Condensed heterocyclic compounds and their use as pest control agents

Abstract

The present invention discloses a fused heterocyclic compound of formula (I), wherein Q, R 1 、R 2 , n, m and Y are as defined in the specific embodiments. The present invention further discloses methods for preparing the compounds and uses of the compounds of formula (I) as pest control agents. #imgabs0#

Description

Technical Field

[0001] The present invention relates to fused heterocyclic compounds. More specifically, the present invention relates to fused heterocyclic compounds of formula (I) and methods for preparing the same. The present invention further relates to the use of fused heterocyclic compounds of formula (I) as pest control agents. Background Art

[0002] Currently available modern insecticides and acaricides must meet numerous requirements, for example with regard to their spectrum and level of efficacy, long-lasting activity, beneficial side effects, and possible uses. Over the past few decades, efforts have been underway to develop selective insecticides that have a specific action on a biochemical mode of action that is present only in insects or mites, but that additionally exhibit properties that differ from known insecticides in an advantageous manner.

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

[0004] However, due to the conventional use of such pesticides over the years, many pests have developed resistance and are no longer adequately controlled, a difficult situation that has become even more severe in recent years. Furthermore, some existing pesticides are highly toxic or, due to their residual properties, persist in the environment for a long time, which is becoming an increasingly serious problem due to the damage they cause to ecosystems.

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

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

[0007] It has now been found, surprisingly, that certain novel insecticidally active fused heterocyclic compounds having sulfur-containing substituents, which are the subject of the present invention, possess desirable advantageous properties as insecticides. Summary of the Invention

[0008] Therefore, 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]

[0010] Among them, Q, R 1 、R 2 , n, m and Y are as defined in the detailed description.

[0011] In one embodiment, the present invention provides a method for preparing a compound of formula (I) or an agriculturally acceptable salt thereof.

[0012] In another embodiment, the present invention provides a composition for controlling or preventing invertebrate pests, 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 surfactants and adjuvants.

[0013] In yet another embodiment, the composition additionally 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.

[0014] In another embodiment, the present invention provides a compound of formula (I), its agriculturally acceptable salts, isomers / structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs or N-oxides, compositions or combinations thereof, for use in controlling invertebrate pests in agricultural and / or horticultural crops or parasites on animals.

[0015] In another embodiment, the present invention provides a method for controlling invertebrate pests, comprising contacting the invertebrate pests, their habitats, breeding grounds, food supplies, plants, seeds, soils, areas, materials or environments in which the invertebrate pests grow or may grow, or materials, plants, seeds, soils, surfaces or spaces to be protected from attack or infestation by pests with a biologically effective amount of a compound of formula (I) or an agriculturally acceptable salt, isomer / structural isomer, stereoisomer, diastereomer, enantiomer, tautomer, metal complex, polymorph or N-oxide thereof, a combination or combination thereof. DETAILED DESCRIPTION

[0016] definition:

[0017] The definitions of terms used in this disclosure provided herein are for illustrative purposes only and do not limit the scope of the invention disclosed in this disclosure.

[0018] As used herein, the terms "comprising," "including," "having," "containing," "characterized by," or any other variations thereof, are intended to cover a non-exclusive inclusion, subject to any limitation expressly stated. For example, a composition, mixture, process, or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process, or method.

[0019] The transitional phrase "consisting of" excludes any element, step, or ingredient not specified. If included in a claim, this would exclude materials other than those listed, except for impurities typically associated with them. When the phrase "consisting of" appears in a clause of the body of a claim, rather than immediately following the preceding clause, it limits only the elements specified in that clause; other elements are not excluded from the claim as a whole.

[0020] The transitional phrase "consisting essentially of" is used to define a composition or method that includes materials, steps, features, components, or elements in addition to those literally disclosed, provided that such additional materials, steps, features, components, or elements do not materially affect the basic and novel characteristics of the claimed invention. The term "consisting essentially of" has a meaning intermediate between "comprising" and "consisting of."

[0021] In addition, unless expressly stated to the contrary, "or" refers to an inclusive "or" and not an exclusive "or". For example, the condition A "or" B satisfies any of the following conditions: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), and both A and B are true (or exist).

[0022] In addition, the indefinite articles "a" and "an" preceding an element or component of the present invention are intended to place no restriction on the number of instances (i.e., occurrences) of the element or component. Thus, "a" or "an" should be understood to include one or at least one, and the singular form of an element or component also includes the plural unless the number is obviously singular.

[0023] As used herein, the term "invertebrate pests" includes arthropods, gastropods, and nematodes that are economically important as pests. The term "arthropod" includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs, and symphylans. The term "gastropod" includes snails, slugs, and other animals of the order Stylommatophora. The term "nematode" refers to a living organism of the phylum Nematoda. The term "worm" includes roundworms, heartworms, herbivorous nematodes (Nematoda), flukes (Tematoda), acanthocephalians, and tapeworms (Cestoda).

[0024] The term "agronomy" refers to the production of field crops, e.g., for food, feed, and fiber, and includes the growing of corn, soybeans and other legumes, rice, cereals (e.g., wheat, oats, barley, rye, rice, corn), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, peppers, eggplant, crucifers, and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone fruit, and citrus), small fruits (berries, cherries), and other specialty crops (e.g., canola, sunflower, olives).

[0025] The term "non-agricultural" refers to applications other than field crops, such as horticultural crops (e.g., greenhouse, nursery, or ornamental plants not grown in the field), residential, agricultural, commercial, and industrial buildings, turf (e.g., sod farms, pastures, golf courses, lawns, athletic fields, etc.), wood products, storage, agroforestry and vegetation management, public health (i.e., humans), and animal health (e.g., domestic animals such as pets, livestock, and poultry, and non-domesticated animals such as wildlife).

[0026] Non-agricultural applications include protecting animals from invertebrate parasitic pests by administering to the animals to be protected a parasiticidally effective (i.e., biologically effective) amount of a compound of the present invention, typically in the form of a composition formulated for veterinary use. As used herein and in the claims, the terms "parasiticidal" and "parasiticidally" refer to an observable effect of providing protection against invertebrate parasitic pests to animals from pests. Parasiticidal effects typically involve reducing the occurrence or activity of target invertebrate parasitic pests. Such effects on pests include necrosis, death, growth retardation, reduced mobility or reduced ability to stay on or in the host animal, reduced feeding, and suppressed reproduction. These effects on invertebrate parasitic pests provide control (including prevention, reduction, or elimination) of animals from parasitic infestation or infection.

[0027] Compounds of the present disclosure may exist in pure form or as a mixture of different possible isomeric forms (e.g., stereoisomers or structural isomers). Various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, rotational isomers, tautomers, optical isomers, polymorphs, and geometric isomers. Any desired mixture of these isomers falls within the scope of the claims of the present disclosure. It will be understood by those skilled in the art that when enriched with respect to other isomers or separated from other isomers, a stereoisomer may be more active and / or may show a beneficial effect. In addition, those skilled in the art will know the process or method or technology of separating, enriching, and / or selectively preparing the isomer.

[0028] The meanings of various terms used in this specification will now be explained.

[0029] As used herein, the term "aliphatic compound" or "aliphatic group" is an organic compound in which carbon atoms are linked in straight chains, branched chains, or non-aromatic rings.

[0030] The term "alkyl" used alone or in compound words (e.g., "alkylthio" or "haloalkyl" or -N(alkyl) or alkylcarbonylalkyl or alkylsulfonylamino) includes straight or branched C1 to C 24 Alkyl, preferably C1 to C 15 Alkyl, more preferably C1 to C 10 Alkyl, most preferably C1 to C6 alkyl. Representative examples of alkyl groups include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl or different isomers. If an alkyl group is at the terminal end of a composite substituent, for example in an alkylcycloalkyl group, the initial part of the composite substituent, for example a cycloalkyl group, may be mono- or polysubstituted identically or differently and independently by alkyl groups. The same applies to composite substituents in which other groups (for example alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy, etc.) are at the terminal end.

[0031] The term "alkenyl" used alone or in compound words includes straight or branched C2 to C 24 Olefins, preferably C2 to C 15 Olefins, more preferably C2 to C 10Olefins, most preferably C2 to C6 olefins. Representative examples of olefins 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, alkenyl, 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 and different isomers. "Alkenyl" also includes polyenes, such as 1,2-propadienyl and 2,4-hexadienyl. Unless specifically defined elsewhere, this definition also applies to alkenyl groups that are part of a composite substituent, such as haloalkenyl, etc.

[0032] The term "alkynyl" used alone or in compound words includes straight or branched C2 to C 24 Alkynes, preferably C2 to C 15Alkynes, more preferably C2 to C 10 Alkynes, most preferably C2 to C6 alkynes. Non-limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 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 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 and different isomers. Unless specifically defined elsewhere, this definition also applies to alkynyl groups as part of a composite substituent, such as haloalkynyl, etc. The term "alkynyl" may also include moieties consisting of multiple triple bonds, such as 2,5-hexadiynyl.

[0033] The term "cycloalkyl" refers to an alkyl group that is closed to form a ring. Non-limiting examples include, but are not limited to, cyclopropyl, cyclopentyl, and cyclohexyl. Unless specifically defined elsewhere, this definition also applies to cycloalkyl groups that are part of a composite substituent, such as cycloalkylalkyl, etc.

[0034] The term "cycloalkenyl" refers to an alkenyl group that is closed to form a ring that includes a monocyclic, partially unsaturated hydrocarbon group. Non-limiting examples include, but are not limited to, cyclopropenyl, cyclopentenyl, and cyclohexenyl. Unless specifically defined elsewhere, this definition also applies to cycloalkenyl groups that are part of a composite substituent, such as cycloalkenylalkyl, etc.

[0035] The term "cycloalkynyl" refers to an alkynyl group that is closed to form a ring that includes a monocyclic, partially unsaturated group. Non-limiting examples include, but are not limited to, cyclopropynyl, cyclopentynyl, and cyclohexynyl. Unless specifically defined elsewhere, this definition also applies to cycloalkynyl groups that are part of a composite substituent, such as cycloalkynylalkyl, etc.

[0036] The terms "cycloalkoxy", "cycloalkenyloxy" and the like are defined similarly. Non-limiting examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy and cyclohexyloxy. Unless specifically defined elsewhere, this definition also applies to cycloalkoxy as part of a composite substituent, such as cycloalkoxyalkyl, etc.

[0037] The term "halogen" includes fluorine, chlorine, bromine or iodine, either alone or in a compound word such as "haloalkyl". In addition, when used for a compound word such as "haloalkyl", the alkyl group can be partially or entirely replaced by the same or different halogen atoms. The limiting examples of "haloalkyl" includes chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl and 1,1,1-trifluoropropyl-2-yl. This definition also applies to haloalkyl as part of a composite substituent, for example haloalkylaminoalkyl etc., unless defined specifically elsewhere.

[0038] The terms "haloalkenyl" and "haloalkynyl" are similarly defined, except that alkenyl and alkynyl are present as part of the substituent instead of alkyl.

[0039] The term "haloalkoxy" refers to a straight or branched alkoxy group, wherein some or all of the hydrogen atoms in these groups can be replaced by above-mentioned halogen atoms. The 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-trifluoropropane-2-oxy. Unless specifically defined elsewhere, this definition is also applicable to the haloalkoxy group as a part of a composite substituent, such as haloalkoxyalkyl etc.

[0040] The term "haloalkylthio" refers to the alkylthio of straight or branched chain, wherein some or all of the hydrogen atoms in these groups can be replaced by halogen atoms as described above. The limiting examples of halogenated alkylthio 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-trifluoropropyl-2-ylthio. This definition also applies to haloalkylthio as part of a composite substituent, for example haloalkylthioalkyl etc., unless defined elsewhere specifically.

[0041] 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.

[0042] The term "hydroxy" refers to -OH, amino refers to -NRR, where R can be H or any possible substituent, such as alkyl. Carbonyl refers to -C(O)-, carbonyloxy refers to -OC(O)-, sulfinyl refers to SO, and sulfonyl refers to S(O)2.

[0043] The term "alkoxy" used alone or in compound words includes C1 to C 24 Alkoxy, preferably C1 to C 15 Alkoxy, more preferably C1 to C 10Alkoxy, most preferably C1 to C6 alkoxy. Examples of alkoxy groups 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, hexyloxy, 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 composite substituent, for example haloalkoxy, alkynylalkoxy etc., unless defined specifically elsewhere.

[0044] The term "alkoxyalkyl" refers to an alkoxy substitution on an alkyl group. Non-limiting examples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2, and CH3CH2OCH2CH2.

[0045] The term "alkoxyalkoxy" refers to an alkoxy substitution on an alkoxy group.

[0046] The term "alkylthio" includes branched or straight chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, The following examples represent group A and B: butylthio, ...

[0047] The definitions of halocycloalkyl, halocycloalkenyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylcarbonyl, cycloalkylcarbonyl, haloalkoxyalkyl and the like are similar to those of the above examples.

[0048] The term "alkylthioalkyl" refers to an alkylthio group substituted on an alkyl group. Representative examples of "alkylthioalkyl" include -CH2SCH2, -CH2SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2, and CH3CH2SCH2CH2. "Alkylthioalkoxy" refers to an alkylthio group substituted on an alkoxy group. The term "cycloalkylalkylamino" refers to a cycloalkyl group substituted on an alkylamino group.

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

[0050] The term "alkoxycarbonyl" is an alkoxy group which is bonded to the skeleton via a carbonyl group (-CO-). Unless specifically defined elsewhere, this definition also applies to alkoxycarbonyl as part of a composite substituent, for example cycloalkylalkoxycarbonyl etc.

[0051] The term "alkoxycarbonylalkylamino" refers to an alkoxycarbonyl substitution on an alkylamino group. "Alkylcarbonylalkylamino" refers to an alkylcarbonyl substitution on an alkylamino group. The terms alkylthioalkoxycarbonyl, cycloalkylalkylaminoalkyl, etc. are defined similarly.

[0052] Non-limiting examples of “alkylsulfinyl” include, but are not limited to, methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 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. The term "arylsulfinyl" includes Ar-S(O), where Ar can be any carbocyclic or heterocyclic ring. This definition also applies to alkylsulfinyl as part of a composite substituent, for example haloalkylsulfinyl etc., unless specifically defined elsewhere.

[0053] Non-limiting examples of “alkylsulfonyl” include, but are not limited to, methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 1-methylpentylsulfonyl, 2-methyl The term "arylsulfonyl" includes Ar-S(O)2, wherein Ar can be any carbocyclic or heterocyclic ring. Unless specifically defined elsewhere, this definition also applies to alkylsulfonyl groups as part of a composite substituent, such as alkylsulfonylalkyl and the like.

[0054] Definitions of "alkylamino" and "dialkylamino" are similar to those of the above examples.

[0055] The term "carbocycle" or "carbocyclic" or "carbocyclyl" includes "aromatic carbocyclic ring systems" and "non-aromatic carbocyclic ring systems" or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds, wherein the rings can be aromatic or non-aromatic (wherein aromatic means that Huckel's rules are satisfied and non-aromatic means that Huckel's rules are not satisfied).

[0056] Non-limiting examples of non-aromatic carbocyclic ring systems are cyclopropyl, cyclobutyl, cyclopentyl, norbornyl, etc. Non-limiting examples of aromatic carbocyclic ring systems are phenyl, naphthyl, etc.

[0057] As used herein, the term "aryl" refers to any carbon-based aromatic group, including but not limited to phenyl, naphthalene, biphenyl, anthracene, etc. The aryl group may be substituted or unsubstituted. In addition, the aryl group may be a single ring structure or contain multiple ring structures, which may be fused ring structures or connected by one or more bridging groups such as carbon-carbon bonds.

[0058] The term "aryl" also includes "aralkyl," which refers to an aromatic hydrocarbon group comprising an alkyl portion as defined above. Examples include benzyl, phenethyl, and 6-naphthylhexyl. As used herein, the term "aralkenyl" refers to an aromatic hydrocarbon group comprising an alkenyl portion as defined above and an aryl portion as defined above. Examples include styryl, 3-(benzyl)prop-2-enyl, and 6-naphthylhex-2-enyl.

[0059] The term "hetero" in relation to a ring refers to a ring wherein at least one ring atom is not carbon and which may contain from 1 to 4 heteroatoms independently selected from nitrogen, oxygen and sulfur, provided that each ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs.

[0060] The term "aromatic" means that Huckel's rule is satisfied, and the term "non-aromatic" means that Huckel's rule is not satisfied.

[0061] The term "heterocycle" or "heterocyclic" or "heterocyclic ring system" includes "aromatic heterocycles" or "heteroaryl bicyclic ring systems" and "non-aromatic heterocyclic ring systems" or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds, wherein the rings may be aromatic or non-aromatic, wherein the heterocycle contains at least one radical selected from N, O, S(O) 0-2 The heteroatoms and / or C ring members of the heterocycle may be replaced by C(═O), C(═S), C(═CR*R*) and C═NR*, where * represents an integer.

