5- a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5,7- dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2- (2-(ethylsulfonyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-5- ((trifluoromethyl)thio)benzo[d]oxazole; 2-(2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5,7-dimethylpyrazolo[1,5- a]pyrimidin-3-yl)-5-((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(2-(ethylsulfonyl)pyrazolo[1,5- a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2- (ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)thio)benzo[d]oxazole; 2-(2-
(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(2-(ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)thio)benzo[d]oxazole; 2-(2-(ethylsulfonyl)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(2-(ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)thio)benzo[d]oxazole; 2-(2-(ethylsulfonyl)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(7-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)thio)benzo[d]oxazole; 2-(7-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)thio)benzo[d]oxazole; 2-(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5- a]pyrimidin-3-yl)-5-((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(2-(ethylthio)-5-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-5-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-5-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(6-chloro-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-6-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-chloro-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(6-chloro-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(6-chloro-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-6-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-5-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-5-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-5-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-6-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(5-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-6-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(5-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(5-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(5-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(6-bromo-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-bromo-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(6-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(6-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(6-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-6-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(5-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(5-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-6-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-7-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(5-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(5-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 3-(7-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-7- (trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine; 2-(2-(ethylthio)-7-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 3-(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine; 2-(2-(ethylthio)-6-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-6-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3,5-difluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3,5-difluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3-chloro-5-fluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3-chloro-5-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3,4-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 7-(3,5-dichlorophenyl)-2-(ethylthio)-3-(1-methyl-5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)pyrazolo[1,5-a]pyrimidine; 2-(ethylthio)-3-(1-methyl-5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)pyrazolo[1,5-a]pyrimidine; 7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)-3-(1-methyl-5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)pyrazolo[1,5-a]pyrimidine; 2-(ethylsulfonyl)-3-(1-methyl-5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)pyrazolo[1,5-a]pyrimidine; 2-(2-(ethylsulfonyl)-6-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 3-(7-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine; 3-(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine; 2-(7-(2,3-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(2,3-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(4-chloro-3-fluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(4-chloro-3-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(4-chloro-3-fluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(2,4-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(2,4-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(2,4-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3-chloro-5-fluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3-chloro-5-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3,5-bis(trifluoromethyl)phenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3,5-bis(trifluoromethyl)phenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-methylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-methylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; (7-(3,5-dichlorophenyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(imino)- 6-sulfanone; 2-(2-(ethylsulfonyl)-7-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-7-methylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3-chloro-4-fluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5,7-bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3- methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5,7-bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(ethylthio)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one; 2-(7-bromo-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(ethylsulfonyl)-N-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine; 6-(8-(4-chloro-3-fluorophenyl)-2-(ethylsulfonyl)indolizin-3-yl)-7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine; 2-(2-(ethylsulfonyl)-7-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(ethylthio)-N-methyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine; 2-(2-(ethylsulfonyl)-7-(3-fluorophenoxy)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 6-(8-(4-chloro-3-fluorophenyl)-2-(ethylsulfonyl)imidazo[1,2-a]pyridin-3-yl)-7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine; 2-(6-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyrazine; 4-(2-(ethylsulfonyl)-3-(7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazin-6-yl)indolizin-8-yl)-2-fluorobenzonitrile; 2-(8-(cyclopropylmethyl)-2-(ethylsulfonyl)imidazo[1,2-a]pyridin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(4-chloro-1H-pyrazol-1-yl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(5-methyl-1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(1-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-cyclopropyl-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrazine; 2-(2-(ethylsulfonyl)-7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)imidazo[1,2-c]pyrimidine; 4-(2-(ethylsulfonyl)-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)morpholine; 2-(7-(4-chloro-3-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-c]pyrimidine; 2-(2-(ethylsulfonyl)-7-(1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-c]pyrimidine; 2-(2-(ethylsulfonyl)-5,7-bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 6-(1-bromo-2-(ethylsulfonyl)-8-methylindolizin-3-yl)-7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine; 6-(8-bromo-2-(ethylsulfonyl)indolizin-3-yl)-3-(difluoromethyl)-7-methyl-7H-imidazo[4,5-c]pyridazine; 2-(2-(ethylsulfonyl)-7-methoxypyrazolo[1,5-a]pyrimidin-3-yl)-3-
methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7- (methylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[1,5- a]pyrimidine-7(4H)-thione; 2-(2-(ethylsulfonyl)-7-(1,1,2,2-tetrafluoroethoxy)pyrazolo[1,5- a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-ethoxy-2- (ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyrazine; diethyl((2- (ethylsulfonyl)-3-(6-(trifluoromethyl)imidazo[1,2-a]pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7- yl)imino)-l6-sulfanone; 2-(ethylsulfonyl)-N,N-dimethyl-3-(3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridin-2-yl)imidazo[1,2-a]pyridin-8-amine; 6-(2-(ethylsulfonyl)-7-(5- (trifluoromethyl)pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-methyl-3-(trifluoromethyl)-7H- imidazo[4,5-c]pyridazine; 2-(7-(4-chloro-3-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin- 3-yl)-3,5-dimethyl-6-(trifluoromethyl)-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one; 2-(2- (ethylsulfonyl)-7-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3,5- dimethyl-6-(trifluoromethyl)-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one; 2-(7-(3-chloro-5- fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)- [1,2,4]triazolo[1,5-a]pyrazine; 2-(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin- 3-yl)-7-(trifluoromethyl)imidazo[1,2-c]pyrimidine; 2-(7-(4-chloro-3-fluorophenyl)-2- (ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-methyl-7-(trifluoromethyl)-[1,2,4]triazolo[1,5- c]pyrimidin-5(6H)-one; 2-(7-(5-chloropyridin-2-yl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)- 6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine; 2-(2-(ethylsulfonyl)-7-(5-methyl-3- (trifluoromethyl)-1H-pyrazol-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-methyl-7-(trifluoromethyl)- [1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one; 2-(2-(ethylsulfonyl)-7-(3-(trifluoromethyl)-1H-1,2,4- triazol-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-c]pyrimidine; ethyl(3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-2- yl)(methylimino)-l6-sulfanone.
