Abstract: The present invention provides novel pyrazolopyridine-diamides of Formula (I), wherein, the definition of W1, W2, A1, A2, A3, B1, B2, D, Z1, E, R1, R2, R3, R4, m and n is as described in the description. The present invention also relates to the composition, combination, use and method of application of the compounds of Formula (I).
TITLE: Pyrazolopyridine-diamides, their use as insecticide and processes for preparing the same.
FIELD OF THE INVENTION:
The present invention relates to novel pyrazolopyridine-diamides, to their use as insecticides and acaricides, to their combination with other active compounds, and to processes for their preparation.
BACKGROUND:
Anthranilic acid derivatives having insecticidal properties have already been described in the literature. For example in W02001070671, W02003015518, W02003015519, W02003016284, W02003024222,
W02003016282, W02003016283, W02003062226, W02003027099, W02004027042, W02004033468, W02004046129, W02004067528, WO2005118552, W02005077934, W02005085234, W02006023783, W02006000336, W02006040113, W02006062978,
W02006111341, W02007006670, W02007020050, W02007024833, W02007020877, W02007144100, W02007043677, W02007093402, W02008010897, W02008070158, W02008072743, WO2008072745, W02008082502, WO2008126889, W02008126890, W02008126933, WO2010069502, WO2011157778, WO2011157654, WO2011157651, WO2011157663, WO2011157664, W02012010525, WO2012004221, WO2013007604,
W02013030100, W02014079820 and CN106810535.
Additionally, fused bicyclic anthranilic diamides are reported in the article titled“Bicyclic heterocyclic anthranilic diamides as ryanodine receptor modulators with insecticidal activity” published in Bioorganic and Medicinal Chemistry 24 (2016) 403-427.
The active compounds reported in the above literature have disadvantages in certain aspects, such as that they exhibit a narrow spectrum of application or they do not have satisfactory insecticidal or acaricidal activity.
SUMMARY:
The present invention relates to pyrazolopyridine-diamides which have now been found to be advantages over the compounds reported in the literature in either of improved insecticidal or acaricidal activity, biological or environmental properties, broader spectrum of application or enhanced plant compatibility.
The pyrazolopyridine-diamides of the present invention can be used in combination with other biologically active compounds for improving the efficacy particularly against insects which are difficult to control.
The present invention also relates to a plurality of processes for the preparation of pyrazolopyridine-diamides.
Accordingly, the present invention provides novel pyrazolopyridine-diamides of Formula (I),
wherein,
the definition of W1, W2, A1, A2, A3, B1, B2, D, Z1, E, R1, R2, R3, R4, m and n is as described in the following description.
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).
In the context of this disclosure “invertebrate pest control” means inhibition of invertebrate pest development (including mortality, feeding reduction, and/or mating disruption), and related expressions are defined analogously.
The term“agronomic” refers to the production of field crops such as for food 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“alkyl”, used either alone or in compound words such as“alkylthio” or“haloalkyl” or -N(alkyl) or alkylcarbonylalkyl or alkylsuphonylamino includes straight-chain or branched Ci to C24 alkyl, preferably Ci to C15 alkyl, more preferably Ci to C10 alkyl, most preferably Ci to Cr, 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-bimethylpropyl, 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 C2 to C24 alkenes, preferably C2 to C15 alkenes, more preferably C2 to C10 alkenes, most preferably C2 to Cr, 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, 1-methyl -2 -propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl- 1-butenyl, 2-methyl- 1-butenyl, 3-methyl- 1-butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3 -methyl-2 -butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3 -methyl-3 -butenyl, l,l-dimethyl-2-propenyl, 1,2-dimethyl- 1-propenyl, l,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-l-pentenyl, 4-methyl- 1-pentenyl, l-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4 -methyl -2-pentenyl, l-methyl-3-pentenyl, 2-methyl- 3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, l-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1 -dimethyl -2 -butenyl, l,l-dimethyl-3-butenyl, 1,2-dimethyl-l-butenyl, 1,2-dimethyl -2 -butenyl, l,2-dimethyl-3-butenyl, 1,3-dimethyl-l-butenyl, l,3-dimethyl-2-butenyl, l,3-dimethyl-3-butenyl, 2, 2-dimethy 1-3 -butenyl, 2,3-dimethyl-l-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, l-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.
Non-limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3 -methyl -1-butynyl, 1,1 -dimethyl-2 -prop ynyl, 1-ethyl -2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1 -methyl -2-pentynyl, l-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-l-pentynyl, 3-methyl-4-
pentynyl, 4-methyl-l-pentynyl, 4-methyl-2-pentynyl, 1,1 -dimethyl-2 -butynyl, l,l-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl, l-ethyl-2 -butynyl, l-ethyl-3-butynyl, 2-ethyl-3-butynyl and l-ethyl-l-methyl-2-propynyl and the different isomers. This definition also applies to alkynyl as a part of a composite substituent, for example haloalkynyl etc., unless specifically defined elsewhere. The term“alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
The term“cycloalkyl” means alkyl closed to form a ring. Non-limiting examples include cyclopropyl, cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as a part of a composite substituent, for example cycloalkylalkyl etc., unless specifically defined elsewhere.
The term“cycloalkenyl” means alkenyl closed to form a ring including monocyclic, partially unsaturated hydrocarbyl groups. Non-limiting examples include cyclopropenyl, cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as a part of a composite substituent, for example cycloalkenylalkyl etc., unless specifically defined elsewhere.
The term“cycloalkynyl” means alkynyl closed to form a ring including monocyclic, partially unsaturated groups. Non-limiting examples include cyclopropynyl, cyclopentynyl and cyclohexynyl. This definition also applies to cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere.
The term“cycloalkoxy”,“cycloalkenyloxy” and the like are defined analogously. Non limiting examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as a part of a composite substituent, for example cycloalkoxy alkyl etc., unless specifically defined elsewhere.
The term“mono- or bi- or tri- carbocyclyl” includes but is not limited to
a mono carbocylic ring such as cyclohexane;
bicarbocyclic ring includes but is not limited to fused bicyclic rings such as decahydronaphthalene and octahydro-lH-indene; bridged bicyclic rings such as bicyclo[4.3.1]decane and bicyclo[4.2.1]nonane; spiro cyclic rings such as spiro[4.5]decane and spiro[2.4]heptane; and
tricarbocyclic ring includes but is not limited fused tricyclic rings such as tetradecahydrobenzo[a]azulene; bridged tricyclic rings such as adamantanyl; spiro cyclic rings such as dispiro[2.0.44.l3]nonane and dispiro[4.0.56.l5]dodecane.
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-di chi oro-2, 2, 2-triflu oroethyl, and l,l,l-trifluoroprop-2-yl. This definition also applies to haloalkyl as a part of a composite substituent, for example haloalkylaminoalkyl etc., unless specifically defined elsewhere.
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-limiting examples of“haloalkylsulfinyl” include CF3S(0), CCES O), CF3CF[2S(0) and CF3CF2S(0). Examples of“haloalkylsulfonyl” include CF3S(0)2, CC13S(0)2, CF3CH2S(0)2 and CF3CF2S(0)2.
The term“hydroxy” means -OH, Amino means -NRR, wherein R can be H or any possible substituent such as alkyl. Carbonyl means -C(O)- , carbonyloxy means -OC(O)-, sulfinyl means SO, sulfonyl means S(0)2.
The term“alkoxy” used either alone or in compound words included Ci to C24 alkoxy, preferably Ci to C15 alkoxy, more preferably Ci to C10 alkoxy, most preferably Ci to Cr, 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-limiting examples of “alkoxyalkyl” include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2.
The term“alkoxyalkoxy” denotes alkoxy substitution on alkoxy.
The term“alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-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 cycloalky lalkylamino.
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 “alkoxycarbony lalkylamino” denotes alkoxy carbonyl substitution on alkyl amino. “Alkylcarbonylalkylamino” denotes alkyl carbonyl substitution on alkyl amino. The terms alkylthioalkoxycarbonyl, cycloalkylalkylaminoalkyl and the like are defined analogously.
Non-limiting examples of “alkylsulfinyl” include methylsulphinyl, ethylsulphinyl, propylsulphinyl, 1-methylethylsulphinyl, butylsulphinyl, 1-methylpropylsulphinyl, 2-methylpropylsulphinyl, 1,1-dimethylethylsulphinyl, pentylsulphinyl, 1-methylbutylsulphinyl, 2-methylbutylsulphinyl, 3-methylbutylsulphinyl, 2,2-dimethylpropylsulphinyl, 1-ethylpropylsulphinyl, hexylsulphinyl, 1,1-dimethylpropylsulphinyl, 1 ,2-dimethylpropylsulphinyl, 1-methylpentylsulphinyl, 2-methylpentylsulphinyl, 3-methylpentylsulphinyl, 4-methylpentylsulphinyl, 1 , 1 -dimethylbutylsulphinyl,
1.2-dimethylbutylsulphinyl, 1,3 -dimethylbutylsulphinyl, 2,2-dimethylbutylsulphinyl, 2,3-dimethylbutylsulphinyl, 3, 3 -dimethylbutylsulphinyl, 1 -ethylbutylsulphinyl, 2-ethylbutylsulphinyl, 1,1,2-trimethylpropylsulphinyl, 1,2,2-trimethylpropylsulphinyl, 1 -ethyl- 1-methylpropylsulphinyl and l-ethyl-2-methylpropylsulphinyl and the different isomers. The term“arylsulfinyl” includes Ar-S(O), wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphinyl as a part of a composite substituent, for example haloalkylsulphinyl etc., unless specifically defined elsewhere.
Non-limiting examples of “alkylsulfonyl” include methylsulphonyl, ethylsulphonyl, propylsulphonyl, 1-methylethylsulphonyl, butylsulphonyl, 1-methylpropylsulphonyl, 2-methylpropylsulphonyl, 1,1-dimethylethylsulphonyl, pentylsulphonyl, 1 -methylbutylsulphonyl, 2-methylbutylsulphonyl, 3-methylbutylsulphonyl, 2,2-dimethylpropylsulphonyl, 1-ethylpropylsulphonyl, hexylsulphonyl, 1,1-dimethylpropylsulphonyl, 1,2-dimethylpropylsulphonyl, 1-methylpentylsulphonyl, 2-methylpentylsulphonyl, 3 -methylpentylsulphonyl, 4-methylpentylsulphonyl, 1 , 1 -dimethylbutylsulphonyl,
1.2-dimethylbutylsulphonyl, 1,3-dimethylbutylsulphonyl, 2,2-dimethylbutylsulphonyl, 2,3-dimethylbutylsulphonyl, 3 ,3 -dimethylbutylsulphonyl, 1 -ethylbutylsulphonyl, 2-ethylbutylsulphonyl,
1.1.2-trimethylpropylsulphonyl, 1,2,2-trimethylpropylsulphonyl, 1 -ethyl- 1-methylpropylsulphonyl and 1-ethyl-2-methylpropylsulphonyl and the different isomers. The term“arylsulfonyl” includes Ar-S(0)2,
wherein Ar can be any carbocyle or heterocylcle. This definition also applies to alkylsulphonyl as a part of a composite substituent, for example alkylsulphonylalkyl etc., unless defined elsewhere.
“Alkylamino”,“dialkylamino”, and the like, are defined analogously to the above examples.
The term“carbocycle” includes“aromatic carbocyclic ring system” and“nonaromatic carbocylic ring system” or polycyclic or bicycbc (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“heteroaryl” or“aromatic heterocyclic” means 5 or 6-membered, fully unsaturated monocyclic ring system containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur; if the ring contains more than one oxygen atom, they are not directly adjacent; 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom as ring members, for example (but not limited thereto) furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,3,4-triazolyl, tetrazolyl; nitrogen-bonded 5-membered heteroaryl containing one to four nitrogen atoms, or benzofused nitrogen-bonded 5-membered heteroaryl containing one to three nitrogen atoms: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms as ring members and in which two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member may be bridged by a buta-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, 1,3-benzoxazol-4-yl, l,3-benzoxazol-5-yl, l,3-benzoxazol-6-yl and l,3-benzoxazol-7-yl; benzofused 6-membered heteroaryl which contains one to three nitrogen atoms: for example (but not limited to) quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-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“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” includes“aromatic heterocycle” or“heteroaryl ring 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(0)o-2, and or C ring member of the heterocycle may be replaced by C(=0), C(=S), C(=CR*R*) and C=NR*, * indicates integers.
