Heterocyclic fused compounds and their use as pest control agents.

Abstract

The present invention discloses a fused heterocyclic compound of formula (i), formula (i) wherein r1, y, q, a, g, mee are as defined in the detailed description. The present invention further discloses methods for the preparation and use of the compounds of formula (i) as a pest control agent.

Description

[0001] The present invention relates to fused heterocyclic compounds. More particularly, the present invention relates to fused heterocyclic compounds of formula (I) and to the process for preparing them. The present invention further relates to the use of fused heterocyclic compounds of formula (I) as pest control agents. BACKGROUND OF THE INVENTION:

[0002] Modern insecticides and acaricides currently available have to meet many requirements, for example, regarding the level of effectiveness, residual activity and spectrum of activity, as well as additional beneficial effects and their possible uses. There have been efforts during the last decades to develop selective insecticides that act specifically on biochemical modes of action present only in insects or mites, but additionally showing properties that are different from known insecticides in an advantageous way.

[0003] Heterocyclic compounds with pesticidal activity are known and described, for example, in documents WO2016091731, WO2016162318, WO2017061497, WO2017125340, WO2017001311, WO2018095953, WO2019068572 and WO2019038195.

[0004] However, with the long-term use of such pesticides, many pests develop resistance, and effective control by existing insecticides and germicides becomes impossible. Petition 870220032852, dated 04 / 18 / 2022, page 9 / 320 2 / 312 have been used conventionally for years, but this is becoming increasingly difficult, and this phenomenon has been occurring more frequently in recent years. Furthermore, some of these existing pesticides are highly toxic or remain in the environment for a long time due to their residual properties, which can become a growing problem due to ecosystem disruption.

[0005] Therefore, there is a continuing need for innovative compounds that are more effective, less toxic and environmentally safer and / or have different modes of action.

[0006] In view of the foregoing, the present invention provides such compounds that satisfy or overcome disadvantages associated with the prior art.

[0007] It has been surprisingly found that certain fused heterocyclic compounds active as innovative pesticides with sulfur-containing substituents that are the subject matter of this invention have favorable properties as pesticides, as desired. SUMMARY OF THE INVENTION:

[0008] Correspondingly, the present invention provides a fused heterocyclic compound of formula (I) or salts, isomers / structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, metal complexes, acceptable polymorphs or N-oxides thereof. Formula (I) Petition 870220032852, dated 04 / 18 / 2022, page 10 / 320 3 / 312 where R1, Y, Q, A, G, m and E are as defined in the detailed description.

[0009] In one embodiment, the present invention provides a process for preparing the compound of formula (I) or agriculturally acceptable salts thereof.

[0010] In another embodiment, the present invention provides a composition for controlling or preventing invertebrate pests comprising a biologically effective amount of the compound of formula (I), agriculturally acceptable salts, structural isomers / isomers, stereoisomers, diastereoisomers, enantiomers, tautomers, metal complexes, acceptable polymorphs or N-oxides thereof and at least one additional component selected from the group consisting of surfactants and auxiliaries.

[0011] In another embodiment, the composition further comprises at least one additional biologically active and compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers or nutrients.

[0012] In yet another embodiment, the present invention provides use of the compound of formula (I), agriculturally acceptable salts, structural isomers / isomers, stereoisomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs or N-oxides, composition or combination thereof, to combat invertebrate pests in agricultural and / or horticultural crops or parasites in animals.

[0013] In another embodiment, the present invention provides a method of controlling invertebrate pests comprising coming into contact with the invertebrate pests, Petition 870220032852, dated 04 / 18 / 2022, page 11 / 320 4 / 312 their habitat, breeding ground, food supply, plant, seed, soil, area, material or environment in which invertebrate pests grow or may grow, or with the materials, plants, seeds, soils, surfaces or spaces to be protected against attack or infestation by pests with a biologically effective amount of the compound of formula (I) or agriculturally acceptable salts, structural isomers / isomers, stereoisomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs or N-oxides, composition or combination thereof. DETAILED DESCRIPTION OF THE INVENTION: DEFINITIONS:

[0014] The definitions provided herein for the terminology used in this disclosure are for illustrative purposes only and in no way limit the scope of the present invention disclosed in this disclosure.

[0015] As used in this document, the terms comprise, comprising, includes, which includes, has, which has, contains, which contains, characterized by, or any other variation thereof encompass a non-exclusive inclusion, subject to any limitation explicitly stated. For example, a composition, mixture, process, or method comprising a list of elements is not necessarily limited to only those elements, but may include other elements not expressly listed or inherent in such composition, mixture, process, or method.

[0016] The transitional phrase that consists of excludes any unspecified element, step, or ingredient. If Petition 870220032852, dated 04 / 18 / 2022, page 12 / 320 5 / 312 in the claim, such a phrase would limit the claim to the inclusion of materials other than those mentioned, except for impurities commonly associated with them. When the phrase consisting of appears in the body sentence of the claim, and not immediately after the preamble, this limits only the element presented in the sentence; other elements are not excluded from the claim as a whole.

[0017] 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 such additional materials, steps, features, components, or elements do not materially affect the basic and innovative feature(s) of the invention claimed. The term consisting essentially of serves as an intermediate term between comprising and consisting of.

[0018] Furthermore, unless expressly stated otherwise, either refers to an inclusive or not to an exclusive or. For example, a condition A or B is satisfied by any 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).

[0019] Furthermore, the indefinite articles "a" and "an," before an element or component of the present invention, are not restrictive with respect to the number of appearances (i.e., occurrences) of the element or component. Therefore, "a" or "an" should be read as including "a" or "at least one," and the singular form of the element or component also includes the plural, unless the number is clearly singular. Petition 870220032852, dated 04 / 18 / 2022, p. 13 / 320 6 / 312

[0020] As stated 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, woodlice, 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), trematodes (Tematoda), acanthocephalans, and tapeworms (Cestoda).

[0021] The agronomic term refers to the production of crops in the field as for food and fiber and includes the growing of corn, soybeans and other legumes, rice, cereals (e.g., wheat, oats, barley, rye, rice, maize), leafy vegetables (e.g., lettuce, cabbage and other cole crops), fruiting vegetables (e.g., tomatoes, peppers, eggplant, cruciferous vegetables and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., orchard, drupe and citrus), small fruit (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives).

[0022] The term “non-agronomic” refers to other crops in the field, such as horticulture (e.g., greenhouse, nurseries, or ornamental plants not grown in a field), residential, agricultural, commercial, and industrial structures, turf (e.g., turf farms, pasture, golf course, lawn, sports field, etc.), applications in wood products, stored product, agroforestry and vegetation management, public health (i.e., of Petition 870220032852, dated 04 / 18 / 2022, page 14 / 320 7 / 312 human beings) and animal health (e.g., domesticated animals such as pets, livestock and poultry, non-domesticated animals such as wild animals).

[0023] Non-agronomic applications include protecting an animal from an invertebrate parasitic pest by administering a parasiticidally effective (i.e., biologically effective) amount of a compound of the present invention, typically in the form of a composition formulated for veterinary use, to the animal to be protected. As referred to in the present disclosure and claims, the terms parasiticidal and parasiticidally refer to observable effects on an invertebrate parasitic pest to provide protection of an animal against the pest. Parasiticidal effects are typically related to decreasing the occurrence or activity of the target invertebrate parasitic pest. Such effects on the pest include necrosis, death, retarded growth, decreased mobility or impaired 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.

[0024] 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 are within the Petition 870220032852, dated 04 / 18 / 2022, page 15 / 320 8 / 312 scope of the claims of the present disclosure. A person skilled in the art will appreciate that a stereoisomer may be more active and / or may exhibit beneficial effects when enriched relative to another isomer (or isomers) or when separated from the other isomer (or isomers). Furthermore, a person skilled in the art knows processes or methods or technology for selectively separating, enriching and / or preparing said isomers.

[0025] The meaning of several terms used in the description will now be illustrated.

[0026] The term aliphatic compound(s) or aliphatic group(s) used in this document refers to an organic compound(s) whose carbon atoms are linked in straight chains, branched chains, or non-aromatic rings.

[0027] The term alkyl, used separately or in compound words, such as alkylthio or haloalkyl or -N(alkyl) or alkylcarbonylalkyl or alkylsulfonylamino includes C1 to C24 linear or branched chain alkyl, preferably C1 to C15 alkyl, more preferably C1 to C10 alkyl, most preferably C1 to C6 alkyl. Representative examples of alkyl groups include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl. Petition 870220032852, dated 04 / 18 / 2022, page 16 / 320 9 / 312 1-ethyl-1-methylpropyl and l-ethyl-2-methylpropyl or different isomers. If the alkyl group is at the end of a compound substituent, such as in alkylcycloalkyl, the beginning part of the compound substituent, for example, cycloalkyl, may be identically or differently and independently mono- or polysubstituted by alkyl. The same also applies to compound substituents in which other radicals, for example, alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy and the like, are at the end.

[0028] The term alkenyl, used separately or in compound words, includes C2 to C24 branched or linear chain alkenes, preferably C2 to C15 alkenes, more preferably C2 to C10 alkenes, with maximum preference, C2 to C6 alkenes.Representative examples of alkenes include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-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, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl. 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3. Petition 870220032852, dated 04 / 18 / 2022, page 17 / 320 10 / 312 pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-l-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3dimethyl-l-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl and the different isomers. Alkenyl also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl as part of a composite substituent, for example, haloalkenyl and the like, except where specifically defined throughout this document.

[0029] The term alkynyl, used separately or in compound words, includes C2 to C24 linear or branched chain alkynes, preferably C2 to C15 alkynes, more preferably C2 to C10 alkynes, with maximum preference, C2 to C6 alkynes. Non-limiting examples of alkynes include ethinyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentinyl, 1-methyl-3-pentinyl, 1-methyl-4-pentinyl, 2Petition 870220032852, of 18 / 04 / 2022, page 18 / 320 11 / 312 methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl and the different isomers. This definition also applies to alkynyl as part of a composite substituent, for example, haloalkynyl etc., unless otherwise defined. The term alkynyl can also include fractions comprising multiple triple bonds, such as 2,5-hexadiynyl.

[0030] The term cycloalkyl means alkyl closed to form a ring. Non-limiting examples include, but are not limited to, cyclopropyl, cyclopentyl, and cyclohexyl. This definition also applies to cycloalkyl as part of a composite substituent, for example, cycloalkylalkyl etc., unless specifically defined otherwise.

[0031] The term cycloalkenyl means alkenyl closed to form a ring that includes partially unsaturated monocyclic hydrocarbyl groups. Non-limiting examples include, but are not limited to, cyclopropenyl, cyclopentyl, and cyclohexenyl. This definition also applies to cycloalkenyl as part of a composite substituent, for example, cycloalkenylalkyl, etc., unless specifically defined otherwise.

[0032] The term cycloalkynyl means alkynyl group closed to form a ring that includes partially unsaturated monocyclic groups. Non-limiting examples Petition 870220032852, dated 04 / 18 / 2022, p. 19 / 320 12 / 312 includes, but is not limited to, cyclopopinyl, cyclopentinyl, and cyclohexinyl. This definition also applies to cycloalkynyl as part of a composite substituent, for example, cycloalkynylalkyl, etc., unless specifically defined otherwise.

[0033] The terms 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 part of a substituent in a compound, for example, cycloalkoxyalkyl etc., unless specifically defined otherwise.

[0034] The term halogen, whether used separately or in compound words such as haloalkyl, includes fluorine, chlorine, bromine, or iodine. Furthermore, when used in compound words such as haloalkyl, the said alkyl may be wholly or partially replaced by halogen atoms which may be the same or different. Non-limiting examples of haloalkyl include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl and 1,1,1-trifluoropropyl-2-yl. This definition also applies to haloalkyl as part of a composite substituent, for example, haloalkylaminoalkyl etc., unless specifically Petition 870220032852, dated 04 / 18 / 2022, p. 20 / 320 13 / 312 defined the opposite.

[0035] The terms haloalkenyl, haloalkynyl are defined analogously, except that, instead of alkyl groups, alkenyl and alkynyl groups are present as part of the substituent.

[0036] The term haloalkoxy means linear or branched chain alkoxy groups in which some or all of the hydrogen atoms in these groups may be replaced by halogen atoms, as specified above. Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1-trifluoroprop-2-oxy. This definition also applies to haloalkoxy, as part of a composite substituent, for example, haloalkoxyalkyl, etc., unless specifically defined otherwise.

[0037] The term haloalkylthio means linear or branched chain alkylthio groups in which 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, 1Petition 870220032852, dated 18 / 04 / 2022, page 21 / 320 14 / 312 fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethylthio and 1,1,1-trifluoroprop2-ylthio. This definition also applies to haloalkylthio as part of a composite substituent, for example, haloalkylthioalkyl etc., unless specifically defined otherwise.

[0038] Non-limiting examples of haloalkylsulfonyl include CF3S(O), CCl3S(O), CF3CH2S(O), and CF3CF2S(O). Examples of haloalkylsulfonyl include CF3S(O)2, CCl3S(O)2, CF3CH2S(O)2 and CF3CF2S(O)2.

[0039] The term hydroxy means —OH, amino means -NRR, where R can be H or any possible substituent, such as alkyl. Carbonyl means -C(O)-, carbonyloxy means -OC(O)-, sulfinyl means SO, sulfonyl means S(O)2.

[0040] The term alkoxy, used separately or in compound words, includes C1 to C24 alkoxy, preferably C1 to C15 alkoxy, more preferably C1 to C10 alkoxy, with maximum preference C1 to C6 alkoxy.Examples of alkoxy compounds 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 their isomers. Petition 870220032852, dated 04 / 18 / 2022, page 22 / 320 15 / 312 different. This definition also applies to alkoxy, as part of a composite substituent, for example, haloalkoxy, alkynylalkoxy, etc., unless specifically defined otherwise.

[0041] The term Alkoxyalkyl denotes the substitution of alkoxy into alkyl. Non-limiting examples of alkoxyalkyl include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2

[0042] The term alkoxyalkoxy denotes the substitution of alkoxy for alkoxy.

[0043] The term alkylthio includes linear or branched chain alkylthio fractions, 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.

[0044] Halocycloalkyl, halocycloalkenyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylcarbonyl, cycloalkylcarbonyl, haloalkoxylalkyl and the like are defined analogously to the examples above. Petition 870220032852, dated 04 / 18 / 2022, page 23 / 320 16 / 312

[0045] The term alkylthioalkyl denotes the substitution of alkylthio on alkyl. Representative examples of alkylthioalkyl include -CH2SCH2, -CH2SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2, and CH3CH2SCH2CH2. Alkylthioalkoxy denotes the substitution of alkylthio on alkoxy. The term cycloalkylalkylamino denotes the substitution of cycloalkyl on alkylamino.

[0046] The terms alkoxyalkyloxyalkyl, alkylaminoalkyl, dialkylaminoalkyl, cycloalkylaminoalkyl, cycloalkylaminocarbonyl and the like are defined in a manner analogous to alkylthioalkyl or cycloalkylalkylamino.

[0047] The term alkoxycarbonyl is an alkoxy group attached to a skeleton via a carbonyl group (-CO-). This definition also applies to alkoxycarbonyl as part of a composite substituent, for example, cycloalkylalkoxycarbonyl and the like, unless specifically defined otherwise.

[0048] The term alkoxycarbonylalkylamino denotes the substitution of an alkoxy carbonyl group with an alkyl amino group. Alkylcarbonylalkylamino denotes the substitution of an alkyl carbonyl group with an alkyl amino group. The terms alkylthioalkoxycarbonyl, cycloalkylalkylaminoalkyl and the like are defined analogously.

[0049] Non-limiting examples of alkylsulfinyl include, but are not limited to, methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3Petition 870220032852, dated 18 / 04 / 2022, page 24 / 320 17 / 312 methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1ethylpropylsulfinyl, hexylsulfinyl, 1,1dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 1methylpentylsulfinyl, 2-methylpentylsulfinyl, 3methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl and its different isomers. The term arylsulfinyl includes ArS(O), where Ar can be any carbocycle or heterocycle. This definition also applies to alkylsulfinyl, as part of a composite substituent, for example, haloalkylsulfinyl, etc., unless specifically defined otherwise.

[0050] Non-limiting examples of alkylsulfonyl include, but are not limited to, methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3 Petition 870220032852, dated 04 / 18 / 2022, page 25 / 320 18 / 312 dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl and the different isomers. The term arylsulfonyl includes ArS(O)2, where Ar can be any carbocycle or heterocycle. This definition also applies to alkylsulfonyl, as part of a composite substituent, for example, alkylsulfonylalkyl etc., unless defined elsewhere.

[0051] Alkylamino, dialkylamino and the like are defined in a manner analogous to the examples above.

[0052] The term carbocyclic includes aromatic carbocyclic ring systems and non-aromatic carbocyclic ring systems or polycyclic or bicyclic (spiro, fused, bridging, non-fused) ring compounds in which the ring may be aromatic or non-aromatic (where aromatic indicates that Huckel's rule is satisfied, and non-aromatic indicates that Huckel's rule is not satisfied).

[0053] The term hetero in combination with rings refers to a ring in which at least one ring atom is not carbon and which may contain 1 to 4 heteroatoms selected independently from the group consisting of nitrogen, oxygen and sulfur, given that each ring contains at most 4 nitrogens, at most 2 oxygens and at most 2 sulfurs.

[0054] The term aromatic indicates that Huckel's rule is satisfied, and the term non-aromatic indicates that Huckel's rule is not satisfied.

[0055] The term heterocycle or heterocyclic or Petition 870220032852, dated 04 / 18 / 2022, p. 26 / 320 19 / 312 heterocyclic ring system includes aromatic heterocycle or heteroaryl bicyclic ring system and non-aromatic heterocyclic ring system or polycyclic or bicyclic ring compounds (spiro, fused, bridging, non-fused) wherein the ring may be aromatic or non-aromatic, wherein the heterocycle ring contains at least one heteroatom selected from N, O, S(O) O-2, and / or the C ring member of the heterocycle may be replaced by C(=O), C(=S), C(=CR*R*) and C=NR*, * indicates integers.

[0056] The term non-aromatic heterocycle or non-aromatic heterocyclic means a saturated or partially unsaturated heterocycle of three to fifteen members, preferably three to twelve members, containing one to four heteroatoms of the oxygen, nitrogen and sulfur groups: mono-, bi- or tricyclic heterocycles containing, in addition to carbon ring members,one to three nitrogen atoms and / or one oxygen or sulfur atom, or one or two oxygen and / or sulfur atoms; if the ring contains more than one oxygen atom, these are not directly adjacent; for example (but without limitation) oxetanyl, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5thiazolidinyl, 1-imidazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-Petition 870220032852, dated 04 / 18 / 2022, page 27 / 320, 20 / 312 oxadiazolidin-5-ila, 1,2,4-tiadiazolidin-3-ila, 1,2,4tiadiazolidin-5-ila, 1,2,4-triazolidin-1-ila, 1,2,4triazolidin-3-ila, 1,3,4-oxadiazolidin-2-ila, l,3,4tiadiazolidin-2-ila, 1,3,4-triazolidin-1-ila, 1,3,4 triazolidin-2-ila, 2,3-di-hidrofur-2-ila, 2,3-di-hidrofur 3-ila, 2,4-di-hidrofur-2-ila, 2,4-di-hidrofur-3-ila, 2,3di-hidrotien-2-ila, 2,3-di-hidrotien-3-ila, 2,4-di-hidrotien-2-ila, 2,4-di-hidrotien-3-ila, pirrolinila, 2pirrolin-2-ila, 2-pirrolin-3-ila, 3-pirrolin-2-ila, 3pirrolin-3-ila, 2-isoxazolin-3-ila, 3-isoxazolin-3-ila, 4isoxazolin-3-ila, 2-isoxazolin-4-ila, 3-isoxazolin-4-ila 4-isoxazolin-4-ila, 2-isoxazolin-5-ila, 3-isoxazolin-5-ila, 4-isoxazolin-5-ila, 2-isotiazolin-3-ila, 3-isotiazolin-3ila, 4-isotiazolin-3-ila, 2-isotiazolin-4-ila, 3 isotiazolin-4-ila, 4-isotiazolin-4-ila, 2-isotiazolin-5 ila, 3-isotiazolin-5-ila, 4-isotiazolin-5-ila, 2,3-dihidropirazol-l-ila, hydropirazol-3-ila, hydropirazol-5-ila, hydropirazol-3-ila, hydropirazol-5-ila, hydropirazol-3-ila, hydropirazol-5-ila, hydro-oxazol-3-ila, hydro-oxazol-5-ila, hydro-oxazol-3-ila, hydro-oxazol-5-ila, hydro-oxazol-3-ila, 1, 4,5-di4,5-di-hidropirazol-4-ila, 4,5-di2,3-di-hidro-oxazol-2-ila, 2,3-di2,3-di-hidro-oxazol-4-ila, 2,3-di3,4-di-hidro-oxazol-2-ila, 3,4-di3,4-di-hidro-oxazol-4-ila, 3,4-di3,4-di-hydro-oxazol-2-ila, 3,4-di3,4-di-hydro-oxazol-4-ila, piperidinila, 2-piperidinila, 3-piperidinila, 4piperidinila, pirazinila, morpholinila, tiomorflinila, 1,3 Petition 870220032852, dated 04 / 18 / 2022, p. 28 / 320 21 / 312 dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2piperazinyl, 1,3,5-hexahydrotriazin-2-yl, 1,2,4-hexahydrotriazin-3-yl, cycloserines, 2,3,4,5-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or 7-yl, 3,4,5,6-tetrahydro[2H]azepin-2- or -3- or -4- or 5- or -6- or -7-yl, 2,3,4,7-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,6,7-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or 7-yl, hexahydroazepin-1- or -2- or -3- or -4-yl, tetrahydro-oxepinyl such as 2,3,4,5-tetrahydro[1H]oxepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,4,7-tetrahydro[1H]oxepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,6,7-tetrahydro[1H]oxepin-2- or -3- or -4- or -5- or 6- or -7-yl, hexahydroazepin-1- or -2- or -3- or -4-yl, tetra- and hexahydro-1,3-diazepinyl,tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl, tetra- and hexahydro-1,3-dioxepinyl, tetra- and hexahydro-1,4-dioxepinyl. This definition also applies to heterocyclyl groups, as part of a substituent in a composite, for example, heterocyclylalkyl, etc., unless specifically defined otherwise.

[0057] The term heteroaryl or aromatic heterocyclic means a completely unsaturated 5- to 6-membered monocyclic ring system containing one to four oxygen, nitrogen, and sulfur group heteroatoms; if the ring contains more than one oxygen atom, these are not Petition 870220032852, dated 04 / 18 / 2022, page 29 / 320 22 / 312 directly adjacent; 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom: 5-membered heteroaryl groups that may contain, in addition to carbon atoms, one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, for example, (but not limited to) 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; 5-membered heteroaryl group linked to nitrogen containing one to four nitrogen atoms, or benzo-fused 5-membered heteroaryl group linked to nitrogen containing one to three nitrogen atoms: 5-membered heteroaryl groups that may contain, in addition to carbon atoms, one to four nitrogen atoms or one to three nitrogen atoms as ring members and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member may be bridged by a buta-1,3-diene group. 1,4-di-yl groups in which one or two carbon atoms may be replaced by nitrogen atoms, wherein these rings are attached to the skeleton by means of one of the nitrogen ring members, for example (but not limited to) 1-pyrrolyl, 1-pyrazolyl, 1,2,4-triazol-1-yl, 1-imidazolyl, 1,2,3-triazol-1-yl and 1,3,4-triazol-1-yl.

[0058] 6-membered heteroaryl containing one to four nitrogen atoms: 6-membered heteroaryl groups that, in addition to carbon atoms, may contain, respectively, one to three and one to four nitrogen atoms as members of Petition 870220032852, dated 04 / 18 / 2022, page 30 / 320 23 / 312 ring, for example, (but without limitation) 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl;5-membered benzofused heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one sulfur or oxygen atom: for example (but not limited to) indole-1-yl, indole-2-yl, indole-3-yl, indole-4-yl, indole-5-yl, indole-6-yl, indole-7-yl, benzimidazole-1-yl, benzimidazole-2-yl, benzimidazole-4-yl, benzimidazole-5-yl, indazole-1-yl, indazole-3-yl, indazole-4-yl, indazole-5-yl, indazole-6-yl, indazole-7-yl, indazole-2-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, l-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, l-benzothiophen-2-yl, 1-benzothiophen-3yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1benzothiophen-6-yl, 1-benzothiophen-7-yl, 1,3-benzothiazol-2yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,3-benzoxazol-2yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3benzoxazol-6-yl and 1,3-benzoxazol-7-yl;benzofused 6-membered heteroaryl containing one to three nitrogen atoms: for example (but without limitation) quinolin-2yl, 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.;

[0059] This definition also applies to heteroaryl as part of a composite substituent, for example, Petition 870220032852, dated 04 / 18 / 2022, p. 31 / 320 24 / 312 heteroarylalkyl etc., unless specifically defined elsewhere.

[0060] The term trialkylsilyl includes three branched and / or linear chain alkyl radicals attached and linked through a silicon atom, such as trimethylsilyl, triethylsilyl and t-butyl-dimethylsilyl. Halotrialkylsilyl denotes that at least one of the three alkyl radicals is partially or completely replaced with halogen atoms, which may be the same or different. The term alkoxytrialkylsilyl denotes that at least one of the three alkyl radicals is replaced with one or more alkoxy radicals, which may be the same or different. The term trialkylsilyl denotes a trialkylsilyl moiety fixed through oxygen.

[0061] Non-limiting examples of alkylcarbonyl include C(O)CH3, C(O)CH2CH2CH3 and C(O)CH(CH3)2. Non-limiting examples of alkoxycarbonyl include CH3OC(=O), CH3CH2OC(=O), CH3CH2CH2OC(=O), (CH3)2CHOC(=O) and the other butoxy or pentoxycarbonyl isomers. Non-limiting examples of alkylaminocarbonyl include CH3NHC(=O), CH3CH2NHC(=O), CH3CH2CH2NHC(=O), (CH3)2CHNHC(=O) and the different butylamino or pentylaminocarbonyl isomers. Non-limiting examples of dialkylaminocarbonyl include (CH3)2NC(=O), (CH3CH2)2NC(=O), CH3CH2(CH3)NC(=O), CH3CH2CH2(CH3)NC(=O) and (CH3)2CHN(CH3)C(=O). Non-limiting examples of alkoxyalkylcarbonyls include CH3OCH2C(=O), CH3OCH2CH2C(=O), CH3CH2OCH2C(=O), CH3CH2CH2CH2OCH2C(=O) and CH3CH2OCH2CH2C(=O). Non-limiting examples of alkylthioalkylcarbonyl include CH3SCH2C(=O), CH3SCH2CH2C(=O), CH3CH2SCH2C(=O), CH3CH2CH2CH2SCH2C(=O)e Petition 870220032852, dated 04 / 18 / 2022, page 32 / 320 25 / 312 CH3CH2SCH2CH2C(=O). The terms haloalkylsulfonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkylamino and the like are defined analogously.

[0062] Non-limiting examples of alkylaminoalkylcarbonyl include CH3NHCH2C(=O), CH3NHCH2CH2C(=O), CH3CH2NHCH2C(=O), CH3CH2CH2CH2NHCH2C(=O) and CH3CH2NHCH2CH2C(=O).

[0063] The term amide means A-R'C=ONR''-B, where R' and R'' indicate substituents, and A and B indicate any group.

[0064] The term thioamide means A-R'C=SNR''-B, where R' and R'' indicate substituents, and A and B indicate any group.

[0065] The total number of carbon atoms in a substituent group is indicated by the prefix C1-C1 where C1-C2 are numbers from 1 to 21. For example, C1-C3 alkylsulfonyl indicates methylsulfonyl by way of propylsulfonyl; C2 alkoxyalkyl designates CH3OCH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2. In the above recitations, when a compound of formula (I) comprises one or more heterocyclic rings, all substituents are attached to these rings through any carbon or nitrogen by substitution of a hydrogen on said carbon or nitrogen.

[0066] When a compound is replaced with a substituent bearing a superscript indicating that the number of substituents may exceed 1, said substituents (when Petition 870220032852, dated 04 / 18 / 2022, page 33 / 320 26 / 312 exceed 1) are selected independently from the defined group of substituents. Furthermore, when the subscript m in (R)m indicates an integer ranging from, for example, 0 to 4, then the number of substituents can be selected from the integers between 0 and 4 inclusive.

[0067] When a group contains a substituent that can be hydrogen, then when that substituent is considered to be hydrogen, it is recognized that the said group is not being substituted.

[0068] The embodiments in this document and the various advantageous features and 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 not to unnecessarily obscure the embodiments described in this document. The examples used in this document are intended merely to facilitate an understanding of the ways in which the embodiments in this document can be practiced and to further enable those skilled in the art to practice the embodiments in this document. Consequently, the examples should not be interpreted as limiting the scope of the embodiments in this document.

[0069] The description of the specific modalities will reveal so completely the general nature of the modalities in the present document that others may, applying current knowledge, readily modify and / or adapt them for various applications as specific modalities without departing from the generic concept and, therefore, such adaptations and Petition 870220032852, dated 04 / 18 / 2022, page 34 / 320 27 / 312 modifications should and are intended to be understood within the meaning and range of equivalents of the embodiments disclosed. It should be understood that the phraseology or terminology employed herein is for descriptive purposes and not for limitation. Therefore, although the embodiments herein have been described in terms of preferred embodiments, those skilled in the art will recognize that the embodiments herein may be practiced with modification within the spirit and scope of the embodiments as described herein.

[0070] Any discussion of documents, acts, materials, devices, articles and the like that have been included in this descriptive report is solely for the purpose of providing context for the disclosure. It should not be taken as an admission that any or all of these matters form part of the basis of the prior art or were of general common knowledge in the field relevant to the disclosure, as they existed anywhere prior to the priority date of this application.

[0071] The numerical values ​​mentioned in the description and in the description / claims, although they may form a crucial part of the present invention, any deviation from such numerical values ​​shall still fall within the scope of the present invention, provided that such deviation follows the same scientific principle of the present invention disclosed in the present invention. The inventive compound of the present invention may, where appropriate, be present as mixtures of different possible isomeric forms, especially stereoisomers, for example, E and Z, threo and erythro, and also Petition 870220032852, dated 04 / 18 / 2022, page 35 / 320 28 / 312 optical isomers, but, appropriately, also tautomers. Both E and Z isomers, as well as threo and erythro isomers, and optical isomers, any desired mixtures of these isomers and possible tautomeric forms are disclosed and claimed.

[0072] The term pest, for the purposes of this disclosure, includes, but is not limited to, fungi, stramenopyles (oomycota), bacteria, nematodes, mites, ticks, insects and rodents. In addition, a pest is an animal or plant that is harmful to humans or human affairs, including crops, livestock and forestry.

[0073] The term plant is understood in this document to mean all plants and plant populations, such as desired and undesired wild plants or wild plants (including naturally occurring crop plants). Crop plants may be plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including transgenic plants and including plant cultivars that may be protected and unprotected by plant breeders' rights.

[0074] For the purposes of this disclosure, the term plant includes a living organism of the type exemplified by trees, shrubs, herbs, grasses, ferns and mosses, which typically grow in one location, absorbing water and necessary substances through their roots and synthesizing nutrients in their leaves by photosynthesis.

[0075] Examples of plants for the purposes of the present invention include, but are not limited to, agricultural crops such as wheat, rye, barley, triticale, oats or rice; Petition 870220032852, dated 04 / 18 / 2022, pp. 36 / 320 29 / 312 beetroot, for example, sugar beet or fodder beet; fruits and fruit trees, such as pome fruits, stone fruits or soft fruits, for example, apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or currants; leguminous plants, such as lentils, peas, alfalfa or soybeans; oilseed plants, such as rapeseed, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, peanuts or soybeans; cucurbits, such as pumpkin, cucumber or melon; fiber plants, such as cotton, flax, hemp or jute; citrus fruits and citrus trees, such as oranges, lemons, grapefruits or tangerines; any horticultural plants, vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; Lauraceae plants, such as avocados, cinnamon or camphor; cucurbitaceae; oilseed plants;Raw material and energy plants, such as cereals, corn, soybeans, other legumes, rapeseed, sugarcane or palm oil; tobacco; nuts; coffee; tea; cocoa; bananas; peppers; grapevines (table grapes and juice grapes); hops; grass; sweetleaf (also called Stevia); natural rubber plants or ornamental and forest plants, such as flowers, shrubs, broadleaf trees or evergreens, for example, conifers; and plant propagation material, such as seeds, and harvesting material from these plants.

[0076] Preferably, the plant for the purpose of the present invention includes, but is not limited to, cereals, corn, rice, soybeans and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus fruits and citrus fruits, any horticultural plants, Petition 870220032852, dated 04 / 18 / 2022, page 37 / 320 30 / 312 cucurbits, oilseed plants, tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton, potato, tomato, onion, pepper and vegetables, ornamental plants, any floricultural plants and other plants for human and animal use.

[0077] The term plant parts is understood to mean all parts and organs of plants above and below ground. For the purpose of the present disclosure, the term plant parts includes, but is not limited to, cuttings, leaves, branches, tubers, flowers, seeds, twigs, roots including taproots, lateral roots, rot hairs, rot apex, root cap, rhizomes, wedges, buds, fruits, fruit bodies, bark, stem, flowers, auxiliary flowers, meristems, nodes, and internodes.

[0078] The term "site of the same" includes soil, plant surroundings or plant parts, and equipment or tools used before, during, or after sowing / planting a plant or a plant part.

[0079] The application of the compounds of the present disclosure or of the compound of the present disclosure in a composition that optionally comprises other compatible compounds to a plant or plant material or part thereof includes application by a technique known to a person skilled in the art, which includes, but is not limited to, spraying, coating, dipping, fumigating, impregnating, injecting and dusting.

[0080] The term applied means adhered to a plant or part of a plant, whether including chemically or physically including impregnation.