[0062] The term "non-aromatic heterocycle" or "non-aromatic heterocyclic" refers to a 3- to 15-membered, preferably 3- to 12-membered, saturated or partially unsaturated heterocycle containing 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur: a mono-, bi- or tricyclic heterocycle which, in addition to carbon ring members, contains 1 to 3 nitrogen atoms and / or 1 oxygen or sulfur atom or 1 or 2 oxygen and / or sulfur atoms; if the ring contains more than one oxygen atom, they are not directly adjacent; for example (but not limited to) oxetanyl, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothiophenyl, 3-tetrahydrothiophenyl, 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-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,4-dihydrofuran-2-yl, 2,4-dihydrofuran-3-yl, 2,3-dihydrothiophen-2-yl, 2,3-dihydrothiophen-3-yl, 2,4-dihydrothiophen-2-yl, 2,4-dihydrothiophen-3-yl, pyrrolinyl, 2-pyrrolin-2-yl, 2-Pyrrolidine-3-yl, 3-pyrrolidine-3-yl, 3-pyrrolidine-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-1-yl, oxazol-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, piperazine pyridinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, pyrazinyl, morpholinyl, thiomorpholinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiophenyl, 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]azepine, -1- or -2- or -3- or -4- or -5- or -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepine -2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,4,7-tetrahydro[1H]azepine -1- or -2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,6,7-tetrahydro[1H]azepine -1- or -2- or -3- or -4- or -5- or -6- or -7-yl, hexahydroazepine -1- or -2- or -3- or -4-yl, tetra- and hexahydrooxa (e.g. 2,3,4,5-tetrahydro[1H]oxa -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), hexahydroazepine -1- or -2- or -3- or -4-yl, tetra- and hexahydro-1,3-diazepine Tetra- and hexahydro-1,4-diazepines Tetra- and hexahydro-1,3-oxazepines Tetra- and hexahydro-1,4-oxazepines Tetrahydro- and hexahydro-1,3-dioxa Tetrahydro- and hexahydro-1,4-dioxa This definition also applies to heterocyclyl as part of a composite substituent, for example heterocyclylalkyl etc., unless specifically defined elsewhere.

[0063] The term "heteroaryl" or "aromatic heterocycle" refers to a 5- or 6-membered, fully unsaturated monocyclic ring system containing 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur; if the ring contains more than one oxygen atom, 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 containing, 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; nitrogen-bonded five-membered heteroaryl containing 1 to 4 nitrogen atoms, or benzo-fused nitrogen-bonded five-membered heteroaryl containing 1 to 3 nitrogen atoms: a five-membered heteroaryl containing, in addition to carbon atoms, 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms as ring members, in which two adjacent carbon ring members or 1 nitrogen and 1 adjacent carbon ring member can be bridged by buta-1,3-diene-1,4-diyl, wherein 1 or 2 carbon atoms can be replaced by nitrogen atoms, wherein these rings are connected to the skeleton through 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.

[0064] 6-membered heteroaryl containing 1 to 4 nitrogen atoms: 6-membered heteroaryl containing 1 to 3 and 1 to 4 nitrogen atoms as ring members, respectively, in addition to carbon atoms, such as (but not limited to) 2-pyridyl, 3-pyridyl, 4-pyridyl, 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; phenyl containing 1 to 3 nitrogen atoms or 1 nitrogen atom and 1 oxygen or sulfur atom; and fused five-membered heteroaryl: 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 yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophene-2-yl, 1-benzothiophene-3-yl, 1-benzothiophene-4-yl, 1-benzothiophene-5-yl, 1-benzothiophene-6-yl, 1-benzothiophene-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; benzo-fused six-membered heteroaryl containing 1 to 3 nitrogen atoms, such as (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. Unless specifically defined elsewhere, this definition also applies to heteroaryl groups that are part of a composite substituent, such as heteroarylalkyl, etc.

[0065] Bicyclic 5-6 heteroaryl systems with one bridgehead (ring-connected) nitrogen atom containing one to three nitrogen atoms or one nitrogen atom and one 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-b]pyridazine, [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 and [1,2,4]triazolo[4,3-a]pyridine.

[0066] The term "trialkylsilyl" includes three branched and / or straight-chain alkyl groups attached to and linked through a silicon atom, such as trimethylsilyl, triethylsilyl, and tert-butyl-dimethylsilyl. "Halotrialkylsilyl" means 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" means 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 "trialkylsiloxy" means a trialkylsilyl moiety attached through an oxygen bond.

[0067] Non-limiting examples of "alkylcarbonyl" include C(O)CH, C(O)CHCHCH, and C(O)CH(CH). Non-limiting examples of "alkoxycarbonyl" include CHOC(=O), CHCHOC(=O), CHCHCHOC(=O), (CH)CHOC(=O), and different butoxy- or pentyloxycarbonyl isomers. Non-limiting examples of "alkylaminocarbonyl" include CHNHC(=O), CHCHNHC(=O), CHCHCHNHC(=O), (CH)CHNHC(=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), CH3CH2CH2OCH2C(=O), and CH3CH2OCH2CH2C(=O). Non-limiting examples of “alkylthioalkylcarbonyl” include CH3SCH2C(=O), CH3SCH2CH2C(=O), CH3CH2SCH2C(=O), CH3CH2CH2CH2SCH2C(=O), and CH3CH2SCH2CH2C(=O). The terms haloalkylsulfonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkylamino and the like are defined analogously.

[0068] Non-limiting examples of "alkylaminoalkylcarbonyl" include CH3NHCH2C(=O), CH3NHCH2CH2C(=O), CH3CH2NHCH2C(=O), CH3CH2CH2CH2NHCH2C(=O), and CH3CH2NHCH2CH2C(=O).

[0069] The term "amide" refers to A-R'C=ONR"-B, wherein R' and R" represent substituents, and A and B represent any groups.

[0070] The term "thioamide" refers to A-R'C=SNR"-B, where R' and R" represent substituents and A and B represent any group.

[0071] The total number of carbon atoms in a substituent is indicated by the prefix "C i -C j" represents, wherein i and j are numbers from 1 to 21. For example, C1-C3 alkylsulfonyl represents methylsulfonyl to propylsulfonyl; C2 alkoxyalkyl represents CH3OCH2; C3 alkoxyalkyl represents, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl represents various isomers of alkyl substituted with an alkoxy group containing a total of four carbon atoms, examples of which include CH3CH2CH2OCH2 and CH3CH2OCH2CH2. In the above description, when the compound of formula (I) contains one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacing a hydrogen on said carbon or nitrogen.

[0072] When a compound is substituted with a subscript substituent, this means that the number of said substituents may exceed 1, said substituents (when they exceed 1) being independently selected from the group of defined substituents. In addition, when (R) m When the subscript m in represents an integer ranging from 0 to 4, for example, the number of substituents can be selected from integers between 0 and 4, inclusive.

[0073] When a group contains a substituent which may be hydrogen, the group is considered unsubstituted when the substituent is hydrogen.

[0074] The embodiments herein and their various features and advantageous details are explained with reference to the non-limiting embodiments in the specification. Descriptions of well-known components and processing techniques are omitted so as not to unnecessarily obscure the embodiments herein. The examples used herein are intended only to facilitate an understanding of the manner in which the embodiments herein may be practiced and to further enable those skilled in the art to practice the embodiments herein. Therefore, these examples should not be construed as limiting the scope of the embodiments herein.

[0075] The description of the specific embodiments will fully reveal the general nature of the embodiments herein so that others can easily modify and / or adapt these specific embodiments for various applications by applying current knowledge without departing from the general concepts, and therefore, such adaptations and modifications should and are intended to be understood as being within the meaning and range of equivalents of the disclosed embodiments. It should be understood that the phraseology or terminology used herein is for the purpose of description and not limitation. Therefore, although the embodiments herein have been described in terms of preferred embodiments, those skilled in the art will recognize that the embodiments herein can be practiced with modifications within the spirit and scope of the embodiments described herein.

[0076] Any discussion of documents, acts, materials, devices, articles or the like that has been included in this specification is solely for the purpose of providing a context for the present disclosure and is not to be taken as an admission that any or all of these matters form part of the prior art base or were common general knowledge in the field relevant to the present disclosure, even if available anywhere before the priority date of this application.

[0077] While the numerical values ​​mentioned in the description and the description / claims may constitute an essential part of the present invention, any deviations from these numerical values ​​should still fall within the scope of the present invention if they follow the same scientific principles as the principles of the invention disclosed herein. If appropriate, the inventive compounds of the present invention may exist as mixtures of different possible isomeric forms, in particular stereoisomers, such as mixtures of E and Z, threo and erythro forms, as well as optical isomers and, if appropriate, tautomers. E and Z isomers, as well as threo and erythro isomers, as well as optical isomers, any desired mixtures of these isomers and possible tautomeric forms are disclosed and claimed.

[0078] The term "pest" for the purposes of this disclosure includes, but is not limited to, fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, insects, and rodents. Pests also include animals or plants that are harmful to humans or objects of human concern, including crops, livestock, and forestry.

[0079] The term "plants" is understood herein to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants that can be obtained by conventional breeding and optimization methods or by biotechnology and genetic engineering methods or a combination of these methods, including transgenic plants and including plant cultivars that are or are not protectable by plant breeders' rights.

[0080] For purposes of this disclosure, the term "plant" includes living organisms such as trees, shrubs, herbs, grasses, ferns, and mosses that generally grow in one location, absorb water and essential substances through their roots, and synthesize nutrients in their leaves by photosynthesis.

[0081] Examples of "plants" for the purposes of the present invention include, but are not limited to, crop plants, such as wheat, rye, barley, triticale, oats or rice; beets, such as sugar beets or fodder beets; fruits and fruit trees, such as pome, stone or soft fruit, for example apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; legumes, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconuts, cocoa beans, castor oil plants, oil palms, peanuts or soybeans; 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 plants, vegetables, such as spinach, lettuce (I the cucurbits or paprika; plants of the laurel family, such as avocados, cinnamon or camphor; the cucurbit family; oil-producing plants; energy and raw material plants, such as cereals, maize, soybeans, other leguminous plants, rapeseed, sugar cane or oil palm; tobacco; nuts; coffee; tea; cocoa; bananas; peppers; grapevines (table grapes and juice grapevines); hops; turf; sweet leaf (also known as stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreen plants, such as conifers; and plant propagation material, such as seeds, and crop material of these plants.

[0082] Preferably, plants used for the purposes of the present invention include, but are not limited to, cereals, corn, rice, soybeans and other legumes, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbits, oil-producing plants, tobacco, coffee, tea, cocoa, sugar beets, sugar cane, cotton, potatoes, tomatoes, onions, peppers and vegetables, ornamental plants, any flowering plants, and other plants used by humans and animals.

[0083] The term "plant part" is understood to mean all parts and organs of a plant both above and below ground. For the purposes of this disclosure, the term plant part includes, but is not limited to, cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots (including taproot, lateral roots, root hairs, root tips, root crowns), rhizomes, slips, shoots, fruits, fruiting bodies, bark, stem, buds, auxillary buds, meristems, nodes, and internodes.

[0084] The term "locus thereof" includes the soil, the surroundings of the plant or plant part and equipment or tools used before, during or after sowing / planting the plant or plant part.

[0085] Application of a compound of the disclosure, or a compound of the disclosure in a composition optionally comprising other compatible compounds, to plants or plant materials or the locus thereof includes application by techniques known to those skilled in the art including, but not limited to, spraying, coating, dipping, fumigating, impregnating, injecting, and dusting.

[0086] The term "applying" means attaching to a plant or plant part by physical or chemical means including impregnation.

[0087] In one embodiment, the present invention provides a compound of formula (I), or an agriculturally acceptable salt, isomer / structural isomer, stereoisomer, diastereomer, enantiomer, tautomer, polymorph, metal complex, N-oxide or S-oxide thereof:

[0088]

[0089] in,

[0090] 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;

[0091] Y represents O or NR Y ;

[0092] 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;

[0093] R 2 is selected from 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 -heterocyclic group; wherein R 2 Each group is optionally replaced by one or more R 2a group substitution;

[0094] R 2a is selected from 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) 0-2 R 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 -heterocyclic group; wherein R 2a Optionally, one or more R 2aa group substitution;

[0095] or

[0096] Two R's 2a The substituents together with the atoms to which they are attached or together with other atoms selected from C, N, O, S, and optionally include 1 to 3 atoms selected from C(=O), C(=S), S(O) 0-2 and Si(R')2 ring members, may form a 3 to 7 membered ring, a portion of which may be optionally replaced by one or more R 2aa group substitution;

[0097] R 2aa is selected from halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR 4 NR 5 R6 、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 -heterocyclic group;

[0098] Q is a group selected from the group consisting of formula Q1, Q2, Q3, Q4 and Q5, which is optionally replaced by one or more R 3 and R 3’ replace;

[0099]

[0100] The premise is that Q is attached to the C2 or C5 carbon of the pyridine ring;

[0101] R 3 is selected from 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; wherein R 3 Each group is optionally replaced by one or more R 3a group substitution;

[0102] R 3a is selected from 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 -heterocyclic group;

[0103] R 3 ' is selected from hydrogen, halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR" and N(R")2; wherein R 3 Each group of ' is optionally replaced by one or more R 3a ' group substitution;

[0104] R 3a ' group is selected from halogen, cyano, C3-C8-cycloalkyl, OR" and N(R")2;

[0105] R 4 selected from 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 -heterocyclic group; wherein R 4 Each group of R 4a replace;

[0106] R 4a is selected from 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 -heterocyclic group;

[0107] R 5is selected from 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 and C3-C 10 -heterocyclic group; wherein R 5 Each group of R 5a replace;

[0108] R 5a is selected from 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 -heterocyclic group;

[0109] R 6 is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-cycloalkyl and C(=O)R 8 ;

[0110] R 7 Selected from C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, NR 5 R 6 、C6-C 10 -aryl, C7-C 14 -aralkyl and C3-C 10 -heterocyclic group; wherein R 7 Each group is optionally replaced by one or more R 7a replace;

[0111] R 7a is selected from 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 -heterocyclic group;

[0112] R 8 is selected from 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 -heterocyclic group; wherein R 8 Each group is optionally replaced by one or more R 8a replace;

[0113] R 8a is selected from 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 -heterocyclic group;

[0114] R 9 selected from C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl and C(=O)R 8 ;

[0115] R 10 is selected from 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 ;

[0116] Two R's 9 Substituent or R 9 and R 10 The substituents together with the atoms to which they are attached or together with other atoms selected from C, N, O, S, and optionally including 1 to 3 atoms selected from C(=O), C(=S), S(O) 0-2and the ring members of Si(R')2, may form a 4- to 7-membered ring, some of which are optionally substituted with one or more R' groups;

[0117] R' is selected from 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;

[0118] R" is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl and C3-C8-cycloalkyl; wherein each radical of R" is optionally substituted by halogen;

[0119] R 1 to R 10 、R Y 、R 2a 、R 2aa 、R 3a 、R 3a’ 、R 4a 、R 5a 、R 7a and R 8a Each group in 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;

[0120] "n" is an integer from 0 to 1;

[0121] “m” is an integer from 0 to 3.

[0122] In a preferred embodiment, Q is selected from the formula Q 1a , Q 1b , Q 2a , Q 2b ,Q3,Q 4a , Q 4b and Q5;

[0123]

[0124] in,

[0125] R 3 and R 3' Same as the above definition.

[0126] In one embodiment, Q is selected from the formula Q 1a or Q 1b ;

[0127]

[0128] in,

[0129] R 3 and R 3' Same as the above definition.

[0130] In another embodiment, the compound of formula (I) is represented by a compound of formula (Ia);

[0131]

[0132] Among them, R 1 、R 2 , Q, Y, n and m are the same as defined above.

[0133] In yet another embodiment, the compound of formula (I) is represented by a compound of formula (Ib);

[0134]

[0135] Among them, R 1 、R 2 , Q, Y, n and m are the same as defined above.

[0136] In a preferred embodiment, the compound of formula (Ia) is represented by formula (Iaa);

[0137]

[0138] Among them, R 1 、R 2 , Q and m are the same as defined above.

[0139] In a preferred embodiment, the compound of formula (Ia) is represented by formula (Iab);

[0140]

[0141] Among them, R 1 、R 2 , Q, Y, n and m are the same as defined above.

[0142] In a preferred embodiment, the compound of formula (Ib) is represented by formula (Iba);

[0143]

[0144] Among them, R 1 、R 2 , Q, Y, n and m are the same as defined above.

[0145] In a preferred embodiment, the compound of formula (Ib) is represented by formula (Ibb);

[0146]

[0147] Among them, R 1 、R 2 , Q, Y, n and m are the same as defined above.

[0148] In a preferred embodiment, the compound of formula (Ib) is composed of formula (Ia-Q 1a )express:

[0149]

[0150] Among them, R 1 、R 2 、R 3 , Y and m are the same as defined above.

