Condensed heterocyclic compounds, compositions, combination products, methods, uses, and seeds

Abstract

Fused heterocyclic compounds and their use as pest control agents The present invention discloses fused heterocyclic compounds of formula (I). [Formula 1] TIFF2023513939000054.tif2143 formula (I) Here, Q and R 1 , R 2 , n, m and Y are as defined in the detailed description of the invention. The present invention further discloses methods for their preparation and the use of compounds of formula (I) as pest control agents.

Description

Technical Field

[0001] The present invention relates to a condensed heterocyclic compound. More specifically, the present invention relates to a condensed heterocyclic compound of formula (I) and a method for preparing the same. The present invention further relates to the use of the condensed heterocyclic compound of formula (I) as a pest control agent.

Background Art

[0002] Insecticides and acaricides currently in use must meet many requirements, such as the spectrum and level of efficacy, long-term activity, beneficial side effects, and their usability. Efforts have been made over the past few decades to develop selective insecticides that specifically act on biochemical mechanisms of action that exist only in insects or mites and further exhibit advantageous properties different from those of known insecticides.

[0003] Heterocyclic compounds having insecticidal activity are known and are described, for example, in WO2013191112.

[0004] However, when conventional pesticide spraying continues for several years, many pests acquire resistance and cannot be sufficiently controlled, and this difficult situation has been increasing in recent years. Furthermore, some of those existing control agents are very toxic or remain in the environment for a long time due to their residual properties and can cause serious problems due to the destruction of the ecosystem.

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

[0006] In view of the above, the present invention contemplates such compounds that meet or overcome the disadvantages associated with the prior art.

[0007] Surprisingly, it has now been found that certain novel control-active condensed heterocyclic compounds having a sulfur-containing substituent, which are the subject of the present invention, have desirable properties as a control agent.

SUMMARY OF THE INVENTION

[0008] Accordingly, the present invention provides a fused heterocyclic compound of formula (I) or an agriculturally acceptable salt, isomer / structural isomer, stereoisomer, diastereomer, enantiomer, tautomer, metal complex, polymorph, or N-oxide thereof:

[0009]

Chemical formula

[0010] Formula (I)

[0011] wherein, in the formula, Q, R 1 , R 2、 n, m and Y are as defined in the detailed description.

[0012] In one embodiment, the present invention provides a process for preparing a compound of formula (I) or an agriculturally acceptable salt thereof.

[0013] In another embodiment, the present invention provides a composition for controlling or preventing invertebrate pest animals, comprising a biologically effective amount of a compound of formula (I), an agriculturally acceptable salt, isomer / structural isomer, stereoisomer, diastereomer, enantiomer, tautomer, metal complex, polymorph, or N-oxide thereof, and at least one additional component selected from the group consisting of surfactants and adjuvants.

[0014] In yet another embodiment, the composition further comprises at least one additional biologically active and compatible compound selected from the group consisting of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers, or nutrients.

[0015] In yet another embodiment, the present invention provides the use of a compound of formula (I), an agriculturally acceptable salt thereof, an isomer / structural isomer, stereoisomer, diastereomer, enantiomer, tautomer, metal complex, polymorph, or N-oxide, a composition, or a combination thereof for controlling invertebrate pests or animal parasites in agricultural and / or horticultural crops.

[0016] In yet another embodiment, the present invention provides a method for controlling invertebrate pest animals, the method comprising contacting an invertebrate pest animal, its habitat, breeding ground, food supply, plant, seed, soil, area, material, or environment in which it grows or can grow, or a material, plant, seed, soil, surface, or space protected from pest attack or infestation with a biologically effective amount of a compound of formula (I) or an agriculturally acceptable salt thereof, an isomer / structural isomer, stereoisomer, diastereomer, enantiomer, tautomer, metal complex, polymorph, or N-oxide, a composition, or a combination thereof.

Embodiments for Carrying out the Invention

[0017] Definitions:

[0018] The definitions provided herein for the terms used in this disclosure are for illustrative purposes only and are in no way intended to limit the scope of the invention disclosed in this disclosure.

[0019] As used herein, the terms "comprises", "comprising", "includes", "including", "has", "having", "contains", "containing", "characterized by", or any other variation thereof are intended to cover non-exclusive inclusion, without any limitation being expressed. For example, a composition, mixture, process, or method comprising the recited components is not necessarily limited to only those components, and may include other components not expressly listed or specific to such composition, mixture, process, or method.

[0020] The transitional phrase "consisting of" excludes any unspecified elements, steps, or components. When in the claims, it closes the claims against the inclusion of materials other than those recited, except for impurities normally associated therewith. When the phrase "consisting of" appears in a clause of the body of the claims rather than immediately following the preamble, it limits only the components recited in that clause, and other components are not excluded from the claims as a whole.

[0021] The transitional phrase "consisting essentially of" is used to define a composition or method that includes, in addition to what is literally disclosed, materials, steps, features, elements, or components, provided that these additional materials, steps, features, elements, or components do not substantially affect the basic and novel characteristics of the invention recited in the claims. The term "consisting essentially of" takes a middle ground between "comprising" and "consisting of".

[0022] Furthermore, unless explicitly stated to the contrary, "or" refers to an inclusive "or" and not an exclusive "or". For example, the condition A "or" B is satisfied by any of the following: A is ○ (or present) and B is × (or absent), A is × (or absent) and B is ○ (or present), and both A and B are ○ (or present).

[0023] Also, the indefinite articles "a" and "an" preceding an element or component of the present invention are intended to be non-restrictive with respect to the number of instances of the element or component (i.e., occurrences). Thus, "a" or "an" should be read to include one or at least one, and the singular form of an element or component includes the plural as well, unless the number is clearly meant to be singular.

[0024] As referred to in the present disclosure, the term "invertebrate pest" includes arthropods, gastropods, and nematodes that are economically important as pests. The term "arthropod" includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs, and sow bugs. The term "gastropod" includes snails, slugs, and other stylommatophorans. The term "nematode" refers to organisms in the phylum Nematoda. The term "helminth" includes roundworms, dog heartworms, phytophagous nematodes (Nematoda), flukes (Tematoda), hookworms, tapeworms (Cestoda).

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

[0026] The term "nonagronomic" refers to applications other than agricultural crops, such as horticultural crops (e.g., greenhouse plants not grown in the field, nursery plants, or ornamental plants), residential, agricultural, commercial, and industrial structures, turf (e.g., turf farms, pastures, golf courses, lawns, sports fields), wood products, stored products, agroforestry and vegetation management, public health (i.e., humans) and animal health (e.g., domesticated animals such as pets, livestock, and poultry, non-domesticated animals such as wildlife).

[0027] For non - agricultural uses, it typically involves administering to a protected animal a parasitically effective (i.e., biologically effective) amount of a compound of the present invention in the form of a composition formulated for veterinary use, thereby protecting the animal from invertebrate parasitic pests. As referred to in this disclosure and the claims, the terms "parasiticidal" and "parasitically" refer to the observable effects on invertebrate parasitic pests for protecting animals from pests. The parasiticidal effect typically relates to a decrease in the occurrence or activity of the target invertebrate parasitic pests. Such effects on pests include necrosis, death, growth retardation, reduced mobility, or reduced ability to remain on or within the host animal, reduced feeding, and inhibition of reproduction. These effects on invertebrate parasitic pests provide control (including prevention, reduction, or elimination) of parasite invasion or infection of the animal.

[0028] The compounds of the present disclosure can exist in pure form or as mixtures of different possible isomeric forms such as stereoisomers or structural isomers. Various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformational isomers, rotational isomers, tautomers, optical isomers, polymorphs, and geometric isomers. Any desired mixture of these isomers is within the scope of the claims of the present disclosure. Those skilled in the art will understand that one stereoisomer may be more active and / or exhibit beneficial effects when concentrated or separated from other isomers. Furthermore, those skilled in the art know the processes or methods or techniques for separating, concentrating, and / or selectively preparing the above - mentioned isomers.

[0029] Here, the meanings of various terms used in this description are explained.

[0030] The term "aliphatic compound" or "aliphatic group" as used herein is an organic compound in which carbon atoms are linked in a straight - chain, branched - chain, or non - aromatic ring.

[0031] The term "alkyl", used alone or as part of a compound word such as "alkylthio" or "haloalkyl" or -N(alkyl) or alkylcarbonylalkyl or alkylsulfonylamino, etc., refers to straight-chain or branched C1-C 24 alkyl, preferably C1-C 15 alkyl, more preferably C1-C 10 alkyl, most preferably including C1-C6 alkyl. Representative examples of alkyl include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl, or different isomers are included. For example, when alkyl is at the end of a compound substituent, such as in alkylcycloalkyl, the cycloalkyl part of the compound substituent at the beginning may be mono- or polysubstituted independently, either identically or differently, by alkyl. The same applies to compound substituents with other groups, such as alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy, etc., at the end.

[0032] The term "alkenyl", used alone or as part of a compound word, refers to straight-chain or branched C2-C 24 alkene, preferably C2-C 15 alkene, more preferably C2-C 10It contains alkenes, most preferably C2 - 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, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-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, as well as different isomers are included. "Alkyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to complex substituents, such as alkenyl as part of, for example, haloalkenyl, unless otherwise specifically defined.,

[0033] The term "alkynyl", used either alone or as part of a compound word, refers to a straight-chain or branched C2-C 24 alkyne, preferably a C2-C 15 alkyne, more preferably a C2-C 10 alkyne, most preferably a C2-C6 alkyne. Non-limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 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-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-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, as well as different isomers are included. This definition also applies to complex substituents, such as alkynyl as part of, for example, haloalkynyl, unless otherwise specifically defined. The term "alkynyl" can also include moieties consisting of multiple triple bonds such as 2,5-hexadiynyl.,

[0034] The term "cycloalkyl" means an alkyl that is 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 complex substituent, such as cycloalkylalkyl, unless otherwise specifically defined.

[0035] The term "cycloalkenyl" means an alkenyl that is closed to form a ring containing a monocyclic partially unsaturated hydrocarbyl group. Non-limiting examples include, but are not limited to, cyclopropenyl, cyclopentenyl, and cyclohexenyl. This definition also applies to cycloalkenyl as part of a complex substituent, such as cycloalkenylalkyl, unless otherwise specifically defined.

[0036] The term "cycloalkynyl" means an alkynyl that is closed to form a ring containing a monocyclic partially unsaturated group. Non-limiting examples include, but are not limited to, cyclopropynyl, cyclopentynyl, and cyclohexynyl. This definition also applies to cycloalkynyl as part of a complex substituent, such as cycloalkynylalkyl, unless otherwise specifically defined.

[0037] Terms such as "cycloalkoxy", "cycloalkenyloxy", etc. are similarly defined. Non-limiting examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy, and cyclohexyloxy. This definition also applies to cycloalkoxy as part of a complex substituent, such as cycloalkoxyalkyl, unless otherwise specifically defined.

[0038] The term "halogen", whether alone or in a compound word such as "haloalkyl", includes fluorine, chlorine, bromine, or iodine. Further, when used in a compound word such as "haloalkyl", the alkyl may be partially or completely substituted with halogen atoms which may be the same or different. Non-limiting examples of "haloalkyl" include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl, and 1,1,1-trifluoropropan-2-yl. This definition also applies to haloalkyl as part of a complex substituent, such as haloalkylaminoalkyl, unless otherwise specifically defined.

[0039] The terms "haloalkenyl" and "haloalkynyl" are similarly defined, except that alkenyl and alkynyl groups are present as part of the substituent instead of an alkyl group.

[0040] The term "haloalkoxy" means a straight or branched alkoxy group in which some or all of the hydrogen atoms of the group 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-trifluoropropan-2-oxy. This definition also applies to haloalkoxy as part of a complex substituent, such as haloalkoxyalkyl, unless otherwise specifically defined.

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

[0042] Non-limiting examples of "haloalkylsulfinyl" include CF3S(O), CCl3S(O), CF3CH2S(O), and CF3CF2S(O). Examples of "haloalkylsulfonyl" include CF3S(O)2, CCl3S(O)2, CF3CH2S(O)2, and CF3CF2S(O)2.

[0043] The term "hydroxy" means -OH, amino means -NRR, where R can be any possible substituent such as H or alkyl. Carbonyl means -C(O)-, carbonyloxy means -OC(O)-, sulfinyl means SO, and sulfonyl means S(O)2.

[0044] The term "alkoxy", used either alone or as part of a compound word, means C1-C 24 alkoxy, preferably C1-C 15 alkoxy, more preferably C1-C 10 alkoxy, most preferably including C1-C6 alkoxy. Examples of alkoxy include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy, as well as different isomers. This definition also applies to alkoxy as part of a complex substituent, such as haloalkoxy, alkynylalkoxy, etc., unless otherwise specifically defined.

[0045] The term "alkoxyalkyl" indicates an alkoxy substitution on an alkyl. Non-limiting examples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2, and CH3CH2OCH2CH2.

[0046] The term "alkoxyalkoxy" indicates an alkoxy substitution on an alkoxy.

[0047] The term "alkylthio" refers to a branched or straight-chain alkylthio moiety, 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 1-ethyl-2-methylpropylthio, as well as different isomers.

[0048] Halocycloalkyl, halocycloalkenyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylcarbonyl, cycloalkylcarbonyl, haloalkoxylalkyl, etc. are defined in the same manner as the above examples.

[0049] The term "alkylthioalkyl" means an alkylthio substitution on an alkyl. Representative examples of "alkylthioalkyl" include -CH2SCH2, -CH2SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2, and CH3CH2SCH2CH2. "Alkylthioalkoxy" indicates an alkylthio substitution on an alkoxy. The term "cycloalkylalkylamino" indicates a cycloalkyl substitution on an alkylamino.

[0050] Terms such as alkoxyalkoxyalkyl, alkylaminoalkyl, dialkylaminoalkyl, cycloalkylaminoalkyl, cycloalkylaminocarbonyl, etc. are defined in the same manner as "alkylthioalkyl" or cycloalkylalkylamino.

[0051] The term "alkoxycarbonyl" is an alkoxy group bonded to the skeleton via a carbonyl group (-CO-). This definition also applies to alkoxycarbonyl as part of a complex substituent, such as cycloalkylalkoxycarbonyl, etc., unless otherwise specifically defined.

[0052] The term "alkoxycarbonylalkylamino" indicates an alkoxycarbonyl substitution on an alkylamino. "Alkylcarbonylalkylamino" indicates an alkylcarbonyl substitution on an alkylamino. Terms such as alkylthioalkoxycarbonyl, cycloalkylalkylaminoalkyl, etc. are defined in the same manner.

[0053] Non-limiting examples of "alkylsulfinyl" include methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl, and 1-ethyl-2-methylpropylsulfinyl, and different isomers are included, but not limited thereto. The term "arylsulfinyl" includes Ar-S(O), where Ar can be any carboxyl or heterocyclic ring. This definition also applies to composite substituents, such as alkylsulfinyl as part of, for example, haloalkylsulfinyl, unless otherwise specifically defined.

[0054] Non-limiting examples of "alkylsulfonyl" include methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl, and 1-ethyl-2-methylpropylsulfonyl, and include, but are not limited to, different isomers. The term "arylsulfonyl" includes Ar-S(O)2, where Ar can be any carboxyl or heterocyclic ring. This definition also applies to alkylsulfonyl as part of a complex substituent, such as alkylsulfonylalkyl, etc., unless otherwise defined.

[0055] "Alkylamino", "dialkylamino", etc. are defined in the same manner as the above examples.

[0056] The term "carbocyclic" includes "aromatic carbocyclic ring systems" and "non-aromatic carbocyclic ring systems", or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds where the ring may be aromatic or non-aromatic (aromatic indicates satisfying the Hückel rule, and non-aromatic indicates not satisfying the Hückel rule).

[0057] Non-limiting examples of non-aromatic carbocyclic systems include cyclopropyl, cyclobutyl, cyclopentyl, norbornyl, etc. Non-limiting examples of aromatic carbocyclic systems include phenyl, naphthyl, etc.

[0058] As used herein, the term "aryl" includes, but is not limited to, any carbon-based aromatic group including phenyl, naphthalene, biphenyl, anthracene, etc. An aryl group may be substituted or unsubstituted. Further, an aryl group may be a single ring structure, a fused ring structure, or a structure consisting of a plurality of ring structures bonded via one or more bridging groups such as carbon-carbon bonds.

[0059] The term "aryl" also includes "aralkyl" and refers to an aryl hydrocarbon radical containing an alkyl moiety as defined above. Examples include benzyl, phenylethyl, and 6-naphthylhexyl. As used herein, the term "aralkenyl" means an aryl hydrocarbon radical containing an alkenyl moiety as defined above and an aryl moiety as defined above. Examples include styryl, 3-(benzyl)prop-2-enyl, and 6-naphthylhexyl-2-enyl.

[0060] The term "hetero" in relation to a ring refers to a ring that can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, where at least one ring atom is not carbon (provided that each ring contains no more than 4 nitrogens, 2 oxygens, and 2 sulfurs).

[0061] The term "aromatic" indicates that it satisfies Hückel's rule, and the term "non-aromatic" indicates that it does not satisfy Hückel's rule.

[0062] The terms "heterocyclic ring" or "heterocyclic" or "heterocyclic ring system" include "aromatic heterocyclic ring" or "heteroaryl bicyclic ring system" and "non-aromatic heterocyclic ring system", or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds where the ring may be aromatic or non-aromatic, where the heterocyclic ring contains at least one heteroatom selected from N, O, S(O) 0~2 and / or the ring members of the heterocyclic ring are C(=O), C(=S), C(=CR * R * ), and C=NR * and may be replaced by, * wherein

[0063] The term "non-aromatic heterocyclic" or "non-aromatic heterocyclic ring" means the following: a saturated or partially unsaturated heterocyclic ring containing 1 to 4 heteroatoms from the group of oxygen, nitrogen, and sulfur, having 3 to 15 members, preferably 3 to 12 members; a monocyclic, bicyclic, or tricyclic heterocyclic ring containing, in addition to carbon ring members, 1 to 3 nitrogen atoms and / or 1 oxygen or sulfur atom or 1 or 2 oxygen and / or sulfur atoms (when there are 2 or more oxygen atoms in the ring, they are not directly adjacent); for example (but not limited to), oxetanyl, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 1-imidazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-1-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-1-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, pyrrolinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, pyrazinyl, morpholinyl, thiomorpholinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl,3-Hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl, 1,2,4-hexahydrotriazin-3-yl, cycloserine, 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, tetra- and hexahydrooxepinyl, for example, 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 as part of a complex substituent, such as heterocyclylalkyl, etc., unless otherwise specifically defined.,

[0064] The term "heteroaryl" or "aromatic heterocyclic" means the following: a 5- or 6-membered fully unsaturated monocyclic ring system containing 1 to 4 heteroatoms from the group of oxygen, nitrogen, and sulfur (wherein, when a plurality of oxygen atoms are contained in the ring, they are not directly adjacent): a 5-membered heteroaryl containing 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur or oxygen atom: a 5-membered heteroaryl group which may contain, in addition to carbon atoms, 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 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; a nitrogen-bonded 5-membered heteroaryl containing 1 to 4 nitrogen atoms, or a benzo-fused nitrogen-bonded 5-membered heteroaryl containing 1 to 3 nitrogen atoms: a 5-membered heteroaryl group which may contain, in addition to carbon atoms, 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms as ring members, and wherein two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member may be bridged by a buta-1,3-diene-1,4-diyl group in which 1 or 2 carbon atoms may be replaced by nitrogen atoms, and these rings are bonded to the skeleton via one of the nitrogen ring members, such as (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.

[0065] A 6-membered heteroaryl containing 1 to 4 nitrogen atoms: In addition to carbon atoms, for example, a 6-membered heteroaryl group that may contain 1 to 3 and 1 to 4 nitrogen atoms respectively as ring members, such as (but not limited to) 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; A benzo-fused 5-membered heteroaryl containing 1 to 3 nitrogen atoms or 1 nitrogen atom and 1 oxygen or sulfur atom: For example (but not limited to), indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, indazol-1-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl, indazol-7-yl, indazol-2-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1-benzothiophen-6-yl, 1-benzothiophen-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl, and 1,3-benzoxazol-7-yl;Benzofused 6-membered heteroaryl containing 1 to 3 nitrogen atoms: for example (but not limited to) quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, and isoquinolin-8-yl. This definition also applies to heteroaryl as part of a complex substituent, such as heteroarylalkyl, etc., unless otherwise specifically defined.;

[0066] Bicyclic 5-6 heteroaryl system having 1 to 3 nitrogen atoms or a nitrogen atom serving as a bridgehead (ring-bonding part) containing 1 nitrogen atom and 1 oxygen or sulfur atom: for example (but not limited to) imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine, [1,2,4]triazolo[1,5-a]pyrimidine, [1,2,4]triazolo[1,5-b]pyridazine, [1,2,4]triazolo[1,5-a]pyrazine, [1,2,4]triazolo[1,5-a]pyridine, imidazo[1,2-c]pyrimidine, imidazo[1,2-b]pyridazine, [1,2,4]triazolo[1,5-c]pyrimidine, 1-methyl-1H-indole, imidazo[1,2-a]pyrazine, pyrazolo[1,5-a]pyridine, [1,2,4]triazolo[4,3-a]pyridine.

[0067] The term "trialkylsilyl" includes three branched and / or straight-chain alkyl groups bonded to and linked through a silicon atom, such as trimethylsilyl, triethylsilyl, and t-butyl-dimethylsilyl. "Halotrialkylsilyl" indicates that at least one of the three alkyl groups is partially or fully substituted with a halogen atom, which may be the same or different. The term "alkoxytrialkylsilyl" indicates that at least one of the three alkyl groups is substituted with one or more alkoxy groups, which may be the same or different. The term "trialkylsilyloxy" indicates a trialkylsilyl moiety bonded through oxygen.

[0068] 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 different butoxy- or pentyloxycarbonyl isomers. Non-limiting examples of "alkylaminocarbonyl" include CH3NHC(=O), CH3CH2NHC(=O), CH3CH2CH2NHC(=O), (CH3)2CHNHC(=O), and different butylamino- or pentylaminocarbonyl isomers. Non-limiting examples of "dialkylaminocarbonyl" include (CH3)2NC(=O), (CH3CH2)2NC(=O), CH3CH2(CH3)NC(=O), CH3CH2CH2(CH3)NC(=O), and (CH3)2CHN(CH3)C(=O). Non-limiting examples of "alkoxyalkylcarbonyl" include CH3OCH2C(=O), CH3OCH2CH2C(=O), CH3CH2OCH2C(=O), CH3CH2CH2CH2OCH2C(=O), and CH3CH2OCH2CH2C(=O). Non-limiting examples of "alkylthioalkylcarbonyl" include CH3SCH2C(=O), CH3SCH2CH2C(=O), CH3CH2SCH2C(=O), CH3CH2CH2CH2SCH2C(=O), and CH3CH2SCH2CH2C(=O). Terms such as haloalkylsulfonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkylamino are defined similarly.

[0069] Non-limiting examples of "alkylaminoalkylcarbonyl" include CH3NHCH2C(=O), CH3NHCH2CH2C(=O), CH3CH2NHCH2C(=O), CH3CH2CH2CH2NHCH2C(=O), and CH3CH2NHCH2CH2C(=O).

[0070] The term "amide" means A-R’C=ONR’R’’-B, where R’ and R’’ represent substituents, and A and B represent any groups.

[0071] The term "thioamide" means A-R’C=SNR’R’’-B, where R’ and R’’ represent substituents, and A and B represent any group.

[0072] The total number of carbon atoms in the substituent is indicated by the prefix "C i ~C j ", where i and j are numbers from 1 to 21. For example, C1-C3 alkylsulfonyl represents from methylsulfonyl to propylsulfonyl, C2 alkoxyalkyl represents CH3OCH2, C3 alkoxyalkyl represents, for example, CH3CH(OCH3), CH3OCH2CH2, or CH3CH2OCH2, and C4 alkoxyalkyl represents various isomers of an alkyl group substituted with an alkoxy group containing a total of 4 carbon atoms, including, for example, CH3CH2CH2OCH2 and CH3CH2OCH2CH2. In the above description, when the compound of formula (I) consists of one or more heterocycles, all substituents are attached to these rings via any available carbon or nitrogen by replacing the hydrogen on the above carbon or nitrogen.

[0073] When the compound is substituted with a substituent having a subscript indicating that the number of the above substituents can exceed 1, the substituent(s), when there are more than 1, are independently selected from the group of defined substituents. Further, when the subscript m of (R) m indicates an integer in the range of, for example, 0 to 4, the number of substituents can be selected from integers from 0 to 4.

[0074] When a substituent contains a substituent that can be hydrogen, it is recognized that the group is unsubstituted when this substituent is hydrogen.

[0075] Embodiments of the present specification, as well as their various features and advantageous details, are described with reference to non-limiting embodiments in this description. To avoid unnecessarily obscuring the embodiments of the present specification, descriptions of well-known components and processing techniques are omitted. The examples used in this specification are merely intended to facilitate the understanding of how the embodiments of the present specification can be implemented and to further enable those skilled in the art to implement the embodiments of the present specification. Therefore, the examples should not be construed as limiting the scope of the embodiments of the present specification.

[0076] The description of specific embodiments clearly reveals the general nature of the embodiments in this specification. Thus, others can, by applying current knowledge, easily modify and / or adapt such specific embodiments to various applications without departing from the general concept. Therefore, such adaptations and modifications should be intended to be within the meaning and scope of the equivalents of the disclosed embodiments and are indeed intended. It should be understood that the terms or technical terms used in this specification are for the purpose of explanation and not for the purpose of limitation. Therefore, although the embodiments of the present specification are described with respect to preferred embodiments, those skilled in the art will recognize that the embodiments of the present specification can be implemented with modifications within the spirit and scope of the embodiments described in this specification.

[0077] Any discussion of any document, act, material, device, paper, etc. included in this specification is only for the purpose of providing relevance for the disclosure. None of these matters, either individually or in combination, should be regarded as admitting that they formed part of the prior art base or were common general knowledge in the field related to this disclosure because they existed prior to the priority date of this application.

[0078] The numerical values described in this description and in the description / claims may form an important part of the present invention, but deviations from such numerical values are still considered to be within the scope of the present invention if such deviations follow the same scientific principles as the scientific principles of the present invention disclosed in the present invention. The inventive compounds of the present invention may, where appropriate, exist as mixtures of different possible isomeric forms, in particular as mixtures of stereoisomers, such as E and Z, threo and erythro, and as mixtures of optical isomers, but may, where appropriate, exist as mixtures of tautomers. Both the E and Z isomers, as well as the threo and erythro isomers, and the optical isomers, any desired mixtures of these isomers, and possible tautomers are disclosed and claimed.

[0079] For the purposes of the present disclosure, the term "pest" includes, but is not limited to, fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, insects, and rodents. Pests are also animals and plants that are harmful to human or human concerns including crops, livestock, and forestry.

[0080] The term "plant" as used herein is understood to mean all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants obtained by conventional breeding and optimization methods, or by biotechnological and genetic engineering methods, or combinations of these methods, and include transgenic plants as well as plant cultivars that can and cannot be protected by plant breeder's rights.

[0081] For the purposes of the present disclosure, the term "plant" typically includes organisms of the type exemplified by trees, shrubs, herbs, grasses, ferns, and mosses that grow in a location, absorb water and necessary substances from their roots, and synthesize nutrients in their leaves by photosynthesis.

[0082] Examples of "plants" for the purposes of the present invention include agricultural crops such as wheat, rye, barley, triticale, oats, or rice; beets such as sugar beets or fodder beets; fruits and fruit trees such as pome fruits, stone fruits, or soft fruits such as apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries, or gooseberries; leguminous plants such as lentils, peas, alfalfa, soybeans; oil plants such as rapeseed, mustard, olive, sunflower, coconut, cocoa beans, sesame, oil palm, peanut, or soybean; cucurbits such as pumpkins, cucumbers, or melons; fiber plants such as cotton, flax, hemp, or jute; citrus fruits and citrus trees such as oranges, lemons, grapefruits, or mandarins; any horticultural plant, vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, gourds, or paprika; laurel family plants such as avocados, cinnamon, or camphor; cucurbitaceae; oleaginous plants; energy and raw material plants such as cereals, corn, soybeans, other leguminous plants, rapeseed, sugarcane, or oil palm; tobacco; nuts; coffee; tea; cocoa; bananas; pepper; grapevines (edible grapes and grape juice, wine); hops; turf; sweet leaves (also referred to as stevia); natural rubber plants or ornamental plants and forest plants such as flowers, shrubs, broadleaf trees, or evergreens such as conifers; plant propagation material such as seeds, and crop material of these plants, but are not limited thereto.

[0083] Preferably, plants for the purposes of the present invention include cereals, corn, rice, soybeans, and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus fruits and citrus trees, any horticultural plant, cucurbits, oil plants, tobacco, coffee, tea, cocoa, sugarcane, sugar beets, cotton, potatoes, tomatoes, onions, pepper, and vegetables, ornamental plants, any flower-growing plant, and other plants for human and animal use, but are not limited thereto.

[0084] The term "plant part" is understood to mean all parts and organs of plants, above and below ground. For the purposes of the present disclosure, the term "plant part" includes, but is not limited to, cuttings, leaves, shoots, tubers, flowers, seeds, branches, taproots, lateral roots, root hairs, root tips, root caps, roots including rhizomes, slips, new shoots, fruits, fruit bodies, bark, stems, buds, axillary buds, meristems, nodes and internodes.

[0085] The term "in situ" includes the soil, the surroundings of the plant or plant part, and the equipment or apparatus used before, during, or after sowing / planting the plant or plant part.

[0086] The application of the compounds of the present disclosure or compositions comprising the compounds of the present disclosure optionally together with other compatible compounds to plants or plant material or in situ includes applications by techniques known to those skilled in the art including, but not limited to, spraying, coating, dipping, fumigating, impregnating, injecting, and dusting.

[0087] The term "applied" means physically or chemically adhering to the plant or plant part, including impregnating.