[0081] In one embodiment, the present invention provides a compound of formula (I), Petition 870220032852, dated 04 / 18 / 2022, pp. 38 / 320 31 / 312 (X) Formula (I) where, R1 is selected from the group consisting of C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C8 cycloalkyl and C3-C8 cycloalkylC1-C6 alkyl; Y is selected independently of O or NRY; RY is selected from the group consisting of hydrogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C3-C5-cycloalkyl and C3-C5-cycloalkyl-C1-C3-alkyl; A represents N or CR2; G represents either N or C; since both G's are not simultaneously nitrogen; R2 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)o-iR9=NR10, N=S(O)oi(R9) 2, P(=O)(ou') 2,Si(R') 3, C6-C10-aryl, C7-C14-aralkyl and C3C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more R2a groups, and the cyclic R2 groups may be optionally substituted with one or more R2b groups; R2a is selected from the group consisting of Petition 870220032852, dated 04 / 18 / 2022, pp. 39 / 320 32 / 312 halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2Ce-alkynyl, C1-C6-haloalkyl, C3-Cs-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)o-2R7, C(=O)R8, S(O)o-iR9=NR10, N=S(O)oi(R9)2, Sí(R')3, Ce-Cio-aryl, C7-Ci4-aralkyl and C3-Cio-heterocyclyl; R2 is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)o-2R7, C(=O)R8, Si(R')3, S(O)o-iR9=NR1oe N=S(O)oi(R9)2; or two R2a substituents or two R2b substituents together with the atom to which they are attached or together with additional atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)o-2 and Si(R')2 can form a ring of 3 to 7 members, which in turn can be substituted with one or more R2ab groups; R2abé selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2C6-haloalkenyl, C3-C5-cycloalkyl, OR4, NR5R6, S(O)o-2R7, S(O)o-iR9=NR1o, N=S(O)oi(R9)2, Sí(R')s, C6Cio-aryl, C7-Ci4-aralkyl and C3-Cio-heterocyclyl; Q represents a partially saturated or unsaturated 5- to 12-membered heterocyclic ring system that may optionally be substituted with one or more R3 groups; wherein said heterocyclic ring system does not represent unsubstituted benzothiazolyl and unsubstituted N-methylbenzimidazolyl; Petition 870220032852, dated 04 / 18 / 2022, p. 40 / 320 33 / 312 R3 is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)o-2R7, C(=O)R8, S(O)o-iR9=NR10, N=S(O)oi(R9)2, P(=O)(or')2, Si(R')s, C6C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; wherein each aliphatic group may optionally be substituted with one or more groups of R3a, and the cyclic groups of R3 may optionally be substituted with one or more groups of R3b; R3a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2C6-alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)0-1R9=NR10, N=S(O)oi(R9)2, Si(R')3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; R3bé selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, C(R')2-NR5R6, C(R')2-OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)0-1R9=NR10, N=S(0)oi(R9)2, Si(R')3, C6a-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; Two R3a or two R3b substituents together with the atom to which they are attached, or together with more atoms selected from the group consisting of C, N, O, S, and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O) and Si(R')2, can form a ring of 3 to 7 members, which in turn can be Petition 870220032852, dated 04 / 18 / 2022, p. 41 / 320 34 / 312 substituted by one or more R3ab groups; wherein R3ab is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6haloalkyl, C3-C8-cycloalkyl, OR4, NR5R6 and S(O)O2R7; Two R3s together with the atom to which they are attached, or together with more atoms selected from the group consisting of C, N, O, S, and optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O)m and Si(R')2, can form a ring of three to seven members, which in turn can be replaced by one or more groups selected from the group consisting of halogen, cyan, R3c, OR3c, SR3c, NR3c2, Si(R3c)3, COOR3c and CONR3c2; R3 is selected from the group consisting of C1-C6-alkyl and C3-8-cyclic alkyl in hydrogen, halogen, straight chain or branched chain; wherein each R3 group is optionally substituted by one or more halogens; Ring E represents a 5- or 6-membered heterocyclic ring fused to ring D; where ring E is optionally replaced by one or more R11 groups; R11 is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)o-2R7, C(=O)R8, S(O)o-1R9=NR10, N=S(O)oi(R9)2, P(=O)(or')2, Si(R')s, C6C10-aryl, C7-C14-aralkyl and C3-C1o-heterocyclyl; wherein each aliphatic group may optionally be substituted with one or more groups of R11a, and the groups Petition 870220032852, dated 04 / 18 / 2022, p. 42 / 320 35 / 312 cyclic R11 components can optionally be replaced with one or more R11b groups; R11a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2C6-alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR4, CR4=NR5, NR5R6, S(O)o-2R7, C(=O)R8, S(O)o-iR9=NR10, N=S(O)oi(R9)2, Si(R')3, C6-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; R11bé selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR4, C(R')2-NR5R6, C(R')2-OR4, CR4=NR5, NR5R6, S(O)0-2R7, C(=O)R8, S(O)0-1R9=NR10, N=S(0)oi(R9)2, Si(R')3, C6a-C10-aryl, C7-C14aralkyl and C3-C10-heterocyclyl; R4 is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, S(O)2R7, Si(R')s, C6-C10-aryl, C7-C14-aralkyl and C3-C10heterocyclyl; wherein each aliphatic group may be optionally substituted with R4 and cyclic groups of R4 may be optionally substituted with one or more groups of R4b; R4a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, or', NR'R'', S(O)o-2R', C(=O)R', Si(R')3, C6-C10-aryl, C7C14-aralkyl and C3-C10-heterocyclyl; R4bé selected from the group consisting of halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6. Petition 870220032852, dated 18 / 04 / 2022, page 43 / 320 36 / 312 alkynyl, Ci-Ce-haloalkyl, C2-Ce-haloalkenyl, C3Cs-cycloalkyl OR', NR'R'', S(O)o-2R', C(=O)R', Si(R')3, Ce-Cio-aryl, C?-Ci4-aralkyl and C3-C10heterocyclyl; R5 is selected from the group consisting of hydrogen, C1-C1-alkyl, C2-C1-alkenyl, C2-C1-alkynyl, C1-C1-haloalkyl, C2-C1-haloalkenyl, C3-C1-C2-cycloalkyl, OR4, NR'R'', S(O)O-2R7, C(=O)R8, Si(R')3, C1-C1-Aryl, C7-C14-Alkynyl and C3-C1-C1-Heterocyclyl; wherein each aliphatic group may optionally be substituted with R5a, and the cyclic groups of R5 may optionally be substituted with one or more groups of R5b; R5a is selected from the group consisting of halogen, cyano, C1-C1-alkyl, C2-C1-alkenyl, C2-C1-alkynyl, C1-C1-haloalkyl, C3-C1-cycloalkyl, OR', NR'R'', S(O)O-2R', C(=O)R', Si(R')3, C1-C1-aryl, C7C14-aralkyl and C3-C1-heterocyclyl; R5bé selected from the group consisting of halogen, cyano, C1-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, C1-Ce-haloalkyl, C2-Ce-haloalkenyl, C3Cs-cycloalkyl, ou', NR'R'', S(O)o-2R', Si(R')3, C(=O)R', Ce-Cio-aryl, C7-Ci4-aralkyl and Cs-Cio-heterocyclyl; Reé is selected from the group consisting of hydrogen, C1-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, C1-Ce-haloalkyl, C2-Ce-haloalkenyl, C1-Ce-cycloalkyl and C(=O)R8; R7 is selected from the group consisting of CiCe-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Cehaloalkyl, C2-Ce-haloalkenyl, C3-Cs-cycloalkyl, NR5Re, Petition 870220032852, dated 04 / 18 / 2022, page 44 / 320 37 / 312 C7-C10-aryl, C7-C14-aralkyl and C3-C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more R7a groups, and the cyclic R7 groups may be optionally substituted with one or more R7b groups; R7a is selected from the group consisting of halogen, cyano, C1-C1-alkyl, C2-C1-alkenyl, C2-C6-alkynyl, C1-C1-haloalkyl, C3-C5-cycloalkyl, OR', NR'R'', S(O)q-2R', C(=O)R', C1-C1-aryl, C7-C1-C1-aralkyl and C3-C1-heterocyclyl; R7bé selected from the group consisting of halogen, cyano, C1-C1-alkyl, C2-C1-alkenyl, C2-C6-alkynyl, C1-C1-haloalkyl, C2-C1-haloalkenyl, C3C5-cycloalkyl, or', NR'R'', S(O)q-2R', C(=O)R', C1C1-aryl, C7-C14-aralkyl and C3-C1C1-heterocyclyl; R8 is selected from the group consisting of hydrogen, C1-C1-alkyl, C2-C1-alkenyl, C2-C1-alkynyl, C1-C1-haloalkyl, C2-C1-haloalkenyl, C3-C8-cycloalkyl, OR4, NR5Re, N=S(O)oi(R9)2, C1-C1-aryl, C7-C14-aralkyla and C3C1-heterocyclyl; wherein each aliphatic group may optionally be substituted with one or more R8a groups, and the cyclic R8 groups may optionally be substituted with one or more R8b groups; R8a is selected from the group consisting of halogen, cyano, C1-C1-alkyl, C2-C1-alkenyl, C2-C1-alkynyl, C1-C1-haloalkyl, C3-C1-cycloalkyl, OR', NR'R'', S(O)q-2R', C(=O)R', C1-C1-aryl, C7-C1-C1-aralkyl and C3-C1-heterocyclyl; R8bé selected from the group consisting of halogen, cyano, C1-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, C1-Ce-haloalkyl, C2-Ce-haloalkenyl, C3Petition 870220032852, dated 18 / 04 / 2022, page 45 / 320 38 / 312 Cs-cycloalkyl, or', NR'R'', S(O)o-2R', C(=O)R', C6Cio-aryl, C'-Ci4-aralkyl and C3-Cio-heterocyclyl; R9 is selected from the group consisting of CiCe-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Cehaloalkyl, C2-Ce-haloalkenyl, C3-Cs-cycloalkyl and C(=O)R8; Rioé is selected from the group consisting of hydrogen, cyano, C1-Ce-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl, C1-Ce-haloalkyl, C2-Ce-haloalkenyl, C3-C8-cycloalkyl, Si(R')3, S(O)o-2R7 and C(=O)R8; R' is selected from the group consisting of halogen, cyano, R'', OR'', N(R'')2, S(O)o-2R'', C(=O)R'', C(=O)ou'' and C(=O)N(R'')2R8; R'' is selected from the group consisting of hydrogen, C1-C1-alkyl, C2-C1-alkenyl, C2-C6-alkynyl, C1-C1-haloalkyl and C3-C8-cycloalkyl; wherein each may be optionally substituted with halogen; Each group of Ria Rii, R2a, R2b, R2ab, R3a, R3b, R3ab, R3c, R4a, R4b, R5a, R5b, R7a, R7b, R8a and R8b may optionally be replaced by one or more groups selected from the group consisting of halogen, cyano, R', ou', SR', N(R')2, COOR' and CON(R')2; m is an integer in a range from 0 to 2; or agrochemically acceptable salts, structural isomers / isomers, stereoisomers, diastereomers, enantiomers, tautomers, polymorphs, metal complexes or N-oxides thereof.

[0082] In another embodiment, the compound of formula (I) is represented by the compound of formula (IA); Petition 870220032852, dated 04 / 18 / 2022, p. 46 / 320 39 / 312 Formula (IA)

[0083] In yet another embodiment, the compound of formula (I) is represented by the compound of formula (IB); Formula (IB)

[0084] In one embodiment, Q is selected from the group consisting of the formula Qi to Q10: 02 Q3 where Gi, G2, G4, and G5 independently represent N or CR3; G3 is NR6, O, or S; Z is O or S; and en is an integer in a range from 0 to 4.

[0085] In a preferred embodiment, Q is selected from the group consisting of Q1a to Q10b: Petition 870220032852, dated 04 / 18 / 2022, p. 47 / 320 40 / 312 o Q10b where # denotes the point of attachment to ring D, R6 is selected from the group consisting of hydrogen, C1-C6-alkyl and C3-10-cyclic alkyl; wherein each group of R6 is optionally replaced by one or more halogens, en is an integer in a range from 0 to 4.

[0086] In one embodiment, the present invention provides a compound of formula (I), wherein at least one nitrogen is present in the fused ring system DE.

[0087] In another embodiment, the DE fused ring system is selected from the group consisting of DE-1 to Petition 870220032852, dated 04 / 18 / 2022, page 48 / 320 41 / 312 DE-15: where # denotes the point of union to the ring Q and · denotes the point of union to the group -S(Y)mR1.

[0088] In a preferred embodiment, the present invention provides a compound of formula (I) wherein Q is selected from Q1a, Q1b, Q1c, Q1h, Q2b, Q3a, Q5b, Q5d, Q6a, Q6b, Q9a, Q9b Q7a or Q8a; where # denotes the point of union to the D-ring; R3 is selected from the group consisting of Petition 870220032852, dated 04 / 18 / 2022, page 49 / 320 42 / 312 halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl and S(Y)o-2R7; R6 is selected from the group consisting of hydrogen, C1-C1-alkyl and C3-C1-cycloalkyl; R7 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6haloalkyl, C2-Ce-haloalkenyl, C3-Cs-cycloalkyl; DE fused rings are selected from the group consisting of where # denotes the point of union to the ring Q and · denotes the point of union to the group -S(Y)mR1; R2 is selected from the group consisting of halogen, cyano, C1-C1-alkyl, C1-C1-haloalkyl, C3-C8-cycloalkyl, C6-C8-aryl, C1-C1-aralkyl and C3-C6-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more R2a groups, and the cyclic groups of R2 may be optionally substituted with one or more R2b groups; m is an integer in the range of 0 to 2; n is an integer in the range of 0 to 4; Riiae is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR4, NR5R6, C6-C10-aryl, C1-C14-aralkyl and C3C10-heterocyclyl; wherein each aliphatic group may be optionally substituted with one or more Riiae groups. Petition 870220032852, dated 04 / 18 / 2022, p. 50 / 320 43 / 312 cyclic groups of R11 can optionally be replaced with one or more groups of R11b.

[0089] In another preferred modality, the compound of formula (I) is selected from 2-(1-(3,5dichlorofenil)-2-(ethylsulfonyl)indolizin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2(ethylsulfonyl)imidazo[1,2-a]pyridin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 6-(1-bromo-2-(ethylsulfonyl)indolizin-3-yl)-7-methyl-3-(trifluoromethyl)7H-imidazo[4,5-c]pyridazine; 2-(2(ethylsulfonyl)imidazo[1,2-a]pyridin-3-yl)-5(trifluoromethyl)benzo[d]oxazole; 2-(2-(ethylsulfonyl)-7-(trifluoromethyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)3H-imidazo[4,5-b]pyridine; 2-(8-(3,5-dichlorophenyl)-2(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)3H-imidazo[4,5-b]pyridine; 2-(1-(3,5-dichlorophenyl)-2(ethylsulfonyl)-7-(trifluoromethyl)indolizin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-(3,5dichlorophenyl)-2-(ethylsulfonyl)indolizin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine;2-(2-(ethylthio)5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2(ethylsulfonyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine;2-(2(ethylthio)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl) -3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine;2-(2(ethylsulfonyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine;2-(2(ethylthio)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl) -5((trifluoromethyl)thio)benzo[d]oxazol;2-(2Petição 870220032852, of 18 / 04 / 2022, page 51 / 320; 44 / 312 (ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine;2-(2(ethylsulfonyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl) -5((trifluoromethyl)sulfonyl)benzo[d]oxazole;2-(2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine;2-(2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl) -5((trifluoromethyl)thio)benzo[d]oxazole;2-(2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(2-(ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2 - (2-(ethylthio)7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2(ethylsulfonyl)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-c]pyridine;2-(2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3,5dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(4(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2(ethylthio)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5Petição 870220032852, de 18 / 04 / 2022, pág. 52 / 320; 45 / 312 a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2(ethylsulfonyl)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-c]pyridine; 2-(2-(ethylthio)-7-(4(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5((trifluoromethyl)thio)benzo[d]oxazole; 2-(2-(ethylsulfonyl)-7(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(2-(ethylthio)-7(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5((trifluoromethyl)thio)benzo[d]oxazole; 2-(2-(ethylsulfonyl)-7(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(7-(4chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine;2-(7(4-chlorofenil)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3yl)-3-metil-6-(trifluorometil)-3H-imidazo[4,5-c]pyridine; 2-(7-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3yl)-5-((trifluoromethyl)thio)benzo[d]oxazole; 2-(7-(4chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3yl)-5- ((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(7-(3,5dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5 Petition 870220032852, de 18 / 04 / 2022, pág. 53 / 320 46 / 312 a]pyrimidin-3-yl)-5-((trifluoromethyl)thio)benzo[d]oxazol; 2(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-5((trifluoromethyl)sulfonyl)benzo[d]oxazol; 2-(2-(ethylthio)-5phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2 - (2 - (ethylthio)5-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-c]pyridine;2-(2(ethylsulfonyl)-5-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine;2-(2(ethylsulfonyl)-5-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine;2-(6chloro-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2 - (2 - (ethylthio)6-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-chloro-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine;2 - (2 - (ethylthio)5-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(6chloro-2 - (ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(6-chloro-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2(ethylsulfonyl)-6-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2(ethylthio)-5-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5-(4(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3Petição 870220032852, dated 18 / 04 / 2022, pág. 54 / 320; 47 / 312 methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2(ethylthio)-5-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl) -3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5-(4fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine;2-(2-(ethylsulfonyl)-5-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-5-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-(4-chlorofenil)-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-metil-6(trifluorometil)-3H-imidazo[4,5-b]pyridine;2 - (2 - (ethylthio)6-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(5-(3,5dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2(ethylsulfonyl)-6-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(5(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine; 2-(5-(3,5-dichlorophenyl)-2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(5-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; Petition 870220032852, 18 / 04 / 2022, pág. 55 / 320 48 / 312 2-(6-bromo-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6bromo-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; - (6-(4-chlorofenil)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-metil-6-(trifluorometil)-3Himidazo[4,5-c]pyridine; 2-(2-(ethylthio)-5-(4-(1,1,2,2tetrafluoroethoxy)fenil)pyrazolo[1,5-a]pyrimidin-3-yl)-3metil-6-(trifluorometil)-3H-imidazo[4,5-c]pyridine; 2-(6(3,5-dichlorofenil)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-metil-6-(trifluorometil)-3Himidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5-(4-(1,1,2,2tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2(ethylsulfonyl)-5-(4-(1,1,2,2tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2(ethylsulfonyl)-5-(4-(1,1,2,2tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine;2-(6-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-c]pyridine; 2-(2-(ethylthio)-6-(4(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3Petição 870220032852, de 18 / 04 / 2022, pág. 56 / 320; 49 / 312 methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(5-(4-chlorophenyl)-2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(5-(4chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-6-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-c]pyridine; 2-(2-(ethylthio)-7-(4-(1,1,2,2tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(5(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; - (5- (4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(4-(1,1,2,2tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(4-(1,1,2,2tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 3-(7(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3yl)-7 - (trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine; 2(2- (ethylthio)-7-(4-(1,1,2,2tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 3-(7(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[4,3Petição 870220032852, de 18 / 04 / 2022, pág. 57 / 320 50 / 312 a]pyridine; 2-(2-(ethylthio)-6-(4-(1,1,2,2tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2(ethylsulfonyl)-6-(4-(1,1,2,2tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7(3-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3,5-difluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-6-(4(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7(3,5-difluorofenil)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-metil-6-(trifluorometil)-3Himidazo[4,5-b]pyridine;2-(7-(3-chloro-5-fluorophenyl)-2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3-chloro5-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3,4-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 7-(3,5-dichlorophenyl)-2-(ethylthio)-3(1-methyl-5-(trifluoromethyl)-1H-benzo[d]imidazol-2yl)pyrazolo[1,5-a]pyrimidine; 2-(ethylthio)-3-(1-methyl-5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)pyrazolo[1,5a]pyrimidine; 7-(3,5-dichlorofenil)-2-(ethylsulfonyl)-3-(1metil-5-(trifluorometil)-1H-benzo[d]imidazol-2Petição 870220032852, de 18 / 04 / 2022, pág. 58 / 320 51 / 312 yl)pyrazolo[1,5-a]pyrimidine; 2-(ethylsulfonyl)-3-(1-methyl5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)pyrazolo[1,5a]pyrimidine; 2-(2-(ethylsulfonyl)-6-(4-(1,1,2,2tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 3-(7(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine; 3(7-(3,5-dichlorofenil)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3a]pyridine; 2-(7-(2,3-dichlorofenil)-2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-metil-6(trifluorometil)-3H-imidazo[4,5-b]pyridine; 2 - (2 - (ethylthio)7-fenilpyrazolo[1,5-a]pyrimidin-3-yl)-3-metil-6(trifluorometil)-3H-imidazo[4,5-b]pyridine; 2-(7-(2,3dichlorofenil)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3yl)-3-metil-6-(trifluorometil)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-fenilpyrazolo[1,5-a]pyrimidin-3-yl)3-metil-6-(trifluorometil)-3H-imidazo[4,5-b]pyridine;2-(7(4-chloro-3-fluorophenyl)-2-(ethylthio)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine; 2-(7-(3,5-dichlorophenyl)-2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(4-chloro3-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; - (7 - (4-chloro-3-fluorophenyl)-2-(ethylthio)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-c]pyridine; 2-(7-(2,4-dichlorophenyl)-2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(2,4 Petition 870220032852, 18 / 04 / 2022, pág. 59 / 320 52 / 312 dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(2,4-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-c]pyridine; 2-(7-(3-chloro-5-fluorophenyl)-2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3-chloro5-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3,5-bis(trifluoromethyl)phenyl)-2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)7-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7(3,5-bis(trifluorometil)fenil)-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-metil-6(trifluorometil)-3H-imidazo[4,5-b]pyridine; 2-(2(ethylsulfonyl)-7-(3-(trifluorometil)fenil)pyrazolo[1,5a]pyrimidin-3-yl)-3-metil-6-(trifluorometil)-3Himidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(3fluorofenil)pyrazolo[1,5-a]pyrimidin-3-yl)-3-metil-6(trifluorometil)-3H-imidazo[4,5-b]pyridine; 2 - (2 - (ethylthio)7-metilpyrazolo[1,5-a]pyrimidin-3-yl)-3-metil-6(trifluorometil)-3H-imidazo[4,5-b]pyridine; 2 - (2 - (ethylthio)7-(3-fluorofenil)pyrazolo[1,5-a]pyrimidin-3-yl)-3-metil-6(trifluorometil)-3H-imidazo[4,5-c]pyridine;2-(2(ethylsulfonyl)-7-methylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2Petition 870220032852, dated 04 / 18 / 2022, page 60 / 320; 53 / 312 (ethylthio)-7-(3-(trifluoromethyl)phenyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-c]pyridine; (7-(3,5-dichlorophenyl)-3-(3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine-2yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(imino)-X6sulfanone; 2-(2-(ethylsulfonyl)-7-(3(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2(ethylsulfonyl)-7-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2 - (2 - (ethylthio)-7-methylpyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7(3-chloro-4-fluorophenyl)-2-(ethylthio)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5,7bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2(ethylsulfonyl)-5,7-bis(trifluoromethyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine;2-(ethylthio)-3-(3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one; 2-(7-bromo-2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2(ethylsulfonyl)-N-methyl-3-(7-(trifluoromethyl)[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)pyrazolo[1,5a]pyrimidin-7-amine; 6-(8-(4-chloro-3-fluorofenil)-2(ethylsulfonyl)indolizin-3-yl)-7-metil-3-(trifluorometil)7H-imidazo[4,5-c]pyridazine; 2-(2-(ethylsulfonyl)-7-(5metil-3-(trifluorometil)-1H-pyrazol-1-yl)pyrazolo[1,5Petição 870220032852, de 18 / 04 / 2022, pág. 61 / 320; 54 / 312 a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(ethylthio)-N-methyl-3-(3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2yl)pyrazolo[1,5-a]pyrimidin-7-amine; 2-(2-(ethylsulfonyl)-7(3-fluorophenoxy)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 6-(8-(4-chloro3-fluorophenyl)-2-(ethylsulfonyl)imidazo[1,2-a]pyridin-3-yl)7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine; 2(6-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyrazine; 4-(2-(ethylsulfonyl)-3-(7-methyl-3-(trifluoromethyl)-7Himidazo[4,5-c]pyridazin-6-yl)indolizin-8-yl)-2fluorobenzonitrile; 2-(8-(cyclopropylmethyl)-2-(ethylsulfonyl)imidazo[1,2-a]pyridin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(4-chloro1H-pyrazol-1-yl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine;2 - (2-(ethylsulfonyl)-7-(5-methyl-1H-1,2,4-triazol-1yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(1-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(1-methyl-3(trifluoromethyl)-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidin3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-ciclopropyl-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin3-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrazine; 2(2-(ethylsulfonyl)-7-(1-metil-3-(trifluorometil)-1H-pyrazol5-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-7(trifluorometil)imidazo[1,2-c]pyrimidina; 4-(2Petição 870220032852, de 18 / 04 / 2022, pág. 62 / 320; 55 / 312 (ethylsulfonyl)-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridin2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)morpholine; 2-(7 - (4chloro-3-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[1,5c]pyrimidine; 2-(2-(ethylsulfonyl)-7-(1H-1,2,4-triazol-1yl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-c]pyrimidine; 2 - (2 - (ethylsulfonyl)-5,7bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 6-(1-bromo-2(ethylsulfonyl)-8-methylindolizin-3-yl)-7-methyl-3(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine; 6-(8-bromo-2(ethylsulfonyl)indolizin-3-yl)-3-(difluoromethyl)-7-methyl-7Himidazo[4,5-c]pyridazine; 2-(2-(ethylsulfonyl)-7methoxypyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2(ethylsulfonyl)-7-(methylthio)pyrazolo[1,5-a]pyrimidin-3-yl)3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine;2-(ethylsulfonyl)-3-(3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7(4H)thione; 2-(2-(ethylsulfonyl)-7-(1,1,2,2tetrafluoroethoxy)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-ethoxy-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6(trifluoromethyl)imidazo[1,2-a]pyrazine; diethyl((2(ethylsulfonyl)-3-(6-(trifluoromethyl)imidazo[1,2-a]pyrazin2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)imino)-16-sulfanone; 2(ethylsulfonyl)-N,N-dimethyl-3-(3-methyl-6-(trifluoromethyl)3H-imidazo[4,5-b]pyridin-2-yl)imidazo[1,2-a]pyridin-8amine; 6-(2-(ethylsulfonyl)-7-(5-(trifluoromethyl)pyridin-2yl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-methyl-3Petição 870220032852, de 18 / 04 / 2022, pág. 63 / 320; 56 / 312 (trifluoromethyl)-7H-imidazo[4,5-c]pyridazine; 2-(7-(4chloro-3-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-3,5-dimethyl-6-(trifluoromethyl)-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-ona; 2-(2-(ethylsulfonyl)7-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyrazolo[1,5a]pyrimidin-3-yl)-3,5-dimethyl-6-(trifluoromethyl)-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-ona; 2-(7-(3-chloro-5fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrazine; 2(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-7-(trifluoromethyl)imidazo[1,2c]pyrimidine; 2-(7-(4-chloro-3-fluorophenyl)-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-methyl-7(trifluoromethyl)-[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one; 2-(7-(5-chloropyridin-2-yl)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5a]pyridine;2-(2-(ethylsulfonyl)-7-(5-methyl-3(trifluoromethyl)-1H-pyrazol-1-yl)pyrazolo[1,5-a]pyrimidin3-yl)-6-methyl-7-(trifluoromethyl)-[1,2,4]triazolo[1,5c]pyrimidin-5(6H)-one; 2-(2-(ethylsulfonyl)-7-(3(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyrazolo[1,5a]pyrimidin-3-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[1,5c]pyrimidine; ethyl(3-(3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-c]pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-2yl)(methylimino)-16-sulfanone.;

[0090] The compounds of the present invention may exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers, and geometric isomers. A person skilled in the art will observe that one stereoisomer may be more active and / or may exhibit effects Petition 870220032852, dated 04 / 18 / 2022, page 64 / 320 57 / 312 beneficial when enriched with respect to another stereoisomer (or stereoisomers) or when separated from another stereoisomer (or stereoisomers). Additionally, the person skilled in the art knows how to selectively separate, enrich and / or prepare said stereoisomers. The compounds of the present invention may be present as a mixture of stereoisomers, individual stereoisomers as an optically active form.

[0091] An anion portion of the salt in the case of the compound of formula (I) being cationic or having the capacity to form a cation may be inorganic or organic. Alternatively, a cation portion of the salt in the case of the compound of formula (I) being anionic or having the capacity to form an anion may be inorganic or organic. Examples of inorganic anion portions of the salt include, but are not limited to, chloride, bromide, iodide, fluoride, sulfate, phosphate, nitrate, nitrite, hydrogen carbonates, and hydrogen sulfate. Examples of the organic anion portion of salts include, but are not limited to, formate, alkanoates, carbonates, acetates, trifluoroacetate, trichloroacetate, propionate, glycolate, thiocyanate, lactate, succinate, malate, citrates, benzoates, cinnamates, oxalates, alkyl sulfates, alkyl sulfonates, aryl sulfonates, aryl disulfonates, alkyl phosphonates, aryl phosphonates, aryl diphosphonates, p-toluene sulfonate, and salicylate.Examples of inorganic cation moieties of the salt include, but are not limited to, alkali and alkaline earth metals. Examples of organic cation moieties of the salt include, but are not limited to, pyridine, methylamine, imidazole, benzimidazole, hitidine, phosphazene, tetramethylammonium, tetrabutylammonium, choline, and trimethylamine. Petition 870220032852, dated 04 / 18 / 2022, page 65 / 320 58 / 312

[0092] The metal ions in metal complexes of the compound of formula (I) are especially the ions of the elements of the second main group, especially calcium and magnesium, of the third and fourth main groups, especially aluminum, tin and lead, and also of the first to eighth transition groups, especially chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Particular preference is given to the metal ions of the elements of the fourth period and the first to eighth transition groups. Here, the metals may be present in the various valences they can assume.

[0093] In one embodiment, the present invention provides a compound of formula (I), agriculturally acceptable salts, metal complexes, constitutional isomers, stereoisomers, diastereoisomers, enantiomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, geometric isomers or Noxides thereof and its composition with the excipient, inert carrier or any other essential ingredient such as surfactants, additives, solid diluents and liquid diluents.

[0094] The compounds of formula (I), (including all stereoisomers, N-oxides and salts thereof), typically exist in more than one form, and formula (I) therefore includes all crystalline and non-crystalline forms of the compounds that formula (I) represents. Non-crystalline forms include modalities that are solid, such as waxes and gums, as well as modalities that are liquid, such as solutions and melts. Crystalline forms include modalities that essentially represent a single crystal type and modalities that represent a mixture of polymorphs (this Petition 870220032852, dated 04 / 18 / 2022, p. 66 / 320 59 / 312 is, different crystalline types). The term polymorph refers to a particular crystalline form of a chemical compound that can crystallize into different crystalline forms, where these forms have different arrangements and / or conformations of the molecules in the crystal structure. Although polymorphs may have the same chemical composition, they may also differ in composition due to the presence or absence of co-crystallized water molecules or other molecules, which may be weakly or strongly bound in the structure. Polymorphs may differ in such chemical, physical, and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, ability to form suspensions, dissolution rate, and bioavailability.A person skilled in the art will observe that a polymorph of a compound represented by formula (I) may exhibit beneficial effects (e.g., suitability for preparing useful formulations, enhanced biological performance) with respect to another polymorph or a mixture of polymorphs of the same compound represented by formula (I). The preparation and isolation of a particular polymorph of a compound represented by formula (I) may be achieved by methods known to those skilled in the art, including, for example, crystallization using selected solvents and temperatures.

[0095] In one embodiment, the present invention provides a process for preparing the compound of formula (I) or agriculturally acceptable salts.

[0096] The compound of formula (I) can be prepared according to the schemes: 1-23 / examples described in this document. Petition 870220032852, dated 04 / 18 / 2022, page 67 / 320 60 / 312

[0097] The process for preparing compound of formula (I), more specifically, compound of formula (Ia) or compound of formula (Ib) where Q is Q1 or Q2 comprises the reaction of compound of formula (2), with compound of formula (3) or (4), where M is O, S, NR' to obtain compound of formula (Ia) and (Ib). The process is summarized in diagram 1: Diagram: 1 R1i where R1, R3, A, G, Gi, G2, G3, G4, G5, E, men have the meanings described above.

[0098] The compound of formula (3) and formula (4) are commercially available or can be prepared using methods known or analogously described in documents US200369257, WO200665703, WO2009131237, WO2010125985, WO2011043404, WO2011040629, WO2012086848, WO2013018928 and WO2015000715.

[0099] In scheme 1, the carboxylic acid group present in the compound of formula (2) can be converted into a more reactive functional group, such as an acyl halide, mixed anhydride, acyl azide, N-acylbenzotriazoles, active esters or by means of in situ activation by reagents of Petition 870220032852, dated 04 / 18 / 2022, page 68 / 320 61 / 312 Peptide coupling, such as bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl); dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), followed by amide bond formation with compound of formula (3) in solvents such as dichloromethane, dichloroethane, N,N-dimethylacetamide, tetrahydrofuran, acetonitrile or a mixture thereof to obtain the compound of formula (5). Organic non-nucleophilic bases such as triethylamine, ethyldiisopropylamine, pyridine, N-methylpyrrolidine, 1,8-diazabicyclo[5.4.0]undec-7-ene may be used. The reaction can be carried out at a temperature in a range of about 0 °C to about 150 °C.

[0100] The compound of formula (5) can be converted into a compound of formula (Ia) by means of dehydration, following conventional conditions or under microwaves, in the presence of a catalyst, for example, methanesulfonic acid or para-toluenesulfonic acid, in an inert solvent such as N-methylpyrolidine at a temperature in a range of about 25 °C and about 185 °C. Such processes were described in documents WO2009131237, WO2010125985, WO2011043404, WO2011040629, WO2012086848, WO2013018928, WO2015000715 and WO2015121136.