The term“non-aromatic heterocycle” or“non-aromatic heterocyclic” means three- to fifteen-membered, preferably three- to twelve-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, l,2,4-oxadiazolidin-3-yl, l,2,4-oxadiazolidin-5-yl, l,2,4-thiadiazolidin-3-yl, l,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-l-yl, l,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, l,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-l-yl, l,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, pyrrolinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-l-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-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, 1,3,5-hexahydrotriazin-2-yl, l,2,4-hexahydrotriazin-3-yl, cycloserines, 2,3,4,5-tetrahydro[lH]azepin-l- or -2- or -3- or -4- or -5- or -6- or -7- yl, 3,4,5,6-tetra-hydro[2H]azepin-2- or -3- or -4- or -5- or -6- or-7-yl, 2, 3,4,7-tetrahydro[lH]azepin-l- or -2- or -3- or -4- or -5- or -6- or-7- yl, 2,3,6,7-tetrahydro[lH]azepin-l- or -2- or -3- or -4- or -5- or -6- or -7- yl, hexahydroazepin-1- or -2- or -3- or -4- yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[l H]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, 2,3,4,7-tetrahydro[lH]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, 2,3,6,7-tetrahydro[lH]oxepin-2- or -3- or -4- or -5- or -6- or -7- yl, hexahydroazepin-1- or -2- or -3- or -4- yl, tetra- and hexahydro-l,3-diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-l,3-oxazepinyl, tetra- and hexahydro-l,4-oxazepinyl, tetra- and hexahydro-1, 3-diox epinyl, tetra- and hexahydro-l,4-dioxepinyl. This definition also applies to heterocyclyl as a part of a composite substituent, for example heterocyclylalkyl etc., unless specifically defined elsewhere.
The term“Trialkylsilyl” includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom such as trimethylsilyl, triethyl sily 1 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(0)CH3, C CflCFbCFbCFF and C(0)CH(CH3)2. Non limiting examples of “alkoxycarbonyl” include CH30C(=0), CFFCFFOC^O), CFFCFFCFFOC^O), (CH3)2CH0C(=0) and the different butoxy -or pentoxycarbonyl isomers. Non-limiting examples of ‘‘ alky laminoc arbony G’ include CH3NHC(=0), CH3CH2NHC(=0), CH3CH2CH2NHC(=0),
(CH3)2CHNHC(=0) and the different butylamino -or pentylaminocarbonyl isomers. Non-limiting examples of“dialkylaminocarbonyl” include (CH3)2NC(=0), (CH3CH2)2NC(=0), CH3CH2(CH3)NC(=0), CH3CH2CH2(CH3)NC(=0) and (CH3)2CHN(CH3)C(=0). Non-limiting examples of “alkoxyalkylcarbonyl” include CH30CH2C(=0), CH30CH2CH2C(=0), CH3CH20CH2C(=0), CH3CH2CH2CH20CH2C(=0) and CH3CH20CH2CH2C(=0). Non-limiting examples of “alkylthioalkylcarbonyl” include CH3SCH2C(=0), CH3SCH2CH2C(=0), CH3CH2SCH2C(=0), CH3CH2CH2CH2SCH2C(=0) and CH3CH2SCH2CH2C(=0). The term haloalkylsufonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkyl amino and the like are defined analogously.
Non-limiting examples of“alkylaminoalkylcarbonyl” include CFFNFICFFC^O), CThNHCThCThC^O), CH3CH2NHCH2C(=0), CH3CH2CH2CH2NHCH2C(=0) and CH3CH2NHCH2CH2C(=0).
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, CFFCF^OCFF), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2. In the above recitations, when a compound of Formula (I) is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents. Further, when the subscript m in (R)m indicates an integer ranging from for example 0 to 4 then the number of substituents may be selected from the integers between 0 and 4 inclusive.
When a group contains a substituent which can be hydrogen, then, when this substituent is taken as hydrogen, it is recognized that said group is being un-substituted.
The embodiments herein and the various features and advantageous details thereof are explained with reference to the non-limiting embodiments in the description. Descriptions of well-known components and processing techniques are omitted so as to not unnecessarily obscure the embodiments herein. The examples used herein are intended merely to facilitate an understanding of ways in which the embodiments herein may be practiced and to further enable those of skilled in the art to practice the embodiments herein. Accordingly, the examples should not be construed as limiting the scope of the embodiments herein.
The description of the specific embodiments will so fully reveal the general nature of the embodiments herein that others can, by applying current knowledge, readily modify and/or adapt for various applications such specific embodiments without departing from the generic concept, and, therefore, such adaptations and modifications should and are intended to be comprehended within the meaning and range of equivalents of the disclosed embodiments. It is to be understood that the phraseology or terminology employed herein is for the purpose of description and not of limitation. Therefore, while the embodiments herein have been described in terms of preferred embodiments, those skilled in the art will recognize that the embodiments herein can be practiced with modification within the spirit and scope of the embodiments as described herein.
Any discussion of documents, acts, materials, devices, articles and the like that has been included in this specification is solely for the purpose of providing a context for the disclosure. It is not to be taken as an admission that any or all of these matters form a part of the prior art base or were common general knowledge in the field relevant to the disclosure as it existed anywhere before the priority date of this application.
The numerical values mentioned in the description and the description/claims though might form a critical part of the present invention of the present invention, any deviation from such numerical values shall still fall within the scope of the present invention if that deviation follows the same scientific principle as that of the present invention disclosed in the present invention. The inventive compound of the present invention may, if appropriate, be present as mixtures of different possible isomeric forms, especially of stereoisomers, for example E and Z, threo and erythro, and also optical isomers, but if appropriate also of tautomers. Both the E and the Z isomers, and also the threo and erythro isomers, and the optical isomers, any desired mixtures of these isomers and the possible tautomeric forms are disclosed and claimed.
The term “pest” for the purpose of the present disclosure includes but is not limited to fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, insects and rodents.
The term“plant” is understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which are protectable and non-protectable by plant breeders’ rights.
For the purpose of the present disclosure the term“plant” includes a living organism of the kind exemplified by trees, shrubs, herbs, grasses, ferns, and mosses, typically growing in a site, absorbing water and required substances through its roots, and synthesizing nutrients in its leaves by photosynthesis.
Examples of“plant” for the purpose of the present invention include 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 include but is not limited to cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and vegetables, ornamentals, any floricultural plants and other plants for use of human and animals.
The term“plant parts” is understood to mean all parts and organs of plants above and below the ground. For the purpose of the present disclosure the term plant parts includes but is not limited to cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots including taproots, lateral roots, root hairs, root apex, root cap, rhizomes, slips, shoots, fruits, fruit bodies, bark, stem, buds, auxiliary buds, meristems, nodes and internodes.
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.
The present invention relates to a compound of Formula (I),
The definition of each componenent of Formula (I) is provided herein below in detail.
A1, A2 and A3 are independently C or N, provided that all of A1, A2 and A3 simultaneously cannot be N. Particularly, A1 is N; A2 and A3 are C.
B1 and B2 are independently C or N, and at least one of B1 and B2 is N; provided that both of B1 and B2 simultaneously cannot be N. Particularly, B1 is N; and B2 is C.
R1 is NR10RU
R10 is selected from the group consisting of hydrogen, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-Ci-Ce alkyl, Ci-Ce haloalkyl, C3-C6 halocycloalkyl, Ci-Ce alkoxy and Ci-Ce haloalkoxy.
R11 is selected from the group consisting of hydrogen, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C12 mono- or bi- or tri- carbocyclyl ring or ring system, C3-C8 cycloalkyl-Ci-Ce alkyl, NRcRd and C3-C6 heterocyclyl; said heterocyclyl ring comprise one or more hetero atoms selected from N, O and S(0)o-2; and one or more C of the heterocyclyl ring may be replaced with C(=0), C(=S) and or C(=NR19); said heterocyclyl ring may be optionally substituted with one or more R16a.
Particularly, R11 is selected from the group consisting of hydrogen, C3-C12 mono- or bi- or tri- carbocyclyl ring or ring system, C3-C8 cycloalkylalkyl, andC3-Ce heterocyclyl; said heterocyclyl ring comprise one or more hetero atoms selected from N, O and S(0)o-2; and one or more C of the heterocyclyl ring may be replaced with C(=0) and C(=S); said heterocyclyl ring may be optionally substituted with one or more
Ri6a_
Each of R10 and R11 may be independently and optionally substituted with one or more substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, Ci -Cr, alkyl, C3-C8 cycloalkyl, C3-C6 heterocyclyl, C 1 -Cr, alkoxy, C 1 -Cr, haloalkoxy, Ci -Cr, alkylthio, C 1 -Cr, alkylsulfinyl, C 1 -Cr, alkylsulfonyl, C 1 -Cr, alkoxycarbonyl, Ci-Ce alkylcarbonyl, Ci-Ce trialkylsilyl, phenyl, benzoyl, phenoxy and 5- or 6-membered heteroaromatic rings.
Each of the phenyl, benzoyl, phenoxy, heterocyclyl ring and 5- or 6 membered heteroaromatic ring; may be optionally substituted with one or more substituents independently selected from the group consisting of Ci -Cr, alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, C 1 -Cr, haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, halogen, cyano, nitro, Ci -Cr, alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, Ci-Ce alkylamino, Ci-Cs dialkylamino, C3-C8 cycloalkylamino, C3-Cs-cycloalkyl, Ci-Cr, -alkylamino, Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl, Ci-Ce alkylaminocarbonyl, Ci-Cs dialkylaminocarbonyl, Ci-Ce trialkylsilyl, Ci-Ce alkoxy, Ci-Ce alkylamino, Ci-Cs dialkylamino, C3-C8 cycloalkylamino, Ci -Cr, alkoxycarbonyl and Ci-Ce alkylcarbonyl.
Alternatively, R10 and R1 1 together with N atom to which they are attached may form a 3 to 8- membered heterocyclyl ring; said heterocyclyl ring comprise one or more hetero atoms selected from N, O and S(0)o-2; and one or more C of the heterocyclyl ring may be replaced with C(=0) or C(=S) or C(=NR19); said heterocyclyl ring may be optionally substituted with one or more substituent R16b.
The substituents R16a, R16b and R16c are independently selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxy, Ci-Ce alkyl, CVCr, alkenyl, CVCr, alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, Ci-Ce alkoxyalkyl, Ci-Ce hydroxyalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce haloalkoxycarbonyl, Ci-Ce alkylthio, C i-Cr, haloalkylthio, Ci-Ce haloalkylsulfinyl, Ci-Ce haloalkylsulfonyl, Ci-Ce alkylsulfinyl, C 1 -Cr, alkylsulfonyl, Ci-Ce alkylamino, Ci-Ce dialkylamino, C3-C6 cycloalkylamino, Ci-Ce alkyl-C3-Ce-cycloalkylamino, Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl, Ci-Ce alkylaminocarbonyl, Ci-Ce dialkylaminocarbonyl, Ci-Ce alkoxycarbonyloxy, Ci-Ce alkylaminocarbonyloxy, Ci-Ce dialkylaminocarbonyloxy and Ci -Cr, trialkylsilyl.
Particularly, R1& is selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-Ce alkyl, C3-Cg cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, Ci-Ce alkoxyalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce haloalkylthio, and Ci-Ce haloalkylsulfinyl.
Alternatively,
Particularly,
R12 and R13 are independently selected from the group consisting of hydrogen, C1-C10 alkyl, C3-C8 cycloalkyl, C2-C10 alkenyl, C2-C10 alkynyl and Ci-Ce alkylcarbonyl, wherein R12 and R13 may be optionally substituted with one or more Re.