[0088] In one embodiment, the invention provides a compound of formula (I):

[0089]

Chemical formula

[0090] Formula (I)

[0091] wherein

[0092] R 1 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, and C3-C8-cycloalkyl-C1-C6-alkyl;

[0093] Y is independently selected from O or NR Y ;

[0094] R Y is selected from the group consisting of hydrogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C3-C5-cycloalkyl, and C3-C5-cycloalkyl-C1-C3-alkyl;

[0095] R 2 is halogen, cyano, nitro, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, C1-C6-cyanoalkyl, OR 4 、NR 5 R 6 、CR 4 =NR 5 、C(=O)R 8 、S(O) 0-2 R 7 、SCN、S(O) 0-1 R 9 =NR 10 、N=S(O) 0-1 (R 9 )2、P(=O)(OR’’)2、Si(R’)3、C6-C 10 -aryl, C7-C 14 -aralkyl and C3-C 10 -heterocyclyl; where each group of R 2 is optionally substituted with one or more groups of R 2a ;

[0096] R 2a is halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR 4 、NR 5 R 6 、CR 4 =NR 5 、C(=O)R 8 、S(O) 0-2R 7 , SCN, S(O) 0-1 R 9 =NR 10 , N=S(O) 0-1 (R 9 )2, Si(R’)3, C6~C 10 -aryl, C7~C 14 -aralkyl and C3~C 10 -heterocyclyl selected from the group consisting of; wherein, R 2a is optionally substituted with one or more R 2aa ;

[0097] or

[0098] Two R 2a substituents, together with the atom to which they are attached, or selected from the group consisting of C, N, O, S, and optionally C(=O), C(=S), S(O) 0-2 and Si(R’)2, may further form a 3- to 7-membered ring with additional atoms containing 1 to 3 ring members selected from the group consisting of, and this ring may optionally be substituted with one or more R 2aa groups on that portion;

[0099] R 2aa is halogen, cyano, C1~C6-alkyl, C2~C6-alkenyl, C2~C6-alkynyl, C1~C6-haloalkyl, C2~C6-haloalkenyl, C3~C8-cycloalkyl, OR 4 , NR 5 R 6 , C(=O)R 8 , S(O) 0-2 R 7 , S(O) 0-1 R 9 =NR 10 , N=S(O) 0-1 (R 9 )2, Si(R’)3, C6~C 10 -aryl, C7~C 14 -aralkyl and C3~C 10 -heterocyclyl selected from the group consisting of;

[0100] Q is a radical selected from the group consisting of formulae Q1, Q2, Q3, Q4, and Q5, optionally substituted with one or more R 3 and R 3’ ;

[0101]

Chemical formula

[0102] provided that Q is attached to the C2 or C5 carbon of the pyridine ring;

[0103] R 3 is hydrogen, halogen, cyano, nitro, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR 4 NR 5 R 6 CR 4 =NR 5 C(=O)R 8 S(O) 0-2 R 7 SCN, S(O) 0-1 R 9 =NR 10 N=S(O) 0-1 (R 9 )2, P(=O)(OR'')2, Si(R')3, C6-C 10 -aryl, C7-C 14 -aralkyl and C3-C6-heterocyclyl, where each group of R 3 is optionally substituted with one or more groups of R 3a ;

[0104] R 3a is halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR 4 NR 5 R 6 C(=O)R 8 S(O) 0-2 R 7, S(O) 0-1 R 9 =NR 10 , N=S(O) 0-1 (R 9 )2, Si(R’)3, C6~C 10 -aryl, C7~C 14 -aralkyl and C3~C 10 -heterocyclyl selected from the group consisting of;

[0105] R 3’ is selected from the group consisting of hydrogen, halogen, cyano, C1~C6-alkyl, C2~C6-alkenyl, C2~C6-alkynyl, C1~C6-haloalkyl, C3~C8-cycloalkyl, OR’’ and N(R’’)2; where each group of R 3’ is optionally substituted by one or more groups of R 3a’ ;

[0106] R 3a’ is selected from the group consisting of halogen, cyano, C3~C8-cycloalkyl, OR’’ and N(R’’)2;

[0107] R 4 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)2R 7 , Si(R’)3, C6~C 10 -aryl, C7~C 14 -aralkyl and C3~C 10 -heterocyclyl selected from the group consisting of; each group of R 4 is optionally substituted by R 4a ;

[0108] R 4a is selected from the group consisting of halogen, cyano, C1~C6-alkyl, C2~C6-alkenyl, C2~C6-alkynyl, C1~C6-haloalkyl, C2~C6-haloalkenyl, C3~C8-cycloalkyl, OR’, NR’R’’, S(O) 0-2 R’, C(=O)R’, Si(R’)3, C6~C 10 -aryl, C7~C14 - selected from the group consisting of aralkyl and C3-C 10 - heterocyclyl;

[0109] R 5 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR 4 , NR’R’’, S(O) 0-2 R 7 , C(=O)R 8 , Si(R’)3, C6-C 10 - aryl, C7-C 14 - aralkyl, C3-C 10 - heterocyclyl; where each group of R 5 is optionally substituted by R 5a ;

[0110] R 5a is halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR’, NR’R’’, S(O) 0-2 R’, C(=O)R’, Si(R’)3, C6-C 10 - aryl, C7-C 14 - aralkyl, and C3-C 10 - heterocyclyl;

[0111] R 6 is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-cycloalkyl, and C(=O)R 8 ;

[0112] R 7 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, NR 5 R6 and C6-C 10 -aryl, C7-C 14 -aralkyl and C3-C 10 -heterocyclyl, selected from the group consisting of; each R 7 group may optionally be substituted with one or more R 7a groups;

[0113] R 7a is halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR’, NR’R’’, S(O) 0-2 R’, C(=O)R’, C6-C 10 -aryl, C7-C 14 -aralkyl and C3-C 10 -heterocyclyl, selected from the group consisting of;

[0114] R 8 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR 4 , NR 5 R 6 , N=S(O) 0-1 (R 9 )2, C6-C 10 -aryl, C7-C 14 -aralkyl and C3-C 10 -heterocyclyl, selected from the group consisting of; wherein each R 8 group is optionally substituted with one or more R 8a groups;

[0115] R 8a is halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR’, NR’R’’, S(O) 0-2 R’, C(=O)R’, C6-C 10 -aryl, C7-C 14- selected from the group consisting of aralkyl and C3-C 10 - heterocyclyl;

[0116] R 9 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, and C(=O)R 8 ;

[0117] R 10 is selected from the group consisting of hydrogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, Si(R')3, S(O) 0~2 R 7 , and C(=O)R 8 ;

[0118] Two R 9 substituents, or R 9 and R 10 substituents, together with the atoms to which they are attached, or selected from the group consisting of C, N, O, S; optionally including 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O) 0-2 and Si(R')2, may form a 4- to 7-membered ring together with additional atoms, and the moiety may optionally be R' substituted with one or more groups;

[0119] R' can be selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, OR'', N(R'')2, S(O) 0-2 R'', C(=O)R'', C(=O)OR'', and C(=O)N(R'')2.

[0120] R'' is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, and C3-C8-cycloalkyl; where each group of R'' is optionally substituted with halogen;

[0121] R 1 ~R 10 、R Y 、R 2a 、R 2aa 、R 3a 、R 3a’ 、R 4a 、R 5a 、R 7a and R 8a Each of the groups is optionally substituted by one or more groups selected from the group consisting of X, CN, R’, OR’, SR’, N(R’)2, COOR’ and CON(R’)2;

[0122] ‘‘n’’ is an integer from 0 to 1;

[0123] ‘‘m’’ is an integer in the range from 0 to 3;

[0124] or an agriculturally acceptable salt, isomer / structural isomer, stereoisomer, diastereoisomer, enantiomer, tautomer, polymorph, metal complex, N-oxide or S-oxide thereof is provided.

[0125] In a preferred embodiment, Q is of the formula Q 1a 、Q 1b 、Q 2a 、Q 2ba 、Q3、Q 4a 、Q 4b 、and Q5.

[0126]

Chemical Formula

[0127] where

[0128] R 3 and R 3’ are the same as those defined above.

[0129] In a particular embodiment, Q is of the formula Q 1a or Q 1bis selected from the group consisting of.

[0130]

Chemical formula

[0131] and is, where

[0132] R 3 and R 3’ are the same as those defined above.

[0133] In another embodiment, the compound of formula (I) is represented by a compound of formula (Ia).

[0134]

Chemical formula

[0135] Formula (Ia)

[0136] where R 1 , R 2 , Q, Y, n and m are the same as those defined above herein.

[0137] In yet another embodiment, the compound of formula (I) is represented by a compound of formula (Ib).

[0138]

Chemical formula

[0139] Formula (Ib)

[0140] where R 1 , R 2 , Q, Y, n and m are the same as those defined above herein.

[0141] In a preferred embodiment, the compound of formula (Ia) is represented by a compound of formula (Iaa).

[0142] [Chemical formula]

[0143] Here, R 1 , R 2 , Q, and m are the same as those defined above in this specification.

[0144] In a preferred embodiment, the compound of formula (Ia) is represented by the compound of formula (Iab).

[0145] [Chemical formula]

[0146] Here, R 1 , R 2 , Q, Y, n, and m are the same as those defined above in this specification.

[0147] In another preferred embodiment, the compound of formula (Ib) is represented by the compound of formula (Iba).

[0148] [Chemical formula]

[0149] Here, R 1 , R 2 , Q, Y, n, and m are the same as those defined above in this specification.

[0150] In another preferred embodiment, the compound of formula (Ib) is represented by the compound of formula (Ibb).

[0151] [Chemical formula]

[0152] Here, R 1 , R 2, Q, Y, n, and m are the same as those defined above in the present specification.

[0153] In another preferred embodiment, the compound of formula (Ib) is represented by the compound of formula (Ia-Q 1a ).

[0154] [Chemical formula] ;

[0155] wherein R 1 , R 2 , R 3 , Y, and m are the same as those defined above in the present specification.

[0156] In one embodiment, in particular; the compound of formula (I) is selected from the following, <Compound number 1> 5-(6-Chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound number 2> 5-(3-(Ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound number 3> 5-(3-(Ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound number 4> 5-(3-(Ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound number 5> 5-(6-(3,5-Dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 6> 7-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine; <Compound Number 7> 4-(4-Chlorophenyl)-2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one; <Compound Number 8> 4-(3,5-Dichlorophenyl)-2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one; <Compound Number 9> 5-(Ethylsulfonyl)-N-(4-(trifluoromethoxy)phenyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound Number 10> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-4-(4-(trifluoromethoxy)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one; <Compound Number 11> 7-(5-Bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 12> 7-(5-Bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 13> 7-(5-(3,5-Dichlorophenyl)-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 14> 7-(3-(Ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 15> 5-(3-(Ethylsulfonyl)-6-phenylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 16> 5-(3-(Ethylsulfonyl)-6-(4-fluorophenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 17> 5-(3-(Ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 18> 4-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)benzonitrile; <Compound No. 19> 5-(3-(Ethylsulfonyl)-6-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 20> 5-(6-(4-Chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 21> 5-(3-(Ethylsulfonyl)-6-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 22> 5-(3-(Ethylsulfonyl)-6-(3-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 23> 3-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)benzonitrile; <Compound No. 24> 5-(5-Bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 25> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one; <Compound No. 26> 5-(6-(3-Chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 27> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one; <Compound No. 28> 5-(3-(Ethylsulfonyl)-6-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 29> 5-(5-Bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 30> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-7-((trifluoromethyl)thio)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one; <Compound No. 31> 5-(5-(Ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 32> 5-(3-(Ethylthio)-5-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 33> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-7-((trifluoromethyl)sulfonyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one; <Compound No. 34> 5-(3-(Ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 35> 6-(6-Chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 36> 6-(6-Chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 37> 5-(5-(Ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 38> 5-(3-(Ethylsulfonyl)-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 39> 5-(5-(Ethylsulfonyl)-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 40> 6-(3-(Ethylthio)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 41> 5-(3-(Ethylsulfonyl)-6-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 42> 6-(3-(Ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 43> 6-(3-(Ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 44> 6-(3-(Ethylsulfonyl)-6-(4-fluoro-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 45> 6-(3-(Ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 46> 6-(6-(4-Bromo-1H-imidazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 47> 6-(6-(4-Chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 48> 6-(6-(3,5-Dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 49> 4-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)pyridin-2-yl)benzonitrile; <Compound No. 50> 6-(3-(Ethylsulfonyl)-6-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound Number 51> 6-(3-(Ethylsulfonyl)-6-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound Number 52> 6-(3-(Ethylsulfonyl)-6-(3-methyl-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 53> 6-(6-(3-Bromo-1H-1,2,4-triazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 54> 6-(3-(Ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 55> 6-(3-(Ethylsulfonyl)-6-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 56> 6-(6-(4-Chloro-1H-pyrazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 57> 5-(3-(Ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 58> 6-(3-(Ethylsulfonyl)-6-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound Number 59> 6-(3-(Ethylsulfonyl)-6-(1-methyl-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 60> 6-(3-(Ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 61> 5-(6-Chloro-5-(ethylthio)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 62> 5-(5-(Ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 63> 5-(3-(Ethylthio)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 64> 5-(6-Chloro-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 65> 6-(3-(Ethylsulfonyl)-6-(1H-1,2,3-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 66> 5-(3-(Ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 67> 5-(3-(Ethylthio)-5-(1-methyl-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 68> 6-(5-(Ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound Number 69> 5-(3-(Ethylsulfonyl)-5-(3-methyl-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 70> 5-(3-(Ethylsulfonyl)-5-(4-fluoro-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 71> 5-(3-(Ethylsulfonyl)-5-(1-methyl-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 72> 5-(5-(Ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 73> 5-(5-(Ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 74> 5-(5-(Ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 75> 2-(3-(Ethylsulfonyl)-5-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one; <Compound Number 76> 5-(5-(3,5-Dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 77> 5-(5-(3,5-Dichlorophenyl)-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 78> 5-(3-(Ethylsulfonyl)-5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 79> 2-(3-(Ethylsulfonyl)-5-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one; <Compound Number 80> 4-(4-Chlorophenyl)-2-(3-(ethylsulfonyl)-5-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one; <Compound Number 81> 6-(6-Chloro-5-(ethylthio)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 82> (5-Bromo-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(ethyl)(imino)-l6-sulfanone; <Compound Number 83> 5-(5-(Ethylsulfonyl)-6-(3-methyl-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 84> 5-(5-(Ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 85> 5-(6-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 86> ((5-(Ethylthio)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)dimethyl-l6-sulfanone; <Compound Number 87> ((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)dimethyl-l6-sulfanone; <Compound Number __> 6-(5-(Ethylsulfonyl)-6-(3-methyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)imidazo[1,2-a]pyrimidine; <Compound Number 88> 5-(5-(4-Bromo-1H-pyrazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 89> 5-(5-(4-Chloro-1H-pyrazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 90> 5-(5-Bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound Number 91> 6-(5-Bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 92> 6-(5-Bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 93> 6-(6-Chloro-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 94> 5-(3-(Ethylsulfonyl)-5-(4-fluorophenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 95> 5-(3-(Ethylsulfonyl)-5-(pyrimidin-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 96> 5-(3-(Ethylsulfonyl)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 97> 5-(3-(Ethylsulfonyl)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 98> Ethyl(imino)(5-(4-(trifluoromethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanone; <Compound No. 99> 5-(5-Bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 100> 5-(3-(Ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 101> 5-(5-(4-Chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 102> 5-(5-(3,5-Dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 103> 5-(5-(3,5-Difluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 104> 5-(3-(Ethylsulfonyl)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 105> 5-(3-(Ethylsulfonyl)-5-(4-fluorophenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 106> ((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)dimethyl-16-sulfanone; <Compound No. 107> Diethyl((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)-16-sulfanone; <Compound No. 108> Ethyl((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)(methyl)-16-sulfanone; <Compound No. 109> 5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-ol; <Compound No. 110> 6-(3-(Ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 111> 5-(5-(3-Chloro-5-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 112> 2-(5-Bromo-3-(ethylthio)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 113> 2-(5-Bromo-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound Number 114> 6-(3-(Ethylsulfonyl)-5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 115> Diethyl ((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)-16-sulfanone; <Compound Number 116> Ethyl ((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)(methyl)-16-sulfanone; <Compound Number 117> 2-(3-(Ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound Number 118> 2-(3-(Ethylsulfonyl)-5-(4-fluorophenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound Number 119> 2-(3-(Ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound Number 120> 2-(3-(Ethylsulfonyl)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound Number ___> 6-(5-(4-Chloro-3-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-1-methyl-3-(trifluoromethyl)-1,6-dihydro-7H-pyrazolo[3,4-d]pyridazin-7-one; <Compound Number 121> 2-(3-(Ethylsulfonyl)-5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound Number 122> 2-(5-(3,5-Difluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound Number 123> 2-(5-(4-Chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound Number 124> 2-(5-(4-Chloro-3-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound Number 125> 5-(5-(3,5-Difluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 126> 5-(5-(4-Chloro-3-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 127> 5-(5-(3-Chloro-4-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number 128> 2-(5-(3,5-Dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound Number 129> 2-(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound Number 130> 2-(3-(ethylsulfonyl)-5-(3-methyl-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound Number 131> 2-(5-(3-Chloro-5-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 132> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)thiazole; <Compound No. 133> 5-(3-(Ethylsulfonyl)-5-(1-methyl-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 134> 5-(3-(Ethylsulfonyl)-5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 135> 5-(3-(Ethylsulfonyl)-5-(pyrimidin-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 136> 5-(5-Cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 137> 6-(6-(3-Chloro-5-fluorophenyl)-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 138> 5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinonitrile; <Compound No. 139> Diethyl ((5-(ethylsulfonyl)-6-(9-methyl-8-(trifluoromethyl)-9H-purin-2-yl)pyridin-3-yl)imino)-1,6-sulfanone; <Compound No. 140> 5-(3-(Ethylsulfonyl)-6-(3-fluoro-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 141> N-Cyclopropyl-5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 142> 5-(5-Cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 143> 5-(3-(Ethylsulfonyl)-5-(2-methoxypyrimidin-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 144> 5-(3-(Ethylsulfonyl)-5-(3-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 145> 5-(3-(Ethylsulfonyl)-5-(3-methyl-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 146> 5-(3-(Ethylsulfonyl)-5-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 147> 5-(5-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 148> 5-(5-(3-Chloro-1H-1,2,4-triazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 149> ((5-(Ethylsulfonyl)-6-(9-methyl-8-(trifluoromethyl)-9H-purin-2-yl)pyridin-3-yl)imino)dimethyl-l6-sulfanone; <Compound No. 150> 5-(Ethylsulfonyl)-6-(9-methyl-8-(trifluoromethyl)-9H-purin-2-yl)pyridin-3-ol; <Compound No. 151> 5-(3-(Ethylsulfonyl)-5-methylpyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 152> 5-(3-(Ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 153> 5-(3-(Ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 154> 6-(5-(Ethylsulfonyl)-6-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 155> 5-(5-(3,4-Dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 156> 5-(3-(Ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 157> 2-(3-(Ethylsulfonyl)-5-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 158> 5-(3-(Ethylsulfonyl)-5-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 159> 5-(6-Chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 160> 5-(3-(Ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 161> 5-(5-(Cyclopropylmethoxy)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 162> 5-(5-(4-Chloro-3-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 163> 5-(5-(3,4-Dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 164> 5-(3-(Ethylsulfonyl)-5-methylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 165> 5-(6-Chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 166> 5-(Ethylsulfonyl)-N,N-dimethyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 167> 5-(Ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 168> N-Cyclopropyl-5-(ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 169> 5-(6-Chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 170> N-Cyclopropyl-5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine; <Compound No. 171> 5-(6-Cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 172> ((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-l6-sulfanone; <Compound No. 173> 5-(3-(Ethylsulfonyl)-6-(prop-1-yn-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 174> 5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 175> N-Cyclopropyl-5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 176> N-Cyclopropyl-5-(ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 177> 5-(5-(3-Bromo-1H-1,2,4-triazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 178> 5-(3-(Ethylsulfonyl)-5-(prop-1-yn-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 179> ((5-(Ethylthio)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-l6-sulfanone; Compound No. 180 5-(6-Cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; Compound No. 181 5-(3-(Ethylthio)-6-methylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; Compound No. 182 5-(3-(Ethylsulfonyl)-6-methylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; Compound No. 183 5-(3-(Ethylsulfonyl)-6-methylpyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; Compound No. 184 ((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-sulfanone; Compound No. 185 ((5-(Ethylthio)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-sulfanone; Compound No. 186 Ethyl((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)(methyl)-16-sulfanone; Compound No. 187 5-(3-(Ethylthio)-6-methylpyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; Compound No. 188 5-(6-Cyclopropyl-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; Compound No. 189 5-(5-Cyclopropyl-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 190> 5-(3-(Ethylthio)-5-(4-fluorophenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 191> 5-(3-(Ethylthio)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 192> Ethyl (5-(4-fluorophenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(imino)-l6-sulfanone; <Compound No. 193> Ethyl (imino)(5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanone; <Compound No. 194> (6-Chloro-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(ethyl)(imino)-l6-sulfanone; <Compound No. 195> 5-(3-(Ethylsulfonyl)-6-(methylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 196> 5-(3-(Ethylsulfonyl)-6-(methylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 197> 5-(3-(Ethylthio)-5-vinylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 198> (5-((Dimethyl(oxo)-l6-sulfanilidene)amino)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(ethyl)(imino)-l6-sulfanone; <Compound No. 199> N-(Ethyl(oxo)(5-(4-(trifluoromethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanilidene)cyanamide; <Compound No. 200> (5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)(imino)(methyl)-l6-sulfanon; <Compound No. 201> 5-(3-(Ethylsulfonyl)-5-(2-methylprop-1-en-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 202> Ethyl(imino)(5-(2-methylprop-1-en-1-yl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanon; <Compound No. 203> Ethyl(imino)(5-(3-(trifluoromethyl)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanon; <Compound No. 204> 5-(3-(Ethylsulfonyl)-5-(prop-1-en-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 205> 5-(5-(2-Cyclopropylvinyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 206> N-((5-((Dimethyl(oxo)-l6-sulfanilidene)amino)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(ethyl)(oxo)-l6-sulfanilidene)cyanamide; <Compound No. 207> N-(Ethyl(oxo)(5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanilidene)cyanamide; <Compound No. 208> N-(Ethyl(5-(4-fluorophenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(oxo)-l6-sulfanilidene)cyanamide; <Compound No. 209> 5-(6-Ethyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 210> 5-(3-(Ethylsulfonyl)-6-(2-methylprop-1-en-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 211> 5-(5-Ethyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 212> 5-(3-(Ethylsulfonyl)-5-vinylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 213> 5-(5-Cyclobutyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 214> tert-Butyl 2-cyano-2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetate; <Compound No. 215> 5-(3-(Ethylsulfonyl)-6-(prop-1-en-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 216> (E)-5-(6-(2-Cyclopropylvinyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 217> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetonitrile; <Compound No. 218> 5-(Ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine; <Compound No. 219> 2-(5-(Ethylthio)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)acetonitrile; <Compound No. 220> 2-((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)oxy)-2-methylpropanamide; <Compound No. 221> 5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-ol; <Compound No. 222> tert-Butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)carbamate; <Compound No. 223> 5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine; <Compound No. 224> tert-Butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(methyl)carbamate; <Compound No. 225> N-(tert-Butyl)-2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetamide; <Compound No. 226> 5-(3-(Ethylsulfonyl)-6-methoxypyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 227> 5-(6-Ethoxy-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 228> 5-(6-Cyclobutyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 229> 5-(5-(Difluoromethoxy))-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 230> 5-(Ethylsulfonyl)-N,N-dimethyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine; <Compound No. 231> 5-(3-(Ethylsulfonyl)-5-(pyrimidin-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 232> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)acetonitrile; <Compound No. 233> N-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)cyclopropanecarboxamide; <Compound No. 234> 1-((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)hexahydro-1l6-thiopyran 1-oxide; <Compound No. 235> 1-((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)-1l6-thietane 1-oxide; <Compound No. 236> 5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-ol; <Compound No. 237> 5-(3-(Ethylsulfonyl)-6-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 238> 5-(3-(Ethylsulfonyl)-6-isopropylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 239> 5-(3-(Ethylsulfonyl)-6-(2,2,2-trifluoroethoxy)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 240> 5-(3-(Ethylsulfonyl)-6-isopropoxypyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 241> 5-(Ethylsulfonyl)-N-isopropyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 242> N-(Cyclopropylmethyl)-5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 243> 5-(3-(Ethylsulfonyl)-6-(thietan-3-yloxy)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 244> 5-(Ethylsulfonyl)-N-propyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 245> 1-((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)-1l6-thietane 1-oxide; <Compound No. ___> N-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)cyclopropanecarboxamide; <Compound Number___> 1-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)cyclopropane-1-carbonitrile; <Compound Number___> N-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-N-methylacetamide; <Compound Number___> 1-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)urea; <Compound Number___> 1-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-1,3-dimethylurea; <Compound Number___> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-2-methylpropanenitrile; <Compound Number___> 5-(3-(Ethylsulfonyl)-5-(trifluoromethyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number___> 5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)picolylamide; <Compound Number___> 5-(Ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)picolylamide; <Compound Number___> Methyl 5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinate; <Compound Number___> 5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinic acid azetidin-1-yl; <Compound Number___> (5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)methanone; <Compound Number___> (5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(morpholino)methanone; <Compound Number___> N-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)cyclopropanesulfonamide; <Compound Number___> N-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-N-methylcyclopropanesulfonamide; <Compound Number___> N-((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)(methyl)(oxo)-l6-sulfanilidene)cyanamide; <Compound Number___> Ethyl(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)((trifluoromethyl)imino)-l6-sulfanon; <Compound Number___> 2-((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)oxy)-2-methylpropanenitrile; <Compound Number___> 5-(3-(Ethylsulfonyl)-5-(pyridin-2-yloxy)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number___> 5-(5-(2,2-Difluorocyclopropyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound Number___> tert-Butyl 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)hydrazine-1-carboxylate; <Compound Number___> 1-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)ethan-1-one; <Compound Number___> N-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-O-methylhydroxylamine and <Compound Number___> 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-1,1,1-trifluoropropan-2-ol.

[0157] The compounds of the present invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers, and geometric isomers. Those skilled in the art will understand that one stereoisomer may be more active and / or exhibit beneficial effects when enriched or separated from other stereoisomers. Furthermore, those skilled in the art know methods for separating, enriching, and / or selectively preparing the above stereoisomers. The compounds of the present invention can exist as a mixture of stereoisomers, as individual stereoisomers, or in optically active forms.

[0158] When the compound of formula (I) is cationic or can form a cation, the anionic part of the salt can be inorganic or organic. Alternatively, when the compound of formula (I) is anionic or can form an anion, the cationic part of the salt can be inorganic or organic. Examples of the inorganic anionic part of the salt include, but are not limited to, chloride, bromide, iodide, fluoride, sulfate, phosphate, nitrate, nitrite, bicarbonate, and bisulfate. Examples of the organic anionic part of the salt include, but are not limited to, formate, alkanoate, carbonate, acetate, trifluoroacetate, trichloroacetate, propionate, glycolate, thiocyanate, lactate, succinate, malate, citrate, benzoate, cinnamate, oxalate, alkyl sulfate, alkyl sulfonate, aryl disulfonate, alkyl phosphate, aryl phosphate, aryl diphosphate, p-toluenesulfonate, and salicylate. Examples of the inorganic cationic part of the salt include, but are not limited to, alkali metals and alkaline earth metals. Examples of the organic cationic part of the salt include, but are not limited to, pyridine, methylamine, imidazole, benzimidazole, histidine, phosphazene, tetramethylammonium, tetrabutylammonium, choline, and trimethylamine.

[0159] The metal ions in the metal complex of the compound of formula (I) are, in particular, ions of elements of Group 2, especially calcium and magnesium ions, ions of elements of Groups 3 and 4, especially aluminum, tin, and lead ions, and also ions of elements of Transition Groups 1 to 8, especially chromium, manganese, iron, cobalt, nickel, copper, zinc, etc. Metal ions of elements of the fourth period and Transition Groups 1 to 8 are particularly preferred. Here, the metal can exist in various valences that the metal can assume.

[0160] In one embodiment, the present invention provides a compound of formula (I), its agriculturally acceptable salts, metal complexes, structural isomers, stereoisomers, diastereoisomers, enantiomers, chiral isomers, atropisomers, conformational isomers, rotational isomers, tautomers, optical isomers, polymorphs, geometric isomers, or N-oxides, and their compositions comprising excipients, inert carriers, or surfactants, additives, solid diluents, liquid diluents, and other essential components.

[0161] The compounds of formula (I) (including all stereoisomers, N-oxides, and salts thereof) typically exist in two or more forms, and thus, formula (I) includes all crystalline and amorphous forms of the compounds represented by formula (I). Amorphous forms include embodiments that are solids such as waxes and gums, as well as embodiments that are liquids such as solutions and melts. Crystalline forms include embodiments that essentially represent a single crystal form, and embodiments that represent a mixture of polymorphs (i.e., different crystal forms). The term "polymorph" refers to specific crystal forms of a compound that can crystallize in different crystal forms, and these forms have different arrangements and / or conformations of molecules in the crystal lattice. Polymorphs can have the same chemical composition, but can also differ in composition due to the presence or absence of co-crystallized water or other molecules that can bind weakly or strongly in the lattice. Polymorphs can differ in chemical, physical, and biological properties such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate, and bioavailability. Those skilled in the art will understand that a polymorph of a compound represented by formula (I) can exhibit beneficial effects (e.g., suitability for the preparation of useful formulations, improved biological performance) compared to another polymorph or a mixture of polymorphs of the same compound represented by formula (I). The preparation and isolation of a specific polymorph of a compound represented by formula (I) can be achieved by methods known to those skilled in the art, including crystallization using a selected solvent and temperature.

[0162] In one embodiment, the present invention provides a process for preparing a compound of formula (I) or an agriculturally acceptable salt thereof.

[0163] The compounds of the present invention defined by formula (I) and / or Table (I) can be prepared by known methods in various ways as described in Schemes 1-2. The compounds of the present invention can be produced as shown in the following schemes, where, unless otherwise specified, the definitions of each variable are as defined above for the compounds of formula (I).

[0164] According to the features of the present invention, compounds of general formula (I) in which all symbols are as defined above can be prepared by the methods shown in Scheme-1, Scheme-2 or the Examples. Representative procedures are shown below; however, the present disclosure should not be construed as limiting the scope of the present invention to reach the compounds of formula (1) described below.

[0165]

Chemical formula

[0166] According to Scheme-1, the present invention provides a method for preparing a compound of formula (I) starting from a suitable halide or triflate of formula (2), where Q is as defined above.

[0167] The compound of general formula (I) can be obtained from the compound of formula (2) under standard Suzuki cross-coupling conditions with a boronic acid or a boronic acid ester compound of formula (3). The Suzuki cross-coupling reaction can be catalyzed by a palladium-based catalyst (Catalyst) including but not limited to 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium(II) or tetrakis(triphenylphosphine)palladium(0). For example, it can be dissolved and used in a suitable solvent system (Solvent) such as tetrahydrofuran (THF), N,N'-dimethylformamide (DMF), 1,2-dimethoxyethane, 1,4-dioxane, or a mixed solvent such as THF / water, 1,2-dimethoxyethane / water, 1,4-dioxane / water. The reaction is usually carried out in the presence of a base (Base), for example, potassium carbonate, cesium carbonate, potassium phosphate. The reaction temperature is preferably in the range from room temperature (80 °C) to the boiling point of the reaction mixture, or at a temperature of 70 °C to 150 °C under microwave irradiation, and the compound of formula (I) cited in the literature can be produced. For example, it is described in Chem. Soc. Rev. 2014, 43, 412 - 443 or WO2014070978.

[0168] Alternatively, the compound of formula (I) may be coupled with a heteroaryl tin compound of formula (3) in the presence of a catalyst such as bis(triphenylphosphine)palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), 1,1'-bis(diphenylphosphino)ferrocene palladium(II) chloride, tris(dibenzylideneacetone)dipalladium(0), palladium(II) acetate, etc. Nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride, and copper catalysts such as copper(I) iodide and copper(I) chloride can be reacted in a suitable solvent such as acetonitrile or tetrahydrofuran (THF) in the presence of a base such as an alkali metal hydride, an alkali metal carbonate, or an organic base. The reaction can be carried out in a suitable solvent such as N,N'-dimethylformamide (DMF), 1,2-dimethoxyethane, or 1,4-dioxane at a temperature from room temperature to the reflux temperature of the solvent, or under microwave irradiation at a temperature from 70 °C to 150 °C. For this reaction, a ligand and / or an inorganic halogen compound can be added as necessary. Examples of ligands used in the reaction include triphenylphosphine, xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-(dicyclohexylphosphino)-2',4',6'-triisopropyl-1,1'-biphenyl, 2-aminoethanol, 8-hydroxyquinoline, and 1,10-phenanthroline. Examples of inorganic halogen compounds include alkali metal fluorides such as potassium fluoride and sodium fluoride; and alkali metal halides such as lithium chloride, sodium chloride, and sodium chloride.

[0169] [Chemical formula]

[0170] Scheme-2 depicts the production of stannane of general formula (3) by reacting an appropriate halide or triflate of the compound of formula (4) with a reagent such as hexamethylditin or triethyltin chloride in the presence of a catalyst such as tetrakis(triphenylphosphine)palladium(0). It is carried out under microwave irradiation at a temperature between 25 °C and the reflux temperature of the solvent, or between 70 °C and 160 °C, in the presence of a base such as potassium carbonate, in a suitable solvent such as N,N'-dimethylformamide (DMF) or a mixture of two or more suitable solvents (Solvent).

[0171] Alternatively, the compound of general formula (3) can be obtained by reacting the compound of general formula (4) with a reagent such as n-butyllithium in a suitable aprotic solvent such as tetrahydrofuran (THF) at a temperature between -100 °C and 25 °C, and then reacting with a reagent such as hexamethylditin or triethyltin chloride in a suitable aprotic solvent such as tetrahydrofuran (THF) at a temperature between -100 °C and 50 °C.

[0172] In one embodiment, the present invention provides a composition for controlling or preventing invertebrate pests. This composition consists of a biologically effective amount of an agriculturally acceptable salt, isomer / structural isomer, stereoisomer, diastereomer, enantiomer, tautomer, metal complex, polymorph, or N-oxide thereof of the compound of formula (I), and at least one additional component selected from the group consisting of surfactants and adjuvants.

[0173] 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.

[0174] In yet another embodiment, the present invention provides a compound of formula (I) or an N-oxide and a salt thereof in conventional types of pesticidal compositions, such as solutions, emulsions, suspensions, powders, dusts, pastes, granules, pressings, capsules, and mixtures thereof. Examples of types of compositions include suspensions (such as SC, OD, FS, etc.), emulsifiable concentrates (such as EC, etc.), emulsions (such as EW, EO, ES, ME, etc.), capsules (such as CS, ZC, etc.), pastes, troches, wettable powders, powders (such as WP, SP, WS, DP, DS), pressings (such as BR, TB, DT), granules (such as WG, SG, GR, FG, GG, MG), insecticides (such as LN), and gel formulations (such as GF) for the treatment of plant propagation materials such as seeds. These and other types of compositions are defined in the ''Catalogue of pesticide formulation types and international coding system'', Technical Monograph No.2, 6 th Ed. May 2008, CropLife International.