[0101] Alternatively, the compound of formula (5) can be converted into a compound of formula (Ia) wherein M is oxygen under Mitsunobu conditions well known to those skilled in the art with the use of di-isopropyl triphenyl phosphine azodicarboxylate in an inert solvent such as diethyl ether tetrahydrofuran at a temperature in a range of about 25 °C and about 50 °C. This process was previously described in document WO2009131237. Petition 870220032852, dated 04 / 18 / 2022, p. 69 / 320 62 / 312

[0102] Applying the methods of scheme 1 to the reaction of the compound of formula (2) with the compound of formula (4) can give rise to the compound of formula (Ib).

[0103] A process for the synthesis of the compound of formula (I) represented by the compound of formula (Ic and Id) is depicted in scheme 2. The compound of formula (Ic) or (Id) can be prepared by reacting the compound of formula (6) with the compound of formula (3) or (4) to obtain the compound of formula (7) or (8). Furthermore, the compound of formula (7) and (8) (wherein X is a halogen, for example, fluorine, chlorine or bromine) can be reacted with a compound of formula (9) or with a compound of formula (10), wherein Mi is, for example, sodium or potassium, optionally in the presence of a suitable base, such as alkali metal carbonates, for example, sodium carbonate or potassium carbonate, or alkali metal hydrides such as sodium hydride or alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, in an inert solvent at temperatures ranging from about 25 °C to about 110 °C to obtain the compound of formula (Ic) or (Id). Scheme: 2 Petition 870220032852, dated 04 / 18 / 2022, p. 70 / 320 63 / 312 where R1, R3, A, G, Gi, G2, Ga, G4, Gs, E, men have the meanings described above.

[0104] Alternatively, the above reaction can also be carried out in the presence of a palladium catalyst, such as tris(dibenzylideneacetone)dipalladium(0), in the presence of a ligand, such as xanthos, in an inert solvent, for example, toluene, xylene at temperatures ranging from about 100 °C to about 150 °C, as described in Tetrahedron, 2005, 61, 5253. The compound of formula (I) wherein Y=0, m=1 (sulfoxide) and / or m=2 (sulfone), can be obtained by oxidation of the corresponding sulfite compound of formula (Ic) and (Id) during the application of appropriate oxidizing agents and conditions well known to those skilled in the art. Oxidizing agents, such as m-chloroperoxybenzoic acid (mCPBA), hydrogen peroxide / glacial acetic acid, hydrogen peroxide / trifluoroacetic acid, hydrogen peroxide / potassium permanganate, hydrogen peroxide / p-toluenesulfonylimidazole, hydrogen peroxide urea / trifluoroacetic acid, oxone, sodium periodate, Petition 870220032852, dated 04 / 18 / 2022, p. 71 / 320 64 / 312 Sodium hypochlorite and other organic peracids and the like can be used for this purpose. Examples of solvents used in this reaction include aliphatic halogenated hydrocarbons, such as dichloromethane and chloroform; alcohols, such as methanol and ethanol, and mixtures thereof.

[0105] 0 compounds of formula (I) where m=l or 2 and Y=NRYe / or Y=0, can be obtained by sulfoximination / sulfilimination of the corresponding sulfite compound of formula (Ic) and (Id) using the analogous procedure as described in Chem. Commun. , 2011,53, 2064-2061; Tetrahedron Lett. 2005, 46, 8001-8008 and document W02015071180A1.

[0106] 0 compound of formula (2) is selected from the group consisting of formulas (2a), (2b) and (2c); where R1 and R11 have the same meanings as described above.

[0107] The synthesis of compounds of formula (2a), (2b) and (2c) is described in scheme 3 to scheme 9. Scheme:3 Petition 870220032852, dated 04 / 18 / 2022, p. 72 / 320 65 / 312 where R1, R11 and n have the meanings described above.

[0108] The reaction of the compound of formula (11) with the compound of formula (12) can be carried out in an appropriate solvent at temperatures ranging from 50-200 °C to obtain the dielectrophilic compound of formula (13). Examples of solvents include, but are not limited to, N,N-dimethylformamide, dimethylacetamide, 1,4-dioxane, 1,2-dichloromethane, toluene, xylene and the like.

[0109] In the formation of pyrimidine, step-2; the pyrazole-derived compound of formula (14) can be subjected to a cyclocondensation reaction when treated with the dielectrophilic compound of formula (13) or the 1,3-diketone compound of formula (15) (e.g., 1,3-dialdehyde or 3(dialkylamino)-prop-2-enal) in the presence or absence of a base to obtain the bicyclic compound of formula (16). The preparation of a compound of formula (14) has been described in the literature (Acta Chimica Sinica 2003, 63, 855; Organic & Biomolecular Chemistry 2010, 8, 3394). Examples of bases include, but are not limited to, piperidine, morpholine, N-methylpiperazine, diethylamine, triethylamine and the like. Examples of solvents include, but are not limited to, methanol, Petition 870220032852, dated 04 / 18 / 2022, page 73 / 320 66 / 312 ethanol, isopropanol, ethylene glycol and similar substances. The reaction can be carried out at temperatures ranging from about 50 °C to about 150 °C.

[0110] When one or both electrophilic centers present in the compounds of formula (13) and (15) are shielded / hidden (e.g., hidden with an aldehyde such as a ketal), condensation can be carried out in a solvent in the presence of an acid. Examples of acids include acetic acid, sulfonic acid (e.g., PTSA), sulfuric acid, hydrochloric acid which release the reactive functional group. Examples of solvents include, but are not limited to, methanol, ethanol, isopropanol, ethylene glycol and the like. The reaction can be carried out at temperatures ranging from about 0 °C to about 150 °C. Hydrolysis of a compound of formula (16) can be achieved using a base such as sodium hydroxide, potassium hydroxide, lithium hydroxide, bis(tributyltin)oxide and the like; in solvents such as tetrahydrofuran, water, methanol, ethanol or a mixture (or mixtures) thereof, to obtain a compound of formula (2a).The reaction can be carried out at temperatures ranging from about 50 °C to about 150 °C.

[0111] Alternatively, the compound of formula (2a) can also be prepared by the following scheme 4: Scheme:4 Petition 870220032852, dated 04 / 18 / 2022, page 74 / 320 67 / 312 (2a) (23) (R' = H; ol R, R' = pinacolate)(21* where X is halogen, R1 and R11 have the meanings as described above.

[0112] The compound of formula (19) can be obtained from the compound of formula (18) in the same way described in step 1 of scheme 3. The reaction of the compound of formula (18) can be carried out in the same way described in step 2 of scheme 3. Furthermore, the compound of formula (20) can be obtained without carrying out step 3, when step 2 is carried out in the presence of acetic acid.

[0113] The conversion of the compound of formula (20) into the compound of formula (21) can be carried out in a solvent in the presence of a halogenating agent and in the presence or absence of a base. Examples of solvents include, but are not limited to, acetonitrile, chloroform, tetrahydrofuran, 1,4-dioxane, toluene, N,N-dimethylformamide and the like. Examples of halogenating agents include, but are not limited to, phosphorous oxychloride, thionyl chloride, phosphorous pentachloride, oxalyl chloride and the like. Examples of bases include, but are not limited to, N,N-dimethylaniline, Petition 870220032852, dated 18 / 04 / 2022, page 75 / 320 68 / 312 isopropylethylamine, N-methylmorpholine and similar substances. The reaction can be carried out at temperatures ranging from 50-200 °C.

[0114] The compound of formula (21) can be conventionally coupled under standard Suzuki cross-coupling conditions with boronic acids or a boronic ester compound of formula (22) to obtain the compound of formula (23). The Suzuki cross-coupling reaction can be catalyzed by a palladium-based catalyst, including but not limited to 1,1'bis(diphenylphosphino)ferrocene]dichloropalladium(II) or tetracis(triphenylphosphine)palladium(0), in a suitable solvent, for example, tetrahydrofuran (THF), N,N'-dimethylformamide (DMF), 1,2-dimethoxyethane, 1,4-dioxane or a solvent system such as a mixture of tetrahydrofuran (THF) / water, 1,2-dimethoxyethane / water, 1,4-dioxane / water or the like. The reaction is typically carried out in the presence of a base, for example, potassium carbonate, cesium carbonate, or potassium phosphate.The reaction temperature can preferably vary from room temperature (20 °C) up to the boiling point of the reaction mixture, as previously mentioned in the literature, see, for example, Chem. Soc. Rev. 2014, 43, 412-443 or document WO2014070978. The hydrolysis of a compound of formula (23) can be obtained using a base such as sodium hydroxide, potassium hydroxide, lithium hydroxide, Bis(tributyltin)oxide and the like; in solvents such as tetrahydrofuran, water, methanol, ethanol, toluene or a mixture (or mixtures) thereof, to obtain a compound of formula (2a). The reaction can be carried out at temperatures ranging from about 50 °C to 150 °C. Petition 870220032852, dated 04 / 18 / 2022, p. 76 / 320 69 / 312

[0115] The compound of formula (2aa) can be prepared according to the following scheme 5: Scheme: 5 where R1 and R11 have the same meanings as described above.

[0116] The pyrazole-derived compound of formula (14) can be subjected to cyclocondensation with 1,3-dimethyluracil compound of formula (24) or alkoxyacrylate derivatives of formula (25) in the presence of a base to obtain pyrimidin-5-one derivatives of formula (26). Examples of bases include sodium ethoxide, sodium methoxide, potassium tert-butoxide, potassium carbonate, sodium carbonate, cesium carbonate, potassium phosphate and the like. Examples of solvents include methanol, ethanol, isopropanol, ethylene glycol, N,N-dimethylacetamide, N,N-dimethylformamide and the like. The reaction can be carried out at temperatures ranging from about 50 °C to about 150 °C. Such a reaction is well known in the literature, and alternative reactions are also well described in the literature, for example J. Org. Chem200!, 72, 1046; document W02018081417.Halogenation of the compound of formula (26) with phosphorous oxychloride or phosphorous oxybromide can yield the compound of formula (28), as described in document W0201108689, for example. 0 compound. Petition 870220032852, dated 04 / 18 / 2022, page 77 / 320 70 / 312 of formula (27) can be conveniently coupled under standard Suzuki cross-coupling conditions to obtain the compound of formula (28), as described in step 5 of scheme 4. Subsequent alkaline hydrolysis of the compound of formula (28), as described in step 6 of scheme 4, can obtain the compound of formula (2aa).

[0117] A process for the synthesis of the compound of formula (2ab) is depicted in Scheme 6: Scheme: 6 where R1 and R11 have the same meanings as described above.

[0118] The protected malondialdehyde compound of formula (29) can be activated by halogenation with a halogenating agent, such as bromine, iodine or chlorine or N-bromosuccinimide, N-Iodosuccinimide or N-chlorosuccinimide under acidic conditions, which can be generated using an acid independently selected from hydrochloric acid, sulfuric acid, methanesulfonic acid, acid Petition 870220032852, dated 04 / 18 / 2022, page 78 / 320 71 / 312 trifluoroacetic acid, tetrafluoroboric acid or p-toluenesulfonic acid in a suitable solvent, for example water, to obtain a halogenated aldehyde, such as chlorine, iodine or bromomalonaldehyde of formula (30). After step 2, the compound of formula (30) can react with a pyrazole derivative of formula (14) under suitable condensation conditions to obtain a compound of formula (31). Examples of solvents include, but are not limited to, dimethyl sulfoxide, N,N-dimethylacetamide, N,N-dimethylformamide and mixtures thereof. The reaction can be carried out at temperatures ranging from about 50 °C to about 150 °C. The compound of formula (31) can also be conveniently coupled under standard Suzuki cross-coupling conditions to obtain the compound of formula (32), as described in step 5 of scheme 4. Subsequent alkaline hydrolysis of the compound of formula (32), as described in step 6 of scheme 4, can obtain the compound of formula (2ab).

[0119] Alternatively, the compound of formula (31) can also be prepared by cyclization of a pyrazole derivative of formula (14) with commercially available 2-halo-malonaldehydes of formula (33) under acid-catalyzed conditions. Examples of acids include, but are not limited to, acetic acid, sulfonic acid (e.g., PTSA), sulfuric acid, hydrochloric acid. Examples of solvents include, but are not limited to, methanol, ethanol, isopropanol, ethylene glycol, and the like. The reaction can be carried out at temperatures ranging from about 0 °C to about 150 °C. The pyrazolo[1,5-a]pyrimidine derivative of formula (32) can also be prepared following cyclocondensation of the pyrazole derivative of formula (14) or with malonaldehyde. Petition 870220032852, dated 04 / 18 / 2022, page 79 / 320 72 / 312 commercially available (34) or its equivalent (35). The derivative (35) can be prepared by the methods described in J.Het.Chem. 1974, 44, 51.

[0120] A process for the synthesis of the compound of formula (2b) is depicted in Scheme 7: Scheme: 7 X = Halogen where R11 and n have the meanings described above.

[0121] The compound of formula (38) can be prepared in a two-step procedure from 2-aminopyridine derivatives of formula (36) wherein the first step involves the condensation reaction of 2-aminopyridine derivatives of formula (36) with haloacetic acid (37) under basic conditions in a suitable solvent. Examples of suitable bases include, but are not limited to, tertiary amines such as trimethylamine and diisopropylethylamine. Examples of suitable solvents include, but are not limited to, water, methanol, ethanol, isopropanol and mixtures thereof. The reaction can be carried out at temperatures ranging from about 50 °C to about 150 °C.

[0122] Intramolecular cyclization of the compound of formula (38) in the presence of phosphorous oxychloride or phosphorous oxybromide at elevated temperatures in a suitable solvent (e.g., toluene) can provide 2haloimidazol[1,2-a]pyridine analogs of formula (39). Alkoxycarbonylation of the compound of formula (38) using alkyl chlorocarbonate of formula (40) as a source of Petition 870220032852, dated 04 / 18 / 2022, p. 80 / 320 73 / 312 carbon can be carried out using organometallic reagents, such as n-butyl lithium and the like, in etheric solvents, such as tetrahydrofuran, diethyl ether, tert-butyl methyl ether and the like to obtain compound of formula (41). The reaction can be carried out at temperatures ranging from about -78 °C to approximately 25 °C (document WO2011163355). Subsequent alkaline hydrolysis of compound of formula (41), as described in step 6 of scheme 4, can yield compound of formula (2b).

[0123] A process for the synthesis of the compound of formula (2c) is depicted in Scheme 8: Scheme: 8 where R2, R11 and n have the meanings described above.

[0124] The compound of formula (44) can be prepared by reacting the substituted pyridine compound of formula (42) with alkyl 2-haloacetate of formula (43) in an inert solvent including, but not limited to, ethyl acetate, acetone, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, dichloroform, chloroform, N,N-dimethylformamide, toluene, xylene, methanol, ethanol, a mixture thereof, and similar bases such as trimethylamine, pyridine, N,N-diisopropyl ethylamine, 2,6-lutidine can be used in the reaction. The reaction can be carried out at temperatures ranging from 0 °C to reflux temperature, and the time of Petition 870220032852, dated 04 / 18 / 2022, page 81 / 320 74 / 312 The reaction typically takes between 30 minutes and 48 hours and varies based on the starting material, solvent used, reaction temperature, or similar factors.

[0125] Indolizine derivatives of formula (46) can be prepared by reacting the compound of formula (44) with halo alkenyl tosylates of formula (45). The preparation of a compound of formula (45) has been described in the literature (Tetrahedron 2018, 74, 5295; Organic Letters 2010, 12, 5518). As an inert solvent, ethyl acetate, acetone, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, dichloroform, chloroform, N,N-dimethylformamide, toluene, xylene, methanol, ethanol, or a mixture thereof may be used in the reaction. As a base, potassium carbonate, sodium carbonate, cesium carbonate, sodium hydroxide, potassium fluoride, lithium hydroxide, trimethylamine, pyridine, N,N-diisopropyl ethylamine, and 2,6-lutidine may be used in the reaction. The reaction can be carried out at temperatures ranging from 0 °C to reflux temperature. The reaction time is typically from one hour to 48 hours and varies based on the starting material, solvent used, and reaction temperature or similar factors. This reaction is known in the literature and is well described, for example, in Tetrahedron 2004, 60, 5487.

[0126] Subsequent alkaline hydrolysis of the compound of formula (46), as described in step 6 of scheme 4, can yield the compound of formula (2c).

[0127] A process for the synthesis of the compound of formula (2ca) is depicted in Scheme 9: Scheme: 9 Petition 870220032852, dated 04 / 18 / 2022, p. 82 / 320 75 / 312 X = Halogen R = Lower alkyl (2ca) <5°) where R1, R2, R11 and n have the meanings described above.

[0128] Indolizine derivatives of formula (47) can be prepared by reacting the compound of formula (44) with halo alkenyl tosylates of formula (45a) following step 2, as described in scheme 8. The compound of formula (47) can be reacted with the compound of formula (9) or with a compound of formula (10) followed by oxidation to obtain the compound of formula (48). The compound of formula (49) can be prepared from the compound of formula (48) by halogenation with a halogenating agent, such as N-bromosuccinimide. N-chlorosuccinimide, N-iodosuccinimide. The reaction can be carried out in an inert solvent selected from dichloromethane, 2-dichloromethane, chloroform, carbon tetrachloride, acetic acid, acetonitrile, methanol, N,N-dimethylformamide and the like, or a mixture thereof. The reaction can be carried out at temperatures ranging from 0 °C to reflux temperature. Reaction time Petition 870220032852, dated 04 / 18 / 2022, page 83 / 320 76 / 312 typically takes 30 minutes to 48 hours and varies based on the starting material, solvent used, and reaction temperature.

[0129] The compound of formula (49) can be conveniently coupled under standard Suzuki cross-coupling conditions to obtain the compound of formula (50), as described in step 5 of scheme 4. Subsequent alkaline hydrolysis of the compound of formula (50), as described in step 6 of scheme 4, can obtain the compound of formula (2ca).

[0130] The subgroup of the compound of formula (I), where Q is Qa and Gs is CR3; R = H can be represented by the compound of formula (52) and can be prepared by reacting the compound of formula (6b) with the compound of formula (51) to obtain the compound of formula (52), where Gs is CR3, R3 = H, Scheme: 10 where R3, R7, A, G, Gi, G2, G4, Gs, and En have the meanings described above.

[0131] Cyclization to obtain compound of formula (52) can be carried out in the presence of a Lewis acid, such as indium (III) triflate or zinc (II) iodide, in solvents such as 1,2-dichlorobenzene, chlorobenzene, in the presence of catalytic copper (II) salts, such as copper (II) acetate, under an oxygen or air atmosphere. The reaction can be carried out at temperatures ranging from about 100 °C to about 180 °C. This reaction is described earlier in Petition 870220032852, dated 04 / 18 / 2022, p. 84 / 320 77 / 312 literature; see, for example, (Adv. Synth. Catalysis, 2013, 355, 1741; J.Org.Chem, 2013, 78, 12494). The synthesis of the compound of formula (51) was described in document WO2015000715.

[0132] The compound of formula (52) can be reacted with a compound of formula (9) or with a compound of formula (10) to obtain the compound of formula (53).

[0133] The compound of formula (53A) can be prepared according to the synthesis process, as described in Chem. Commun., 2017,53, 2064-2067; Tetrahedron Lett. 2005, 46, 8007-8008 and document WO2015071180A1. Scheme: 11 where R1, R3, A, G, G1, G2, G4, G5, E, and men have the meanings described above.

[0134] The compound, represented by formula (54) where m=1 (sulfoxide) and / or m=2 (sulfone), can be obtained by oxidation of the corresponding sulfite compound of formula (53) during the application of appropriate oxidation agents and conditions well known to those skilled in the art. Oxidizing agents, such as m-chloroperoxybenzoic acid (mCPBA), hydrogen peroxide / glacial acetic acid, hydrogen peroxide / trifluoroacetic acid, peroxide Petition 870220032852, dated 04 / 18 / 2022, page 85 / 320 78 / 312 Hydrogen / potassium permanganate, hydrogen peroxide / ptoulenesulfonylimidazole, hydrogen peroxide, urea / trifluoroacetic acid, oxone, sodium periodate, sodium hypochlorite, and other organic peracids and the like, can be used for oxidation. Examples of solvents used in this reaction include aliphatic halogenated hydrocarbons, such as dichloromethane and chloroform; alcohols, such as methanol and ethanol, and mixtures thereof.

[0135] Halogenation of the compound of formula (54) where Gs = CR3; R3 = H, with a halogenating agent such as N-chlorosuccinamide, N-bromorosuccinamide, Niodorosuccinamide, in a polar aprotic solvent, such as acetonitrile or N,N-dimethylformamide, at room temperature, can give rise to compounds of formula (Ici), Scheme: 12 (IC / ) X = halogen where R1, R3, A, G, Gi, Gs, G4, Gs, E, men have the meanings described above.

[0136] The compounds of formula (Ici) can be reacted with the compounds R3-B(OR''')2 (R'''= H or R''' = pinacolate); in the presence of a palladium catalyst to generate compounds of formula (Ic), where Gs = CR3; R3= alkyl, cycloalkyl, aryl, heteroaryl. Such Suzuki reactions are well described previously in the literature, see, for example, document WO2012133607.

[0137] 0 process for the synthesis of the compound of the formula Petition 870220032852, dated 04 / 18 / 2022, p. 86 / 320 79 / 312 (6b) is depicted in diagram 12a: Scheme: 12a <6> X = Halogen,(55)where G, E and A have the meanings as described above.

[0138] Carboxylic acid of formula (6) can be converted into amide of formula Weinreb (55) by reaction with N, O-Dimethyl-hydroxylamine by methods known to those skilled in the art in a manner analogous to the procedures described in documents WO201175643 and EP2671582. Subsequent treatment of the Weinreb amide of formula (55) with Grignard reagents of formula (R7CH2MgHal), according to the method described in Tetrahedron Letters 1981, 22, 3815 can yield compound of formula (6b).

[0139] The process for the synthesis of the compound of formula (Id) is depicted in Scheme 13, where Q is Q4 and Gs is nitrogen, G4 is CR3, then the compound of formula (Id) can be prepared by reacting the compound of formula (56) with a compound of formula (57), optionally, in the presence of a suitable base in an inert solvent. Alternatively, when G4 is nitrogen, the compound of formula (Id) can be prepared by reacting a compound of formula (58), in which X“ is a mesityl halide or sulfonate ion, with a compound of formula (59), optionally, in the presence of a suitable base in an inert solvent. Scheme: 13 Petition 870220032852, dated 04 / 18 / 2022, p. 87 / 320 80 / 312 R1 X = halogen where R1, R3, A, G, Gi, Gs, G4, Gs, E, men have the meanings described above.

[0140] The synthesis of the compound of formula (56) was described in the literature in document W02015000715. The synthesis of the compound of formula (57) can be obtained, for example, in a manner analogous to document EP1371638. The compound of formula (58) can be prepared by N-amination by reacting the compound of formula (56) with O-mesitylenesulfonylhydroxylamine (MSH) as an amination reagent or one of its equivalents, as described, for example, in J.Heterocyclic Chem. 1975, 12, 107 and Synthesis 1977, 1, 17.

[0141] 0 subgroup of compounds of formula (I), where Q is Qs and Gs is CR3, can be represented by compounds of formula (1e). 0 compound of formula (1e) can be synthesized by reacting compound of formula (60) with a compound of formula (6b) in a manner analogous to the preparation of compound of formula (1c). Scheme: 14 Petition 870220032852, dated 04 / 18 / 2022, p. 88 / 320 81 / 312 (60) R7= H where R1, R3, A, G, Gi, Gs, Gs, E, and men have the meanings described above.

[0142] Those skilled in the art will recognize that the compound of formula (If), where Q is Qe and G5 is CR3, can be prepared in a similar manner by reacting the compound of formula (61) with the compound of formula (57a) or (6a). Scheme: 15 X = outgoing group R7 = H where R1, R3, A, G, Gi, G2, Gs, E, men have the meanings described above.

[0143] 0 subgroup of the compound of formula (I), where Q is Qs and Gs is nitrogen, can be represented by the compound of formula (Ig), can be prepared by reacting a compound of formula (62) with the compound of formula (59), optionally, in the presence of a suitable base in an inert solvent. Scheme: 16 Petition 870220032852, dated 04 / 18 / 2022, p. 89 / 320 82 / 312 (63) OR (62) (lh) where R1, R3, A, G, Gi, Gg, Gs, E, men have the meanings described above.

[0144] The compound of formula (62) can be prepared by N-amination by reacting the compound of formula (51) with O-mesitylenesulfonylhydroxylamine (MSH) as an amination reagent or one of its equivalents, as described, for example, in J. Heterocyclic Chem. 1975, 12, 107 and Synthesis 1977, 1, 17. The subgroup of the compound of formula (I), where Q is Qs and Gs is nitrogen, can be represented by the compound of formula (Ih), can be prepared by reacting a compound of formula (63) with the compound of formula (59), optionally, in the presence of a suitable base in an inert solvent.

[0145] The compound of formula (63) can be prepared by N-amination by reacting the compound of formula (60) with O-mesitylenesulfonylhydroxylamine (MSH) as an amination reagent; the process is described in J.Heterocyclic Chem. 1975, 12, 107 and Synthesis 1977, 1, 17. The synthesis of the compound of formula (60) was described in the literature in document WO2007113558. Petition 870220032852, dated 04 / 18 / 2022, pp. 90 / 320 83 / 312 (60) (63) where R3, Gi and G2 have the meanings described above.

[0146] In a further embodiment, Q is Q? and involves the reaction of the compound of formula (64) with the compound of formula (65) to obtain the compound of formula (li) where Gs is CR3 or N. The process is summarized in scheme 17 for the compound of formula (li): Scheme: 17 where R1, R3, G, A, Gi, G2, G5, Ge, E, men have the meanings as described above.

[0147] 0 compound of formula (65) is commercially available or can be prepared by methods known on their own or in a manner analogous to that described in documents WO2017113558 and WO2011090122.

[0148] In Scheme 17, the N-substituted amidines of formula (66) can be prepared by reacting the compound of formula (64) with the compound of formula (65) in the presence of a suitable base. Examples of suitable bases are alkali metal hydrides, such as sodium hydride, alkali metal salts of hexamethyldisilazane, such as sodium hexamethyldisilazane, allo-holates, such as potassium or sodium tert-butoxides or lithium diisopropylamide. The reaction can be Petition 870220032852, dated 04 / 18 / 2022, p. 91 / 320 84 / 312 carried out in solvents, preferably inert under the prevailing reaction conditions, for example, ethereal solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, diisopropyl ether, 1,2-dimethoxyethane, tert-butylmethyl ether; nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene, xylene; polar aprotic solvents such as N,N-dimethylformamide, N-methylpyrrolidine or dimethyl sulfoxide. The reaction can be carried out at temperatures ranging from about 0 °C to about 150 °C. Such a reaction is described previously in the literature; see, for example, J.Am.Chem.Soc. 2009, 131, 15080.

[0149] The intramolecular oxidative cyclization of N-substituted amidines of formula (66) in the presence or absence of a suitable base can be carried out in a manner analogous to that described in J.Org.Chem 2015, 80, 7219; J.Org. Chem 2014, 79, 4687. Examples of oxidants include sodium hypochlorite, lead(IV) acetate, manganese dioxide, iodine, hypervalent iodine(III) reagents such as phenyliodine(III) diacetate (PIDA) and phenyliodine(III) bis(trifluoroacetate) (PIFA). The reaction can be carried out in solvents, preferably, that are inert under the prevailing reaction conditions, for example, nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; Polar aprotic solvents, such as N,N-dimethylformamide, N-methylpyrrolidine, or dimethyl sulfoxide or ethyl acetate; halogenated hydrocarbons, such as dichloromethane or dichloroethane; alcoholic solvents, such as hexafluoroisopropanol, methanol, ethanol, trifluoroethanol, isopropanol.Suitable bases include... Petition 870220032852, dated 04 / 18 / 2022, p. 92 / 320 85 / 312 potassium carbonate, sodium carbonate, and cesium carbonate. The reaction can be carried out at temperatures ranging from about 25 °C to about 180 °C.

[0150] Alternatively, the compound of formula (li) can be synthesized after step 3 in a single step involving transition metal-catalyzed oxidative coupling of the compound of formula (65) with the compound of formula (64) in a manner analogous to that described in WO201341472 and J.Am.Chem.Soc. 2009, 131, 15080. The transition metal catalyst includes zinc or copper salts, such as copper(I) bromide, copper(I) chloride, copper(I) iodide, copper(II) acetate, zinc chloride, zinc(II) bromide, zinc iodide. Suitable bases include, for example, 1,10-phenanthroline, cesium carbonate, sodium carbonate, potassium carbonate. The reaction can be carried out in solvents, preferably those that are inert under the prevailing reaction conditions, for example, aromatic hydrocarbons such as 1,2-dichlorobenzene, toluene or xylene. The reaction can be carried out at temperatures ranging from 50 °C to 150 °C.

[0151] The compound of formula (64) is selected from the group consisting of formulas (64a), (64b) and (64c) (64a) (64b) (64c) X = Halogen, -S(O)„Ri n = 0-2 where R11 and n have the meanings described above. Petition 870220032852, dated 04 / 18 / 2022, p. 93 / 320 86 / 312

[0152] The synthesis of compounds of formula (64a), (64b) and (64c) is described in Scheme 18 and Scheme 19. Scheme: 18 (13} (64a) where B^B11e m have the meanings described above.

[0153] In the pyridine formation step, the pyrazole derivative of formula (67) can be subjected to cyclocondensation reaction when treated with a dielectrophilic compound of formula (13) or a 1,3-diketone of formula (15) (e.g., a 1,3-dialdehyde or 3-(dialkylamino)-prop-2-enal) following a similar procedure as described in Scheme 3 to obtain a compound of formula (64a). The preparation of a compound of formula (67) has been described in the literature (Journal of Heterocyclic Chemistry 2016, 53, 1231). Scheme: 19 Petition 870220032852, dated 04 / 18 / 2022, p. 94 / 320 87 / 312 R = Lower alkyl group, X = Halogenic group, where R11 and n have the meanings described above.

[0154] The compound of formula (68) can be prepared from the compound of formula (41) in a manner analogous to the method described in documents WO201065760 and WO2016133838 using an ammonia source. Ammonium hydroxide solution or methanolic ammonia is normally used as an ammonia source. The synthesis of the compound of formula (41) was described in Scheme 7. The reaction can be carried out under prevailing reaction conditions employing ethereal solvents such as 1,4-dioxane or tetrahydrofuran or alcoholic solvents such as methanol, ethanol and the like at temperatures ranging from about 25 °C to about 100 °C. The compound of formula (64b) can be prepared in a manner analogous to the method described in documents W0201065760 and EP2740730 by reacting the compound of formula (68) with dehydration reagents such as, but not limited to, phosphoryl chloride or trifluoroacetic anhydride.The reaction can be carried out under prevailing reaction conditions employing ethereal solvents such as 1,4-dioxane or tetrahydrofuran at temperatures ranging from about 25 °C to about 120 °C.

[0155] The compound of formula (64c) can be prepared starting from the compound of formula (46) following the reaction sequence and similar conditions as described for a. Petition 870220032852, dated 04 / 18 / 2022, p. 95 / 320 88 / 312 preparation of the compound of formula (64b), as described in scheme 19. The general synthesis of the compound of formula (46) was described in scheme 8.

[0156] In one embodiment, Q is Qs and involves the reaction of the compound of formula (2) or of formula (59) or formula (69) with the compound of formula (70) to obtain the compound of formula (Ij) wherein G4 and Gs is N. Scheme 2 describes a method for preparing the compound of formula (Ij). Scheme: 20 (71) where R1, R3, A, Z, G, Gi, G2, E, men have the meanings as described above.

[0157] A halo derivative of compound of formula (71) can be obtained commercially or can be prepared by methods known in the literature or by other methods known to those skilled in the art. The reaction of a compound of formula (71) with hydrazine can be carried out using reaction conditions known to those skilled in the art (e.g., Larock, RC Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Ed., 1999, Wiley-VCH). An intermediate compound of Petition 870220032852, dated 04 / 18 / 2022, p. 96 / 320 89 / 312 formula (70) in step 2 can react with an acid of the compound of formula (2) using an appropriate set of amide coupling reagents such as N-methylmorpholine / isobutyl chloroformate, 1-ethyl-3-(3-dimethylaminopropyl)carbodi-imide / hydroxybenzotriazole or other reagents described in The Practice of Peptide Synthesis, 2nd Edition, Spring-Verlag, Bodanszy, Miklos (1993) can provide intermediate hydrazides of formula (71). In addition, acyl hydrazides of formula (71) can also be prepared following the reaction of a compound of formula (70) and an acid chloride of formula (59) in the presence of an appropriate base, such as N,N-diisopropylethylamine or triethylamine.The formation of the triazole compound of formula (Ij) can be obtained after cyclodehydration of the compound of formula (71) using phosphorous oxychloride / phosphorous pentachloride, Lawesson's reagent, acetic acid or polyphosphoric acid at an elevated temperature or under conventional procedure or under microwave irradiation. Alternatively, the transformation can also be obtained after reacting the compound of formula (71) with triphenylphosphine dichloride or P(alkyl)3 / carbon tetrachloride in the presence of a base, such as triethylamine or N,N-diisopropylethylamine or other methods known to those skilled in the art. As an alternative approach, hydrazones of formula (72) can be prepared following step 4 by reacting the compound of formula (70) with the aldehyde compound of formula (69) by other methods known to those skilled in the art or by methods known in the literature (e.g., Larock, RC Comprehensive Organic Transformations: A Guide to Functional Group). Petition 870220032852, dated 04 / 18 / 2022, page 97 / 320 90 / 312 Preparations, 2nd Ed., 1999, Wiley-VCH). Furthermore, following step 5, the compound of formula (Ij) can also be prepared by oxidative cyclization of hydrazones of formula (72) using oxidants such as diacetoxy iodobenzene, N-bromosuccinimide, chloramine T, ceric ammonium nitrate, trichlorocyanuric acid and copper(II) chloride.