7. A composition for controlling or preventing insects and/or mite pests comprising a biologically effective amount of compound of formula (I) or agronomically acceptable salts, isomers/structural isomers, stereo-isomers, diastereoisomers, enantiomers, tautomers, polymorphs, metal complexes or N-oxides thereof according to claim 1 and at least one additional component selected from the group consisting of surfactants and auxiliaries.
8. The composition according to claim 7, wherein said composition additionally comprises at least one additional biological active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers or nutrients.
9. The composition according to claim 7, wherein said biologically effective amount of compound of formula (I) ranges from 0.1 % to 99% by weight with respect to the total weight of the composition, preferably ranges from 5 to 50% by weight with respect to the total weight of the composition.
10. A combination comprising a biologically effective amount of the compound 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 and nutrients.
11. A method of combating insects and mite pests comprising contacting the insects and mite pests, their habitat, breeding ground, food supply, plant, seed, soil, area, material or environment in which the insect and mite pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from pest attack or infestation with a biologically effective amount of compound of formula (I) or salts, metal complexes, N-oxides, isomers, polymorphs, composition or combination thereof according to claim 1 or 7 or 10.
12. A method for protecting crops from attack or infestation by insects and mite pests comprises contacting the crop with a biologically effective amount of the compound or salts, metal complexes, N-oxides, isomers, polymorphs, composition or combination thereof according to claim 1 or 7 or 10. 13. The method according to claim 11 or 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, metal complexes, N-oxides, isomers, polymorphs, composition or combination thereof according to claim 1 or 7 or 10.
15. Use of the compound of formula (I) or salts, metal complexes, N-oxides, isomers, polymorphs, composition or combination thereof according to claim 1 or 7 or 10, for combating insects and mite pests in agricultural crops, horticultural crops, household and vector control and parasites on animals. 16. The use of the compound of formula (I) according 15, wherein said agricultural crops are cereals, corn, sorghum, bajra, rice, soybean, oil seeds 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, other vegetables and ornamentals.
17. A seed comprising a compound of formula (I) or salts, metal complexes, N-oxides, isomers, polymorphs, composition or combination thereof according to claim 1 or 7 or 10, wherein the amount of compound of formula (I) in said seed ranging from about 0.0001% to about 1% by weight.
| # | Name | Date |
|---|---|---|
| 1 | 202117057129.pdf | 2021-12-08 |
| 2 | 202117057129-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [08-12-2021(online)].pdf | 2021-12-08 |
| 3 | 202117057129-STATEMENT OF UNDERTAKING (FORM 3) [08-12-2021(online)].pdf | 2021-12-08 |
| 4 | 202117057129-PRIORITY DOCUMENTS [08-12-2021(online)].pdf | 2021-12-08 |
| 5 | 202117057129-NOTIFICATION OF INT. APPLN. NO. & FILING DATE (PCT-RO-105-PCT Pamphlet) [08-12-2021(online)].pdf | 2021-12-08 |
| 6 | 202117057129-FORM 1 [08-12-2021(online)].pdf | 2021-12-08 |
| 7 | 202117057129-DECLARATION OF INVENTORSHIP (FORM 5) [08-12-2021(online)].pdf | 2021-12-08 |
| 8 | 202117057129-COMPLETE SPECIFICATION [08-12-2021(online)].pdf | 2021-12-08 |
| 9 | 202117057129-FORM-26 [28-02-2022(online)].pdf | 2022-02-28 |
| 10 | 202117057129-Proof of Right [21-04-2022(online)].pdf | 2022-04-21 |
| 11 | 202117057129-FORM 3 [03-06-2022(online)].pdf | 2022-06-03 |
| 12 | 202117057129-FORM 18 [19-04-2023(online)].pdf | 2023-04-19 |
| 13 | 202117057129-FER.pdf | 2023-08-23 |
| 14 | 202117057129-OTHERS [23-02-2024(online)].pdf | 2024-02-23 |
| 15 | 202117057129-Information under section 8(2) [23-02-2024(online)].pdf | 2024-02-23 |
| 16 | 202117057129-FORM 3 [23-02-2024(online)].pdf | 2024-02-23 |
| 17 | 202117057129-FER_SER_REPLY [23-02-2024(online)].pdf | 2024-02-23 |
| 18 | 202117057129-CLAIMS [23-02-2024(online)].pdf | 2024-02-23 |
| 19 | 202117057129-US(14)-HearingNotice-(HearingDate-27-03-2024).pdf | 2024-02-28 |
| 20 | 202117057129-US(14)-ExtendedHearingNotice-(HearingDate-10-04-2024).pdf | 2024-03-19 |
| 21 | 202117057129-Correspondence to notify the Controller [08-04-2024(online)].pdf | 2024-04-08 |
| 22 | 202117057129-Written submissions and relevant documents [25-04-2024(online)].pdf | 2024-04-25 |
| 23 | 202117057129-PatentCertificate07-05-2024.pdf | 2024-05-07 |
| 24 | 202117057129-IntimationOfGrant07-05-2024.pdf | 2024-05-07 |
| 1 | search(45)E_17-08-2023.pdf |