[0175] The compositions are prepared by known methods as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, TandF Informa, London, 2005.

[0176] Examples of suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration promoters, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreezing agents, antifoaming agents, colorants, tackifiers, or binders.

[0177] Suitable solvents and liquid carriers are water and organic solvents, such as middle-boiling to high-boiling mineral oil fractions, such as kerosene, diesel oil; oils derived from plants or animals; aliphatic hydrocarbons, cyclic hydrocarbons, and aromatic hydrocarbons, such as toluene, paraffin, tetrahydronaphthalene, alkylated naphthalene; alcohols, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, such as cyclohexanone; esters, such as lactate esters, carbonate esters, fatty acid esters, γ-butyrolactone; fatty acids; phosphonates; amines; amides, such as N-methylpyrrolidone, fatty acid dimethylamide; and mixtures thereof.

[0178] Suitable solid carriers or fillers are mineral earths, such as silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, such as cellulose, starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; vegetable-derived products, such as cereal flour, bark flour, wood flour, nut shell flour, and mixtures thereof.

[0179] Suitable surfactants are surfactant compounds, such as anionic, cationic, nonionic, and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration promoters, protective colloids, or adjuvants. Examples of surfactants are listed in McCutcheon’s, Vol.1: Emulsifiers and Detergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (international or North American edition).

[0180] Suitable anionic surfactants are alkali salts, alkaline earth salts, or ammonium salts of sulfonic acids, sulfuric acids, phosphoric acids, and carboxylic acids, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl and tridecyl benzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates, or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, sulfates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols, or sulfates of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.

[0181] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine 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, which are 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 sorbitan, ethoxylated sorbitan, sucrose and glucose esters, or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinyl pyrrolidone, vinyl alcohol, or vinyl acetate.

[0182] Suitable cationic surfactants are quaternary surfactants, for example, quaternary ammonium compounds having one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are A-B type or A-B-A type block polymers containing blocks of polyethylene oxide and polypropylene oxide, or A-B-C type block polymers containing alkanol, polyethylene oxide, and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamine or polyethyleneamine.

[0183] Suitable adjuvants are compounds that have negligible pesticidal activity by themselves or even no pesticidal activity and that improve the biological performance of Compound I against the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed in Knowles, Adjuvants and additives, Agrow Reports DS256, TandF Informa UK, 2006, chapter 5.

[0184] Suitable thickeners are polysaccharides (e.g., xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates. Suitable bactericides are bronopol and isothiazolinone derivatives such as alkyl isothiazolinone and benzisothiazolinone. Suitable antifreezing agents are ethylene glycol, propylene glycol, urea, and glycerin. Suitable defoamers are silicones, long-chain alcohols, and salts of fatty acids. Suitable colorants (e.g., red, blue, or green) are pigments with low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g., iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (e.g., alizarin, azo, and phthalocyanine colorants). Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylate, biological or synthetic waxes, and cellulose ethers.

[0185] Examples of the types of compositions and their preparation are as follows:

[0186] i) Water-soluble concentrates (SL, LS)

[0187] 10 - 60% by weight of Compound I or its N-oxide or salt and 5 - 15% by weight of a wetting agent (e.g., alcohol alkoxylate) are dissolved in water and / or a water-soluble solvent (e.g., alcohol) up to 100% by weight. The active substance dissolves when diluted with water.

[0188] ii) Dispersible concentrates (DC)

[0189] 5 - 25% by weight of Compound I or its N-oxide or salt and 1 - 10% by weight of a dispersant (e.g., polyvinylpyrrolidone) are dissolved in an organic solvent (e.g., cyclohexanone) up to 100% by weight. A dispersion is obtained by dilution with water.

[0190] iii) Emulsifiable concentrates (EC)

[0191] 15 to 70% by weight of Compound I or its N-oxide or salt and 5 to 10% by weight of an emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (e.g., aromatic hydrocarbon) at up to 100% by weight. By diluting with water, an emulsion is obtained.

[0192] iv) Emulsion (EW, EO, ES)

[0193] 5 to 40% by weight of Compound I or its N-oxide or salt and 1 to 10% by weight of an emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20 to 40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon). This mixture is introduced into water by an emulsifying device at up to 100% by weight to form a uniform emulsion. By diluting with water, an emulsion is obtained.

[0194] v) Suspension (SC, OD, FS)

[0195] In a stirred ball mill, 20 to 60% by weight of Compound I or its N-oxide or salt is ground by the addition of 2 to 10% by weight of a dispersant and wetting agent (e.g., sodium lignosulfonate and alcohol ethoxylate), 0.1 to 2% by weight of a thickener (such as xanthan gum), and up to 100% by weight of water to produce a fine active substance suspension. By diluting with water, a stable suspension of the active substance is obtained. For FS-type compositions, up to 40% by weight of a binder (e.g., polyvinyl alcohol) is added.

[0196] vi) Water-dispersible granules and water-soluble granules (WG, SG)

[0197] 50 to 80% by weight of Compound I or its N-oxide or salt is finely ground by the addition of up to 100% by weight of a dispersant and wetting agent (e.g., sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by technical equipment (e.g., extrusion, spray tower, fluidized bed). By diluting with water, a stable dispersion or solution of the active substance is obtained.

[0198] vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

[0199] 50 to 80% by weight of Compound I or its N-oxide or salt, 1 to 5% by weight of a dispersant (e.g., sodium lignosulfonate), 1 to 3% by weight of a wetting agent (e.g., alcohol ethoxylate), and up to 100% by weight of a solid carrier, such as silica gel, are added and ground in a rotor-stator mill. By diluting with water, a stable dispersion or solution of the active substance is obtained.

[0200] viii) Gels (GW, GF)

[0201] In a stirred ball mill, 5 to 25% by weight of Compound I or its N-oxide or salt, 3 to 10% by weight of a dispersant (e.g., sodium lignosulfonate), 1 to 5% by weight of a thickening agent (e.g., carboxymethyl cellulose), and up to 100% by weight of water are added and ground to obtain a fine suspension of the active substance. By diluting with water, a stable suspension of the active substance is obtained.

[0202] ix) Microemulsions (ME)

[0203] 5 to 20% by weight of Compound I or its N-oxide or salt are added to 5 to 30% by weight of an organic solvent blend (e.g., fatty acid dimethylamide and cyclohexanone), 10 to 25% by weight of a surfactant blend (e.g., alcohol ethoxylate and arylphenol ethoxylate), and up to 100% of water. This mixture is stirred for 1 hour to spontaneously form a thermodynamically stable microemulsion.

[0204] x) Microcapsules (CS)

[0205] Disperse an oil phase containing 5 to 50% by weight of Compound I or its N-oxide or salt, 0 to 40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and 2 to 15% by weight of an acrylic monomer (e.g., methyl methacrylate, methacrylic acid, and diol triacrylate) in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Poly(methyl acrylate) microcapsules are formed by radical polymerization initiated by a radical initiator. Alternatively, disperse an oil phase containing 5 to 50% by weight of Compound I according to the present invention, 0 to 40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and an isocyanate monomer (e.g., diphenylmethane-4,4'-diisocyanate) in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Polyurea microcapsules are formed by the addition of a polyamine (e.g., hexamethylenediamine). The amount of the monomer is 1 to 10% by weight. The % by weight is based on the total of the CS composition.

[0206] xi) Dustable powder (DP, DS)

[0207] Finely pulverize 1 to 10% by weight of Compound I or its N-oxide or salt and mix it intimately with up to 100% by weight of a solid carrier, e.g., micronized kaolin.

[0208] xii) Granule (GR, FG)

[0209] Finely pulverize 0.5 to 30% by weight of Compound I or its N-oxide or salt and associate it with up to 100% by weight of a solid carrier (e.g., silicate). Granule formation is carried out by extrusion, spray drying, or fluidized bed.

[0210] xiii) Very small amount of liquid (UL)

[0211] Dissolve 1 to 50% by weight of Compound I or its N-oxide or salt in up to 100% by weight of an organic solvent, e.g., aromatic hydrocarbon.

[0212] The types of the compositions of i) to xiii) may optionally further contain auxiliaries, for example, 0.1 to 1% by weight of a bactericide, 5 to 15% by weight of an antifreeze, 0.1 to 1% by weight of an antifoaming agent, and 0.1 to 1% by weight of a colorant, etc.

[0213] In another embodiment, the present invention provides a pesticidal composition compound of formula (I), which contains 0.01 to 95% by weight, preferably 0.1 to 90%, more preferably 1 to 70%, particularly 10 to 60% by weight of an active substance. The active substance is used at a purity of 90% to 100%, preferably 95% to 100% (by NMR spectrum).

[0214] Water-soluble concentrates (LS), suspoemulsions (SE), flowable concentrates (FS), dry treatment powders (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are usually used for the purpose of treating plant propagation materials, particularly seeds. The composition in question provides an active substance concentration of 0.01 to 60% by weight, preferably 0.1 to 40% by weight, in a preparation that can be used immediately after being diluted 2 to 10 times. Application can be carried out before sowing or during sowing.

[0215] Methods for applying or treating Compound I and their compositions to plant propagation materials, particularly seeds, respectively, include methods of dressing, coating, pelletizing, dusting, soaking, and in-furrow application of the propagation materials. Preferably, Compound I or their compositions are respectively applied to plant propagation materials by methods such that germination is not induced, for example, seed dressing, pelletizing, coating, and dusting.

[0216] When used for plant protection, the amount of the active substance applied is 0.001 to 2 kg per hectare, preferably 0.005 to 2 kg per hectare, more preferably 0.05 to 0.9 kg per hectare, particularly 0.1 to 0.75 kg per hectare, depending on the type of desired effect.

[0217] In the treatment of plant propagation materials such as seeds, for example, by dusting, coating, or waterlogging seeds, an amount of active substance of 0.1 to 1000 g, preferably 1 to 500 g, more preferably 1 to 100 g, and most preferably 5 to 100 g per 100 kilograms of plant propagation material (preferably seeds) is generally required.

[0218] When used for the protection of materials or storage products, the amount of active substance applied varies depending on the type of application area and the desired effect. The amount usually applied for the protection of materials is 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active substance per cubic meter of treated material.

[0219] Various types of oils, wetting agents, adjuvants, fertilizers, or micronutrients, and other control agents (e.g., herbicides, insecticides, fungicides, growth regulators, safeners) can be added as a premix to the active substance or the composition containing the active substance, or added (tank mix) just before use if appropriate. These agents can be mixed with the composition according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0220] The user can usually apply the composition according to the invention from a pre - dosing device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is composed of water, buffer solution, and / or further auxiliaries to the desired application concentration, and thus a spray liquid or agrochemical composition according to the invention in a ready - to - use state is obtained. Usually, 20 to 6000 liters, preferably 35 to 1000 liters, and more preferably 50 to 500 liters of ready - to - use spray liquid per hectare of agricultural useful area are applied.

[0221] According to one embodiment, the individual components of the composition according to the invention, such as part of a kit or part of a binary or ternary mixture, may be mixed by the user himself in the spray tank, and further auxiliaries may be added if necessary.

[0222] Thus, the compounds and compositions of the present invention are agriculturally useful for protecting field crops from phytophagous invertebrate pests and are also non-agriculturally useful for protecting other horticultural crops and plants from phytophagous invertebrate pests. This usefulness includes the protection of crops and other plants (i.e., both agricultural and non-agricultural) that contain genetically engineered (i.e., transgenic) or mutagenized genetic material to provide advantageous traits.

[0223] The compounds of the present invention are characterized by favorable metabolic and / or soil residue patterns and exhibit activity against a range of agricultural and non-agricultural invertebrate pests. The compounds of the present invention are active ingredients that are prophylactically and / or therapeutically valuable in the field of pest control even at low application rates, and the active ingredients can be used against control agent-resistant pests such as insects and mites and are well tolerated by warm-blooded species, fish, and plants.

[0224] In the context of the present invention, "control of invertebrate pests" means inhibition of the occurrence (including lethality) of invertebrate pests that causes a significant reduction in food or other injury or damage caused by the pests. (Related expressions are defined similarly.) As referred to in the present invention, the term "invertebrate pest" includes arthropods, gastropods, and nematodes that are economically important as pests. The term "arthropod" includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs, and earwigs.

[0225] The term "gastropod" includes snails, slugs, and other stylommatophorans. The term "helminth" includes all helminths such as roundworms, dog heartworms, phytophagous nematodes (Class Nematoda), flukes (Class Tematoda), hookworms, tapeworms (Class Cestoda), etc. Those skilled in the art will recognize that not all compounds will be equally effective against all pests.

[0226] The compounds of the present invention are active against economically important agricultural pests in forests, greenhouses, seedlings, ornamental plants, turf, food and fiber, public and animal health, household and commercial structures, and household and stored products pests. These include lepidopteran larvae such as armyworm larvae, cutworms, weevils, and heliothines.

[0227] (e.g., fall armyworm (Spodoptera fugiperda J. E. Smith), beet armyworm (Spodoptera exigua Hubner), black cutworm (Agrotis ipsilon Hufnagel), cabbage looper (Trichoplusia ni Hubner), tobacco budworm (Heliothis virescens Fabricius));

[0228] Pyralid borers, casebearers, webworms, and coneworms, leaf beetles, and skeletonizers (e.g., European corn borer (Ostrinia nubilalis Hubner), navel orangeworm (Amyelois transitella Walker), corn root webworm (Crambus caliginosellus Clemens), and sod webworm (Herpetogramma licarsisalis Walker));

[0229] Leafrollers, green worms, and seed worms, and fruit worms (e.g., codling moth (Cydia pomonella Linnaeus), grape berry moth (Endopiza viteana Clemens), oriental fruit moth (Grapholita molesta Busck)) of the Tortricidae family;

[0230] And many other economically important Lepidoptera (e.g., diamondback moth (Plutella xylostella Linnaeus), pink bollworm (Pectinophora gossypiella Saunders), gypsy moth (Lymantria dispar Linnaeus));

[0231] Nymphs and adults of the order Blattodea, including cockroaches of the Ectobiidae and Blattidae families (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 brunnea Burmeister), Madeira cockroach (Leucophaea maderae Fabricius));

[0232] Coleopteran leaf-feeding larvae and adults, including weevils of the families Curculionidae, Bruchidae, and Chrysomelidae (e.g., boll weevil (Anthonomus grandis Boheman), rice water weevil (Lissorhoptrus oryzophilus Kuschel), granary weevil (Sitophilus granarius Linnaeus), rice weevil (Sitophilus oryzae Linnaeus));

[0233] Fleas of the family Pulicidae, cucumber beetles, rootworms, fleas, potato beetles, and leaf miners (e.g., Colorado potato beetle (Leptinotarsa decemlineata Say), western corn rootworm (Diabrotica virgifera virgifera LeConte));

[0234] Japanese beetles and other beetles of the family Scarabaeidae (e.g., Japanese beetle (Popillia japonica Newman) and European chafer (Rhizotrogus majalis Razoumowsky));

[0235] Carpet beetles of the family Dermestidae;

[0236] Wireworm larvae of the family Elateridae;

[0237] Bark beetles of the family Scolytidae, and flour beetles of the family Tenebrionidae. Further, this 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));

[0238] Hemipteran adults and nymphs, such as, for example, the plant bug of the family Miridae, the cicada of the family Cicadidae, the leafhopper (e.g., Empoasca spp.) of the family Cicadellidae, the planthopper of the families Fulgoroidae and Delphacidae, the treehopper of the family Membracidae, the psyllid of the family Psyllidae, the whitefly of the family Aleyrodidae, the aphid of the family Aphididae, the phylloxera of the family Phylloxeridae, the mealybug of the family Pseudococcidae, the scale of the families Coccidae, Diaspididae, and Margarodidae, and the lace bug of the family Tingidae, the stink bug of the family Pentatomidae, the cinch bug (e.g., Blissus spp.) of the family Lygaeidae, and other seed bugs, the spittlebug of the family Cercopidae, the squash bug of the family Coreidae, and the red bug of the family Pyrrhocoridae, and the cotton stainer are included.Adult and larval arachnids, such as spider mites and red mites of the family Tetranychidae (e.g., European red mite (Panonychus ulmi Koch), two spotted spider mite (Tetranychus urticae Koch), McDaniel mite (Tetranychus mcdanieli McGregor)), flat mites of the family Tenuipalpidae (e.g., citrus flat mite (Brevipalpus lewisi McGregor)), and rust mites and bud mites of the family Eriophyidae, as well as other leaf-feeding mites and mites important to human and animal health, namely, dust mites of the family Epidermoptidae, follicle mites of the family Demodicidae, grain mites of the family Glycyphagidae, ticks of the family Ixodidae (e.g., deer tick (Ixodes scapularis Say), Australian paralysis tick (Ixodes holocyclus Neumann), American dog tick (Dermacentor variabilis Say), lone star tick (Amblyomma americanum Linnaeus), and scab mites and itch mites of the families Psoroptidae, Pyemotidae, and Sarcoptidae;。

[0239] Adult and larval Orthoptera including grasshoppers, locusts, and crickets (e.g., migratory grasshoppers (e.g., Melanoplus sanguinipes Fabricius, M. differentialis Thomas), American grasshopper (e.g., Schistocerca americana Drury), desert locust (Schistocerca gregaria Forskal), migratory locust (Locusta migratoria Linnaeus), house cricket (Acheta domesticus Linnaeus), mole cricket (Gryllotalpa spp.));

[0240] Adult and larval Diptera, including leafminers, midges, fruit flies (Tephritidae), frit flies (e.g., Oscinella frit Linnaeus), soil maggots, house flies (e.g., Musca domestica Linnaeus), lesser house flies (e.g., Fannia canicularis Linnaeus, F. femoralis Stein), stable flies (e.g., Stomoxys calcitrans Linnaeus), face flies, horn flies, blow flies (e.g., Chiysomya spp., Phonnia spp.), and other muscoid fly pests, horse flies (e.g., Tabanus spp.), botflies (e.g., Gastrophilus spp., Oestrus spp.), cattle grubs (e.g., Hypoderma spp.), deer flies (e.g., Chrysops spp.), keds (e.g., Melophagus ovinus Linnaeus), and other Brachycera, mosquitoes (e.g., Aedes spp., Anopheles spp., Culex spp.), black flies (e.g., Prosimulium spp., Simulium spp.), biting midges, sand flies, sciarids, and other Nematocera;

[0241] Adult and larval Thysanoptera, including onion thrips (Thrips tabaci Lindeman), and other leaf-feeding thrips;

[0242] Ants (e.g., red carpenter ant (Camponotus ferrugineus Fabricius), black carpenter ant (Camponotus pennsylvanicus De Geer), Pharaoh ant (Monomorium pharaonis Linnaeus), little fire ant (Wasmannia auropunctata Roger), fire ant (Solenopsis geminata Fabricius), red imported fire ant (Solenopsis invicta Buren), Argentine ant (Iridomyrmex humilis Mayr), crazy ant (Paratrechina longicornis Latreille), pavement ant (Tetramorium caespitum Linnaeus), cornfield ant (Lasius alienus Förster), odorous house ant (Tapinoma sessile Say)), bees (including carpenter bee), hornets, yellow jackets, and wasps, including hymenopteran insect pests;

[0243] Isopteran insect pests, including 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 economically important termites;

[0244] Insect pests of the order Thysanura, including, for example, silverfish (Lepisma saccharina Linnaeus) and firebrat (Thermobia domestica Packard);

[0245] Insect pests of the order Phthiraptera, including head louse (Pediculus humanus capitis De Geer), body louse (Pediculus humanus humanus Linnaeus), chicken body louse (Menacanthus stramineus Nitszch), dog biting louse (Trichodectes cams De Geer), fluff louse (Goniocotes gallinae De Geer), sheep body louse (Bovicola ovis Schrank), short-nosed cattle louse (Haematopinus eurystemus Nitzsch), long-nosed cattle louse (Linognathus vituli Linnaeus), and other sucking and piercing parasitic lice that attack humans and animals;

[0246] Insect pests of the order Siphonoptera, including the oriental rat flea (Xenopsylla cheopis Rothschild), the cat flea (Ctenocephalides felis Bouche), the dog flea (Ctenocephatides canis Curtis), the hen flea (Ceratophyllus gallinae Schrank), the sticktight flea (Echidnophaga gallinacea Westwood), the human flea (Pulex irritans Linnaeus), and other fleas that attack mammals and birds. Also included are additional arthropod pests, such as spiders of the order Araneae, for example, the brown recluse spider (Loxosceles reclusa Gertsch and Mulaik), and the black widow spider (Latrodectus mactans Fabricius), and centipedes of the order Scutigeromorpha, for example, the house centipede (Scutigera coleoptrata Linnaeus).The activity includes members of the classes Nematoda, Cestoda, Trematoda, and Acanthocephala, including economically important members of the orders Rhabditida, Strongylida, Oxyurida, Spirurida, and Enoplida, for example, but not limited to, economically important agricultural pests (i.e., Meloidogyne spp. such as Meloidogyne incognita (root knot nematode), Pratylenchus spp. such as Pratylenchus neglectus (lesion nematode), Trichodorus spp. such as Trichodorus primitivus (stubby root nematode), etc.), as well as animal and human health pests (i.e., all economically important flukes, tapeworms, and roundworms, for example, Strongylus vulgaris in horses, Toxocara canis in dogs, Haemonchus contortus in sheep, Dirofilaria immitis Leidy in dogs, Anoplocephala perfoliata in horses, Fasciola hepatica Linnaeus in ruminants, etc.).

[0247] The compounds of the present invention are useful against Lepidopteran pests (e.g., Alabama argillacea Hubner (cotton leaf worm), Archips argyrospila Walker (fruit tree leaf roller), A. rosana Linnaeus (European leaf roller), and other Archips spp., Chilo suppressalis Walker (rice stem borer), Cnaphalocrosis medinalis Guenee (rice leaf roller), Crambus caliginosellus Clemens (corn root webworm), Crambus teterrellus Zincken (bluegrass webworm), Cydia pomonella Linnaeus (codling moth), Earias insulana Boisduval (spiny bollworm), Earias vittella Fabricius (spotted bollworm), Helicoveipa armigera Hubner (American bollworm), Helicoverpa zea Boddie (corn earworm), Heliothis virescens Fabricius (tobacco budworm), Herpetogramma licarsisalis Walker (sod webworm), Lobesia botrana Denis and Schiffeπnuller (grape berry moth), Pectinophora gossypiella Saunders (pink bollworm), Phyllocnistis citrella Stainton (citrus leafminerIt shows particularly high activity against, for example, Liriomyza trifolii (Burgess) (leafminer), Pieris brassicae Linnaeus (large white butterfly), Pieris rapae Linnaeus (small white butterfly), Plutella xylostella Linnaeus (diamondback moth), Spodoptera exigua Hubner (beet armyworm), Spodoptera litura Fabricius (tobacco cutworm, cluster caterpillar), Spodoptera frugiperda J. E. Smith (fall armyworm), Trichoplusia ni Hubner (cabbage looper), and Tuta absoluta Meyrick (tomato leafminer).

[0248] The compounds of the present invention also have commercially significant activity against members of the Homoptera including: Acyrthisiphon pisum Harris (pea aphid), Aphis craccivora Koch (cowpea aphid), Aphis fabae Scopoli (black bean aphid), Aphis gossypii Glover (cotton aphid, melon aphid), Aphis pomi De Geer (apple aphid), Aphis spiraecola Patch (spirea aphid), Aulacorthum solani Kaltenbach (foxglove aphid), Chaetosiphon fragaefolii Cockerell (strawberry aphid), Diuraphis noxia Kurdjumov / Mordvilko (Russian wheat aphid), Dysaphis plantaginea Paaserini (rosy apple aphid), Eriosoma lanigerum Hausmann (woolly apple aphid), Hyalopterus pruni Geoffroy (mealy plum aphid), Lipaphis erysimi Kaltenbach (tarnip aphid), Metopolophium dirrhodum Walker (cereal aphid), Macrosipum euphorbiae Thomas (pqtato aphid), Myzus persicae Sulzer (peach-potato aphid, green peach aphid), Nasonovia ribisnigriMosley (lettuce aphid), Pemphigus spp. (root aphid and gall aphid), Rhopalosiphum maidis Fitch (corn leaf aphid), Rhopalosiphum padi Linnaeus (bird cherry - oat aphid), Schizaphis graminum Rondani (greenbug), Sitobion avenae Fabricius (English grain aphid), Theriaphis maculata Buckton (spotted alfalfa aphid), Toxoptera aurantii, Boyer de Fonscolombe (black citrus aphid), and Toxoptera citricida Kirkaldy (brown citrus aphid); Adelges spp. (adelgid); Phylloxera devastatrix Pergande (pecan phylloxera); Bemisia tabaci Gennadius (tobacco whitefly, sweetpotato whitefly), Bemisia argentifolii Bellows and Perring (silverleaf whitefly), Dialeurodes citri Ashmead (citrus whitefly) and Trialeurodes vaporariorum Westwood (greenhouse whitefly); Empoasca fabae Harris, (potato leafhopper), Laodelphax striatellusFallen (smaller brown planthopper), Macrolestes quadrilineatus Forbes (aster leafhopper), Nephotettix cinticeps Uhler (green leafhopper), Nephotettix nigropictus Stal (rice leafhopper), Nilaparvata lugens Stal (brown planthopper), Peregrinus maidis Ashmead (corn planthopper), Sogatella furcifera Horvath (white-backed planthopper), Sogatodes orizicola Muir (rice delphacid), Typhlocyba pomaria McAfee white apple leafhopper, Erythroneoura spp. (grape leafhopper); Magicicada septendecim Linnaeus (periodical cicada); Icerya purchasi Maskell (cottony cushion scale), Quadraspidiotus perniciosus Comstock (San Jose scale); Planococcus citri Risso (citrus mealybug); Pseudococcus spp. (other mealybug complex); Cacopsylla pyricola Foerster (pear psylla), Trioza diospyri Ashmead (persimmon psylla).

[0249] These compounds are also active against members of the Hemiptera order, including: Acrostemum hilare Say (green stink bug), Anasa tristis De Geer (squash bug), Blissus leucopterus leucopterus Say (chinch bug), Corythuca gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), Dysdercus suturellus Herrich-Schaffer (cotton stainer), Euchistus servus Say (brown stink bug), Euchistus variolrius Palisot de Beauvois (one-spotted stink bug), Graptosthetus spp. (complex of seed bug), Leptoglossus corculus Say (leaf-footed pine seed bug), Lygus lineolaris Palisot de Beauvois (tarnished plant bug), Nezara viridula Linnaeus (southern green stink bug), Oebalus pugnax Fabricius (rice stink bug), Oncopeltus fasciatus DaEas (large milkweed bug), Pseudatomoscelis seriatus Reuter (cotton fleahopper).

[0250] Other insects controlled by the compounds of formula (I) of the present invention include the following: Thysanoptera (e.g., Frankliniella occidentalis Pergande (western flower thrip), Scirthothnps citri Moulton (citrus thrip), Sericothrips variabilis Beach (soybean thrip), and Thrips tabaci Lindeman (onion thrip)); and other Coleoptera (e.g., Leptinotarsa decemlineata Say (Colorado potato beetle), Epilachna varivestis Mulsant (Mexican bean beetle)) and wireworm larvae of the genus Agriotes, Athous, or Limonius).

[0251] In particular, the compounds of formula (I), their N-oxides, their isomers, their polymorphs, and their salts are particularly suitable for effectively controlling the following pests:

[0252] Lepidopteran insects (Lepidoptera), for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Chilo infuscatellus, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Earias vittella, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholita funebrana, Grapholita molesta, Helicoverpa armigera, Helicoverpa virescens, Helicoverpa zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Leucinodes orbonalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, OstriniaOstrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scirpophaga incertulas, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Spodoptera exigua, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis; and

[0253] Beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aphthona euphoridae, Athous haemorrhoidalis, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Ctenicera ssp., Diabrotica longicornis, Diabrotica semipunctata, Diabrotica undecimpunctata Diabrotica speciosa, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllobius pyri, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria;.

[0254] 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, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, Tipula oleracea, and Tipula paludosa;.

[0255] Termites (Isoptera), for example, Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes grassei, Termes natalensis, and Coptotermes formosanus;

[0256] Cockroaches (Dictyoptera), e.g., Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis;

[0257] Ants, bees, wasps, hornets (Hymenoptera), e.g., Athalia rosae, Atta cephalotes, Atta capiguara, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Lasius niger, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex californicus, Pheidole megacephala, Dasymutilla occidentalis, Bombus spp., Vespula squamosa, Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolichovespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile;

[0258] Crickets, grasshoppers, locusts (Orthoptera), for example, Acheta domestica, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Calliptamus italicus, Chortoicetes terminifera, and Locustana pardalina;

[0259] Widow spiders, for example, Latrodectus mactans, and Loxosceles reclusa;

[0260] Fleas (Order Siphonaptera), such as Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus, silverfish (Order Thysanura), such as Lepisma saccharina and Thermobia domestica, centipedes (Order Chilopoda), such as Scutigera coleoptrata, millipedes (Order Diplopoda), such as Narceus spp., earwigs (Order Dermaptera), such as Forficula auricularia, lice (Order Phthiraptera), such as Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon allinae, Menacanthus stramineus, and Solenopotes capillatus, springtails (Order Collembola), such as Onychiurus ssp.

[0261] The compounds of formula (I) of the present invention are effective against nematodes: plant parasitic nematodes, such as root knot nematodes, e.g., Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis, and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematode, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematode, and Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci, and other Ditylenchus species; Awl nematode, Dolichodorus species; Spiral nematode, Heliocotylenchus multicinctus, and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species, and Hemicriconemoides species; Hirshmanniella species; Lance nematode, Hoploaimus species; false rootknot nematode, Nacobbus species;It is also suitable for controlling needle nematodes, Longidorus elongatus, and other Longidorus species; lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi, and other Pratylenchus species; burrowing nematodes, Radopholus similis, and other Radopholus species; reniform nematodes, Rotylenchus robustus, and other Rotylenchus species; Scutellonema species; stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, and other Tylenchorhynchus species; citrus nematodes, Tylenchulus species; dagger nematodes, Xiphinema species; and other plant parasitic nematode species.

[0262] The compounds of formula (I) and salts thereof are useful for controlling arachnids (Arachnida), such as spiders (Araneae), for example, mites (Acari), such as ticks (Ixodidae), for example, Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp., such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp., such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp., such as Brevipalpus phoenicis; Tetranychidae spp., such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis.

[0263] In one embodiment of the present invention, there is provided a compound of formula (I) which is useful for controlling insects selected from sucking or piercing insects, such as insects from the genus Thrips, Diptera, and Hemiptera, particularly the following species:

[0264] Thrips genus: Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, and Thrips tabaci,

[0265] Diptera: Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga haemorrhoidalis, Sarcophaga spp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, Tipula oleracea, and Tipula paludosa;.

[0266] Hemiptera, in particular, aphids: Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mail, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphuminsertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantiiand, and Viteus vitifolii.

[0267] In one embodiment, the present invention provides a composition comprising a biologically effective amount of a compound of formula (I) and at least one additional biologically active and compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers, and nutrients. The compounds used in the composition and used in combination with the compound of formula (I) are also referred to as active and compatible compounds.

[0268] Known and reported fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, and nutrients can be combined with at least one compound of formula (I) of the present disclosure. For example, the fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers, and nutrients disclosed and reported in WO2016156129 and / or WO2017153200 can be combined with at least one compound of formula (I) of the present disclosure.

[0269] The fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers, and nutrients reported in WO2016156129 and / or WO2017153200 are incorporated herein by reference as non-limiting examples for combination with at least one compound of formula (I) of the present disclosure.

[0270] In particular, the compounds of the present invention can form multi-component control agents and, in order to bring about a wider range of agricultural utility, can be combined with at least one additional biologically active and compatible compound (mixing partner) such as an insecticide, a fungicide, a nematicide, a bactericide, an acaricide, a growth regulator such as a rooting stimulant, a chemical sterilant, an infochemical, a repellent, an attractant, a pheromone, a feeding stimulant, other biologically active compounds, or an entomopathogenic bacterium, virus, or fungus, but not limited thereto.

[0271] Examples of such biologically active compounds or agents / mixing partners with which the compounds of formula (I) of the present invention can be combined / formulated are disclosed in WO2019072906A1 (pages 27 - 37).