[0151] In a preferred embodiment, in particular; the compound of formula (I) is selected from 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyridin -2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(6-(3,5-dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 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; 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; 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; 5-(ethylsulfonyl)-N-(4-(trifluoromethoxy)phenyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; 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; 7-(5-bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 7-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 7-(5-(3,5-dichlorophenyl)-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 7-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-phenylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine;5-(3-(ethylsulfonyl)-6-(4-fluorophenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 4-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)benzonitrile; 5-(3-(ethylsulfonyl)-6-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(6-(4-chlorophenyl)-3-(ethylsulfonyl)- 5-(3-(ethylsulfonyl)-6-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(3-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 3-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)benzonitrile; 5-(5-bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine ; 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; 5-(6-(3-chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 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; 5-(3-(ethylsulfonyl)-6-(4-(1,1 ,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 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; 5-(5-(ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine;5-(3-(Ethylthio)-5-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 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; 5-(3-(ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine Oxalo[1,5-a]pyrimidine; 6-(6-chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(ethylsulfonyl)-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine ; 6-(3-(ethylsulfanyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine pyrimidine; 6-(3-(ethylsulfonyl)-6-(4-fluoro-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(6-(4-bromo-1H-imidazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(6-(4-chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine;6-(6-(3,5-dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 4-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)pyridin-2-yl)benzonitrile; 6-(3-(ethylsulfonyl)-6-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine 1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(3-methyl-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(6-(3-bromo-1H-1,2,4-triazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine oxazolo[1,5-a]pyrimidine; 6-(6-(4-chloro-1H-pyrazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(1-methyl-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4 ]triazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(6-chloro-5-(ethylthio)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylthio)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine;5-(6-chloro-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(1H-1,2,3-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylthio)-5-(1-methyl-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(5-(ethylsulfonyl)- )-6-(4-(trifluoromethoxy)phenyl)pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(3-methyl-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(4-fluoro-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(1-methyl-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5 -a]pyrimidine; 5-(5-(ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 2-(3-(ethylsulfonyl)-5-(2-(trifluoromethyl)pyrazolo[ 1,5-a]pyrimidine; 5-(5-(3,5-dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(3,5-dichlorophenyl)-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine;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; 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; 6-(6-chloro-5-(ethylthio)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; (5-bromo-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine) -5-yl)pyridin-3-yl)(ethyl)(imino)-16-sulfoxide (sulfanone); 5-(5-(ethylsulfonyl)-6-(3-methyl-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; ((5-(ethylthio)-6 -(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)dimethyl-16-sulfoxide; ((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)dimethyl-16-sulfoxide; 6-(5-(ethylsulfonyl)-6-(3-methyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)imidazo[1,2-a]pyrimidine; 5-(5-(4-bromo-1H-pyrazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-( 5-(4-chloro-1H-pyrazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-bromo-3-(ethylsulfanyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 6-(5-bromo-3-(ethylsulfanyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(5-bromo-3-(ethylsulfanyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(6-chloro-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine;5-(3-(ethylsulfonyl)-5-(4-fluorophenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(pyrimidin-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; ethyl(imino)(5-(4-(trifluoromethoxy) )phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-16-sulfoxide; 5-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(5-(4-chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(5-(3,5-dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine )pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(5-(3,5-difluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(4-fluorophenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; ((5-(ethylsulfonyl)-6-( 2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)dimethyl-16-sulfoxide; diethyl((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)-16-sulfoxide; ethyl((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)(methyl)-16-sulfoxide; 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-ol;6-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(3-chloro-5-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 2-(5-bromo-3-(ethylsulfanyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 6-(3-(ethylsulfonyl)-5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridin-2 -yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; diethyl((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)-16-sulfoxide; ethyl((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)(methyl)-16-sulfoxide; 2-(3-(ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(3-(ethylsulfonyl)-5-(4-fluorophenyl)pyridin-2-yl)-9-methyl-8-( 2-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(3-(ethylsulfonyl)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 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; 2-(3-(ethylsulfonyl)-5-(1-methyl-3-(trifluoromethyl)-1H-pyrazolo- 2-(5-(3,5-difluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(5-(4-chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(5-(4-chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 5-(5-(3,5-difluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine;5-(5-(4-chloro-3-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(3-chloro-4-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 2-(5-(3,5-dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(3-(ethylsulfonyl)-5-(3-methyl-1H- 1,2,4-triazol-1-yl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(5-(3-chloro-5-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)thiazole; 5-(3-(ethylsulfonyl)-5-(1-methyl-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 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; 5-(3-(ethylsulfonyl)-5-(pyrimidin-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(5-cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(6-(3-chloro-5-fluorophenyl)-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine [1,5-a]pyrimidin-5-yl)nicotinonitrile; diethyl ((5-(ethylsulfonyl)-6-(9-methyl-8-(trifluoromethyl)-9H-purin-2-yl)pyridin-3-yl)imino)-16-sulfoxide; 5-(3-(ethylsulfonyl)-6-(3-fluoro-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; N-cyclopropyl-5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; 5-(5-cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine;5-(3-(ethylsulfonyl)-5-(2-methoxypyrimidin-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(3-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 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; 5-(3-(ethylsulfonyl)-5-(1H- 1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 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; 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; ((5-(ethylsulfonyl)-6-(9-methyl-8-(trifluoromethyl)-9H -purin-2-yl)pyridin-3-yl)imino)dimethyl-16-sulfoxide; 5-(ethylsulfonyl)-6-(9-methyl-8-(trifluoromethyl)-9H-purin-2-yl)pyridin-3-ol; 5-(3-(ethylsulfonyl)-5-methylpyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 6-(5-(ethyl pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(3,4-dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 2-(3-(ethylsulfonyl)-5-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine;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; 5-(6-chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(cyclopropylmethoxy)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(5-(4-chloro-3-fluorophenyl)-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(5-(3,4-dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-methylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(6-chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(ethylsulfonyl)-N,N-dimethyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-5 -yl)pyridin-2-amine; 5-(ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; N-cyclopropyl-5-(ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; N-cyclopropyl-5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine; 5-(6-cyclopropyl-3-(ethylsulfonyl)pyridin-2- ((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-sulfoxide; 5-(3-(ethylsulfonyl)-6-(prop-1-yn-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; N-cyclopropyl-5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine;N-cyclopropyl-5-(ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; 5-(5-(3-bromo-1H-1,2,4-triazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(prop-1-yn-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; ((5-(ethylthio)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-imino Sulfone; 5-(6-cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-methylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-methylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-methylpyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; ((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a ]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-sulfoxide; ((5-(ethylthio)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-sulfoxide; ethyl ((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)(methyl)-16-sulfoxide; 5-(3-(ethylthio)-6-methylpyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(6-cyclopropyl-3-(ethylthio)pyridin-2-yl) 1,5-a]pyrimidine; 5-(5-cyclopropyl-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylthio)-5-(4-fluorophenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylthio)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; ethyl(5-(4-fluorophenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(imino)-16-sulfoxide;Ethyl(imino)(5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-16-sulfoxide; (6-chloro-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(ethyl)(imino)-16-sulfoxide; 5-(3-(ethylsulfonyl)-6-(methylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(methylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-( (5-((dimethyl)oxy)-16-imino)amino)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(ethyl)(imino)-16-sulfoxide; (5-((dimethyl)oxy)-16-imino)amino)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(ethyl)(imino)-16-sulfoxide; (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)(imino) (Methyl)-16-sulfoxide; 5-(3-(ethylsulfonyl)-5-(2-methylprop-1-en-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; ethyl(imino)(5-(2-methylprop-1-en-1-yl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-16-sulfoxide; ethyl(imino)(5-(3-(trifluoromethyl)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-16-sulfoxide; 5-(3-(ethylsulfonyl)-5-(prop-1-en-2-yl)pyridin-2-yl) -2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(2-cyclopropylvinyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; N-((5-((dimethyl)oxo)-16-imino)amino)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(ethyl)(oxo)-16-imino)cyanamide; N-(ethyl)oxo)(5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-16-imino)cyanamide;N-(Ethyl)5-(4-fluorophenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(oxo)-16-sulfenyl)cyanamide; 5-(6-ethyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(2-methylprop-1-en-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-ethyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-vinylpyridine-2 -yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-cyclobutyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; tert-butyl 2-cyano-2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetate; 5-(3-(ethylsulfonyl)-6-(prop-1-en-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; (E)-5-(6-(2-cyclopropylvinyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine a]pyrimidine; 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetonitrile; 5-(ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine; 2-(5-(ethylthio)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)acetonitrile; 2-((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)oxy)-2-methylpropanamide; 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl) tert-Butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)carbamate; tert-butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)carbamate; tert-butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine; tert-butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(methyl)carbamate; N-(tert-butyl)-2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetamide;5-(3-(ethylsulfonyl)-6-methoxypyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(6-ethoxy-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(6-cyclobutyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(difluoromethoxy)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(ethylsulfonyl)-N,N-dimethyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridine -3-amine; 5-(3-(ethylsulfonyl)-5-(pyrimidin-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)acetonitrile; N-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)cyclopropanecarboxamide; 1-((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)hexahydro-1,6-thiopyran 1-oxide; 1-((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)hexahydro-1,6-thiopyran 1-oxide; 1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)-1,6-thietane 1-oxide; 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-ol; 5-(3-(ethylsulfonyl)-6-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-isopropylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(2,2,2-trifluoroethoxy)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-isopropoxypyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(ethylsulfonyl)-N-isopropyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; N-(cyclopropylmethyl)-5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; 5-(3-(ethylsulfonyl)-6-(thietan-3-yloxy)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine;5-(Ethylsulfonyl)-N-propyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; 1-((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)-116-thietane 1-oxide; N-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)cyclopropanecarboxamide; 1-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)cyclopropane-1-carbonitrile; N-(5-(ethylsulfonyl)- )-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-N-methylacetamide; 1-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)urea; 1-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-1,3-dimethylurea; 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-2-methylpropionitrile; 5-(3-(ethylsulfonyl)-5-(trifluoromethyl)pyridin-2-yl)-2-(trifluoromethyl)pyridin-2-yl)- (5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridineamide; (5-(Ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridineamide; (5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinate; (5-(Ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinate;) -3-yl)methanone; (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(morpholinyl)methanone; N-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)cyclopropanesulfonamide; N-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-N-methylcyclopropanesulfonamide; N-((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)(methyl)(oxo)-16-thiocyanamide;Ethyl(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)((trifluoromethyl)imino)-16-sulfoxide; 2-((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)oxy)-2-methylpropionitrile; 5-(3-(ethylsulfonyl)-5-(pyridin-2-yloxy)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(2,2-difluorocyclopropyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine pyrimidine; tert-butyl 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)hydrazine-1-carboxylate; 1-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)ethan-1-one; N-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-O-methylhydroxylamine and 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-1,1,1-trifluoropropan-2-ol.

[0152] The compounds of the present invention may exist as one or more stereoisomers. Various stereoisomers include enantiomers, diastereomers, atropisomers, and geometric isomers. It will be understood by those skilled in the art that one stereoisomer may be more active and / or may exhibit beneficial effects when enriched relative to other stereoisomers or separated from other stereoisomers. In addition, those skilled in the art know how to separate, enrich, and / or selectively prepare the stereoisomers. The compounds of the present invention may exist as mixtures of stereoisomers, individual stereoisomers, or optically active forms.

[0153] In the case where the compound of formula (I) is a cation or can form a cation, the anion portion of the salt can be inorganic or organic. Alternatively, in the case where the compound of formula (I) is an anion or can form an anion, the cationic portion of the salt can be inorganic or organic. Examples of the inorganic anion portion of the salt include, but are not limited to, chloride, bromide, iodide, fluoride, sulfate, phosphate, nitrate, nitrite, bicarbonate, and bisulfate. Examples of the organic anion portion 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 sulfonate, aryl disulfonate, alkyl phosphonate, aryl phosphonate, aryl diphosphonate, p-toluenesulfonate, and salicylate. Examples of the inorganic cation portion of the salt include, but are not limited to, alkali metals and alkaline earth metals. Examples of the organic cation portion of the salt include, but are not limited to, pyridine, methylamine, imidazole, benzimidazole, histidine, phosphazene, tetramethylammonium, tetrabutylammonium, choline, and trimethylamine.

[0154] The metal ions in the metal complexes of the compounds of formula (I) are in particular ions of the following elements: elements of the second main group, in particular calcium and magnesium, elements of the third and fourth main groups, in particular aluminum, tin and lead, and elements of the first to eighth transition groups, in particular chromium, manganese, iron, cobalt, nickel, copper, zinc, etc. Particular preference is given to metal ions of elements of the fourth period and of the first to eighth transition groups. The metals may be present in any valence they can assume.

[0155] In one embodiment, the present invention provides a compound of formula (I), an agriculturally acceptable salt thereof, a metal complex, a structural isomer, a stereoisomer, a diastereomer, an enantiomer, a chiral isomer, a rotational isomer, a conformational isomer, a rotational isomer, a tautomer, an optical isomer, a polymorph, a geometric isomer or an N-oxide thereof, and compositions thereof with an excipient, an inert carrier or any other necessary ingredients, such as surfactants, additives, solid diluents and liquid diluents.

[0156] The compound of formula (I) (including all stereoisomers, N-oxides and salts thereof) generally exists in more than one form, and thus formula (I) includes all crystalline and non-crystalline forms of the compound represented by formula (I). Non-crystalline forms include embodiments that are solids (e.g., waxes and colloids) and embodiments that are liquids (e.g., solutions and melts). Crystalline forms include embodiments that essentially represent single crystal forms and embodiments that represent mixtures of polymorphs (i.e., different crystalline forms). The term "polymorph" refers to a specific crystalline form of a chemical compound that can crystallize in different crystalline forms, which have different molecular arrangements and / or conformations in the crystal lattice. Although polymorphs can have the same chemical composition, their composition may also be different due to the presence or absence of co-crystallized water or other molecules that can be weakly or strongly bound to the crystal lattice. The chemical, physical and biological properties of polymorphs, such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspension, dissolution rate and bioavailability, may be different. Those skilled in the art will appreciate that one polymorph of a compound represented by formula (I) may exhibit beneficial effects (e.g., suitability for preparing useful formulations, improved biological properties) relative to another polymorph or 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) may be achieved by methods known to those skilled in the art, for example, including crystallization using a selected solvent and temperature.

[0157] In one embodiment, the present invention provides a method for preparing a compound of formula (I) or an agriculturally acceptable salt thereof.

[0158] The compounds of the present invention defined in formula (I) and / or Table (I) can be prepared in a known manner in a variety of ways as described in Schemes 1-2. The compounds of the present invention can be prepared as shown in the following schemes, wherein, unless otherwise indicated, each variable is defined as above for the compounds of formula (I).

[0159] According to a feature of the present invention, compounds of general formula (I) (wherein all symbols are as defined above) can be prepared by the methods given in Scheme 1 and Scheme 2 or in the Examples. Representative steps are shown below; however, this disclosure should not be interpreted as limiting the scope of the invention to obtain compounds of formula (1) as described below.

[0160]

[0161] According to Scheme 1, the present invention provides a process for preparing compounds of formula (I) starting from an appropriate halide or triflate of formula (2), wherein Q is as defined above.

[0162] The compound of formula (2) can be coupled with a boronic acid or boric acid ester compound of formula (3) under standard Suzuki cross-coupling conditions to obtain a compound of formula (I). In a suitable solvent (such as tetrahydrofuran (THF), N,N'-dimethylformamide (DMF), 1,2-dimethoxyethane, 1,4-dioxane), or a solvent system (such as a mixture of tetrahydrofuran (THF) / water, 1,2-dimethoxyethane / water, 1,4-dioxane / water), the Suzuki cross-coupling reaction can be catalyzed by a palladium-based catalyst, including but not limited to 1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) or tetrakis(triphenylphosphine)palladium(0). The reaction is usually carried out in the presence of a base (such as potassium carbonate, cesium carbonate or potassium phosphate). As described in the literature (e.g., see Chem. Soc. Rev. 2014, 43, 412-443) or in WO2014070978, the reaction temperature may preferably be from ambient temperature (80°C) to the boiling point of the reaction mixture, or microwave irradiation at a temperature of 70°C to 150°C to prepare the compound of formula (I).

[0163] Alternatively, the compound of formula (I) can be coupled with a heteroaryl tin compound of formula (3) in a suitable solvent (e.g., acetonitrile, tetrahydrofuran (THF), N,N'-dimethylformamide (DMF), 1,2-dimethoxyethane, 1,4-dioxane) in the presence of a base such as an alkali metal hydride, an alkali metal carbonate and an organic base, in the presence of a catalyst such as bis(triphenylphosphine)palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) chloride, tris(dibenzylideneacetone)dipalladium(0) and palladium(II) acetate; a nickel catalyst such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride; and a copper catalyst such as copper(I) iodide and copper(I) chloride, at a temperature between room temperature and the reflux temperature of the solvent, or under microwave irradiation at a temperature between 70°C and 150°C. Ligands and / or inorganic halogenated compounds can be added to the reaction as needed. Examples of ligands used in the reaction include triphenylphosphine, Xantphos, 2,2'-bis(diphenylphosphine)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-(dicyclohexylphosphine)-2',4',6'-triisopropyl-1,1'-biphenyl, 2-aminoethanol, 8-hydroxyquinoline, and 1,10-phenanthroline. Examples of inorganic halogenated compounds include alkali metal fluorides such as potassium fluoride and sodium fluoride; and alkali metal halides such as lithium chloride, sodium chloride, and sodium chloride.

[0164]

[0165] Scheme 2 describes the preparation of stannanes of general formula (3) by reacting an appropriate halide or triflate of a compound of formula (4) with a reagent such as hexamethyltin disulfonate or triethyl chloride in a suitable solvent such as N,N'-dimethylformamide (DMF) or a mixture of two or more suitable solvents in the presence of a base such as potassium carbonate and in the presence of a catalyst such as tetrakis(triphenylphosphine)palladium(0) at a temperature of 25°C to the reflux temperature of the solvent or under microwave irradiation at a temperature of 70°C to 160°C.

[0166] Alternatively, compounds of general formula (3) can be obtained from compounds of formula (4) by reacting with a reagent such as n-butyllithium in a suitable aprotic solvent such as tetrahydrofuran (THF) at a temperature of -100°C to 25°C, followed by reacting with a reagent such as hexamethylditin or triethyltin chloride in a suitable aprotic solvent such as tetrahydrofuran (THF) at a temperature of -100°C to 50°C.

[0167] In one embodiment, the present invention provides a composition for controlling or preventing invertebrate pests. The composition comprises a biologically effective amount of a compound of formula (I) or 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 a surfactant and an adjuvant.

[0168] In another embodiment, the composition additionally 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.

[0169] In another embodiment, the present invention provides agrochemical compositions of conventional types such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, compressed formulations, capsules, and mixtures thereof. Examples of composition types include suspensions (e.g., SC, OD, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), pastes, lozenges, wettable powders or dusts (e.g., WP, SP, WS, DP, DS), compressed formulations (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticides (e.g., LN), and gel formulations (e.g., GF) for treating plant propagation materials such as seeds. These and other composition types are described in "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6 th Defined in Ed. May 2008, CropLife International.