[0158] The compound of formula (69) is selected from the group consisting of formulas (69a), (69b) and (69c) (69a) (69b) (69c) n = 0-2 ; X = Halogen, -S(O)nRq where R1, R11 and n have the meanings described above.

[0159] The compound of formula (69a-c) can be prepared by partial reduction of the compounds of formula (23), (41) and (46) by methods known in the literature (e.g., Larock, RC Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Edition, 1999, WileyVCH).

[0160] The process for preparing compound of formula (I) where Q is Qg involves the reaction of compound of formula (6b) with compound of formula (73) to obtain compound of formula (74), where Ga is CR3; R3 = H. Subsequently, compound of formula (1k) can be obtained from compound of formula (74) by following the set of general reactions as described for the synthesis of compound (1c) in Scheme 1. A Petition 870220032852, dated 04 / 18 / 2022, p. 98 / 320 91 / 312 synthesis of the compound of formula (73) was described in document W02018206479. Scheme: 21 where R1, R3, R6, A, G, Gi, G2, G3, Z, E, men have the meanings as described above.

[0161] The process for preparing the compound of formula (I) where Q is Q10 involves the reaction of the compound of formula (2) with the compound of formula (75) to obtain the compound of formula (76), where Ga is = NR6. Subsequently, the compound of formula (11) can be obtained from the compound of formula (76) following the set of general reactions as described in Scheme 1. The synthesis of the compound of formula (75) was described in document WO2017084879. Scheme: 22 where X is halogen, R1, R3, R6, R', A, Z, Gi, Ga, E, men have the meanings described above.

[0162] The process for preparing the compound of formula (I) represented by the compound of formula (IB) occurs by sulfilimation / sulfoximination of the compound of formula (IA) where n=0, as described in Chem. Commun., 2017, 53, 2064-2067; Tetrahedron Lett. 2005, 46, 8007-8008 and W02015071180A1 Petition 870220032852, dated 04 / 18 / 2022, p. 99 / 320 92 / 312 Scheme: 23 where Q, R1, RY, A, G, E and en have the meanings described above.

[0163] In one embodiment, the present invention provides a composition for controlling or preventing invertebrate pests. The composition comprises a biologically effective amount of the compound of formula(I) and at least one additional component selected from the group consisting of surfactants and auxiliaries.

[0164] In yet another embodiment, the present invention provides a compound of formula (I) or its N-oxides and salts in routine types of agrochemical compositions, for example, solutions, emulsions, suspensions, powders, pastes, granules, pressed products, capsules and mixtures thereof. Examples of composition types include suspensions (e.g., SC, OD, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), wettable pastes, tablets, powders or dusts (e.g., WP, SP, WS, DP, DS), pressed products (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticidal articles (e.g., LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g., GF). These and other composition types are defined in the Catalogue of pesticide formulation types and international coding system, Technical Monograph No. 2, 6a. Petition 870220032852, dated 04 / 18 / 2022, pp. 100 / 320 93 / 312 Edition. May 2008, CropLife International.

[0165] The compositions are prepared in a known manner, as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, Germany, 2001; or by Knowles, New developments in crop protection product formulation, Agrow Reports DS243, TandF Informa, London, 2005.

[0166] Examples of suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, antifoaming agents, colorants, tackifying agents or binders.

[0167] Suitable solvents and liquid carriers are water and organic solvents, such as fractions of mineral oil with medium to high boiling points, for example, kerosene, diesel oil; vegetable or animal oils; aliphatic, cyclic and aromatic hydrocarbons, for example, toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, for example, ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, for example, cyclohexanone; esters, for example, lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, for example, N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

[0168] Suitable carriers or solid loads are Petition 870220032852, dated 04 / 18 / 2022, pp. 101 / 320 94 / 312 mineral earths, for example, silicates, silica gel, talc, kaolin, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, for example, cellulose, starch; fertilizers, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, for example, cereal flour, tree bark flour, wood flour, walnut shell flour and mixtures thereof.

[0169] Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes and mixtures thereof. Such surfactants may be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids or adjuvants. Examples of surfactants are listed in McCutcheon, Volume 1: Emulsifiers and Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Edition or North American Edition).

[0170] Suitable anionic surfactants are alkaline, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, fatty acid and oil sulfonates, ethoxylated alkylphenol sulfonates, alkoxylated arylphenol sulfonates, condensed naphthalene sulfonates, dodecyl and tridecylbenzene sulfonates, naphthalene and alkylnaphthalene sulfonates, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of Petition 870220032852, dated 04 / 18 / 2022, page 102 / 320 95 / 312 fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and ethoxylates of carboxylated alcohol or alkylphenol.

[0171] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amide oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters that have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide may be used for alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters, or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose, and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homeopolymers or copolymers of vinylpyrrolidone, vinyl alcohols, or vinyl acetate.

[0172] Suitable cationic surfactants are quaternary surfactants, for example, quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetaines and imidazolines. Suitable block polymers are AB or ABA type block polymers comprising polyethylene oxide and polypropylene oxide blocks, or ABC type block polymers comprising alkanol, oxide Petition 870220032852, dated 04 / 18 / 2022, page 103 / 320 96 / 312 polyethylene and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkaline salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.

[0173] Suitable adjuvants are compounds that, by themselves, have negligible or no pesticidal activity and that enhance the biological performance of compound I on the target. Examples include surfactants, mineral or vegetable oils, and other auxiliaries. Examples are listed by Knowles, Adjuvants and Additives, Agrow Reports DS256, T and F Informa UK, 2006, chapter 5.

[0174] Suitable thickeners are polysaccharides (e.g., xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates. Suitable bactericides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones. Suitable antifreeze agents are ethylene glycol, propylene glycol, urea, and glycerin. Suitable antifoaming agents are silicones, long-chain alcohols, and fatty acid salts. Suitable colorants (e.g., red, blue, or green) are pigments with low water solubility and water-soluble dyes. Examples include inorganic colorants (e.g., iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (e.g., alizarin, azo, and phthalocyanine dyes). Suitable tackifying agents or binders are polyvinylpyrrolidone, polyvinyl acetates, polyvinyl alcohols, polyacrylates, synthetic waxes or Petition 870220032852, dated 04 / 18 / 2022, page 104 / 320 97 / 312 biological and cellulose ethers.

[0175] Examples of types of composition and their preparation are: i) Water-soluble concentrates (SL, LS)

[0176] 10-60% by weight of a compound I or an N-oxide or salt thereof and 5-15% by weight of a wetting agent (e.g., alcohol alkoxylates) are dissolved in water and / or in a water-soluble solvent (e.g., alcohols) up to 100% by weight. The active substance dissolves upon dilution with water. ii) Dispersible concentrates (DC)

[0177] 5-25 wt% of a compound I or an N-oxide or salt thereof and 1-10 wt% of dispersant (e.g., polyvinylpyrrolidone) are dissolved in up to 100 wt% of organic solvent (e.g., cyclohexanone). Dilution with water generates a dispersion. iii) Emulsifiable concentrates (EC)

[0178] 15-70 % by weight of a compound I or an N-oxide or salt thereof and 5-10 % by weight of emulsifiers (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in up to 100 % by weight of water-soluble organic solvent (e.g., aromatic hydrocarbon). Dilution with water generates an emulsion. iv) Emulsions (EW, EO, ES)

[0179] 5-40% by weight of a compound I or an N-oxide or salt thereof and 1-10% by weight of emulsifiers (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40% by weight of water-insoluble organic solvent (e.g., aromatic hydrocarbon). This mixture is introduced up to 100% by weight Petition 870220032852, dated 04 / 18 / 2022, page 105 / 320 98 / 312 of water is processed through an emulsifying machine and becomes a homogeneous emulsion. Dilution with water creates an emulsion. v) Suspensions (SC, OD, FS)

[0180] In a stirred ball mill, 20-60% by weight of a compound I or an N-oxide or salt thereof are ground with the addition of 2-10% by weight of dispersants and wetting agents (e.g., sodium lignosulfonate and alcohol ethoxylate), 0.1-2% by weight of thickener (e.g., xanthan gum) and up to 100% by weight of water to generate a fine suspension of the active substance. Dilution with water generates a stable suspension of the active substance. For FS-type compositions, up to 40% by weight of binder (e.g., polyvinyl alcohol) is added. vi) Water-dispersible granules and water-soluble granules (WG, SG)

[0181] 50-80% by weight of a compound I or an N-oxide or salt thereof are ground to fine granulation with the addition of up to 100% by weight of dispersants and wetting agents (e.g., sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical apparatus (e.g., extrusion, spray tower, fluidized bed). Dilution with water generates a stable dispersion or solution of the active substance. vii) water-dispersible powders and water-soluble powders (WP, SP, WS)

[0182] 50-80% by weight of a compound I or an N-oxide or salt thereof are milled in a rotor-stator milling machine with the addition of 1-5% by weight of dispersants (e.g., sodium lignosulfonate), 1-3% by weight of agents Petition 870220032852, dated 04 / 18 / 2022, page 106 / 320 99 / 312 wetting agents (e.g., alcohol ethoxylate) and up to 100% by weight of solid carrier, e.g., silica gel. Dilution with water generates a stable dispersion or solution of the active substance. viii) Gel (GW, GF)

[0183] In a stirred ball mill, 5-25 wt% of a compound I or an N-oxide or salt thereof are ground with the addition of 3-10 wt% of dispersants (e.g., sodium lignosulfonate), 1-5 wt% of thickener (e.g., carboxymethylcellulose) and up to 100 wt% water to generate a fine suspension of the active substance. Dilution with water generates a stable suspension of the substance. iv) 5-20 wt% of microemulsion (ME) of a compound I or an N-oxide or salt thereof are added to 5-30 wt% of organic solvent (e.g., fatty acid dimethylamide and cyclohexanone), 10-25 wt% of surfactant mixture (e.g., alcohol ethoxylate and arylphenol ethoxylate) and water up to 100%. This mixture is stirred for 1 hour to spontaneously produce a thermodynamically stable microemulsion. iv) Microcapsules (SC)

[0184] An oil phase comprising 5-50 wt% of a compound I or an N-oxide or salt thereof, 0-40 wt% of water-insoluble organic solvent (e.g., aromatic hydrocarbon), 2-15 wt% of acrylic members (e.g., methyl methacrylate, methacrylic acid and a di- or triacrylate) are dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(acrylate) microcapsules Petition 870220032852, dated 04 / 18 / 2022, page 107 / 320 100 / 312 methyl). Alternatively, an oil phase comprising 5-50% by weight of a compound I, according to the present invention, 0-40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon) and an isocyanate monomer (e.g., diphenylmethylene-4,4'-diisocyanate) are dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). The addition of a polyamine (e.g., hexamethylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1-10% by weight. The % by weight refers to the total composition of CS, ix) Dustable powders (DP, DS) 1-10% by weight of a compound I or an N-oxide or salt thereof are ground to fine granulation and thoroughly mixed with up to 100% by weight of solid carrier, for example, precisely divided kaolin. x) Granules (GR, FG) 0.5-30% by weight of a compound I or an N-oxide or its salt is ground to a fine granulation and combined with up to 100% by weight of solid carrier (e.g., silicate). Granulation is achieved by extrusion, spray drying, or fluidized bed drying. xi) 1-50 % by weight of ultra-low volume (UL) liquids of a compound I or an N-oxide or salt thereof are dissolved in up to 100 % by weight of organic solvent, for example, aromatic hydrocarbon.

[0185] Composition types i) to xi) may optionally include additional auxiliaries, such as 0.1-1% by weight bactericides, 5-15% by weight antifreeze agents, 0.11% by weight antifoaming agents and 0.1-1% by weight colorants.

[0186] In another embodiment, the present invention provides Petition 870220032852, dated 04 / 18 / 2022, page 108 / 320 101 / 312 agrochemical composition compounds of formula (I) comprising active substance between 0.01 and 95% by weight, preferably between 0.1 and 90%, and more preferably between 1 and 70%, in particular between 10 and 60% by weight of the active substance. The active substances are employed in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

[0187] Water-soluble concentrates (LS), suspoemulsions (SE), flowable concentrates (FS), dry treatment powders (DS), water-dispersible powders for fluid paste treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are commonly used for the treatment of plant propagation materials, specifically seeds. The compositions in question provide, after dilution two to ten times, concentrations of the active substance of 0.01 to 60% by weight, preferably 0.1 to 40% by weight, in ready-to-use preparations. Application can be made before or during sowing.

[0188] Methods for applying or treating compound I and compositions thereof, respectively, to plant propagation material, especially seeds, include methods of film coating, coating, pelleting, dusting, soaking, and in-furrow application to the propagation material. Preferably, compound I or compositions thereof, respectively, are applied to the plant propagation material by a method such that germination is not induced, for example, by film coating, pelleting, coating, and seed dusting.

[0189] When used for plant protection, the Petition 870220032852, dated April 18, 2022, pp. 109-320 102 / 312 The quantities of active substances applied are, depending on the type of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, in particular from 0.1 to 0.75 kg per ha.

[0190] In the treatment of plant propagation materials such as seeds, for example, by dusting, coating or soaking seeds, quantities of active substance of 0.1 to 1000 g, preferably 1 to 500 g, more preferably 1 to 100 g, most preferably 5 to 100 g, per 100 kilogram of plant propagation material (preferably seed) are generally required.

[0191] When used for the protection of stored materials or products, the amount of active ingredient applied depends on the type of application area and the desired effect. The amounts usually applied for the protection of materials are 0.001 to 2 kg, preferably 0.005 to 1 kg, of active substance per cubic meter of treated material.

[0192] Various types of oils, wetting agents, adjuvants, fertilizer, or micronutrients and other pesticides (e.g., herbicides, insecticides, fungicides, growth regulators, protectants) may be added to the active substances or to compositions comprising them as a premix or, if appropriate, not until immediately before use (tank mixing). These agents may be mixed by addition with the compositions according to the present invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0193] The user can apply the composition according to Petition 870220032852, dated 04 / 18 / 2022, page 110 / 320 103 / 312 The present invention typically involves a pre-dosing device, a hand-held sprinkler, a spray tank, a sprinkler plane, or an irrigation system. Typically, the agrochemical composition consists of water, buffer, and / or additional auxiliaries at the desired application concentration, and the ready-to-use spray liquor or the agrochemical composition according to the present invention is then obtained. Typically, 20 to 6000 liters, preferably 35 to 1000 liters, more preferably 50 to 500 liters, of the ready-to-use spray liquor are applied per hectare of usable agricultural area.

[0194] According to one embodiment, individual components of the composition according to the present invention, as parts of a kit or parts of a binary or tertiary mixture, can be mixed by the user himself in a spray tank and additional auxiliaries can be added, if appropriate.

[0195] The compounds and compositions of the present invention are therefore useful agronomically for protecting crops in the field against phytophagous invertebrate pests and also non-agronomically for protecting other horticultural crops and plants against phytophagous invertebrate pests. This utility includes protecting crops and other plants (i.e., both agronomic and non-agronomic) that contain genetic material introduced by genetic engineering (i.e., transgenic) or modified by mutagenesis to provide advantageous traits.

[0196] The compounds of the present invention are characterized by favorable soil and / or metabolic residual patterns and exhibit activity that controls a Petition 870220032852, dated 04 / 18 / 2022, page 111 / 320 104 / 312 spectrum of agronomic or non-agronomic invertebrate pests. The compounds of the present invention are active ingredients of preventive and / or curative value in the field of pest control, even at low application rates, which can be used against insect-resistant pests such as insects and mites and are well tolerated by warm-blooded species, fish and plants.

[0197] In the context of the present invention, invertebrate pest control means inhibition of invertebrate pest development (including mortality) that causes a significant reduction in feeding or other injury or damage caused by the pest; (related expressions are defined analogously.) As stated in the present invention, the term invertebrate pest includes arthropods, gastropods, and nematodes of economic importance as pests. The term arthropod includes insects, mites, spiders, scorpions, centipedes, millipedes, woodlice, and symphylans.

[0198] The term gastropod includes snails, slugs, and other Stylommatophora. The term nematode includes all helminths, such as: intestinal roundworms, heartworms, and phytophagous nematodes (Nematoda), parasitic nematodes (Tematoda), Acanthocephala, and tapeworms (Cestoda). Experts in the field will recognize that not all compounds are equally effective against all pests.

[0199] The compounds of the present invention exhibit activity against agronomic pests in forests, greenhouses, nurseries, ornamental plants, lawns, food and fibers, public and animal health, commercial and domestic structure pests, residential pests, and stored products. These Petition 870220032852, dated 04 / 18 / 2022, page 112 / 320 105 / 312 include larvae of the order Lepidoptera, such as fall armyworms, moth larvae, inchworms, and heliotines in the family Noctuidae (e.g., fall armyworm (Spodoptera fugiperda JE Smith), beet fall armyworm (Spodoptera exigua Hubner), black moth larvae (Agrotis ipsilon Hufnagel), cabbage inchworm (Trichoplusia ni Hubner), tobacco budworm (Heliotis virescens Fabricius)); woodworms, box carriers, autumn worms, cone worms, cabbage worms, and skeletonizers of the family Pyralidae (e.g., European corn armyworm (Ostrinia nubilalis)). Hubner), navel orange worm (Idnyeloas transitella) Walker), autumn corn rootworm (Crambus caliginosellus Clemens), autumn lawn worm (Herpetogramma licarsisalis Walker); cicadas, budworms, seedworms and fruitworms in the family Tortricidae (e.g., apple moth (Cydia pomonella Linnaeus), grape berry moth (Endopiza viteana)) Clemens), oriental fruit moth (Grapholita molesta Busck); and many other commercially important Lepidoptera (e.g., diamondback moth (Plutella xylostella Linnaeus), pink bollworm (Pectinophora gossypiella Saunders), gypsy moth (Lymantria dispar Linnaeus)); nymphs and adults of the order Blattodea including cockroaches of the families Blattellidae and Blattidae (e.g., oriental cockroach (Blatta orientalis Linnaeus), Asian cockroach (Blatella asahinai Mizukubo), German cockroach (Blattella gemnanica Linnaeus), brown-banded cockroach (Supella longipalpa Fabricius), American cockroach (Periplaneta americana Linnaeus), brown cockroach (Periplaneta Petition 870220032852, dated 04 / 18 / 2022, page 113 / 320 106 / 312 brunnea Burmeister), hard-shelled cockroach (Leucophaea maderae Fabricius)); leaf-feeding larvae and adults of the order Coleoptera including weevils of the families Anthribidae, Bruchidae and Curculionidae (e.g., cotton boll weevil (Anthonomus grandis Boheman), water weevil (Lissorhoptrus oryzophilus Kuschel), grain weevil (Sitophilus granarius Linnaeus), rice weevil (Sitophilus oryzae Linnaeus)); jumping beetle, cucumber beetle, rootworm, green-yellow beetle, potato beetles and leafminers in the family Chrysomelidae (e.g., Colorado potato beetle (Leptinotarsa ​​decemlineata Say), western corn rootworm (Diabrotica virgifera LeConte)); scarabs and other beetles of the family Scaribaeidae (e.g., Japanese beetle (Popillia japonica Newman) and European beetle (Rhizotrogus majalis Razoumowsky)); carpet beetles of the family Dermestidae; wireworms of the family Elateridae; Scolytidae beetles and mealybugs. Additionally, it includes: adults and larvae of the order Dermaptera, including earwigs of the family Forficulidae (e.g., European earwig (Forficula auricularia Linnaeus), black earwig (Chelisoches mono Fabricius)); adults and nymphs of the orders Hemiptera and Homoptera, such as plant bugs of the family Miridae, cicadas of the family Cicadidae, leafhoppers (e.g., Empoasca spp.) of the family Cicadellidae, leafhoppers of the families Fulgoroidae and Delphacidae, soldier bugs of the family Membracidae, psyllids of the family Psyllidae, whiteflies of the family Aleyrodidae, aphids of the family Aphididae, phylloxera of the family Phylloxeridae, and scale insects. Petition 870220032852, dated 04 / 18 / 2022, pp. 114 / 320 107 / 312 mealybugs of the family Pseudococcidae, scale insects of the families Coccidae, Diaspididae and Margarodidae, azalea lace bugs of the family Tingidae, stink bugs of the family Pentatomidae, true stink bugs (e.g., Blissus spp.) and other seed bugs of the family Lygaeidae, salivary stink bugs of the family Cercopidae, pumpkin weevil of the family Coreidae and red and cotton-staining stink bugs of the family Pyrrhocoridae. In addition, adults and larvae of the order Acari (mites) are included, such as spider mites and red mites in the family Tetranychidae (e.g., European red mite (Panonychus ulmi Koch), two-spotted spider mite (Tetranychus urticae Koch), McDaniel's mite (Tetranychus mcdanieli McGregor)), flat mites in the family Tenuipalpidae (e.g., citrus flat mite (Brevipalpus lewisi McGregor)).erinose-dalichia mites in the family Eriophyidae and other leaf-feeding mites and mites that impact human and animal health, i.e., dust mites in the family Epidermoptidae, follicle mites in the family Demodicidae, grain mites in the family Glycyphagidae, ticks in the order Ixodidae (e.g., deer tick (Ixodes scapularis Say), Australian paralysis tick (Ixodes holocyclus Neumann), American dog tick (Dermacentor variabilis Say), lone star tick (Amblyomma americanum Linnaeus) and scabies and itch mites in the families Psoroptidae, Pyemotidae and Sarcoptidae; adults and non-adults of the order Orthoptera including grasshoppers, locusts and crickets (e.g., migratory grasshoppers (by for example, Melanoplus sanguinipes Fabricius, M. differentialis Thomas), American grasshoppers (for example, Schistocerca americana, Petition 870220032852, dated 04 / 18 / 2022, page 115 / 320 108 / 312 Drury), desert locusts (Schistocerca gregaria Forskal), migratory locust (Locusta migratoria Linnaeus), house cricket (Acheta domesticus Linnaeus), soft crickets (Gryllotalpa spp.)); adults and non-adults of the order Diptera including leaf miners, wheat midge, fruit flies (Tephritidae), Oscinella frits (e.g., Oscinella frit Linnaeus), soil worms, houseflies (e.g., Musca domestica Linnaeus), smaller houseflies (e.g., Fannia canicularis Linnaeus, F. femoralis Stein), stable flies (e.g., Stomoxis calcitrans Linnaeus), face flies, horn flies, blowflies (e.g., Chiysomya spp., Phonnia spp.), and other pests such as muscoidea flies, horseflies (e.g., Tabanus spp.), screwworm flies (e.g., Gastrophilus spp., Oestrus spp.), cattle grubs (e.g., Hypoderma spp.), deer flies (e.g., Chrysops spp.), false ticks (e.g., Melophagus ovinus Linnaeus) and other Brachycera, mosquitoes (e.g., Aedes spp., Anopheles spp., Culex spp.), black flies (e.g. Prosimulium spp., Simulium spp.), wheat-boring mosquitoes, sandflies, sciaridae and other Nematocera; adults and non-adults of the order Thysanoptera including hair thrips (Thrips tabaci Lindeman) and other leaf-feeding thrips; insect pests of the order Hymenoptera including ants (e.g., red sugar ant (Camponotus ferrugineus Fabricius), black sugar ant (Camponotus pennsylvanicus De Geer), Pharaoh ant (Monomorium pharaonis Linnaeus), small fire ant (Wasmannia auropunctata Roger), fire ant (Solenopsis geminata Fabricius), Petition 870220032852, dated 04 / 18 / 2022, page 116 / 320. 109 / 312 imported red fire ant (Solenopsis invicta Buren), Argentine ant (Iridomyrmex humilis Mayr), crazy ant (Paratrechina longicornis Latreille), pavement ant (Tetramorium caespitum Linnaeus), cornfield ant (Lasius alienus Fõrster), smelly house ant (Tapinoma sessile Say), bees (including carpenter bees), hornets, yellow jackets and wasps; insect pests of the order Isoptera including the eastern subterranean termite (Reticulitermes flavipes Kollar), western subterranean termite (Reticulitermes hesperus Banks), Formosan subterranean termite (Coptotermes formosanus Shiraki), west Indian drywood termite (Incisitermes immigrans Snyder) and other termites of economic importance; Insect pests of the order Thysanura such as silverfish (Lepisma saccharina Linnaeus) and earwigs (Thermobia domestica Packard);Insect pests of the order Mallophaga, including the head louse (Pediculus humanus capitis De Geer), body louse (Pediculus humanus humanus Linnaeus), chicken body louse (Menacanthus stramineus Nitszch), dog biting louse (Trichodectes cams De Geer), chewing louse (Goniocotes gallinae De Geer), sheep body louse (Bovicola ovis Schrank), short-nosed cattle louse (Haematopinus eurystemus Nitzsch), long-nosed cattle louse (Linognathus vituli Linnaeus), and other parasitic sucking or chewing lice that attack humans and animals; Insect pests of the order Siphonoptera including the oriental rat flea (Xenopsylla cheopis Rothschild), cat flea (Ctenocephalides felis Bouche), dog flea (Ctenocephalides canis Curtis), chicken flea (Ceratophyllus gallinae Schrank), and sticky flea; Petition 870220032852, dated 04 / 18 / 2022, page 117 / 320 110 / 312 (Echidnophaga gallinacea Westwood), human flea (Pulex irritans Linnaeus) and other fleas that affect animals and birds. Additional arthropod pests covered include: spiders in the order Araneae such as the brown recluse spider (Loxosceles reclusa Gertsch and Mulaik) and the black widow spider (Latrodectus mactans Fabricius) and centipedes in the order Scutigeromorpha such as the house centipede (Scutigera coleoptrata Linnaeus). The activity also includes members of the Classes Nematoda, Cestoda, Trematoda and Acanthocephala, including economically important members of the orders Strongylida, Ascaridida, Oxyurida, Rhabditida, Spirurida and Enoplida, as well as, but not limited to, economically important agricultural pests (i.e., root-node nematodes in the genus Meloidogyne, lesion nematodes in the genus Pratylenchus, short-root nematodes in the genus Trichodorus, etc.).) and pests that affect animal and human health (i.e., all parasites of economic importance, tapeworms and intestinal roundworms, such as Strongylus vulgaris in horses, Toxocara canis in dogs, Haemonchus contortus in sheep, Dirofllaria immitis Leidy in dogs, Anoplocephala peifoliata in horses, Fasciola hepatica Linnaeus in ruminants, etc.).

[0200] The compounds of the present invention show particularly high activity against pests in the order Lepidoptera (for example, Alabama argillacea Hubner (cotton leafworm), Archips argyrospila Walker (fruit tree caterpillar), A. rosana Linnaeus (European cornstalk borer) and other species of Archips, Chilo suppressalis Walker (rice stem borer), Cnaphalocrosis medinalis Guenee (rice armyworm), Crambus caliginosellus Clemens (rice rootworm) Petition 870220032852, dated 04 / 18 / 2022, pp. 118 / 320 111 / 312 autumn corn), Crambus teterrellus Zincken (autumn field grass worm), Cydia pomonella Linnaeus (apple worm), Earias insulana Boisduval (spiny caterpillar), Earias vittella Fabricius (spotted caterpillar), Helicoveipa armigera Húbner (American corn earworm), Helicoverpa zea Boddie (tobacco earworm), Heliotis virescens Fabricius (tobacco budworm), Herpetogramma licarsisalis Walker (lawn autumn worm), Lobesia botrana Denis and Schiffennúller (grape berry moth), Pectinophora gossypiella Saunders (pink bollworm), Phyllocnistis citrella Stainton (citrus leafminer), Pieris brassicae Linnaeus (large white butterfly), Pieris rapae Linnaeus (small white butterfly), Plutella xylostella Linnaeus (diamond diamondback moth), Spodoptera exigua Hubner (fall armyworm). beetroot), Spodoptera litura Fabricius (tobacco moth larvae, armyworm), Spodoptera frugiperda JE Smith (fall armyworm), Trichoplusia ni Húbner (cabbage looper) and Tula absoluta Meyrick (tomato leafminer)).

[0201] The compounds of the present invention also have commercially significant activity against members of the order Homoptera, including: Acyrtisiplionpisum Harris (pea aphid), Aphis craccivora Koch (cowpea aphid), Aphis fabae Scopoli (black bean aphid), Aphis gossypii Glover (cotton aphid, melon aphid), Aphis pomi De Geer (apple aphid), Aphis spiraecola Patch (spiraea aphid), Aulacorthum solani Kaltenbach (sorrel aphid), Chaetosiphon fragaefolii Cockerell (strawberry aphid), Diuraphis noxia Kurdjumov / Mordvilko (Russian wheat aphid), Dysaphis plantaginea Paaserini (apple aphid). Petition 870220032852, dated 04 / 18 / 2022, pp. 119 / 320 112 / 312 roseada), Eriosoma lanigerum Hausmann (apple woolly aphid), Hyalopterus pruni Geoffroy (plum aphid), Lipaphis erysimi Kaltenbach (turnip aphid), Metopolophium dirrhodum Walker (cereal aphid), Macrosipum euphorbiae Thomas (potato aphid), Myzus persicae Sulzer (peach and apple aphid, green peach aphid), Nasonovia ribisnigri Mosley (lettuce aphid), Pemphigus spp. (root aphids and gall aphids), Rhopalosiphum maidis Fitch (corn leaf aphid), Rhopalosiphumpadi Linnaeus (cherry aphid), Schizaphis graminum Rondani (green aphid), Sitobion avenae Fabricius (corn aphid), Therioaphis maculata Buckton (spotted alfalfa aphid), Toxoptera aurantii, Boyer de Fonscolombe (black aphid) and Toxoptera citiicida Kirkaldy (brown aphid); Adelges spp. (adelgids); Phylloxera devastatrix Pergande (pecan phylloxera); Bemisia tabaci Gennadius (tobacco whitefly, sweet potato whitefly), Bemisia argentifolii Bellows and Perring (grey leaf whitefly), Dialeurodes citri Ashmead (citrus whitefly) and Trialeurodes vaporariorum Westwood (greenhouse whitefly); Empoasca fabae Harris (green potato leafhopper), Laodelphax striatellus Fallen (lesser brown leafhopper), Macrolestes quadrilineatus Forbes (green aster leafhopper), Nephotettix cinticeps Uhler (green leafhopper), Nephotettix nigropictus Stal (green rice leafhopper), Nilaparvata lugens Stal (brown leafhopper), Peregrinus maidis Ashmead (corn leafhopper), Sogatella furcifera Horvath (white-backed leafhopper), Sogatodes orizicola Muir (rice delphicid), Typhlocyba pomaria McAfee (white apple leafhopper), Erythroneoura spp. ( Petition 870220032852, dated 04 / 18 / 2022, pp. 120 / 320 113 / 312 green grape leafhoppers); Magicidada septendecim Linnaeus (periodic cicada); Icerya purchasi Maskell (white aphid), Quadraspidiotus perniciosus Comstock (St. Joseph's aphid); Pianococcus citri Risso (citrus mealybugs); Pseudococcus spp. (another complex of mealybugs); Cacopsylla pyricola Foerster (pear psyllid), Trioza diospiri Ashmead (persimmon psyllid).

[0202] These compounds also have activity in members of the order Hemiptera including: Acrostemum hilare Say (green stink bug), Anasa tristis De Geer (pumpkin stink bug), Blissus leucopterus leucopterus Say (true stink bug), Corythuca gossypii Fabricius (cotton azalea lace bug), Cyrtopeltis modesta Distant (tomato stink bug), Dysdercus suturellus Herrich-S chaffer (cotton stink bug), Euchistus servus Say (brown stink bug), Euchistus variolrius Palisot deBeauvois (single-spot stink bug), Graptósthetus spp. (seed bug complex), Leptoglossus corculus Say (pine leaf bug), Lygus lineolaris Palisot de Beauvois (spotted plant bug), Nezara viridula Linnaeus (southern green stink bug), Oebalus pugnax Fabricius (rice stink bug), Oncopeltus fasciatus DaEas (large milkweed bug), Pseudatomoscelis seriatus Reuter (cotton aphid).

[0203] Other insects that are controlled by compounds of formula (I) of the present invention include: Thysanoptera (e.g., Frankliniella occidentalis Pergande (western flower thrips), Scirthothrips citri Moulton (citrus thrips), Sericothrips variabilis Beach (bean thrips)). Petition 870220032852, dated 04 / 18 / 2022, pp. 121 / 320 114 / 312 soybean) and Thrips tabaci Lindeman (onion thrips); and an order Coleoptera (e.g., Leptinotarsa ​​decemlineata Say (Colorado potato beetle), Epilachna varivestis Mulsant (Mexican bean beetle), and wireworms of the genera Agriotes, Athous, or Limonius).

[0204] Specifically, the compounds of formula (I), their N-oxides, their isomers, polymorphs, and salts are especially suitable for effectively combating the following pests: insects of the order Lepidoptera, for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyrestia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Chilo infuscatellus, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Earias vittala, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholita funebrana, Grapholita molesta, Helicoverpa armigera, Helicoverpa virescens, Helicoverpa zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Leucinodes orbonalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea Petition 870220032852, dated 18 / 04 / 2022, p. 122 / 320 115 / 312 operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scirpophaga incertulas, Scrobipalpula absoluta, Sitotroga cerealella, Sparganotis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Spodoptera exigua, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis; e

[0205] Beetles (Coleoptera), for example, Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aphthona euphoridae, Athous haemorrhoidalis, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Ctenicera ssp., Diabrotica longicornis, Diabrotica semipunctata, Diabrotica undecimpunctata Diabrotica speciosa, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa ​​decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha, Oulema oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllobius piri, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona. Petition 870220032852, dated 18 / 04 / 2022, p. 123 / 320 116 / 312 lineatus from Sitophilus granaria; flies, mosquitoes (Diptera), for example, Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans,Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga haemorrhoidalis, Sarcophaga spp., Simulium vittatum, Stomoxis calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus, Petition 870220032852, dated 18 / 04 / 2022, p. 124 / 320 117 / 312 similis, Tipula oleracea from Tipula paludosa; cupins (Isoptera), for example, Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes grassei, Termes natalensis and Coptotermes formosanus; cockroaches (Blattaria Blattodea), for example, Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae and Blatta orientalis; ants, bees, wasps, sawflies (Hymenoptera), for example, Athalia rosae, Atta cephalotes, Atta capiguara, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Lasius niger, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex californicus, Pheidole megacephala, Dasymutilla occidentalis, Bombus spp., Vespula squamosa, Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolichovespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile; crickets, grasshoppers, locusts (Orthoptera), for example, Acheta domestica, Gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Calliptamus italicus, Petition 870220032852, dated 18 / 04 / 2022, p. 125 / 320 118 / 312 Chortoicetes terminifera and Locustana pardalina; Araneida, e.g., Latrodectus mactans, and Loxosceles reclusa; ticks (Siphonaptera), e.g., Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus; silverfish, firebrat (Thysanura), e.g., Lepisma saccharina and Thermobia domestica; centipedes (Chalopoda), e.g., Scutigera oleoptrata; diplopods (Diplopoda), e.g., Narceus spp.; earwigs (Dermaptera), e.g., Forficula auricularia; lice (Phtiraptera), e.g., Pediculus humanus capitis, Pediculus humanus corporis, Ptirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon allinae, Menacanthus stramineus, and Solenopotes capillatus. Collembola (colêmbolos), for example, Onychiurus ssp.