[0272] In one embodiment, the biological agents for mixing with the compounds of the present invention include Bacilllus thuringiensis, Bacilllus thuringiensis delta endotoxin, and naturally occurring genetically modified virus insecticides including members of the Baculoviridae family and entomophagous fungi.

[0273] In certain examples, combinations with other invertebrate pest control compounds or agents having a similar control spectrum but different modes of action are particularly beneficial for resistance management. Accordingly, the compositions of the present invention can further comprise at least one additional invertebrate pest control compound or agent having a similar control spectrum but different modes of action in a biologically effective amount. Contacting a plant protection compound (e.g., a protein) or a plant genetically modified to express a locus of the plant with a biologically effective amount of the compound of the present invention also provides a broader spectrum of plant protection and is beneficial for resistance management.

[0274] In one embodiment of the present invention, the biologically effective amount of the compound of formula (I) in the composition ranges from 0.1 wt% to 99 wt%, preferably from 5 wt% to 50 wt% based on the total weight of the composition.

[0275] The present invention further provides a method for combating invertebrate pests, the method comprising contacting an invertebrate pest, its habitat, breeding ground, food supply, plant, seed, soil, area where the invertebrate pest is growing or can grow, material or environment, or a space to be protected from attack or infestation by the pest, with a biologically effective amount of a compound or an agriculturally acceptable salt, isomer / structural isomer, stereoisomer, diastereomer, enantiomer, tautomer, metal complex, polymorph, or its N-oxide or a combination thereof of the present invention.

[0276] The invertebrate pests are controlled, and the protection of agriculture, horticulture, and / or specialty crops, animals and human health is achieved by directly applying one or more of the compounds of the present invention in an effective amount to the environment of the pests, the area to be protected, or the pests to be eradicated, including agricultural and / or non-agricultural intrusion sites. Thus, the present invention provides a method for controlling invertebrate pests living on leaves and in soil and for protecting agricultural and / or non-agricultural crops, the method comprising contacting the invertebrate or its environment with one or more of the compounds of the present invention in a biologically effective amount, or a composition comprising at least one such compound, or a composition comprising at least one such compound and an effective amount of at least one additional biologically active compound or agent. A preferred method of contact is by spraying. Alternatively, a granular composition comprising a compound of the present invention can be applied to the leaves or soil of plants. The compounds of the present invention are effective in delivery via plant uptake by contacting the plant with a composition comprising the compound of the present invention applied as a soil drench of a liquid formulation, a granular formulation to the soil, treatment of a nursery box, or dipping of a transplant. Other methods of contact include application of the compounds or compositions of the present invention by direct and residual spraying, aerial spraying, seed coating, microencapsulation, systemic uptake, bait, ear tag, bolus, nebulizer, fumigant, aerosol, dust, and many others.

[0277] The compounds of the present invention can be incorporated into the food consumed by invertebrates or into devices such as traps. Granules or baits containing 0.01 to 5% active ingredient, 0.05 to 10% humectant, and 40 to 99% vegetable wheat flour are effective in controlling soil insects at very low application rates, particularly at lethal doses of the active ingredient by ingestion without direct contact. The compounds of the present invention can be applied in their pure state, but in most cases, the application involves one or more compounds together with suitable carriers, diluents, and surfactants, and in some cases, the application of formulations in combination with food depending on the intended end use. Preferred methods of application include spraying an aqueous dispersion or purified oil solution of the compound. Combinations with spray oils, spray oil concentrations, spreaders, stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance the efficacy of the compound.

[0278] The application rate required for effective control (i.e., the "biologically effective amount") varies depending on factors such as the species of invertebrate to be controlled, the life cycle of the pest, its life stage, its size, location, time, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, etc. Under normal circumstances, an application rate of about 0.01 to 2 kg of active ingredient per hectare is sufficient to control pests in an agricultural ecosystem, but in some cases 0.0001 kg / hectare may be sufficient, or 8 kg / hectare may be required. For non-agricultural uses, the effective usage rate is in the range of about 1.0 to 50 mg per square meter, but in some cases 0.1 mg per square meter may be sufficient, or 150 mg per square meter may be required. A person skilled in the art can readily determine the biologically effective amount required to achieve the desired level of control of invertebrate pests.

[0279] Animal pests, namely insects, spiders, and nematodes, plants, the soil or water in which the plants are growing can be brought into contact with a compound of formula (I), its N-oxide and salts, or a composition containing them by application methods known in the art. Thus, "contact" includes both direct contact (applying the compound / composition directly to the animal pest or plant, typically to the leaves, stems, or roots of the plant) and indirect contact (applying the compound / composition to the location of the animal pest or plant).

[0280] The compounds or control compositions containing them of the present invention can be used to protect growing plants and crops from attack or infestation by animal pests, particularly insects, spider mites, or spiders, by bringing the plant / crop into contact with a pesticidally effective amount of at least one compound of the present invention. The term "crop" refers to both growing and harvested crops.

[0281] In one embodiment, the present invention provides a method for protecting a crop from attack or infestation by invertebrate pests, comprising bringing the crop into contact with a biologically effective amount of a compound or composition of the present invention, its isomers, polymorphs, N-oxides, or salts.

[0282] The compounds of the present invention are used in the form of themselves or compositions by treating plant propagation materials such as insects or plants, seeds, soil, surfaces, materials, or rooms protected from pesticidal attack with an insecticidally effective amount of the active compound. Application can be carried out both before and after infection of the plant propagation materials such as plants, seeds, soil, surfaces, materials, or rooms by insects.

[0283] In one embodiment, the present invention provides a method for protecting seeds from soil insects and protecting the roots and shoots of seedlings from soil and foliar insects, comprising bringing the seeds into contact with a compound or composition of the present invention, its N-oxide, or salts before sowing and / or after pre-germination.

[0284] Furthermore, the present invention provides a method for treating or protecting an animal against infestation or infection by a parasite, the method comprising administering or applying to the animal a biologically effective amount of a compound or composition of the present invention, an isomer, polymorph, N-oxide, or veterinarily acceptable salt thereof, orally, topically, or parenterally.

[0285] When used for treating crop plants, the application rate (effective dosage) of the compounds of the present invention can range from 1 gai to 5000 gai per hectare of agricultural or horticultural crops, preferably from 25 g to 600 g per hectare, more preferably from 50 g to 500 g per hectare.

[0286] The compounds and compositions of the present invention are particularly useful for controlling a number of insects on various cultivated plants, such as cereals, root crops, oil crops, vegetables, spices, ornamental plants, such as durum wheat and other wheats, barley, oats, rye, maize (fodder maize and sugar maize / sweet corn and field corn), soybeans, oil crops, rape, cotton, sunflowers, bananas, rice, rapeseed, turnips, sugar beets, fodder beets, eggplants, potatoes, grasses, lawns, turf, forage grasses, tomatoes, leeks, pumpkins / squashes, cabbages, iceberg lettuces, peppers, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants, such as potatoes, sugarcane, tobacco, grapes, petunias, geraniums / pelargoniums, pansies, and impatiens.

[0287] In particular, the compounds or compositions of the present invention are useful for protecting agricultural crops, such as cereals, maize, rice, soybeans and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus fruits and citrus trees, any horticultural plants, cucurbitaceous plants, oil-containing plants, tobacco, coffee, tea, cocoa, sugar beets, sugarcane, cotton, potatoes, tomatoes, onions, peppers, and other vegetables, as well as ornamental plants.

[0288] The compounds of the present invention are effective via both contact (via soil, glass, walls, bed nets, carpets, plant parts, or animal parts) and ingestion (via food or plant parts).

[0289] The compounds of the present invention can also be applied to non-crop invertebrate pests such as ants, termites, bees, flies, mosquitoes, crickets, or cockroaches. When used against the above non-crop pests, the compounds of the present invention are preferably used in a food composition.

[0290] The food can be a liquid, solid, or semi-solid preparation (e.g., gel). Solid food can be formed into various shapes and forms suitable for each application, such as granules, blocks, sticks, or disks. Liquid food can be filled into various devices, such as a lidless container, a spray device, a droplet source, or an evaporation source, to ensure proper application. The gel can be based on an aqueous or oily matrix and can be formulated according to specific requirements from the viewpoints of adhesiveness, moisture retention, or aging characteristics.

[0291] The food used in the composition is a product that is attractive enough to stimulate insects such as ants, termites, bees, flies, mosquitoes, crickets, or cockroaches to eat it. The attractiveness can be manipulated using feeding stimulants or sex pheromones. Feeding stimulants are selected from, for example, but not limited to, animal and / or plant proteins (meat blood meal, fish blood meal, insect parts, egg yolk), animal and / or plant-derived fats and oils, or especially monosaccharides, oligosaccharides, or polyorganic sugars derived from sucrose, lactose, fructose, dextrose, glucose, starch, pectin, or even molasses or honey. Fresh or spoiled parts of fruits, crops, plants, animals, insects, or specific parts thereof can also function as feeding stimulants. Sex pheromones are known to be more insect-specific. Specific pheromones are described in the literature and are known to those skilled in the art.

[0292] When used in bait compositions, typical contents of the active ingredient are from 0.001% to 15% by weight, preferably from 0.001% to 5% by weight of the active compound.

[0293] Formulations of the compounds of the invention as aerosols (e.g., in spray cans), oil sprays, or pump sprays are very suitable for non-expert users for controlling pests such as flies, fleas, mites, mosquitoes, or cockroaches. The recipe for an aerosol preferably consists of the active compound, a solvent such as a lower alcohol (e.g., methanol, ethanol, propanol, butanol), a ketone (e.g., acetone, methyl ethyl ketone), a paraffin hydrocarbon having a boiling range of about 50 to 250 °C (e.g., kerosene), dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, an aromatic hydrocarbon such as toluene, xylene, water, further auxiliaries such as an emulsifier such as sorbitol monooleate, oleyl ethoxylate having 3 to 7 mol of ethylene oxide, a fatty alcohol ethoxylate, an essential oil such as an ether oil, an ester of a medium-chain fatty acid and a lower alcohol, an aromatic carbonyl compound, and, where appropriate, a stabilizer such as sodium benzoate, an amphoteric surfactant, a lower epoxide, triethyl orthoformate, and, if desired, a propellant such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or a mixture of these gases.

[0294] Oil spray formulations differ from aerosol recipes in that no propellant is used. When used in spray compositions, the content of the active ingredient is from 0.001 to 80% by weight, preferably from 0.01 to 50% by weight, most preferably from 0.01 to 15% by weight.

[0295] The compounds of the invention and their respective compositions can also be used in mosquito coils and fumigation coils, smoke cartridges, vaporizer plates or long-term vaporizers, and can also be used in moth papers, moth pads, or other heat-independent vaporizer systems.

[0296] Methods for controlling insect-transmitted infections (e.g., malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) using the compounds of formula (I) and their respective compositions also include the treatment of the surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing, mosquito nets, tsetse fly traps, etc. Insecticidal compositions for application to fibers, fabrics, knitted products, nonwovens, netting materials, or foils, and tarpaulins preferably comprise a mixture containing an insecticide, optionally a repellent and at least one binder. Suitable repellents are, for example, Ν,Ν-diethyl-meta-toluamide (DEET), Ν,Ν-diethylphenylacetamide (DEPA), 1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperidine, (2-hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-1,3-hexanediol, indalone, methyl neodecanamide (MNDA), pyrethroids not used for insect control, for example, {(+ / -)-3-allyl-2-methyl 4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate (Esbiothrin)), limonene, eugenol, (+)-eucamalol (1), (-)-l-epi-eucamalol and other plant extracts or repellents derived from or identical to 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 vinyl esters of fatty acids (such as vinyl acetate and vinyl versatate), acrylic and methacrylic acid esters of alcohols, such as butyl acrylate, 2-ethylhexyl acrylate, and methyl acrylate, mono- and di-ethylenically unsaturated hydrocarbons, such as styrene, and aliphatic dienes, such as polymers and copolymers of butadiene.

[0297] The impregnation of curtains and mosquito nets is generally carried out by immersing the fibrous material in an emulsion or dispersion of the insecticide or spraying them onto the net.

[0298] The compounds of the present invention and their compositions can be used to protect wooden materials such as trees, fences, and sleepers, as well as buildings such as houses, sheds, and factories, as well as building materials, furniture, leather, fibers, vinyl products, electric wires, and cables from ants and / or termites, and to control ants and termites from causing harm to crops or humans (for example, when pests invade houses and public facilities). The compounds of the present invention are not only applied to the surrounding soil surface or the soil under the floor to protect wooden materials, but also to the surface of the concrete under the floor, wooden products such as floor posts, beams, plywood, and furniture, wooden products such as particle board and half board, and vinyl products such as coated electric wires and vinyl sheets, and heat insulating materials such as styrofoam.

[0299] In the case of application against ants that cause harm to crops or humans, the compounds of the present invention are applied to the crops or the surrounding soil, or directly to the ant nests, etc.

[0300] Seed treatment

[0301] The present invention further provides treated seeds containing an amount of the compound of the present invention in the range of about 0.0001% to about 1% by weight of the seeds before treatment.

[0302] The compounds of the present invention are also suitable for seed treatment to protect seeds from insect pests, particularly insect pests inhabiting the soil and mite pests, and to protect the roots and shoots of the resulting plants from soil pests and foliar insects.

[0303] The compounds of the present invention are particularly useful for protecting seeds from soil pests and for protecting the roots (larvae of scarab beetles, termites, larvae of rice water weevils) and shoots of the resulting plants from soil pests and foliar insects. Protection of the roots and shoots of the resulting plants is preferred. More preferred is to protect the shoots of the resulting plants from sap-sucking insects, and most preferred is protection from aphids, leafhoppers, thrips, and whiteflies.

[0304] Accordingly, the present invention provides a method for protecting seeds from insects, especially soil insects, and for protecting the roots and shoots of seedlings from insects, especially soil and foliar insects, which comprises contacting the seeds with a compound of the invention before sowing and / or after pre-germination. Particularly preferred is a method in which the roots and shoots of plants are protected, more preferably a method in which the shoots of plants are protected from sap-sucking insects, and most preferably a method in which the shoots of plants are protected from aphids.

[0305] The term "seed" encompasses all kinds of seeds and plant propagules including but not limited to true seeds, seed parts, suckers, bulbs, corms, fruits, tubers, grains, cuttings, cut shoots, etc., and in a preferred embodiment means true seeds.

[0306] The term "seed treatment" includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, etc.

[0307] The present invention also includes seeds coated with an active compound or seeds containing an active compound. The seeds can be coated with a seed coating composition containing a compound of the invention. For example, the seed coating compositions reported in EP3165092, EP3158864, WO2016198644, WO2016039623, WO2015192923, CA2940002, US2006150489, US2004237395, WO2011028115, EP2229808, WO2007067042, EP1795071, EP1273219, WO200178507, EP1247436, NL1012918, and CA2083415.

[0308] The term "coated and / or containing" generally means that the active ingredient is for the most part on the surface of the propagation product at the time of application, although depending on the method of application, a greater or lesser portion of the ingredient may penetrate into the propagation product. When the propagation product is (re)planted, it can absorb the active ingredient together with the moisture.

[0309] Suitable seeds are those of cereals, root crops, oil crops, vegetables, spices, ornamental plants, for example, durum wheat and other wheats, barley, oats, rye, maize (feed maize and sugar maize / sweet corn and feed maize), soybeans, oil crops, rape, cotton, sunflowers, bananas, rice, rapeseed, turnips, sugar beets, fodder beets, eggplants, potatoes, grasses, lawns, turf, forage grasses, tomatoes, leeks, pumpkins / squashes, cabbages, iceberg lettuce, peppers, cucumbers, melons, brassica seeds, melons, beans, peas, garlic, onions, carrots, tuberous plants, for example, potatoes, sugarcane, tobacco, grapes, petunias, geraniums / pelargoniums, pansies, and impatiens.

[0310] Furthermore, the compounds of the invention can be used for treating seeds derived from plants that are resistant to the action of herbicides or fungicides or insecticides for breeding, including genetic engineering methods.

[0311] For example, the compounds of the invention can be used for treating seeds derived from plants that are resistant to herbicides from the group consisting of sulfonylureas, imidazolinones, glufosinate-ammonium or glyphosate-isopropylammonium, and similar active substances (see, for example, EP242236, EP242246) (WO92 / 00377) (EP257993, US5013659), or can be used in transgenic crop plants, for example, cotton, that have the ability to produce Bacillus thuringiensis toxins (Bt toxins) that render the plant resistant to specific pests (EP142924, EP193259).

[0312] Furthermore, the compounds of the invention can be used for the treatment of seeds from plants having modified characteristics compared to existing plants, which can be produced, for example, by conventional breeding methods and / or generation of mutants or by recombinant procedures. For example, recombinant modification of crop plants for the purpose of modifying starch synthesized in the plant (e.g., WO92 / 11376, WO92 / 14827, WO91 / 19806) or some cases of transgenic crop plants having a modified fatty acid composition (WO91 / 13972) have been described.

[0313] The application of the compounds of the invention for seed treatment is carried out by spraying or dusting the seeds before sowing of the plant and before emergence of the plant.

[0314] Compositions particularly useful for seed treatment are, 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)

[0315] Conventional seed treatment formulations include, for example, flowable concentrates FS, solutions LS, powders for dry treatment DS, water-dispersible powders WS for slurry treatment, water-soluble powders SS, emulsions ES and EC, and gel formulations GF. These formulations can be applied to diluted or undiluted seeds. Application to the seeds is carried out directly on the seeds before sowing or after pre-germination of the seeds.

[0316] In one embodiment, an FS formulation is used for seed treatment. Typically, an FS formulation can contain 1 - 800 g / l of active ingredient, 1 - 200 g / l of surfactant, 0 - 200 g / l of antifreeze, 0 - 400 g / l of binder, 0 - 200 g / l of pigment, and up to 1 liter of solvent, preferably water.

[0317] In particular, the FS formulation of the compounds of the present invention for seed treatment generally contains from 0.1 to 80% by weight (1 to 800 g / l) of active ingredient, from 0.1 to 20% by weight (1 to 200 g / l) of at least one surfactant, for example from 0.05 to 5% by weight of wetting agent, and from 0.5 to 15% by weight of dispersant, up to 20% by weight, for example 5 to 20%, of antifreeze, from 0 to 15% by weight, for example 1 to 15% by weight, of pigment and / or dye, from 0 to 40% by weight, for example 1 to 40% by weight, of binder (sticker / adhesive), optionally up to 5% by weight, for example 0.1 to 5% by weight, of thickener, optionally 0.1 to 2% of defoamer, and optionally, for example in an amount of 0.01 to 1% by weight, of biocide, preservatives such as antioxidants, and up to 100% by weight of filler / vehicle.

[0318] The seed treatment formulation may further contain a binder and optionally a colorant.

[0319] The binder can be added to improve the adhesion of the active material to the treated seeds. Suitable binders are homopolymers and copolymers derived from alkylene oxides such as ethylene oxide or propylene oxide, polyvinyl acetate, polyvinyl alcohol, polyvinyl pyrrolidone, and their copolymers, ethylene-vinyl acetate copolymers, acrylic homopolymers and copolymers, polyethylene amines, polyethylene amides, and polyethylene pyrimidines, polysaccharides such as cellulose, tylose, and starch, polyolefin homopolymers and copolymers such as olefin / maleic anhydride copolymers, polyurethanes, polyesters, polystyrene homopolymers and copolymers.

[0320] Optionally, a colorant can also be included in the formulation. Suitable colorants or dyes for the seed treatment formulation are Rhodamine B, C.I. Pigment Red 112, C.I. Solvent Red 1, Pigment Blue 15:4, Pigment Blue 15:3, Pigment Blue 15:2, Pigment Blue 15:1, Pigment Blue 80, Pigment Yellow 1, Pigment Yellow 13, Pigment Red 112, Pigment Red 48:2, Pigment Red 48:1, Pigment Red 57:1, Pigment Red 53:1, Pigment Orange 43, Pigment Orange 34, Pigment Orange 5, Pigment Green 36, Pigment Green 7, Pigment White 6, Pigment Brown 25, Basic Violet 10, Basic Violet 49, Acid Red 51, Acid Red 52, Acid Red 14, Acid Blue 9, Acid Yellow 23, Basic Red 10, Basic Red 108.

[0321] An example of a gelling agent is carrageenan (Satiagel (registered trademark)).

[0322] In the treatment of seeds, the application rate of the compounds of the present invention is generally from 0.1 g to 10 kg per 100 kg of seeds, preferably from 1 g to 5 kg per 100 kg of seeds, more preferably from 1 g to 1000 g, particularly from 1 g to 200 g per 100 kg of seeds. Accordingly, the present invention also provides seeds comprising a compound of formula (I) as defined herein or an agriculturally useful salt of I. The amount of compound I or its agriculturally useful salt generally varies from 0.1 g to 10 kg per 100 kg of seeds, preferably from 1 g to 5 kg per 100 kg of seeds, particularly from 1 g to 1000 g. In the case of certain crops such as lettuce, the amount can be higher.

[0323] Animal health

[0324] The present invention also provides agricultural and / or veterinary compositions comprising at least one compound of the present invention.

[0325] The present invention further relates to the use of a compound, an N-oxide, or a veterinarily acceptable salt thereof, or a composition of the present invention, in the preparation of a medicament for treating or protecting an animal from infestation or infection by invertebrate pests or parasites.

[0326] The compounds of formula (I), their N-oxides, and / or veterinarily acceptable salts are also particularly suitable for use in controlling parasites in and on animals.

[0327] Accordingly, one object of the present invention is to provide a novel method for controlling parasites in and on animals. Another object of the present invention is to provide a control agent that is safer for animals. Another object of the present invention is to provide a control agent for animals that can be used at a lower dose than existing control agents. Another object of the present invention is to provide a control agent for animals that provides long-term residual control of parasites.

[0328] The present invention also relates to a composition comprising a parasitically effective amount of at least one compound of formula (I), its N-oxide, or a veterinarily acceptable salt thereof, and an acceptable carrier for controlling parasites in and on animals.

[0329] The present invention also provides a method for treating, controlling, preventing, and protecting an animal against infestation and infection by parasites, comprising administering or applying orally, topically, or parenterally to the animal a parasitically effective amount of a compound of the present invention or a composition containing the same.

[0330] The present invention also provides a process for preparing a composition for treating, controlling, preventing, or protecting an animal against infestation or infection by parasites, comprising a parasitically effective amount of a compound of the present invention or a composition containing the same.

[0331] The activity of the compounds against agricultural pests does not suggest suitability for the control of endoparasites and ectoparasites in and on animals, which require, for example, low non-emetic dosages in the case of oral administration, compatibility of metabolism with animals, low toxicity, and safe handling.

[0332] Surprisingly, it has now been found that the compounds of the present invention are suitable for controlling endoparasites and ectoparasites in and on animals.

[0333] The compounds of the present invention and compositions containing them are preferably used for controlling and preventing infestation and infection in animals including warm-blooded animals (including humans) and fish. They are suitable, for example, for controlling and preventing infestation and infection in mammals such as cattle, sheep, pigs, camels, deer, horses, pigs, poultry, rabbits, goats, dogs, and cats, water buffalo, donkeys, fallow deer, and reindeer, and fur-bearing animals such as mink, chinchilla, and raccoon, birds such as hens, geese, turkeys, and ducks, and fish such as freshwater and saltwater fish such as trout, carp, and eels.

[0334] The compounds of the present invention and compositions containing them are preferably used for controlling and preventing infestation and infection in domestic animals such as dogs or cats.

[0335] Infestation of warm-blooded animals and fish includes, but is not limited to, lice, fleas, mites, fly larvae, sheep ked flies, stable flies, muscoid flies, biting flies, flies, myiasis fly larvae, ticks, bedbugs, mosquitoes, and fleas.

[0336] The compounds of the present invention and compositions containing them are suitable for systemic and / or non-systemic control of ectoparasites and / or endoparasites. They can be active against all or some stages of the disease.

[0337] The compounds of the present invention are particularly useful for controlling ectoparasites.

[0338] The compounds of the present invention are particularly useful for controlling the following orders and species of parasites: fleas (order Siphonaptera), for example, Ctenocephalides felis, Ctenocephalides cams, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus; cockroaches (order Blattaria Blattodea), for example, Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis; flies, mosquitoes (order 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 pipiens, Culex nigrip quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilusintestinalis, 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 spp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, lice (Phthiraptera), for example, Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus, and Solenopotes capillatus, mites and parasitic mites (Parasitiformes): mites (Ixodida), for example, Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryommamaculatum, Ornithodorus hermsi, Ornithodorus turicata, and parasitic mites (Mesostigmata), for example, Orinithonyssus bacoti, and Dermanyssus gallinae, Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapisa 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., Sarcptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptes spp., bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius spp., Panstrongylus spp., and Arilus critatus, Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp., Mallophagida (suborders Arnblycerina, and Ischnocerina), for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.

[0339] Roundworms:

[0340] Wipeworm larvae, and Trichinosis (Trichosyringida), for example, Trichinellidae (Trichinella spp.), (Trichuridae), Trichuris spp., Capillaria spp., Rhabditida, for example, Rhabditis spp., Strongyloides spp., Helicephalobus spp., Strongylida, for example, Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus, Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylus abstrusus, and Dioctophyma renale, Intestinal roundworms (Ascaridida), for example, Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp.and Oxyuris equi, Camallanida, for example, Dracunculus medinensis (guinea worm), Spirurida, for example, Thelazia spp., Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp., DiDipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp., Thorny headed worm (Acanthocephala), for example, Acanthocephalus spp., Macracanthorhynchus hirudinaceus, and Oncicola spp., Planarian (Plathelminthe): Fluke (Trematoda), for example, Faciola spp., Fascioloides magtna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria a lata, Paragonimus spp., and Nanocyetes spp., Cercomeromorpha, particularly Cestoda (Tapeworms), for example, 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 also Hymenolepis spp.

[0341] The compounds of formula (I) and compositions containing them are particularly useful for the control of pests from Diptera, Siphonaptera, and Ixodida.

[0342] In one embodiment, the present invention provides the use of the compounds of formula (I) and compositions containing them for repelling mosquitoes.

[0343] In one embodiment, the present invention provides the use of the compounds of formula (I) and compositions containing them for repelling flies.

[0344] In one embodiment, the present invention provides the use of the compounds of formula (I) and compositions containing them for repelling fleas.

[0345] The use of the compounds of the present invention and compositions containing them for repelling mites is yet another embodiment of the present invention.

[0346] The compounds of the present invention are also particularly useful for controlling endoparasites (roundworms, hookworms, and planarians).

[0347] In one embodiment, the administration of the compounds of the present invention can be carried out both prophylactically and therapeutically.

[0348] In another embodiment, the administration of the compounds of the present invention is carried out orally, topically / dermally, or parenterally, either directly or in the form of a suitable preparation.

[0349] For oral administration to warm-blooded animals, the compounds of the present invention can be formulated as animal feed, animal feed premixes, animal feed concentrates, boluses, solutions, pastes, suspensions, drenches, gels, tablets, boluses, and capsules. Further, the compounds of the present invention can be administered to animals in their drinking water. For oral administration, the dosage form selected should provide the animal with 0.01 mg / kg to 100 mg / kg of the compound of the present invention per day, preferably 0.5 mg / kg to 100 mg / kg of the compound of the present invention per day based on the animal's body weight.

[0350] Alternatively, the compounds of the present invention can be administered to animals parenterally, for example, into the rumen, intramuscularly, intravenously, or subcutaneously. 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 implants for subcutaneous administration. Furthermore, the compounds of the present invention can be administered to animals transdermally. In the case of parenteral administration, the dosage form selected needs to provide the animal with 0.01 mg / kg to 100 mg / kg of the compound of the present invention per day based on the animal's body weight.

[0351] The compounds of the present invention can also be applied topically to animals in the form of dips, powders, dusts, collars, medals, sprays, shampoos, spot-ons, and pour-ons, as well as in the form of ointments or water-in-oil or oil-in-water emulsions. In the case of topical application, dip agents and spray agents usually contain 0.5 ppm to 5,000 ppm, preferably 1 ppm to 3,000 ppm, of the compound of the present invention. Furthermore, the compounds of the present invention can be formulated as ear tags for animals, especially for quadrupeds such as cattle and sheep.

[0352] Suitable preparations are solutions, for example, oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pour-on preparations, gels; emulsions and suspensions for oral or dermal administration; semi-solid preparations; preparations in which the active compound is processed in an ointment base or a water-in-oil or oil-in-water emulsion base: solid preparations, for example, powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and shaped articles containing the active compound.

[0353] Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further ingredients such as acids, bases, buffer salts, preservatives, and solubilizing agents. The solution is filtered and filled aseptically.

[0354] Suitable solvents are physiologically acceptable solvents such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycol, N-methylpyrrolidone, 2-pyrrolidone, and mixtures thereof.

[0355] The active compound can optionally be dissolved in a physiologically acceptable vegetable oil or synthetic oil suitable for injection.

[0356] Suitable solubilizers are solvents that promote the dissolution of the active compound in the main solvent or prevent its precipitation. Examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan esters.

[0357] Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n-butanol.

[0358] Oral solutions are administered directly. Concentrates are administered orally after prior 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, and no sterilization procedure is required.

[0359] Solutions for use on the skin are dropped, spread, rubbed, sprinkled, or sprayed.

[0360] Solutions for use on the skin are prepared according to the state of the art and as described above for injection solutions, and no sterilization procedure is required.

[0361] More preferred solvents are polypropylene glycol, phenylethanol, phenoxyethanol, esters such as ethyl acetate or butyl acetate, benzyl benzoate, alkylene glycol alkyl ethers, such as ethers like dipropylene glycol monomethyl ether, ketones such as acetone, methyl ethyl ketone, aromatic hydrocarbons, vegetable oils and synthetic oils, dimethylformamide, dimethylacetamide, transcutol, solketal, propylene carbonate, and mixtures thereof.

[0362] It may be advantageous to add a thickener during preparation. Suitable thickeners are inorganic thickeners, such as bentonite, colloidal silica, aluminum monostearate, and organic thickeners, such as cellulose derivatives, polyvinyl alcohol and its copolymers, acrylates and methacrylates.

[0363] The gel is applied or spread on the skin or introduced into a body cavity. The gel is prepared by treating a solution prepared as described for injection solutions with a thickener sufficient to obtain a transparent material having a consistency like that of an ointment. The thickener used is the above-mentioned thickener.

[0364] The poultice preparation is poured or sprayed onto a limited area of the skin, and the active compound penetrates the skin and acts systemically. The poultice preparation is prepared by dissolving, suspending, or emulsifying the active compound in a suitable skin-compatible solvent or solvent mixture. Optionally, other auxiliaries such as colorants, bioabsorption promoters, antioxidants, light stabilizers, adhesives, etc. are added.

[0365] Suitable solvents include, for example, water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers, ethers 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, methylpyrrolidone, n-butylpyrrolidone or n-octylpyrrolidone, n-alkylpyrrolidones such as N-methylpyrrolidone, 2-pyrrolidone, 2,2-dimethyl-4-oxy-methylene-1,3-dioxolane, or glycerol formal.

[0366] Suitable colorants are, for example, all colorants that are approved for use in animals and can be dissolved or suspended.

[0367] Suitable absorption promoters are, for example, dimethyl sulfoxide, diffusion oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils, and copolymers thereof with polyethers, fatty acid esters, triglycerides, or fatty alcohols.

[0368] Suitable antioxidants are, for example, sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, or tocopherol.

[0369] Suitable light stabilizers are, for example, novantisolic acid. Suitable adhesives are, for example, cellulose derivatives, starch derivatives, polyacrylates, or natural polymers such as alginates, gelatin. The emulsion can be administered orally, topically, or by injection. The emulsion can be either oil-in-water or water-in-oil type.

[0370] They are prepared by dissolving the active compound in either a hydrophobic or a hydrophilic phase, and homogenizing this, with the aid of a suitable emulsifier and, if appropriate, other auxiliaries such as colorants, absorption promoters, preservatives, antioxidants, light stabilizers, viscosity enhancing substances, in a solvent of the other phase.

[0371] Suitable hydrophobic phases (oils) are liquid paraffin, silicone oil, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as di(caprylic / capric acid) glyceride, triglyceride mixtures with vegetable fatty acids of chain length C1 - C 12 and partial glyceride mixtures of saturated or unsaturated fatty acids which may also contain hydroxyl groups, mono - and diglycerides of Cs - do fatty acids, fatty acid esters such as ethyl stearate, di - n - butyryl adipate, hexyl laurate, dipropylene glycol pelargonate, esters of medium - chain branched fatty acids and saturated fatty alcohols of chain length C 16 - C 18 such as isopropyl myristate, isopropyl palmitate, esters of saturated fatty acids of chain length C 12 - C 18 such as caprylic / capric acid esters of saturated fatty acid esters, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, wax - like fatty acid esters such as synthetic beaver castor fat, dibutyl phthalate, diisopropyl adipate, and related ester mixtures thereof, fatty alcohols such as isotridecyl alcohol, 2 - octyldodecanol, cetylstearyl alcohol, oleyl alcohol, and fatty acids such as oleic acid, and mixtures thereof. Suitable hydrophilic phases are water, alcohols such as propylene glycol, glycerol, sorbitol, and mixtures thereof.