[0170] The compositions are prepared in a known manner, for example as described in Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or in Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T and F Informa, London, 2005.

[0171] Examples of suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, wetting agents, insect repellents, attractants, feeding stimulants, extenders, bactericides, antifreeze agents, defoamers, colorants, tackifiers or adhesives.

[0172] Suitable solvents and liquid carriers are water and organic solvents, for example medium to high boiling point mineral oil fractions, such as kerosene, diesel; vegetable or animal oils; aliphatic, cyclic and aromatic hydrocarbons, for example, toluene, paraffin, tetralin, alkylated naphthalenes; alcohols, for example, ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; dimethyl sulfoxide; ketones, for example, cyclohexanone; esters, for example, lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, for example, N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

[0173] Suitable solid carriers or fillers are mineral earths, for example silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, for example cellulose, starch; fertilizers, for example ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; products of plant origin, for example cereal flour, bark flour, wood flour, nut shell flour, and mixtures thereof.

[0174] Suitable surfactants are surface-active compounds such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. These surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, 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).

[0175] Suitable anionic surfactants are alkali metal salts, alkaline earth metal salts or ammonium salts of sulfonic acid, sulfuric acid, phosphoric acid, carboxylic acid and mixtures thereof. Examples of sulfonates are alkyl aryl sulfonates, diphenyl sulfonates, α-olefin sulfonates, lignin sulfonates, fatty acids and oily sulfonates, ethoxylated alkylphenol sulfonates, alkoxylated arylphenol sulfonates, condensed naphthalene sulfonates, dodecyl- and tridecylbenzene sulfonates, naphthalene and alkylnaphthalene sulfonates, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oily sulfates, ethoxylated alkylphenol sulfates, 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 alcohols or alkylphenol ethoxylates.

[0176] 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 that have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide can be used for the alkoxylation, with ethylene oxide being preferred. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerides, 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.

[0177] Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are AB or ABA type block polymers comprising polyethylene oxide and polypropylene oxide blocks, or ABC type block polymers comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polyalkalis. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers. Examples of polyalkalis are polyvinylamines or polyethyleneamines.

[0178] Suitable adjuvants are compounds that themselves have negligible 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 adjuvants. Further examples are listed in Knowles, Adjuvants and additives, Agrow Reports DS256, T and F Informa UK, 2006, Chapter 5.

[0179] Suitable thickening agents 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 alkylisothiazolinone and benzisothiazolinone. Suitable antifreeze agents are ethylene glycol, propylene glycol, urea, and glycerol. Suitable defoamers are organosilicon, long-chain alcohols, and soaps. Suitable colorants (e.g., red, blue, or green) are low water-soluble pigments and water-soluble dyes. Examples are inorganic colorants (e.g., iron oxide, titanium oxide, hexacyanoferrate) and organic colorants (e.g., alizarin, azo, and phthalocyanine colorants). Suitable tackifiers or adhesives are polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological or synthetic waxes, and cellulose ethers.

[0180] Examples of composition types and their preparation are as follows:

[0181] i) Water-soluble concentrates (SL, LS)

[0182] 10-60% by weight of compound (I) or its N-oxide or salt and 5-15% by weight of a wetting agent (eg alcohol alkoxylate) are dissolved in up to 100% by weight of water and / or a water-miscible solvent (eg alcohol). The active substance dissolves on dilution with water.

[0183] ii) Dispersible Concentrates (DC)

[0184] 5-25 wt% of compound (I) or its N-oxide or salt and 1-10 wt% of a dispersant (eg polyvinylpyrrolidone) are dissolved in up to 100 wt% of an organic solvent (eg cyclohexanone), and diluted with water to obtain a dispersion.

[0185] iii) Emulsifiable concentrate (EC)

[0186] 15-70 wt% of compound (I) or its N-oxide or salt and 5-10 wt% of an emulsifier (such as calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in up to 100 wt% of a water-insoluble organic solvent (such as aromatic hydrocarbons), and diluted with water to obtain an emulsion.

[0187] iv) Emulsion (EW, EO, ES)

[0188] 5-40 wt% of compound (I) or its N-oxide or salt and 1-10 wt% of an emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% of a water-insoluble organic solvent (e.g., aromatic hydrocarbon). This mixture is added to up to 100 wt% of water using an emulsifier to form a homogeneous emulsion. The emulsion is then diluted with water to obtain an emulsion.

[0189] v) Suspension (SC, OD, FS)

[0190] In a stirred ball mill, 20-60% by weight of compound (I) or its N-oxide or salt is ground with 2-10% by weight of a dispersant and wetting agent (e.g. sodium lignin sulfonate and alcohol ethoxylate), 0.1-2% by weight of a thickener (e.g. xanthan gum) and up to 100% by weight of water to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance. For FS-type compositions, a maximum of 40% by weight of a binder (e.g. polyvinyl alcohol) is added.

[0191] vi) Water-dispersible granules and water-soluble granules (WG, SG)

[0192] 50-80% by weight of compound (I) or its N-oxide or salt is added to up to 100% by weight of a dispersant and wetting agent (e.g. sodium lignin sulfonate and alcohol ethoxylate), finely ground together and prepared into water-dispersible or water-soluble granules using a technical device (e.g. extruder, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.

[0193] vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

[0194] In a rotor-stator mill, 50-80% by weight of compound (I) or its N-oxide or salt is ground with 1-5% by weight of a dispersant (e.g. sodium ligninsulfonate), 1-3% by weight of a wetting agent (e.g. alcohol ethoxylate) and up to 100% by weight of a solid carrier (e.g. silica gel). Dilution with water gives a stable dispersion or solution of the active substance.

[0195] viii) Gel (GW, GF)

[0196] In a stirred ball mill, 5-25% by weight of compound (I) or its N-oxide or salt is added to 3-10% by weight of a dispersant (e.g. sodium lignin sulfonate), 1-5% by weight of a thickener (e.g. carboxymethyl cellulose) and up to 100% by weight of water and ground together to obtain a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

[0197] ix) Microemulsion (ME)

[0198] 5-20 wt% of compound (I) or its N-oxide or salt is added to 5-30 wt% of an organic solvent mixture (e.g., fatty acid diformamide and cyclohexanone), 10-25 wt% of a surfactant mixture (e.g., alcohol ethoxylate and arylphenol ethoxylate) and up to 100% of water. The mixture is stirred for 1 hour to spontaneously generate a thermodynamically stable microemulsion.

[0199] x) Microcapsules (CS)

[0200] An oil phase containing 5-50 wt% of compound (I) or its N-oxide or salt, 0-40 wt% of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and 2-15 wt% of acrylic monomers (e.g., methyl methacrylate, methacrylic acid, and di- or triacrylates) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Free radical polymerization initiated by a free radical initiator results in the formation of poly(methyl acrylate) microcapsules. Alternatively, an oil phase containing 5-50 wt% of compound I according to the present invention, 0-40 wt% of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and an isocyanate monomer (e.g., diphenylmethane-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Addition of a polyamine (e.g., hexamethylenediamine) results in the formation of polyurea microcapsules. The monomer amount is 1-10 wt%. The wt% is related to the total CS composition.

[0201] xi) Powders (DP, DS)

[0202] 1-10% by weight of compound (I) or its N-oxide or salt is finely ground and mixed with up to 100% by weight of a solid carrier (eg finely divided kaolin).

[0203] xii) Granules (GR, FG)

[0204] 0.5-30% by weight of compound (I) or its N-oxide or salt is finely ground and combined with up to 100% by weight of a solid carrier (eg a silicate). Granulation is achieved by extrusion, spray drying or fluidized bed.

[0205] xiii) Ultra-low volume liquid (UL)

[0206] 1-50% by weight of Compound (I) or its N-oxide or salt is dissolved in up to 100% of an organic solvent (eg an aromatic hydrocarbon).

[0207] Composition types i) to xiii) may optionally comprise further auxiliaries, for example 0.1-1% by weight of bactericides, 5-15% by weight of antifreeze agents, 0.1-1% by weight of antifoams and 0.1-1% by weight of colorants.

[0208] In another embodiment of the present invention, an agrochemical composition of a compound of formula (I) is provided, comprising 0.01-95% by weight of an active substance, preferably 0.1-90% by weight, more preferably 1-70% by weight, in particular 10-60% by weight of an active substance. The active substance is used in a purity (according to NMR spectroscopy) of 90% to 100%, preferably 95% to 100%.

[0209] 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 typically used to treat plant propagation materials, especially seeds. After dilution 2-10 times, the active ingredient concentration in the ready-to-use formulation is 0.01 to 60% by weight, preferably 0.1 to 40% by weight. Application can be carried out before or during sowing.

[0210] Formula (I) compound and composition thereof are applied respectively or are processed to plant propagation material, especially the method on seed comprises seed dressing, coating, granulation, dusting, soaking and in-furrow application method of propagation material.Preferably, formula (I) compound or its composition are respectively passed through the method that does not induce germination, for example, by seed dressing, granulation, coating and dusting, are applied to plant propagation material.

[0211] When used in plant protection, the active substance is applied in an amount of 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, in particular 0.1 to 0.75 kg per hectare, depending on the desired effect.

[0212] When treating plant propagation material such as seeds, for example by dusting, coating or soaking the seeds, amounts of active substance of 0.1 to 1000 g, preferably 1 to 1000 g, more preferably 1 to 100 g and most preferably 5 to 100 g per 100 kg of plant propagation material, preferably seeds, are generally required.

[0213] When used to protect materials or stored products, the amount of active substance used depends on the type of application area and the desired effect. In the protection of materials, the application rate is usually 0.001g to 2kg, preferably 0.005g to 1kg of active substance per cubic meter of treated material.

[0214] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients and other pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) can be added to the active substance or a composition comprising them as a premix, or, if appropriate, added just before use (tank mix). 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.

[0215] The user can usually apply the composition according to the present invention using a pre-dosed device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Typically, the agrochemical composition is adjusted to the desired application concentration with water, a buffer, and / or other adjuvants to obtain a ready-to-use spray liquid or an agrochemical composition according to the present invention. Typically, 20 to 6000 liters, preferably 35 to 1000 liters, and more preferably 50 to 500 liters of ready-to-use spray liquid are applied per hectare of agriculturally useful area.

[0216] According to one embodiment, the individual components of the composition according to the invention, for example as part of a kit or as part of a binary or ternary mixture, can be mixed by the user himself in a spray tank and, if appropriate, further auxiliaries can be added.

[0217] Thus, the compounds and compositions of the present invention are useful agronomically for protecting field crops from herbivorous invertebrate pests and non-agronomically for protecting other horticultural crops and plants from herbivorous invertebrate pests. This utility includes protecting crops and other plants (i.e., agronomic and non-agronomic) that contain genetic material introduced by genetic engineering (i.e., transgenic) or modified by mutagenesis to provide advantageous traits.

[0218] The compounds of the present invention are characterized by favorable metabolism and / or soil residue patterns and exhibit activity against a range of agronomic and non-agronomic invertebrate pests. In the field of pest control, the compounds of the present invention are active ingredients with preventive and / or therapeutic value, and can be used against insecticide-resistant pests, such as insects and mites, even at low application rates, and are well tolerated by warm-blooded species, fish, and plants.

[0219] In the context of the present invention, "invertebrate pest control" refers to the inhibition of invertebrate pest development (including mortality) that results in a significant reduction in pest feeding or other injury or damage caused by the pest; (related expressions are similarly defined.) As used herein, the term "invertebrate pests" includes arthropods, gastropods, and nematodes that are economically important as pests. The term "arthropod" includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs, and symphylans.

[0220] The term "gastropods" includes snails, slugs, and other stalked oviraptors. The term "nematodes" includes all helminths, such as roundworms, heartworms, and herbivorous nematodes (Nematoda), flukes (Tematoda), acanthocephalians, and tapeworms (Cestoda). Those skilled in the art will recognize that not all compounds are equally effective against all pests.

[0221] The compounds of the present invention exhibit activity against economically important agronomic pests in forests, greenhouses, nurseries, ornamentals, turfgrasses, food and fiber, public and animal health, domestic and commercial buildings, household and stored product pests. These include larvae of the Lepidoptera, such as armyworms, cutworms, loopers and heliothines of the family Noctuidae (e.g., Spodoptera fugiperda JESmith, Spodoptera exigua Hubner, Agrotis ipsilon Hufnagel, Trichoplusia ni Hubner, Heliothis virescens Fabricius); borers, casebearers, webworms, coneworms, cabbageworms and skeletonizers of the family Pyralidae (e.g., Ostrinia nubilalis Hubner, Amyelois transitella Walker), Crambus caliginosellus Clemens, Herpetogramma licarsisalis Walker); leafrollers, budworms, seedworms, and fruit worms of the family Tortricidae (e.g., Cydia pomonella Linnaeus, Endopiza viteana Clemens, Grapholita molesta Busck); and many other economically important Lepidoptera pests (e.g., Plutella xylostella Linnaeus, Pectinophora gossypiella Saunders, Lymantria dispar, and Lymantria dispar). Linnaeus); nymphs and adults of the order Blattodea, including cockroaches of the families Blattellidae and Blattidae (e.g.,oriental cockroach (Blatta orientalis Linnaeus), Asian cockroach (Blatellaasahinai Mizukubo), German cockroach (Blattella gemnanica Linnaeus), brown cockroach (Supellalongipalpa Fabricius), American cockroach (Periplaneta americana Linnaeus), brown cockroach (Periplaneta brunnea Burmeister), Madeira cockroach (Leucophaea maderae Fabricius)); leaf-feeding larvae and adults of the order Coleoptera, including weevils of the families Anthribidae, Bruchidae, and Curculionidae (e.g., Anthonomus grandis Boheman, Lissorhoptrus oryzophilus Kuschel, Sitophilus granarius Linnaeus, Sitophilus oryzae Linnaeus); flea beetles, cucumber beetles, rootworms, leaf beetles, potato beetles, and leafminers of the Chrysomelidae family (e.g., Colorado potato beetle (Leptinotarsa ​​dece mLineata Say), western corn rootworm (Diabrotica virgifera virgifera LeConte); chafers and other beetles of the Scarabeidae family (e.g., Japanese beetle (Popillia japonica Newman) and European chafer (Rhizotrogus majalis Razoumowsky); carpet beetles of the Dermestidae family (e.g., carpet beetles (Dermatidae)). beetles; wireworms of the family Elateridae; bark beetles of the family Scolytidae and flour beetles of the family Tenebrionidae. In addition, it also includes: adults and larvae of the order Dermaptera,Included are earwigs of the family Forficulidae (e.g., Forficula auricularia Linnaeus, Chelisoches mono Fabricius); adults and nymphs of the orders Hemiptera and Homoptera, for example, plantbugs of the family Miridae, cicadas of the family Cicadidae, leafhoppers of the family Cicadellidae (e.g., Empoasca spp.), planthoppers of the families Fulgoroidae and Delphacidae, treehoppers of the family Membracidae, psyllids of the family Psyllidae, whiteflies of the family Aleyrodidae, aphids of the family Aphididae, phylloxera of the family Phylloxeridae, mealybugs of the family Pseudococcidae, scales of the families Coccidae, Diaspididae, and Margarodidae, lace bugs of the family Tingidae, stink bugs of the family Pentatomidae, and other seed bugs of the family Lygaeidae, spittlebugs of the family Cercopidae, squash bugs of the family Coreidae, and red bugs and cotton stainers of the family Pyrrhocoridae. Also included are the adults and larvae of the Acari (mites) pests, such as spidermites and red mites of the family Tetranychidae (e.g., Panonychus ulmi Koch, Tetranychus urticae Koch, Tetranychus mcdanieli McGregor),Flat mites of the family Tenuipalpidae (e.g., Brevipalpus lewisi McGregor), rust mites and bud mites of the family Eriophyidae, and other leaf-feeding mites and mites that are essential for human and animal health, i.e., dust mites of the family Epidermoptidae, follicle mites of the family Demodicidae, grain mites of the family Glycyphagidae, ticks of the order Ixodidae (e.g., Ixodes scapularis Say, Ixodes holocyclus Neumann, Dermacentor variabilis Say), lone star tick (Amblyomma americanum Linnaeus), and scab mites and itch mites of the families Psoroptidae, Pyemotidae, and Sarcoptidae; adults and immatures of the order Orthoptera, including grasshoppers, locusts, and crickets (e.g., migratory grasshoppers (e.g., Melanoplus sanguinipes Fabricius, M. differentialis Thomas), American grasshoppers (e.g., Schistocerca americana Drury), desert locusts (Schistocerca gregaria Forskal), migratory locusts (Locusta migratoria Linnaeus), house crickets (Acheta domesticus Linnaeus), mole crickets (Gryllotalpa spp.)); adults and immatures of the order 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.,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 pests, mosquitoes (e.g., Aedes spp., Anopheles spp., Culex spp.), black flies (e.g., Prosimulium spp., Simulium spp.), biting midges, sandflies, sciarids and other Nematocera pests; adults and immatures of the order Thysanoptera, including onion thrips (Thrips tabaci Lindeman) and other leaf-feeding thrips; insect pests of the order Hymenoptera, including ants (e.g.,Red carpenter ants (Camponotusferrugineus Fabricius), black carpenter ants (Camponotus pennsylvanicus De Geer), pharaoh ants (Monomorium pharaonis Linnaeus), small fire ants (Wasmannia auropunctata Roger), fire ants (Solenopsis geminata Fabricius), invasive fire ants (Solenopsis invicta Buren), Argentine ants (Iridomyrmex humilis Mayr), crazy ants (Paratrechina longicornis Latreille), pavement ants (Tetramorium caespitum Linnaeus), cornfield ants (Lasius alienus Fδrster), smelly house ants (Tapinoma sessile Say), bees (including carpenter bees), hornets, yellowjackets, and wasps; insect pests of the order Isoptera, including the eastern subterranean termite (Reticulitermes flavipes) Kollar), western subterranean termite (Reticulitermes hesperus Banks), Formosan subterranean termite (Coptotermes formosanus Shiraki), West Indian drywood termite (Incisitermes immigrans Snyder), and other economically important termites; insect pests of the order Thysanura, for example, bark beetle (Lepisma saccharina Linnaeus) and firebrat (Thermobia domestica Packard); insect pests of the order Mallophaga,including human head louse (Pediculus humanus capitis DeGeer), human 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 urystemus Nitzsch), long-nosed cattle louse (Linognathus vituli Linnaeus) and other sucking and biting parasitic lice that attack humans and animals; insect pests of the order Siphonoptera, including oriental rat flea (Xenopsylla cheopis Rothschild), cat flea (Ctenocephalides felis Bouche), dog flea (Ctenocephatides canis Curtis), chicken flea (Ceratophyllus gallinae Schrank), sticktight flea (Echidnophagagallinacea Westwood), human flea (Pulex irritans Linnaeus), and other fleas that infest mammals and birds. Other arthropod pests covered include spiders of the order Araneae, such as the brown recluse spider (Loxosceles reclusa Gertsch and Mulaik) and the black widow spider (Latrodectus mactans Fabricius), centipedes of the order Scutigeromorpha, such as the house centipede (Scutigera coleoptrata Linnaeus). Also included are members of the classes Nematoda, Cestoda, Trematoda, and Acanthocephala.Included are economically important members of the orders Strongylida, Ascaridida, Oxyurida, Rhabditida, Spirurida, and Enoplida, such as, but not limited to, economically important agricultural pests (i.e., root knot nematodes of the genus Meloidogyne, lesion nematodes of the genus Pratylenchus, stubby root nematodes of the genus Trichodorus, etc.), as well as animal and human health pests (i.e., all economically important flukes, tapeworms, and roundworms, such as Strongylus vulgaris in horses, Toxocara canis in dogs, Haemonchus contortus in sheep, and Cynomolgus spp. in captivity). contortus in dogs, Dirofilaria immitis Leidy in dogs, Anoplocephala perfoliata in horses, Fasciola hepatica Linnaeus in ruminants, etc.