The substituent Re is selected from the group consisting of halogen, cyano, nitro, hydroxy, thio, thiocyanate, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl and C3-C8 cycloalkyl, wherein one or more CH2 groups may be replaced by a C(=0) group, wherein Re may be optionally substituted with halogen, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce alkyl sulfinyl, Ci-Ce alkylsulfonyl, Ci-Cehaloalkylthio, -ORa, -NRcRd, -S(0)aRa, -S(0)aNRcRd, -C(=0)Ra, -C(=0)NRcRd, -C(=0)0Rb, -C(=S)Ra, -C(=S)NRcRd, -C(=S)ORb, -C(=S)SRb, -C(=NRc)Rb, -C(=NRc)NRcRd, phenyl, benzyl, phenoxy and 4 - to 6- heterocyclyl; each of phenyl, benzyl, phenoxy and 3 - to 6- heterocyclyl may be optionally substituted with halogen, Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy and Ci-Ce haloalkoxy; or two vicinal radicals Re together form a group =0, =CH(CI-C6 alkyl), =C(Ci-C6 alkyl)Ci-C6-alkyl, =N(Ci-C6-alkyl) or =NO(Ci-C6-alkyl).
The substituents Ra, Rb, Rc and Rd are independently selected from the group consisting of Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C i -Cr, alkoxy, C i -Cr, alkylthio, C i -Cr, alkylsulfinyl, C i -Cr, alkylsulfonyl, wherein one or more CH2 groups may be replaced by a C(=0) group, and optionally substituted with halogen, Ci-Ce alkoxy, phenyl, benzyl, pyridyl and phenoxy, wherein phenyl, benzyl, pyridyl and phenoxy may be optionally substituted with halogen, Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkoxycarbonyl, Ci-Ce alkylamino and di-(Ci-C6-alkyl)amino.
The substituents Rc and Rd together with the nitrogen atom to which they are bound may form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or fully unsaturated heterocyclic ring or ring system which may contain at least one ring member selected from N, O and S(0)o-2, where the heterocyclic ring or ring system optionally may be substituted with halogen, Ci-Ce haloalkyl, Ci-Ce alkoxy or Ci-Ce haloalkoxy.
The substituents R12 and R13 represent phenyl, benzyl, phenoxy and 3 - to 6- heterocyclyl; each of R12 and R13 may be optionally substituted with halogen, cyano, nitro, hydroxy, -SH, -SCN, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, wherein one or more CH2 groups may be replaced by a C(=0) group.
Particularly, R12 and R13 are independently selected from the group consisting of hydrogen, C1-C10 alkyl, C3-C8 cycloalkyl, C2-C10 alkenyl, C2-C10 alkynyl and Ci-Ce alkylcarbonyl.
Alternatively, the substituents R12 and R13 together represent a C2-C7 alkylene, C2-C7 alkenylene, C6-C9 alkynylene, 3 to 10 membered ring or ring system together with the sulfur atom to which they are attached, wherein 1 to 4 of the CH2 groups in the C2-C7 alkylene chain or 1 to 4 of any of the CH2 or CH groups in the C2-C7 alkenylene chain or 1 to 4 of any of the CH2 groups in the C6-C9 alkynylene chain
may be replaced by 1 to 4 groups independently selected from C(=0), C(=S), O, N, NO and S(0)o-2 and NH, and wherein the carbon and/or nitrogen atoms in the C2-C7 alkylene, C2-C7 alkenylene or C6-C9 alkynylene ring may be substituted with one or more substituent independently selected from halogen, cyano, Ci-Ce-alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce haloalkylthio, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl and C2-C6 haloalkynyl.
The substituent R14 is selected from the group consisting of hydrogen, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, Ci-Ce alkylcarbonyl, Ci-Ce alkylaminocarbonyl, Ci-Ce alkoxycarbonyl, Ci-Ce haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C10 cycloalkenyl, phenyl, naphthyl, 3- to 8- membered ring or ring system which may contain one or more ring member selected from C, N, O and S(0)o-2; each of which is optionally substituted with one or more group selected from halogen, Ci-Ce alkoxy, Ci-Ce alkylthio, Ci-Ce haloalkyl, cyano, nitro, formyl, Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl, Ci-Ce alkylaminocarbonyl, di(Ci-Ce alkylaminocarbonyl, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, trifluoromethylsulfonyl, C3-C8 cycloalkyl, and phenyl or naphthyl, wherein phenyl or naphthyl is optionally substituted with one or more group selected from halogen, Ci-Ce alkyl, Ci-Ce alkoxy, Ci-Ce haloalkyl, Ci-Ce alkyloxycarbonyl, trifluoromethylsulfonyl, formyl, nitro and cyano.
W1 and W2 are independently O or S. Particularly, W1 and W2 are O.
The substituents R2 and R3 are independently selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxy, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxyalkyl, Ci-Ce hydroxyalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-Cr, halocycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce haloalkoxycarbonyl, Ci-Ce alkylthio, Ci-Ce haloalkylthio, Ci-Ce haloalkylsulfinyl, Ci-Ce haloalkylsulfonyl, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, Ci-Ce alkylamino, Ci-Cr, dialkylamino, C3-C6 cycloalkylamino, Ci-Ce alkyl-C3-C6-cycloalkylamino, Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl, Ci-Ce alkylaminocarbonyl, Ci-Ce dialkylaminocarbonyl, Ci-Ce alkoxycarbonyloxy, Ci-Ce alkylaminocarbonyloxy, Ci-Ce dialkylaminocarbonyloxy, Ci-Ce trialkylsilyl, amino, formyl, C2-C6 cyanoalkenyl, phenylcarbonylamino, phenyloxycarbonyl, wherein each substituent may optionally be substituted with halogen, cyano, nitro, hydroxy, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, Ci-Ce alkoxyalkyl, Ci-Ce hydroxyalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce haloalkylthio, Ci-Ce haloalkylsulfinyl, Ci-Ce haloalkylsulfonyl, Ci-Ce alkylsulfinyl, Ci-Cr, alkylsulfonyl, Ci-Ce alkylamino, Ci-Ce dialkylamino, C3-C6 cycloalkylamino, Ci-Ce alkyl-C3-C6
cycloalkylamino, Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl, Ci-Ce alkylaminocarbonyl, Ci-Ce dialkylaminocarbonyl, Ci-Ce alkoxycarbonyloxy, Ci-Ce alkylaminocarbonyloxy, Ci-Ce dialkylaminocarbonyloxy and C i -Cr, trial ky Is i ly I .
Particularly, R2 and R3 are independently selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxy, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-Ci-Ce alkyl, CVCr, haloalkyl, CVCr, alkoxy, CVCr, haloalkoxy, CVCr, alkylthio, and CVCr, haloalkylthio
Alternatively, each of R2 and R3 are independently selected from the group consisting of phenyl, benzyl, phenoxy or 4- to 6- heterocyclyl; each phenyl, benzyl, phenoxy or 4- to 6- heterocyclyl may optionally be substituted with one or more substituent selected from halogen, cyano, nitro, hydroxy, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, Ci-Ce alkoxyalkyl, Ci-Cr, hydroxyalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, Ci-Ce alkoxy, Ci-Ce alkylthio, Ci-Ce haloalkylthio, Ci-Ce haloalkylsulfinyl, Ci-Ce haloalkylsulfonyl, Ci-Ce alkylsulfinyl, Ci-Cr, alkylsulfonyl, Ci-Ce alkylamino, Ci-Ce dialkylamino, C3-C6 cycloalkylamino, Ci-Ce alkyl-C3-C6-cycloalkylamino, Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl, Ci-Ce alkylaminocarbonyl, Ci-Ce dialkylaminocarbonyl, Ci-Ce alkoxycarbonyloxy, Ci-Ce alkylaminocarbonyloxy, Ci-Ce dialkylaminocarbonyloxy and Ci-Ce trialkylsilyl; 2-, 3- or 4 pyridylcarbonylamino which can be mono-, di- or tri- substituted by halogen, cyano, nitro, hydroxy, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, Ci-Ce alkoxyalkyl, Ci-Ce hydroxyalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, C i -Cr, haloalkylthio, C i -Cr, haloalkylsulfinyl, Ci-Ce haloalkylsulfonyl, Ci-Ce alkylsulfinyl, C i -Cr, alkylsulfonyl, Ci-Ce alkylamino, Ci-Ce dialkylamino, C3-C6 cycloalkylamino, Ci-Ce alkyl-C3-C6 cycloalkylamino, Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl, Ci-Ce alkylaminocarbonyl, Ci-Ce dialkylaminocarbonyl, Ci-Ce alkoxycarbonyloxy, Ci-Ce alkylaminocarbonyloxy, Ci-Ce dialkylaminocarbonyloxy and Ci-Ce trialkylsilyl; Ci-Ce alkoxycarbonylamino, Ci-Ce alkylaminocarbonylamino, C i - C r, d i a I k y I a m i n oc a r bo n y I a m i n o , Ci-Cehaloalkylcarbonyl and RxON=C(Ry). Rx and Ry independently are hydrogen or C Cr, alkyl.
The integer“n” is ranging from 0 to 3.
The integer“m” is ranging from 0 to 2.
The substituent R4 is selected from the group consisting of hydrogen, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, Ci-Ce alkylcarbonyl and Ci-Ce alkoxycarbonyl; each of Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl may optionally be substituted by one or more substituents selected from halogen nitro, cyano, hydroxy, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce haloalkylthio, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, Ci-Ce alkylamino, Ci-Ce dialkylamino, C3-C8 cycloalkyl, C3-C6 cycloalkylamino and Ci-Ce alkyl-C3-Ce cycloalky lamino.
Particularly, R4 is selected from the group consisting of hydrogen, C1-C3 alkyl, and C3-C5 cycloalkyl. More particularly, R4 is hydrogen.
D is selected from the group consisting of,
wherein;
the bond on the left is attached to Z1 and the bond on the right is attached to carbon marked with 2, or the bond on the right is attached to Z1 and the bond on the left is attached to carbon marked with 2.
Particularly, D is D4 and the bond on the right is attached to Z1 and the bond on the left is attached to
carbon marked with 2. More particularly, D is 04-1 wherein;
the bond on the right is attached to Z1 and the bond on the left is attached to carbon marked with 2.
The substituents R8 and R9 may be attached to one or more possible position/s of D.
The substituent R8 is selected from the group consisting of hydrogen, Ci-Ce alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Cr, haloalkyl, halogen, cyano, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkoxycarbonyl, Ci-Ce alkylthio, Ci-Ce haloalkylthio, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, Ci-Ce haloalkylsulfinyl and Ci-Ce haloalkylsulfonyl.
Particularly, R8 is selected from the group consisting of hydrogen, C1-C4 alkyl, C3-C5 cycloalkyl, halogen, cyano, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, and C1-C4 haloalkylthio. More particularly, R8 is hydrogen.
The substituent R9 is selected from a phenyl ring, a benzyl ring, a 5- or 6-membered heteroaromatic ring, a naphthyl ring system or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring or ring system optionally substituted with one or more substituent independently selected from the group consisting of halogen, Ci-Ce alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, cyano, nitro, Ci-Ce alkoxy, C 1 -Cr, haloalkoxy, Ci-Ce alkoxycarbonyl, Ci-Ce alkylthio, Ci-Ce haloalkylthio, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, Ci-Ce haloalkylsulfinyl, Ci-Ce haloalkylsulfonyl, Ci-Ce alkylamino, Ci-Cs dialkylamino, C3-C6 cycloalkylamino, C3-C8 cycloalkyl-Ci-Ce-alklyamino, Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl, C 1 -Cr, alkylaminocarbonyl, Ci-Cs dialkylaminocarbonyl and Ci-Ce trialkylsilyl.
Particularly, R9 is selected from a phenyl ring, a benzyl ring, a 5- or 6-membered heteroaromatic ring, each ring or ring system optionally substituted with one or more substituent independently selected from the group consisting of halogen, Ci-Ce alkyl, Ci-Ce haloalkyl, cyano, and nitro. More particularly, R9 is selected from a 6-membered heteroaromatic ring optionally substituted with one or more halogen.