[0372] Suitable emulsifiers are, for example, nonionic surfactants such as polyethoxylated castor oil, polyethoxylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether; amphoteric surfactants such as disodium N-lauryl-p-iminodipropionate or lecithin.

[0373] Suitable anionic surfactants are, for example, sodium lauryl sulfate, fatty alcohol ether sulfates, mono / dialkyl polyglycol ether orthophosphate monoethanolamine salts. Suitable cationic surfactants are cetyltrimethylammonium chloride.

[0374] Suitable further auxiliaries are, for example, substances that enhance viscosity and stabilize the emulsion, such as carboxymethyl cellulose, methyl cellulose, and other celluloses, and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycol, waxes, colloidal silica, or mixtures of the above substances.

[0375] The suspensions can be administered orally or topically / dermally. They are prepared, if necessary, by adding other auxiliaries such as wetting agents, colorants, bioavailability enhancers, preservatives, antioxidants, light stabilizers, and suspending the active compound in a suspending agent.

[0376] Liquid suspensions are all homogeneous solvents and solvent mixtures.

[0377] Suitable wetting agents (dispersants) are the above-mentioned emulsifiers.

[0378] Other auxiliaries that may be mentioned are the above-mentioned ones.

[0379] The semi-solid preparations can be administered orally or topically / dermally. They differ from the above suspensions and emulsions only in that they have a high viscosity.

[0380] For the manufacture of solid preparations, the active compounds are mixed with suitable excipients, optionally with the addition of auxiliaries, and brought into the desired form.

[0381] All suitable excipients are physiologically acceptable solid inert substances. Those used are inorganic and organic substances. Inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, bicarbonates, aluminum oxide, titanium oxide, silicic acid, argillaceous earth, precipitated or colloidal silica, or phosphates. Organic substances are, for example, sugars, cellulose, foods and feeds such as milk powder, animal meal, cereal meal and flakes, starch, etc.

[0382] Suitable auxiliaries are the above preservatives, antioxidants, and / or colorants.

[0383] Other suitable auxiliaries are lubricants and flow promoters such as magnesium stearate, stearic acid, talc, bentonite, disintegration promoters such as starch or crosslinked polyvinylpyrrolidone, binders such as starch, gelatin, or linear polyvinylpyrrolidone, and dry binders such as microcrystalline cellulose.

[0384] Generally, an "effective anthelmintic amount" means the amount of the active ingredient necessary to achieve an observable effect on growth, including effects such as necrosis, death, retardation, prevention, removal, destruction, or otherwise a reduction in the occurrence and activity of the target organisms. The effective anthelmintic amount can vary for the various compounds / compositions used in the present invention. The effective anthelmintic amount of the composition also varies depending on general conditions such as the desired anthelmintic effect and duration, the target species, the mode of application, etc. Compositions that can be used in the present invention generally contain from about 0.001 to 95% of the compounds of the present invention.

[0385] Generally, it is preferred to apply the compounds of the present invention in a total amount of 0.5 mg / kg to 100 mg / kg per day, preferably 1 mg / kg to 50 mg / kg per day. Preparations that are ready for use contain the compound that acts on parasites, preferably ectoparasites, at a concentration of 10 ppm to 80 weight percent, preferably 0.1 to 65 weight percent, more preferably 1 to 50 weight percent, and most preferably 5 to 40 weight percent. The preparation is diluted before use and contains the compound that acts on ectoparasites at a concentration of 0.5 to 90 weight percent, preferably 1 to 50 weight percent. Further, the preparation contains the compound of the present invention against endoparasites at a concentration of 10 ppm to 2 weight percent, preferably 0.05 to 0.9 weight percent, and very particularly preferably 0.005 to 0.25 weight percent.

[0386] In one embodiment, the composition containing the compound of the present invention is applied dermally / topically.

[0387] In another embodiment, the topical application is in the form of a collar, medal, ear tag, band for fixing to a body part, and compound-containing molded articles such as adhesive strips and foils.

[0388] Generally, it is preferred to apply a solid preparation that releases the compound of the present invention at a weight of 10 mg / kg to 300 mg / kg, preferably 20 mg / kg to 200 mg / kg, and most preferably 25 mg / kg to 160 mg / kg of the treated animal over a period of 3 weeks.

[0389] For the preparation of molded articles, thermoplastics and soft plastics, as well as elastomers and thermoplastic elastomers are used. Suitable plastics and elastomers are polyvinyl resins, polyurethanes, polyacrylates, epoxy resins, celluloses, cellulose derivatives, polyamides, and polyesters that are sufficiently compatible with the compounds of the present invention. A detailed listing of plastics and elastomers, as well as the procedure for preparing molded articles, is shown in WO2003 / 086075.

[0390] Positive crop reaction:

[0391] The compounds of the present invention not only effectively control insect pests and mite pests, but also bring about an increase in yield, plant growth enhancing effects such as enhancing root growth, enhancing tolerance to drought, high salinity, high temperature, cold, frost or light radiation, improving flowering, enhancing nutrient utilization (such as improving nitrogen assimilation), improving the quality of plant products, having a greater number of effective tillers, and showing positive crop responses such as enhancing tolerance to fungi, insects, pests, etc.

[0392] Chemical Examples

[0393] The following examples illustrate the methods and procedures for preparing the compounds of the present invention, and are not limited thereto, and include the best modes contemplated by the inventors for carrying out the present invention.

[0394] Example - 1: Synthesis of 5-(3-(ethylsulfonyl)-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 38)

[0395] Step - 1: 2-(Trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5(4H)-one

[0396] To a stirred solution of 3-(trifluoromethyl)-1H-pyrazol-5-amine (2.0 g, 13.24 mmol) in anhydrous N,N-dimethylformamide (25 mL) was added dropwise a solution of ethyl (E)-3-ethoxyacrylate (2.29 g, 15.88 mmol) in anhydrous N,N-dimethylformamide (2 mL) over 15 minutes at 25 °C, followed by the addition of cesium carbonate (8.63 g, 26.50 mmol). The reaction mixture was heated at 100 °C for 16 hours. After completion of the reaction, the reaction mixture was cooled to 25 °C and diluted with water (100 mL). The reaction mixture was acidified by dropwise addition of acetic acid (4 mL) at 0 °C and then stirred at 25 °C for 2 hours. The reaction mixture was extracted twice with ethyl acetate (100 mL). The combined ethyl acetate layers were washed with brine (100 mL) and water (100 mL), dried over anhydrous sodium sulfate, concentrated to give the crude product, which was purified by silica gel column chromatography using hexane containing 60% ethyl acetate as the eluent to give 2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5(4H)-one (2.2 g, 10.83 mmol, 82% yield). 1 1H-NMR (400 MHz, DMSO-d6) δ 12.43 (s, 1H), 8.56 - 8.58 (m, 1H), 6.17 - 6.20 (m, 2H); ESI-MS (m / z) 201.95 (M - H).

[0397] Step - 2: 5-Bromo-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0398] A stirred solution of 2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5(4H)-one (2.5 g, 12.31 mmol) in 1,2-dichloroethane (25 mL) was added phosphorus(V) oxybromide (7.06 g, 24.62 mmol) at 25 °C. The reaction mixture was heated at 100 °C for 5 h. After completion of the reaction, the reaction mixture was cooled to 25 °C, diluted with water (100 mL), and extracted with ethyl acetate (2 x 100 mL). The combined ethyl acetate layers were washed with saturated sodium hydrogen carbonate solution (200 mL), brine (100 mL), and water (100 mL), dried over anhydrous sodium sulfate, concentrated to give the crude product, which was purified by silica gel column chromatography using hexane containing 10% ethyl acetate as the eluent to give 5-bromo-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine. 1 1H-NMR (400 MHz, DMSO-d6) δ 9.20 (d, J = 7.3 Hz, 1H), 7.50 (d, J = 7.3 Hz, 1H), 7.28 (s, 1H).

[0399] Step-3: 5-(5-Bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0400] A stirred solution of 5-bromo-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (4.50 g, 16.92 mmol) and 5-bromo-3-(ethylthio)-2-(tributylstannyl)pyridine (12.87 g, 25.0 mmol) in anhydrous tetrahydrofuran (100 mL) was thoroughly deoxygenated by subjecting it to three cycles of vacuum / nitrogen, and then the reaction was terminated by adding tetrakis(triphenylphosphine)palladium(0) (1.95 g, 1.69 mmol) and copper(I) bromide (0.48 g, 3.38 mmol). The reaction mixture was heated at 70 °C for 2 h. After completion of the reaction, the reaction mixture was cooled to 25 °C, diluted with water (50 mL), and extracted with ethyl acetate (2 x 100 mL). The combined ethyl acetate layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product, which was purified by column chromatography on silica gel using hexane containing 10% ethyl acetate as the eluent to give 5-(5-bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (3.5 g, 8.68 mmol, 51% yield) as a solid phase. 1 1H-NMR (400 MHz, DMSO-d6) δ 9.31 (dd, J = 7.3, 0.9 Hz, 1H), 8.63 (d, J = 1.8 Hz, 1H), 8.15 (d, J = 1.8 Hz, 1H), 7.87 (d, J = 7.3 Hz, 1H), 7.37 (s, 1H), 3.05 (q, J = 7.3 Hz, 2H), 1.23 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 404.70, 405.70 [(MH)+ + Br 79, 81 .

[0401] Step - 4: 5-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0402] A solution of 5-(5-bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (4.0 g, 9.92 mmol) in dichloromethane (100 mL) was cooled to 0 - 5 °C, and m-chloroperbenzoic acid (5.71 g, 19.84 mmol) was added portionwise. The reaction mixture was stirred at 25 °C for 5 h. After completion of the reaction, the reaction mixture was cooled to 0 °C, quenched by dropwise addition of 2N sodium hydroxide solution (50 mL), and extracted with dichloromethane (50 mL). The dichloromethane layer was washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by CombiFlash™ system using silica gel with hexane containing 25% ethyl acetate as the eluent to give 5-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (3.0 g, 6.89 mmol, 69% yield) as a solid. 1 1H-NMR (400 MHz, DMSO-d6) δ 9.45 (dd, J = 7.3, 0.9 Hz, 1H), 9.22 (d, J = 2.1 Hz, 1H), 8.65 (d, J = 2.1 Hz, 1H), 7.65 (d, J = 7.3 Hz, 1H), 7.49 (s, 1H), 3.93 (q, J = 7.4 Hz, 2H), 1.29 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 434.65, 435.65 [(MH)+ + Br 79, 81 .

[0403] Step-5: 5-(3-(Ethylsulfonyl)-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0404] 5-(5-Bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (300 mg, 0.69 mmol) and 5-methyl-3-(trifluoromethyl)-1H-pyrazole (103 mg, 0.69 mmol) were added to a stirred solution of anhydrous N,N-dimethylformamide (6 mL). Potassium carbonate (191 mg, 1.38 mmol) was added thereto. The reaction mixture was stirred at 90 °C for 24 hours. After completion of the reaction, the reaction mixture was diluted with ice water (60 mL) and extracted with ethyl acetate (2 x 30 mL). The combined ethyl acetate layers were washed with brine (50 mL) and water (100 mL). Dried over anhydrous sodium sulfate and concentrated to obtain a crude product, which was purified by column chromatography on silica gel using hexane containing 40% ethyl acetate as an eluent to obtain 5-(3-(ethylsulfonyl)-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (61 mg, 0.12 mmol, yield 18%). 1 H-NMR (400 MHz, DMSO-d6) δ 9.49 (dd, J = 7.3, 0.6 Hz, 1H), 9.35 (d, J = 2.4 Hz, 1H), 8.68 (d, J = 2.4 Hz, 1H), 7.73 (d, J = 7.3 Hz, 1H), 7.53 (s, 1H), 6.94 (s, 1H), 3.98 (q, J = 7.3 Hz, 2H), 2.54 (s, 3H), 1.32 (t, J = 7.5 Hz, 3H); ESI-MS (m / z) 504.95 (MH) + 。

[0405] Example-2: Synthesis of 5-bromo-3-(ethylthio)-2-(tributylstannyl)pyridine (Intermediate 5) in Example 1

[0406] Step-1: 2,5-Dibromopyridin-3-amine

[0407] To a stirred solution of acetic acid (50 mL) containing iron (5.94 g, 106.0 mmol), 2,5-dibromo-3-nitropyridine (12.0 g, 42.6 mmol) was added portion wise at 25 °C. The reaction mixture was stirred at 80 °C for 1 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and quenched by dropwise addition of water (100 mL). The reaction mixture was extracted with ethyl acetate (2 x 200 mL). The combined ethyl acetate layers were washed with saturated sodium bicarbonate solution (200 mL), dried over anhydrous sodium sulfate, concentrated to give the crude product, which was purified by silica gel column chromatography using hexane containing 20% ethyl acetate as eluent to give 2,5-dibromopyridine-3-amine (7.0 g, 27.8 mmol, 65% yield). 1 H-NMR (400 MHz, DMSO-d6) δ 7.64 (d, J = 2.1 Hz, 1H), 7.25 (d, J = 2.1 Hz, 1H), 5.82 (s, 2H); ESI MS (m / z) 252.50, 254.50 [(MH) + Br 79, 81 .

[0408] Step-2: 2,5-Dibromo-3-(ethylthio)pyridine

[0409] A solution of 1,2 - dichloroethane (70 mL) containing 1,2 - diethyldisulfane (4.11 mL, 33.3 mmol) was added dropwise with tert - butyl nitrite (4.96 mL, 41.7 mmol) at 25 °C, and the reaction was stirred at 40 °C for 1 hour. Then, 2,5 - dibromopyridin - 3 - amine (7.0 g, 27.8 mmol) was partially added to the above - mentioned reaction mixture, and the reaction was continued at 40 °C for 2 hours. After completion of the reaction, the reaction mixture was cooled to 25 °C and quenched by drop - wise addition of water (100 mL). The reaction mixture was extracted with dichloromethane (2 x 100 mL). The combined dichloromethane layers were washed with a saturated sodium hydrogen carbonate (100 mL) solution, dried over anhydrous sodium sulfate, and concentrated to obtain a crude product, which was purified by silica gel column chromatography using hexane containing 5% ethyl acetate as the eluent to obtain 2,5 - dibromo - 3 - (ethylthio)pyridine (5 g, 16.83 mmol, 61% yield). 1 1H - NMR (400 MHz, DMSO - d6) δ 8.29 (d, J = 2.2 Hz, 1H), 7.88 (d, J = 2.2 Hz, 1H), 3.10 (q, J = 7.3 Hz, 2H), 1.30 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 297.55, 299.55 [(MH)+ + Br 79, 81 .

[0410] Step - 3: 5 - Bromo - 3 - (ethylthio)-2-(tributylstannyl)pyridine

[0411] To a stirred solution of anhydrous toluene (15 mL) containing 2,5-dibromo-3-(ethylthio)pyridine (500 mg, 1.69 mmol) was added dropwise over 15 minutes at -78 °C a solution of anhydrous toluene (50 mL) containing n-butyllithium (2.5 M n-hexane solution) (0.8 mL, 2.02 mmol). The reaction was allowed to proceed for 1 hour while maintaining the temperature at -78 °C until the solution turned dark red. Tri-n-butylchlorotin (0.55 mL, 2.02 mmol) was added dropwise to the above reaction mixture, and the reaction was further stirred for 12 hours while warming to 25 °C. After completion of the reaction, the reaction mixture was cooled to 0 °C and quenched by dropwise addition of water (50 mL). The reaction mixture was extracted with ethyl acetate (2 x 25 mL). The combined ethyl acetate layers were washed with brine (50 mL) and water (100 mL), dried over anhydrous sodium sulfate, concentrated to give a crude product, which was purified by silica gel column chromatography using hexane containing 2% ethyl acetate as the eluent to give 5-bromo-3-(ethylthio)-2-(tributylstannyl)pyridine (200 mg, 0.39 mmol, 23% yield). 1 1H-NMR (400 MHz, DMSO-d6) δ 8.61 (q, J = 2.0 Hz, 1H), 7.93 (td, J = 6.7, 2.2 Hz, 1H), 3.06 (q, J = 7.3 Hz, 2H), 1.44-1.61 (m, 6H), 1.20-1.31 (m, 9H), 1.08-1.15 (m, 6H), 0.83 (t, J = 7.3 Hz, 9H).

[0412] Example - 3: Synthesis of 5-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 66)

[0413] Step - 1: Synthesis of 5-(3-(ethylthio)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0414] A stirred solution of a mixture of tetrahydrofuran (6 mL) and water (3 mL) containing 5-(5-bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (300 mg, 0.74 mmol) and (4-(trifluoromethoxy)phenyl)boronic acid (153 mg, 0.74 mmol) was added with sodium acetate (158 mg, 1.49 mmol) and tetrakis(triphenylphosphine)palladium(0) (25.8 mg, 0.02 mmol). The reaction mixture was degassed thoroughly by applying a vacuum / nitrogen cycle three times and heated at 85 °C for 3 hours. After completion of the reaction, the reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (100 mL). The ethyl acetate layer was separated, dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography using hexane containing 10% ethyl acetate as an eluent to give 5-(3-(ethylthio)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (200 mg, 0.41 mmol, 56% yield) as a solid. 1 H-NMR (400 MHz, DMSO-d6) δ 9.33 (dd, J = 7.3, 0.6 Hz, 1H), 8.84 (d, J = 1.8 Hz, 1H), 8.14 (d, J = 2.1 Hz, 1H), 7.97 - 8.03 (m, 3H), 7.54 (d, J = 7.9 Hz, 2H), 7.38 (s, 1H), 3.15 (q, J = 7.4 Hz, 2H), 1.27 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 485.00 (MH) + 。

[0415] Step - 2: 5-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0416] To a solution of 5-(3-(ethylthio)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (140 mg, 0.29 mmol) in dichloromethane (10 mL) was added m-chloroperbenzoic acid (166 mg, 0.58 mmol) portion wise at 0 - 5 °C. The reaction mixture was stirred at 25 °C for 5 h. After completion of the reaction, the reaction mixture was cooled to 0 °C, quenched by dropwise addition of 2N sodium hydroxide solution (50 mL), and extracted with dichloromethane (2 x 50 mL). The combined dichloromethane layers were dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified by silica gel column chromatography using hexane containing 25% ethyl acetate as the eluent to afford 5-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (80 mg, 0.16 mmol, 54% yield) as a solid. 1 H-NMR (400 MHz, DMSO-d6) δ 9.48 (dd, J = 7.3, 1.0 Hz, 1H), 9.41 (d, J = 2.2 Hz, 1H), 8.70 (d, J = 2.2 Hz, 1H), 8.09 (dt, J = 9.5, 2.6 Hz, 2H), 7.72 (d, J = 7.3 Hz, 1H), 7.60 - 7.62 (m, 2H), 7.50 (s, 1H), 3.97 (q, J = 7.4 Hz, 2H), 1.33( t, J = 7.3 Hz, 3H ); ESI MS (m / z) 516.95 (MH) + 。

[0417] Example - 4: Synthesis of 6-(3-(ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 45)

[0418] Step-1: 6-Bromo-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0419] To a stirred solution of ethanol (180 mL) containing 3-(trifluoromethyl)-1H-pyrazol-5-amine (6.0 g, 39.70 mmol) was added portion wise 2-bromomalonaldehyde (5.99 g, 39.70 mmol) at 25 °C over 15 minutes, followed by the dropwise addition of concentrated hydrochloric acid (4 mL). The reaction mixture was stirred at 25 °C for 12 hours. After completion of the reaction, the reaction volume was reduced to half. The reaction mixture was cooled to 0 °C and treated with a saturated solution of sodium hydrogen carbonate (50 mL) with stirring for 30 minutes. The resulting precipitate was collected by filtration, washed with water (50 mL), and dried under reduced pressure to give 6-bromo-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (8.0 g, 30.10 mmol, 76% yield). 1 H-NMR (400 MHz, DMSO-d6) δ 9.76 (s, 1H), 8.81 (s, 1H), 7.36 (s, 1H); ESI-MS (m / z) 266.02 (M-H).

[0420] Step-2: 6-(6-Chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0421] A stirred solution of 6-bromo-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (5.0 g, 18.80 mmol) and 6-chloro-3-(ethylthio)-2-(tributylstannyl)pyridine (14.78 g, 32.0 mmol) in anhydrous tetrahydrofuran (150 mL) was thoroughly deoxygenated by subjecting it to three cycles of vacuum / nitrogen, and then tetrakis(triphenylphosphine)palladium(0) (2.17 g, 1.88 mmol) and copper(I) bromide (0.54 g, 3.76 mmol) were added. The reaction mixture was heated at 70 °C for 2 hours. After completion of the reaction, the reaction mixture was cooled to 25 °C, diluted with water (50 mL), and extracted with ethyl acetate (2 x 100 mL). The combined ethyl acetate layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a crude product, which was purified by silica gel column chromatography using hexane containing 10% ethyl acetate as the eluent to give 6-(6-chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (3.0 g, 8.36 mmol, 45% yield) as a solid. 1 1H-NMR (400 MHz, DMSO-d6) δ 9.56 (q, J = 1.0 Hz, 1H), 8.93 (d, J = 2.1 Hz, 1H), 8.08 (d, J = 8.3 Hz, 1H), 7.64 (d, J = 8.3 Hz, 1H), 7.40 (s, 1H), 3.02 (q, J = 7.3 Hz, 2H), 1.15 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 359.70, 361.70 [(MH)+ + Cl 35, 37 .

[0422] Step - 3: 6-(6-Chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0423] A stirred solution of 6-(6-chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (3.0 g, 8.36 mmol) in dichloromethane (50 mL) was added m-chloroperbenzoic acid (4.81 g, 16.72 mmol) portion wise at 0 - 5 °C. The mixture was stirred at 25 °C for 5 h. After completion of the reaction, the reaction mixture was cooled to 0 °C, quenched by dropwise addition of 2N aqueous sodium hydroxide solution (50 mL), and extracted with dichloromethane (2 x 50 mL). The combined dichloromethane layers were dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified by silica gel column chromatography using hexane containing 25% ethyl acetate as the eluent to afford 6-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (2.5 g, 6.40 mmol, 77% yield) as a solid phase. 1 1H-NMR (400 MHz, DMSO-d6) δ 9.56 (q, J = 1.0 Hz, 1H), 8.87 (d, J = 1.8 Hz, 1H), 8.54 (d, J = 8.6 Hz, 1H), 7.99 (d, J = 8.6 Hz, 1H), 7.41 (s, 1H), 3.26 (q J = 7.3 Hz, 2H), 1.06 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 392.80, 394.80 [(MH)+ + Cl 35, 37 .

[0424] Step - 4: 6-(3-(Ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0425] A stirred solution of 6-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (300 mg, 0.77 mmol) and 5-methyl-3-(trifluoromethyl)-1H-pyrazole (115 mg, 0.77 mmol) in anhydrous N,N-dimethylformamide (3 mL) was added potassium carbonate (212 mg, 1.54 mmol). The reaction mixture was stirred at 25 °C for 12 h. After completion of the reaction, the reaction mixture was diluted with ice water (60 mL) and extracted with ethyl acetate (2 x 30 mL). The combined ethyl acetate layers were washed with brine (50 mL) and water (50 mL). Dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified by column chromatography on silica gel using hexane containing 40% ethyl acetate as eluent to give 6-(3-(ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (63 mg, 0.13 mmol, yield 16%). 1 1H-NMR (400 MHz, DMSO-d6) δ 9.49 (dd, J = 7.3, 0.6 Hz, 1H), 9.35 (d, J = 2.4 Hz, 1H), 8.68 (d, J = 2.4 Hz, 1H), 7.73 (d, J = 7.3 Hz, 1H), 7.53 (s, 1H), 6.94 (s, 1H), 3.98 (q J = 7.3 Hz, 2H), 2.54 (s, 3H), 1.32 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 504.80 (MH) + 。

[0426] Example-5: Synthesis of 6-(3-(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 57)

[0427] To a stirred solution of a mixture of tetrahydrofuran (3 mL) and water (3 mL) containing 6-(3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (150 mg, 0.42 mmol) and (4-(trifluoromethoxy)phenyl)boronic acid (87 mg, 0.42 mmol), sodium carbonate (89 mg, 0.84 mmol) and tetrakis(triphenylphosphine)palladium(0) (14.59 mg, 0.01 mmol) were added. The reaction mixture was thoroughly deoxygenated by applying a vacuum / nitrogen cycle three times and heated at 85 °C for 3 hours. After completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (100 mL). The ethyl acetate layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product, which was purified by silica gel column chromatography using hexane containing 20% ethyl acetate as the eluent to give 6-(3-(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (78 mg, 0.15 mmol, 36% yield) as a solid. 1 1H-NMR (400 MHz, DMSO-d6) δ 9.64 (q, J = 1.0 Hz, 1H), 8.97 (d, J = 2.1 Hz, 1H), 8.61 (d, J = 8.6 Hz, 1H), 8.44 (d, J = 8.6 Hz, 1H), 8.37 (dt, J = 9.6, 2.4 Hz, 2H), 7.54 (dd, J = 8.9, 0.9 Hz, 2H), 7.42 (s, 1H), 3.31 (q, J = 7.3 Hz, 2H), 1.09 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 517.00 (MH) + 。

[0428] Example - 6: Synthesis of 6-chloro-3-(ethylthio)-2-(tributylstannyl)pyridine (Intermediate 3) of Example - 4

[0429] Step-1: 6-Chloro-3-(ethylthio)-2-(tributylstannyl)pyridine

[0430] To a stirred solution of anhydrous toluene (160 mL) containing 2-bromo-6-chloro-3-(ethylthio)pyridine (8.0 g, 31.7 mmol), a solution of n-butyllithium (2.5 M n-hexane solution) (20.60 mL, 41.2 mmol) was added dropwise at -78 °C over 15 minutes. The reaction mixture was stirred for 1 hour while maintaining the temperature at -78 °C until the solution turned dark red. Tri-n-butylchlorotin (11.20 mL, 41.2 mmol) was added dropwise to the above reaction mixture, and the reaction was stirred for 12 hours while warming to 25 °C. After completion of the reaction, the reaction mixture was cooled to 0 °C and quenched by dropwise addition of water (200 mL). The reaction mixture was extracted with ethyl acetate (2 x 200 mL). The combined ethyl acetate layers were washed with brine (100 mL) and water (100 mL), dried over anhydrous sodium sulfate, and concentrated to give crude 6-chloro-3-(ethylthio)-2-(tributylstannyl)pyridine (10 g, 21.61 mmol, 68% yield), which was used without further purification in the next step. ESI MS (m / z) 462.70.80, 463.80 [(MH) + Cl 35, 37 .

[0431] Example-7: Synthesis of 5-(3-(ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 4).

[0432] Step-1: 5-(6-Chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0433] A stirred solution of 6-chloro-3-(ethylsulfonyl)-2-(tributylstannyl)pyridine (5.0 g, 10.11 mmol) and 5-bromo-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (2.42 g, 9.0 mmol) in anhydrous tetrahydrofuran (50 mL) was thoroughly deoxygenated by applying a vacuum / nitrogen cycle three times, and then tetrakis(triphenylphosphine)palladium(0) (1.17 g, 1.01 mmol) and copper(I) bromide (290 mg, 2.02 mmol) were added. The reaction mixture was heated at 70 °C for 1 hour. After completion of the reaction, the reaction mixture was cooled to 25 °C, diluted with water (50 mL), and extracted with ethyl acetate (2 x 100 mL). The combined ethyl acetate layers were separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography using hexane containing 25% ethyl acetate as the eluent to give 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (2.0 g, 5.12 mmol, 51% yield) as a solid. 1 1H-NMR (400 MHz, DMSO-d6) δ 9.48 (dd, J = 7.3, 1.0 Hz, 1H), 8.53 (d, J = 8.6 Hz, 1H), 8.03 (d, J = 8.6 Hz, 1H), 7.67 (d, J = 7.5 Hz, 1H), 7.51 (s, 1H), 3.87 (q, J = 7.4 Hz, 2H), 1.28 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 390.85, 392.85 [(MH)+ + Br 79, 81 .

[0434] Step - 2: 5-(3-(Ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0435] A stirred solution of anhydrous dimethyl sulfoxide (2 mL) containing 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (230 mg, 0.60 mmol) and 3-(trifluoromethyl)-1H-1,2,4-triazole (80 mg, 0.60 mmol) was added with potassium carbonate (120 mg, 0.90 mmol). The reaction mixture was stirred at 100 °C for 2 hours. After completion of the reaction, the reaction mixture was diluted with ice water (60 mL) and extracted with ethyl acetate (2 x 30 mL). The combined ethyl acetate layers were washed with brine (50 mL) and water (50 mL). Dried over anhydrous sodium sulfate and concentrated to obtain a crude product, which was purified by column chromatography on silica gel using hexane containing 40% ethyl acetate as the eluent to give 5-(3-(ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (0.101 g, 0.20 mmol, 34% yield). 1 1H-NMR (400 MHz, DMSO-d6) δ 9.93 (d, J = 1.0 Hz, 1H), 9.58 (dd, J = 7.3, 0.7 Hz, 1H), 8.80 (d, J = 8.6 Hz, 1H), 8.34 (d, J = 8.6 Hz, 1H), 7.95 (d, J = 7.3 Hz, 1H), 7.57 (s, 1H), 3.97-4.06 (m, 2H), 1.33 (t, J = 7.5 Hz, 3H); ESI-MS (m / z) 492 (MH) + 。

[0436] Example - 8: Synthesis of 5-(6-(4-chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 20)

[0437] 5-(6-(4-Chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0438] To a stirred solution of 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (150 mg, 0.38 mmol) and (4-chlorophenyl)boronic acid (78 mg, 0.38 mmol) in a mixed solvent of 1,4-dioxane (4 mL) and water (1 mL), sodium carbonate (102 mg, 0.96 mmol) and tetrakis(triphenylphosphine)palladium(0) (22.18 mg, 0.02 mmol) were added. The reaction mixture was thoroughly deoxygenated by applying a vacuum / nitrogen cycle three times and heated at 100 °C for 2 hours. After completion of the reaction, the reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (80 mL). The ethyl acetate layer was separated, dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography using hexane containing 20% ethyl acetate as an eluent to give 5-(6-(4-chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (111 mg, 0.238 mmol, 62% yield) as a solid. 1 1H-NMR (400 MHz, DMSO-d6) δ 9.47 (dd, J = 7.3, 1.0 Hz, 1H), 8.55 (d, J = 8.6 Hz, 1H), 8.44 (d, J = 8.3 Hz, 1H), 8.26 - 8.29 (m, 2H), 7.82 (d, J = 7.1 Hz, 1H), 7.64 (dd, J = 6.8, 2.0 Hz, 2H), 7.48 (s, 1H), 3.90 (q, J = 7.4 Hz, 2H), 1.21 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 466.85, 468.85 [(MH)+ + Cl 35, 37 .

[0439] Example - 9: Synthesis of 6 - chloro - 3 - (ethylsulfonyl) - 2 - (tributylstannyl)pyridine (Intermediate - 5) of Example - 7

[0440] Step - 1: 6 - chloro - 3 - (ethylsulfonyl) - 2 - (tributylstannyl)pyridine

[0441] To a stirred solution of anhydrous toluene (160 mL) containing 2 - bromo - 6 - chloro - 3 - (ethylsulfonyl)pyridine (2.0 g, 7.03 mmol) was added dropwise n - butyllithium (2.5 M n - hexane solution) (5.30 mL, 10.54 mmol) at - 78 °C over 15 minutes. The reaction mixture was stirred for 1 hour while maintaining at - 78 °C until the solution turned dark red. Tri - n - butylchlorotin (3.80 mL, 14.06 mmol) was added dropwise to the above reaction mixture, and the reaction was stirred for 12 hours while warming to 25 °C. After completion of the reaction, the reaction mixture was cooled to 0 °C and quenched by dropwise addition of water (50 mL). The reaction mixture was extracted with ethyl acetate (2 x 50 mL). The combined ethyl acetate layers were washed with brine (100 mL) and water (100 mL), dried over anhydrous sodium sulfate, concentrated to obtain a crude product, which was purified by silica gel column chromatography using hexane containing 20% ethyl acetate as the eluent to give 6 - chloro - 3 - (ethylsulfonyl) - 2 - (tributylstannyl)pyridine (1.3 g, 2.63 mmol, 37% yield). 1H - NMR (400 MHz, DMSO - d6) δ 8.27 (dd, J = 8.2, 1.3 Hz, 1H), 7.66 (dd, J = 8.2, 1.3 Hz, 1H), 3.36 (q, J = 7.4 Hz, 2H), 1.48 - 1.58 (m, 6H), 1.12 - 1.33 (m, 15H), 0.81 - 0.90 (m, 9H); ESI - MS (m / z) 493.90, 495.90 [(MH)+Cl35, 37].