[0222] The compounds of the present invention are effective against pests of the order Lepidoptera (e.g., Alabama argillacea Hubner (cotton leaf worm), Archips argyrospila Walker (fruit tree leaf roller), A. rosana Linnaeus (European leaf roller) and other Archips species, Chilo suppressalis Walker (rice stem borer), Cnaphalocrosis medinalis Guenee (rice leaf roller), Crambus caliginosellus Clemens (corn root webworm), Crambus teterrellus Zincken (bluegrass webworm), Cydiapomonella Linnaeus (apple codling moth), Earias insulana Boisduval (spiny bollworm), Earias vittella Fabricius (spotted bollworm), Helicoveipa armigera (American bollworm), Helicoverpa zea Boddie (corn earworm), Heliothis virescens Fabricius (tobacco budworm), Herpetogramma licarsisalis Walker (sod webworm), Lobesia botrana Denis and (grape berry moth), Pectinophora gossypiella Saunders (pink bollworm), Phyllocnistis citrella Stainton (citrus leafminer), Pieris brassicae Linnaeus (large white butterfly), Pieris rapae Linnaeus (small white butterfly), Plutella xylostella Linnaeus (diamondback moth), Spodoptera exigua Hubner (beet armyworm), Spodoptera litura Fabricius (tobacco cutworm), cluster caterpillar), Spodoptera frugiperda JESmith (fall armyworm), Trichoplusia ni (cabbage looper) and Tula absoluta Meyrick (tomato leafminer)) showed particularly high activity.

[0223] The compounds of the invention also have commercially significant activity against members of the Homoptera order, including: Acyrthisiplionpisum Harris (pea aphid), Aphis craccivora Koch (cowpea aphid), Aphis fabae Scopoli (black bean aphid), Aphis gossypii Glover (cotton aphid, melon aphid), Aphis pomi De Geer (apple aphid), spiraecola Patch (spirea aphid), Aulacorthum solani Kaltenbach (foxglove aphid), Chaetosiphon fragaefolii Cockerell (strawberry aphid), Diuraphisnoxia Kurdjumov / Mordvilko (Russian wheat aphid), Dysaphis plantaginea Paaserini (rosy apple aphid), Eriosoma lanigerum Hausmann (woolly apple aphid), Hyalopterus pruni Geoffroy (mealy plum aphid), Lipaphiserysimi Kaltenbach (tarnip aphid), Metopolophium dirrhodum Walker (cereal aphid), Macrosipum euphorbiae Thomas (potato aphid), Myzus persicae Sulzer (peach-potato aphid, green peach aphid), Nasonoviaribisnigri Mosley (lettuce aphid), Pemphigus spp.) (root and gall aphids), Rhopalosiphummaidis Fitch (corn leaf aphid), Rhopalosiphumpadi Linnaeus (bird cherry-oataphid), Schizaphis graminum Rondani (greenbug), Sitobion avenae Fabricius (English grain aphid), Therioaphis maculata Buckton (spotted alfalfa aphid), Toxoptera aurantii, Boyer de Fonscolombe (black citrus aphid), and Toxoptera citiicida Kirkaldy (brown citrus aphid); Adelges spp.) (adelgids); Phylloxera devastatrix Pergande (pecan phylloxera); Bemisia tabaci Gennadius (tobacco whitefly, sweetpotato whitefly), Bemisia argentifolii Bellows and Perring (silverleaf whitefly), Dialeurodes citri Ashmead (silverleaf whitefly), and Trialeurodes vaporariorum Westwood (greenhouse whitefly); Empoasca fabae Harris (potato leafhopper), Laodelphax striatellus Fallen (smaller brown planthopper), Macrolestes quadrilineatus Forbes (purple leafhopper), Nephotettix cinticeps Uhler (greenleafhopper), Nephotettix nigropictus Stal (rice leafhopper), Nilaparvata lugens Stal (brown planthopper), Peregrinus maidis Ashmead (corn planthopper), Sogatellafurcifera Horvath (white-backed planthopper), Sogatodesorizicola Muir (rice delphacid), Typhlocyba pomaria McAfee (apple whiteleafhopper), Erythroneoura spp.(Grape leafhopper); Magicidada septendecim Linnaeus (periodic 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).

[0224] The compounds of the invention are also active against members of the Hemiptera order, including: Acrostemum hilareSay (green stink bug), Anasa tristis De Geer (pumpkin stink bug), Blissusleucopterus leucopterus Say (chinch bug), Corythuca gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), Dysdercus suturellus Herrich-S chaffer (cotton bug), Euchistus servus Say (brown stink bug), Euchistus variolrius Palisot deBeauvois (single-spotted stink bug), Graptósthetus spp. (complex of seed bugs), Leptoglossus corculus (complex of seed bugs), Say (leaf-footed pine seed bug), Lygus lineolaris Palisot de Beauvois (tarnished plant bug), Nezara viridula Linnaeus (southern green stink bug), Oebaluspugnax Fabricius (rice stink bug), Oncopeltus fasciatus DaEas (large milkweed bug), Pseudatomoscelis seriatus Reuter (cotton fleahopper).

[0225] Other insects controlled by the compounds of formula (I) of the present invention include: Thysanoptera (e.g., Frankliniella occidentalis Pergande (western flower thrips)), citriMoulton (citrus thrips), Sericothrips variabilis Beach (soybean thrips), and Thrips tabaciLindeman (onion thrips); and from the Coleoptera (for example, Leptinotarsa ​​dece mLineata Say (Colorado potato beetle), Epilachna varivestis Mulsant (Mexican bean beetle), and wireworms of the genera Agriotes, Athous, or Limonius).

[0226] In particular, the compounds of formula (I), their N-oxides, isomers, polymorphs and salts thereof are particularly suitable for effectively controlling the following pests: insects of the order 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 spp. 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, tomato stem moth (Keiferia lycopersicella), hemlock looper (Lambdina fiscellaria), beet armyworm (Laphygma exigua), LeucopteraCoffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Leucinodes orbonalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestrabrassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrus citrella), Pieris brassicae, Plathypenascabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scirpophaga incertulas, Scrophipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Spodoptera exigua, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, and Zeiraphera canadensis; and

[0227] Beetles (Coleoptera), for example, Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aphthonaeuphoridae, Athous haemorrhoidalis, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassidanebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Tobacco wireworm (Conoderus vespertinus), Crioceris asparagi, Click beetle (Ctenicera ssp.), Diabrotica longicornis, Diabrotica semipunctata, Cucumber leaf beetle (Diabrotica undecimpunctata), South American leaf beetle (Diabrotica speciosa), Corn root leaf beetle (Diabrotica virgifera), Mexican bean beetle (Epilachna varivestis), Tobacco flea beetle (Epitrix hirtipennis), Eutinobothrus brasiliensis, Pine bark beetle (Hylobius abietis), Hypera brunneipennis, Alfalfa leaf beetle (Hylobius postica), Spruce eight-toothed bark beetle (Ips typographus), Lema bilineata, Lemamelanopus, Potato beetle (Leptinotarsa ​​decemlineata) mLineata), beet beetle (Limonius californicus), rice water weevil (Lissorhoptrusoryzophilus), Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllobius pyri, Phyllotreta chrysocephala, Phyllophe sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitonalineatus, and Sitophilus granaria; flies and mosquitoes (Diptera), for example, Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrephaludens, 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, Contariniasorghicola), 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, Pegomyahysocyami, 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 spp. paludosa); 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; cockroaches (Blattaria Blattodea), for example, Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta fuliginosa and Periplaneta fuliginosa. australasiae) and Oriental cockroaches (Blattaorientalis; ants, bees, wasps, sawflies (Hymenoptera), for example, Athalia rosae, Atta cephalotes, Atta capiguara, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Lasius niger, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex californicus, Pheidole megacephala, Dasymutilla occidentalis, Bombus spp., Vespula squamosa, Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolichovespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile; crickets, grasshoppers, and locusts (Orthoptera), such as Acheta domestica, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, and Melanoplus truncatus. femurrubrum), Melanoplusmexicanus, Bloody Black Locust (Melanoplus sanguinipes), Rocky Mountain Locust (Melanoplus spretus), Red-winged Locust (Nomadacris)septemfasciata), South American Desert Locust (Schistocerca americana), Desert Locust (Schistocerca gregaria), Moroccan Halberd Locust (Dociostaurus maroccanus), Tachycinesasynamorus, Senegal Locust (Oedaleus senegalensis), Zonozerus variegatus, Hieroglyphus daganensis, Indian Cottonwood Locust (Kraussaria angulifera), Italian Locust (Calliptamus italicus), Australian Plague Locust (Chortoicetes terminifera), and Brown Migratory Locust (Locus tanapardalina); of the order Araneida, for example, the Black Widow Spider (Latrodectus mactans) and the Brown Recluse Spider (Loxosceles reclusa); and fleas (Siphonaptera), for example, Ctenocephalides felis, Ctenocephalides canis, and Ctenocephalides septemfasciata. canis), Xenopsyllacheopis, Pulex irritans, Tunga penetrans and Nosopsyllus fasciatus; silverfish, firebrat (Thysanura), for example Lepisma saccharina and Thermobia domestica; lippods (Chilopoda), for example Scutigera oleoptrata; millipedes (Diplopoda), for example Narceus spp.; earwigs (Dermaptera), for example Forficula auricularia; lice (Phthiraptera), for example Pediculus humanus capitis), human body lice (Pediculus humanus corporis), pubic lice (Pthirus pubis), cattle blood lice (Haematopinus usysternus), pig blood lice (Haematopinus suis), cattle jaw lice (Linognathus vituli), cattle feather lice (Bovicolabovis), Menopon allinae, Menacanthus stramineus, and Solenopotes capillatus; from the order of the Collembola (springtails), for example, Onychiurus ssp.

[0228] The compounds of formula (I) according to the present invention are also suitable for controlling nematodes: plant parasitic nematodes: for example, root-knot nematodes, such as Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica and other root-knot nematode species; cyst-forming nematodes, such as Globodera rostochiensis and other Globodera species; cereal cyst nematodes, such as Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii and other Heterodera species; seed gall nematodes, such as Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica and other root-knot nematode species; seed gall nematodes, such as Meloidogyne rapa and other Heterodera species. nematodes, Anguina species; stem and leaf nematodes, Aphelenchoides species; sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci dipsaci and other Ditylenchus species; Awlnematodes, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; Sheath and sheath-shaped nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species;Lance nematodes, species of the genus Hoploaimus; false rootknot nematodes, species of the genus Nacobbus; Needle nematodes, Longidorus elongatus and other species of the genus Longidorus; Lesion nematodes, Pratylenchus negletus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other species of the genus Pratylenchus; Burrowing nematodes, Radopholus similis and other species of the genus Radopholus; Reniform nematodes, 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.

[0229] The compounds of formula (I) and their salts can also be used to control arachnids (Arachnoidea), such as acarians (Acarina), for example the Argasidae, Ixodidae and Sarcoptidae, for example Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus africanus, moubata), Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and species of the family Phyllopsidae, such as Aculus schlechtendali, Phyllocoptrata oleivora, and Eriophyes sheldoni; species of the family Tarsonemidae, such as Phytonemus pallidus and Polyphagotarsonemus latus; species of the family Tenuipalpidae, such as Brevipalpus phoenicis; species of the family Tetranychidae, such as Brevipalpus phoenicis. spp.), such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius, and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and Oligonychus pratensis.

[0230] In one embodiment of the present invention, the present invention provides compounds of formula (I) for use in controlling insects selected from sucking or piercing insects, such as Thysanoptera, Diptera and Hemiptera, in particular the following species:

[0231] Thysanoptera: Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, and Thrips tabaci.

[0232] 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, Mediterranean fruit fly, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis), Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinias orghicola, 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 truncatum platura), cabbage fly (Delia radicum), human skin fly (Dermatobia hominis), summer toilet fly (Fannia canicularis), GeomyzaTripunctata, 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 autumnnalis, Musca domestica, Muscina stabulans), Oestrusovis (sheep fly), Opomyza florum, Oscinella frit (Swedish rod fly), Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes (silver-legged sandfly), Psorophora columbiae (Columbian scale fly), Psila rosae (carrot stem fly), Psorophora discolor (color scale fly), Prosimulium mixtum, Rhagoletis cerasi (cherry fruit fly), Rhagoletis pomonella (apple fruit fly), Sarcophaga haemorrhoidalis (red-tailed flesh fly), Sarcophaga spp., Simulium vittatum (tape fly), Stomoxys calcitrans (stable fly), Tabanus bovinus (gadfly), Tabanus spp. atratus), striped horseflies (Tabanus lineola) and Tabanus similis, and swamp flies (Tipulaoleracea) and European crane flies (Tipula paludosa);

[0233] Hemiptera, in particular aphids: Acyrthosiphon onobrychis, Adelgeslaricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphisschneideri, 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, Megouraviciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodespersicae, Myzus ascalonicus, Myzus cerasi, peach leaf aphid (Myzus varians), lettuce aphid (Nasonovia ribis-nigri), brown planthopper (Nilaparvata lugens), stalk gall aphid (Pemphigus bursarius), sugarcane flat-horned planthopper (Perkinsiellasaccharicida), Phorodonhumuli, Psylla mail, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneuralanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantii, and Viteus vitifolii.

[0234] 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 compatible compound selected from the group consisting of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers, and nutrients. Compounds used in the composition and combined with the compound of formula (I) are also referred to as active compatible compounds.

[0235] Known and reported fungicides, insecticides, nematocides, 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, fungicides, insecticides, nematocides, 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.

[0236] 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 of combinations with at least one compound of formula (I) of the present disclosure.

[0237] In particular, the compounds of the present invention can be mixed with at least one additional biologically active compatible compound (mixing partner) to form a multi-component pesticide providing a wider range of agricultural benefits, and the biologically active compatible compound includes but is not limited to insecticides, fungicides, nematicides, bactericides, acaricides, growth regulators such as root stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, other biologically active compounds or entomopathogenic bacteria, viruses or fungi.

[0238] Examples of such biologically active compounds or agents / mixing partners that can be combined / formulated with the compounds of formula (I) of the present invention are disclosed in WO2019072906A1 (pages 27 to 37).

[0239] In one embodiment, biological agents for admixture with the compounds of the invention include Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, and naturally occurring and genetically modified viral insecticides, including members of the Baculoviridae family, and insectivorous fungi.

[0240] In some cases, combinations with other invertebrate pest control compounds or agents having similar control spectra but different modes of action can be particularly beneficial for resistance management. Thus, the compositions of the present invention can further comprise a biologically effective amount of at least one additional invertebrate pest control compound or agent having a similar control spectra but a different mode of action. Contacting a plant, or the locus of such a plant, that has been genetically modified to express a plant protection compound (e.g., a protein) with a biologically effective amount of a compound of the present invention can also provide broader plant protection and facilitate resistance management.

[0241] In one embodiment of the present invention, the biologically effective amount of the compound of formula (I) in the composition ranges from 0.1% to 99% by weight relative to the total weight of the composition, preferably from 5% to 50% by weight relative to the total weight of the composition.

[0242] The present invention also provides a method for controlling invertebrate pests, which method comprises contacting the invertebrate pests, their habitats, breeding grounds, food supplies, plants, seeds, soils, areas, materials or environments where the invertebrate pests are growing or may grow, or materials, plants, seeds, soils, surfaces or spaces to be protected from attack or infestation by the pests with a biologically effective amount of the compound or an agriculturally acceptable salt, isomer / structural isomer, stereoisomer, diastereomer, enantiomer, tautomer, metal complex, polymorph or N-oxide thereof, or a combination or combination thereof.