Z1 is a direct bond or CR6R7 or C(O) or NR18 or O or S(0)o-2- Particularly, Z1 is a direct bond or CR6R7 or
O.
The substituents R6 and R7 are independently selected from the group consisting of hydrogen, halogen, cyano, hydroxy, formyl, Ci-Ce alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-Ce haloalkyl, C2-C6 haloalkenyl, C2-C4 haloalkynyl, C 1 -Cr, alkoxyalkyl, Ci-Ce alkylthioalkyl, C 1 -Cr, alkylsulfinylalkyl, C 1 -Cr, alkylsulfonylalkyl, Ci-Ce alkylcarbonyl, Ci-Ce haloalkylcarbonyl, Ci-Ce alkoxycarbonyl, Ci-Ce a I k o x y c a r b o n y I - C 1 - C r, - a I k y I , Ci-Ce alkylaminocarbonyl, Ci-Ce alkylthio, Ci-Ce haloalkylthio, Ci-Ce alkylsulfinyl, Ci-Ce haloalkylsulfinyl, dialkylaminocarbonyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C3-Cg cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce alkylsulfonyl and Ci-Ce haloalkylsulfonyl.
Particularly, R6 and R7 are independently selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C1-C4 alkyl, and C1-C4 haloalkyl.
The substituents R18 and R19 are independently selected from the group consisting of hydrogen, halogen, cyano, hydroxy, formyl, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, Ci-Ce alkoxyalkyl, Ci-Ce hydroxyalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-C e- alkylcarbonyl, Ci-Ce haloalkoxycarbonyl, Ci-Ce alkylthio, Ci-Ce haloalkylthio, Ci-Ce haloalkylsulfinyl, Ci-Ce haloalkylsulfonyl, Ci-Ce alkylsulfinyl and Ci-Ce alkylsulfonyl.
E is selected from the group consisting of hydrogen, halogen, cyano, Ci-Ce alkyl, C3-C6 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy or Ci-Ce haloalkoxy, C3-C6 heterocyclyl; said heterocyclyl ring comprise one or more hetero atoms selected from N, O and S(0)o-2; and one or more C of the heterocyclyl ring or ring system may be replaced with C(=0), C(=S) or C(=NR19); said heterocyclyl ring may be optionally substituted with one or more R16c.
Particularly, E is selected from the group consisting of halogen, Ci-Ce haloalkyl, or Ci-Ce alkoxy, C3-C6 heterocyclyl; said heterocyclyl ring comprise one or more hetero atoms selected from N, O and S(0)o-2; said heterocyclyl ring may be optionally substituted with one or more R16c.
Alternatively, E is selected from 5- or 6- membered aromatic or heteroaromatic ring or 8-, 9- or 10-membered heterobicyclic ring systems, wherein the heteroatoms in heteroaromatic ring may be selected from N, O and S; wherein the heteroatoms in heterobicyclic ring systems may be selected from N, O and S(0)o-2; and C atom of the heterobicyclic ring system may be replaced with C(=0), C(=S) or C(=NR19); wherein the aromatic, heteroaromatic or heterobicyclic ring or the ring system may be optionally substituted with hydrogen, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, halogen, cyano, carboxyl, aminocarboxyl, nitro, hydroxy, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulphonyl, Ci-Ce haloalkylthio, Ci-Ce haloalkylsulfinyl, Ci-Ce haloalkylsulfonyl, phenyl or a 5- or 6- membered heteroaromatic ring; wherein said phenyl or the heteroaromatic ring is optionally substituted with one or more group selected from Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-Cr, halocycloalkyl, halogen, cyano, carboxyl, aminocarboxyl, nitro, hydroxy, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulphonyl, Ci-Ce haloalkylthio, Ci-Ce haloalkylsulfinyl, Ci-Ce haloalkylsulfonyl.
Particularly, E is 5- or 6- membered heteroaromatic ring, wherein the heteroatoms in heteroaromatic ring may be selected from one or more N, O and S; and heteroaromatic ring may be optionally substituted with hydrogen, Ci-Ce alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, C3-C6 halocycloalkyl, halogen, cyano, carboxyl, aminocarboxyl nitro, hydroxy, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, C 1 -Cr, alkylsulfinyl, Ci-Ce alkylsulphonyl, Ci-Ce haloalkylthio, Ci-Ce haloalkylsulfinyl, and Ci-Ce haloalkylsulfonyl.
More particularly, E is 5- membered heteroaromatic ring, wherein the heteroatoms in heteroaromatic ring may be selected from one or more N, O and S; and heteroaromatic ring may be optionally substituted with C 1 -Cr, alkyl, Ci-Ce haloalkyl, halogen, cyano, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, and Ci-Ce haloalkylthio.
The present invention also relates to the salts, metal complexes, N-oxides, isomers or polymorphs of compound of Formula (I).
AMENDED CLAIMS
received by the International Bureau on 18.04.2019
CLAIMS:
1. A compound of Formula (I),
wherein;
A1, A2 and A3 are independently C or N, provided that all of A1, A2 and A3 simultaneously cannot be N;
B1 and B2 are independently C or N, and at least one of B1 and B2 is N; provided that both of B1 and B2 simultaneously cannot be N;
R1 is NR10RU;
R10 is selected from the group consisting of hydrogen, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalky l-Ci -Cr, alkyl, C 1 -Cr, haloalkyl, C3-C6 halocycloalkyl, Ci-Cr, alkoxy and Ci-Cr, haloalkoxy;
R1 1 is selected from the group consisting of hydrogen, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C12 mono- or bi- or tri- carbocyclyl ring or ring system, C3-C8 cycloalkylalkyl, NRcRd and C3-C6 heterocyclyl; said heterocyclyl ring comprise one or more hetero atoms selected from N, O and S(0)o-2; and one or more C of the heterocyclyl ring may be replaced with C(=0), C(=S) and or C(=NR19); said heterocyclyl ring may be optionally substituted with one or more R16a;
each of R10 and R11 may be independently and optionally substituted with one or more substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, Ci-Ce alkyl, C3-C8 cycloalkyl, C3-C6 heterocyclyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Cr, alkylthio, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, Ci-Ce alkoxycarbonyl, Ci-Ce alkylcarbonyl, Ci-Ce trialkylsilyl, phenyl, benzoyl, phenoxy and 5- or 6- membered heteroaromatic rings;
each phenyl, benzoyl, phenoxy, heterocyclyl ring; may be optionally substituted with one or more substituents independently selected from the group consisting of Ci -Cr, alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3- Cr, halocycloalkyl, halogen, cyano, nitro, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, Ci-Ce alkylamino, Ci-Cs dialkylamino, C3-C8 cycloalkylamino, C3-Cs-cycloalkyl, Ci -Cr, -alkylamino, Ci- Cr, alkylcarbonyl, Ci-Ce alkoxycarbonyl, Ci-Ce alkylaminocarbonyl, Ci-Cs dialkylaminocarbonyl, Ci-Ce trialkylsilyl, Ci-Ce alkoxy, Ci-Ce alkylamino, Ci-Cs dialkylamino, C3-C8 cycloalkylamino, Ci-Ce alkoxycarbonyl and Ci-Ce alkylcarbonyl; or
R10 and R11 together with N atom to which they are attached may form a 3 to 8-membered heterocyclyl ring; said heterocyclyl ring comprise one or more hetero atoms selected from N, O and S(0)o-2; and one or more C of the heterocyclyl ring may be replaced with C(=0) or C(=S) or C(=NR19); said heterocyclyl ring may be optionally substituted with one or more substituent R16b;
wherein R16a, R16b and R16c are independently selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxy, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, Ci-Ce alkoxyalkyl, Ci-Ce hydroxyalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C 1 - C r, h a I o a I k o x y c a r b o n y I , Ci-Ce alkylthio, Ci-Ce haloalkylthio, Ci-Ce haloalkylsulfinyl, Ci-Ce haloalkylsulfonyl, C 1 -Cr, alkylsulfinyl, Ci-Ce alkylsulfonyl, Ci-Ce alkylamino, Ci-Ce dialkylamino, C3-C6 cycloalkylamino, Ci-Ce alkyl-C3-C6-cycloalkylamino, Ci-Ce alkylcarbonyl, C 1 -Cr, alkoxycarbonyl, Ci-Ce alkylaminocarbonyl, Ci-Ce dialkylaminocarbonyl, C 1 -Cr, alkoxycarbonyloxy, Ci-Ce alkylaminocarbonyloxy, Ci-Ce dialkylaminocarbonyloxy and Ci-Ce trialkylsilyl;
R12 and R13 are independently selected from the group consisting of hydrogen, C1-C10 alkyl, C3-C8 cycloalkyl, C2-C10 alkenyl, C2-C10 alkynyl and Ci-Ce alkylcarbonyl, wherein R12 and R13 may be optionally substituted with one or more Re,
each Re is selected from the group consisting of halogen, cyano, nitro, hydroxy, thio, thiocyanate, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl and C3-C8 cycloalkyl, wherein one or more CH2 groups may be replaced by a C(=0) group, wherein Re may be optionally substituted with halogen, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci- Cr, alkylthio, C 1 -Cr, alkylsulfinyl, C 1 -Cr, alkylsulfonyl, Ci-Ce haloalkylthio, -OR",
phenyl, benzyl, phenoxy and 4 - to 6- heterocyclyl; each of phenyl, benzyl, phenoxy and 3 - to 6- heterocyclyl may be optionally substituted with halogen, C 1 -Cr, alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy and Ci-Ce haloalkoxy; or two vicinal radicals Re together form a group =0, =CH(Ci-Ce alkyl), =C(Ci-Ce alkyl)Ci-Ce- alkyl, =N(Ci-C6-alkyl) or =NO(Ci-C6-alkyl);
R", Rb, Rc and Rd are independently selected from the group consisting of C 1 -Cr, alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C 1 -Cr, alkoxy, Ci-Ce alkylthio, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, wherein one or more CH2 groups may be replaced by a C(=0) group, and optionally substituted with halogen, Ci-Ce alkoxy, phenyl, benzyl, pyridyl and phenoxy, wherein phenyl, benzyl, pyridyl and phenoxy may be optionally substituted with halogen, Ci-Ce alkyl, Ci-Ce haloalkyl, Ci- Cr> alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkoxycarbonyl, Ci-Ce alkylamino and di-(Ci-C6-alkyl)amino;
Rc and Rd together with the nitrogen atom to which they are bound may form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or fully unsaturated heterocyclic ring or ring system which may contain at
least one ring member selected from N, O and S(0)o-2, where the heterocyclic ring or ring system optionally may be substituted with halogen, CVCr, haloalkyl, CVCr, alkoxy or CVCr, haloalkoxy;
R12 and R13 represent phenyl, benzyl, phenoxy and 3 - to 6- heterocyclyl; each of R12 and R13 may be optionally substituted with halogen, cyano, nitro, hydroxy, -SH, -SCN, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, wherein one or more CH2 groups may be replaced by a C(=0) group; or