[0206] The compounds of formula (I) of the present invention are also suitable for controlling nematodes: plant parasitic nematodes, such as root-knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii and other Heterodera species; seed-knot nematodes, Anguina species; stem and leaf nematodes, Aphelenchoides species; stinging nematodes, Belonolaimus longicaudatus and other Belonolaimus species; pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; ring nematodes, Criconema species, Petition 870220032852, dated 04 / 18 / 2022, pp. 126 / 320 119 / 312 species of Criconemella, species of Criconemoides, species of Mesocriconema; stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other species of Ditylenchus; boring nematodes, species of Dolichodorus; spiral nematodes, Heliocotylenchus multicinctus and other species of Helicotylenchus; sheath and sheathoid nematodes, species of Hemicycliophora and species of Hemicriconemoides; species of Hirshmanniella; cigar nematodes, species of Hoploaimus; false root-knot nematodes, species of Nacobbus; needle nematodes, Longidorus elongatus and other species of Longidorus; lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; burrowing nematodes, Radopholus similis and other Radopholus species; reniform nematodes, Rotylenchus robustus and other Rotylenchus species; Scutellonema species; short-rooted nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; stunting nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; citrus nematodes, Tylenchulus species; dagger nematodes, Xiphinema species; and other plant parasitic nematode species.

[0207] The compounds of formula(I) and their salts are also useful for controlling arachnids (Arachnoidea), such as mites (Acarina), for example, of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Petition 870220032852, dated 04 / 18 / 2022, pp. 127 / 320 120 / 312 Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp., such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp., such as Brevipalpus phoenicis; Tetranychidae spp., such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri and oligonychus pratensis.

[0208] In one embodiment of the present invention, the present invention provides the compound of formula (I) which is useful for controlling selected insects from sucking and boring insects of the genera Thysanoptera, Diptera and Hemiptera, in particular, the following species of:

[0209] Thysanoptera: Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,

[0210] Diptera: Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dacus Petition 870220032852, dated 18 / 04 / 2022, p. 128 / 320 121 / 312 cucurbits, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila roseae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga haemorrhoidalis, Sarcophaga spp., Simulium vittatum, Stomoxis calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, Tipula oleracea and Tipula paludosa;.

[0211] Hemiptera, specifically, aphids: Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis Petition 870220032852, dated 18 / 04 / 2022, p. 129 / 320 122 / 312 pears, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pirarius, Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mail, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantii and Viteus vitifolii.

[0212] In one embodiment, the present invention provides a composition comprising a biologically effective amount of the compound of formula (I) and at least one additional biologically active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients. The compounds used in the composition and in combination with the compound of formula (I) are also referred to as active compatible compounds.

[0213] Known and related fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics and nutrients may be combined with at least one compound of formula (I) of the present disclosure. For example, disclosed fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients Petition 870220032852, dated 04 / 18 / 2022, pp. 130 / 320 123 / 312 and reported in documents WO2016156129 and / or WO2017153200 may be combined with at least one compound of formula (I) of the present disclosure.

[0214] Fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients reported in document WO2016156129 and / or document WO2017153200 are incorporated herein by reference as non-limiting examples to be combined with at least one compound of formula (I) of this disclosure.

[0215] Specifically, the compounds of the present invention can be mixed with at least one additional compatible biologically active compound (mixing partner) which includes, but is not limited to, insecticides, fungicides, nematocides, bactericides, acaricides, growth regulators such as rooting stimulants, chemosterifying agents, semiochemicals, repellents, attractants, pheromones, feeding stimulants, other biologically active compounds or entomopathogenic bacteria, viruses or fungi to form a multi-component pesticide that provides an even broader spectrum of agricultural utility.

[0216] Examples of such compounds or biologically active mixing agents / partners with which the compound of formula (I) of the present invention may be combined / formulated are disclosed in the document. WO2019072906A1 (pages 27 to 37).

[0217] In one embodiment, the biological agents for mixing with the compounds of the present invention include Bacillus thuringiensis, Bacillus delta endotoxin Petition 870220032852, dated 04 / 18 / 2022, pp. 131 / 320 124 / 312 thuringiensis as well as genetically modified viral insecticides and naturally occurring insects including members of the Baculoviridae family as well as entomophagous fungi.

[0218] In certain instances, combinations with other compounds or invertebrate pest control agents that have a similar spectrum of control but a different mode of action will be particularly advantageous for resistance management. Thus, the compositions of the present invention may additionally comprise a biologically effective amount of at least one compound or invertebrate pest control agent that has a similar spectrum of control but a different mode of action. Contact with the genetically modified plant expressing a plant protection compound (e.g., protein) or the plant site with a biologically effective amount of a compound of the invention may provide a broader spectrum of plant protection and be advantageous for resistance management.

[0219] In one embodiment of the present invention, the biologically effective amount of the compound of formula (I) in the compositions ranges from 0.1% to 99% by weight relative to the total weight of the composition, preferably from 5% to 50% by weight relative to the total weight of the composition.

[0220] The present invention further provides a method for controlling invertebrate pests, said method comprising contact with the invertebrate pests, their habitat, breeding soil, food supply, plant, seed, soil, area, material or environment in which the invertebrate pests are growing or may grow. Petition 870220032852, dated 04 / 18 / 2022, page 132 / 320 125 / 312 grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected against pest attack or infestation with a biologically effective amount of the compound or composition of the present invention.

[0221] Invertebrate pests are controlled, and the protection of agronomic, horticultural, and spice crops, and human and animal health is achieved by effectively applying one or more of the compounds of the present invention to the pest environment, including the agronomic and / or non-agronomic infestation site, the area to be protected, or directly to the pests to be controlled. Thus, the present invention further comprises a method for controlling leaf- and soil-dwelling invertebrates and protecting agronomic and / or non-agronomic crops, comprising contact with the invertebrates or their environment with a biologically effective amount of one or more of the compounds of the present invention, or with a composition comprising at least such a compound, or a composition comprising at least such a compound and an effective amount of at least one additional biologically active compound or agent. A preferred method of contact is by spraying.Alternatively, a granular composition comprising a compound of the present invention can be applied to the plant foliage or to the soil. The compounds of the present invention are effective in delivery through plant absorption by placing the plant in contact with a composition comprising a compound of the present invention applied as a soil-applied spray of a liquid formulation, a granular soil formulation, a nursery box treatment, or an immersion. Petition 870220032852, dated 04 / 18 / 2022, page 133 / 320 126 / 312 transplants. Other contact methods include application of a compound or composition of the present invention by direct and residual spraying, aerial spraying, seed coatings, microencapsulation, systemic absorption, baits, ear tags, cakes, mist formers, fumigants, aerosols, dusting, and many others.

[0222] The compounds of the present invention can be incorporated into baits that are consumed by invertebrates or within devices such as traps and the like. Granules or baits comprising between 0.01-5% active ingredient, 0.05-10% moisture-retaining agent (or moisture-retaining agents) and 40-99% vegetable flour are effective in controlling soil insects at very low application rates, specifically, at doses of active ingredient that are lethal by ingestion rather than by direct contact. The compounds of the present invention can be applied in their pure state, however, very often, the application will be of a formulation comprising one or more compounds with suitable carriers, diluents and surfactants and possibly in combination with a feed depending on the contemplated end use. A preferred method of application involves spraying a water or refined oil dispersion solution of the compounds.Combinations with spray oils, spray oil concentrations, spreading adhesives, adjuvants, other solvents and synergists such as piperonyl butoxide often enhance the effectiveness of the compound.

[0223] The application rate required for effective control (i.e., biologically effective amount) will depend on factors such as the invertebrate species to be controlled, the life cycle of the pest, stage of. Petition 870220032852, dated 04 / 18 / 2022, page 134 / 320 127 / 312 life cycle, size, location, time of year, host crop or animal host, feeding behavior, mating behavior, ambient humidity, temperature, and similar factors. Under normal circumstances, application rates of about 0.01 to 2 kg of the active ingredient per hectare are sufficient to control pests in agronomic ecosystems, however, a minimum of 0.0001 kg / hectare may be sufficient or as much as 8 kg / hectare may be necessary. For non-agronomic applications, effective use rates range from about 1.0 to 50 mg / square meter, however, a minimum of 0.1 mg / square meter may be sufficient or as much as 150 mg / square meter may be necessary. A technician in the field can easily determine the biologically effective amount needed for the desired level of invertebrate pest control.

[0224] The animal pest, that is, insects, arachnids and nematodes, the plant, soil or water in which the plant is growing may come into contact with the compounds of formula (I), their N-oxides and salts or composition(s) containing the same by any method of application known in the art. Thus, contact includes both direct contact (applying the compounds / compositions directly to the animal or plant pest, typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds / compositions to the location of the animal or plant pest).

[0225] The compounds of the present invention or the pesticide compositions comprising them may be used to protect growing plants and crops against attack or infestation by animal pests, especially insects, acarids or arachnids, by contact. Petition 870220032852, dated 04 / 18 / 2022, pp. 135 / 320 128 / 312 of the plant / crop with a pesticidal amount of at least one compound of the present invention. The term crop refers to both growing and harvested crops.

[0226] In one embodiment, the present invention provides a method for protecting crops against attack or infestation by invertebrate pests comprising placing the crop in contact with a biologically effective amount of the compound or composition of the present invention, isomer, polymorph, N-oxide or salt thereof.

[0227] The compounds of the present invention are employed in this manner or in the form of compositions by treating insects or plants, plant propagation materials such as seeds, soil, surfaces, materials or spaces to be protected against insecticide attack with an effective amount of the active compounds as an insecticide. The application can be applied both before and after infection of plants, plant propagation materials such as seeds, soil, surfaces, materials or spaces by insects.

[0228] In one embodiment, the present invention provides a method for protecting seeds from soil insects and from the roots of seedlings and sprouts in the soil and foliar insects comprising contacting the seeds, before sowing and / or after pre-germination, with the compound or composition of the present invention, N-oxide or salt thereof.

[0229] Furthermore, the present invention provides a method for treating or protecting animals against infestation or infection by parasites comprising administering orally, topically or parenterally or applying to animals the biologically effective amount of the compound or composition. Petition 870220032852, dated 04 / 18 / 2022, pp. 136 / 320 129 / 312 of this invention, isomer, polymorph, N-oxide or salt thereof acceptable in veterinary practice.

[0230] For use in the treatment of crop plants, the application rate (applying effective dosages) of the compound of the present invention may be in the range of 1 g a.m. to 5000 g a.m. per hectare in agricultural or horticultural crops, preferably 25 g a.m. to 600 g a.m. per hectare, more preferably 50 g a.m. to 500 g a.m. per hectare.

[0231] The compounds and compositions of the present invention are specifically useful in controlling various insects in various cultivated plants such as cereals, root crops, oil crops, vegetables, peppers, ornamental plants, for example, durum wheat seed and other wheat, barley, oats, rye, maize (forage maize and sugar maize / sweet and field maize), soybeans, oil crops, cruciferous plants, cotton, sunflowers, bananas, rice, oilseed rapeseed, turnip rapeseed, sugar beet and fodder beet, eggplant, potatoes, grass, lawn, turf, forage grass, tomatoes, leeks, pumpkin / zucchini, cabbage, iceberg lettuce, peppers, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugarcane, tobacco, grapes, petunias, geranium / pelargoniums, pansies and impatiens.

[0232] Specifically, the compound or composition of the present invention is useful in protecting against agricultural crops such as cereals, corn, rice, soybeans and other leguminous plants, fruits and fruit trees, grapes, nuts and walnut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oilseed plants, Petition 870220032852, dated 04 / 18 / 2022, page 137 / 320 130 / 312 Tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton, potatoes, tomatoes, onions, peppers and other vegetables and ornamental plants.

[0233] The compounds of the present invention are effective both by means of contact (by means of soil, glass, wall, mosquito net, carpet, plant parts or animal parts) and ingestion (bait or plant part).

[0234] The compounds of the present invention can also be applied against non-crop invertebrate pests, such as ants, termites, wasps, flies, mosquitoes, crickets or cockroaches. For use against said non-crop pests, compounds of the present invention are preferably used in a bait composition.

[0235] The bait can be a liquid, a solid, or a semi-solid preparation (e.g., a gel). Baits can have various shapes and forms suitable for the respective application, for example, granules, blocks, rods, discs. Liquid baits can be filled into various devices to ensure proper application, for example, open containers, spray devices, droplet sources, or evaporation sources. Gels can be based on aqueous or oily matrices and can be formulated for particular needs in terms of stickiness, moisture retention, or aging characteristics.

[0236] The bait used in the composition is a product that is sufficiently attractive to entice insects such as ants, termites, wasps, flies, mosquitoes, crickets, etc., or cockroaches to eat it. The attractiveness can be manipulated with the use of feeding stimulants or sex pheromones. Feeding stimulants are chosen, for example, however Petition 870220032852, dated 04 / 18 / 2022, page 138 / 320 131 / 312 not exclusively, from animal and / or vegetable proteins (meat, food from fish or blood, insect parts, egg yolk), from fats and oils of animal and / or vegetable origin or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts can also serve as a feeding stimulant. Sex pheromones are known to be insect-specific. Specific pheromones are described in the literature and are known to those skilled in the art.

[0237] For use in bait compositions, the typical content of the active ingredient is 0.001% by weight to 15% by weight, desirably 0.001% by weight to 5% by weight of the active compound.

[0238] Formulations of the compounds of the present invention as aerosols (e.g., in spray cans), oil sprays, or pump sprays are highly suitable for the non-professional user to control pests such as flies, fleas, ticks, mosquitoes, or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents such as lower alcohols (e.g., methanol, ethanol, propanol, butanol), ketones (e.g., acetone, methyl ethyl ketone), paraffinic hydrocarbons (e.g., kerosenes) having boiling ranges of about 50 to 250 °C, dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, and additional emulsifiers such as sorbitol monooleate, ethoxylate of Petition 870220032852, dated 04 / 18 / 2022, pp. 139 / 320 132 / 312 oleyl containing 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, suitable stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if necessary, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide or mixtures of these gases.

[0239] Oil spray formulations differ from aerosol recipes in that propellants are not used. For use in spray compositions, the active ingredient content is 0.001 to 80% by weight, preferably 0.01 to 50% by weight, and most preferably 0.01 to 15% by weight.

[0240] The compounds of the present invention and their respective compositions can also be used in mosquito and fumigation coils, smoke cartridges, vaporization plates or long-term vaporizers and also in moth papers, moth blocks or other heat-independent vaporizing systems.

[0241] Methods for controlling infectious diseases transmitted by insects (for example, malaria, dengue and yellow fever, lymphatic filariasis and leishmaniasis) with compounds of formula (I) and their respective compositions also include treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, mosquito nets, tsetse fly traps or similar. Insecticidal compositions for application to fibers, fabrics, knitwear, non-woven fabrics, netting or sheets and Petition 870220032852, dated 04 / 18 / 2022, pp. 140 / 320 133 / 312 tarpaulins, preferably, comprise a mixture including the insecticide, optionally a repellent and at least one binder. Suitable repellents include, for example, N,N-diethylmeta-toluamide (DEET), N,N-diethylphenylacetamide (DEPA), 1-(3-cyclohexan-1-ylcarbonyl)-2-methylpiperine, (2-hydroxymethylcyclohexyl)acetic acid lactin, 2-ethyl-1,3-hexandiol, indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insect control such as {(+ / -)3-allyl-2-methyl4-oxocyclopent-2-(+)-enyl-(+)-transchrysanthemate (Esbiothrin), a repellent derived from or identical to plant extracts such as limonene, eugenol, (+)Eucamalol (1), (-)-l-epi-eucamalol or crude plant extracts from plants such as Eucalyptus maculata, Vitex rotundifolia, Cymbopogan martinii, Cymbopogan citratus (lemongrass), Cymopogan nartdus (citronella).Suitable binders are selected, for example from polymers and copolymers of vinyl esters of aliphatic acids (such as vinyl acetate and vinyl versicolor), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2-ethylhexyl acrylate and methyl acrylate, mono- and diethylenically unsaturated hydrocarbons, such as styrene, and aliphatic dienes, such as butadiene.

[0242] The impregnation of curtains and mosquito nets is generally done by immersing the textile material in emulsions or dispersions of insecticide or by spraying it onto the nets.

[0243] The compounds of the present invention and their compositions can be used to protect wood materials such as trees, fences, beams, etc., and buildings such as houses, outbuildings, factories, as well as construction materials, furniture, leather, fibers, vinyl articles, Petition 870220032852, dated 04 / 18 / 2022, page 141 / 320 134 / 312 electrical wires and cables etc. against ants and / or termites, and to control ants and termites so that they do not harm crops or human beings (for example, when pests invade homes and public facilities). The compounds of the present invention are applied not only to the surrounding surface of the soil or in the subsoil in order to protect wood materials, but can also be applied to sawn articles such as concrete surfaces in the subsoil, alcove pests, beams, plywood, furniture etc., articles of wood such as particleboard, half-board etc. and vinyl items such as coated electrical wires, vinyl sheets, heat insulating material such as styrene foams etc.

[0244] In the case of application against ants that harm crops or humans, a compound of the present invention is applied to the crops or surrounding soil or is applied directly to the ant nest or similar. Seed treatment

[0245] The present invention further provides a treated seed comprising the compounds of the present invention, specifically, in an amount in a range of about 0.0001% to approximately 1% by weight of the seed before treatment.

[0246] The compounds of the present invention are also suitable for seed treatment in order to protect the seed against insect pests, in particular, against soil-dwelling insects and mite pests, and the resulting plant roots and shoots against foliar pests and insects.

[0247] The compounds of the present invention are Petition 870220032852, dated 04 / 18 / 2022, page 142 / 320 135 / 312 specifically useful for protecting seeds from soil pests and the resulting plant roots (whiteworms, termites, wireworms) and shoots from soil pests and leaf insects. Protection of the roots and resulting plant shoots is preferential. More preferential is the protection of the resulting plant shoots from boring and sucking insects, where protection against aphids, leafhoppers, thrips and whiteflies is of highest preference.

[0248] The present invention therefore comprises a method for protecting seeds against insects, in particular against soil insects, and leaf roots and shoots against insects, in particular against soil and leaf insects, wherein said method comprises placing the seeds, before sowing and / or after pre-germination, in contact with a compound of the present invention. A particularly preferred method is one in which the roots and shoots of the plant are protected, more preferably a method in which the plant shoots are protected against boring and sucking insects, most preferably a method in which the plant shoots are protected against aphids.

[0249] The term seed covers seeds and plant propagules of all kinds including, but not limited to, true seeds, seed pieces, suckers, chromosomes, bulbs, fruits, tubers, grains, cuttings, cut shoots and the like, and means, in a preferred embodiment, true seeds.

[0250] The term seed treatment encompasses all suitable seed treatment techniques known in the art, such as seed film coating, coating of Petition 870220032852, dated 04 / 18 / 2022, page 143 / 320 136 / 312 seed, seed dusting, seed soaking and seed pelleting.

[0251] The present invention also comprises seeds coated with the active compound containing the same. The seeds may be coated with seed coating compositions containing the compounds of the present invention. For example, seed coating compositions reported in documents EP3165092, EP3158864, WO2016198644, WO2016039623, WO2015192923, CA2940002, US2006150489, US2004237395, WO2011028115, EP2229808, WO2007067042, EP1795071, EP1273219, WO200178507, EP1247436, NL1012918 and CA2083415.

[0252] The term “coated with and / or containing” generally means that the active ingredient is largely on the surface of the propagation product at the time of application, although a greater or lesser portion of the ingredient may penetrate the propagation product, depending on the application method. When (re)planted, the propagation product may absorb the active ingredient along with moisture.

[0253] Suitable seeds are cereal seeds, root crops, oil crops, vegetables, peppers, ornamental plants, for example, durum wheat seed and other wheat, barley, oats, rye, maize (forage maize and sugar maize / sweet and field maize), soybeans, oil crops, cruciferous plants, cotton, sunflowers, bananas, rice, oilseed rapeseed, turnip rapeseed, sugar beet and fodder beet, eggplant, potatoes, grass, lawn grass, forage grass, tomatoes, leeks, pumpkin / zucchini, cabbage, iceberg lettuce, peppers, cucumbers, melons, Brassica species, cantaloupes, beans, Petition 870220032852, dated 04 / 18 / 2022, p. 144 / 320 137 / 312 peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geraniums / pelargoniums, pansies and impatiens.

[0254] In addition, the compounds of the present invention can be used to treat seed against plants that tolerate the action of herbicides or fungicides or insecticides due to improvement, including genetic engineering methods.

[0255] For example, the compound of the present invention can be used in the treatment of seeds of plants that are resistant to herbicides of the group consisting of sulfonylureas, imidazolinones, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active substances (see, for example, documents EP242236, EP242246) (document WO92 / 00377) (documents EP257993, US5013659) or in transgenic crops, for example, cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins) that make the plants resistant to certain pests (documents EP142924, EP193259).

[0256] Furthermore, the compound of the present invention can be used for seed treatment of plants that have modified characteristics compared to existing plants, which can be generated, for example, by traditional breeding methods and / or the generation of mutants, or by recombinant procedures. For example, several cases of recombinant modifications of crop plants have been described for the purpose of modifying the starch synthesized in the plants (e.g., documents WO92 / 11376, WO92 / 14827, WO91 / 19806) or transgenic crop plants that have a modified fatty acid composition (document Petition 870220032852, dated 04 / 18 / 2022, page 145 / 320 138 / 312 WO91 / 13972).

[0257] The seed treatment application of the compound of the present invention is carried out by spraying or dusting the seeds before sowing the plants and before the plants emerge.

[0258] Compositions that are especially useful for seed treatment include, for example: A. Soluble concentrates (SL, LS) B. Emulsions (EW, EO, ES) C. Suspensions (SC, OD, FS) D. Water-dispersible granules and water-soluble granules (WG, SG) E. Water-dispersible powders and water-soluble powders (WP, SP, WS) F. Gel Formulations (GF) G. Dustable Powders (DP, DS)

[0259] Conventional seed treatment formulations include, for example, fluidizable FS concentrates, LS solutions, DS dry treatment powders, WS water-dispersible paste treatment powders, SS water-soluble powders and ES and EC emulsions, and GF gel formulations. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing or directly on the seeds or after they have pre-germinated from the latter.

[0260] In one embodiment, a seed treatment formulation is used for seed treatment. Typically, a seed treatment formulation may comprise 1-800 g / l of active ingredient, 1-200 g / l of surfactant, 0 to 200 g / l of antifreeze agent, 0 to 400 g / l of binder, 0 to 200 g / l of a pigment, and up to 1 liter Petition 870220032852, dated 04 / 18 / 2022, pp. 146 / 320 139 / 312 of a solvent, preferably water.

[0261] Specifically, FS formulations of the compounds of the present invention for seed treatment typically comprise 0.1 to 80% by weight (1 to 800 g / l) of the active ingredient, 0.1 to 20% by weight (1 to 200 g / l) of at least one surfactant, for example, 0.05 to 5% by weight of a wetting agent and 0.5 to 15% by weight of a dispersing agent, up to 20% by weight, for example, 5 to 20% of an antifreeze agent, 0 to 15% by weight, for example, 1 to 15% by weight of a pigment and / or a dye, 0 to 40% by weight, for example, 1 to 40% by weight of a binder (sticky / adhesive agent), optionally up to 5% by weight, for example, 0.1 to 5% by weight of a thickener, optionally 0.1 to 2% of a non-foaming agent and optionally a preservative such as a biocide, antioxidant or similar, for example, in an amount of 0.01 to 1% by weight and a filler / vehicle up to 100% by weight.

[0262] Seed treatment formulations may additionally comprise binders and optionally colorants.

[0263] Binders may be added to enhance the adhesion of active materials to seeds after treatment. Suitable binders are homo- and copolymers of alkylene oxides such as ethylene oxide or propylene oxide, polyvinyl acetate, polyvinyl alcohols, polyvinylpyrrolidone and copolymers thereof, ethylene-vinyl acetate copolymers, acrylic homo- and copolymers, polyethyleneamines, polyethyleneamides and polyethylenepyrimidines, polysaccharides such as cellulose, trilose and starch, polyolefin homo- and copolymers such as Petition 870220032852, dated 04 / 18 / 2022, page 147 / 320 140 / 312 olefin / maleic anhydride copolymers, polyurethanes, polyesters, homopolymers and copolymers of polystyrene.

[0264] Optionally, colorants may also be included in the formulation. Suitable colorants or dyes for seed treatment formulations are Rhodamine B, CI Red Pigment 1 12, CI Red Solvent 1, Blue Pigment 15:4, Blue Pigment 15:3, Blue Pigment 15:2, Blue Pigment 15:1, Blue Pigment 80, Yellow Pigment 1, Yellow Pigment 13, Red Pigment 1 12, Red Pigment 48:2, Red Pigment 48:1, Red Pigment 57:1, Red Pigment 53:1, Orange Pigment 43, Orange Pigment 34, Orange Pigment 5, Green Pigment 36, Green Pigment 7, White Pigment 6, Brown Pigment 25, Basic Violet 10, Basic Violet 49, Acid Red 51, Acid Red 52, Acid Red 14, Acid Blue 9, Acid Yellow 23, Basic Red 10, Basic Red 108.

[0265] An example of a gelling agent is carrageenan (Satiagel®)

[0266] In seed treatment, the application rates of the compounds of the present invention are generally 0.1 ga 10 kg per 100 kg of seed, preferably 1 ga 5 kg per 100 kg of seed, more preferably 1 ga 1000 g per 100 kg of seed and, in particular, 1 ga 200 g per 100 kg of seed. Therefore, the present invention provides seeds comprising a compound of formula (I), or a salt thereof useful in agricultural practice of I, as defined herein. The amount of compound I or the salt thereof useful in agricultural practice will generally vary from 0.1 ga 10 kg per 100 kg of seed, preferably from 1 ga 5 kg per 100 kg of seed, in Petition 870220032852, dated 04 / 18 / 2022, pp. 148 / 320 141 / 312 particular, 1 ga 1000 g per 100 kg of seed. For specific crops such as lettuce, the rate may be higher. Animal health

[0267] The present invention also provides an agricultural and / or veterinary composition comprising at least the compound of the present invention.

[0268] The present invention also additionally relates to a use of the compound, N-oxide or salt thereof acceptable in veterinary practice or the composition of the invention in the preparation of a medicament for treating or protecting animals against infestation or infection by invertebrate pests or parasites.

[0269] The compounds of formula (I), their N-oxides and / or salts acceptable in veterinary practice thereof are, in particular, suitable for use in combating parasites within animals or on their skin.

[0270] Therefore, an object of the present invention is to provide new methods for controlling parasites within animals or on their skin. Another object of the present invention is to provide pesticides that are safer for animals. Another object of the present invention is to provide pesticides for animals that can be used in lower doses than existing pesticides. Another object of the present invention is to provide pesticides for animals that provide long-lasting residual control of parasites.

[0271] The present invention also relates to compositions containing an effective amount for parasiticide of at least one compound of formula (I), N-oxide or salt thereof acceptable in veterinary practice and a carrier acceptable for combating parasites within animals or on the skin of Petition 870220032852, dated 04 / 18 / 2022, pp. 149 / 320 142 / 312 same.

[0272] The present invention also provides a method for treating, controlling, preventing and protecting animals against infestation and infection by parasites comprising administering orally, topically or parenterally or applying to animals an effective amount as a parasite of a compound of the present invention or a composition comprising the same.

[0273] The present invention also provides a process for preparing a composition for treating, controlling, preventing, and protecting animals against infestation or infection by parasites comprising the effective amount as a parasite of a compound of the present invention or a composition comprising the same.

[0274] The activity of the compounds against agricultural pests does not suggest their suitability for controlling endo- and ectoparasites inside animals and on their skin, which requires, for example, low non-emetic dosages in the case of oral application, metabolic compatibility with the animal, low toxicity and safe handling.

[0275] Surprisingly, it has been found that the compounds of the present invention are suitable for combating endo- and ectoparasites within animals and on their skin.

[0276] The compounds of the present invention and compositions comprising them are preferably used to control and prevent infestations in animals, including warm-blooded animals (including humans) and fish. They are, for example, suitable for controlling and preventing infestations and infections in mammals such as cattle, sheep, Petition 870220032852, dated 04 / 18 / 2022, pp. 150 / 320 143 / 312 pigs, camels, deer, horses, pigs, birds, rabbits, goats, puppies and cats, Asian buffalo, donkeys, fallow deer and reindeer, and also fur-bearing animals such as mink, chinchilla and raccoons, birds such as chickens, geese, turkeys and ducks, and fish, freshwater or saltwater fish such as trout, carp and eels.

[0277] The compounds of the present invention and compositions comprising them are preferably used to control and prevent infestations and infections in domestic animals, such as dogs or cats.

[0278] Infestations in warm-blooded animals and fish include, but are not limited to, lice, burrowing lice, ticks, nasal botflies, false ticks, burrowing flies, muscoidea flies, flies, myiasis fly larvae, maggots, gnats, mosquitoes and fleas.

[0279] The compounds of the present invention and compositions comprising them are suitable for systemic and / or non-systemic control of ecto- and / or endoparasites. They can be active against all developmental stages.

[0280] The compounds of the present invention are especially useful for combating ectoparasites.

[0281] The compounds of the present invention are especially useful for combating parasites of the following orders and species, respectively: fleas (Suphonaptera), for example, Ctenocephalides felis, Ctenocephalides cams, Xenopsylla cheopis, Pulex irritans, Tunga penetrans and Nosopsyllus fasciatus, cockroaches (Blattella Blattodea), for example, Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Petition 870220032852, dated 04 / 18 / 2022, pp. 151 / 320 144 / 312 Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae and Blatta orientalis, flies, mosquitoes (Diptera), for example, Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pi pi ens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxis calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, lice (Phtiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Ptirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus, and Solenopotes capillatus. parasitic ticks and mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes. Petition 870220032852, dated 18 / 04 / 2022, p. 152 / 320 145 / 312 scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), for example, Ornithonyssus bacoti and Dermanyssus gallinae, Actinedida (Prostigmata) and Acaridida (Astigmata) for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., from Laminosioptes spp., Percevejos (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. from Arilus critatus, Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., from Solenopotes spp., Mallophagida (suborder Arnblycerina e Ischnocerina), for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp. from Felicola spp. Intestinal nematode worms:

[0282] Whipworms and Trichinosis (Trichosyringida), e.g., Trichinellidae (Trichinella spp.), (Trichuridae,) Trichuris spp., Capillaria spp, Rhabditida, e.g., Rhabditis spp, Strongyloides spp., Helicephalobus spp, Strongylida, e.g., Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (Whipworm), Trichostrongylus spp., Haemonchus contortus., Ostertagia Petition 870220032852, dated 04 / 18 / 2022, page 153 / 320 146 / 312 spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylus abstrusus and Dioctophyma renale, Intestinal roundworms (Ascarids), e.g., Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Pixuriasis), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi, Camallanida, e.g., Dracunculus medinensis (guinea worm) Spirurida, e.g., Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp. a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp, Spiny-headed worms (Acanthocephala), e.g., Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp, planarians (Plathelminthes): Parasites (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria a lata, Paragonimus spp., and Nanocyetes spp, Cercomeromorpha, in particular Cestoda (Tenias), e.g., Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp. and Hymenolepis spp.

[0283] Compounds of formula (I) and compositions that Petition 870220032852, dated 04 / 18 / 2022, page 154 / 320 147 / 312 contain the same ingredients that are specifically useful for controlling pests of the orders Diptera, Siphonaptera, and Ixodida.

[0284] In one embodiment, the present invention provides use of the compounds of formula (I) and compositions containing the same to combat mosquitoes.

[0285] In one embodiment, the present invention provides use of the compounds of formula (I) and compositions containing the same for combating flies.

[0286] In one embodiment, the present invention provides use of the compounds of formula (I) and compositions containing the same for combating fleas.

[0287] The use of the compounds of the present invention and compositions containing them to combat ticks is another embodiment of the present invention.

[0288] The compounds of the present invention are also especially useful for combating endoparasitic nematodes (intestinal roundworms, spiny-headed worms and planarians).

[0289] In one embodiment, the administration of the compounds of the present invention can be carried out both prophylactically and therapeutically.

[0290] In another embodiment, administration of the compounds of the present invention is carried out directly or in the form of suitable preparations, orally, topically / dermally or parenterally.

[0291] For oral administration to warm-blooded animals, the compounds of the present invention can be formulated as animal feed, animal feed premixes, animal feed concentrations, pills, solutions, pastes, suspensions, syrups, Petition 870220032852, dated 04 / 18 / 2022, pp. 155 / 320 148 / 312 gels, tablets, boluses and capsules. In addition, the compounds of the present invention can be administered to animals in their drinking water. For oral administration, the chosen dosage form should provide the animal with 0.01 mg / kg to 100 mg / kg of body weight per day of the compound of the present invention, preferably with 0.5 mg / kg to 100 mg / kg of body weight per day.