[0442] Example - 10: Synthesis of 5-(5-(Ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 62)

[0443] Step - 1: 5-(6-Chloro-5-(ethylthio)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0444] A stirred solution of anhydrous tetrahydrofuran (100 mL) containing 5-bromo-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (5.0 g, 18.80 mmol) and 2-chloro-3-(ethylthio)-5-(tributylstannyl)pyridine (12.20 g, 26.0 mmol) was thoroughly deoxygenated by subjecting it to three cycles of vacuum / nitrogen. Then, the reaction was carried out by adding tetrakis(triphenylphosphine)palladium(0) (2.17 g, 1.88 mmol) and copper(I) bromide (0.54 g, 3.76 mmol). The reaction mixture was heated at 70 °C for 2 hours. After completion of the reaction, the reaction mixture was cooled to 25 °C, diluted with water (100 mL), and extracted with ethyl acetate (2 x 100 mL). The combined ethyl acetate layers were separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography using hexane containing 15% ethyl acetate as the eluent to give 5-(6-chloro-5-(ethylthio)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (3.0 g, 8.36 mmol, 45% yield) as a solid phase. 1H-NMR (400 MHz, DMSO-d6) δ 9.45 (dd, J = 7.5, 0.9 Hz, 1H), 8.97 (d, J = 2.2 Hz, 1H), 8.40 (d, J = 2.2 Hz, 1H), 8.07 (d, J = 7.6 Hz, 1H), 7.38 (s, 1H), 3.22 (q, J = 7.3 Hz, 2H), 1.35 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 358.95, 360.70 [(MH) + Cl 35, 37 .

[0445] Step-2: 5-(6-Chloro-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0446] To a stirred solution of 5-(6-chloro-5-(ethylthio)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (3.0 g, 8.36 mmol) in dichloromethane (60 mL) was added m-chloroperbenzoic acid (4.80 g, 16.72 mmol) portion wise at 0 - 5 °C. After the reaction mixture was stirred at 25 °C for 5 h until the reaction was complete, the reaction mixture was cooled to 0 °C, quenched by dropwise addition of 2N sodium hydroxide solution (50 mL), and extracted with dichloromethane (2 x 50 mL). The combined dichloromethane layers were dried over anhydrous sodium sulfate, concentrated to give the crude product, which was purified by silica gel column chromatography using hexane containing 30% ethyl acetate as the eluent to give 5-(6-chloro-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (2.5 g, 6.40 mmol, 77% yield) as a solid phase. 1H-NMR (400 MHz, DMSO-d6) δ 9.56 (d, J = 2.1 Hz, 1H), 9.50 (dd, J = 7.5, 0.8 Hz, 1H), 9.11 (d, J = 2.4 Hz, 1H), 8.14 (d, J = 7.6 Hz, 1H), 7.49 (s, 1H), 3.65 (q, J = 7.4 Hz, 2H), 1.21 (t, J = 7.5 Hz, 3H) ); ESI MS (m / z) 390.95,392.95 [(MH) + Cl 35, 37 .

[0447] Step-3: 5-(5-(Ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0448] To a stirred solution of anhydrous N,N-dimethylformamide (3 mL) containing 5-(6-chloro-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (200 mg, 0.51 mmol) and 5-methyl-3-(trifluoromethyl)-1H-pyrazole (77 mg, 0.51 mmol) was added potassium carbonate (141 mg, 1.02 mmol). The reaction mixture was stirred at 25 °C for 12 h. After completion of the reaction, the reaction mixture was diluted with ice water (30 mL) and extracted with ethyl acetate (2 x 30 mL). The combined ethyl acetate layers were washed with brine (50 mL) and water (50 mL). Dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product, which was purified by column chromatography on silica gel using hexane containing 40% ethyl acetate as the eluent to give 5-(5-(ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (105 mg, 0.208 mmol, 41% yield). 11H NMR (400 MHz, DMSO-d6) δ 9.78 (d, J = 2.2 Hz, 1 H), 9.57 (dd, J = 7.3, 1.0 Hz, 1 H), 9.29 (d, J = 2.2 Hz, 1 H), 8.25 (d, J = 7.6 Hz, 1 H), 7.55 (s, 1 H), 6.91 (s, 1 H), 3.76 (q, J = 7.3 Hz, 2 H), 2.36 (d, J = 0.7 Hz, 3 H), 1.27 (t, J = 7.3 Hz, 3 H); ESI MS (m / z) 504.75 (MH)+。

[0449] Example - 11: Synthesis of 2-chloro-3-(ethylthio)-5-(tributylstannyl)pyridine (Intermediate - 2) in Example - 10

[0450] Step - 1: 2-chloro-3-(ethylthio)-5-(tributylstannyl)pyridine

[0451] To a stirred solution of anhydrous toluene (40 mL) containing 5-bromo-2-chloro-3-(ethylthio)pyridine (2.0 g, 7.92 mmol) was added n-butyllithium (1.6 M n-hexane solution) (6.0 mL, 9.50 mmol) dropwise over 15 minutes at -78 °C. The reaction mixture was stirred for 1 hour while maintaining at -78 °C until the solution turned dark red. Tri-n-butylchlorotin (2.60 mL, 9.50 mmol) was added dropwise to the above reaction mixture, and the reaction was stirred for 12 hours while warming to 25 °C. After completion of the reaction, the reaction mixture was cooled to 0 °C and quenched by dropwise addition of water (50 mL). The reaction mixture was extracted with ethyl acetate (2 x 50 mL). The combined ethyl acetate layers were washed with brine (100 mL) and water (100 mL), dried over anhydrous sodium sulfate, concentrated to obtain a crude product, which was purified by silica gel column chromatography using hexane containing 20% ethyl acetate as the eluent to obtain crude 2-chloro-3-(ethylthio)-5-(tributylstannyl)pyridine (1.5 g, 3.24 mmol, 41% yield), which was used without further purification in the next step.

[0452] Example - 12: Synthesis of 6-(3-(ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine: (Compound 60)

[0453] Step - 1: 6-Bromo-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine

[0454] A stirred solution of ethanol (30 mL) containing 3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (1 g, 6.58 mmol) was partially added with 2-bromomalonaldehyde (1.0 g, 6.58 mmol) at 25 °C over 15 minutes, and then concentrated hydrochloric acid (0.8 mL) was added dropwise. The reaction mixture was stirred at 25 °C for 12 hours. After completion of the reaction, the reaction solution was concentrated to half its volume. The reaction mixture was cooled to 0 °C and treated with a saturated solution of sodium hydrogen carbonate (50 mL) with stirring for 30 minutes. The precipitate of 6-bromo-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (1.4 g, 5.24 mmol, 80% yield) was collected by filtration, washed with water (20 mL), and dried under vacuum. 1 1H-NMR (400 MHz, DMSO-d6) δ 10.06 (d, J = 2.4 Hz, 1H), 9.18 (d, J = 2.4 Hz, 1H).

[0455] Step - 2: 6-(6-Chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine

[0456] The title compound 6-(6-chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (105 mg, 0.29 mmol, 37% yield) was prepared from 6-bromo-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (210 mg, 0.78 mmol) and 6-chloro-3-(ethylthio)-2-(tributylstannyl)pyridine (437 mg, 0.94 mmol) according to the reaction conditions described in Step 2 of Compound 9 (Example - 4). 1H-NMR (400 MHz, DMSO-d6) δ 9.88 (d, J = 2.4 Hz, 1H), 9.29 (d, J = 2.4 Hz, 1H), 8.12 (d, J = 8.6 Hz, 1H), 7.67 (d, J = 8.3 Hz, 1H), 3.01 (q, J = 7.2 Hz, 2H), 1.16 (t, J = 7.3 Hz, 3H), ESI MS (m / z) 359.80 (MH) + 。

[0457] Step-3: 6-(6-Chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine

[0458] The title compound 6-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (800 mg, 2.0 mmol, yield 37%) was prepared from 6-(6-chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (2.0 g, 5.56 mmol) according to the reaction conditions described in Step 3 of Compound 9 (Example 4). 1 H-NMR (400 MHz, DMSO-d6) δ 9.84-9.85 (m, 1H), 9.22-9.23 (m, 1H), 8.54-8.57 (m, 1H), 8.01-8.04 (m, 1H), 3.25 (q, J = 7.3 Hz, 2H), 1.04 (t, J = 7.3 Hz, 3H), ESI MS (m / z) 391.80 (MH) + 。

[0459] Step-4: 6-(3-(Ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine

[0460] The title compound 6-(3-(ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (95 mg, 0.224 mmol, yield 35%) was prepared from 6-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (250 mg, 0.64 mmol) and 1H-1,2,4-triazole (66.1 mg, 1.0 mmol) according to the reaction conditions described in Step 4 of Compound 9 (Example 4). 1 H-NMR (400 MHz, DMSO-d6) δ 9.95 (d, J = 2.1 Hz, 1H), 9.56 (s, 1H), 9.37 (d, J = 2.4 Hz, 1H), 8.78 (d, J = 8.6 Hz, 1H), 8.45 (s, 1H), 8.24 (d, J = 8.6 Hz, 1H), 3.28 (q, J = 7.3 Hz, 2H), 1.06 (t, J = 7.3 Hz, 3H), ESI MS (m / z) 424.95 (MH) + 。

[0461] Example 13: Synthesis of 6-(3-(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 43)

[0462] The title compound 6-(3-(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (120 mg, 0.23 mmol, yield 45%) was prepared from 6-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (200 mg, 0.51 mmol) and (4-(trifluoromethoxy)phenyl)boronic acid (126 mg, 0.61 mmol) according to the reaction conditions described in Step 1 of Compound 33 (Example 8). 1 1H-NMR (400 MHz, DMSO-d6) δ 9.94 (d, J = 2.4 Hz, 1H), 9.33 (d, J = 2.2 Hz, 1H), 8.62 (d, J = 8.6 Hz, 1H), 8.46 (d, J = 8.6 Hz, 1H), 8.37 (dd, J = 6.8, 2.2 Hz, 2H), 7.56 (d, J = 8.1 Hz, 2H), 3.28 (q, J = 7.3 Hz, 2H), 1.07 (t, J = 7.3 Hz, 3H), ESI MS (m / z) 517.90 (MH) + .

[0463] Example - 14: Synthesis of 6-(5-(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 68)

[0464] Step - 1: 6-(6-chloro-5-(ethylthio)pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine

[0465] The title compound 6-(6-chloro-5-(ethylthio)pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (150 mg, 0.42 mmol, 32% yield) was prepared from 6-bromo-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (210 mg, 0.79 mmol) and 2-chloro-3-(ethylthio)-5-(tributylstannyl)pyridine (910 mg, 1.96 mmol) according to the reaction conditions described in Step 2 of Compound 9 (Example 4). 1 1H-NMR (400 MHz, DMSO-d6) δ 9.88 (d, J = 2.4 Hz, 1H), 9.29 (d, J = 2.4 Hz, 1H), 8.12 (d, J = 8.6 Hz, 1H), 7.67 (d, J = 8.3 Hz, 1H), 3.01 (q, J = 7.2 Hz, 2H), 1.16 (t, J = 7.3 Hz, 3H), ESI MS (m / z) 359.80 (MH) + 。

[0466] Step-2: 6-(6-chloro-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine

[0467] The title compound 6-(6-chloro-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (200 mg, 0.51 mmol, 24% yield) was prepared from 6-(6-chloro-5-(ethylthio)pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (780 mg, 2.17 mmol) according to the reaction conditions described in Step 3 of Compound 9 (Example 4). 1H-NMR (400 MHz, DMSO-d6) δ 9.84-9.85 (m, 1H), 9.22-9.23 (m, 1H), 8.54-8.57 (m, 1H), 8.01-8.04 (m, 1H), 3.25 (q, J = 7.3 Hz, 2H), 1.04 (t, J = 7.3 Hz, 3H).

[0468] Step - 3: Synthesis of 6-(5-(Ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine

[0469] The title compound 6-(5-(Ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (129 mg, 0.25 mmol, yield 39%) was prepared from 6-(6-chloro-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (250 mg, 0.64 mmol) and (4-(trifluoromethoxy)phenyl)boronic acid (158 mg, 0.77 mmol) according to the reaction conditions described in Step 1 of Compound 33 (Example 8). 1 H-NMR (400 MHz, DMSO-d6) δ 10.25 (d, J = 2.4 Hz, 1H), 9.63 (d, J = 2.4 Hz, 1H), 9.44 (d, J = 2.1 Hz, 1H), 8.89 (d, J = 2.1 Hz, 1H), 7.72 (dt, J = 9.3, 2.4 Hz, 2H), 7.50 (d, J = 7.9 Hz, 2H), 3.18 (q, J = 7.4 Hz, 2H), 1.07 (t, J = 7.3 Hz, 3H), ESI MS (m / z) 517.75 (MH) + .

[0470] Example - 15: Synthesis of 5-(3-(Ethylsulfonyl)-5-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 158)

[0471] a) Step - 1: 2-(Trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one

[0472] A solution of ethyl (E)-3-ethoxyacrylate (28.7 ml, 197.00 mmol) in anhydrous N,N-dimethylformamide (5 mL) was added dropwise to a stirred solution of 3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (15 g, 99.0 mmol) in anhydrous N,N-dimethylformamide (100 mL) at room temperature over 15 minutes, and then potassium carbonate (34.1 g, 247.0 mmol) was added. The reaction was heated at 100 °C for 16 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and diluted with water (100 mL). The reaction mixture was acidified by dropping acetic acid (15 mL) at 0 °C, and then stirred at room temperature for another 2 hours. The resulting mixture was extracted with ethyl acetate (2 x 200 mL), and the combined ethyl acetate layers were washed with water (100 mL) and brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product, which was purified by silica gel on a CombiFlash system using hexane containing 60% ethyl acetate as the eluent to obtain 2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one (10 g, 49.0 mmol, yield 49.70%). 1 HNMR (400 MHz, DMSO-d6) δ 8.66 (d, J = 7.9 Hz, 1H), 6.32 (d, J = 7.6 Hz, 1H); ESI MS (m / z) 204.90 (MH) + 。

[0473] b) Step - 2: 5 - Bromo - 2 - (trifluoromethyl) - [1,2,4]triazolo[1,5 - a]pyrimidine

[0474] Phosphorus(V) oxybromide (42.1 g, 147.0 mmol) was added to a stirred solution of 2 - (trifluoromethyl) - [1,2,4]triazolo[1,5 - a]pyrimidin - 5(4H) - one (20 g, 98.0 mmol) in 1,2 - dichloroethane (300 mL) at room temperature. The reaction mixture was heated at 100 °C for 5 h. After completion of the reaction, the reaction mixture was cooled to room temperature and diluted with water (200 mL). The aqueous layer was extracted with ethyl acetate (2 x 200 mL), and the combined ethyl acetate layers were washed with saturated sodium hydrogen carbonate solution (200 mL), water (100 mL), and brine (100 mL). Dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified using a CombiFlash system with silica gel, using hexane containing 10% ethyl acetate as the eluent, to give 5 - bromo - 2 - (trifluoromethyl) - [1,2,4]triazolo[1,5 - a]pyrimidine (12 g, 44.90 mmol, 45.9% yield). 1 HNMR (400 MHz, DMSO - d6) δ 9.49 (q, J = 2.4 Hz, 1H), 7.85 (d, J = 7.1 Hz, 1H).

[0475] c) Step - 3: Synthesis of 5 - (5 - bromo - 3 - (ethylthio)pyridin - 2 - yl) - 2 - (trifluoromethyl) - [1,2,4]triazolo[1,5 - a]pyrimidine (Compound 90)

[0476] The title compound 5-(5-bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (650 mg, 1.61 mmol, 33% yield) was prepared from 5-bromo-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (1.3 g, 4.87 mmol) and 5-bromo-3-(ethylthio)-2-(tributylstannyl)pyridine (3.70 g, 7.30 mmol) according to the reaction conditions described in Step 3 for Compound 38 (Example 1). 1 1H-NMR (400 MHz, DMSO-d6) δ 9.31 (dd, J = 7.3, 0.9 Hz, 1H), 8.63 (d, J = 1.8 Hz, 1H), 8.15 (d, J = 1.8 Hz, 1H), 7.87 (d, J = 7.3 Hz, 1H), 7.37 (s, 1H), 3.05 (q, J = 7.3 Hz, 2H), 1.23 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 404.70, 405.70 [(MH) + Br 79, 81 .

[0477] d) Step - 4: Synthesis of 5-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 99)

[0478] The title compound 5-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (420 mg, 0.96 mmol, 48. 6% yield) was prepared from 5-(5-bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (800 mg, 1.98 mmol) according to the reaction conditions described in Step 4 of Compound 38 (Example 1). 11H-NMR (400 MHz, DMSO-d6) δ 9.45 (dd, J = 7.3, 0.9 Hz, 1H), 9.22 (d, J = 2.1 Hz, 1H), 8.65 (d, J = 2.1 Hz, 1H), 7.65 (d, J = 7.3 Hz, 1H), 7.49 (s, 1H), 3.93 (q, J = 7.4 Hz, 2H), 1.29 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 434.65, 435.65 [(MH) + Br 79, 81 .

[0479] e) Step-5: Synthesis of 5-(3-(ethylsulfonyl)-5-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 158)

[0480] To a stirred solution of toluene (10 mL) containing 5-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (300 mg, 0.69 mmol) and 3-(trifluoromethyl)-1H-1,2,4-triazole (337 mg, 2.75 mmol), potassium phosphate tribasic (365 mg, 1.71 mmol) and 2-di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl (146 mg, 0.034 mmol) were added. The reaction mixture was thoroughly deoxygenated by applying three cycles of vacuum / nitrogen, and tris(dibenzylideneacetone)dipalladium(0) (315 mg, 0.035 mmol) was added. The reaction mixture was heated at 110 °C for 12 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (20 mL) and water (10 mL). The ethyl acetate layer was separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the crude product, which was purified by silica gel on a CombiFlash system using hexane containing 60% ethyl acetate as the eluent to give 5-(3-(ethylsulfonyl)-5-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (68 mg, 0.14 mmol, yield 20.08%) as a solid. 1 1H-NMR (400 MHz, DMSO-d6) δ 9.92-9.78 (m, 2H), 9.64 (d, J = 2.4 Hz, 1H), 8.94 (d, J = 2.1 Hz, 1H), 8.04 (d, J = 7.0 Hz, 1H), 4.01 (q, J = 7.3 Hz, 2H), 1.34 (t, J = 7.5 Hz, 3H) ESI MS (m / z) 493.00 (MH) + 。

[0481] Example - 16: Synthesis of 5-(6-Cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 180)

[0482] a) Step - 1: Synthesis of 5-(6-Chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 165)

[0483] The title compound 5-(6-Chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidine (450 mg, 1.25 mmol, 47.7% yield) was prepared from 5-bromo-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (700.0 mg, 2.62 mmol) and 6-chloro-3-(ethylthio)-2-(tributylstannyl)pyridine (1820 mg, 3.93 mmol) according to the reaction conditions described in Step 2 of Compound 45 (Example 4). 1 H-NMR (400 MHz, DMSO-d6) δ 9.59 (d, J = 7.1 Hz, 1H), 8.19 - 8.15 (m, 1H), 8.10 (d, J = 8.8 Hz, 1H), 7.70 (d, J = 8.6 Hz, 1H), 3.05 (q, J = 7.3 Hz, 2H), 1.27 - 1.22 (m, 3H) ESI MS (m / z) 360, 362 [(MH) + Cl 35, 37 .

[0484] a) Step - 4: Synthesis of 5-(6-Chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 169)

[0485] The title compound 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (140 mg, 0.36 mmol, 32.1% yield) was prepared from 5-(6-chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (400 mg, 1.11 mmol) according to the reaction conditions described in Step 3 of Compound 45 (Example 4). 1 1H-NMR (400 MHz, DMSO-d6) δ 9.77 (d, J = 7.1 Hz, 1H), 8.54 (d, J = 8.3 Hz, 1H), 8.06 (d, J = 8.6 Hz, 1H), 7.97 (d, J = 7.1 Hz, 1H), 3.86 (q, J = 7.4 Hz, 2H), 1.27 (t, J = 7.5 Hz, 3H) ESI MS (m / z) 392,394 [(MH)+ + Cl 35, 37 .

[0486] b) Step - 3: Synthesis of 5-(6-cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 180)

[0487] To a stirred solution of a mixture of dioxane (8 mL) and water (2 mL) containing 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (250 mg, 0.64 mmol) and cyclopropylboronic acid (219 mg, 2.55 mmol), potassium phosphate tribasic (406 mg, 1.92 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (52.1 mg, 0.06 mmol) were added sequentially. The reaction mixture was degassed thoroughly by subjecting it to three cycles of vacuum / nitrogen and heated at 110 °C for 3 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (20 mL) and water (10 mL). The ethyl acetate layer was separated, filtered, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product, which was purified by a CombiFlash system using silica gel with hexane containing 25% ethyl acetate as the eluent to give 5-(6-cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidine (74 mg, 0.19 mmol, 29.2% yield) as a solid. 1 1H-NMR (400 MHz, DMSO-d6) δ 9.71 (d, J = 7.1 Hz, 1H), 8.32 (d, J = 8.3 Hz, 1H), 7.94 (d, J = 7.1 Hz, 1H), 7.80 (d, J = 8.6 Hz, 1H), 3.83 (q, J = 7.4 Hz, 2H), 2.41-2.34 (m, 1H), 1.25 (t, J = 7.5 Hz, 3H), 1.18-1.09 (m, 4H) ESI MS (m / z) 397.55 (MH) + 。

[0488] Example - 17: Synthesis of 5-(3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 152)

[0489] Step-1: Synthesis of 5-(3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 153)

[0490] 3-(Ethylthio)-2-(tributylstannyl)pyridine: The title compound 3-(ethylthio)-2-(tributylstannyl)pyridine (2.1 g, 4.90 mmol, 71.3% yield) was prepared from 5-bromo-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (1.0 g, 3.75 mmol) as described in Example-9. The crude product was used directly in the next step without purification.

[0491] The title compound 5-(3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (450 mg, 1.38 mmol, 36.9% yield) was prepared from 5-bromo-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (1.0 gram, 3.75 mmol) and 3-(ethylthio)-2-(tributylstannyl)pyridine (2.406 g, 5.62 mmol) according to the reaction conditions described in Step 2 of Compound 45 (Example 4). 1 H-NMR (400 MHz, DMSO-d6) δ 9.57 (d, J = 7.3 Hz, 1H), 8.57 (dd, J = 4.4, 1.4 Hz, 1H), 8.24 (d, J = 7.3 Hz, 1H), 8.05 (dd, J = 8.3, 1.2 Hz, 1H), 7.58 (q, J = 4.3 Hz, 1H), 3.03 (q, J = 7.3 Hz, 2H), 1.25 (t, J = 7.3 Hz, 3H) ESI MS (m / z) 325.90 (MH) + .

[0492] Step-2: Synthesis of 5-(3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 152)

[0493] The title compound 5-(3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (180 mg, 0.50 mmol, 41.0%) was prepared from 5-(3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (400 mg, 1.23 mmol) according to the reaction conditions described in Step 3 of Compound 45 (Example 4). 1 H-NMR (400 MHz, DMSO-d6) δ 9.92-9.78 (m, 2H), 9.64 (d, J = 2.4 Hz, 1H), 8.94 (d, J = 2.1 Hz, 1H), 8.04 (d, J = 7.0 Hz, 1H), 4.01 (q, J = 7.3 Hz, 2H), 1.34 (t, J = 7.5 Hz, 3H) ESI MS (m / z) 493 (MH) + 。

[0494] Example - 18: Synthesis of 5-(5-(cyclopropylmethoxy)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 161).

[0495] Step - 1: Synthesis of 5-(3-(ethylsulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine

[0496] 5-(5-Bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Step 4; Example 15) (2 g, 4.58 mmol) and bis(pinacolato)diboron (2.33 g, 9.17 mmol) were added to a stirred solution of dioxane (8 mL). Potassium acetate (0.90 g, 9.17 mmol) was added, followed by [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.19 g, 0.23 mmol) under a nitrogen atmosphere. The reaction mixture was degassed thoroughly by subjecting it to three vacuum / nitrogen cycles and heated at 90 °C for 1 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (50 mL) and water (25 mL). The aqueous layer was extracted with ethyl acetate (2 x 50 mL), and the combined ethyl acetate layers were dried over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the crude product was obtained, which was purified by silica gel on a CombiFlash system using hexane containing 30% ethyl acetate as the eluent to give 5-(3-(ethylsulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (1.2 g, 2.49 mmol, 54.2% yield) as a solid. ESI MS (m / z) 481.75 (MH) - 。

[0497] Step-2: Synthesis of 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-ol (Compound 109)

[0498] A solution of 5-(3-(ethylsulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (1.5 g, 3.10 mmol) in tetrahydrofuran (50 mL) was added dropwise with hydrogen peroxide (7.93 ml, 78 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (50 mL) and water (25 mL). The aqueous layer was extracted with ethyl acetate (2 x 50 mL), and the combined ethyl acetate layers were dried over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, a crude product was obtained, which was purified by silica gel on a CombiFlash system using hexane containing 50% ethyl acetate as the eluent to give 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-ol (540 mg, 1.45 mmol, 46.6% yield) as a solid. 1 1H-NMR (400 MHz, DMSO-d6) δ 11.47 (s, 1H), 9.66 (d, J = 7.1 Hz, 1H), 8.57 (d, J = 2.4 Hz, 1H), 7.92 (d, J = 7.1 Hz, 1H), 7.85 (d, J = 2.4 Hz, 1H), 3.98 (q, J = 7.4 Hz, 2H), 1.29 (t, J = 7.5 Hz, 3H) ESI MS (m / z) 373.85 (MH) + .

[0499] Step - 3: Synthesis of 5-(5-(cyclopropylmethoxy)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 161)

[0500] A stirred solution of anhydrous N,N-dimethylformamide (2 mL) containing 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-ol (200 mg, 0.54 mmol) and cyclopropylmethyl bromide (87 mg, 0.64 mmol) was added with cesium carbonate (349 mg, 1.07 mmol). The reaction mixture was stirred at room temperature for 12 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (20 mL) and water (25 mL). The aqueous layer was extracted with ethyl acetate (2 x 20 mL), the combined ethyl acetate layers were separated and dried over anhydrous sodium sulfate. After filtration, it was concentrated under reduced pressure to obtain a crude product, which was purified by silica gel on a CombiFlash system using hexane containing 20% ethyl acetate as an eluent to give 5-(5-(cyclopropylmethoxy)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (56 mg, 0.13 mmol, 24.46% yield). 1 1H-NMR (400 MHz, DMSO-d6) δ 9.68 (d, J = 7.1 Hz, 1H), 8.78 (d, J = 2.7 Hz, 1H), 7.94-7.92 (m, 2H), 4.15 (d, J = 7.1 Hz, 2H), 3.97 (q, J = 7.4 Hz, 2H), 1.30 (t, J = 7.5 Hz, 4H), 0.65-0.61 (m, 2H), 0.43-0.40 (m, 2H) ESI MS (m / z) 428.15 (MH) + 。

[0501] Example - 19: Synthesis of 2-(5-(3,5-difluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine (Compound 122).

[0502] Step - 1: Synthesis of 5-bromo-3-(ethylthio)picolinitrile

[0503] To a stirred solution of 5-bromo-3-fluoropicolinonitrile (10 g, 49.8 mmol) in tetrahydrofuran (100 mL), sodium hydride (1.2 g, 49.8 mmol) was added at -15 °C under a nitrogen atmosphere. Next, ethanethiol (3.1 g, 49.8 mmol) was added dropwise to the reaction mixture at the same temperature. The reaction mixture was stirred at room temperature for 16 h. After completion of the reaction, the reaction mixture was quenched with ice water (500 mL) and extracted with ethyl acetate (2 x 500 mL). The combined ethyl acetate layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product, which was purified by silica gel on a CombiFlash system using hexane containing 10% ethyl acetate as the eluent to give 5-bromo-3-(ethylthio)picolinonitrile (12 g, 49.4 mmol, 99% yield). 1 1H-NMR (400 MHz, CDCl3) δ 8.49 (d, J = 2.1 Hz, 1H), 7.84 - 7.82 (m, 1H), 3.07 (q, J = 7.4 Hz, 2H), 1.41 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 242.95(MH)+.

[0504] Step-2: Synthesis of 5-bromo-3-(ethylthio)picolinimidamide hydrochloride

[0505] To a stirred solution of 5-bromo-3-(ethylthio)picolinonitrile (10 g, 41.1 mmol) in methanol (500 mL), sodium methoxide (2.22 g, 41.1 mmol) was added at 0 °C under nitrogen. Next, ammonium chloride (2.20 g, 41.1 mmol) was added to the reaction mixture. After stirring at room temperature for 1 h, the mixture was stirred at reflux for 6 h. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and diluted with ethyl acetate. The resulting white solid was filtered and dried under reduced pressure to give 5-bromo-3-(ethylthio)picolinimidamide hydrochloride (5.0 g, 16.86 mmol, 41.0% yield). 1H-NMR (400 MHz, DMSO-d6) δ 9.56 (s, 3H), 8.66 (d, J = 2.0 Hz, 1H), 8.35-8.34 (m, 1H), 3.16-3.09 (m, 2H), 1.22 (t, J = 7.2 Hz, 3H); ESI MS (m / z) 260(MH)+。

[0506] Step-3: Synthesis of 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-5-nitropyrimidin-4(3H)-one

[0507] To a stirred solution of methanol (50 mL) containing 5-bromo-3-(ethylthio)picolinimidamide hydrochloride (5 g, 16.9 mmol) and ethyl (E)-3-(dimethylamino)-2-nitroacrylate (3.2 g, 16.9 mmol) was added triethylamine (2.4 mL, 16.9 mmol). The reaction mixture was heated at 70 °C for 1 h. The reaction mixture was cooled to room temperature and concentrated to give the crude product, which was purified by a CombiFlash system using silica gel with dichloromethane containing 10% methanol as the eluent to give 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-5-nitropyrimidin-4(3H)-one (2.5 g, 7.0 mmol, 41.5% yield). 1 H-NMR (400 MHz, DMSO-d6) δ 13.61 (s, 1H), 8.91 (s, 1H), 8.62 (d, J = 1.8 Hz, 1H), 8.17 (d, J = 1.8 Hz, 1H), 3.06 (q, J = 7.3 Hz, 2H), 1.24 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 358.8(MH)+。

[0508] Step-4: Synthesis of 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-4-chloro-5-nitropyrimidine

[0509] To 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-5-nitropyrimidin-4(3H)-one (7.5 g, 21.0 mmol) was added phosphorus oxychloride (POCl3) (39.3 mL, 420 mmol) at 0 °C. The reaction mixture was warmed to room temperature and heated at 100 °C for 3 hours. After completion of the reaction, the excess phosphorus oxychloride (POCl3) was evaporated under reduced pressure, and the reaction mixture was diluted with ice water (200 mL) and neutralized with saturated aqueous sodium hydrogen carbonate solution. The aqueous layer was extracted with ethyl acetate (2 x 250 mL). The combined ethyl acetate layers were dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product, which was purified by silica gel on a CombiFlash system using hexane containing 50% ethyl acetate as the eluent to give 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-4-chloro-5-nitropyrimidine (5 g, 13.3 mmol, 63.4% yield). 1 1H-NMR (400 MHz, DMSO-d6) δ 8.93 (s, 1H), 8.64 (d, J = 2.0 Hz, 1H), 8.19 (d, J = 2.0 Hz, 1H), 3.09-3.03 (m, 2H), 1.26-1.21 (m, 3H); ESI MS (m / z) 376.8(MH)+。

[0510] Step - 5: Synthesis of 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-N-methyl-5-nitropyrimidin-4-amine

[0511] To a stirred solution of 1,4-dioxane (45 mL) containing 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-4-chloro-5-nitropyrimidine (4.5 g, 12 mmol) was added tetrahydrofuran containing methylamine (30 mL, 60 mmol) at 0 °C under nitrogen. The reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was concentrated to give 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-N-methyl-5-nitropyrimidin-4-amine (4.4 g, 11.9 mmol, 99% yield). 1H-NMR (400 MHz, DMSO-d6) δ 9.20 (s, 1H), 8.99 (d, J = 4.4 Hz, 1H), 8.56 (d, J = 2.0 Hz, 1H), 8.13 (d, J = 2.0 Hz, 1H), 3.10 (d, J = 4.9 Hz, 3H), 3.03 (q, J = 7.3 Hz, 2H), 1.22-1.16 (m, 3H); ESI MS (m / z) 369.9(MH)+。

[0512] Step - 6: Synthesis of 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-N4-methylpyrimidine-4,5-diamine

[0513] To a stirred solution of ethanol (50 mL) and water (50 mL) containing 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-N-methyl-5-nitropyrimidin-4-amine (5 g, 13.5 mmol), iron powder (7.5 g, 135 mmol) was added, followed by ammonium chloride (7.2 g, 135 mmol). The reaction mixture was heated at 80 °C for 16 h. After completion of the reaction, the reaction mixture was filtered while hot and washed with ethyl acetate (250 mL). The ethyl acetate layer was washed with water (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to give crude 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-N4-methylpyrimidine-4,5-diamine (4.5 g, 13.2 mmol, 98% yield) as a black solid, which could be directly used in the next step. ESI MS (m / z) 341.9 (MH)+。

[0514] Step - 7: Synthesis of 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine (Compound 112)

[0515] To 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-N4-methylpyrimidine-4,5-diamine (4 g, 11.76 mmol) was added anhydrous trifluoroacetic acid (33.2 mL, 235 mmol) at room temperature. The reaction mixture was heated at 50 °C for 20 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and diluted with ice water (200 mL). The reaction mixture was basified with 1 N aqueous NaOH solution and extracted with ethyl acetate (2 x 150 mL). The combined ethyl acetate layers were dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product, which was purified by silica gel column on a CombiFlash system using hexane containing 30% ethyl acetate as an eluent to give 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine (2.8 g, 6.7 mmol, 56.9% yield) as a white solid. 1 1H-NMR (400 MHz, DMSO-d6) δ 9.52 (s, 1H), 8.60 (d, J = 2.0 Hz, 1H), 8.18 (d, J = 2.0 Hz, 1H), 3.98 (d, J = 1.0 Hz, 3H), 3.03 (q, J = 7.4 Hz, 2H), 1.16 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 419.8(MH)+.