[0243] By applying an effective amount of one or more compounds of the present invention to the environment of the pest, including agronomy and / or non-agronomy infestation site, the area to be protected or directly applied to the pest to be controlled to control invertebrate pests, and achieve protection of agronomy, horticulture and specialty crops, animals and human health. Therefore, the present invention further includes a method for controlling invertebrates living on foliage and soil and protecting agronomy and / or non-agronomy crops, including contacting invertebrates or their environment with one or more compounds of the present invention of biologically effective amount, or contacting with a composition comprising at least one such compound or a composition comprising at least one such compound and an effective amount of at least one additional biologically active compound or reagent. The preferred contact method is spraying. Alternatively, a granular composition comprising the compounds of the present invention can be applied to plant leaves or soil. By contacting plants with a composition comprising the compounds of the present invention in the form of a soil-soaking liquid formulation, in the form of a granular formulation applied to soil, in the form of a nursery box treatment agent or a transplant immersion solution, the compounds of the present invention are effectively delivered via plant intake. Other methods of contact include applying the compounds or compositions of the invention via direct and residual sprays, aerial sprays, seed coatings, microencapsulation, systemic absorption, baits, ear tags, bolus, foggers, fumigants, aerosols, dusts, and many others.

[0244] The compounds of the present invention can be incorporated into baits consumed by invertebrates or into devices such as traps. Granules or baits containing 0.01-5% active ingredient, 0.05-10% humectant, and 40-99% plant powder are effective in controlling soil insects at very low application rates (especially at doses of the active ingredient that are lethal by ingestion rather than by direct contact). The compounds of the present invention can be applied in their pure form, but are most commonly applied as formulations containing one or more compounds with suitable carriers, diluents, and surfactants, and may be combined with food depending on the intended end use. Preferred application methods include spraying aqueous dispersions or refined oil solutions of the compounds. Combinations with spray oils, spray oil concentrates, spreaders, adjuvants, other solvents, and synergists (e.g., piperonyl butoxide) often enhance the efficacy of the compounds.

[0245] The amount of application required for effective control (i.e., a "biologically effective amount") depends on the invertebrate species to be controlled, the pest's life cycle, life stage, size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient humidity, temperature, and other factors. Under normal circumstances, an application rate of about 0.01 to 2 kg of active ingredient per hectare is sufficient to control pests in agronomic ecosystems, but as little as 0.0001 kg / hectare may be sufficient, and as much as 8 kg / hectare may be required. For non-agronomic applications, effective use rates range from about 1.0 to 50 mg / square meter, but as little as 0.1 mg / square meter may be sufficient, and as much as 150 mg / square meter may be required. One skilled in the art can readily determine the biologically effective amount required for the desired level of invertebrate pest control.

[0246] Animal pests, i.e., insects, arachnids and nematodes, plants, soil or water in which plants grow, can be contacted with compounds of formula (I), their N-oxides and salts, or compositions containing them, by any application method known in the art. Thus, "contacting" includes 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 locus of the animal pest or plant).

[0247] The compounds of the invention or the pesticidal compositions comprising them can be used to protect growing plants and crops from attack and infestation by animal pests, in particular insects, acarids or arachnids, by contacting the plants / crops with a parasiticidally effective amount of at least one compound of the invention. The term "crops" refers to growing and harvested crops.

[0248] In one embodiment, the present invention provides a method of protecting a crop from attack or infestation by an invertebrate pest, comprising contacting the crop with a biologically effective amount of a compound or composition of the present invention, its isomers, polymorphs, N-oxides or salts.

[0249] The compounds of the present invention are used as such or in the form of compositions by treating insects or plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from insect attack with an insecticidal effective amount of the active compound. Application can be carried out both before and after the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms are infested by insects.

[0250] In one embodiment, the present invention provides a method for protecting seeds from soil insects and seedling roots and shoots from soil and foliar insects, comprising contacting the seeds with a compound or composition of the present invention, its N-oxide or salt before sowing and / or after pre-germination.

[0251] In addition, the present invention provides a method for treating or protecting an animal from parasitic infestation or infection, which comprises orally, topically or parenterally administering or applying to the animal a biologically effective amount of a compound or composition of the present invention, its isomers, polymorphs, N-oxides or veterinarily acceptable salts.

[0252] For use in the treatment of crop plants, the application rate (effective dose) of the compounds of the present invention in agricultural or horticultural crops can be in the range of 1 gai to 5000 gai per hectare, preferably 25 g to 600 g / hectare, more preferably 50 g to 500 g / hectare.

[0253] The compounds and compositions of the present invention are particularly useful for controlling a wide variety of insects on a variety of cultivated plants, such as cereals, root crops, oilseed crops, vegetables, spices, ornamentals, for example, durum and other wheats, barley, oats, rye, corn (fodder corn and sugar / sweet corn and field corn), soybeans, oilseed crops, crucifers, cotton, sunflowers, bananas, rice, rapeseed, turnip rape, sugar beet, fodder beet, eggplant, potato, grass, lawn, turf, fodder grass, tomato, leek, pumpkin / winter squash, cabbage, iceberg lettuce, peppers, cucumber, melons, brassicas, cucurbits, beans, peas, garlic, onions, carrots, tuber plants (e.g., potatoes), sugar cane, tobacco, grapes, petunias, geraniums / geraniums, pansies, and impatiens seeds.

[0254] In particular, the compounds or compositions of the present invention can be used to protect crop plants such as cereals, corn, rice, soybeans and other legumes, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbits, oil-producing plants, tobacco, coffee, tea, cocoa, sugar beets, sugar cane, cotton, potatoes, tomatoes, onions, peppers and other vegetables, and ornamental plants.

[0255] The compounds of the present invention are effective by contact (via soil, glass, walls, mosquito nets, carpets, plant parts or animal parts) and ingestion (baits or plant parts).

[0256] The compounds of the present invention may also be used to combat non-crop invertebrate pests such as ants, termites, wasps, flies, mosquitoes, crickets or cockroaches. For use against such non-crop pests, the compounds of the present invention are preferably used in bait compositions.

[0257] Bait can be liquid, solid or semisolid preparation (for example gel).Solid bait can be made into various shapes and forms suitable for respective application, for example granule, block, rod, dish.Liquid bait can be filled in various equipment to guarantee correct use, for example open container, spray device, drop source or evaporation source.Gel can be based on aqueous or oily matrix, and can be prepared according to the special needs aspect viscosity, moisture retention or aging characteristics.

[0258] The bait used in the composition is a product that is sufficiently attractive to induce insects (such as ants, termites, wasps, flies, mosquitoes, crickets, etc. or cockroaches) to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are selected from, for example, but not limited to, animal and / or plant proteins (meal, fish meal or blood meal, insect parts, egg yolks), fats and oils of animal and / or plant origin, or mono-, oligo- or poly-organic sugars, in particular sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or rotten parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as feeding stimulants. It is well known that sex pheromones are more insect-specific. Specific pheromones are described in the literature and are known to those skilled in the art.

[0259] For use in bait compositions, typical levels of active ingredient are from 0.001% to 15% by weight, ideally from 0.001% to 5% by weight of active compound.

[0260] Formulations of the compounds of the invention as aerosols (eg in spray cans), oil sprays or pump sprays are very suitable for the non-professional user to control pests such as flies, fleas, ticks, mosquitoes or cockroaches. Aerosol formulations preferably consist 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 with a boiling range of about 50 to 250° C. (e.g. kerosene), dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, an aromatic hydrocarbon (e.g. toluene, xylene), water, in addition adjuvants such as an emulsifier (e.g. sorbitan monooleate, oleyl ethoxylates containing 3 to 7 mol of ethylene oxide, fatty alcohol ethoxylates), a fragrance oil (e.g. ether oils, esters of medium-chain fatty acids with lower alcohols, aromatic carbonyl compounds), if appropriate a stabilizer (e.g. sodium benzoate), an amphoteric surfactant, a lower epoxide, triethyl orthoformate and, if desired, a propellant (e.g. propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide or a mixture of these gases).

[0261] Oil spray formulations differ from aerosol formulations in that no propellant is used. For use in spray compositions, the active ingredient is present in an amount of 0.001 to 80% by weight, preferably 0.01 to 50% by weight, and most preferably 0.01 to 15% by weight.

[0262] The compounds of the present invention and their respective compositions can also be used in mosquito coils and fumigation trays, smoke cartridges, vaporizer plates or long-term vaporizers, and can also be used in moth repellent papers, moth repellent mats or other vaporizer systems that do not rely on heat.

[0263] Methods for controlling infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis and leishmaniasis) using the compounds of formula (I) and their respective compositions also include treating surfaces of sheds and houses, spraying and impregnating curtains, tents, clothing, mosquito nets, tsetse-fly traps, etc. Insecticidal compositions for application to fibers, fabrics, knitwear, nonwovens, netting materials or foils and tarpaulins preferably comprise a mixture comprising an insecticide, optionally an insect repellent and at least one binder. Suitable insect repellents are, for example, N,N-diethyl-m-toluamide (DEET), N,N-diethylphenylacetamide (DEPA), 1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine, (2-hydroxymethylcyclohexyl)acetic acid lactone, 2-ethyl-1,3-hexanediol, indanone, methyl neodecanoamide (MNDA), a pyrethroid not used for insect control, for example {(+ / -)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-pyrethroid (Esbiothrin), derived from or identical to plant extracts such as limonene, eugenol, (+)-Eucamalol (1), (-)-1-epi-eucamalol or from plants such as Eucalyptus globulus Insect repellents based on crude plant extracts of Cymbopogan maculata, Vitex rotundifolia, Cymbopogan martinii, Cymbopogan citratus (lemongrass), and Cymopogan nartdus (citronella). Suitable binders are selected from, for example, vinyl esters of fatty acids (e.g., vinyl acetate and versatate), acrylates and methacrylates of alcohols (e.g., butyl acrylate, 2-ethylhexyl acrylate, and methyl acrylate), polymers and copolymers of mono- and di-ethylenically unsaturated hydrocarbons (e.g., styrene and aliphatic dienes such as butadiene).

[0264] Impregnation of curtains and mosquito nets is usually done by dipping the textile material into an emulsion or dispersion of the insecticide or by spraying it onto the net.

[0265] The compounds of the present invention and their compositions can be used to protect wooden materials (such as trees, board fences, sleepers, etc.) and buildings (such as houses, outbuildings, factories), as well as building materials, furniture, leather, fibers, vinyl products, wires and cables, etc. from ant and / or termite infestation, and to control ant and termite damage to crops or humans (for example, when pests invade houses and public facilities). The compounds of the present invention can be applied not only to the surrounding soil surface or subfloor soil to protect wooden materials, but also to the surfaces of wood products, such as subfloor concrete, niche columns, beams, plywood, furniture, etc., wood products such as particleboard, semi-board, vinyl products such as coated wire, vinyl sheet, insulation materials such as styrene foam, etc.

[0266] When applied to ants that harm crops or humans, the compound of the present invention is applied to the crops or the surrounding soil, or directly to the ant nests or the like.

[0267] Seed treatment

[0268] The invention further provides treated seeds comprising a compound of the invention, particularly in an amount of about 0.0001% to about 1% by weight of the seed before treatment.

[0269] The compounds according to the invention are also suitable for treating seed to protect it from insect pests, especially soil-dwelling insects, and the roots and shoots of the resulting plants from attack by soil pests and foliar insects.

[0270] The compounds of the present invention are particularly suitable for protecting seeds from soil pests and the roots (white grubs, termites, wireworms) and shoots of the resulting plants from soil pests and foliar insects. Protection of the roots and shoots of the resulting plants is preferred. Protection of the shoots of the resulting plants from piercing-sucking insects is more preferred, with protection from aphids, leafhoppers, thrips, and whiteflies being most preferred.

[0271] The present invention therefore includes a method for protecting seeds from insects, in particular soil insects, and seedling roots and shoots from insects, in particular soil and foliar insects, which method comprises contacting the seeds with a compound of the invention before sowing and / or after pre-germination. Particularly preferred are methods in which the roots and shoots of the plant are protected, more preferably methods in which the shoots of the plant are protected from piercing-sucking insects, and most preferably methods in which the shoots of the plant are protected from aphids.

[0272] The term seed includes all kinds of seeds and plant propagules, including but not limited to true seeds, seed cuttings, suckers, corms, bulbs, fruits, tubers, grains, cuttings, cut shoots, etc., and in preferred embodiments refers to true seeds.

[0273] The term seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting.

[0274] The present invention also includes seeds coated with or containing an active compound. The seeds may be coated with a seed coating composition containing a compound of the present 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.

[0275] The term "coated and / or containing" generally means that the active ingredient is mostly on the surface of the propagation product at the time of application, but, depending on the method of application, a greater or lesser amount of the ingredient may penetrate into the propagation product. When the propagation product is (re)planted, it may absorb the active ingredient and moisture.

[0276] Suitable seeds are seeds of cereals, root crops, oilseed crops, vegetables, spices, ornamentals, for example seeds of durum wheat and other wheats, barley, oats, rye, corn (fodder corn and sugar corn / sweet corn and field corn), soybeans, oilseed crops, crucifers, cotton, sunflower, banana, rice, rapeseed, Brassica rapa, sugar beet, fodder beet, eggplant, potato, grass, lawn, turf, fodder grass, tomato, leek, pumpkin / winter squash, cabbage, iceberg lettuce, peppers, cucumber, melons, Brassica rapa, melons, beans, peas, garlic, onion, carrot, tuber plants (such as potatoes), sugar cane, tobacco, grapes, petunia, geranium / geranium, pansy and impatiens.

[0277] Furthermore, the compounds according to the invention can be used for the treatment of seeds from plants which have been rendered tolerant to the action of herbicides or fungicides or insecticides as a result of breeding, including genetic engineering methods.

[0278] For example, the compounds of the invention can be used to treat seeds from plants that are resistant to herbicides selected from the group consisting of sulfonylureas, imidazolinones, glufosinate or glyphosate isopropylammonium and similar active substances (see, for example, EP242236, EP242246) (WO92 / 00377) (EP257993, US5013659) or in transgenic crop plants (e.g. cotton) that have the ability to produce Bacillus thuringiensis toxins (Bt toxins) that render the plants resistant to certain pests (EP142924, EP193259).

[0279] In addition, the compounds of the invention can be used to treat seeds from plants having improved properties compared to existing plants, which can be produced, for example, by conventional breeding methods and / or by generating mutations, or by recombinant procedures. For example, many cases have been described of crop plants being recombinantly modified to improve the starch synthesized in the plants (e.g., WO 92 / 11376, WO 92 / 14827, WO 91 / 19806) or transgenic crop plants having an improved fatty acid composition (WO 91 / 13972).

[0280] The seed treatment application of the compounds of the invention is carried out by spraying or dusting the seeds before sowing of the plants and before emergence of the plants.

[0281] Compositions particularly useful for seed treatment are for example:

[0282] Soluble concentrates (SL, LS)

[0283] Emulsion (EW, EO, ES)

[0284] Suspension (SC, OD, FS)

[0285] Water-dispersible granules and water-soluble granules (WG, SG)

[0286] Water-dispersible powders and water-soluble powders (WP, SP, WS)

[0287] Gel formulation (GF)

[0288] Powders (DP, DS)

[0289] Conventional seed treatment formulations include, for example, flowable concentrates FS, solutions LS, powders for dry treatment DS, water-dispersible powders for slurry treatment WS, water-soluble powders SS, and emulsions ES and EC, as well as gel formulations GF. These formulations can be applied to seeds diluted or undiluted. They can be applied directly to the seeds before sowing or after pre-germination.

[0290] In one embodiment, the FS formulation is used for seed treatment. Typically, the FS formulation may comprise 1 to 800 g / l active ingredient, 1 to 200 g / l surfactant, 0 to 200 g / l antifreeze, 0 to 400 g / l binder, 0 to 200 g / l pigment, and up to 1 liter of solvent, preferably water.

[0291] In particular, FS formulations of the compounds of the invention for seed treatment generally comprise 0.1 to 80% by weight (1 to 800 g / l) of active ingredient, 0.1 to 20% by weight (1 to 200 g / l) of at least one surfactant, for example 0.05 to 5% by weight of a wetting agent and 0.5 to 15% by weight of a dispersant, up to 20% by weight, for example 5 to 20% by weight of an antifreeze agent, 0 to 15% by weight, for example 1 to 15% by weight of a pigment and / or dye, 0 to 40% by weight, for example 1 to 40% by weight of a binder (adhesive / adhesive), optionally up to 5% by weight, for example 0.1-5% by weight of a thickener, optionally 0.1 to 2% of an antifoaming agent, and optionally, in an amount of, for example, 0.01 to 1% by weight, a preservative, for example a biocide, an antioxidant, etc., and up to 100% by weight of a filler / carrier.

[0292] The seed treatment formulation may additionally comprise a binder and optionally a colorant.

[0293] Binders may be added to improve the adhesion of the active material to the treated seeds. Suitable binders are homopolymers or copolymers of alkylene oxides such as ethylene oxide or propylene oxide, polyvinyl acetate, polyvinyl alcohol, polyvinyl pyrrolidone, and copolymers thereof, ethylene-vinyl acetate copolymers, acrylic homopolymers and copolymers, polyvinylamine, polyvinylamide and polyvinylpyrimidine, polysaccharides such as cellulose, methylcellulose and starch, polyolefin homopolymers and copolymers such as olefin / maleic anhydride copolymers, polyurethanes, polyesters, polystyrene homopolymers and copolymers.

[0294] Optionally, a colorant can also be included in the preparation. Suitable colorants or dyes for seed treatment preparations are Rhodamine B, CI Pigment Red 1 12, CI 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 1 12, 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.