R12 and R13 together represent a C2-C7 alkylene, C2-C7 alkenylene, C6-C9 alkynylene, 3 to 10 membered ring or ring system together with the sulfur atom to which they are attached, wherein 1 to 4 of the CH2 groups in the C2-C7 alkylene chain or 1 to 4 of any of the CH2 or CH groups in the C2-C7 alkenylene chain or 1 to 4 of any of the CH2 groups in the C6-C9 alkynylene chain may be replaced by 1 to 4 groups independently selected from C(=0), C(=S), O, N, NO and S(0)o-2 and NH, and wherein the carbon and/or nitrogen atoms in the C2-C7 alkylene, C2-C7 alkenylene or C6-C9 alkynylene ring may be substituted with one or more substituent independently selected from halogen, cyano, Ci-Cr, -alkyl, C Cr, haloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce haloalkylthio, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl and C2-C6 haloalkynyl;
R14 is selected from the group consisting of hydrogen, C 1 -Cr, alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C 1 -Cr, alkylcarbonyl, C 1 -Cr, alkylaminocarbonyl, C 1 -Cr, alkoxycarbonyl, C 1 -Cr, haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C10 cycloalkenyl, phenyl, naphthyl, 3- to 8- membered ring or ring system which may contain one or more ring member selected from C, N, O and S(0)o-2; each of which is optionally substituted with one or more group selected from halogen, Ci-Ce alkoxy, CVCr, alkylthio, C 1 -Cr, haloalkyl, cyano, nitro, formyl, C 1 -Cr, alkylcarbonyl, C 1 -Cr, alkoxycarbonyl, C 1 -Cr, alkylaminocarbonyl, di(Ci-Ce alkylaminocarbonyl, C 1 -Cr, alkylsulfinyl, C 1 -Cr, alkylsulfonyl, trifluoromethylsulfonyl, C3-C8 cycloalkyl, and phenyl or naphthyl, wherein phenyl or naphthyl is optionally substituted with one or more group selected from halogen, CVCr, alkyl, C 1 -Cr, alkoxy, CVCr, haloalkyl, CVCr, alkyloxycarbonyl, trifluoromethylsulfonyl, formyl, nitro and cyano;
W1 and W2 are independently O or S;
each of R2 and R3 are independently selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxy, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-Ci -Cr, alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxyalkyl, Ci-Ce hydroxyalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce haloalkoxycarbonyl, Ci-Ce alkylthio, Ci-Ce haloalkylthio, Ci-Ce haloalkylsulfinyl. Ci-Ce haloalkylsulfonyl, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, Ci-Cr, alkylamino, Ci-Ce dialkylamino, C3-C6 cycloalkylamino, Ci-Ce alkyl-C3-C6-cycloalkylamino, Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl, Ci-Ce alkylaminocarbonyl, Ci-Ce dialkylaminocarbonyl, Ci-Ce alkoxycarbonyloxy, Ci-Ce alkylaminocarbonyloxy, Ci-Ce dialkylaminocarbonyloxy or Ci-Ce trialkylsilyl, amino, formyl, C2-C6 cyanoalkenyl, phenylcarbonylamino, phenyloxycarbonyl, wherein each of may optionally substituted with halogen, cyano, nitro, hydroxy, Ci-Ce alkyl, C2-Cr, alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, Ci-Ce alkoxyalkyl, Ci-Ce hydroxyalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, Ci-Cr, alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce haloalkylthio, Ci-Ce haloalkylsulfinyl, Ci-Ce haloalkylsulfonyl, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, Ci-Ce alkylamino, Ci-Ce dialkylamino, C3-C6 cycloalkylamino, Ci-Ce alkyl-C3-Ce cycloalkylamino, Ci-Ce alkylcarbonyl, C 1 -Cr, alkoxycarbonyl, Ci-Ce alkylaminocarbonyl, Ci-Ce dialkylaminocarbonyl, Ci-Ce alkoxycarbonyloxy, Ci-Ce alkylaminocarbonyloxy, Ci-Ce dialkylaminocarbonyloxy and Ci-Ce trialkylsilyl; or
each of R2 and R3 are independently selected from the group consisting of phenyl, benzyl, phenoxy or 4- to 6- heterocyclyl; each phenyl, benzyl, phenoxy or 4- to 6- heterocyclyl substituted with one or more substituent selected from halogen, cyano, nitro, hydroxy, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, C 1 -Cr, haloalkyl, Ci-Ce alkoxyalkyl, Ci-Ce hydroxyalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, C 1 -Cr, alkoxy, , Ci-Ce alkylthio, Ci-Ce haloalkylthio, Ci-Ce haloalkylsulfinyl, Ci-Ce haloalkylsulfonyl, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, Ci-Ce alkylamino, Ci-Ce dialkylamino, C3-C6 cycloalkylamino, Ci-Ce alkyl-C3-C6-cycloalkylamino, Ci-Ce alkylcarbonyl, C 1 -Cr, alkoxycarbonyl, Ci-Ce alkylaminocarbonyl, Ci-Ce dialkylaminocarbonyl, Ci-Ce alkoxycarbonyloxy, Ci-Ce alkylaminocarbonyloxy, Ci-Ce dialkylaminocarbonyloxy and Ci-Ce trialkylsilyl; 2-, 3- or 4 pyridylcarbonylamino which can be mono-, di- or tri- substituted by halogen, cyano, nitro, hydroxy, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, Ci-Ce alkoxyalkyl, Ci-Ce hydroxyalkyl, C2-C6 haloalkenyl, C2-Cr, haloalkynyl, C3-C6 halocycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce haloalkylthio, C 1 -Cr, haloalkylsulfinyL C 1 -Cr, haloalkylsulfonyl, C 1 -Cr, alkylsulfinyl, C 1 -Cr, alkylsulfonyl, Ci-Ce alkylamino, Ci-Ce dialkylamino, C3-C6 cycloalkylamino, Ci-Ce alkyl-C3-C6 cycloalkylamino, Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl, Ci-Ce alkylaminocarbonyl, Ci-Ce dialkylaminocarbonyl, Ci-Ce alkoxycarbonyloxy, Ci-Ce alkylaminocarbonyloxy, Ci-Ce dialkylaminocarbonyloxy and Ci-Ce trialkylsilyl; Ci-Ce alkoxycarbonylamino, Ci-Ce alkylaminocarbonylamino, Ci-Ce dialkylaminocarbonylamino, Ci-Ce haloalkylcarbonyl and RxON=C(Ry);
wherein, Rx and Ry independently are hydrogen or C Cr, alkyl;
“n” is an integer ranging from 0 to 3 ;
“m” is an integer ranging from 0 to 2;
R4 is selected from the group consisting of hydrogen, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, Ci-Ce alkylcarbonyl and Ci-Ce alkoxycarbonyl; each of Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl substituted by one or more substituents selected from halogen nitro, cyano, hydroxy, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce haloalkylthioCi-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, Ci-Ce alkylamino, Ci-Ce dialkylamino, C3-C8 cycloalkyl, C3-C6 cycloalkylamino and Ci-Ce alkyl-C3-C6 cycloalkylamino;
D is selected from the group consisting of,
wherein;
the bond on the left is attached to Z1 and the bond on the right is attached to carbon marked with 2, or
the bond on the right is attached to Z1 and the bond on the left is attached to carbon marked with 2; and
R8 and R9 may be attached to one or more possible position/s,
R8 is selected from the group consisting of hydrogen, Ci-Ce alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, halogen, cyano, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkoxycarbonyl, Ci-Ce alkylthio, Ci-Ce haloalkylthio, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, C 1 -Cr, haloalkylsulfinyl and Ci-Ce haloalkylsulfonyl;
R9 is selected from a phenyl ring, a benzyl ring, a 5- or 6-membered heteroaromatic ring, a naphthyl ring system or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring or ring system optionally substituted with one or more substituent independently selected from the group consisting of halogen, Ci-Ce alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, cyano, nitro, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkoxycarbonyl, Ci-Ce alkylthio, Ci-Ce haloalkylthio, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, Ci-Ce haloalkylsulfinyl, C 1 -Cr, haloalkylsulfonyl, Ci-Ce alkylamino, Ci-Cs dialkylamino, C3-C6 cycloalkylamino, C3-C8 cycloalkyl-Ci-Ce-alklyamino, Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl, Ci-Ce alkylaminocarbonyl, Ci-Cs dialkylaminocarbonyl and Ci-Ce trialkylsilyl;
} is a direct bond or CR6R7 or C(O) or NR18 or O or S(0)o-2;
R6 and R7 are independently selected from the group consisting of hydrogen, halogen, cyano, hydroxy, formyl, Ci-Ce alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-Ce haloalkyl, C2- Cr, haloalkenyl, C2-C4 haloalkynyl, Ci-Ce alkoxyalkyl, Ci-Ce alkylthioalkyl, Ci- Cr, alkylsulfinylalkyl, Ci-Ce alkylsulfonylalkyl, Ci-Ce alkylcarbonyl, Ci-Ce haloalkylcarbonyl, Ci-Ce alkoxycarbonyl, Ci-Ce alkoxycarbonyl-Ci-Ce-alkyl, Ci-Ce alkylaminocarbonyl, Ci-Ce alkylthio, Ci-Ce haloalkylthio, Ci-Ce alkylsulfinyl, Ci-Ce haloalkylsulfinyl, dialkylaminocarbonyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C3- Ce cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce alkylsulfonyl and Ci-Ce haloalkylsulfonyl;
R18 and R19 are independently selected from the group consisting of hydrogen, halogen, cyano, hydroxy, formyl, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3- Ce cycloalkylalkyl, Ci-Ce haloalkyl, Ci-Ce alkoxyalkyl, Ci-Ce hydroxyalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C 1 -CVal ky lcarbony I, Ci-Ce haloalkoxycarbonyl, Ci-Ce alkylthio, Ci-Ce haloalkylthio, Ci- Cr, haloalkylsulfinyl, Ci-Ce haloalkylsulfonyl, Ci-Ce alkylsulfinyl and Ci-Ce alkylsulfonyl;
E is selected from the group consisting of hydrogen, halogen, cyano, Ci-Ce alkyl, C3-C6 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy or Ci-Ce haloalkoxy, C3-C6 heterocyclyl; said heterocyclyl ring comprise one or more hetero atoms selected from N, O and S(0)o-2; and one or more C of the heterocyclyl ring or ring system may be replaced with C(=0), C(— S) or C(=NR19); said heterocyclyl ring may be optionally substituted with one or more R16c; or E is selected from 5- or 6- membered aromatic or heteroaromatic ring or 8-, 9- or 10-membered heterobicyclic ring systems, wherein the heteroatoms in heteroaromatic ring may be selected from N, O and S; wherein the heteroatoms in heterobicyclic ring systems may be selected from N, O and S(0)o-2; and C atom of the heterobicyclic ring system may be replaced with C(=0), C(=S) or C(=NR19); wherein the aromatic, heteroaromatic or heterobicyclic ring or the ring system may be optionally substituted with hydrogen, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3- Cr, halocycloalkyl, halogen, cyano, carboxyl, aminocarboxyl nitro, hydroxy, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulphonyl, Ci-Ce haloalkylthio, Ci-Ce haloalkylsulfinyl, Ci-Ce haloalkylsulfonyl, phenyl or a 5- or 6- membered heteroaromatic ring; wherein said phenyl or the heteroaromatic ring is optionally substituted with one or more group selected from Ci -Cr, alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, C 1 -Cr, haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, halogen, cyano, carboxyl, aminocarboxyl nitro, hydroxy, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulphonyl, Ci-Ce haloalkylthio, Ci-Ce haloalkylsulfinyl, Ci-Ce haloalkylsulfonyl;
or salts, metal complexes, N-oxides, isomers or polymorphs thereof;
provided that the following compound is excluded from the definition of Formula (I),
7-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N, 3-dimethyl- [l,2,4]triazolo[4,3-a]pyridine-8-carboxamide.