[0516] Step - 8: Synthesis of 2-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine (Compound 113)

[0517] The title compound 2-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine (2.8 g, 6.22 mmol, 96% yield) was prepared from 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine (2.7 g, 6.5 mmol) according to the reaction conditions described in Step 4 of Compound 38 (Example 1). 1H-NMR (400 MHz, DMSO-d6) δ 9.54 (s, 1H), 9.18 (d, J = 2.4 Hz, 1H), 8.63 (d, J = 2.1 Hz, 1H), 3.98 (d, J = 1.2 Hz, 3H), 3.83 (q, J = 7.4 Hz, 2H), 1.25 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 450(MH)+。

[0518] Step - 9: Synthesis of 2-(5-(3,5-difluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine (Compound 122)

[0519] To a stirred solution of 2-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine (200 mg, 0.44 mmol) in dioxane (5 mL) and water (1 mL), (3,5-difluorophenyl)boronic acid (70.1 mg, 0.44 mmol) and potassium carbonate (135 mg, 0.98 mmol) were added under a nitrogen atmosphere. A complex of 1,1’-bis(diphenylphosphino)ferrocene-palladium(II) dichloromethane (36.3 mg, 0.045 mmol) was added to the reaction mixture, degassed with nitrogen and heated at 100 °C for 2 h. After completion of the reaction, the reaction mixture was filtered through celite and washed with ethyl acetate. The ethyl acetate layer was washed with water (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain a crude product, which was purified by silica gel column on a CombiFlash system using hexane containing 50% ethyl acetate as the eluent to give 2-(5-(3,5-difluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine (110 mg, 0.23 mmol, 51.2% yield) as a solid. 1H-NMR (400 MHz, DMSO-d6) δ 9.55 (s, 1H), 9.37 (d, J = 2.2 Hz, 1H), 8.68 (d, J = 2.2 Hz, 1H), 7.82-7.78 (m, 2H), 7.43 (tt, J = 9.3, 2.3 Hz, 1H), 4.04-3.99 (m, 3H), 3.83 (q, J = 7.4 Hz, 2H), 1.28 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 484.05(MH)+。

[0520] Example - 20: Synthesis of 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)(imino)(methyl)-l6-sulfanone (Compound 200)

[0521] Step - 1: Synthesis of 5-(3-(ethylsulfonyl)-6-(methylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 195)

[0522] A stirred solution of anhydrous N,N-dimethylformamide (4 mL) containing 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (600 mg, 1.53 mmol) (Step 1; Example - 7) was added dropwise at 0 °C with an aqueous solution of sodium thiomethoxide (0.46 mL, 1.38 mmol) over 15 minutes. The reaction mixture was warmed to room temperature and stirred for an additional 2 hours. After completion of the reaction, it was cooled to 0 °C and diluted with ice water (40 mL). The aqueous solution was extracted with ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography using hexane containing 20% ethyl acetate as the eluent to give 5-(3-(ethylsulfonyl)-6-(methylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (400 mg, 0.99 mmol, 64.7% yield). 1 1H-NMR (400 MHz, DMSO-d6) δ 9.45 - 9.42 (m, 1H), 8.24 - 8.22 (m, 1H), 7.74 (d, J = 8.6 Hz, 1H), 7.69 (d, J = 7.3 Hz, 1H), 7.45 (d, J = 6.1 Hz, 1H), 3.82 (q, J = 7.4 Hz, 2H), 2.62 (s, 3H), 1.25 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 402.90 (MH) + .

[0523] Step - 2: Synthesis of (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)(imino)(methyl)-l6-sulfanone (Compound 200)

[0524] A stirred solution of methanol (15 mL) containing 5-(3-(ethylsulfonyl)-6-(methylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (400 mg, 0.99 mmol) was cooled to 0 °C, and ammonium carbamate (233 mg, 2.98 mmol) was added portion wise, followed by the addition of diacetoxyiodobenzene (640 mg, 1.99 mmol) to obtain a mixture of 5-pyridin-2-yl and pyrimidine-1.0 mmol. After the addition was complete, the reaction mixture was warmed to room temperature and stirred for an additional 15 hours. After completion of the reaction, the reaction mixture was diluted with ice water (150 mL) and extracted with dichloromethane (2 x 50 mL). The combined dichloromethane layers were dried over anhydrous sodium sulfate, filtered, and concentrated to give a crude product, which was purified by silica gel column chromatography using hexane containing 90% ethyl acetate as the eluent to give (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)(imino)(methyl)l6-sulfanone (70 mg, 0.16 mmol, yield 16.25%). 1 1H-NMR (400 MHz, DMSO-d6) δ 9.51 (dd, J = 7.3, 0.7 Hz, 1H), 8.80 (d, J = 8.3 Hz, 1H), 8.44 (d, J = 8.3 Hz, 1H), 7.77 (d, J = 7.1 Hz, 1H), 7.54 (s, 1H), 4.88 (s, 1H), 4.02 - 3.93 (m, 2H), 3.29 (d, J = 1.2 Hz, 3H), 1.23 (dt, J = 51.4, 7.2 Hz, 3H); ESI MS (m / z) 434.30 (MH)+.

[0525] Example - 21: Synthesis of 5-(3-(ethylsulfonyl)-6-(methylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 196).

[0526] The title compound 5-(3-(ethylsulfonyl)-6-(methylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (118 mg, 0.27 mmol, 54.7% yield) was prepared from 5-(3-(ethylsulfonyl)-6-(methylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Step 1; Example 20) (200 mg, 0.50 mmol) according to the reaction conditions described in Step 4 of Compound 38 (Example 1). 1 1H-NMR (400 MHz, DMSO-d6) δ 9.52 (dd, J = 7.3, 0.7 Hz, 1H), 8.85 (d, J = 8.1 Hz, 1H), 8.46 (d, J = 8.3 Hz, 1H), 7.80 (d, J = 7.3 Hz, 1H), 7.56 (s, 1H), 3.97 (q, J = 7.4 Hz, 2H), 3.44 (s, 3H), 1.30 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 434.95 (MH) + 。

[0527] Example - 22a: Synthesis of 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetonitrile (Compound 217)

[0528] Step - 1: Synthesis of tert-butyl 2-cyano-2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetate (Compound 214)

[0529] tert-Butyl 2-cyanoacetate (238 mg, 1.69 mmol) was dissolved in N,N-dimethylformamide (20 mL) and cooled to 0 °C under a nitrogen atmosphere. Sodium hydride (86 mg, 2.15 mmol) was added portionwise to this solution, and the mixture was stirred at the same temperature for 15 minutes. Then, 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Step-1; Example-7) (600 mg, 1.54 mmol) was added. After the addition was complete, the reaction mixture was warmed to room temperature and stirred for an additional 12 hours. Next, the reaction mixture was diluted with ice-cold saturated ammonium chloride solution (200 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography using hexane containing 40% ethyl acetate as the eluent to give tert-butyl 2-cyano-2-(5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetate (500 mg, 1.01 mmol, 65.7% yield). 1 1H-NMR (400 MHz, DMSO-d6) δ 13.92 (s, 1H), 9.55 (d, J = 6.1 Hz, 1H), 8.10 (d, J = 9.5 Hz, 1H), 7.78 (d, J = 7.6 Hz, 1H), 7.59 (s, 1H), 7.37 (d, J = 9.5 Hz, 1H), 3.56 (q, J = 7.2 Hz, 2H), 1.44 (s, 9H), 1.20 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 494.30 (MH) - 。

[0530] Step-2: Synthesis of 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetonitrile (Compound 217)

[0531] tert-Butyl 2-cyano-2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetate (400 mg, 0.81 mmol) was treated with trifluoroacetic acid (TFA) (4 mL) at 0 °C. The reaction mixture was warmed to room temperature and stirred for 12 h. After completion of the reaction, trifluoroacetic acid (TFA) was evaporated to give the crude product, which was diluted with ice water (30 mL) and extracted with ethyl acetate (2 x 30 mL). The combined organic layers were washed with brine (50 mL) and water (50 mL). Dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified by column chromatography on silica gel using hexane containing 40% ethyl acetate as the eluent to give 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetonitrile 22a (130 mg, 0.33 mmol, 40.7% yield) as a white solid. 1 1H-NMR (400 MHz, DMSO-d6) δ 9.46 (dd, J = 7.3, 0.7 Hz, 1H), 8.55 (d, J = 8.3 Hz, 1H), 7.88 (d, J = 8.3 Hz, 1H), 7.62 (d, J = 7.1 Hz, 1H), 7.48 (s, 1H), 4.51 (s, 2H), 3.86 (q, J = 7.4 Hz, 2H), 1.24 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 395.85 (MH)+. 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetonitrile (22b) (100 mg, 0.253 mmol, 41.8% yield) obtained as a by-product during the synthesis. 1H-NMR (400 MHz, DMSO-d6) δ 9.43 (dd, J = 7.3, 1.0 Hz, 1H), 8.44 (d, J = 8.3 Hz, 1H), 7.89 (s, 1H), 7.78 (d, J = 8.3 Hz, 1H), 7.57 (d, J = 7.3 Hz, 1H), 7.45 (s, 1H), 3.84 (q, J = 7.3 Hz, 2H), 1.10 (S, 9H), 1.11 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 470.05 (MH) + 。(Compound 225)

[0532] Example - 23: Synthesis of N-(Ethyl(oxo)(5-(4-(trifluoromethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanilidene)cyanamide (Compound 199)

[0533] Step - 1: Synthesis of Ethyl(imino)(5-(4-(trifluoromethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanone (Compound 98)

[0534] The title compound Ethyl(imino)(5-(4-(trifluoromethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanone (460 mg, 0.89 mmol, yield 43.2 %) was prepared from 5-(3-(Ethylthio)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Step 1; Example 3) (1.0 g, 2.06 mmol) according to the reaction conditions described in Step 2 of Compound 200 (Example 20). 1H-NMR (400 MHz, DMSO-d6) δ 9.42 (dd, J = 7.3, 1.0 Hz, 1H), 9.28 (d, J = 2.2 Hz, 1H), 8.65 (d, J = 2.2 Hz, 1H), 8.04 (dd, J = 6.6, 2.2 Hz, 2H), 7.58 (dd, J = 11.9, 7.7 Hz, 3H), 7.41 (s, 1H), 4.46 (s, 1H), 3.71 (q, J = 7.3 Hz, 2H), 1.25 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 516.10 (MH) + 。

[0535] Step - 2: Synthesis of N-(Ethyl(oxo)(5-(4-(trifluoromethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanilidene)cyanamide (Compound 199)

[0536] To a stirred solution of ethyl(imino)(5-(4-(trifluoromethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanone (300 mg, 0.58 mmol) and 4-dimethylaminopyridine (DMAP) (142 mg, 1.16 mmol) in dichloromethane (10 mL) was added cyanogen bromide (185 mg, 1.75 mmol), and the resulting reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted with dichloromethane (3 x 10 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product, which was purified by silica gel using a CombiFlash system with hexane containing 40% ethyl acetate as the eluent to give N-(Ethyl(oxo))(5-(4-(trifluoromethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanilidene)cyanamide (140 mg, 0.26 mmol, 44.5% yield).1 H-NMR (400 MHz, DMSO-d6) δ 9.55-9.52 (m, 2H), 8.80 (d, J = 2.0 Hz, 1H), 8.11 (dd, J = 6.8, 2.2 Hz, 2H), 7.84 (d, J = 7.3 Hz, 1H), 7.64 (d, J = 7.8 Hz, 2H), 7.58 (s, 1H), 4.43 (qd, J = 14.4, 7.3 Hz, 2H), 1.47 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 541.05 (MH) + 。

[0537] Example-24: Synthesis of 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine (Compound 223)

[0538] Step-1: Synthesis of tert-butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)carbamate (Compound 222)

[0539] A solution containing 5-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Step-4; Example 1) (600 mg, 1.38 mmol), cesium carbonate (719 mg, 2.21 mmol) and tert-butyl carbamate (210 mg, 1.79 mmol) was degassed under a nitrogen atmosphere for 10 - 15 minutes. Next, Xantphos (239 mg, 0.41 mmol) and palladium(II) acetate (18.57 mg, 0.08 mmol) were added, and the mixture was further stirred under nitrogen for several minutes. The reaction mixture was heated at 100 °C for 12 hours. After completion of the reaction, the reaction mixture was filtered through Celite and washed with ethyl acetate. The ethyl acetate layer was washed with brine solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude compound. This was purified by silica gel on a CombiFlash system using ethyl acetate and hexane as eluents to obtain tert-butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)carbamate (380 mg, 0.81 mmol, yield 58.5 %) as a solid. 1 1H-NMR (400 MHz, DMSO-d6) δ 10.29 (s, 1H), 9.38 (dd, J = 7.3, 0.7 Hz, 1H), 8.94 (d, J = 2.4 Hz, 1H), 8.72 (d, J = 2.2 Hz, 1H), 7.62 (d, J = 7.3 Hz, 1H), 7.43 (s, 1H), 3.93 (q, J = 7.4 Hz, 2H), 1.52 (s, 9H), 1.32 - 1.26 (m, 3H); ESI MS (m / z) 472 (MH)+.

[0540] Step-2: Synthesis of 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine (Compound 223)

[0541] To dioxane (5 ml) containing tert-butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)carbamate (620 mg, 1.31 mmol) was added concentrated hydrochloric acid (300 mg, 2.63 mmol). The reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reaction mixture was diluted with water (10 mL) and extracted with dichloromethane (3 x 10 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude compound, which was purified by silica gel on a CombiFlash system using ethyl acetate and dichloromethane as eluents to give 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine (75 mg, 0.20 mmol, 15.36% yield) as a solid. 1 1H-NMR (400 MHz, DMSO-d6) δ 9.27 (dd, J = 7.3, 1.0 Hz, 1H), 8.25 (d, J = 2.4 Hz, 1H), 7.63 (d, J = 2.7 Hz, 1H), 7.59 (d, J = 7.3 Hz, 1H), 7.32 (s, 1H), 6.47 (s, 2H), 3.95 (q, J = 7.4 Hz, 2H), 1.27 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 371.85 (MH)+.

[0542] Example - 25: Synthesis of 5-(ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine (Compound 218)

[0543] Step - 1: Preparation of tert-butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(methyl)carbamate (Compound 224)

[0544] tert-Butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)carbamate (Step-1; Example-24) (500 mg, 1.06 mmol) was slowly added to a stirred solution of sodium hydride (30.5 mg, 1.27 mmol) in N,N-dimethylformamide (15 ml) at 0 °C under nitrogen. Next, the reaction mixture was stirred at 0 °C for 15 minutes, and then iodomethane (0.20 ml, 3.18 mmol) was added. The reaction mixture was warmed to room temperature and stirred for 12 hours. After completion of the reaction, the reaction mixture was diluted with water (25 mL) and extracted with ethyl acetate (2 x 25 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. Filtration and concentration under reduced pressure gave a crude compound, which was purified by silica gel on a CombiFlash system using ethyl acetate and hexane as eluents to give tert-butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(methyl)carbamate (350 mg, 0.72 mmol, 68.0% yield) as a solid 1 1H-NMR (400 MHz, DMSO-d6) δ 9.40 (dd, J = 7.3, 1.0 Hz, 1H), 8.99 (d, J = 2.4 Hz, 1H), 8.43 (d, J = 2.6 Hz, 1H), 7.64 (d, J = 7.3 Hz, 1H), 7.44 (s, 1H), 3.91 (q, J = 7.4 Hz, 2H), 3.36 (s, 3H), 1.45 (s, 9H), 1.27 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 486 (MH)+.

[0545] Step-2: Synthesis of 5-(ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine (Compound 218)

[0546] From the title compound 5-(ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine (75 mg, 0.19 mmol, yield 43%), tert-butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(methyl)carbamate (220 mg, 0.45 mmol) was prepared according to the reaction conditions described in Step 2 of Compound 223 (Example 24). 1 1H-NMR (400 MHz, DMSO-d6) δ 9.28 (dd, J = 7.3, 1.0 Hz, 1H), 8.27 (d, J = 2.7 Hz, 1H), 7.60 (d, J = 7.3 Hz, 1H), 7.51 (d, J = 2.7 Hz, 1H), 7.32 (s, 1H), 7.07 (q, J = 5.1 Hz, 1H), 3.97 (q, J = 7.4 Hz, 2H), 2.85 (d, J = 4.9 Hz, 3H), 1.29 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 386 (MH)+.

[0547] Example - 26: Synthesis of 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)acetonitrile (Compound 232)

[0548] To a mixture of 5-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Step 4; Example-1) (1.0 g, 2.30 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole (0.538 g, 2.76 mmol) in DMSO (8 mL) and water (2 mL), potassium fluoride (0.40 g, 6.89 mmol) was added, and the reaction mixture was stirred for 10 minutes under a nitrogen purge. Then, 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium(II) dichloromethane adduct (0.188 g, 0.23 mmol) was added. The resulting reaction mixture was heated at 90 °C for 3 hours. The reaction mixture was cooled to room temperature, and water (30 mL) was added. The aqueous layer was extracted with ethyl acetate (3 x 20 mL), the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting crude compound was used directly in the next reaction. ESI MS (m / z) 423.85 (MH)+.

[0549] The above crude product was dissolved in methanol (25 mL), and water (5 mL) containing potassium fluoride (0.137 g, 2.36 mmol) was added. The resulting reaction mixture was stirred at 90 °C for 16 hours. The reaction mixture was cooled to room temperature and diluted with water (30 mL). The aqueous layer was extracted with ethyl acetate (3 x 20 mL), the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude purification product. This was purified by silica gel on a CombiFlash system using ethyl acetate and hexane as eluents to give 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)acetonitrile (420 mg, 1.06 mmol, yield 45.0%) as a solid. 1H-NMR (400 MHz, DMSO-d6) δ 9.45 (dd, J = 7.3, 1.0 Hz, 1H), 9.02 (d, J = 2.2 Hz, 1H), 8.52 (d, J = 2.2 Hz, 1H), 7.66 (d, J = 7.3 Hz, 1H), 7.48 (s, 1H), 4.38 (s, 2H), 3.91 (q, J = 7.4 Hz, 2H), 1.28 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 395.6 (MH)+。

[0550] Example - 27: Synthesis of 5-(6-Ethyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 173)

[0551] A stirred solution of 5-(6-Chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Step 1; Example 7) (200 mg, 0.51 mmol) and tributyl(1-propynyl)tin (202 mg, 0.51 mmol) was dissolved in dioxane, and the compound was prepared. 61 mmol) was degassed thoroughly by subjecting it to three cycles of vacuum / nitrogen in dioxane (6 mL), and tetrakis(triphenylphosphine)palladium(0) (59.1 mg, 0.05 mmol) was added. The reaction mixture was heated at 90 °C for 1 hour. After completion of the reaction, the reaction mixture was cooled to room temperature and diluted with ethyl acetate (20 mL) and water (20 mL). The aqueous layer was extracted with ethyl acetate (2 x 5 mL), and the combined ethyl acetate layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product, which was purified by column chromatography on silica gel using hexane containing 20% ethyl acetate as the eluent to give 5-(3-(Ethylsulfonyl)-6-(prop-1-yn-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (100 mg, 0.25 mmol, 49.5% yield) as a solid. 1H-NMR (400 MHz, DMSO-d6) δ 9.43 (dt, J = 7.3, 0.9 Hz, 1H), 8.43 (dd, J = 8.3, 1.0 Hz, 1H), 7.87 (dd, J = 8.3, 1.0 Hz, 1H), 7.62 (dd, J = 7. 2, 1.1 Hz, 1H), 7.46 (d, J = 2.7 Hz, 1H), 3.84 (q, J = 7.4 Hz, 2H), 2.16 (s, 3H), 1.25 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 395.00 (MH)+。

[0552] Example - 28: Synthesis of 5-(3-(Ethylsulfonyl)-6-isopropoxypyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 240)

[0553] To a stirred solution of THF (4 mL) containing propan-2-ol (46.1 mg, 0.77 mmol) at 0 °C was slowly added NaH (33.8 mg, 0.84 mmol). After stirring at 0 °C for 15 minutes, 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Step 1; Example 7) (300 mg, 0.77 mmol) was added, and the reaction mixture was warmed to room temperature and stirred for an additional 6 hours. After completion of the reaction, the reaction mixture was diluted with a saturated solution of ammonium chloride (25 mL) and extracted with ethyl acetate (2 x 20 mL). The combined ethyl acetate layers were dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product, which was purified by column chromatography on silica gel using hexane containing 20% ethyl acetate as the eluent to give 5-(3-(ethylsulfonyl)-6-isopropoxypyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (98 mg, 0.24 mmol, 30.8% yield). 1H-NMR (400 MHz, DMSO-d6) δ 9.43 (dd, J = 7.3, 0.7 Hz, 1H), 8.28 (d, J = 9.0 Hz, 1H), 7.65 (d, J = 7.3 Hz, 1H), 7.45 (s, 1H), 7.13 (d, J = 8.8 Hz, 1H), 5.40-5.33 (m, 1H), 3.78 (q, J = 7.3 Hz, 2H), 1.34 (d, J = 6.1 Hz, 6H), 1.24 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 414.60 (MH) + 。

[0554] Example - 29: Synthesis of 5-(3-(Ethylsulfonyl)-6-isopropoxypyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 241)

[0555] 5-(6-Chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Step - 1; Example - 7) (300 mg, 0.77 mmol) and propan - 2 - amine (68.1 mg, 1.152 mmol) were added to a stirred solution of anhydrous acetonitrile (4 mL) at room temperature containing cesium carbonate (500 mg, 1.53 mmol), and the reaction mixture was stirred at 50 °C for 12 h. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ice water (30 mL), and extracted with ethyl acetate (2 x 30 mL). The combined ethyl acetate layers were washed with water (50 mL) and brine (50 mL), and dried over anhydrous sodium sulfate. Filtration and concentration gave the crude product, which was purified by column chromatography on silica gel using hexane containing 40% ethyl acetate as the eluent to give 5-(ethylsulfonyl)-N-isopropyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine (169 mg, 0.41 mmol, 53.2% yield). 1H-NMR (400 MHz, DMSO-d6) δ 9.35 (dd, J = 7.3, 0.7 Hz, 1H), 7.87 (d, J = 9.0 Hz, 1H), 7.74 (d, J = 7.3 Hz, 1H), 7.50 (d, J = 7.3 Hz, 1H), 7.37 (s, 1H), 6.67 (d, J = 9.0 Hz, 1H), 4.02 (q, J = 7.1 Hz, 1H), 3.63 (q, J = 7.3 Hz, 2H), 2.01 (t, J = 7.5 Hz, 3H), 1.62 (d, J = 6.1 Hz, 6H); ESI MS (m / z) 414 (MH) + 。

[0556] Example - 30: Synthesis of 5-(6-Ethyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 209)

[0557] The title compound 5-(6-Ethyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (128 mg, 0.33 mmol, 43.4% yield) was prepared from 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Step 1; Example - 7) (300 mg, 0.77 mmol) and ethyl trifluoroborate (125 mg, 0.92 mmol) according to the reaction conditions described in Step 9 of Compound 122 (Example 19). 11H-NMR (400 MHz, DMSO-d6) δ 9.42 (dd, J = 7.3, 0.7 Hz, 1H), 8.39 (d, J = 8.1 Hz, 1H), 7.74 (d, J = 8.3 Hz, 1H), 7.63 (d, J = 7.3 Hz, 1H), 7.44 (s, 1H), 3.83 (q, J = 7.4 Hz, 2H), 2.95 (q, J = 7.6 Hz, 2H), 1.27 (t, J = 7.3 Hz, 3H), 1.27 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 385.35 (MH) + 。

[0558] Example-31: Synthesis of 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinonitrile (Compound 138)

[0559] Step-1: Synthesis of 5-(ethylthio)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinonitrile

[0560] To a stirred solution of anhydrous N,N-dimethylformamide (20 mL) containing 5-(5-bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (1.0 g, 2.48 mmol) (Step 3; Example 1) under a nitrogen atmosphere, zinc cyanide (1.019 g, 8.68 mmol) was added. Tris(dibenzylideneacetone)dipalladium(0) (0.114 g, 0.12 mmol) was added to the above solution, followed by 1,1'-bis(diphenylphosphino)ferrocene (0.137 g, 0.25 mmol). The resulting reaction mixture was heated at 150 °C for 2 hours. After completion of the reaction, the reaction mixture was filtered through Celite and washed with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product, which was purified by silica gel using a CombiFlash system with hexane containing 15% ethyl acetate as the eluent to obtain 5-(ethylthio)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinonitrile (300 mg, 0.86 mmol, yield 34.6%) as a solid. 1 1H-NMR (400 MHz, DMSO-d6) δ 9.39-9.37 (m, 1H), 8.94 (d, J = 1.7 Hz, 1H), 8.48 (d, J = 1.7 Hz, 1H), 7.93 (d, J = 7.3 Hz, 1H), 7.45 (s, 1H), 3.09 (q, J = 7.3 Hz, 2H), 1.24 (t, J = 7.3 Hz, 3H); ESI MS (m / z) 350.0 (MH) + 。

[0561] Step - 2: Synthesis of 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinonitrile (Compound 138)

[0562] The title compound 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinonitrile (72 mg, 0.19 mmol, 13.19 %) was prepared from 5-(ethylthio)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinonitrile (500 mg, 1.43 mmol) according to the reaction conditions described in Step 4 of Compound 38 (Example 1). 1 1H-NMR (400 MHz, DMSO-d6) δ 9.50-9.48 (m, 2H), 8.99 (d, J = 1.8 Hz, 1H), 7.69 (d, J = 7.3 Hz, 1H), 7.54 (s, 1H), 3.92 (q, J = 7.4 Hz, 2H), 1.30 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 381.95 (MH)+.

[0563] Example - 32: Synthesis of ((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-sulfanone (Compound 172)

[0564] A stirred solution of 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Step-1; Example-7) (200 mg, 0.51 mmol), iminodimethyl-16-sulfanone (95 mg, 1.02 mmol), tripotassium phosphate (217 mg, 1.02 mmol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (48.8 mg, 0.10 mmol) in toluene (6.0 mL) was degassed under nitrogen for 10 minutes. To the above solution was added tris(dibenzylideneacetone)dipalladium(0) (46.9 mg, 0.05 mmol), and the reaction mixture was heated at 110 °C for 12 hours. After completion of the reaction, the reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (2 x 20 mL). The combined ethyl acetate layers were dried over anhydrous sodium sulfate, filtered and concentrated to obtain a crude product, which was purified by silica gel column chromatography using hexane containing 90% ethyl acetate as the eluent to give ((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-sulfanone (112 mg, 0.25 mmol, yield 48.9%). 1 1H-NMR (400 MHz, DMSO-d6) δ 9.41 (dd, J = 7.3, 1.0 Hz, 1H), 8.09 (d, J = 8.8 Hz, 1H), 7.57 (d, J = 7.3 Hz, 1H), 7.42 (s, 1H), 6.93(δ). 93 (d, J = 8.8 Hz, 1H), 3.74 (q, J = 7.4 Hz, 2H), 3.43 (d, J = 20.1 Hz, 6H), 1.23 (t, J = 7.5 Hz, 3H); ESI MS (m / z) 447.90 (MH)+.

[0565] Using appropriate starting materials and following the similar procedures described in Examples 1 to 32, the following compounds in Table-1 were obtained.

[0566]

Table 1-1

Table 1-2

Table 1-3

Table 1-4

Table 1-5

Table 1-6

Table 1-7

Table 1-8

Table 1-9

Table 1-10

Table 1-11

Table 1-12

Table 1-13

Table 1-14

Table 1-15

Table 1-16

Table 1-17

Table 1-18

Table 1-19

Table 1-20

Table 1-21

Table 1-22

Table 1-23

Table 1-24

Table 1-25

Table 1-26

Table 1-27

Table 1-28

Table 1-29

Table 1-30

Table 1-31

[0567] * Compound names generated using Chemdraw Professional 19.1

[0568] As described in this specification, the compounds of formula (I) exhibit insecticidal activity against a number of insects that attack important crops. The compounds of the present invention were evaluated for their activity as described in the following tests.

[0569] Biological Examples

[0570] Example A: Helicoverpa armigera

[0571] The required amount of the test compound was weighed and dissolved in a tube containing a solvent solution using the diet incorporation method. The tube was vortexed at 2000 rpm for 90 minutes for proper mixing. When the temperature in the bioassay container reached about 50 °C, a semi-synthetic diet was added to this solution. After thoroughly stirring and properly mixing the compound and the diet, it was cooled for 30 minutes. The solidified diet was cut into equal portions and transferred one by one to one cell of the bioassay tray. One starved third-instar larva was released into each cell of the bioassay tray, and the tray was covered with a lid. Thereafter, the bioassay tray was stored under laboratory conditions of a temperature of 25 °C and a relative humidity of 70%. 96 hours after releasing the larvae, the observation results of dead larvae, moribund larvae, and surviving larvae were recorded. The mortality rate was calculated by combining the dead and moribund larvae and compared with the results of the untreated control. Compounds 4, 7, 8, 29, 34, 38, 39, 41, 66, 70, 75, 76, 94, 96, 98, 100, 111, 126, 127, 136, 155, 156, 160, 166, 192, 203, 229, 231, and 235 recorded a mortality rate of ≧70% at 300 PPM.

[0572] Example B: Spodoptera litura

[0573] The diet intake method was used, in which a necessary amount of the test compound was weighed and dissolved in a tube containing a solvent solution. The tube was vortexed at 2000 rpm for 90 minutes for proper mixing. When the temperature in the bioassay container reached about 50 °C, semi-synthetic diet was added to this solution. After the compound and the diet were sufficiently stirred and properly mixed, they were cooled for 30 minutes. The solidified diet was cut into equal portions and transferred one by one to one cell of the bioassay tray. One starved third-instar larva was placed in each cell of the bioassay tray, and the tray was covered with a lid. Then, the bioassay tray was stored under laboratory conditions of a temperature of 25 °C and a relative humidity of 70%. 96 hours after the larvae were released, the observations of dead larvae, moribund larvae, and surviving l...