[0295] An example of a gelling agent is carrageenan

[0296] In seed treatment, the application rate of the compound of the present invention is generally 0.1 g to 10 kg per 100 kg of seeds, preferably 1 g to 5 kg per 100 kg of seeds, more preferably 1 g to 1000 g per 100 kg of seeds, in particular 1 g to 200 g per 100 kg of seeds. Therefore, 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 is generally 0.1 g to 10 kg per 100 kg of seeds, preferably 1 g to 5 kg per 100 kg of seeds, in particular 1 g to 1000 g per 100 kg of seeds.

[0297] Animal Health

[0298] The invention further provides agricultural and / or veterinary compositions comprising at least one compound according to the invention.

[0299] In one embodiment, the present invention provides a compound of formula (I), its agriculturally acceptable salts, isomers / structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs or N-oxides, compositions or combinations for use in controlling invertebrate pests in agricultural and / or horticultural crops or parasites on animals.

[0300] The compounds of the formula (I), their N-oxides and / or their veterinarily acceptable salts are also particularly suitable for combating parasites in and on animals.

[0301] Therefore, it is an object of the present invention to provide new methods for controlling parasites in and on animals. Another object of the present invention is to provide safer insecticides for animals. Another object of the present invention is to provide insecticides for use in animals that can be used at lower doses than existing insecticides. Another object of the present invention is to provide insecticides for use in animals that provide long-lasting control of parasites.

[0302] The present invention also relates to a composition comprising a parasiticidally effective amount of at least one compound of formula (I), its N-oxide or a veterinarily acceptable salt thereof and an acceptable carrier for use in combating parasites in and on animals.

[0303] The present invention also provides a method for treating, controlling, preventing and protecting animals from parasitic infestation and infection, which comprises orally, topically or parenterally administering or applying a parasiticidally effective amount of the compound of the present invention or a composition comprising the same to the animal.

[0304] The present invention also provides a method for preparing a composition for treating, controlling, preventing or protecting an animal from parasitic infestation or infection, the composition comprising a parasiticidally effective amount of a compound of the present invention or a composition comprising the same.

[0305] Activity of compounds against agricultural pests does not indicate their suitability for control of endo- and ectoparasites in and on animals, which requires, for example, low non-emetic doses in the case of oral application, metabolic compatibility with animals, low toxicity and safe handling.

[0306] Surprisingly, it has now been found that the compounds according to the invention are useful for combating endo- and ectoparasites in and on animals.

[0307] The compounds of the present invention and compositions comprising them are preferably used for controlling and preventing infestations and infections in animals including warm-blooded animals (including humans) and fish. They are suitable, for example, for controlling and preventing infestations and infections in mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, buffaloes, donkeys, fallow deer and reindeer, as well as fur-bearing animals such as mink, chinchillas and raccoons, birds such as hens, geese, turkeys and ducks, and fish such as freshwater fish and saltwater fish such as trout, carp and eels.

[0308] The compounds of the present invention and compositions comprising them are preferably used for controlling and preventing infestations and infections in domestic animals such as dogs or cats.

[0309] Infestations of warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes, and fleas.

[0310] The compounds of the invention and compositions comprising them are suitable for systemic and / or non-systemic control of ecto- and / or endoparasites. They may have an active effect on all or some stages of development.

[0311] The compounds according to the invention are particularly suitable for combating ectoparasites.

[0312] The compounds according to the invention are particularly suitable for combating parasites of the following orders and species, respectively: fleas (Siphonaptera), for example Ctenocephalides felis, Ctenocephalides cams, Xenopsylla cheopis, Pulex irritans, Tunga penetrans and Nosopsyllus fasciatus, cockroaches (Blattaria Blattodea), for example Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae and Blattella orientalis. orientalis, flies and mosquitoes (Diptera), for example, Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis), Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex spp.nigripalpus), Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucilia cuprina, Lucilius sericata, Lycoria pectoralis, Mansonia spp.), housefly (Musca domestica), stable fly (Muscina stabulans), sheep fly (Oestrus ovis), silver-legged sandfly (Phlebotomus argentipes), Columbia scale midge (Psorophora columbiae), color scale midge (Psorophora discolor), Prosimulium mixtum, red-tailed flesh fly (Sarcophaga haemorrhoidalis), flesh flies (Sarcophaga spp.), tapefly (Simulium vittatum), stable biting fly (Stomoxys calcitrans), gadfly (Tabanus bovinus), black horsefly (Tabanus atratus), striped horsefly (Tabanus lineola) and Tabanus similis, lice (order Pediculus), for example, head louse (Pediculus humanus capitis), body louse (Pediculus humanus corporis), pubic louse (Pthirus pubis), blood louse (Haematopinus eurysternus), Haematopinus suis, Linognathusvituli), Bovicola bovis, Menopon allinae, Menacanthus stramineus, and Solenopotes capillatus; Ticks and parasitic mites (Parasitiformes): Ticks (Ixodida), for example, Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), for example, Ornithonyssus bacoti and Dermanyssus gallinae, Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp. spp.), Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptesspp., Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Arilus critatus, Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp., Mallophagida (Arnblycerina and Ischnocerina), for example, Trimenopon spp. spp.), Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.

[0313] Ascaris nematodes:

[0314] Wipeworms and Trichinosis (Trichosyringida), for example, Trichinella spp., (Trichuris spp.), Capillaria spp., Rhabditis spp., Strongyloides spp., Helicephalobus spp., Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (hookworms), Trichostrongylus spp., Haemonchus contortus., Ostertagia spp. spp.), Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostomas 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, Ascaridigalli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp. and Oxyuris equi, Camallanida, for example, Dracunculus medinensis (Guinea worm), worms), from the order of the Spirurida, for example, Thelazia spp., Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilaria spp., Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi and Habronema spp., spiny-headed worms (class Acanthocephala), for example, Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp., Planarians (Platyhelminthes): Flukes (Trematoda), for example, Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchissinensis, Schistosoma spp., Trichobilharzia spp.), Alaria alata, Paragonimus spp. and Nanocyetes spp., Cercomeromorpha, in particular 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 Hymenolepis spp.

[0315] The compounds of formula (I) and compositions containing them are particularly useful for controlling pests of the orders Diptera, Siphonaptera and Ixodida.

[0316] In one embodiment, the present invention provides the use of compounds of formula (I) and compositions containing them for controlling mosquitoes.

[0317] In one embodiment, the present invention provides the use of the compounds of formula (I) and compositions containing them for controlling flies.

[0318] In one embodiment, the present invention provides the use of compounds of formula (I) and compositions containing them for controlling fleas.

[0319] Use of the compounds of the present invention and compositions containing them for controlling ticks is another embodiment of the present invention.

[0320] The compounds according to the invention are also particularly suitable for combating endoparasites (nematodes, roundworms, spiny head worms and planarians).

[0321] In one embodiment, the compounds of the present invention may be administered prophylactically or therapeutically.

[0322] In another embodiment, the compounds of the invention are administered directly or in the form of a suitable formulation, orally, topically / dermally or parenterally.

[0323] For oral administration to warm-blooded animals, the compounds of the present invention can be formulated into animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, immersions, gels, tablets, boluses, and capsules. In addition, the compounds of the present invention can be administered to the animal in the animal's drinking water. For oral administration, the dosage form selected should provide the animal with 0.01 mg / kg to 100 mg / kg of animal body weight per day, preferably 0.5 mg / kg to 100 mg / kg of animal body weight per day of the compound of the present invention.

[0324] Alternatively, the compounds of the present invention can be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous, or subcutaneous injection. The compounds of the present invention can be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds of the present invention can be formulated into implants for subcutaneous administration. In addition, the compounds of the present invention can be administered to animals transdermally. For parenteral administration, the selected dosage form should provide the animal with 0.01 mg / kg to 100 mg / kg of animal body weight of the compound of the present invention per day.

[0325] The compounds of the present invention can also be administered topically to animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations, as well as ointments or oil-in-water or water-in-oil emulsions. For topical administration, dips and sprays typically contain 0.5 ppm to 5,000 ppm, preferably 1 ppm to 3,000 ppm, of the compounds of the present invention. In addition, the compounds of the present invention can be formulated into ear tags for animals, particularly quadrupeds, such as cattle and sheep.

[0326] Suitable preparations are: solutions, such as oral solutions, concentrates for oral administration after dilution, solutions for application on the skin or in body cavities, pour-on preparations, gels; emulsions and suspensions for oral or transdermal administration; semisolid preparations; preparations in which the active compound is processed in an ointment base or an oil-in-water or water-in-oil emulsion base; solid preparations, such as powders, premixes or concentrates, granules, pills, tablets, boluses, capsules; aerosols and inhalants, and shaped articles containing the active compound.

[0327] Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding other ingredients such as acids, bases, buffer salts, preservatives and solubilizers.

[0328] The solution was filtered and filled aseptically.

[0329] Suitable solvents are physiologically tolerable solvents, for example water, alkanols, such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycol, N-methylpyrrolidone, 2-pyrrolidone, and mixtures thereof.

[0330] The active compound can optionally be dissolved in physiologically tolerated vegetable or synthetic oils suitable for injection.

[0331] Suitable solubilizers are solvents which promote the dissolution of the active compound in the main solvent or prevent its precipitation. Examples are polyvinyl pyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil and polyoxyethylated sorbitan esters.

[0332] Suitable preservatives are benzyl alcohol, chlorobutanol, parabens and n-butanol.

[0333] Oral solutions are administered directly. Concentrates are administered orally after pre-diluting to the use concentration. Oral solutions and concentrates are prepared according to existing techniques and as described above for injectable solutions; sterile procedures are not required.

[0334] Solutions for use on the skin are dropped, spread, rubbed, spread, or sprayed onto the skin.

[0335] Solutions for application to the skin are prepared according to known techniques and as described above for injection solutions, sterile procedures not being necessary.

[0336] Other suitable solvents are polypropylene glycol, phenylethyl alcohol, phenoxyethanol, esters (such as ethyl acetate or butyl acetate, benzyl benzoate), ethers (such as alkylene glycol alkyl ethers, for example dipropylene glycol monomethyl ether), ketones (such as acetone, methyl ethyl ketone), aromatic hydrocarbons, vegetable and synthetic oils, dimethylformamide, dimethylacetamide, transcutol, solketal, propylencarbonate, and mixtures thereof.

[0337] It may be advantageous to add a thickener during the preparation process. Suitable thickeners are: inorganic thickeners such as bentonite, colloidal silicic acid, aluminum monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohol and its copolymers, acrylates and methacrylates.

[0338] 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 in the case of the injectable solution with a sufficient amount of a thickening agent to produce a transparent material with an ointment-like consistency. The thickening agents used are those listed above.

[0339] Pour-on formulations are poured or sprayed onto a limited area of ​​skin; the active compound penetrates the skin and acts systemically. Pour-on formulations are prepared by dissolving, suspending, or emulsifying the active compound in a suitable skin-compatible solvent or solvent mixture. If appropriate, other adjuvants are added, such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, and adhesives.

[0340] Suitable solvents are, for example, water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethyl alcohol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers, for example 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 oils or synthetic oils, DMF, dimethylacetamide, n-alkylpyrrolidones such as methylpyrrolidone, n-butylpyrrolidone or n-octylpyrrolidone, N-methylpyrrolidone, 2-pyrrolidone, 2,2-dimethyl-4-oxy-methylene-1,3-dioxolane or glycerol formal.

[0341] Suitable colorants are, for example, all colorants which are approved for use on animals and which can be dissolved or suspended.

[0342] Suitable absorption-promoting substances are, for example, dimethyl sulfoxide, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and their copolymers with polyethers, fatty acid esters, triglycerides or fatty alcohols.

[0343] Suitable antioxidants are, for example, sulfites or metabisulfites, such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole or tocopherol.

[0344] Suitable light stabilizers are, for example, novantisolic acid. Suitable binders are, for example, cellulose derivatives, starch derivatives, polyacrylates, or natural polymers such as alginates or gelatin. The emulsion can be administered orally, transdermally, or by injection. The emulsion can be of the water-in-oil or oil-in-water type.

[0345] They are prepared by dissolving the active compound in the hydrophobic or hydrophilic phase and homogenizing it with the solvent of the other phase and, if appropriate, further auxiliaries (such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-increasing substances) by means of suitable emulsifiers.

[0346] Suitable hydrophobic phases (oils) are:

[0347] Liquid paraffin, silicone oil, natural plant oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic / capric diglyceride, and chain lengths of C1-C 12 mixture of triglycerides of vegetable fatty acids or other specially selected natural fatty acids, partial glycerides of saturated or unsaturated fatty acids that may also contain hydroxyl groups, monoglycerides and diglycerides of Cs-do fatty acids, fatty acid esters such as ethyl stearate, dibutyl adipate, hexyl laurate, dipropylene glycol perlargonate, medium chain branched fatty acids and chain lengths of C 16 -C18 Esters of saturated fatty alcohols, isopropyl myristate, isopropyl palmitate, chain length C 12 -C 18 Caprylic / capric esters of saturated fatty alcohols, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters such as synthetic duck tail fat, dibutyl phthalate, diisopropyl adipate and ester mixtures related to the latter, fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetearyl 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.

[0348] Suitable emulsifiers are, for example, nonionic surfactants, such as polyethoxylated castor oil, polyethoxylated sorbitan monooleate, sorbitan monostearate, glyceryl monostearate, polyoxyethyl stearate, alkylphenol polyglycol ethers; amphoteric surfactants, such as disodium N-lauryl iminodipropionate or lecithin.

[0349] Suitable anionic surfactants are, for example, sodium lauryl sulfate, fatty alcohol ether sulfates, mono- and di-alkyl polyethylene glycol ether orthophosphate monoethanolamine salts; a suitable cationically active surfactant is cetyltrimethylammonium chloride.

[0350] Suitable further auxiliaries are, for example, substances which increase the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycol, waxes, colloidal silicic acid or mixtures of the aforementioned substances.

[0351] Suspensions can be administered orally or topically / dermally. They are prepared by suspending the active compound in a suspending agent and, if appropriate, adding other adjuvants, such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers.

[0352] Liquid suspensions are both homogeneous solvents and solvent mixtures.

[0353] Suitable wetting agents (dispersants) are the emulsifiers given above.

[0354] Further auxiliaries which may be mentioned are those given above.

[0355] Semisolid preparations can be administered orally or topically / dermally. They differ from the suspensions and emulsions described above only in their higher viscosity.

[0356] To prepare solid preparations, the active compound is mixed with suitable excipients, if appropriate with auxiliaries, and brought into the desired form.

[0357] Suitable excipients are all physiologically tolerable solid inert substances. Inorganic and organic substances are used. Inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, bicarbonates, aluminum oxide, titanium oxide, silicic acid, clays, precipitated or colloidal silicon dioxide, or phosphates. Organic substances are, for example, sugars, cellulose, foods and feeds such as milk powder, animal meal, cereal flours and scraps, and starch.

[0358] Suitable auxiliaries are the above-mentioned preservatives, antioxidants and / or colorants.

[0359] Other suitable adjuvants are lubricants and glidants, for example magnesium stearate, stearic acid, talc, bentonite, disintegration-promoting substances such as starch or cross-linked polyvinyl pyrrolidone, binders such as starch, gelatin or linear polyvinyl pyrrolidone, and dry binders such as microcrystalline cellulose.

[0360] In general, a "parasiticidally effective amount" refers to the amount of active ingredient required to achieve an observable effect on growth (including necrosis, death, delay, prevention and removal, destruction or otherwise reducing the appearance and activity of the target organism). For the various compounds / compositions used in the present invention, the parasiticidally effective amount can vary. The parasiticidally effective amount of the composition will also vary depending on prevailing conditions such as the desired parasiticidal effect and duration, target species, mode of administration, etc. Compositions useful in the present invention typically contain from about 0.001 to 95% of a compound of the invention.

[0361] Typically, it is advantageous to administer the compound of the present invention in a total amount of 0.5mg / kg to 100mg / kg, preferably 1mg / kg to 50mg / kg, every day. It is 10ppm to 80 weight % that the instant formulation contains a concentration, preferably 0.1 to 65 weight %, more preferably 1 to 50 weight %, most preferably a compound of the antiparasitic (preferably ectoparasite) of 5 to 40 weight %. It is 0.5 to 90 weight % that the preparation diluted before use contains a concentration, preferably a compound of the antiparasitic ectoparasite of 1 to 50 weight %. In addition, it is 10ppm to 2 weight % that the formulation comprises a concentration, preferably 0.05 to 0.9 weight %, very particularly preferably the compounds of the present invention of the antiparasitic endoparasite of 0.005 to 0.25 weight %.

[0362] In one embodiment, a composition comprising a compound of the invention is administered transdermally / topically.

[0363] In another embodiment, topical administration is carried out in the form of shaped articles comprising the compound, such as collars, medallions, ear tags, bands for fastening to body parts, as well as adhesive strips and foils.

[0364] Generally, it is advantageous to administer a solid formulation of the compound of the invention which releases a total amount of 10 to 300 mg / kg, preferably 20 to 200 mg / kg, most preferably 25 to 160 mg / kg of the treated animal's body weight over the course of three weeks.

[0365] To produce shaped articles, thermoplastic and flexible plastics as well as elastomers and thermoplastic elastomers are used. Suitable plastics and elastomers are polyethylene resins, polyurethanes, polyacrylates, epoxy resins, cellulose, cellulose derivatives, polyamides, and polyesters that are sufficiently compatible with the compounds of the invention. A detailed list of plastics and elastomers, as well as procedures for producing shaped articles, are provided, for example, in WO 2003 / 086075.

[0366] Positive crop response:

[0367] The compounds of the present invention not only effectively control insect and acarid pests, but also show positive crop responses, such as plant growth-promoting effects, such as promoting root growth, enhancing tolerance to drought, high salinity, high temperature, cold, frost or light radiation, improving flowering, improving nutrient utilization (such as improving nitrogen assimilation), increasing high-quality plant production, more tillers, and enhancing resistance to fungi, insects, pests, etc., thereby increasing yield.