2. The compound according to claim 1, wherein
A1 is N; A2 and A3 are C;
B1 is N; and B2 is C;
R1 is NR10RU;
R10 is selected from the group consisting of hydrogen, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalky l-Ci -Cr, alkyl, C 1 -Cr, haloalkyl, C3-C6 halocycloalkyl, Ci-Cr, alkoxy and Ci-Cr, haloalkoxy;
R11 is selected from the group consisting of hydrogen, C3-C12 mono- or bi- or tri- carbocyclyl ring or ring system, C3-C8 cycloalkylalkyl, and C3-C6 heterocyclyl; said heterocyclyl ring comprise one or more hetero atoms selected from N, O and S(0)o-2; and one or more C of the heterocyclyl ring may be replaced with C(=0) and C(=S); said heterocyclyl ring may be optionally substituted with one or more R1&;
R12 and R13 are independently selected from the group consisting of hydrogen, C1-C10 alkyl, C3-C8 cycloalkyl, C2-C10 alkenyl, C2-C10 alkynyl and Ci-Ce alkylcarbonyl,
W1 and W2 are O;
each of R2 and R3 are independently selected from the group consisting of hydrogen, halogen, cyano, nitro, hydroxy, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, and Ci-Cr, haloalkylthio;
R4is selected from the group consisting of hydrogen, C1-C3 alkyl, and C3-C5 cycloalkyl;
D is,
D4
wherein;
the bond on the right is attached to Z1 and the bond on the left is attached to carbon marked with 2;
R8 is selected from the group consisting of hydrogen, C1-C4 alkyl, C3-C5 cycloalkyl, halogen, cyano, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, and C1-C4 haloalkylthio;
R9 is selected from a phenyl ring, a benzyl ring, a 5- or 6-membered heteroaromatic ring, each ring or ring system optionally substituted with one or more substituent independently selected from the group consisting of halogen, Ci-Ce alkyl, Ci-Ce haloalkyl, cyano, and nitro;
} is a direct bond or CR6R7 or O;
R6 and R7 are independently selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C1-C4 alkyl, and C1-C4 haloalkyl;
E is selected from the group consisting of hydrogen, halogen, cyano, Ci-Ce alkyl, C3-C6 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy or Ci-Ce haloalkoxy, C3- Cr, heterocyclyl; said heterocyclyl ring comprise one or more hetero atoms selected from N, O and S(0)o-2; and one or more C of the heterocyclyl ring or ring system may be replaced with C(=0), C(=S) or C(=NR19); said heterocyclyl ring may be optionally substituted with one or more R16c;
wherein R16a and R16c are independently selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-Ce alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, Ci-Ce alkoxyalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce haloalkylthio, and Ci-Cr, haloalkylsulfinyl;
R19 is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, formyl, Ci-Ce alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, Ci- Cr, alkoxyalkyl, Ci-Ce hydroxyalkyl, CVCr, haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, and Ci-Ce haloalkylthio; or
E is 5- or 6- membered heteroaromatic ring, wherein the heteroatoms in heteroaromatic ring may be selected from one or more N, O and S; and heteroaromatic ring may be optionally substituted with hydrogen, Ci-Ce alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, C3- Cr, halocycloalkyl, halogen, cyano, carboxyl, aminocarboxyl, nitro, hydroxy, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce alkylsulfinyl, Ci-Ce alkylsulphonyl, Ci-Ce haloalkylthio, Ci-Ce haloalkylsulfinyl, and C 1 -Cr, haloal ky Isu I Iony I.
3. The compound according to claim 1, wherein
R4 is hydrogen;
D is,
D4-1
wherein;
the bond on the right is attached to Z1 and the bond on the left is attached to carbon marked with 2;
R8 is hydrogen;
R9 is selected from a 6-membered heteroaromatic ring optionally substituted with one or more halogen;
E is selected from the group consisting of halogen, Ci-Ce haloalkyl, or Ci-Ce alkoxy, C3- Cr, heterocyclyl; said heterocyclyl ring comprise one or more hetero atoms selected from N, O and S(0)o-2; said heterocyclyl ring may be optionally substituted with one or more
Ri6c
wherein R16c is selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-Ce alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkylalkyl, Ci-Ce haloalkyl, Ci-
Cr, alkoxyalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, Ci-Ce haloalkylthio, and C Cr, haloalkylsulfinyl; or
E is 5- membered heteroaromatic ring, wherein the heteroatoms in heteroaromatic ring may be selected from one or more N, O and S; and heteroaromatic ring may be optionally substituted with Ci-Ce alkyl, Ci-Cr, haloalkyl, halogen, cyano, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio, and Ci-Cr, haloalkylthio.
4. The compound according to claim 1, wherein said compound of Formula (I) is selected from 6- (3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N,5-dimethylpyrazolo[l,5- a]pyridine-7 -carboxamide; 6-(3 -bromo- 1 -(3-chloropyridin-2-yl)- 1 H-pyrazole-5 -carboxamido)-N - ethyl-5-methylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH- pyrazole-5-carboxamido)-N-(cyclopropylmethyl)-5-methylpyrazolo[l,5-a]pyridine-7- carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-isopropyl-5- methylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(3-bromo-l -(3-chloropyridin-2-yl)- 1H- pyrazole-5-carboxamido)-N-cyclopropyl-5 -methylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; N- allyl-6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-methylpyrazolo[l,5- a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N- (2-methoxyethyl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3- chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-(tert-butyl)-5-methylpyrazolo[l,5- a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-lH-pyrazole-5- carboxamido)-N,5-dimethylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)- 3-(2,2,2-trifluoroethoxy)-lH-pyrazole-5-carboxamido)-N-ethyl-5-methylpyrazolo[l,5-a]pyridine- 7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-lH-pyrazole-5- carboxamido)-5-methyl-N-propylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin- 2-yl)-3-(2,2,2-trifluoroethoxy)-lH-pyrazole-5-carboxamido)-N-isopropyl-5-methylpyrazolo[l,5- a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-lH-pyrazole-5- carboxamido)-N-cyclopropyl-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3- chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-lH-pyrazole-5-carboxamido)-N- (cyclopropylmethyl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2- yl)-3-(2,2,2-trifluoroethoxy)-lH-pyrazole-5-carboxamido)-N-(cyanomethyl)-5- methylpyrazolo[l,5-a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(2,2,2- trifluoroethoxy)- 1 H-pyrazole-5 -carboxamido)-N -methoxy-5 -methylpyrazolo[ 1 ,5-a]pyridine-7 - carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-lH-pyrazole-5-carboxamido)- N-(2-methoxyethyl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; l-(3-chloropyridin-2-yl)-
N-(7-(3,3-difhioroazetidine-l-carbonyl)-5-methylpyrazolo[l,5-a]pyridin-6-yl)-3-(2,2,2-trifluoroethoxy)-lH-pyrazole-5-carboxamide; N-(tert-butyl)-6-(l-(3-chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-lH-pyrazole-5-carboxamido)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; N-allyl-6-(l -(3-chloropyridin-2-yl)-3-(2, 2, 2-trifluoroethoxy)-lH-pyr azole-5 -carboxamido)-5-methylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-methyl-N-propylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3 -chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-(2-cyanoethyl)-5-methylpyrazolo[l,5-a]pyridine-7 -carboxamide; 3-bromo-l-(3-chloropyridin-2-yl)-N-(7-(3,3-difluoroazetidine-1 -carbonyl)-5-methylpyrazolo[ 1 ,5-a]pyridin-6-yl)- lH-pyrazole-5-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-methoxy-5-methylpyrazolo[ 1 ,5 -a]pyridine-7 -carboxamide; 6-(l -(3-chloropyridin-2-yl)-3 -methoxy- 1H-pyrazole-5-carboxamido)-N,5-dimethylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-cyclopropyl-5-methylpyrazolo[ 1 ,5 -a]pyridine-7 -carboxamide; 6-(l -(3-chloropyridin-2-yl)-3 -methoxy- 1H-pyrazole-5-carboxamido)-N-(cyclopropylmethyl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N- (cyanomethyl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-5-methyl-N-propylpyrazolo[l,5-a]pyridine-7-carboxamide; N-(tert-butyl)-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-ethyl-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-isopropyl-5-methylpyrazolo[ 1 ,5 -a]pyridine-7 -carboxamide; 6-(l -(3-chloropyridin-2-yl)-3 -methoxy- 1H-pyrazole-5-carboxamido)-N-(2-methoxyethyl)-5-methylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; N-(7-(azetidine-l-carbonyl)-5-methylpyrazolo[l,5-a]pyridin-6-yl)-3-bromo-l-(3-chloropyri din-2-yl)-lH-pyr azole-5 -carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-methyl-N-(oxetan-3 -yl)pyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-methyl-N-(prop-2-yn-l-yl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-methyl-N-(2-(methylthio)ethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; N-(7-(azetidine-l-carbonyl)-5-methylpyrazolo[ 1 ,5-a]pyridin-6-yl)- 1-(3 -chloropyridin-2-yl)-3-methoxy- 1H-pyrazole-5-carboxamide; l-(3-chloropyridin-2-yl)-N-(7-(3,3-difluoroazetidine-l-carbonyl)-5-methylpyrazolo[l,5-a]pyridin-6-yl)-3-methoxy-lH-pyrazole-5-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-(cyanomethyl)-5-
methylpyrazolo[ 1 ,5 -a]pyridine-7 -carboxamide; 6-(l -(3-chloropyridin-2-yl)-3 -methoxy- 1H-pyrazole-5-carboxamido)-N-(2-cyanoethyl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-methoxy-5-methylpyrazolo[ 1 ,5 -a]pyridine-7 -carboxamide; 6-(l -(3-chloropyridin-2-yl)-3 -methoxy-lH-pyrazole-5-carboxamido)-5-methyl-N-(2-(methylthio)ethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; N-allyl-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-5-methylpyrazolo[ 1 ,5 -a]pyridine-7 -carboxamide; 6-(l -(3-chloropyridin-2-yl)-3 -methoxy- 1H-pyrazole-5-carboxamido)-5-methyl-N-(prop-2-yn-l-yl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-5-methyl-N-(oxetan-3-yl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-lH-pyrazole-5-carboxamido)-N-(2-cyanoethyl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-lH-pyr azole-5 -carboxamido)-5-methyl-N-(prop-2-yn-l-yl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-lH-pyrazole-5-carboxamido)-5-methyl-N-(2-(methylthio)ethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 5-bromo-6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-propylpyrazolo[l,5-a]pyridine-7-carboxamide; 5-bromo-6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyr azole-5 -carboxamido)-N-methylpyrazolo[ 1,5 -a]pyridine-7-carboxamide; 5-bromo-6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-cyclopropylpyrazolo[l,5-a]pyridine-7-carboxamide; 5-bromo-6-(3-bromo-l-(3-chloropyridin-2-yl)- IH-pyr azole-5 -carboxamido)-N-(tert-butyl)pyrazolo[ 1 ,5 -a]pyridine-7-carboxamide; 5 -bromo-6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N- (cyclopropylmethyl)pyrazolo[ 1 ,5 -a]pyridine-7 -carboxamide; 5 -bromo-6-(3 -bromo- 1-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-(2-(methylthio)ethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; N-allyl-5-bromo-6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)pyrazolo[l,5-a]pyridine-7-carboxamide; 5-bromo-6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-(prop-2-yn-l-yl)pyrazolo[l,5-a]pyridine-7-carboxamide; N-(tert-butyl)-6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-lH-pyrazole-5 -carboxamido)-5-methylpyrazolo[l,5-a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-lH-pyrazole-5-carboxamido)-N-ethyl-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-lH-pyrazole-5-carboxamido)-N-isopropyl-5-methylpyrazolo[l,5-a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-lH-pyrazole-5-carboxamido)-N-cyclopropyl-5-methylpyrazolo[l,5-a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-lH-pyrazole-5-carboxamido)-N-(cyclopropylmethyl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-