[0292] Alternatively, the compounds of the present invention can be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The compounds of the present invention can be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds of the present invention can be formulated into an implant for subcutaneous administration. In addition, the compound of the present invention can be administered transdermally. For parenteral administration, the chosen dosage form should provide the animal with 0.01 mg / kg to 100 mg / kg of animal body weight per day of the compound of the present invention.

[0293] The compounds of the present invention can also be applied to animals in the form of dips, powders, collars, medallions, sprays, shampoos, pour-over formulations and emulsions in ointments or oil-in-water or water-in-oil formulations. For topical application, dips and sprays typically contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the compound of the present invention. In addition, the compounds of the present invention can be formulated as ear tags for animals, specifically quadrupeds such as cattle and sheep. Petition 870220032852, dated 04 / 18 / 2022, pp. 156 / 320 149 / 312

[0294] Suitable preparations are: Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pour-over formulations, gels; emulsions and suspensions for oral or dermal administration; semi-solid preparations; formulations in which the active compound is processed in an ointment base or in an oil-in-water or water-in-oil emulsion base; solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, cakes, capsules; aerosols and inhalants and shaped articles containing the compound.

[0295] Suitable injection compositions are prepared by dissolving the active ingredient in a suitable solvent and optionally adding additional ingredients such as acids, bases, buffer salts, preservatives and solubilizers.

[0296] The solutions are filtered and sterile filled.

[0297] Suitable solvents are physiologically tolerable solvents such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methylpyrrolidone, 2-pyrrolidone and mixtures thereof.

[0298] The active compounds may optionally be dissolved in physiologically tolerable vegetable or synthetic oils that are suitable for injection.

[0299] Suitable solubilizers are solvents that promote the dissolution of the active compound in the primary solvent or prevent its precipitation. Examples include polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester. Petition 870220032852, dated 04 / 18 / 2022, page 157 / 320 150 / 312

[0300] Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic esters and n-butanol.

[0301] Oral solutions are administered directly. Concentrates are administered orally before dilution to the concentration used. Oral solutions and concentrates are prepared according to the state of the art and, as described above for injection solutions, sterile procedures are not required.

[0302] Solutions for use on the skin are poured, spread, rubbed, sprayed or sprinkled.

[0303] Solutions for use on the skin are prepared according to the state of the art and, in accordance with what is described for injection solutions, sterile procedures are not required.

[0304] Suitable additional solvents are polypropylene glycol, phenyl ethanol, phenoxyethanol, esters such as ethyl or butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ether, for example, dipropylene glycol monomethyl ether, ketones such as acetone, methyl ethyl ketone, aromatic hydrocarbons, vegetable and synthetic oils, dimethylformamide, dimethylacetamide, transcutol, solquetal, propylene carbonate and mixtures thereof.

[0305] It may be advantageous to add thickeners during preparation. Suitable thickeners are inorganic thickeners such as bentonites, colloidal silicic acid, aluminum monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates.

[0306] Gels are applied or spread on the skin or introduced into body cavities. Gels are prepared Petition 870220032852, dated 04 / 18 / 2022, page 158 / 320 151 / 312 dealing with solutions that have been prepared as described in the case of injection solutions with sufficient thickener to produce a transparent material that has a consistency similar to ointment. The thickeners used are those specified above.

[0307] Pour formulations are poured or sprayed onto limited areas of skin, where the active compound penetrates the skin and acts systemically. Pour formulations are prepared by dissolving, suspending, or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. Where appropriate, other excipients such as colorants, bioabsorbent substances, antioxidants, light stabilizers, and adhesives are added.

[0308] Suitable solvents which are, for example, water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkyl esters of alkylene glycol such as dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, ketones such as acetone, methyl ethyl ketone, cyclic carbonates such as propylene carbonate, ethylene carbonate, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, n-alkylpyrrolidones such as methylpyrrolidone, n-butylpyrrolidone or n-octylpyrrolidone, N-methylpyrrolidone, 2-pyrrolidone, 2,2dimethyl-4-oxy-methylene-1,3-dioxolane or glycerol formal.

[0309] Suitable colorants are, for example, all colorants permitted for use in animals and which can be Petition 870220032852, dated 04 / 18 / 2022, page 159 / 320 152 / 312 dissolved or suspended.

[0310] Suitable absorption-promoting substances are, for example, dimethyl sulfoxide, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and copolymers thereof with polyethers, fatty acid esters, triglycerides or fatty alcohols.

[0311] Suitable antioxidants are, for example, sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylated hydroxytoluene, butylated hydroxyanisole or tocopherol.

[0312] Suitable light stabilizers, for example, novantisolic acid. Suitable adhesives are, for example, cellulose derivatives, starch derivatives, polyacrylates or natural polymers such as alginates, gelatin. Emulsions can be administered orally, dermally or as injections. Emulsions are either water-in-oil or oil-in-water.

[0313] They are prepared by dissolving the active compound in either the hydrophobic or hydrophilic phase and by homogenizing the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorbents, preservatives, antioxidants, light stabilizers, viscosity enhancers. Suitable hydrophobic phases (oils) are:

[0314] Liquid paraffin, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic / capric triglyceride, triglyceride mixture with vegetable fatty acids of chain length C1-C12 or other acids Petition 870220032852, dated 04 / 18 / 2022, pp. 160 / 320 153 / 312 specially selected natural fats, partial glyceride mixtures of saturated or unsaturated fatty acids that possibly also contain hydroxyl groups, mono- and diglycerides of Cs-do fatty acids, fatty acid esters such as ethyl stearate, di-nbutyryl adipate, hexyl laurate, dipropylene glycol perlagonate, esters of a medium-chain branched fatty acid with C16-C18 chain-length saturated fatty alcohols, isopropyl myristate, isopropyl palmitate, caprylic / capric acid esters of C12-C18 chain-length saturated fatty alcohols, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, fatty acid esters waxy, such as synthetic duck coccygeal gland fat, dibutyl phthalate, diisopropyl adipate and ester mixtures related to the latter, fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol,Suitable hydrophilic phases include: water, alcohols such as propylene glycol, glycerol, sorbitol, and mixtures thereof. Other suitable hydrophilic phases include: oleyl alcohol and fatty acids such as oleic acid and mixtures thereof.

[0315] Suitable emulsifiers are, for example, nonionic surfactants, for example, polyethoxylated castor oil, polyethoxylated sorbitan monooleate, sorbitan monostearate, glyceryl monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether; ampholytic surfactants such as disodium N-lauryl-p-iminodipropionate or lecithin.

[0316] Suitable anionic surfactants are, for example, sodium lauryl sulfate, fatty alcohol ether sulfates, Petition 870220032852, dated 04 / 18 / 2022, page 161 / 320 154 / 312 monoethanolamine salt of ether or orthophosphoric acid of mono / dialkyl polyglycol; suitable cation-active surfactants are cetyltrimethylammonium chloride.

[0317] Suitable auxiliaries are, for example, substances that increase viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, methyl vinyl ether and maleic anhydride copolymers, polyethylene glycols, waxes, colloidal silicic acid or mixtures of the substances mentioned.

[0318] Suspensions can be administered orally or topically / dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with the addition of other excipients such as wetting agents, colorants, bioabsorption enhancers, preservatives, antioxidants, light stabilizers.

[0319] Liquid suspending agents are all homogeneous solvents and solvent mixtures.

[0320] Suitable wetting agents (dispersants) are the emulsifiers provided above.

[0321] Other auxiliaries that may be mentioned as those mentioned above.

[0322] Semi-solid preparations can be administered orally or topically / dermally. They differ from the suspensions and emulsions described above only in their higher viscosity.

[0323] For the production of solid preparations, the active compound is mixed with suitable excipients, if Petition 870220032852, dated 04 / 18 / 2022, page 162 / 320 155 / 312 appropriate, with the addition of auxiliaries, and placed in the desired shape.

[0324] All suitable excipients are physiologically tolerable solid inert substances. Those used are inorganic and organic substances. Inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, bicarbonates, aluminum oxides, aluminum oxide, silicic acids, clayey earths, precipitated or colloidal silicas, or phosphates. Organic substances are, for example, sugar, cellulose, foods and feeds such as milk powder, animal feed, animal bran, pelleted foods and leftovers, starches.

[0325] Suitable auxiliaries are preservatives, antioxidants and / or colorants that have been mentioned above.

[0326] Other suitable auxiliaries are lubricants and glidants such as magnesium stearate, stearic acid, talc, bentonites, substances that promote disintegration such as starch or cross-linked polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyrrolidone and dry binders such as microcrystalline cellulose.

[0327] In general, parasiticidally effective amount means the amount of the active ingredient required to achieve an observable growth effect, including effects of necrosis, death, retardation, prevention and removal, destruction or otherwise decreasing the occurrence and activity of the target organism. The parasiticidally effective amount may vary for the various compounds / compositions used in the present invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions as an effect Petition 870220032852, dated 04 / 18 / 2022, page 163 / 320 156 / 312 and desired parasiticidal duration, target species, application method and the like. The compositions that can be used in the present invention generally comprise from about 0.001 to 95% of the compound of the present invention.

[0328] In general, it is favorable to apply the compounds of the present invention in total amounts of 0.5 mg / kg to 100 mg / kg per day, preferably 1 mg / kg to 50 mg / kg per day. Ready-to-use preparations contain the compounds that act against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 percent by weight, preferably 0.1 to 65 percent by weight, more preferably 1 to 50 percent by weight, most preferably 5 to 40 percent by weight. Preparations that are diluted before use contain the compounds that act against ectoparasites in concentrations of 0.5 to 90 percent by weight, preferably 1 to 50 percent by weight. Furthermore, the preparations comprise the compounds of the present invention against endoparasites at concentrations of 10 ppm to 2 percent by weight, preferably from 0.05 to 0.9 percent by weight, and most specifically, preferably from 0.005 to 0.25 percent by weight.

[0329] In one embodiment, the compositions comprising the compounds of the present invention are applied dermally / topically.

[0330] In another embodiment, topical application is carried out in the form of shaped articles containing the compound, such as collars, medallions, earrings, bands for fixing to body parts and adhesive tapes and sheets.

[0331] In general, it is advantageous to apply solid formulations that release compounds of the present invention in Petition 870220032852, dated 04 / 18 / 2022, page 164 / 320 157 / 312 total amounts of 10 mg / kg to 300 mg / kg, preferably 20 mg / kg to 200 mg / kg, with maximum preference, 25 mg / kg to 160 mg / kg of body weight of the treated animal over three weeks.

[0332] For the preparation of shaped articles, thermoplastics and flexible plastics as well as elastomers and thermoplastic elastomers are used. Suitable plastics and elastomers are polyvinyl resins, polyurethane, polyacrylate, epoxy resins, cellulose, cellulose derivatives, polyamides and polyester that are sufficiently compatible with the compounds of the present invention. A detailed list of plastics and elastomers as well as preparation procedures for shaped articles is provided, for example, in document WO 2003 / 086075. Response from a positive culture:

[0333] The compounds of the present invention can not only effectively control insect and mite pests but also show positive crop response such as plant growth enhancement effects such as enhanced root growth, enhanced tolerance to drought, high salt content, high temperature, cold, freezing or light radiation, enhanced flowering, enhanced nutrient utilization (such as nitrogen assimilation), enhanced quality plant product, increased farmer productivity, enhanced resistance to fungi, insects, pests and the like, resulting in higher yields. CHEMICAL EXAMPLES:

[0334] The following examples present the manner and process for producing compounds of the present invention without Petition 870220032852, dated 04 / 18 / 2022, page 165 / 320 158 / 312 being a limitation of the same and include the best method contemplated by the inventors to carry out the invention. Example 1: Synthesis of 2-(1-(3,5-dichlorophenyl)-2(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)3H-imidazo[4,5-b]pyridine (Compound no. 1): a) Step-1: 1-(2-Ethoxy-2-oxoethyl)pyridin-1-io:

[0335] To a stirred solution of pyridine (10.2 ml, 126 mmol) in acetonitrile (10 ml), ethyl 2-bromoacetate (15.4 ml, 139 mmol) was added, and the reaction mixture was heated under reflux for 18 h. After completion of the reaction, the reaction mixture was allowed to cool to 25 °C. The precipitate then obtained was filtered to obtain 1-(2-ethoxy-2-oxoethyl)pyridin-1-io (20 g, 120 mmol, 95% yield). 1H-NMR (400 MHz, DMSO-d6) δ 9.09-9.11 (m, 2H), 8.70-8.74 (m, 1H), 8.25 (dd, J = 7.9, 6.7 Hz, 2H), 5.73 (s, 2H), 4.22 (q, J = 7.1 Hz, 2H), 1.21 (t, J = 7.1 Hz, 3H); ESI MS (m / z) 166.20 (MH)+. b) Step-2: Ethyl 2-Fluoroindolizine-3-carboxylate:

[0336] To a stirred solution of 1-(2-ethoxy-2-oxoethyl)pyridin-1-io (8 g, 48.1 mmol) in N,N-dimethylformamide (80 ml), 2,2-difluorovinyl 4-methylbenzenesulfonate (7.9 g, 33.7 mmol), potassium carbonate (6.7 g, 48.1 mmol) and triethylamine (6.7 ml, 48.1 mmol) were added. The reaction mixture was heated to 70 °C for 12 h. After completion of the reaction, the reaction mixture was cooled to 25 °C. Water (150 ml) was added to the above reaction mixture and extracted twice with ethyl acetate (300 ml). The combined ethyl acetate layers were washed with brine (100 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. Petition 870220032852, dated 04 / 18 / 2022, page 166 / 320 159 / 312 The crude product was purified by flash chromatography on a silica gel column using ethyl acetate in hexane as an eluent to obtain ethyl 2-fluoroindolizine-3-carboxylate (4.2 g, 20.3 mmol, 42% yield). 1H-NMR (400 MHz, DMSO-d6) δ 9.29 (dq, J = 7.2, 1.0 Hz, 1H), 7.51-7.65 (m, 1H), 7.23-7.27 (m, 1H), 6.72-7.08 (m,1H), 6.27-6.50 (m, 1H), 4.33 (q, J = 7.1 Hz, 2H), 1.34 (t, J = 7.1Hz, 3H); ESI MS (m / z) 208.20 (MH)+. c) Step-3: 2-Fluoro-N-(2-(methylamino)-5-(trifluoromethyl)pyridin-3-yl)indolizine-3-carboxamide:

[0337] To a stirred solution of potassium tert-butoxide (1.2 g, 10.9 mmol) in N,N-dimethylformamide (5 ml), a solution of ethyl 2-fluoroindolizine-3-carboxylate (0.9 g, 4.4 mmol) and N-2-methyl-5-(trifluoromethyl)pyridine-2,3diamine (1 g, 5.2 mmol) in N,N-dimethylformamide (5 ml) was added at 0 °C. The reaction mixture was stirred at 25 °C for 2 h. After completion of the reaction, tetrahydrofuran was removed under reduced pressure to obtain the crude product, which was absorbed in water (25 ml) and extracted with ethyl acetate (75 ml). The ethyl acetate layer was washed with brine (50 ml) and water (50 ml), dried over anhydrous sodium sulfate, and concentrated to obtain the crude product. The crude product was purified by silica gel column chromatography using 40% ethyl acetate in hexane to generate 2-fluoro-N-(2-(methylamino)-5-(trifluoromethyl)pyridin-3-yl)indolizine-3-carboxamide (550 mg, 1.6 mmol, 36% yield).1H-NMR (400 MHz, DMSO-d6) δ 9.38 (dd, J = 7.1, 0.7 Hz, 1H), 8.75 (d, J = 4.6 Hz, 1H),. 8.30 (t, J = 1.1 Hz, 1H), 7.51–7.72 (m, 2H), 7.17–7.21 (m, 1H), 6.94–7.05 (m, 2H), 6.55 (s, 1H), 2.84–2.89 (d, J = 4.6). Petition 870220032852, 4 / 18 / 2022, p. 167 / 3 160 / 3 Hz, 3H); ESI MS (m / z) 352.95 (MH)+. d) Stage-4: 2-(2-Fluoroindolizin-3-yl)-3-methyl-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridine:

[0338] A mixture of 2-fluoro-N-(2-(methylamino)-5(trifluoromethyl)pyridin-3-yl)indolizine-3-carboxamide (1.4 g, 4 mmol), p-toluenesulfonic acid monohydrate (2.3 g, 11.9 mmol) in N-methyl-2-pyrrolidone (15 ml) was irradiated in a microwave oven at 150 °C for 1 hour under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was cooled to 25 °C. Water (100 ml) was added to the above reaction mixture followed by extraction with ethyl acetate (200 ml). The ethyl acetate layer was washed with water (50 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash chromatography on a silica gel column using 20% ​​ethyl acetate in hexane as an eluent to obtain 2-(2-fluoroindolizin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (830 mg, 2.5 mmol, 62% yield). 1H-NMR (400 MHz, DMSO-d6) δ 9.12 (dd, J = 7.1, 0.7 Hz, 1H), 8.78-8.82 (m, 1H); ESI MS (m / z) 335 (MH)+. e) Step-5: 2-(2-(Ethylsulfonyl)indolizin-3-yl)-3-methyl- 6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine:

[0339] To a stirred solution of 2-(2-fluoroindolizin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (830 mg, 2.5 mmol) in dry N,N-dimethylformamide (10 ml), sodium hydride (149 mg, 3.7 mmol) was added at 0 °C, and the reaction mixture was stirred for 30 minutes. The Petition 870220032852, dated 04 / 18 / 2022, page 168 / 320 161 / 312 ethanethiol (0.4 ml, 5 mmol) was added to the above reaction mixture by drop at 0 °C, and the reaction mixture was heated to 60 °C for 1 hour. After completion of the reaction, the reaction mixture was cooled to 25 °C. Water (50 ml) was added to the reaction mixture followed by extraction with ethyl acetate (150 ml). The ethyl acetate layer was washed with water (50 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash chromatography on a silica gel column using ethyl acetate in hexane as an eluent to obtain 2-(2-(ethylthio)indolizin3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (730 mg, 1.94 mmol, 78% yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.83 (q, J = 0.9Hz, 1H), 8.59-8.60 (m, 1H),8.43 (dd, J = 7.1, 0.7Hz, 1H), 7.57 (dd, J = 7.8, 1.2Hz, 1H), 7.00 (ddd, J = 9.0, 6.6, 1.0 Hz, 1H), 6.81 (s, 1H),6.72 (td, J = 6.9, 1.2 Hz, 1H), 3.89(s, 3H), 2.90-2.96 (q, J = 7.1 Hz, 2H), 1.19 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 377.05 (MH)+. f) Step-6: 2-(2-(Ethylsulfonyl)indolizin-3-yl)-3-methyl- 6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine:

[0340] To a solution of 2-(2-(ethylthio)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (200 mg, 0.5 mmol) in dichloromethane (3 ml), m-chloroperbenzoic acid (306 mg, 1.1 mmol) was added in portions at 0-5 °C. The reaction mixture was stirred at 25 °C for 2 h. After completion of the reaction, the reaction mixture was diluted with aqueous sodium thiosulfate solution and extracted with dichloromethane (150 ml). The dichloromethane layer was washed with a saturated aqueous sodium bicarbonate solution. Petition 870220032852, dated 04 / 18 / 2022, page 169 / 320 162 / 312 dried in anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash chromatography on a silica gel column using 40% ethyl acetate in hexane as an eluent to obtain 2-(2-(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (150 mg, 0.4 mmol, 69% yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.91 (t, J = 1.0 Hz, 1H), 8.70 (d, J = 1.5 Hz, 1H), 8.14 (dd, J = 7.1, 1.0 Hz, 1H), 7.71-7.91 (m, 1H), 7.11-7.16 (m, 2H), 6.88-6.91 (m, 1H), 3.7 (s, 3H), 3.39 (q, J = 7.1 Hz, 2H), 1.15 (t, J = 7.1 Hz, 3H); ESI MS (m / z) 409 (MH)+. g) Step-7: 2-(1-Bromo-2-(ethylsulfonyl)indolizin-3-yl)- 3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine:

[0341] To a stirred solution of 2-(2(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)3H-imidazo[4,5-b]pyridine (185 mg, 0.45 mmol) in dichloromethane (2 ml), N-bromosuccinimide (89 mg, 0.5 mmol) was added at 0 °C, and the reaction mixture was stirred at °C for 30 minutes. After completion of the reaction, the reaction mixture was diluted with water (20 ml) and extracted three times with dichloromethane (50 ml). The combined dichloromethane layers were washed with brine (100 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash chromatography on a silica gel column using 30% ethyl acetate in hexane to obtain 2-(1-bromo-2-(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)3H-imidazo[4,5-b]pyridine (160 mg, 0.3 mmol, 72% yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.90 (d, J = 1.8 Hz, 1H), 8.69 (d, J = 1.8 Hz, 1H), 8.11 (d, J = 7.3 Hz, 1H), Petition 870220032852, of 18 / 04 / 2022, p. 170 / 320 163 / 312 7.68 (d, J = 9.2 Hz, 1H), 7.24 (dd, J = 9.2, 6.7 Hz, 1H), 6, 90-6, 94 (m, 1H),3.70 (s, 3H), 3.36-3.46 (m, 2H), 1.12 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 486, 85, 489, 05 [(MH)+Br79.81]. h) Step-8: 2-(1-(3,5-Dichlorophenyl)-2(ethylsulfonyl)indolizine-3-yl)-3-methyl-6-(trifluoromethyl)3H-imidazo[4,5-b]pyridine:

[0342] A solution of 2-(1-bromo-2(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)3H-imidazo[4,5-b]pyridine (110 mg, 0.2 mmol) and (3,5-dichlorophenyl)boronic acid (43.1 mg, 0.2 mmol) in a mixture of 1,4-dioxane (2 ml) and water (0.2 ml), sodium carbonate (71.8 mg, 0.7 mmol) and tetracis(triphenylphosphine)palladium(0) (13 mg, 0.01 mmol) were added. The reaction mixture was completely deoxygenated by subjecting it to vacuum / nitrogen cycles three times and was heated in a microwave oven at 110 °C for 1.5 h. After the reaction was complete, the reaction mixture was cooled to 25 °C and filtered through a celite block. The filtrate was concentrated under reduced pressure, and the crude product was purified by flash chromatography on a silica gel column using ethyl acetate in hexane as an eluent to obtain 2-(1-(3,5-dichlorophenyl)-2-(ethylsulfonyl)indolizin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (73 mg, 0.1 mmol, 58% yield).1H-NMR (400 MHz, DMSO-d6) δ 8.92 (t, J = 2.2 Hz, 1H), 8.71 (t, J = 2.2 Hz, 1H), 8.15-8.17 (m, 1H),. 7.68-7.74 (m, 3H), 7.52-7.55 (m, 1H), 7.16-7.20 (m,1H), 6.93-6.99 (m, 1H), 3.79 (s, 3H), 3.05 (dtd, J = 63.8,14.5, 7.3 Hz, 2H), 0.89-1.1 (m, 3H); ESI-MS(m / z) 553.90, 554.90 [(MH) + Cl35,37]. Example 2: Synthesis of 2-(2-(ethylsulfonyl)imidazo[1,2 Petition 870220032852, dated 04 / 18 / 2022, page 171 / 320 164 / 312 a]pyridin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5b]pyridine (Compound no. 2): a) Step-1: 2-(2-Iminopyridin-1(2H)-yl)acetic acid:

[0343] To a stirred solution of 2-chloroacetic acid (4.0 g, 42.3 mmol) in water (10 ml), triethylamine (6.8 ml, 48.7 mmol) was added dropwise at 25 °C. After stirring for 10 min, pyridin-2-amine (4.8 g, 50.8 mmol) was added, and the resulting brown solution was heated at 90 °C for 5 h. After cooling to 25 °C, ethanol (20 ml) was added, and the resulting suspension was stirred at 5 °C for h. The precipitate was collected by filtration and washed with cold ethanol (30 ml) to obtain 2-(2-iminopyridin-1(2H)-yl)acetic acid (4.2 g, 28 mmol, 65% yield).1H- NMR (400 MHz, DMSO-d6) δ 8.11 (s, 1H), 7.79-7.91 (m, 2H), 6.98 (d, J = 7.8 Hz, 1H), 6.82 (s, 1H), 4.44 (s, 2H); ESI MS (m / z) 152.95 (MH)+. b) Step-2: 2-Chloroimidazo[1,2-a]pyridine:

[0344] To a stirred solution of 2-(2-iminopyridin-1(2H)-yl)acetic acid (4.2 g, 27.6 mmol) in toluene (50 ml), phosphorous oxychloride (7.7 ml, 83 mmol) was added dropwise, and the resulting reaction mixture was heated to 100 °C for 16 h. After completion of the reaction, the reaction mixture was cooled to 25 °C. Cold water (500 ml) was added, and the solution was stirred for 15 minutes. The aqueous layer was neutralized with 10% aqueous sodium hydroxide solution and extracted with dichloromethane (250 ml). The combined dichloromethane layers were washed with water (100 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash column chromatography. Petition 870220032852, dated 04 / 18 / 2022, page 172 / 320 165 / 312 silica gel using ethyl acetate hexane as eluent to generate 2-chloroimidazo[1,2-a]pyridine (3.2 g, 21 mmol, 76% yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.50 (dt, J = 6.8, 1.2 Hz, 1H), 8.05-8.08 (m, 1H), 7.54 (dq, J = 9.1, 0.9 Hz, 1H), 7.33 (ddd, J = 9.2, 6.8, 1.3 Hz, 1H), 6.99 (td, J = 6.8, 1.2 Hz, 1H); ESI MS (m / z) 152.90 (MH)+. c) Step-3: Ethyl 2-Chloroimidazo[1,2-a]pyridine-3-carboxylate:

[0345] To a stirred solution of 2-chloroimidazo[1,2a]pyridine (0.5 g, 3.3 mmol) in tetrahydrofuran (10 ml), n-butyllithium (1.8 ml, 3.6 mmol) was added dropwise at -78 °C. After stirring for 30 minutes, ethyl chlorocarbonate (0.36 g, 3.3 mmol) in tetrahydrofuran (10 ml) was added to the reaction mixture at the same temperature. The reaction mixture was stirred for 1 hour at -78 °C and subsequently at 25 °C for another hour. After completion of the reaction, the mixture was rapidly cooled by adding saturated ammonium chloride solution (20 ml) and extracted twice with ethyl acetate (100 ml). The combined layers of ethyl acetate were washed with water (100 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product.The crude product was purified by silica gel flash chromatography using 30% ethyl acetate in hexane as eluent to generate ethyl 2-chloroimidazo[1,2a]pyridine-3-carboxylate (0.5 g, 2.2 mmol, 68% yield). 1H-NMR (400 MHz, DMSO-d6) δ 9.24 (dt, J = 6.9,. 1.2 Hz, 1H), 7.77 (dt, J = 9.0, 1.2 Hz, 1H), 7.66 (ddd, J = 9.0, 6.9, 1.3 Hz, 1H), 7.31 (td, J = 6.9, 1.3 Hz, 1H), 4.35 (q, J = 7.1 Hz, 2H), 1.45 (t, J = 6.8 Hz, 3H); ESI MS (m / z) Petition 870220032852, dated 04 / 18 / 2022, page 173 / 320 166 / 312 224.90 (MH)+. d) Step-4: 2-Chloro-N-(2-(methylamino)-5-(trifluoromethyl)pyridin-3-yl)imidazo[1,2-a]pyridine-3carboxamide:

[0346] To a stirred solution of potassium tert-butoxide (0.5 g, 4.5 mmol) in tetrahydrofuran (10 ml), the solution of ethyl 2-chloroimidazo[1,2-a]pyridine-3-carboxylate (0.5 g, 2.2 mmol) and N-2-methyl-5-(trifluoromethyl)pyridine-2,3-diamine (0.4 g, 2.2 mmol) in tetrahydrofuran (10 ml) was added at 0 °C. The reaction mixture could be stirred at 25 °C for 1 hour. After the reaction was complete, the tetrahydrofuran was removed under reduced pressure to obtain the crude product, which was absorbed in water (20 ml) and extracted with dichloromethane (75 ml). The dichloromethane layer was washed with brine (50 ml) and water (50 ml), dried over anhydrous sodium sulfate, and concentrated to obtain the crude product. The crude product was purified by silica gel column chromatography using 40% ethyl acetate in hexane to generate 2-chloro-N-(2-(methylamino)-5(trifluoromethyl)pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide (0.45 g, 1.2 mmol, 55% yield).1H-NMR (400 MHz, DMSO-d6) δ 9.16–9.22 (m, 2H), 8.34 (q, J = 1.1 Hz,. 1H), 7.59–7.76 (m, 3H), 7.24 (td, J = 7.0, 1.4 Hz, 1H), 7.03 (q, J = 4.6 Hz, 1H), 2.90 (d, J = 4.6 Hz, 3H); ESI MS (m / z) 369, 85 (MH)+. e) Stage-5: 2-(2-Chloroimidazo[1,2-a]pyridin-3-yl)-3-methyl6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine:

[0347] A mixture of 2-chloro-N-(2-(methylamino)-5(trifluoromethyl)pyridin-3-yl)imidazo[1,2-a]pyridine-3carboxamide (0.25 g, 0.68 mmol), mono-hydrate of pPetition 870220032852, dated 18 / 04 / 2022, p. 174 / 3 167 / 312 toluenesulfonic acid (0.39 g, 2.03 mmol) in N-methyl-2-pyrrolidone (10 ml) was irradiated in a microwave oven at 150 °C for 2 h under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was cooled to 25 °C. Water (50 ml) was added to the above reaction mixture followed by extraction with ethyl acetate (150 ml). The ethyl acetate layer was washed with water (50 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash chromatography on a silica gel column using 40% ethyl acetate in hexane as an eluent to obtain 2-(2-chloroimidazo[1,2-a]pyridin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (0.2 g, 0.5 mmol, 76% yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.89 (q, J = 0.9 Hz, 1H), 8.68-8.73 (m, 2H), 7.79 (dt, J = 9.0, 1.1 Hz, 1H), 7.60 (ddd, J = 9.0, 7.0, 1.3 Hz, 1H), 7.20 (td, J = 7.0, 1.2 Hz, 1H), 3.92 (s, 3H); ESI MS (m / z) 352.05 (MH)+. f) Step-6: 2-(2-(Ethylthio)imidazo[1,2-a]pyridin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine:

[0348] To a stirred solution of 2-(2-chloroimidazo[1,2a]pyridin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5b]pyridine (0.3 g, 0.9 mmol) in dry N,N-dimethylformamide (5 ml), sodium hydride (0.1 g, 1.7 mmol) was added at 0 °C, and the reaction mixture was stirred for 30 minutes, and ethanethiol (0.1 ml, 1.3 mmol) was added to the above reaction mixture at 0 °C, and the reaction mixture was heated to 60 °C for 2 h. After completion of the reaction, the reaction mixture was cooled to 25 °C. Cold water (150 ml) was added to the reaction mixture, and the resulting precipitate was removed by filtration, washed with water (10 ml) and dried under vacuum to Petition 870220032852, dated 04 / 18 / 2022, page 175 / 320 168 / 312 obtain crude product. The crude product was purified by flash chromatography on a silica gel column using 40% ethyl acetate in hexane as an eluent to obtain 2-(2-(ethylthio)imidazo[1,2-a]pyridin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (0.25 g, 0.7 mmol, 78% yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.85 (t, J = 1.0 Hz, 1H), 8.63-8.65 (m, 2H), 7.74 (dt, J = 9.0, 1.1 Hz, 1H), 7.50 (ddd, J = 9.0, 6.8, 1.2 Hz, 1H), 7.08 (td, J = 6.8, 1.2 Hz, 1H), 3.90 (s, 3H), 3.25 (q, J = 7.3 Hz, 2H), 1.23 (t, J = 6.8 Hz, 3H); ESI MS (m / z) 378.10 (MH)+. g) Step-7: 2-(2-(Ethylsulfonyl)imidazo[1,2-a]pyridin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5b]pyridine:

[0349] To a solution of 2-(2-(ethylthio)imidazo[1,2a]pyridin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5b]pyridine (0.2 g, 0.5 mmol) in dichloromethane (5 ml), m-chloroperbenzoic acid (0.3 g, 1 mmol) was added in portions at 0-5 °C. The reaction mixture was stirred at 25 °C for 2 h. After the reaction was complete, the reaction mixture was diluted with aqueous sodium thiosulfate solution and extracted with dichloromethane (15 ml). The dichloromethane extract was washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash chromatography on a silica gel column using 35% ethyl acetate in hexane as an eluent to obtain 2-(2-(ethylsulfonyl)imidazo[1,2a]pyridin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5b]pyridine (0.1 g, 0.3 mmol, 67% yield).1H-NMR (400 MHz, DMSO-d6) δ 8.93–8.93 (m, 1H), 8.73 (dd, J = 2.1, 0.6 Petition 870220032852, of 18 / 04 / 2022, p. 176 / 320 169 / 312 Hz, 1H), 8.47 (dt, J = 7.0, 1.1 Hz, 1H), 7.94 (dt, J = 9.2, 1.1 Hz, 1H), 7.68 (ddd, J = 9.0, 6.8, 1.2 Hz, 1H), 7.22 (td, J = 6.9, 1.1 Hz, 1H), 3.86 (s, 3H), 3.49-3.52 (q, J = 6.8 Hz, 2H), 1.15-1.24 (t, J = 7.6 Hz, 3H); ESI MS (m / z) 409.95 (MH)+. Example 3: Synthesis of 2-(8-(3,5-dichlorophenyl)-2(ethylsulfonyl)indolizine-3-yl)-3-methyl-6-(trifluoromethyl)3H-imidazo[4,5-b]pyridine (Compound No. 6): a) Step-1: 3-Bromo-1-(2-ethoxy-2-oxoethyl)pyridin-1-io:

[0350] To a stirred solution of 3-bromopyridine (12.4 ml, 127 mmol) in acetonitrile (200 ml), ethyl 2-bromoacetate (15.5 ml, 139 mmol) was added, and the reaction mixture was heated under reflux for 16 h. After the reaction was complete, the reaction mixture was cooled to 25 °C, and the resulting precipitate was filtered to obtain 3-bromo-1-(2-ethoxy-2-oxoethyl)pyridin-1-io (30 g, 122 mmol, 97% yield). 1H-NMR (400 MHz, chloroform-D) δ 9.56 (m, 1H), 9.35 (s, 1H), 8.62 (d, J = 8.3 Hz, 1H), 6.28 (s, 2H), 4.36 (q, J = 7.1 Hz, 3H), 1.33-1.4 (t, J = 7.2 Hz, 3H); ESI MS (m / z) 243.85, 245, 85 [(MH)+Br79-81]. b) Step-2:6-Bromo-2-fluoroindolizine-3-ethyl carboxylate and 8-Bromo-2-fluoroindolizine-3-ethyl carboxylate:

[0351] To a stirred solution of 3-bromo-1-(2-ethoxy-2-oxoethyl)pyridin-1-io (3 g, 12.2 mmol) in N,N-dimethylformamide (80 ml), 2,2-difluorovinyl 4-methylbenzenesulfonate (1 g, 4.3 mmol), potassium carbonate (0.85 g, 6.1 mmol) and triethylamine (0.85 ml, 6.1 mmol) were added. The reaction mixture was heated to 70 °C for 16 h. After completion of the reaction, the reaction mixture was Petition 870220032852, dated 04 / 18 / 2022, page 177 / 320 170 / 312 cooled to 25 °C. Water (50 ml) was added to the above reaction mixture, which was extracted twice with ethyl acetate (200 ml). The combined ethyl acetate layers were washed with brine (100 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative reverse-phase HPLC to obtain ethyl 6-bromo-2-fluoroindolizine-3-carboxylate (240 mg, 0.8 mmol, 14% yield) and ethyl 8-bromo-2-fluoroindolizine-3-carboxylate (160 mg, 0.56 mmol, 9%). i. Ethyl 6-Bromo-2-fluoroindolizine-3-carboxylate:

[0352] 1H-NMR (400 MHz, DMSO-d6) δ 9.37-9.47 (m, 1H), 7.63-7.71 (m, 1H), 7.35-7.41 (m, 1H), 6.58-6.69 (m, 1H), 4.35 (q, J = 7.1 Hz, 2H), 1.35 (t, J = 7.2 Hz, 3H); ESI MS (m / z) 286.05, 288.05 [(MH)+Br79.81]. ii Ethyl 8-Bromo-2-fluoroindolizine-3-carboxylate:

[0353] 1H-NMR (400 MHz, DMSO-d6) δ 9.28-9.40 (m, 1H), 7.58-7.64 (m, 1H), 6.97 (t, J = 7.2 Hz, 1H), 6.57 (d, J = 11.5 Hz, 1H), 4.33 (q, J = 7.2 Hz, 2H), 1.3 (t, J = 7.2 Hz, 3H); ESI MS (m / z) 286, 288 [(MH)+Br79, 81]. c) Step-3:8-Bromo-2-fluoro-N-(2-(methylamino)-5-(trifluoromethyl)pyridin-3-yl)indolizine-3-carboxamide:

[0354] The reaction involving ethyl 6-bromo-2-fluoroindolizine-3-carboxylate (2.1 g, 7.3 mmol) and N-2-methyl-5-(trifluoromethyl)pyridine-2,3-diamine (1 g, 5.23 mmol) as appropriate reagents following the same synthetic procedures described in step 3 of example 34 produced 8-bromo-2-fluoro-N-(2-(methylamino)-5-(trifluoromethyl)pyridine. Petition 870220032852, dated 18 / 04 / 2022, page 178 / 320 171 / 312 3-yl)indolizine-3-carboxamide (1.3 g, 3 mmol, 41% yield). 1H-NMR (400 MHz, chloroform-D) δ 9.62 (d, J = 7.0 Hz, 1H), 8.37 (d, J = 0.9 Hz, 1H), 7.72 (dd, J =6.7, 2.1 Hz, 1H), 7.46-7.52 (m, 1H), 7.33-7.38 (m, 1H), 6.75(t, J = 7.3 Hz, 1H), 6.49 (s, 1H), 5.13 (d, J = 4.3 Hz, 1H), 3.05-3.08 (d, J = 5.2 Hz, 3H); ESI MS (m / z) 430.75, 432.75 [(MH) + Br79,81]. d) Etapa-4: 2-(8-Bromo-2-fluoroindolizin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine:

[0355] A cycle involving 8-bromo-2-fluoro-N-(2(methylamino)-5-(trifluoromethyl)pyridin-3-yl)indolizine-3carboxamida (2.2 g, 5.10 mmol) and following the same synthetic process as described in stage 4 of Example 34 production 2-(8-bromo-2-fluoroindolizin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (1.8 g, 4.4 mmol, 85% yield). ESI MS (m / z) 412.70, 414.70 [(MH)+Br79.81]. e) Etapa-5: 2-(8-Bromo-2-(ethylthio)indolizin-3-yl)-3-methyl6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine:

[0356] 2-(8-Bromo-2-fluoroindolizin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (100 mg, 0.2 mmol) as a suitable starting material and following the same synthetic procedure as described in step 5 of Example 34 produced 2-(8-bromo-2-(ethylthio)indolizin-3-yl)3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (50 mg, 0.1 mmol, 45% yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.83 (d, J = 1.2 Hz, 1H), 8.61 (d, J = 1.5 Hz, 1H), 8.41 (d, J = 7.0 Hz, 1H), 7.33 (dd, J = 7.3, 0.6 Hz, 1H), 6.83 (d, J = 0.6 Hz, 1H), 6.66 (t, J = 7.2 Hz, 1H), 3.82 (s,3H), 2.98 (q, J = 7.3 Hz, 2H), 1.18 (q, J = 7.1 Hz, 3H); ESI MS Petition 870220032852, dated 04 / 18 / 2022, pp. 179 / 320 172 / 312 (m / z) 454.95, 456, 95 [(MH)+Br79' 81]. f) Step-6: 2-(8-Bromo-2-(ethylsulfonyl)indolizin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine:

[0357] The oxidation of 2-(8-bromo-2-(ethylthio)indolizin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (840 mg, 1.84 mmol) following the same synthetic procedure described in step 6 of Example 34 was produced 2-(8-bromo-2(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)3H-imidazo[4,5-b]pyridine pyridine (800 mg, 1.6 mmol, 89 % yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.89–8.93(m. 1H), 8.55–8.72 (m, 1H), 8.12–8.23 (m, 1H), 7.50–7.57(m, 1H), 7.11–7.26 (m, 1H), 6.75–6.85 (m, 1H), 3.72 (s,3H), 3.39- 3.51 (q, J = 6.8 Hz, 2H), 1.15 (t, J = 7.1 Hz, 3H); ESI MS (m / z) 487.05.489.05 [(MH)+Br79.81]. g) Step-7: 2-(8-(3,5-Dichlorophenyl)-2(ethylsulfonyl)indolizin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine:

[0358] The Suzuki coupling involving 2-(8-bromo-2(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)3H-imidazo[4,5-b]pyridine (150 mg, 0.31 mmol) and (3,5-dichlorophenyl)boronic acid (58.7 mg, 0.31 mmol) while following the same synthetic procedure described in step 7 of Example 34 yielded 2-(8-(3,5-dichlorophenyl)-2(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-Hz, 2H), 1,11 (t, J = 7.3 Hz, 3H);(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (65 mg, 0.1 mmol, 38% yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.93 (s, 1H), 8.73 (s, 1H), 8.22 (d, J = 7.1 Hz, 1H), 7.81 (s, 3H), 7.27 (d, J = 6.8 Hz, 1H), 6.99-7.13 (m, 2H), 3.73 (s, 3H), 3.40 (q, J = 7.2 Hz, 2H), 1.11 (t, J = 7.3 Hz, 3H); ESI-MS(m / z) 553, 15, 555, 15 [(MH)+Cl35.37]. Petition 870220032852, dated 04 / 18 / 2022, pages 180 / 320 173 / 312 Example 4: Synthesis of 2-(6-(3,5-dichlorophenyl)-2(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)3H-imidazo[4,5-b]pyridine (Compound no. 8):

[0359] The title compound was prepared starting at ethyl 8-bromo-2-fluoroindolizine-3-carboxylate as obtained in step 2 of example 42 and following the same sequence of steps 3-7 as described for the synthesis of 2-(8-(3,5-dichlorophenyl)-2-(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine yielded 2-(6(3,5-dichlorophenyl)-2-(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine. 1H-NMR (400 MHz, DMSO-d6) δ 8.92-8.93 (m, 1H), 8.71-8.71 (m, 1H), 8.55 (d, J = 0.7 Hz, 1H), 7.90-7.94 (m, 1H), 7.73-7.77 (m, 2H), 7.62 (m, 1H), 7.53 (dd, J = 9.4, 1.6 Hz, 1H), 7.01-7.28 (m, 1H), 3.75 (s, 3H), 3.33-3.42 (m, 2H), 1.15 (t, J = 6.2 Hz, 3H); ESI MS (m / z) 553.00, 555.00 [(MH)+Cl35, 37]. Example 5: Synthesis of 2-(2-(ethylthio)-5,7dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (Compound no. 9): a) Step-1: 2-(Ethylthio)-5,7-dimethylpyrazolo[1,5- a]ethyl pyrimidine-3-carboxylate:

[0360] To a stirred solution of ethyl 5-amino-3-(ethylthio)-1H-pyrazol-4-carboxylate (2 g, 9.3 mmol) [prepared according to the procedure described in Acta Chimica Sinica 2003, 63, 855; Organic & Biomolecular Chemistry, 2010, 8, 3394] and 2,4-pentanedione (1.15 ml, 11.15 mmol) in acetic acid (20 ml), two drops of concentrated sulfuric acid were added. The resulting mixture was heated to 50 °C for 15 minutes. After the reaction was complete, the reaction mixture was cooled to 25 °C. Water (5 ml) was added to Petition 870220032852, dated 04 / 18 / 2022, pp. 181 / 320 174 / 312 reaction mixture above, and the reaction mixture was extracted three times with ethyl acetate (10 ml). The combined ethyl acetate layers were dried over sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using 20% ​​ethyl acetate in hexane as an eluent to obtain ethyl 2(ethylthio)-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylate (2.0 g, 7.20 mmol, 77% yield). 1H-NMR (400 MHz, DMSO-d6) δ 7.04 (d, J = 0.7 Hz, 1H),4.25 (q, J = 7.1 Hz, 2H), 3.17 (q, J = 7.3 Hz, 2H), 2.67-2.83(m, 3H), 2.56 (d, J = 23.7 Hz, 3H), 1.36-1.53 ​​(m, 3H), 1.30(q, J = 6.9 Hz, 3H); ESI MS (m / z) 280.20 (MH)+. b) Step-2: 2-(ethylthio)-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid:

[0361] To a stirred suspension of ethyl 2-(ethylthio)-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylate (2.3 g, 8.2 mmol) in a mixture of ethanol (37.5 ml) and water (37.5 ml), lithium hydroxide monohydrate (5.18 g, 123.0 mmol) was added. The reaction mixture was stirred at 60 °C for 17 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to remove ethanol. The residue was treated with 1 N hydrochloric acid solution, and the resulting precipitate of 2-(ethylthio)-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid (88 mg, 0.35 mmol, 59% yield) was removed by filtration, washed with water (10 ml), and dried under vacuum. 1H-NMR (400 MHz, DMSO-d6) δ 12.16 (s, 1H), 7.02 (d, J = 0.7 Hz, 1H), 3.15 (q, J = 7.3 Hz, 2H), 2.67 (d, J = 0.9 Hz, 3H), 2.53 (s, 3H), 1.37 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 252.15 (MH)+. Petition 870220032852, dated 04 / 18 / 2022, page 182 / 320 175 / 312 c) Step-3: 2-(ethylthio)-5,7-dimethyl-N-(2-(methylamino)-5-(trifluoromethyl)pyridin-3yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide:

[0362] To a solution of 2-(ethylthio)-5,7dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid (500 mg, 2 mmol) in anhydrous N,N-dimethylformamide (27 ml), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5b]pyridinium 3-oxide hexafluorophosphate (HATU) (908 mg, 2.4 mmol) was added, and the reaction mixture was stirred at 0-5 °C for 15 minutes. Subsequently, N-2-methyl-5-(trifluoromethyl)pyridine-2,3diamine (761 mg, 4 mmol) and N,N-diisopropylethylamine (1 ml, mmol) were added to the above reaction mixture, and the reaction was heated at 100 °C for 16 h. After the reaction was complete, water (40 ml) was added to the reaction mixture, which was then extracted three times with ethyl acetate (30 ml). The combined ethyl acetate layers were dried over sodium sulfate and concentrated under reduced pressure to obtain the crude product.The crude product was purified by silica gel column chromatography using 40% ethyl acetate in hexane as an eluent to obtain 2(ethylthio)-5,7-dimethyl-N-(2-(methylamino)-5(trifluoromethyl)pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3carboxamide (510 mg, 1.20 mmol, 60% yield). 1H-NMR (400 MHz, DMSO-d6) δ 9.74 (s, 1H), 8.27 (d, J = 1.3 Hz, 1H). 8.05-8.07 (m, 1H), 7.14-7.28 (m, 1H), 6.80 (d, J = 4.9 Hz, 1H), 3.22 (q, J = 7.3 Hz, 2H), 2.92 (d, J = 4.6 Hz, 3H), 2.76 (d, J = 0.5 Hz, 3H), 2.64 (s, 3H), 1.41 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 425.20 (MH)+. d) Step-4: 2-(2-(ethylthio)-5,7-dimethylpyrazolo[1,5Petition 870220032852, dated 04 / 18 / 2022, page 183 / 320 176 / 312 a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine:

[0363] A mixture of 2-(ethylthio)-5,7-dimethyl-N-(2(methylamino)-5-(trifluoromethyl)pyridin-3-yl)pyrazolo[1,5a]pyrimidine-3-carboxamide (380 mg, 0.90 mmol), p-toluenesulfonic acid monohydrate (511 mg, 2.7 mmol) in N-methyl2-pyrrolidone (8 ml) was irradiated in a microwave oven at 150 °C for 1.5 h under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was allowed to cool to °C. Water (50 ml) was added to the above reaction mixture followed by extraction with ethyl acetate (50 ml). The ethyl acetate layer was washed with water (30 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash chromatography on a silica gel column using 40% ethyl acetate in hexane as an eluent to obtain 2-(2-(ethylthio)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (194 mg, 0.5 mmol, 53% yield).1H-NMR (400 MHz, CDCl3) δ 8.64 (d, J = 1.2 Hz, 1H), 8.31 (d, J = 1.5 Hz, 1H), 6.65 (d, J = 0.7 Hz, 1H), 4.02 (s, 3H), 3.29 (q, J = 7.4 Hz, 2H), 2.79 (d, J = 0.7 Hz, 3H), 2.57 (s, 3H), 1.46 (t, J = 7.3Hz, 3H); ESI MS (m / z) 407.10 (MH)+. Example 6: Synthesis of 2-(2-(ethylsulfonyl)-5,7dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (Compound no. 10):

[0364] A solution of 2-(2-(ethylthio)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (165 mg, 0.4 Petition 870220032852, dated 04 / 18 / 2022, page 184 / 320 177 / 312 mmol) in dichloromethane (8 ml), m-chloroperbenzoic acid (255 mg, 0.8 mmol) was added in portions at 0-5 °C. The reaction mixture was stirred at 25 °C for 5 h. After the reaction was complete, the reaction mixture was diluted with aqueous sodium thiosulfate solution and extracted with dichloromethane (20 ml). The dichloromethane layer was washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash chromatography on a silica gel column using 60% ethyl acetate in hexane as an eluent to obtain 2-(2-(ethylsulfonyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (92 mg, 0.2 mmol, 52% yield). 1H-NMR (400 MHz, DMSOd6) δ 8.84 (s, 1H), 8.61 (d, J = 2.0 Hz, 1H), 7.36 (d, J = 1.0 Hz, 1H), 3.78 (s, 3H), 3.73 (q, J = 7.3 Hz, 2H), 2.83 (s, 3H), 2.57 (s, 3H), 1.25 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 439.25 (MH)+. Example 7: Synthesis of 2-(2-(ethylthio)-7-(4fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (Compound No. 19): a) Step 1: Ethyl 2-(Ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5a]pyrimidine-3-carboxylate:

[0365] To a stirred solution of ethyl 3-amino-5-(ethylthio)-1H-pyrazol-4-carboxylate (1.9 g, 9 mmol) in acetic acid (65.4 ml), (E)-3-(dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-one (1.7 g, 9 mmol) was added, and the resulting mixture was heated at 50 °C for 2 h. After the reaction was complete, the acetic acid was removed under reduced pressure to obtain the crude product. The crude product was Petition 870220032852, dated 04 / 18 / 2022, pp. 185 / 320 178 / 312 purified by silica gel column chromatography using 30% ethyl acetate in hexane as an eluent to obtain ethyl 2-(ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5a]pyrimidine-3-carboxylate (2.2 g, 6.37 mmol, 71% yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.77 (d, J = 4.6 Hz, 1H), 8.20-8.25 (m, 2H), 7.44-7.49 (m, 2H), 7.42 (d, J = 4.6 Hz, 1H), 4.30 (q, J = 7.1 Hz, 2H), 3.09 (q, J = 7.3 Hz, 2H), 1.33 (dt, J = 15.6, 7.2 Hz, 6H); ESI MS (m / z) 346.30 (MH)+. b) Step 2: 2-(ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid:

[0366] To a stirred suspension of ethyl 2-(ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (2.2 g, 6.4 mmol) in a mixture of ethanol (30 ml) and water (30 ml), lithium hydroxide monohydrate (2.7 g, 63.7 mmol) was added. The reaction mixture was stirred at 60 °C for 2 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to remove ethanol. The residue was treated with 1 N hydrochloric acid solution, and the resulting precipitate of 2-(ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (1.6 g, 5 mmol, 79% yield) was removed by filtration, washed with water (10 ml), and dried under vacuum. 1H-NMR (400 MHz, DMSO-d6) δ 8.44 (d, J = 4.6 Hz, 1H), 8.28 (ddd, J = 12.1, 5.3, 3.2 Hz, 2H), 7.43-7.49 (m, 2H), 7.19 (d, J = 4.6 Hz, 1H), 3.00 (q, J = 7.3 Hz, 2H), 1.32 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 317.90 (M)+. c) Step 3: 2-(Ethylthio)-7-(4-fluorophenyl)-N-(2-(methylamino)-5-(trifluoromethyl)pyridin-3yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide: Petition 870220032852, dated 04 / 18 / 2022, pp. 186 / 320 179 / 312

[0367] To a suspension of 2-(ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (500 mg, 1.58 mmol) in anhydrous dichloromethane (15 ml), 2 drops of N,N-dimethylformamide were added, followed by the addition of oxalyl chloride (0.2 ml, 2.4 mmol), and the resulting reaction mixture was stirred at 25 °C for 4 h. The reaction mixture was evaporated under reduced pressure at a bath temperature of 60 °C. The resulting residue was dissolved in anhydrous dichloromethane (15 ml) and added dropwise at 0 °C to a stirred solution of N-2-methyl-5-(trifluoromethyl)pyridine-2,3-diamine (304 mg, 1.6 mmol) and triethylamine (0.9 ml, 6.6 mmol). The reaction mixture was stirred at 25 °C for 16 h. After the reaction was complete, water (40 ml) was added to the reaction mixture, which was then extracted three times with ethyl acetate (20 ml). The combined ethyl acetate layers were dried over sodium sulfate and concentrated under reduced pressure to obtain the crude product.The crude product was purified by silica gel column chromatography using 40% ethyl acetate in hexane as an eluent to obtain 2(ethylthio)-7-(4-fluorophenyl)-N-(2-(methylamino)-5(trifluoromethyl)pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (377 mg, 0.8 mmol, 49% yield). 1H-NMR (400 MHz, DMSO-d6) δ 9.51 (s, 1H), 8.85 (d, J = 4.6 Hz, 1H). 8.28-8.34 (m, 3H), 7.90 (d, J = 1.8 Hz, 1H), 7.49-7.53 (m, 3H), 6.92 (d, J = 4.6 Hz, 1H), 3.14 (q, J = 7.2 Hz, 2H), 2.89 (d, J = 4.6 Hz, 3H), 1.33-1.39 (m, 3H); ESI MS (m / z) 490.95 (M)+. d) Step 4: 2-(2-(Ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H- Petition 870220032852, dated 04 / 18 / 2022, page 187 / 320 180 / 312 imidazo[4,5-b]pyridine:

[0368] A mixture of 2-(ethylthio)-7-(4-fluorophenyl)-N(2-(methylamino)-5-(trifluoromethyl)pyridin-3yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (377 mg, 0.8 mmol), p-toluenesulfonic acid monohydrate (439 mg, 2.3 mmol) in N-methyl-2-pyrrolidone (8 ml) was irradiated in a microwave oven at 150 °C for 1.5 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was cooled to 25 °C. Water (50 ml) was added to the above reaction mixture followed by extraction with ethyl acetate (150 ml). The ethyl acetate layer was washed with water (50 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash chromatography on a silica gel column using 40% ethyl acetate in hexane as an eluent to obtain 2-(2-(ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (185 mg, 0.4 mmol, 51% yield).1H-NMR (400 MHz, DMSO-d6) δ 8.77 (q, J = 0.9 Hz, 1H), 8.75 (d, J = 4.4 Hz, 1H), 8.54-8.54 (m,. 1H), 8.29-8.33 (m, 2H), 7.49-7.53 (m, 2H), 7.43 (d, J = 4.6 Hz, 1H), 3.97 (s, 3H), 3.17 (q, J = 7.3 Hz, 2H), 1.36 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 473.00 (MH)+. Example 8: Synthesis of 2-(2-(ethylthio)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-c]pyridine (Compound no. 22): a) Step 1:2-ethyl(Ethylthio)pyrazolo[1,5-a]pyrimidine-3carboxylate:

[0369] To a stirred solution of ethyl 5-amino-3-(ethylthio)-1H-pyrazol-4-carboxylate (1.3 g, 6 mmol) in acid Petition 870220032852, dated 04 / 18 / 2022, pp. 188 / 320 181 / 312 acetic acid (38 ml), 3-(dimethylamino)acrolein (0.9 ml, 9.1 mmol) was added. The reaction mixture was stirred at 25 °C for 24 h. After the reaction was complete, the reaction mixture was neutralized using saturated aqueous sodium bicarbonate and extracted three times with ethyl acetate (20 ml). The combined ethyl acetate layers were dried over sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using % ethyl acetate in hexane as an eluent to obtain Ethyl 2-(ethylthio)pyrazolo[1,5-a]pyrimidine-3-carboxylate (0.9 g, 3.5 mmol, 57% yield). 1H-NMR (400 MHz, DMSOd6) δ 9.18 (dd, J = 6.9, 1.7 Hz, 1H), 8.74 (q, J = 1.9 Hz, 1H), 7.20 (dd, J = 7.0, 4.3 Hz, 1H), 4.27 (q, J = 7.1 Hz, 2H), 3.16 (q, J = 7.3 Hz, 2H), 1.37 (t, J = 7.3 Hz, 3H), 1.25-1.31 (m, 3H);ESI MS (m / z) 252.10 (MH)+. b) Step 2: 2-(ethylthio)pyrazolo[1,5-a]pyrimidine-3carboxylic acid:

[0370] To a stirred suspension of ethyl 2-(ethylthio)pyrazolo[1,5-a]pyrimidine-3-carboxylate (0.9 g, 3.5 mmol) and a mixture of ethanol (50 ml) and water (50 ml) was added lithium hydroxide monohydrate (1.45 g, 34.6 mmol). The reaction mixture was stirred at 60 °C for h. After the reaction was complete, the reaction mixture was concentrated under reduced pressure to remove ethanol. The residue was treated with 1 N hydrochloric acid solution, and the resulting precipitate of 2-(ethylthio)pyrazolo[1,5a]pyrimidine-3-carboxylic acid (0.6 g, 2.8 mmol, 81% yield) was removed by filtration, washed with water (10 mL), and dried under vacuum. 1H-NMR (400 MHz, DMSO-d6) δ 12.38 (s, Petition 870220032852, dated 04 / 18 / 2022, pp. 189 / 320 182 / 312 1H), 9.16 (dd, J = 7.0, 1.8 Hz, 1H), 8.69 (q, J = 2.0 Hz, 1H), 7.16 (dd, J = 6.7, 4.3 Hz, 1H), 3.14 (q, J = 7.3 Hz, 2H), 1.36 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 223.85 (M)+. c) Step 3: 2-(Ethylthio)-N-(5-(methylamino)-2(trifluoromethyl)pyridin-4-yl)pyrazolo[1,5-a]pyrimidine3-carboxamide:

[0371] To a suspension of 2-(ethylthio)pyrazolo[1,5a]pyrimidine-3-carboxylic acid (325 mg, 1.5 mmol) in anhydrous dichloromethane (14 ml), 2 drops of N,N-dimethylformamide were added, followed by the addition of oxalyl chloride (0.2 ml, 2.2 mmol), and the resulting mixture was stirred at 25 °C for 4 h. The reaction mixture was evaporated under reduced pressure at a bath temperature of 60 °C. The resulting residue was dissolved in anhydrous dichloromethane (14 ml) and added dropwise at 0 °C to a stirred solution of N-3-methyl-6-(trifluoromethyl)pyridine-3,4-diamine (278 mg, 1.5 mmol) and triethylamine (0.85 ml, 6.1 mmol). The reaction mixture was stirred at 25 °C for 16 h. After the reaction was complete, water (40 ml) was added to the reaction mixture, which was then extracted three times with ethyl acetate (20 ml). The combined ethyl acetate layers were dried over sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using 40% ethyl acetate in hexane as an eluent to obtain 2-(ethylthio)-N-(5(methylamino)-2-(trifluoromethyl)pyridin-4-yl)pyrazolo[1,5a]pyrimidine-3-carboxamide (392 mg, 1 mmol, 68% yield). 1H-NMR (400 MHz, CDCl₂) δ 8.45 (d, J = 6.8 Hz, 1H), 8.26 (d, J = 3.9 Hz, 1H), 8.11 (d, J = 6.1 Hz, 1H), Petition 870220032852, dated 04 / 18 / 2022, pp. 190 / 320 183 / 312 6.95 (s, 1H), 6.72 (dd, J = 6.8, 4.2 Hz, 1H), 5.18-4.61 (2H), 3.35 (s, 3H), 3.21 (q, J = 7.3 Hz, 2H), 1.41-1.44 (m, 3H); ESI MS (m / z) 397.05 (MH)+. d) Step 4: 2-(2-(Ethylthio)pyrazolo[1,5-a]pyrimidin3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5c]pyridine:

[0372] A mixture of 2-(ethylthio)-N-(5-(methylamino)-2(trifluoromethyl)pyridin-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (392 mg, 1 mmol), p-toluenesulfonic acid monohydrate (564 mg, 3 mmol) in N-methyl-2-pyrrolidone (9 ml) was irradiated in a microwave oven at 150 °C for 1.5 h under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was cooled to 25 °C. Water (50 ml) was added to the above reaction mixture followed by extraction with ethyl acetate (150 ml). The ethyl acetate layer was washed with water (30 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash chromatography on a silica gel column using 40% ethyl acetate in hexane as an eluent to obtain 2-(2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (256 mg, 0.7 mmol, 68 % yield). 1H-NMR (400 MHz, DMSO-d6) δ 9.27 (dd, J = 6.8, 1.7 Hz, 1H), 9.14 (s, 1H), 8.70 (dd, J = 4.3, 1.6 Hz, 1H), 8.19 (d, J = 0.7 Hz, 1H), 7.21 (dd, J = 6.8, 4.2 Hz, 1H), 4.01 (s, 3H), 3.22 (q, J = 7.3 Hz, 2H), 1.321.38 (m, 3H); ESI MS (m / z) 378.90 (MH)+. Example 9:Synthesis of 2-(2-(Ethylsulfonyl)pyrazole[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-c]pyridine (Compound No. 23): Petition 870220032852, of 18 / 04 / 2022, p. 191 / 320 184 / 312

[0373] To a solution of 2-(2-(ethylthio)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-c]pyridine (187 mg, 0.5 mmol) in dichloromethane (9 ml) m-chloroperbenzoic acid (262 mg, 1 mmol) was added in portions at 0-5 °C. The reaction mixture was stirred at 25 °C for 5 h. After completion of the reaction, the reaction mixture was diluted with aqueous sodium thiosulfate solution and extracted with dichloromethane (20 ml). The dichloromethane extract was washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash chromatography on a silica gel column using 60% ethyl acetate in hexane as an eluent to obtain 2-(2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (105 mg, 0.3 mmol, 52% yield).1H-NMR (400 MHz, DMSO-d6) δ 9.50 (dd, J = 7.1, 1.7 Hz, 1H), 9.22 (s, 1H), 8.87 (q, J =2.0. Hz, 1H), 8.25 (d, J = 0.7 Hz, 1H), 7.51 (dd, J = 7.2,4.0 Hz, 1H), 3.90 (s, 3H), 3.74 (q, J = 7.4 Hz, 2H), 1.24 (t, J = 7.5 Hz, 3H) ESI MS (m / z) 411.05 (MH)+. Example 10: Synthesis of 2-(2-(ethylsulfonyl)-7-(4fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (Compound no. 25):

[0374] To a solution of 2-(2-(ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (185 mg, 0.4 mmol) in dichloromethane (6 ml), m-chloroperbenzoic acid (208 mg, 0.8 mmol) was added in portions at 0-5 °C. The reaction mixture was stirred at 25 °C for 5 h. After completion of the Petition 870220032852, dated 04 / 18 / 2022, pp. 192 / 320 185 / 312 reaction, the reaction mixture was diluted with aqueous sodium thiosulfate solution and extracted with dichloromethane (15 ml). The dichloromethane layer was washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash chromatography on a silica gel column using 60% ethyl acetate in hexane as an eluent to obtain - (2-(ethylsulfonyl)-7-(4-fluorophenyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine (120 mg, 0.2 mmol, 61% yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.90 (d, J = 4.6 Hz, 1H), 8.85 (d, J = 1.5 Hz, 1H), 8.63 (d, J = 1.5 Hz, 1H), 8.25-8.28 (m, 2H), 7.69 (d, J = 4.6 Hz, 1H), 7.53-7.59 (m, 2H), 3.81 (s, 3H), 3.73 (q, J = 7.4 Hz, 2H), 1.26 (t, J = 7.3Hz, 3H); ESI MS (m / z) 505.10 (MH)+. Example 11: Synthesis of 2-(7-(3-Chloro-5-fluorophenyl)-2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (Compound No. 102): a) Step-1: 2-Cyano-N-(2-(methylamino)-5-(trifluoromethyl)pyridin-3-yl)acetamide:

[0375] To a stirred solution of 2-cyanoacetic acid (7 g, 82 mmol), N2-methyl-5-(trifluoromethyl)pyridine-2,3-diamine (12.58 g, 65.8 mmol) and hydroxybenzotriazole (HOBt) (15.12 g, 99 mmol) in dimethylformamide (350 ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC-HCl) (18.93 g, 99.0 mmol) and N,N-diisopropylethylamine (35.9 ml, 206 mmol) were added. The resulting mixture was stirred at 25 °C for 24 h under a nitrogen atmosphere. After completion Petition 870220032852, dated 04 / 18 / 2022, pp. 193 / 320 186 / 312 of the reaction, water (100 ml) was added to the reaction mixture above, and the reaction mixture was extracted three times with ethyl acetate (100 ml). The combined layers of ethyl acetate were dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using 30% ethyl acetate in hexane as an eluent to obtain 2-cyano-N-(2-(methylamino)5-(trifluoromethyl)pyridin-3-yl)acetamide (11.8 g, 45.7 mmol, 55.5% yield). 1H-NMR (400 MHz, DMSO-d6) δ 9.61(s, 1H), 8.26 (d, J = 1.0 Hz, 1H), 7.64 (d, J = 2.4 Hz, 1H), 6.94 (d, J = 4.4 Hz, 1H), 3.83 (d, J = 17.6 Hz, 2H), 2.87 (d, J = 4.6 Hz, 3H); ESI MS (m / z)258(M)+. b) Step-2: 2-(3-Methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)acetonitrile:

[0376] A solution of 2-cyano-N-(2-(methylamino)-5(trifluoromethyl)pyridin-3-yl)acetamide (11.8 g, 45.7 mmol) in acetic acid (120 ml) was heated at 100 °C for 2 h. After the reaction was complete, the reaction mixture was cooled to 25 °C. The reaction mixture was concentrated under reduced pressure to remove acetic acid. Water (100 ml) was added to the concentrated reaction mixture, and the reaction mixture was extracted three times with ethyl acetate (75 ml). The ethyl acetate layer was washed with water (100 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash chromatography on a silica gel column using 15% ethyl acetate in hexane as an eluent to obtain 2-(3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridin-2-yl)acetonitrile (9.0 g, 37.5 mmol, Petition 870220032852, dated 04 / 18 / 2022, pp. 194 / 320 187 / 312% yield).1H-NMR (400 MHz, DMSO-d6) δ 8.76 (t, J = 1.0 Hz, 1H), 8.55-8.56 (m, 1H), 4.69 (s, 2H), 3.82 (s, 3H); ESI MS (m / z) 240.95 (MH) + . c) Step-3:3,3-Bis(ethylthio)-2-(3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2yl)acrylonitrile