Claims

1. A compound of formula (I), 【Chemical 1】 Formula (I) wherein R １ is selected from the group consisting of C １ to C ６ -alkyl, C ２ to C ６ -alkenyl, C ２ to C ６ -alkynyl, C １ to C ６ -haloalkyl, C ２ to C ６ -haloalkenyl, C ３ to C ８ -cycloalkyl and C ３ to C ８ -cycloalkyl-C １ to C ６ -alkyl Y represents O or NR Ｙ ; R Ｙ is selected from the group consisting of hydrogen, cyano, C １ to C ４ -alkyl, C ２ to C ４ -alkenyl, C ２ to C ４ -alkynyl, C １ to C ４ -haloalkyl, C ２ to C ４ -haloalkenyl, C ３ to C ５ -cycloalkyl and C ３ to C ５ -cycloalkyl-C １ to C ３ -alkyl; R ２ is selected from the group consisting of halogen, cyano, nitro, C １ to C ６ -alkyl, C ２ to C ６ -alkenyl, C ２ to C ６ -alkynyl, C １ to C ６ -haloalkyl, C ２ to C ６ -haloalkenyl, C ３ to C ８ -cycloalkyl, C １ to C ６ -cyanoalkyl, OR ４ , NR ５ R ６ , CR ４ =NR ５ , C(=O)R ８ , S(O) ０－２ R ７ , SCN, S(O) ０－１ R ９ =NR １０ , N=S(O) ０－１ (R ９ ) ２ , P(=O)(OR'') ２ , Si(R')[[]END] ３ , C ６ to C １０ -aryl, C ７ to C １４ -aralkyl and C ３ to C １０ -heterocyclyl; wherein each group of R ２ is optionally substituted with one or more groups of R ２ａ ; R ２ａ is selected from the group consisting of halogen, cyano, C １ to C ６ -alkyl, C ２ to C ６ -alkenyl, C ２ to C ６ -alkynyl, C １ to C ６ -haloalkyl, C ２ to C ６ -haloalkenyl, C ３ to C ８ -cycloalkyl, OR ４ , NR ５ R ６ , CR ４ =NR ５ , C(=O)R ８ , S(O) ０－２ R ７ , SCN, S(O) ０－１ R ９ =NR １０ , N=S(O) ０－１ (R ９ ) ２ , Si(R') ３ , C ６ to C １０ -aryl, C ７ to C １４ -aralkyl and C ３ to C １０ -heterocyclyl; wherein each group of R ２ａ is optionally substituted with one or more groups of R ２ａａ ; or Two Rs ２ａ The substituents, together with the atoms to which they are attached, or together with further atoms selected from the group consisting of C, N, O, S, and optionally C(=O), C(=S), S(O) ０－２ and Si(R') ２ may form a 3- to 7-membered ring so as to include 1 to 3 ring members selected from the group consisting of, and a part thereof may be optionally substituted by one or more R ２ａａ groups; R ２ａａ is selected from the group consisting of halogen, cyano, C １ to C ６ -alkyl, C ２ to C ６ -alkenyl, C ２ to C ６ -alkynyl, C １ to C ６ -haloalkyl, C ２ to C ６ -haloalkenyl, C ３ to C ８ -cycloalkyl, OR ４ , NR ５ R ６ , C(=O)R ８ , S(O) ０－２ R ７ , S(O) ０－１ R ９ =NR １０ , N=S(O) ０－１ (R ９ ) ２ , Si(R') ３ , C ６ to C １０ -aryl, C ７ to C １４ -aralkyl and C ３ to C １０ -heterocyclyl; Q is a radical selected from the group consisting of formulae Q1a, Q1b, Q2a, Q2b, Q3, Q4a, Q4b, and Q ５ and is further optionally substituted with one or more R ３ and R ３’ ; 【Chemical Formula 2】 ； However, Q is bonded to the C of the pyridine ring ２ carbon or C ５ is bonded to carbon, R ３ is selected from the group consisting of hydrogen, halogen, cyano, nitro, C １ to C ６ -alkyl, C ２ to C ６ -alkenyl, C ２ to C ６ -alkynyl, C １ to C ６ -haloalkyl, C ２ to C ６ -haloalkenyl, C ３ to C ８ -cycloalkyl, OR ４ , NR ５ R ６ , CR ４ =NR ５ , C(=O)R ８ , S(O) ０－２ R ７ , SCN, S(O) ０－１ R ９ =NR １０ , N=S(O) ０－１ (R ９ ) ２ , P(=O)(OR'')[[]] ２ ２ , Si(R')[[[]] ３ ３ , C ６ to C １０ -aryl, C ７ to C １４ -aralkyl and C ３ to C ６ -heterocyclyl; where each group of R[[[]] ３ ３ is optionally substituted with one or more groups of R[[[]] ３ａ ３ａ ; R ３ａ is selected from the group consisting of halogen, cyano, C １ to C ６ -alkyl, C ２ to C ６ -alkenyl, C ２ to C ６ -alkynyl, C １ to C ６ -haloalkyl, C ２ to C ６ -haloalkenyl, C ３ to C ８ -cycloalkyl, OR ４ , NR ５ R ６ , C(=O)R ８ , S(O) ０－２ R ７ , S(O) ０－１ R ９ =NR １０ , N=S(O) ０－１ (R ９ ) ２ , Si(R') ３ , C ６ to C １０ -aryl, C ７ to C １４ -aralkyl and C ３ to C １０ -heterocyclyl; R ３’ is selected from the group consisting of hydrogen, halogen, cyano, C １ to C ６ -alkyl, C ２ to C ６ -alkenyl, C ２ to C ６ -alkynyl, C １ to C ６ -haloalkyl, C ３ to C ８ -cycloalkyl, OR'' and N(R'') ２ ; wherein each group of R ３’ is optionally substituted with one or more groups of R ３ａ’ ; R ３ａ’ is selected from the group consisting of halogen, cyano, C ３ to C ８ -cycloalkyl, OR'' and N(R'') ２ ; R ４ is selected from the group consisting of hydrogen, C １ to C ６ -alkyl, C ２ to C ６ -alkenyl, C ２ to C ６ -alkynyl, C １ to C ６ -haloalkyl, C ２ to C ６ -haloalkenyl, C ３ to C ８ -cycloalkyl, S(O) ２ R ７ , Si(R') ３ , C ６ to C １０ -aryl, C ７ to C １４ -aralkyl and C ３ to C １０ -heterocyclyl; wherein each group of R ４ is optionally substituted with R ４ａ ; R ４ａ is selected from the group consisting of halogen, cyano, C １ to C ６ -alkyl, C ２ to C ６ -alkenyl, C ２ to C ６ -alkynyl, C １ to C ６ -haloalkyl, C ２ to C ６ -haloalkenyl, C ３ to C ８ -cycloalkyl, OR', NR'R'', S(O) ０－２ R', C(=O)R', Si(R') ３ , C ６ to C １０ -aryl, C ７ to C １４ -aralkyl and C ３ to C １０ -heterocyclyl; R ５ is selected from the group consisting of hydrogen, C １ ~C ６ -alkyl, C ２ ~C ６ -alkenyl, C ２ ~C ６ -alkynyl, C １ ~C ６ -haloalkyl, C ２ ~C ６ -haloalkenyl, C ３ ~C ８ -cycloalkyl, OR ４ , NR'R'', S(O) ０－２ R ７ , C(=O)R ８ , Si(R') ３ , C ６ ~C １０ -aryl, C ７ ~C １４ -aralkyl, C ３ ~C １０ -heterocyclyl, where each group of R ５ is optionally substituted by R ５ａ , and at this time R ５ａ is selected from the group consisting of halogen, cyano, C １ to C ６ -alkyl, C ２ to C ６ -alkenyl, C ２ to C ６ -alkynyl, C １ to C ６ -haloalkyl, C ２ to C ６ -haloalkenyl, C ３ to C ８ -cycloalkyl, OR', NR'R'', S(O) ０－２ R', C(=O)R', Si(R') ３ , C ６ to C １０ -aryl, C ７ to C １４ -aralkyl, and C ３ to C １０ -heterocyclyl; R ６ is selected from the group consisting of hydrogen, C １ to C ６ -alkyl, C ２ to C ６ -alkenyl, C ２ to C ６ -alkynyl, C １ to C ６ -haloalkyl, C ２ to C ６ -haloalkenyl, C １ to C ６ -cycloalkyl, and C(=O)R ８ ; and is selected from the group consisting of R ７ is selected from the group consisting of C １ to C ６ -alkyl, C ２ to C ６ -alkenyl, C ２ to C ６ -alkynyl, C １ to C ６ -haloalkyl, C ２ to C ６ -haloalkenyl, C ３ to C ８ -cycloalkyl, NR ５ R ６ , C ６ to C １０ -aryl, C ７ to C １４ -aralkyl and C ３ to C １０ -heterocyclyl, and each group of R ７ is optionally substituted with one or more groups of R ７ａ ; R ７ａ is selected from the group consisting of halogen, cyano, C １ to C ６ -alkyl, C ２ to C ６ -alkenyl, C ２ to C ６ -alkynyl, C １ to C ６ -haloalkyl, C ２ to C ６ -haloalkenyl, C ３ to C ８ -cycloalkyl, OR', NR'R'', S(O) ０－２ R', C(=O)R', C ６ to C １０ -aryl, C ７ to C １４ -aralkyl and C ３ to C １０ -heterocyclyl; R ８ is selected from the group consisting of hydrogen, C １ ~C ６ -alkyl, C ２ ~C ６ -alkenyl, C ２ ~C ６ -alkynyl, C １ ~C ６ -haloalkyl, C ２ ~C ６ -haloalkenyl, C ３ ~C ８ -cycloalkyl, OR ４ , NR ５ R ６ , N = S(O) ０－１ (R ９ ) ２ , C ６ ~C １０ -aryl, C ７ ~C １４ -aralkyl and C ３ ~C １０ -heterocyclyl; each group of R ８ is optionally substituted with one or more groups of R ８ａ ; R ８ａ is selected from the group consisting of halogen, cyano, C １ to C ６ -alkyl, C ２ to C ６ -alkenyl, C ２ to C ６ -alkynyl, C １ to C ６ -haloalkyl, C ２ to C ６ -haloalkenyl, C ３ to C ８ -cycloalkyl, OR', NR'R'', S(O) ０－２ R', C(=O)R', C ６ to C １０ -aryl, C ７ to C １４ -aralkyl and C ３ to C １０ -heterocyclyl; R ９ is selected from the group consisting of C １ to C ６ -alkyl, C ２ to C ６ -alkenyl, C ２ to C ６ -alkynyl, C １ to C ６ -haloalkyl, C ２ to C ６ -haloalkenyl, C ３ to C ８ -cycloalkyl, and C(=O)R ８ ; and is selected from the group consisting of R １０ is selected from the group consisting of hydrogen, cyano, C １ to C ６ -alkyl, C ２ to C ６ -alkenyl, C ２ to C ６ -alkynyl, C １ to C ６ -haloalkyl, C ２ to C ６ -haloalkenyl, C ３ to C ８ -cycloalkyl, Si(R') ３ S(O) ０～２ R ７ and C(=O)R ８ ; and is selected from the group consisting of Two Rs ９ substituents, or R ９ and R １０ substituents, together with the atoms to which they are attached, or are selected from the group consisting of C, N, O, S, and optionally C(=O), C(=S), S(O) ０－２ and Si(R') ２ may form a 4- to 7-membered ring together with additional atoms selected from the group consisting of 1 to 3 ring members, and that moiety may optionally be substituted with one or more groups by R'; R' is hydrogen, halogen, cyano, C １ ~C ６ -alkyl, C ２ ~C ６ -alkenyl, C ２ ~C ６ -alkynyl, C ３ ~C ８ -cycloalkyl, OR'', N(R'') ２ , S(O) ０－２ R'', C(=O)R'', C(=O)OR'' and C(=O)N(R'') ２ selected from the group consisting of; R'' is hydrogen, C １ ~C ６ -alkyl, C ２ ~C ６ -alkenyl and C ２ ~C ６ -alkynyl as well as C ３ ~C ８ -cycloalkyl, and is selected from the group consisting of; wherein each group of R'' is optionally substituted with halogen; R １ ~R １０ 、R Ｙ 、R ２ａ 、R ２ａａ 、R ３ａ 、R ３ａ’ 、R ４ａ 、R ５ａ 、R ７ａ and R ８ａ Each of the groups of R is optionally substituted by one or more groups selected from the group consisting of CN, R', OR', SR', N(R') ２ 、COOR' and CON(R') ２ and is optionally substituted by one or more groups selected from the group consisting of; ‘‘n’’ is an integer in the range from 0 to 1; ‘‘m’’ is an integer in the range from 0 to 3; or an agriculturally acceptable salt, stereoisomer, diastereoisomer, enantiomer, tautomer, polymorph, N-oxide or S-oxide thereof.

2. The compound of formula (I) is represented by a compound of formula (Ia): 【Chemical Formula 3】 Formula (Ia) wherein R １ 、R ２ 、Q, Y, n and m are as defined in claim 1. the compound of formula (I) according to claim 1.

3. The compound of formula (I) is represented by a compound of formula (Ib): 【Chemical Formula 4】 Formula (Ib) wherein R １ and R ２ , Q, Y, n and m are as defined in claim 1 the compound of formula (I) according to claim 1.

4. Q is Q １ａ or Q １ｂ wherein: 【Chemical Formula 5】 、 wherein R ３ and R ３’ are as defined in claim 1, the compound of formula (I) according to claim 1.

5. The compound of formula (I) is a compound of formula (Ia-Q １ａ ), represented by: 【Chemical Formula 6】 ; wherein R １ 、 R ２ 、 R ３ 、 Y, and m are as defined in claim 1. the compound of formula (I) according to claim 1.

6. The compound of formula (I) according to claim 1, wherein the compound of formula (I) is any of the following, <Compound No. 1> 5-(6-Chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 2> 5-(3-(Ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 3> 5-(3-(Ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 4> 5-(3-(Ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 5> 5-(6-(3,5-Dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 6> 7-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine; <Compound No. 7> 4-(4-Chlorophenyl)-2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one; <Compound No. 8> 4-(3,5-Dichlorophenyl)-2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one; <Compound No. 9> 5-(Ethylsulfonyl)-N-(4-(trifluoromethoxy)phenyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 10> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-4-(4-(trifluoromethoxy)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one; <Compound No. 11> 7-(5-Bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 12> 7-(5-Bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 13> 7-(5-(3,5-Dichlorophenyl)-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 14> 7-(3-(Ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 15> 5-(3-(Ethylsulfonyl)-6-phenylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 16> 5-(3-(Ethylsulfonyl)-6-(4-fluorophenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 17> 5-(3-(Ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 18> 4-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)benzonitrile; <Compound No. 19> 5-(3-(Ethylsulfonyl)-6-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 20> 5-(6-(4-Chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 21> 5-(3-(Ethylsulfonyl)-6-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 22> 5-(3-(Ethylsulfonyl)-6-(3-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 23> 3-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)benzonitrile; <Compound No. 24> 5-(5-Bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 25> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one; <Compound No. 26> 5-(6-(3-Chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 27> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one; <Compound No. 28> 5-(3-(Ethylsulfonyl)-6-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 29> 5-(5-Bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 30> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-7-((trifluoromethyl)thio)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one; <Compound No. 31> 5-(5-(Ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 32> 5-(3-(Ethylthio)-5-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 33> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-7-((trifluoromethyl)sulfonyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one; <Compound No. 34> 5-(3-(Ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 35> 6-(6-Chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 36> 6-(6-Chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 37> 5-(5-(Ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 38> 5-(3-(Ethylsulfonyl)-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 39> 5-(5-(Ethylsulfonyl)-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 40> 6-(3-(Ethylthio)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 41> 5-(3-(Ethylsulfonyl)-6-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 42> 6-(3-(Ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 43> 6-(3-(Ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 44> 6-(3-(Ethylsulfonyl)-6-(4-fluoro-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 45> 6-(3-(Ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 46> 6-(6-(4-Bromo-1H-imidazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 47> 6-(6-(4-Chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 48> 6-(6-(3,5-Dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 49> 4-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)pyridin-2-yl)benzonitrile; <Compound No. 50> 6-(3-(Ethylsulfonyl)-6-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 51> 6-(3-(Ethylsulfonyl)-6-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 52> 6-(3-(Ethylsulfonyl)-6-(3-methyl-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 53> 6-(6-(3-Bromo-1H-1,2,4-triazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 54> 6-(3-(Ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 55> 6-(3-(Ethylsulfonyl)-6-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 56> 6-(6-(4-Chloro-1H-pyrazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 57> 5-(3-(Ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 58> 6-(3-(Ethylsulfonyl)-6-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 59> 6-(3-(Ethylsulfonyl)-6-(1-methyl-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 60> 6-(3-(Ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 61> 5-(6-Chloro-5-(ethylthio)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 62> 5-(5-(Ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 63> 5-(3-(Ethylthio)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 64> 5-(6-Chloro-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 65> 6-(3-(Ethylsulfonyl)-6-(1H-1,2,3-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 66> 5-(3-(Ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 67> 5-(3-(Ethylthio)-5-(1-methyl-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 68> 6-(5-(Ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 69> 5-(3-(Ethylsulfonyl)-5-(3-methyl-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 70> 5-(3-(Ethylsulfonyl)-5-(4-fluoro-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 71> 5-(3-(Ethylsulfonyl)-5-(1-methyl-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 72> 5-(5-(Ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 73> 5-(5-(Ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 74> 5-(5-(Ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 75> 2-(3-(Ethylsulfonyl)-5-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one; <Compound No. 76> 5-(5-(3,5-Dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 77> 5-(5-(3,5-Dichlorophenyl)-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 78> 5-(3-(Ethylsulfonyl)-5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 79> 2-(3-(Ethylsulfonyl)-5-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one; <Compound No. 80> 4-(4-Chlorophenyl)-2-(3-(ethylsulfonyl)-5-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one; <Compound No. 81> 6-(6-Chloro-5-(ethylthio)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 82> (5-Bromo-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(ethyl)(imino)-l6-sulfanone; <Compound No. 83> 5-(5-(Ethylsulfonyl)-6-(3-methyl-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 84> 5-(5-(Ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 85> 5-(6-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 86> ((5-(Ethylthio)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)dimethyl-l6-sulfanone; <Compound No. 87> ((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)dimethyl-l6-sulfanone; <Compound No. 88> 5-(5-(4-Bromo-1H-pyrazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 89> 5-(5-(4-Chloro-1H-pyrazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 90> 5-(5-Bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 91> 6-(5-Bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 92> 6-(5-Bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 93> 6-(6-Chloro-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 94> 5-(3-(ethylsulfonyl)-5-(4-fluorophenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 95> 5-(3-(ethylsulfonyl)-5-(pyrimidin-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 96> 5-(3-(ethylsulfonyl)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 97> 5-(3-(ethylsulfonyl)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 98> Ethyl (imino)(5-(4-(trifluoromethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanone; <Compound No. 99> 5-(5-Bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 100> 5-(3-(Ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 101> 5-(5-(4-Chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 102> 5-(5-(3,5-Dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 103> 5-(5-(3,5-Difluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 104> 5-(3-(Ethylsulfonyl)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 105> 5-(3-(Ethylsulfonyl)-5-(4-fluorophenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 106> ((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)dimethyl-l6-sulfanone; <Compound No. 107> Diethyl((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)-l6-sulfanone; <Compound No. 108> Ethyl((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)(methyl)-l6-sulfanone; <Compound No. 109> 5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-ol; <Compound No. 110> 6-(3-(Ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 111> 5-(5-(3-Chloro-5-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 112> 2-(5-Bromo-3-(ethylthio)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 113> 2-(5-Bromo-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 114> 6-(3-(Ethylsulfonyl)-5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 115> Diethyl ((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)-1,6-sulfanone; <Compound No. 116> Ethyl ((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)(methyl)-1,6-sulfanone; <Compound No. 117> 2-(3-(Ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 118> 2-(3-(Ethylsulfonyl)-5-(4-fluorophenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 119> 2-(3-(Ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 120> 2-(3-(Ethylsulfonyl)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 121> 2-(3-(Ethylsulfonyl)-5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 122> 2-(5-(3,5-Difluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 123> 2-(5-(4-Chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 124> 2-(5-(4-Chloro-3-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 125> 5-(5-(3,5-Difluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 126> 5-(5-(4-Chloro-3-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 127> 5-(5-(3-Chloro-4-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 128> 2-(5-(3,5-Dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 129> 2-(3-(Ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 130> 2-(3-(Ethylsulfonyl)-5-(3-methyl-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 131> 2-(5-(3-Chloro-5-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 132> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)thiazole; <Compound No. 133> 5-(3-(Ethylsulfonyl)-5-(1-methyl-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 134> 5-(3-(Ethylsulfonyl)-5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 135> 5-(3-(Ethylsulfonyl)-5-(pyrimidin-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 136> 5-(5-Cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 137> 6-(6-(3-Chloro-5-fluorophenyl)-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 138> 5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinonitrile; <Compound No. 139> Diethyl ((5-(ethylsulfonyl)-6-(9-methyl-8-(trifluoromethyl)-9H-purin-2-yl)pyridin-3-yl)imino)-1,6-sulfanone; <Compound No. 140> 5-(3-(Ethylsulfonyl)-6-(3-fluoro-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 141> N-Cyclopropyl-5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 142> 5-(5-Cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 143> 5-(3-(Ethylsulfonyl)-5-(2-methoxypyrimidin-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 144> 5-(3-(Ethylsulfonyl)-5-(3-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 145> 5-(3-(Ethylsulfonyl)-5-(3-methyl-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 146> 5-(3-(Ethylsulfonyl)-5-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 147> 5-(5-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 148> 5-(5-(3-Chloro-1H-1,2,4-triazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 149> ((5-(Ethylsulfonyl)-6-(9-methyl-8-(trifluoromethyl)-9H-purin-2-yl)pyridin-3-yl)imino)dimethyl-l6-sulfanone; <Compound No. 150> 5-(Ethylsulfonyl)-6-(9-methyl-8-(trifluoromethyl)-9H-purin-2-yl)pyridin-3-ol; <Compound No. 151> 5-(3-(Ethylsulfonyl)-5-methylpyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 152> 5-(3-(Ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 153> 5-(3-(Ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 154> 6-(5-(Ethylsulfonyl)-6-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 155> 5-(5-(3,4-Dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 156> 5-(3-(Ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 157> 2-(3-(Ethylsulfonyl)-5-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; <Compound No. 158> 5-(3-(Ethylsulfonyl)-5-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 159> 5-(6-Chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 160> 5-(3-(Ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 161> 5-(5-(Cyclopropylmethoxy)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 162> 5-(5-(4-Chloro-3-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 163> 5-(5-(3,4-Dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 164> 5-(3-(Ethylsulfonyl)-5-methylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 165> 5-(6-Chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 166> 5-(Ethylsulfonyl)-N,N-dimethyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 167> 5-(Ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 168> N-Cyclopropyl-5-(ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 169> 5-(6-Chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 170> N-Cyclopropyl-5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine; <Compound No. 171> 5-(6-Cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 172> ((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-sulfanone; <Compound No. 173> 5-(3-(Ethylsulfonyl)-6-(prop-1-yn-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 174> 5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 175> N-Cyclopropyl-5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 176> N-Cyclopropyl-5-(ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 177> 5-(5-(3-Bromo-1H-1,2,4-triazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 178> 5-(3-(Ethylsulfonyl)-5-(prop-1-yn-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 179> ((5-(Ethylthio)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-sulfanone; <Compound No. 180> 5-(6-Cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 181> 5-(3-(Ethylthio)-6-methylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 182> 5-(3-(Ethylsulfonyl)-6-methylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 183> 5-(3-(Ethylsulfonyl)-6-methylpyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 184> ((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-sulfanone; <Compound No. 185> ((5-(Ethylthio)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-sulfanone; <Compound No. 186> Ethyl((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)(methyl)-16-sulfanone; <Compound No. 187> 5-(3-(Ethylthio)-6-methylpyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; <Compound No. 188> 5-(6-Cyclopropyl-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 189> 5-(5-Cyclopropyl-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 190> 5-(3-(Ethylthio)-5-(4-fluorophenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 191> 5-(3-(Ethylthio)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 192> Ethyl(5-(4-fluorophenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(imino)-l6-sulfanone; <Compound No. 193> Ethyl(imino)(5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanone; <Compound No. 194> (6-Chloro-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(ethyl)(imino)-l6-sulfanone; <Compound No. 195> 5-(3-(Ethylsulfonyl)-6-(methylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 196> 5-(3-(Ethylsulfonyl)-6-(methylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 197> 5-(3-(Ethylthio)-5-vinylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 198> (5-((Dimethyl(oxo)-l6-sulfanilidene)amino)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(ethyl)(imino)-l6-sulfanon; <Compound No. 199> N-(Ethyl(oxo)(5-(4-(trifluoromethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanilidene)cyanamide; <Compound No. 200> (5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)(imino)(methyl)-l6-sulfanon; <Compound No. 201> 5-(3-(Ethylsulfonyl)-5-(2-methylprop-1-en-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 202> Ethyl(imino)(5-(2-methylprop-1-en-1-yl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanon; <Compound No. 203> Ethyl(imino)(5-(3-(trifluoromethyl)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanon; <Compound No. 204> 5-(3-(Ethylsulfonyl)-5-(prop-1-en-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 205> 5-(5-(2-Cyclopropylvinyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 206> N-((5-((Dimethyl(oxo)-l6-sulfanilidene)amino)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(ethyl)(oxo)-l6-sulfanilidene)cyanamide; <Compound No. 207> N-(Ethyl(oxo)(5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-l6-sulfanilidene)cyanamide; <Compound No. 208> N-(Ethyl(5-(4-fluorophenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(oxo)-l6-sulfanilidene)cyanamide; <Compound No. 209> 5-(6-Ethyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 210> 5-(3-(Ethylsulfonyl)-6-(2-methylprop-1-en-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 211> 5-(5-Ethyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 212> 5-(3-(Ethylsulfonyl)-5-vinylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 213> 5-(5-Cyclobutyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 214> tert-Butyl 2-cyano-2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetate; <Compound No. 215> 5-(3-(Ethylsulfonyl)-6-(prop-1-en-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 216> (E)-5-(6-(2-Cyclopropylvinyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 217> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetonitrile; <Compound No. 218> 5-(Ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine; <Compound No. 219> 2-(5-(Ethylthio)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)acetonitrile; <Compound No. 220> 2-((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)oxy)-2-methylpropanamide; <Compound No. 221> 5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-ol; <Compound No. 222> tert-Butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)carbamate; <Compound No. 223> 5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine; <Compound No. 224> tert-Butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(methyl)carbamate; <Compound No. 225> N-(tert-Butyl)-2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetamide; <Compound No. 226> 5-(3-(Ethylsulfonyl)-6-methoxypyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 227> 5-(6-Ethoxy-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 228> 5-(6-Cyclobutyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 229> 5-(5-(Difluoromethoxy))-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 230> 5-(Ethylsulfonyl)-N,N-dimethyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine; <Compound No. 231> 5-(3-(Ethylsulfonyl)-5-(pyrimidin-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 232> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)acetonitrile; <Compound No. 233> N-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)cyclopropanecarboxamide; <Compound No. 234> 1-((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)hexahydro-1H-6-thiopyran 1-oxide; <Compound No. 235> 1-((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)-1H-6-thietane 1-oxide; <Compound No. 236> 5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-ol; <Compound No. 237> 5-(3-(Ethylsulfonyl)-6-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 238> 5-(3-(Ethylsulfonyl)-6-isopropylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 239> 5-(3-(Ethylsulfonyl)-6-(2,2,2-trifluoroethoxy)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 240> 5-(3-(Ethylsulfonyl)-6-isopropoxypyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 241> 5-(Ethylsulfonyl)-N-isopropyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 242> N-(Cyclopropylmethyl)-5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 243> 5-(3-(Ethylsulfonyl)-6-(thietan-3-yloxy)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 244> 5-(Ethylsulfonyl)-N-propyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; <Compound No. 245> 1-((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)-1,1,6-thietane 1-oxide; <Compound No. 246> N-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)cyclopropanecarboxamide; <Compound No. 247> 1-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)cyclopropane-1-carbonitrile; <Compound No. 248> N-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-N-methylacetamide; <Compound No. 249> 1-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)urea; <Compound No. 250> 1-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-1,3-dimethylurea; <Compound No. 251> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-2-methylpropanenitrile; <Compound No. 252> 5-(3-(Ethylsulfonyl)-5-(trifluoromethyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 253> 5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)picolylamide; <Compound No. 254> 5-(Ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)picolylamide; <Compound No. 255> Methyl 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinate; <Compound No. 256> 5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinic acid azetidin-1-yl; <Compound No. 257> (5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)methanone; <Compound No. 258> (5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(morpholino)methanone; <Compound No. 259> N-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)cyclopropanesulfonamide; <Compound No. 260> N-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-N-methylcyclopropanesulfonamide; <Compound No. 261> N-((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)(methyl)(oxo)-l6-sulfanilidene)cyanamide; <Compound No. 262> Ethyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)((trifluoromethyl)imino)-l6-sulfanon; <Compound No. 263> 2-((5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)oxy)-2-methylpropanenitrile; <Compound No. 264> 5-(3-(Ethylsulfonyl)-5-(pyridin-2-yloxy)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 265> 5-(5-(2,2-Difluorocyclopropyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; <Compound No. 266> tert-Butyl 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)hydrazine-1-carboxylate; <Compound No. 267> 1-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)ethan-1-one; <Compound No. 268> N-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-O-methylhydroxylamine and <Compound No. 269> 2-(5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-1,1,1-trifluoropropan-2-ol.

7. A composition comprising a compound of formula (I) according to claim 1 or an agriculturally acceptable salt, stereoisomer, diastereoisomer, enantiomer, tautomer, polymorph, or N-oxide thereof, and at least one additional component selected from the group consisting of surfactants and adjuvants.

8. The composition according to claim 7, further comprising at least one bioactive compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers or nutrients.

9. The composition according to claim 7, wherein the compound of formula (I) is in the range of 0.1% to 99% by weight based on the total weight of the composition.

10. The compound of formula (I) is in the range of 5 to 50% by weight based on the total weight of the composition. The composition according to claim 7.

11. The composition according to claim 7.

11. A combination comprising a biologically effective amount of a compound of formula (I) according to claim 1 and at least one additional bioactive compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutritional agents. Combination product.

12. Insect and mite pests Their habitats, breeding grounds, food supplies, plants, seeds, soil, areas, materials or environments in which they live or may live, or Materials, plants, seeds, soil, surfaces or spaces to be protected from pest attack or infestation Against A biologically effective amount of a compound of formula (I) according to claim 1, or an agriculturally acceptable salt, stereoisomer, diastereoisomer, enantiomer, tautomer, polymorph, or N-oxide thereof, or Their composition according to claim 7, or Their combination product according to claim 11 Contacting A method for controlling insect and mite pests, comprising Said method excluding methods for the treatment of the human or animal body by surgery or therapy. Method.

13. On crops A biologically effective amount of a compound of formula (I) according to claim 1, or an agriculturally acceptable salt, stereoisomer, diastereoisomer, enantiomer, tautomer, polymorph, or N-oxide thereof, or Their composition according to claim 7, or Their combination product according to claim 11 Contacting A method for protecting crops from attack or infestation by insect and mite pests.

14. The method according to claim 12 or 13, wherein said method comprises applying an effective amount of the compound of formula (I) in an amount of 1 gai to 5000 gai per hectare to agricultural and horticultural crops.

15. To seeds before sowing and / or after pre-germination A biologically effective amount of a compound of formula (I) according to claim 1, or an agriculturally acceptable salt, stereoisomer, diastereoisomer, enantiomer, tautomer, polymorph, or N-oxide thereof, or Their composition according to claim 7, or Their combination product according to claim 11 Contacting A method for protecting seeds, plants and parts of plants from soil insects and a method for protecting the roots and shoots of seedlings from soil and foliar insects.

16. For the control of insect and mite pests in agricultural and horticultural crops. The compound according to claim 1, or a salt, N-oxide, isomer or polymorph thereof, or the composition thereof according to claim 7, or the combination product thereof according to claim 11 for use.

17. The crop is any one of cereals, corn, sorghum, pearl millet (bajra in Hindi), rice, soybeans, oilseed and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus fruits and citrus trees, any horticultural plant, cucurbitaceous plants, oil-bearing plants, tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton, potato, tomato, onion, pepper, other vegetables and foliage plants, The use according to claim 16.

18. A seed comprising the compound according to claim 1, or a salt, N-oxide, isomer or polymorph thereof, or the composition thereof according to claim 7, or the combination thereof according to claim 11 wherein the amount of the compound of formula (I) in the seed is from about 0.0001% to about 1% by weight,[[]]END]] seed.

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