yl)-3-(trifluoromethyl)-lH-pyrazole-5-carboxamido)-N,5-dimethylpyrazolo[l,5-a]pyridine-7-carboxamide; N-allyl-6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-lH-pyrazole-5-carboxamido)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-lH-pyrazole-5-carboxamido)-5-methyl-N-(2-(methylthio)ethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; N-butyl-6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-lH-pyrazole-5-carboxamido)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(3,3-difluoroazetidin-l-yl)-lH-pyrazole-5-carboxamido)-N-(cyclopropylmethyl)-5-methylpyrazolo[l,5-a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(3,3-difhioroazetidin-l-yl)-lH-pyrazole-5-carboxamido)-N,5-dimethylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-((l-methyl-3-(trifhioromethyl)-lH-pyrazol-5-yl)oxy)- 1 H-pyrazole-5 -carboxamido)-N,5-dimethylpyrazolo[ 1 ,5 -a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-((l-methyl-3-(trifluoromethyl)-lH-pyrazol-5-yl)oxy)-lH-pyrazole-5-carboxamido)-N-ethyl-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-((l-methyl-3-(trifluoromethyl)-lH-pyrazol-5-yl)oxy)-lH-pyrazole-5-carboxamido)-N-isopropyl-5 -methylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(l -(3-chloropyridin-2-yl)-3- (thietan-3 -yloxy)- 1 H-pyrazole-5-carboxamido)-N-(cyclopropylmethyl)-5 -methylpyrazolo[ 1 ,5 -a]pyridine-7-carboxamide; N-(tert-butyl)-6-(l-(3-chloropyridin-2-yl)-3-(3,3-difluoroazetidin-l-yl)- 1 H-pyrazole-5 -carboxamido)-5 -methylpyrazolo[ 1 ,5 -a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(3,3-difluoroazetidin-l-yl)-lH-pyrazole-5-carboxamido)-N-isopropyl-5-methylpyrazolo[l,5-a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(3,3-difluoroazetidin-l-yl)-lH-pyrazole-5-carboxamido)-N-(diethyl-14-sulfaneybdene)-5-methylpyrazolo[l,5-a]pyridine-7 -carboxamide; 5-bromo-6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-ethylpyrazolo[ 1 ,5 -a]pyridine-7-carboxamide; N-(7-(azetidine- 1 -carbonyl)-5-methylpyrazolo[l,5-a]pyridin-6-yl)-l-(3 -chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-lH-pyrazole-5-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-((l-methyl-3- (trifluoromethyl)-lH-pyrazol-5-yl)oxy)-lH-pyrazole-5-carboxamido)-5-methyl-N-propylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-((l-methyl-3- (trifluoromethyl)-lH-pyrazol-5-yl)oxy)-lH-pyrazole-5-carboxamido)-N-cyclopropyl-5-methylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-((l-methyl-3-(trifluoromethyl)-lH-pyrazol-5-yl)oxy)-lH-pyrazole-5-carboxamido)-N-(cyclopropylmethyl)-5-methylpyrazolo[l,5-a]pyridine-7 -carboxamide; N-(tert-butyl)-6-(l-(3-chloropyridin-2-yl)-3-((l-methyl-3-(trifluoromethyl)-lH-pyrazol-5-yl)oxy)-lH-pyrazole-5-carboxamido)-5-methylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-((l-methyl-3-(trifluoromethyl)-lH-pyrazol-5-yl)oxy)-lH-pyrazole-5-carboxamido)-N-(di ethyl-14-
sulfaneylidene)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(3,3-difluoroazetidin-l-yl)-lH-pyrazole-5-carboxamido)-N-ethyl-5-methylpyrazolo[l,5-a]pyridine-7 -carboxamide; 6-( 1 -(3-chloropyridin-2-yl)-3 -(3 ,3-difluoroazetidin- 1 -yl)- 1 H-pyrazole- 5-carboxamido)-N-methoxy-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(3,3-difluoroazetidin-l-yl)-lH-pyrazole-5-carboxamido)-N-cyclopropyl-5-methylpyrazolo[l,5-a]pyridine-7 -carboxamide; N-allyl-6-(l-(3-chloropyridin-2-yl)-3-(3,3-difluoroazetidin- 1 -yl)- lH-pyrazole-5 -carboxamido)-5 -methylpyrazolo[ 1 ,5 -a]pyridine-7 -carboxamide; 5-bromo-6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-methoxypyrazolo[l,5-a]pyridine-7-carboxamide; 5-bromo-6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-(2-methoxyethyl)pyrazolo[l,5-a]pyridine-7 -carboxamide; N-(7-(azetidine-l-carbonyl)-5-bromopyrazolo[l,5-a]pyridin-6-yl)-3-bromo-l-(3-chloropyridin-2-yl)- 1 H-pyr azole-5 -carboxamide; 3 -bromo-N -(5 -bromo-7 -(3,3 -diflu oroazetidine- 1 -carbonyl)pyrazolo[l,5-a]pyridin-6-yl)-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamide; 5-bromo-6-(3 -bromo- 1 -(3-chloropyridin-2-yl)- lH-pyrazole-5 -carboxamido)-N -isopropylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3- (trifluoromethyl)-lH-pyrazole-5-carboxamido)-5-methyl-N-propylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-lH-pyrazole-5-carboxamido)-N-methoxy-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3- (trifluoromethyl)-lH-pyrazole-5-carboxamido)-N-(diethyl-14-sulfaneylidene)-5-methylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-(l-cyclopropylethyl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-methyl-N-(2, 2, 2-trifluoroethyl)pyrazolo[l,5-a]pyridine-7 -carboxamide; 5-bromo-6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-(2,2,2-trifluoroethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 5-bromo-6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-(l-cyclopropylethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-(l-cyclopropylethyl)-5-methylpyrazolo[l,5-a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-lH-pyrazole-5-carboxamido)-5-methyl-N-(oxetan-3-yl)pyrazolo[l,5-a]pyridine-7-carboxamide;
6-(l-(3-chloropyridin-2-yl)-3-(thietan-3-yloxy)-lH-pyrazole-5-carboxamido)-N,5-dimethylpyrazolo[l,5-a]pyridine-7 -carboxamide; 5-bromo-6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-(cyanomethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(thietan-3-yloxy)-lH-pyrazole-5-carboxamido)-5-methyl-N-propylpyrazolo[ 1 ,5 -a]pyridine-7 -carboxamide; 5 -bromo-6-(l -(3 -chloropyridin-2-yl)-3-
(trifluoromethyl)-lH-pyrazole-5-carboxamido)-N-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-isopropoxy-5-methylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-ethoxy-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 5-bromo-6-(l-(3-chloropyridin-2-yl)-3-(trifhioromethyl)-lH-pyrazole-5-carboxamido)-N-isopropylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(l -(3-chloropyridin-2-yl)-3- (trifluoro methyl)- 1 H-pyrazole-5-carboxamido)-5 -methyl-N-(prop-2-yn- 1 -yl)pyrazolo [1,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(trifhioromethyl)-lH-pyrazole-5-carboxamido)-5-methyl-N-(2,2,2-trifluoroethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-5-methyl-N-(2,2,2-trifluoroethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-ethoxy-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-isopropoxy-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-lH-pyrazole-5-carboxamido)-5-methyl-N-(2,2,2-trifluoroethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-lH-pyrazole-5-carboxamido)-N-ethoxy-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-lH-pyrazole-5-carboxamido)-N-isopropoxy-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-lH-pyrazole-5-carboxamido)-N-(cyanomethyl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-lH-pyrazole-5-carboxamido)-N-(2-methoxyethyl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 5-bromo-N-(tert-butyl)-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)pyrazolo[l,5-a]pyridine-7 -carboxamide; 5 -bromo-6-(l -(3-chloropyridin-2-yl)-3 -methoxy- 1 H-pyrazole-5-carboxamido)-N-propylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(2,2,2-trifluoroethoxy)-lH-pyrazole-5-carboxamido)-N-(l-cyclopropylethyl)-5-methylpyrazolo[l,5-a]pyridine-7 -carboxamide; 5-bromo-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-cyclopropylpyrazolo[l,5-a]pyridine-7-carboxamide; 5-bromo-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N- (cyclopropylmethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 5-bromo-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-methoxypyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-lH-pyrazole-5-carboxamido)-N-isopropoxy-5-methylpyrazolo[l,5-a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)- lH-pyrazole-5-carboxamido)-N-(l -cyclopropylethyl)-5 -methylpyrazolo[ 1 ,5 -a]pyridine-7 -carboxamide; 5-bromo-6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-lH-pyrazole-5-carboxamido)-N-ethylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-lH-pyrazole-5-carboxamido)-5-methyl-N-(3-oxoisoxazolidin-4-yl)pyrazolo[ 1 ,5 -a]pyridine-7 -carboxamide; 5 -bromo-6-(l -(3-chloropyridin-2-yl)-3 - (triflu oro methyl)- 1 H-pyrazole-5-carboxamido)-N-(3 -oxoisoxazolidin-4-yl)pyrazolo [1,5-a]pyridine-7 -carboxamide; 5 -bromo-6-(l -(3-chloropyridin-2-yl)-3 -methoxy- 1 H-pyrazole-5-carboxamido)-N-isopropylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 5-chloro-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N- (cyclopropylmethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 5-chloro-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-cyclopropylpyrazolo[l,5-a]pyridine-7-carboxamide; 5-chloro-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-isopropylpyrazolo[l,5-a]pyridine-7 -carboxamide; 5-chloro-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-ethylpyrazolo[l,5-a]pyridine-7-carboxamide;
5-chloro-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-methylpyrazolo[l,5-a]pyridine-7 -carboxamide; N-(tert-butyl)-5-chloro-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)pyrazolo[l,5-a]pyridine-7-carboxamide; 5-chloro-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-(2,2,2-trifluoroethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-chloro-N-isopropylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3 -chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-butyl-5-chloropyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-chloro-N-(cyclopropylmethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-chloro-N-(prop-2-yn-l-yl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-chloro-N-ethylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-chloro-N-(2,2,2-trifluoroethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(thietan-3-yloxy)-lH-pyrazole-5-carboxamido)-N-ethyl-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(thietan-3-yloxy)-lH-pyrazole-5-carboxamido)-N-cyclopropyl-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(thietan-3-yloxy)-lH-pyrazole-5-carboxamido)-N-(l-cyclopropylethyl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(thietan-3-yloxy)-lH-pyrazole-5-carboxamido)-N-methoxy-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-chloro-N-
methylpyrazolo[l,5-a]pyridine-7 -carboxamide; 5-chloro-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-(cyanomethyl)pyrazolo[l,5-a]pyridine-7-carboxamide;
5-chloro-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-methoxypyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-chloro-N-propylpyrazolo[l,5-a]pyridine-7-carboxamide; rac-(R)-6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-methyl-N-(3-oxoisoxazolidin- 4-yl)pyrazolo [ 1 ,5 -a]pyridine-7 -carboxamide; 5 -chloro-6-(l -(3 -chloropyridin-2-yl)-3-((5- (trifluoromethyl)-2H-tetrazol-2-yl)methyl)-lH-pyrazole-5-carboxamido)-N-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 5-chloro-6-(l-(3-chloropyridin-2-yl)-3-((5-(trifluoromethyl)-2H-tetrazol-2-yl)methyl)-lH-pyrazole-5-carboxamido)-N-ethylpyrazolo[l,5-a]pyridine-7-carboxamide; 5-chloro-6-(l-(3-chloropyridin-2-yl)-3-((5-(trifbioromethyl)-2H-tetrazol-2-yl)methyl)- lH-pyrazole-5-carboxamido)-N-propylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(3-bromo- 1-(3 -chloropyridin-2-yl)- lH-pyrazole-5-carboxamido)-N-(tert-butyl)pyrazolo[ 1 ,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-ethylpyrazolo[l, 5 -a]pyridine-7 -carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole- 5-carboxamido)-N-propylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-cyclopropylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N- (cyclopropylmethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(thietan-3-yloxy)-lH-pyrazole-5-carboxamido)-N-(2-methoxyethyl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 5-chloro-6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-lH-pyrazole-5-carboxamido)-N-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)- 1 H-pyr azole-5 -carboxamido)-N-methoxypyrazolo[ 1 ,5 -a]pyridine-7 -carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-isopropylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyr azole-5 -carboxamido)-N -(2,2 ,2-trifluoroethyl)pyrazolo [1,5 -a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-((5-(trifluoromethyl)-2H-tetrazol-2-yl)methyl)-lH-pyr azole-5-carboxamido)-N,5-dimethylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-((5-(trifluoromethyl)-2H-tetrazol-2-yl)methyl)-lH-pyrazole-5-carboxamido)-N-ethyl-5-methylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-((5- (trifluoromethyl)-2H-tetrazol-2-yl)methyl)-lH-pyrazole-5-carboxamido)-N-cyclopropyl-5-methylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-((5- (trifluoromethyl)-2H-tetrazol-2-yl)methyl)-lH-pyrazole-5-carboxamido)-N-(l-cyclopropylethyl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; N-(tert-butyl)-6-(l-(3-chloropyridin-2-yl)-3-