[0377] To a stirred solution of 2-(3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)acetonitrile (8.8 g, 36.6 mmol) in acetonitrile (80 ml), potassium hydroxide (4.84 g, 73.3 mmol) was added at 25 °C. The resulting reaction mixture was stirred for 1 hour at 25 °C. The reaction mixture was further cooled to -5 °C and carbon disulfide (2.2 ml, 36.6 mmol) was added dropwise over 10 minutes. The reaction mixture was stirred for 1 hour at -5 °C. Additionally, ethyl iodide (5.92 ml, 73.3 mmol) was added dropwise at 0 °C over 15 minutes. The reaction mixture was stirred again for 2 hours at 0 °C and left at 0 °C for 16 hours. The reaction mixture was concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column using 10% ethyl acetate in hexane as an eluent to obtain 3,3-bis(ethylthio)-2-(3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridin-2-yl)acrylonitrile (12.4 g, 33.3 mmol, 91% yield), 1H-NMR (400 MHz, DMSO-d6) δ 8.84 (q, J = 1.0 Hz, 1H), 8.62 (q, J = 0.9 Hz, 1H), 3.87 (s, 3H), 3.25 (q, J = 7.3 Hz, 2H), 2.84 (q, J = 7.4 Hz, 2H), 1.37 (t, J = 7.2 Hz, 3H), 1.14 (t, J = 7.3 Hz, 3H); ESI MS (m / z)373.00 (MH)+. d) Step-4: 3-(Ethylthio)-4-(3-methyl-6- Petition 870220032852, of 18 / 04 / 2022, p. 195 / 320 188 / 312 (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)1H-pyrazole-5-amine

[0378] To a stirred solution of 3,3-bis(ethylthio)-2-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)acrylonitrile (1 g, 2.69 mmol) in a mixture of acetonitrile (1 ml) and ethanol (2 ml), hydrazine monohydrate (0.17 ml, 2.69 mmol (79% w / v)) was added dropwise at 0 °C. The reaction mixture was stirred at 0 °C for 1 hour. The reaction mixture was diluted with ice-cold water (20 ml), and the solid was precipitated. The precipitated solid was filtered, washed with water, and dried under vacuum to obtain the crude product. The crude product was purified by silica gel column chromatography using 100% ethyl acetate as an eluent to obtain 3-(ethylthio)4-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2yl)-1H-pyrazol-5-amine (720 mg, 2.1 mmol, 78% yield). 1H-NMR (400 MHz, DMSO-D6) δ 12.01 (s, 1H), 8.66 (s, 1H), 8.37 (s, 1H), 5.75 (s, 2H), 3.77 (s, 3H), 2.88 (q, J = 6.8 Hz, 2H), 1.15 (t, J = 6.8 Hz, 3H); ESI MS (m / z) 343.00 (MH)+. e) Step-5:2-(Ethylthio)-3-(3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one

[0379] To a stirred solution of 3-(ethylthio)-4-(3-methyl6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)-1Hpyrazol-5-amine (550 mg, 1.61 mmol) together with its non-cyclized intermediate in acetic acid (5 ml), methyl 3,3-dimethoxypropanoate (0.34 ml, 2.41 mmol) was added. The reaction mixture was heated to 100 °C for 6 h. The reaction mixture was cooled to 25 °C and concentrated. Petition 870220032852, dated 04 / 18 / 2022, pp. 196 / 320 189 / 312 under reduced pressure to remove acetic acid. Water (20 ml) was added to the concentrated reaction mixture above, and the reaction mixture was extracted three times with ethyl acetate (25 ml). The ethyl acetate layer was washed with water (50 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash chromatography on a silica gel column using 5% methanol in dichloromethane as an eluent to obtain 2-(ethylthio)-3-(3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one (375 mg, 0.95 mmol, 59% yield). 1H-NMR (400 MHz, DMSO-d6) δ 12.40 (s, 1H), 8.80 (q, J = 0.9 Hz, 1H), 8.56 (dd, J = 2.1, 0.6 Hz, 1H), 7.84 (d, J = 7.3 Hz, 1H), 5.87 (d, J = 7.3 Hz, 1H), 3.77 (s, 3H), 3.16 (q, J = 7.3 Hz, 2H), 1.32 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 395.00(MH)+. f) Step-6: 2-(7-Bromo-2-(ethylthio)pyrazolo[1,5- a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine

[0380] A stirred solution of 2-(ethylthio)-3-(3-methyl6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one (1.05 g, 2.66 mmol) in acetonitrile (28 ml), potassium carbonate (1.10 g, 7.99 mmol) and phosphorus oxybromide (2.29 g, 7.99 mmol) was added at 25 °C. The reaction mixture was further heated to 95 °C for 4 h. The reaction mixture was cooled to 0 °C. The reaction mixture was diluted with ice-cold water (50 ml). The pH of the reaction mixture was adjusted to 7-8 using the slow addition of saturated aqueous sodium bicarbonate solution. The reaction mixture Petition 870220032852, dated 04 / 18 / 2022, pp. 197 / 320 190 / 312 was extracted three times with ethyl acetate (50 ml). The ethyl acetate layer was washed with water (50 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash chromatography on a silica gel column using 50% ethyl acetate in hexane as an eluent to obtain 2-(7-bromo-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (980 mg, 2.14 mmol, 80% yield). 1H-NMR (400 MHz, DMSOd6) δ 8.77 (t, J = 1.1 Hz, 1H), 8.55 (d, J = 1.5 Hz, 1H), 8.48 (d, J = 4.6 Hz, 1H), 7.65 (d, J = 4.6 Hz, 1H), 3.92 (s, 3H), 3.25 (q, J = 7.3 Hz, 2H), 1.40 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 456, 95, 458.95(MH; Br79.81) + g) Step-7: 2-(7-(3-Chloro-5-fluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine

[0381] To a solution of 2-(7-bromo-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (170 mg, 0.37 mmol) and (3-chloro-5-fluorophenyl)boronic acid (78 mg, 0.446 mmol) in a mixture of tetrahydrofuran (4 ml) and water (2 ml), sodium carbonate (197 mg, 1.86 mmol) was added. The reaction mixture was completely deoxygenated by three vacuum / nitrogen cycles. Tetracis(triphenylphosphine)palladium(0) (12.9 mg, 0.01 mmol) was added to the reaction mixture and heated to 85 °C for 4 h. After the reaction was complete, the reaction mixture was cooled to 25 °C and filtered through a celite block. The filtrate was concentrated under reduced pressure, and the crude product was purified by flash column chromatography. Petition 870220032852, dated 04 / 18 / 2022, pp. 198 / 320 191 / 312 silica gel using 20% ​​ethyl acetate in hexane as an eluent to obtain 2-(7-(3-chloro-5-fluorophenyl)-2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (120 mg, 0.24 mmol, 64% yield) . 1H-RMN (400 MHz, DMSO-d6) δ 8,778.79 (m, 2H), 8.55 (d, J = 1.5 Hz, 1H), 8.23 ​​(d, J = 1.5 Hz, 1H), 8.10 (dq, J = 9.7, 1.2 Hz, 1H), 7.79 (dt, J = 8.8, 2.1 Hz, 1H), 7.55 (d, J = 4.6 Hz, 1H), 3.96 (s, 3H), 3.16 (q, J = 7.3 Hz, 2H), 1.40 (t, J = 7.2 Hz, 3H); ESI MS (m / z) 506.95, 508.95(MH; Cl35.37) + . Exemplo-12: Synthesis of 3-(7-(3,5-Dichlorophenyl)-2(ethylsulfonyl)pyrazolo[1,5-a]pirimidin-3-yl)-6(trifluoromethyl)-[1,2,4]triazolo[4,3-a]piridine (Compound No. 111) a) Etapa-1: 2-Hydrazine-5- (trifluoromethyl)pyridine:

[0382] To a stirred solution of 2-chloro-5(trifluoromethyl)pyridine (10.0 g, 55.1 mmol) in ethanol, hydrazine hydrate (5.18 g, 123 mmol) was added. The resulting reaction mixture was stirred at 90°C for 16 h. The reaction mixture was cooled to 25°C and concentrated under reduced pressure to remove ethanol. Water (50 ml) was added to the concentrated reaction mixture above, and the reaction mixture was extracted three times with ethyl acetate (200 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 2-hydrazinyl-5(trifluoromethyl)pyridine (8.50 g, 48.00 mmol, 87% yield), 1H-NMR (400 MHz, DMSO-d6) δ 8.25 (d, J = 0.7 Hz, 2H), 7.68 (dd, J = 9.0, 2.4 Hz, 1H), 6.78 (d, J = 9.0 Hz, 1H), 4.32 (s, 2H); ESI MS (m / z) 178.10 (MH)+. Petition 870220032852, dated 04 / 18 / 2022, pp. 199 / 320 192 / 312 b) Stage-2: 7-(3,5-Dichlorophenyl)-2-(ethylthio)-N'-(5- (trifluoromethyl)pyridin-2-yl)pyrazolo[1,5a]pyrimidine-3-carbo-hydrazide:

[0383] To a stirred solution of 2-hydrazinyl-5(trifluoromethyl)pyridine (0.80 g, 4.52 mmol) in N,Ndimethylformamide (8 mL), 7-(3,5-dichlorophenyl)-2(ethylthio)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (1.66). g, 4.52 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochlorate (1.29 g, 6.77 mmol), 1-hydroxybenzotriazole (0.91 g, 6.77 mmol) and N,N-di-isopropylethylamine (1.75 ml. 13.55 mmol) were added at 0°C. The reaction mixture was stirred at 25°C for 16 h under a nitrogen atmosphere. After the reaction was complete, water (20 ml) was added to the reaction mixture, and the precipitate was filtered and dried under reduced pressure to obtain 7-(3,5-dichlorophenyl)-2(ethylthio)-N'-(5-(trifluoromethyl)pyridin-2-yl)pyrazolo[1,5a]pyrimidine-3-carbohydrazide (1.2 g, 2.27 mmol, 50% yield). 1H-NMR (400 MHz, DMSO-d6) δ 9.78 (s, 1H), 9.39 (s, 1H), 8.83 (dd, J = 11.9, 4.6 Hz, 1H), 8.42 (d, J = 20.2 Hz, 1H), 8.24-8.29 (m, 2H), 7.91-7.99 (m, 1H), 7.84 (dd, J = 8.9, 2.1 Hz, 1H), 7.58-7.61 (m, 1H), 6.77 (d, J = 8.7 Hz, 1H), 3.09 (q, J = 7.2 Hz, 2H), 1.40 (t, J = 7.2 Hz, 3H); ESI MS (m / z) 527.25 (MH)+. c) Step-3: 3-(7-(3,5-Dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-6(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine:

[0384] 7-(3,5-Dichlorophenyl)-2-(ethylthio)-N'-(5(trifluoromethyl)pyridin-2-yl)pyrazolo[1,5-a]pyrimidine-3-carbohydrazide (1 g, 1.90 mmol) was added to phosphoryl chloride (3 ml), and the resulting reaction mixture was Petition 870220032852, dated 04 / 18 / 2022, pages 200 / 320 193 / 312 heated to 90 °C for 6 h. The reaction mixture was cooled to 25 °C and concentrated under reduced pressure. The reaction mixture was further cooled to 0 °C, and the resulting mass was treated with saturated bicarbonate solution to make the pH basic (pH 9). The resulting mixture was extracted three times with ethyl acetate (50 ml). The combined ethyl acetate layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using 25% ethyl acetate in hexane as an eluent to obtain 3(7-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin3-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine (500 mg, 0.98 mmol, 52% yield). 1H-NMR (400 MHz, DMSO-d6) δ 9.09 (d, J = 1.0 Hz, 1H), 8.72 (d, J = 4.4 Hz, 1H), 8.32 (d, J = 2.0 Hz, 2H), 8.09 (d, J = 9.8 Hz, 1H), 7.96 (t, J = 2.0 Hz, 1H), 7.68 (dd, J = 9.7, 1.6 Hz, 1H), 7.56-7.58 (m, 1H), 3.17 (q, J = 7.3 Hz, 2H), 1.42 (t, J = 7.3Hz, 3H); ESI MS (m / z) 508.70(MH)+. d) Step-4: 3-(7-(3,5-Dichlorophenyl)-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine:

[0385] To a solution of 3-(7-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)[1,2,4]triazolo[4,3-a]pyridine (0.35 g, 0.68 mmol) in dichloromethane (8 ml), m-chloroperbenzoic acid (0.58 g, 2.06 mmol, 60%) was added at 0 °C. The resulting reaction mixture was stirred at 25 °C for 16 h. The reaction mixture was diluted with dichloromethane (20 ml) and washed twice with aqueous saturated sodium bicarbonate (20 ml), followed Petition 870220032852, dated 04 / 18 / 2022, pp. 201 / 320 194 / 312 by water (10 ml). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using 30% ethyl acetate in hexane as an eluent to obtain 3(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3a]pyridine (210 mg, 0.388 mmol, 56% yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.90 (d, J = 4.4 Hz, 2H), 8.24 (d, J = 1.7 Hz, 2H), 8.15 (d, J = 9.5 Hz, 1H), 8.01 (t, J = 2.0 Hz, 1H), 7.82 (d, J = 4.6 Hz, 1H), 7.74 (dd, J = 9.7, 1.6 Hz, 1H), 3.62 (q, J = 7.3 Hz, 2H), 1.27 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 540, 90(MH) + . Example 13: Synthesis of(7-(3,5-dichlorophenyl)-3-(3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(imino)-X6-sulfanone (Compound No. 135):

[0386] To a stirred solution of 2-(7-(3,5-dichlorophenyl)2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (312 mg, 0.60 mmol) and ammonium carbamate (140 mg, 1.79 mmol) in methanol (6 ml), iodobenzene diacetate (384 mg, 1.19 mmol) was added at 0 °C. The resulting reaction mixture was stirred at 25 °C for 16 h. The reaction mixture was concentrated under reduced pressure. The crude residue was diluted with water (20 ml), and the mixture was extracted three times with ethyl acetate (50 ml). The ethyl acetate layer was washed with water (30 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by preparative HPLC to obtain (7-(3,5Petition 870220032852, dated 18 / 04 / 2022, page 202 / 320 195 / 312 dichlorophenyl)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5b]pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(imino)X6-sulfanone (110 mg, 0.2 mmol, 44% yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.90 (d, J = 4.4 Hz, 1H), 8.84 (d, J = 1.2 Hz, 1H), 8.62 (t, J = 1.1 Hz, 1H), 8.25 (d, J = 2.0 Hz, 2H), 7.98 (t, J = 2.0 Hz, 1H), 7.75 (d, J = 4.4 Hz, 1H), 4.80 (s, 1H), 3.81 (s, 3H), 3.49-3.56 (m, 2H), 1.28 (t, J = 7.5Hz, 3H); ESI MS (m / z) 554.00(MH)+.

[0387] The following compounds (Table-1) were obtained using analogous procedures, as described in Schemes 1-23, or in the examples. Table 1: No. of comp. Compound Name Analytical Data 1 2 - (1-(3,5-Dichlorophenyl)-2- (ethylsulfonyl)indolizin-3-yl)-3methyl-6-(trifluoromethyl)-3himidazo[4,5-b]pyridine 1H-NMR (400 MHz, DMSO-d6) δ 8.92 (t, J = 2.2). Hz, 1H), 8.71 (t, J = 2.2 Hz, 1H), 8,158.17 (m, 1H), 7.68-7.74 (m, 3H), 7,527.55 (m, 1H), 7.16-7.20 (m, 1H), 6,936.99 (m, 1H), 3.79 (s, 3H), Petition 870220032852, 4 / 18 / 2022, p. 203 / 3 196 / 3 No. of comp. Composite Name Analytical Data 3.05 (dtd, J ...

Claims

1. Compound of formula (I), Formula (I) characterized in that R1 is selected from the group consisting of C1-C6-alkyl; Y is independently selected from O or NRY; RY is selected from the group consisting of hydrogen and C1-C4-alkyl; the fused rings D and E are selected from the group consisting of DE-1, DE-7 and DE-11, wherein # denotes the point of attachment to ring Q and · denotes the point of attachment to the -S(Y)mR1 group; en is an integer ranging from 0 to 4 in the case of DE-1 or DE-11, and is an integer ranging from 0 to 3 in the case of DE-7; R2 is selected from the group consisting of hydrogen, halogen, C6C10-aryl; wherein each cyclic group of R2 may be substituted with one or more groups of R2b; R2b is selected from the group consisting of halogens Q is selected from: Petition 870260066400, dated 06 / 07 / 2026, page 8 / 39 2 / 13 Q1b Q7a Q5b where # denotes the point of union to the D ring; en is an integer ranging from 0 to 2;R3 is selected from the group consisting of C1-C6-haloalkyl, and S(O)o2R7; R11 is selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR4, NR5R6, S(O)o-2R7, S(O)o-iR9=NR10, N=S(O)oi(R9)2, C6-C10-aryl, and C3-C10-heterocyclyl; wherein each aliphatic group may be substituted with one or more groups of R11a and the cyclic groups of R11 may optionally be substituted with one or more groups of R11b; R11a is selected from the group consisting of halogen, cyano, C1-C6-alkyl and C3-C8-cycloalkyl; R11b is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl and OR4; R4, R5 and R6 are selected from the group consisting of hydrogen, C1-C6-alkyl and C1-C6-haloalkyl; R7 is selected from the group consisting of C1-C6-alkyl and C1-C6-haloalkyl; R9 is selected from the group consisting of C1-C6-alkyl and C1-C6-haloalkyl;R10 is selected from the group consisting of hydrogen, cyano, C1-C6 alkyl and C1-C6 haloalkyl; m is an integer ranging from 0 to 2; or agrochemically acceptable salts thereof.

2. Consisting of formula (I), according to indication 1, characterized by the fact that the finger composed of formula (I) is selected starting from 2-(1-(3,5dichlorophenyl)-2-(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5b]pyridine; 2-(2-(ethylsulfonyl)imidazo[1,2-a]pyridin-3-yl)-3-methyl-6-(trifluoromethyl)-3H- imidazo[4,5-b]pyridine; 6-(1-bromo-2-(ethylsulfonyl)indolizin-3-yl)-7-methyl-3-(trifluoromethyl)7H-imidazo[4,5-c]pyridazine; 2-(2-(ethylsulfonyl)imidazo[1,2-a]pyridin-3-yl)-5(trifluoromethyl)benzo[d]oxazol; 2-(2-(ethylsulfonyl)-7-(trifluoromethyl)indolizin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(8-(3,5-dichlorophenyl)-2-(ethylsulfonyl)indolizin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(1-(3,5-dichlorophenyl)-2-(ethylsulfonyl)-7-(trifluoromethyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5b]pyridine; 2-(6-(3,5-dichlorophenyl)-2-(ethylsulfonyl)indolizin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine;2-(2-(ethylthio)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5,7-dimethylpyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5,7dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2(2-(ethylsulfonyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-c]pyridine; 2-(2-(ethylthio)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-5((trifluoromethyl)thio)benzo[d]oxazol; 2-(2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5,7-dimethylpyrazolo[1,5a]pyrimidin-3-yl)-5-((trifluoromethyl)sulfonyl)benzo[d]oxazol; 2-(2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)thio)benzo[d]oxazol;2-(2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(2(ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(4-fluorophenyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2Petition 870260066400, dated 06 / 07 / 2026, page 10 / 39 4 / 13 (ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2(2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5c]pyridine; 2-(7-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(4-fluorophenyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine;2-(7-(3,5-dichlorophenyl)2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5b]pyridine; 2-(2-(ethylthio)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(4(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(4(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)thio)benzo[d]oxazole; 2-(2-(ethylsulfonyl)-7-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(2-(ethylthio)-7-(4-fluorophenyl)pyrazolo[1,5a]pyrimidin-3-yl)-5-((trifluoromethyl)thio)benzo[d]oxazole;2-(2-(ethylsulfonyl)-7-(4fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)sulfonyl)benzo[d]oxazol; 2-(7-(4chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5c]pyridine; 2-(7-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(4-chlorophenyl)-2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)thio)benzo[d]oxazol; 2-(7-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine; 2-(7-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5((trifluoromethyl)sulfonyl)benzo[d]oxazole; 2-(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine;2-(7-(3,5-dichlorophenyl)2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-5-((trifluoromethyl)thio)benzo[d]oxazol; 2-(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-5((trifluoromethyl)sulfonyl)benzo[d]oxazol; 2-(2-(ethylthio)-5-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3Petição 870260066400, de 06 / 07 / 2026, pág. 11 / 39 5 / 13 metil-6-(trifluorometil)-3H-imidazo[4,5-c]piridine; 2-(2-(ethylthio)-5-phenylpyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-5phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2(ethylsulfonyl)-5-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5c]pyridine; 2-(6-chloro-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine; 2-(2-(ethylthio)-6-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine;2-(6-chloro-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-metil-6-(trifluorometil)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5-(4(trifluoromethoxy)fenil)pyrazolo[1,5-a]pyrimidin-3-yl)-3-metil-6-(trifluorometil)-3Himidazo[4,5-c]pyridine; 2-(6-chloro-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(6-chloro-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-metil-6-(trifluorometil)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-6fenilpyrazolo[1,5-a]pyrimidin-3-yl)-3-metil-6-(trifluorometil)-3H-imidazo[4,5-b]pyridine; 2-(2(ethylthio)-5-(4-(trifluoromethoxy)fenil)pyrazolo[1,5-a]pyrimidin-3-yl)-3-metil-6-(trifluorometil)3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-5-(4fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5b]pyridine;2-(6-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5-(4(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-5-(4-fluorophenyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-5-(4fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5b]pyridine; 2-(6-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-6-phenylpyrazolo[1,5-a]pyrimidin-3-yl)3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(5-(3,5-dichlorophenyl)-2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine;2(2-(ethylsulfonyl)-6-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-c]pyridine; 2-(5-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3Petição 870260066400, de 06 / 07 / 2026, pág. 12 / 39 6 / 13 methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(5-(3,5-dichlorophenyl)-2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2(5-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)3H-imidazo[4,5-c]pyridine; 2-(6-bromo-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-Bromo-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-(3,5-dichlorophenyl)2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-(4-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-c]pyridine;2-(6-(4-chlorofenil)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3metil-6-(trifluorometil)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-5-(4-(1,1,2,2tetrafluoroethoxy)fenil)pyrazolo[1,5-a]pyrimidin-3-yl)-3-metil-6-(trifluorometil)-3Himidazo[4,5-c]pyridine; 2-(6-(3,5-dichlorofenil)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3metil-6-(trifluorometil)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-5-(4(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(6-(3,5-dichlorofenil)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3metil-6-(trifluorometil)-3H-imidazo[4,5-c]pyridine;2-(6-(3,5-dichlorofenil)-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-metil-6-(trifluorometil)-3H-imidazo[4,5c]pyridine; 2-(2-(ethylthio)-6-(4-(trifluoromethoxy)fenil)pyrazolo[1,5-a]pyrimidin-3-yl)-3-metil-6(trifluorometil)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-6-(4(trifluoromethoxy)fenil)pyrazolo[1,5-a]pyrimidin-3-yl)-3-metil-6-(trifluorometil)-3Himidazo[4,5-b]pyridine; 2-(5-(4-chlorofenil)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(5-(4-chlorofenil)-2-(ethylthio)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-6-(4(trifluoromethoxy)fenil)pyrazolo[1,5-a]pyrimidin-3-yl)-3-metil-6-(trifluorometil)-3Himidazo[4,5-c]pyridine; 2-(2-(ethylthio)-7-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine;2-(5-(4-chlorophenyl)-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5Petição 870260066400, de 06 / 07 / 2026, pág. 13 / 39 7 / 13 b]pyridine; 2-(5-(4-chlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(4-(1,1,2,2tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 3-(7-(3,5-dichlorophenyl)2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)-[1,2,4]triazole[4,3-a]pyridine; 2-(2(ethylthio)-7-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 3-(7-(3,5-dichlorophenyl)-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine;2-(2-(ethylthio)-6-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-6-(4-(1,1,2,2tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3-chlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3,5-difluorophenyl)-2-(ethylthio)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3-chlorophenyl)-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5b]pyridine; 2-(2-(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3,5-difluorofenil)-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-metil-6-(trifluorometil)-3H-imidazo[4,5b]pyridine;2-(7-(3-chloro-5-fluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3-chloro-5-fluorophenyl)-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3,4-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 7-(3,5-Dichlorophenyl)-2-(ethylthio)-3-(1-methyl-5(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)pyrazolo[1,5-a]pyrimidine; 2-(ethylthio)-3-(1 -methyl-5(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)pyrazolo[1,5-a]pyrimidine; 7-(3,5-dichlorophenyl)-2(ethylsulfonyl)-3-(1 -methyl-5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)pyrazolo[1,5a]pyrimidine; 2-(ethylsulfonyl)-3-(1-methyl-5-(trifluoromethyl)-1H-benzo[d]imidazol-2yl)pyrazolo[1,5-a]pyrimidine; 2-(2-(ethylsulfonyl)-6-(4-(1,1,2,2tetrafluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3HPetição 870260066400, de 06 / 07 / 2026, pág. 14 / 39 8 / 13 imidazo[4,5-c]pyridine;3-(7-(3,5-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-6(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine; 3-(7-(3,5-dichlorophenyl)-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine; 2(7-(2,3-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(2,3-dichlorophenyl)-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-phenylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)3H-imidazo[4,5-b]pyridine; 2-(7-(4-chloro-3-fluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(3,5-dichlorophenyl)-2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine;2(7-(4-chloro-3-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(4-chloro-3-fluorophenyl)-2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2(7-(2,4-dichlorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine; 2-(7-(2,4-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(2,4-dichlorophenyl)-2(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2(7-(3-chloro-5-fluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)3H-imidazo[4,5-c]pyridine; 2-(7-(3-chloro-5-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7-(3,5bis(trifluoromethyl)phenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine;2-(2-(ethylthio)-7-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(3fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5b]pyridine; 2-(7-(3,5-bis(trifluoromethyl)phenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(3(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5b]pyridine; 2-(2-(ethylsulfonyl)-7-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-methylpyrazolo[1,5-a]pyrimidin-3-yl)Petição 870260066400, de 06 / 07 / 2026, pág. 15 / 39 9 / 13 3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(3fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5c]pyridine;2-(2-(ethylsulfonyl)-7-methylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)3H-imidazo[4,5-b]pyridine; 2-(2-(ethylthio)-7-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-3yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; (7-(3,5-dichlorophenyl)-3-(3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(imino)-D6sulfanone; 2-(2-(ethylsulfonyl)-7-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylsulfonyl)-7-(3-fluorophenyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(2-(ethylthio)-7methylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine; 2-(7(3-chloro-4-fluorophenyl)-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3Himidazo[4,5-b]pyridine; 2-(2-(ethylthio)-5,7-bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine;2-(2-(ethylsulfonyl)-5,7bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5b]pyridine; 2-(ethylthio)-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[1,5a]pyrimidin-7(4H)-one; 2-(7-bromo-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(ethylsulfonyl)-N-methyl-3-(7-(trifluoromethyl)[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine; 6-(8-(4-chloro-3fluorofenil)-2-(ethylsulfonyl)indolizin-3-yl)-7-metil-3-(trifluorometil)-7H-imidazo[4,5c]pyridazine; 2-(2-(ethylsulfonyl)-7-(5-metil-3-(trifluorometil)-1H-pyrazol-1-yl)pyrazolo[1,5a]pyrimidin-3-yl)-3-metil-6-(trifluorometil)-3H-imidazo[4,5-b]pyridine; 2-(ethylthio)-N-methyl-3(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine; 2-(2-(ethylsulfonyl)-7-(3-fluorophenoxy)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)3H-imidazo[4,5-b]pyridine;6-(8-(4-chloro-3-fluorophenyl)-2-(ethylsulfonyl)imidazo[1,2-a]pyridin-3-yl)-7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine; 2-(6-(3,5-dichlorophenyl)-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyrazine; 4-(2(ethylsulfonyl)-3-(7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazin-6-yl)indolizin-8-yl)-2fluorobenzonitrile; 2-(8-(cyclopropylmethyl)-2-(ethylsulfonyl)imidazo[1,2-a]pyridin-3-yl)-3-methyl6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-(4-cloro-1H-pyrazol-1-yl)-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-metil-6-(trifluorometil)-3H-imidazo[4,5Petição 870260066400, de 06 / 07 / 2026, pág. 16 / 39 10 / 13 b]pyridine; 2-(2-(ethylsulfonyl)-7-(5-methyl-1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(1-methyl-1H-pyrazol5-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine;2-(2(ethylsulfonyl)-7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-cyclopropyl-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrazine; 2(2-(ethylsulfonyl)-7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-7(trifluoromethyl)imidazo[1,2-c]pyrimidine; 4-(2-(ethylsulfonyl)-3-(7-(trifluoromethyl)imidazo[1,2a]pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)morpholine; 2-(7-(4-chloro-3-fluorophenyl)-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-c]pyrimidine; 2-(2-(ethylsulfonyl)-7-(1H-1,2,4-triazol-1 -yl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-c]pyrimidine; 2-(2-(ethylsulfonyl)-5,7-bis(trifluoromethyl)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 6-(1-bromo-2(ethylsulfonyl)-8-methylindolizin-3-yl)-7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine;6-(8-bromo-2-(ethylsulfonyl)indolizin-3-yl)-3-(difluoromethyl)-7-methyl-7H-imidazo[4,5c]pyridazine; 2-(2-(ethylsulfonyl)-7-methoxypyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(2-(ethylsulfonyl)-7-(methylthio)pyrazolo[1,5a]pyrimidin-3-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(ethylsulfonyl)-3-(3methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyrazolo[1,5-a]pyrimidine-7(4H)-thione; 2-(2-(ethylsulfonyl)-7-(1,1,2,2-tetrafluoroethoxy)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methyl-6(trifluoromethyl)-3H-imidazo[4,5-b]pyridine; 2-(7-ethoxy-2-(ethylsulfonyl)pyrazolo[1,5a]pyrimidin-3-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyrazine; diethyl((2-(ethylsulfonyl)-3-(6(trifluoromethyl)imidazo[1,2-a]pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)imino)-16-sulfanone; 2-(ethylsulfonyl)-N,N-dimethyl-3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2yl)imidazo[1,2-a]pyridin-8-amine;6-(2-(ethylsulfonyl)-7-(5-(trifluoromethyl)pyridin-2yl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-methyl-3-(trifluoromethyl)-7H-imidazo[4,5-c]pyridazine; 2-(7(4-chloro-3-fluorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-3,5-dimethyl-6(trifluoromethyl)-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-ona; 2-(2-(ethylsulfonyl)-7-(3(trifluoromethyl)-1H-1,2,4-triazol-1 -yl)pyrazolo[1,5-a]pirimidin-3-yl)-3,5-dimethyl-6(trifluoromethyl)-3,5-dihydro-4H-imidazo[4,5-c]piridin-4-one; 2-(7-(3-chloro-5-fluorophenyl)-2Petição 870260066400, de 06 / 07 / 2026, pág. 17 / 39 11 / 13 (ethylsulfonyl)pyrazolo[1,5-a]pirimidin-3-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrazine; 2(7-(3,5-dichlorophenyl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-7(trifluoromethyl)imidazo[1,2-c]pyrimidine; 2-(7-(4-chloro-3-fluorophenyl)-2(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-methyl-7-(trifluoromethyl)-[1,2,4]triazolo[1,5c]pyrimidin-5(6H)-one;2-(7-(5-chloropyridin-2-yl)-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine; 2-(2-(ethylsulfonyl)-7-(5-methyl-3(trifluoromethyl)-1H-pyrazol-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-6-methyl-7-(trifluoromethyl)[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one; 2-(2-(ethylsulfonyl)-7-(3-(trifluoromethyl)-1H-1,2,4triazol-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-c]pyrimidine; ethyl(3-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-2yl)(methylimino)-16-sulfanone; 3. Composition for controlling or preventing insect and / or mite pests characterized by comprising a biologically effective amount of the compound of formula (I) or agronomically acceptable salts thereof as defined in claim 1 and at least one additional component selected from the group consisting of surfactants and auxiliaries.

4. Composition, according to claim 3, said composition being characterized by further comprising at least one additional compatible active biological compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers or nutrients.

5. Composition according to claim 3, characterized in that said biologically effective amount of compound of formula (I) varies from 0.1% to 99% by weight relative to the total weight of the composition.

6. Composition according to claim 5, characterized in that said biologically effective amount of compound of formula (I) varies from 5 to 50% by weight relative to the total weight of the composition.

7. Combination characterized by comprising a biologically effective amount of the compound as defined in claim 1 and at least one additional compatible biological active compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients.

8. A method for controlling insect and mite pests characterized by comprising contacting the insects and mite pests, their habitat, breeding grounds, food supply, plants, seeds, soil, areas, materials or environments 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 the compound of formula (I) or salts, composition or combination thereof as defined in claim 1 or 3 or 7, wherein application to the human or animal body is excluded.

9. Method for protecting crops from attack or infestation by insect and mite pests, characterized by comprising contacting the crop with a biologically effective quantity of the compound or salts, composition or combination thereof as defined in claim 1, 3 or 7.

10. Method according to claim 10 or 11, said method being characterized by comprising applying effective dosages of the compound of formula (I) in amounts ranging from 1 g to 5000 g per hectare in agricultural or horticultural crops.

11. Method for protecting seeds, plants and plant parts from soil insects and the roots and shoots of seedlings from soil and foliar insects, characterized by comprising contacting the seeds before sowing and / or after pre-germination with the compound of formula (I) or salts, composition or combination thereof as defined in claim 1 or 3 or 7.

12. Use of the compound of formula (I) or salts, composition or combination thereof as defined in claim 1 or 3 or 7, characterized in that it is for combating insect and mite pests in agricultural, horticultural, vector control and domestic use, wherein application to the human or animal body is excluded.

13. Use of the compound of formula (I), according to claim 12, characterized in that said agricultural crops are cereals, maize, sorghum, Petition 870260066400, dated 06 / 07 / 2026, page 19 / 39 13 / 13 bajra, rice, soybeans, oilseeds and other leguminous plants, fruits and fruit trees, grapes, nuts and walnut trees, citrus fruits and citrus trees, any horticultural plants, cucurbits, oilseed plants, tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton, potato, tomato, onion, pepper, other vegetables and ornamental plants.

14. Coated seed characterized by comprising a compound of formula (I) or salts, composition or combination thereof as defined in claim 1 or 6 or 9, wherein the amount of the compound of formula (I) in said seed varies from 0.0001% to 1% by weight.