((5-(trifluoromethyl)-2H-tetrazol-2-yl)methyl)-lH-pyrazole-5-carboxamido)-5-methylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(l -(3-chloropyridin-2-yl)-3-((5- (trifluoromethyl)-2H-tetrazol-2-yl)methyl)-lH-pyrazole-5-carboxamido)-N-(cyclopropylmethyl)- 5-methylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(3-bromo-l -(3-chloropyridin-2-yl)- 1H-pyrazole-5-carboxamido)-5 -methyl -N-(l -methylcyclopropyl)pyrazolo [ 1 ,5 -a]pyridine-7 -carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-methyl-N-(3-methyloxetan-3-yl)pyrazolo[l,5-a]pyridine-7 -carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-(l-methoxy-2-methylpropan-2-yl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-methyl-N-neopentylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)- 1 H-pyr azole-5 -carboxamido)-5 -methyl-N - (pentan-2-yl)pyr azolo [1,5 -a]pyridine-7 -carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-(3,3-dimethylbutan-2-yl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)- 1 H-pyr azole-5 -carboxamido)-N-(3 ,3 -dimethylbutyl)-5 -methylpyrazolo[ 1 ,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-methylpyrazolo[l,5-a]pyridine-7 -carboxamide; N-(adamantan-l-yl)-6-(3-bromo-l-(3-chloropyridin-2-yl)- 1 H-pyr azole-5 -carboxamido)-5-methylpyrazolo[ 1 ,5 -a]pyridine-7-carboxamide; N-(adamantan-l-yl)-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy- lH-pyrazole-5-carboxamido)-5-methyl-N-neopentylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-(3,3-dimethylbutan-2-yl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-5-methyl-N-(pentan-2-yl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-methyl-N-(pentan-3-yl)pyrazolo[l,5-a]pyridine-7 -carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-(2,2-difluoroethyl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide;
6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-methyl-N-(l,l,l-trifhioropropan-2-yl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)- 1 H-pyr azole-5 -carboxamido)-5 -methyl-N - (5 -methylhexan-2-y l)pyrazolo [ 1 ,5 -a]pyridine-7 -carboxamide; rac-(R)-6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-methyl-N-((tetrahydrofuran-2-yl)methyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-methyl-N-((tetrahydro-2H-pyran-2-yl)methyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5 -methyl -N-(3 -methylbutan-2-yl)pyrazolo [ 1 ,5 -a]pyridine-7 -
carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-(l-methoxybutan-2-yl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-methyl-N-(thiazol-2-ylmethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-(cyclopentylmethyl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-methyl-N-((tetrahydro-2H-pyran-4-yl)methyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-(l-hydroxy-2-methylpropan-2-yl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-(l-hydroxy-2-methylpropan-2-yl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-5-methyl-N-(pentan-3-yl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-5-methyl-N-(2-methylbutyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-5-methyl-N-(2-(4-methylthiazol-5-yl)ethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-5-methyl-N-((tetrahydro-2H-pyran-4-yl)methyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-5-methyl-N-((tetrahydrofuran-2-yl)methyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-(cyclopentylmethyl)-5-methylpyrazolo[ 1 ,5 -a]pyridine-7 -carboxamide; 6-(l -(3-chloropyridin-2-yl)-3 -methoxy- 1H-pyrazole-5-carboxamido)-5-methyl-N-(thiazol-2-ylmethyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-(l-methoxybutan-2-yl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-isopentyl-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-methyl-N-(thietan-3-yl)pyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-N-(l,l-dioxidothietan-3-yl)-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamido)-5-methyl-N-(l-oxidothietan-3-yl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-5-methyl-N-(5-methylhexan-2-yl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-isopentyl-5-methylpyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-5-methyl-N-(3-methylbutan-2-yl)pyrazolo[l,5-a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-5-methyl- N-((tetrahydro-2H-pyran-2-yl)methyl)pyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(l-(3- chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-(2,2-difluoroethyl)-5- methylpyrazolo[ 1 ,5 -a]pyridine-7 -carboxamide; 6-(l -(3-chloropyridin-2-yl)-3 -methoxy-lH- pyrazole-5-carboxamido)-5-methyl-N-(thietan-3-yl)pyrazolo[l,5-a]pyridine-7 -carboxamide; 6-(3- bromo- 1 -(3 -chloropyridin-2-yl)- lH-pyrazole-5 -carboxamido)-N-( 1 -cyanocyclopropyl)-5 - methylpyrazolo[ 1 ,5 -a]pyridine-7 -carboxamide; 6-(l -(3-chloropyridin-2-yl)-3 -methoxy- 1H- pyrazole-5-carboxamido)-5-methyl-N-(l , 1 , 1 -trifluoropropan-2-yl)pyrazolo[ 1 ,5-a]pyridine-7 - carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-(3,3- dimethylbutyl)-5-methylpyrazolo[ 1 ,5-a]pyridine-7 -carboxamide; 6-(l-(3-chloropyridin-2-yl)-3- methoxy-lFFpyrazole-5-carboxamido)-5-methyl-N-(l-methylcyclopropyl)pyrazolo[l,5- a]pyridine-7-carboxamide; 6-(l-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-lH-pyrazole-5- carboxamido)-5-methyl-N-(l , 1 , 1 -trifluoropropan-2-yl)pyrazolo[ 1 ,5-a]pyridine-7-carboxamide; 6- (l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-(l-cyanocyclopropyl)-5- methylpyrazolo[l,5-a]pyridine-7 -carboxamide; 5-bromo-6-(l-(3-chloropyridin-2-yl)-3-methoxy- lH-pyrazole-5-carboxamido)-N-(2,2,2-trifluoroethyl)pyrazolo [ 1 ,5 -a]pyridine-7 -carboxamide; 5 - bromo-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N-(l- methylcyclopropyl)pyrazolo[l,5-a]pyridine-7-carboxamide; 5-bromo-6-(l-(3-chloropyridin-2-yl)- 3-methoxy-lH-pyrazole-5-carboxamido)-N-(l-cyclopropylethyl)pyrazolo[l,5-a]pyridine-7- carboxamide; 5-bromo-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)-N- (thietan-3-yl)pyrazolo[l,5-a]pyridine-7-carboxamide; 5-bromo-6-(l-(3-chloropyridin-2-yl)-3- methoxy- lH-pyrazole-5-carboxamido)-N-( 1,1,1 -trifluoropropan-2-yl)pyrazolo[ 1 ,5-a]pyridine-7 - carboxamide and 5-bromo-6-(l-(3-chloropyridin-2-yl)-3-methoxy-lH-pyrazole-5-carboxamido)- N-(oxetan-3-yl)pyrazolo[l,5-a]pyridine-7-carboxamide.
5. The compound of Formula (I) or salts, metal complexes, N-oxides, isomers, or polymorphs thereof according to claim 1, in a biologically effective amount in a composition comprising at least one additional component selected from the group consisting of surfactants and auxiliaries for controlling or preventing insects and/or mite pests.
6. The compound of Formula (I) or salts, metal complexes, N-oxides, isomers, or polymorphs thereof according to claim 1, in a composition comprising at least one additional component selected from the group consisting of surfactants and auxiliaries for agricultural and/or veterinary applications.
7. The composition according to claim 5, 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.
8. 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.
9. The composition or combination according to claim 5 or 8, 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 method of combating insects and mite pests comprising contacting the insects and mite pests, their habit, 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 5 or 8.
11. 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 5 or 8.
12. The method according to claim 11, 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.
13. A method for the protection of seeds from soil insects and of the seedlings roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pre-germination with the compound of Formula (I) or salts, metal complexes, N-oxides, isomers, polymorphs, composition or combination thereof according to claim 1 or 5 or 8.
14. The compound of Formula (I) or salts, metal complexes, N-oxides, isomers, polymorphs, or combination thereof according to claim 1 or 5 or 8 in a biologically effective amount in the composition for treating or protecting animals against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the animals of.
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 5 or 8, for combating insects and mite pests in agricultural crops and/or horticultural crops or parasites.
16. The use of the compound of Formula (I) according to claim 15, in the preparation of a medicament for treating or protecting animals against infestation or infection by insect and mite pests or parasites.
17. The use of the compound of Formula (I) according to claim 15, wherein said agricultural crops are 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, other vegetables and ornamentals.
18. 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 5 or 8, wherein the amount of compound of Formula (I) in said seed ranging from about 0.0001% to about 1% by weight.
19. A process for preparing compound of Formula (I) according to claim 1, said process comprising the steps of:
a) reacting a ketone II with an alkoxy amino III to obtain an amino ketone IV;
b) reacting the amino ketone IV with an aminoglycinate salt V to obtain pyrazol acetate VI; c) reacting the pyrazol acetate VI with a wittig reagent VII to obtain cyano ester VIII;
d) cyclizing the cyano ester VIII to obtain a compound of Formula la, wherein R15= OCi-Ce alkyl, followed by hydrolyzing to obtain a compound of Formula la, wherein R15= OH;
e) reacting the compound of Formula la, wherein R15 = OH with a pyrazole carboxylic acid IX to obtain a compound of Formula Ic; and
f) reacting the compound of Formula Ic with an amine X to obtain the compound of Formula
(I),
R - NR10R
20. A compounds of Formulae la, lb, Ic and Id;
wherein, R15 is OR17, SR17, halogen or R1; R16 is N(R4)2 or nitro; R17 is hydrogen, Ci-Cs alkyl; W1, A1, A2, A3, B1, B2, D, Z1, E, R1, R2, R3, R4, m and n are as defined in claim 1.
| # | Name | Date |
|---|---|---|
| 1 | 202017028324-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [03-07-2020(online)].pdf | 2020-07-03 |
| 2 | 202017028324-STATEMENT OF UNDERTAKING (FORM 3) [03-07-2020(online)].pdf | 2020-07-03 |
| 3 | 202017028324-PRIORITY DOCUMENTS [03-07-2020(online)].pdf | 2020-07-03 |
| 4 | 202017028324-FORM 1 [03-07-2020(online)].pdf | 2020-07-03 |
| 5 | 202017028324-DECLARATION OF INVENTORSHIP (FORM 5) [03-07-2020(online)].pdf | 2020-07-03 |
| 6 | 202017028324-COMPLETE SPECIFICATION [03-07-2020(online)].pdf | 2020-07-03 |
| 7 | 202017028324-FORM 3 [28-09-2020(online)].pdf | 2020-09-28 |
| 8 | 202017028324-FORM 18 [30-09-2021(online)].pdf | 2021-09-30 |
| 9 | 202017028324.pdf | 2021-10-19 |
| 10 | 202017028324-FER.pdf | 2021-11-03 |
| 11 | 202017028324-FORM 3 [12-11-2021(online)].pdf | 2021-11-12 |
| 12 | 202017028324-FORM-26 [23-02-2022(online)].pdf | 2022-02-23 |
| 13 | 202017028324-Proof of Right [03-05-2022(online)].pdf | 2022-05-03 |
| 14 | 202017028324-OTHERS [03-05-2022(online)].pdf | 2022-05-03 |
| 15 | 202017028324-Information under section 8(2) [03-05-2022(online)].pdf | 2022-05-03 |
| 16 | 202017028324-FORM 3 [03-05-2022(online)].pdf | 2022-05-03 |
| 17 | 202017028324-FER_SER_REPLY [03-05-2022(online)].pdf | 2022-05-03 |
| 18 | 202017028324-CLAIMS [03-05-2022(online)].pdf | 2022-05-03 |
| 19 | 202017028324-FORM 3 [22-12-2022(online)].pdf | 2022-12-22 |
| 20 | 202017028324-US(14)-HearingNotice-(HearingDate-03-02-2023).pdf | 2023-01-12 |
| 21 | 202017028324-Correspondence to notify the Controller [31-01-2023(online)].pdf | 2023-01-31 |
| 22 | 202017028324-Written submissions and relevant documents [17-02-2023(online)].pdf | 2023-02-17 |
| 23 | 202017028324-PatentCertificate15-03-2024.pdf | 2024-03-15 |
| 24 | 202017028324-IntimationOfGrant15-03-2024.pdf | 2024-03-15 |
| 1 | SearchHistoryE_03-11-2021.pdf |