[0368] Chemical Examples:

[0369] The following examples illustrate manners and processes for preparing the compounds of the present invention, but are not intended to be limiting and include the best mode contemplated by the inventors for practicing the invention.

[0370] 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)

[0371] Step-1: 2-(Trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5(4H)-one

[0372] To a stirred solution of 3-(trifluoromethyl)-1H-pyrazole-5-amine (2.0 g, 13.24 mmol) in anhydrous N,N-dimethylformamide (25 mL), a solution of (E)-3-ethoxyacrylate (2.29 g, 15.88 mmol) in anhydrous N,N-dimethylformamide (2 mL) was added dropwise at 25 ° C over 15 min, followed by the addition of cesium carbonate (8.63 g, 26.50 mmol). The reaction was heated at 100 ° C for 16 h. After the reaction was complete, 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 h. 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 and concentrated to obtain the crude product, which was purified by silica gel column chromatography using 60% ethyl acetate in hexane as eluent to obtain 2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5(4H)-one (2.2 g, 10.83 mmol, 82% yield). 1 H-NMR (400MHz, DMSO-d6) δ12.43 (s, 1H), 8.56-8.58 (m, 1H), 6.17-6.20 (m, 2H); ESI-MS (m / z) 201.95 (MH).

[0373] Step 2: 5-Bromo-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0374] To 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) at 25°C was added phosphorus(V)oxybromide (7.06 g, 24.62 mmol). 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 a saturated sodium bicarbonate solution (200 ml), brine (100 ml), and water (100 ml), dried over anhydrous sodium sulfate, and concentrated to obtain the crude product, which was purified by silica gel column chromatography using 10% ethyl acetate in hexane as the eluent to obtain 5-bromo-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (2.2 g, 8.27 mmol, 67% yield). 1 H-NMR (400MHz, DMSO-d6) δ9.20 (d, J = 7.3 Hz, 1H), 7.50 (d, J = 7.3 Hz, 1H), 7.28 (s, 1H).

[0375] Step 3: 5-(5-bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0376] A stirred solution of 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, 25.40 mmol) in anhydrous tetrahydrofuran (100 mL) was thoroughly deoxygenated by three vacuum / nitrogen cycles, followed by the addition of 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 (2x100 mL). The combined ethyl acetate layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product, which was purified by silica gel column chromatography using 10% ethyl acetate in hexane as 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. 1 H-NMR (400MHz, DMSO-d6) δ9.31(dd,J=7.3,0.9Hz,1H),8.63(d,J=1.8Hz,1H),8.15(d,J=1.8 Hz,1H),7.87(d,J=7.3Hz,1H),7.37(s,1H),3.05(q,J=7.3Hz,2H),1.23(t,J=7.3Hz,3H); ESI MS(m / z)404.70,405.70[(MH) + Br 79,81 ].

[0377] Step 4: 5-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0378] To 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 added meta-chloroperbenzoic acid (5.71 g, 19.84 mmol) in portions at 0-5 ° C. The reaction mixture was stirred at 25 ° C for 5 h. After the reaction was complete, the reaction mixture was cooled to 0 ° C and 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 on a silica gel CombiFlash system using 25% ethyl acetate in hexanes as eluent to afford 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 H-NMR (400MHz, DMSO-d6) δ9.45(dd,J=7.3,0.9Hz,1H),9.22(d,J=2.1Hz,1H),8.65(d,J=2.1 Hz,1H),7.65(d,J=7.3Hz,1H),7.49(s,1H),3.93(q,J=7.4Hz,2H),1.29(t,J=7.5Hz,3H); ESI MS(m / z)434.65,435.65[(MH) + Br 79,81 ].

[0379] Step 5: 5-(3-(ethylsulfonyl)-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0380] To a stirred solution of 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) and anhydrous N,N-dimethylformamide (6 mL) was added potassium carbonate (191 mg, 1.38 mmol). 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 (2x30 mL). The combined ethyl acetate layers were washed with brine (50 mL) and water (100 mL), dried over anhydrous sodium sulfate and concentrated to give a crude product, which was purified by silica gel column chromatography using 40% ethyl acetate in hexane as eluent to give 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, 18% yield). 1 H-NMR (400MHz, DMSO-d6) δ9.49(dd,J=7.3,0.6Hz,1H),9.35(d,J=2.4Hz,1H),8.68(d,J=2.4Hz,1H),7.73(d,J=7.3H z,1H),7.53(s,1H),6.94(s,1H),3.98(q,J=7.3Hz,2H),2.54(s,3H),1.32(t,J=7.5Hz,3H); ESI-MS(m / z)504.95(MH) + .

[0381] Example 2: Synthesis of 5-bromo-3-(ethylthio)-2-(tributylstannyl)pyridine (Intermediate 5) in Example 1

[0382] Step-1: 2,5-Dibromopyridin-3-amine

[0383] To a stirred solution of iron (5.94 g, 106.0 mmol) in acetic acid (50 mL), 2,5-dibromo-3-nitropyridine (12.0 g, 42.6 mmol) was added in portions at 25 ° C. The reaction was stirred at 80 ° C for 1 h. After the reaction was completed, 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 × 200 ml). The combined ethyl acetate layer was washed with saturated sodium bicarbonate solution (200 ml), dried over anhydrous sodium sulfate and concentrated to obtain a crude product, which was purified by silica gel column chromatography using 20% ​​ethyl acetate in hexane as eluent to obtain 2,5-dibromopyridine-3-amine (7.0 g, 27.8 mmol, 65% yield). 1H-NMR (400MHz, DMSO-d6) δ7.64 (d, J = 2.1Hz, 1H), 7.25 (d, J = 2.1Hz, 1H), 5.82 (s, 2H); ESI MS (m / z) 252.50, 254.50 [(MH) + Br 79,81 ].

[0384] Step-2: 2,5-Dibromo-3-(ethylthio)pyridine

[0385] To 1,2-diethyl disulfide (4.11mL, 33.3mmol) in 1,2-dichloroethane (70mL), tert-butyl nitrite (4.96mL, 41.7mmol) was added dropwise at 25°C, and the reaction was stirred for 1h at 40°C. After that, 2,5-dibromopyridine-3-amine (7.0g, 27.8mmol) was added in batches to the above reaction mixture, and the reaction was continued at 40°C for 2h. After the reaction was completed, the reaction mixture was cooled to 25°C and quenched by dropwise addition of water (100mL). The reaction mixture was extracted with dichloromethane (2x100mL). The combined dichloromethane layers were washed with saturated sodium bicarbonate (100 mL) solution, dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified by silica gel column chromatography using 5% ethyl acetate in hexane as the eluent to give 2,5-dibromo-3-(ethylthio)pyridine (5 g, 16.83 mmol, 61% yield). 1 H-NMR (400MHz, DMSO-d6) δ8.29(d,J=2.2Hz,1H),7.88(d,J=2.2Hz,1H),310(q,J=7.3Hz,2H),1.30(t,J=7.3Hz,3H); ESI MS(m / z)297.55,299.55[(MH) + Br 79,81 ]

[0386] Step-3: 5-Bromo-3-(ethylthio)-2-(tributylstannyl)pyridine

[0387] To a stirred solution of 2,5-dibromo-3-(ethylthio)pyridine (500mg, 1.69mmol) in anhydrous toluene (15mL), n-butyllithium (2.5M solution in n-hexane) (0.8mL, 2.02mmol) solution in anhydrous toluene (50mL) was added dropwise at -78 ° C over 15min. The reaction was stirred while the temperature was maintained at -78 ° C for 1 hour until the solution became dark red. Tri-n-butyltin chloride (0.55mL, 2.02mmol) was added dropwise to the above-mentioned reaction mixture, and the reaction was further stirred for 12h while the reaction was warmed to 25 ° C. After the reaction was completed, the reaction mixture was cooled to 0 ° C and quenched by dropwise addition of water (50mL). The reaction mixture was extracted with ethyl acetate (2x25mL). The combined ethyl acetate layers were washed with brine (50 mL) and water (100 mL), dried over anhydrous sodium sulfate and concentrated to give a crude product which was purified by silica gel column chromatography using 2% ethyl acetate in hexane as the eluent to give 5-bromo-3-(ethylthio)-2-(tributylstannyl)pyridine (200 mg, 0.39 mmol, 23% yield). 1 H-NMR (400MHz, DMSO-d6) δ8.61(q,J=2.0Hz,1H),7.93(td,J=6.7,2.2Hz,1H),3.06(q,J=7 .3Hz,2H),1.44-1.61(m,6H),1.20-1.31(m,9H),1.08-1.15(m,6H),0.83(t,J=7.3Hz,9H).

[0388] Example 3: Synthesis of 5-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 66)

[0389] Step 1: Synthesis of 5-(3-(ethylthio)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0390] To a stirred solution of 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) in a mixture of tetrahydrofuran (6 mL) and water (3 mL) was added sodium acetate (158 mg, 1.49 mmol) and tetrakis(triphenylphosphine)palladium(0) (25.8 mg, 0.02 mmol). The reaction mixture was thoroughly deoxygenated by three vacuum / nitrogen cycles and then heated at 85°C for 3 h. 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 and concentrated under reduced pressure to afford the crude product, which was purified by silica gel column chromatography using 10% ethyl acetate in hexanes as eluent to afford 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 (400MHz, DMSO-d6) δ9.33(dd,J=7.3,0.6Hz,1H),8.84(d,J=1.8Hz,1H),8.14(d,J=2.1Hz,1H),7 .97-8.03(m,3H),7.54(d,J=7.9Hz,2H),7.38(s,1H),3.15(q,J=7.4Hz,2H),1.27(t,J=7.3Hz,3H); ESI MS(m / z)485.00(MH) + .

[0391] Step 2: 5-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0392] 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 meta-chloroperbenzoic acid (166 mg, 0.58 mmol) in portions at 0-5°C. The reaction mixture was stirred at 25°C for 5 h. After completion of the reaction, the reaction mixture was cooled to 0°C and quenched by the 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 25% ethyl acetate in hexane as the eluent to give 5-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (80 mg, 0.16 mmol, 54% yield). 1 H-NMR (400MHz, DMSO-d6) δ9.48(dd,J=7.3,1.0Hz,1H),9.41(d,J=2.2Hz,1H),8.70(d,J=2.2Hz,1H),8.09(dt,J=9.5 ,2.6Hz,2H),7.72(d,J=7.3Hz,1H),7.60-7.62(m,2H),7.50(s,1H),3.97(q,J=7.4Hz,2H),1.33(t,J=7.3Hz,3H); ESI MS(m / z)516.95(MH) + .

[0393] 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)

[0394] Step-1: 6-Bromo-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0395] To a stirred solution of 3-(trifluoromethyl)-1H-pyrazol-5-amine (6.0 g, 39.70 mmol) in ethanol (180 mL) was added 2-bromomalondialdehyde (5.99 g, 39.70 mmol) in portions over a 15-min period at 25°C, 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 by half. The reaction mixture was cooled to 0°C and treated with saturated sodium bicarbonate solution (50 mL) while stirring for 30 minutes. The resulting 6-bromo-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine precipitate (8.0 g, 30.10 mmol, 76% yield) was filtered, washed with water (50 mL), and dried under reduced pressure. 1 H-NMR (400MHz, DMSO-d6) δ9.76 (s, 1H), 8.81 (s, 1H), 7.36 (s, 1H); ESI-MS (m / z) 266.02 (MH).

[0396] Step 2: 6-(6-chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0397] 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 three vacuum / nitrogen cycles, followed by the addition of 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 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 a crude product, which was purified by silica gel column chromatography using 10% ethyl acetate in hexane as eluent to obtain 6-(6-chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (3.0 g, 8.36 mmol, 45% yield). 1 H-NMR (400MHz, DMSO-d6) δ9.56(q,J=1.0Hz,1H),8.93(d,J=2.1Hz,1H),8.08(d,J=8.3Hz, 1H),7.64(d,J=8.3Hz,1H),7.40(s,1H),3.02(q,J=7.3Hz,2H),1.15(t,J=7.5Hz,3H); ESI MS(m / z)359.70,361.70[(MH)+ Cl 35,37 ].

[0398] Step 3: 6-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0399] To 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 meta-chloroperbenzoic acid (4.81 g, 16.72 mmol) in portions at 0-5°C. The reaction mixture was stirred at 25°C for 5 h. After completion of the reaction, the reaction mixture was cooled at 0°C and quenched by the 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 obtain the crude product, which was purified by silica gel column chromatography using 25% ethyl acetate in hexane as eluent to obtain 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. 1 H-NMR (400MHz, DMSO-d6) δ9.56(q,J=1.0Hz,1H),8.87(d,J=1.8Hz,1H),8.54(d,J=8.6Hz,1H),7.99(d,J=8.6Hz,1H),7.41(s,1H),3.26(q J=7.3Hz,2H),1.06(t,J=7.3Hz,3H); ESI MS(m / z)392.80,394.80[(MH) + Cl 35,37 ].

[0400] Step 4: 6-(3-(ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0401] To 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 silica gel column chromatography using 40% ethyl acetate in hexane 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, 16% yield). 1 H-NMR (400MHz, DMSO-d6) δ9.49 (dd, J=7.3, 0.6Hz, 1H), 9.35 (d, J=2.4Hz, 1H), 8.68(d,J=2.4Hz,1H),7.73(d,J=7.3Hz,1H),7.53(s,1H),6.94(s,1H),3.98(q J=7.3Hz,2H),2.54(s,3H),1.32(t,J=7.5Hz,3H); ESI MS(m / z)504.80(MH) +

[0402] Example 5: Synthesis of 6-(3-(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 57)

[0403] To a stirred solution of 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) in a mixture of tetrahydrofuran (3 mL) and water (3 mL) was added sodium carbonate (89 mg, 0.84 mmol) and tetrakis(triphenylphosphine)palladium(0) (14.59 mg, 0.01 mmol). The reaction mixture was thoroughly deoxygenated by three vacuum / nitrogen cycles and heated at 85° C. for 3 h. 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 give the crude product, which was purified by silica gel column chromatography using 20% ​​ethyl acetate in hexane as eluent to afford 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 H-NMR (400MHz, DMSO-d6) δ9.64(q,J=1.0Hz,1H),8.97(d,J=2.1Hz,1H),8.61(d,J=8.6Hz,1H),8.44(d,J=8.6Hz,1H),8 .37(dt,J=9.6,2.4Hz,2H),7.54(dd,J=8.9,0.9Hz,2H),7.42(s,1H),3.31(q,J=7.3Hz,2H),1.09(t,J=7.3Hz,3H); ESI MS(m / z)517.00(MH) +

[0404] Example 6: Synthesis of 6-chloro-3-(ethylthio)-2-(tributylstannyl)pyridine (Intermediate 3) in Example 4

[0405] Step-1: 6-Chloro-3-(ethylthio)-2-(tributylstannyl)pyridine

[0406] To a stirred solution of 2-bromo-6-chloro-3-(ethylthio)pyridine (8.0 g, 31.7 mmol) in anhydrous toluene (160 mL), n-butyl lithium (2.5 M solution in n-hexane) (20.60 mL, 41.2 mmol) was added dropwise at -78 ° C over a 15 min period. The reaction was stirred while the temperature was maintained at -78 ° C for 1 h until the solution became dark red. Tri-n-butyltin chloride (11.20 mL, 41.2 mmol) was added dropwise to the above reaction mixture, and the reaction was stirred for 12 h while the reaction was warmed to 25 ° C. After the reaction was complete, 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 × 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 afford crude 6-chloro-3-(ethylthio)-2-(tributylstannyl)pyridine (10 g, 21.61 mmol, 68% yield), which was used in the next step without any further purification. ESI MS (m / z) 462.70.80, 463.80 [(MH) + Cl 35,37 ].

[0407] 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)

[0408] Step 1: 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0409] 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, 9.10 mmol) in anhydrous tetrahydrofuran (50 mL) was thoroughly deoxygenated by three vacuum / nitrogen cycles, followed by the addition of tetrakis(triphenylphosphine)palladium(0) (1.17 g, 1.01 mmol) and copper(I) bromide (290 mg, 2.02 mmol). The reaction mixture was heated at 70 ° C for 1 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 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 25% ethyl acetate in hexane as eluent to afford 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 H-NMR (400MHz, DMSO-d6) δ9.48(dd,J=7.3,1.0Hz,1H),8.53(d,J=8.6Hz,1H),8.03(d,J=8.6 Hz,1H),7.67(d,J=7.5Hz,1H),7.51(s,1H),3.87(q,J=7.4Hz,2H),1.28(t,J=7.5Hz,3H); ESI MS(m / z)390.85,392.85[(MH) + Br 79,81 ].

[0410] 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

[0411] To a stirred solution of 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) in anhydrous dimethyl sulfoxide (2 mL) was added potassium carbonate (120 mg, 0.90 mmol). The reaction mixture was stirred at 100 ° C for 2 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 silica gel column chromatography using 40% ethyl acetate in hexane as 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 H-NMR (400MHz, DMSO-d6) δ9.93(d,J=1.0Hz,1H),9.58(dd,J=7.3,0.7Hz,1H),8.80(d,J=8.6Hz,1H),8.34(d,J= 8.6Hz,1H),7.95(d,J=7.3Hz,1H),7.57(s,1H),3.97-4.06(m,2H),1.33(t,J=7.5Hz,3H); ESI-MS(m / z)492(MH) + .

[0412] Example 8: Synthesis of 5-(6-(4-chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 20)

[0413] 5-(6-(4-chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0414] 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, 0.50 mmol) in a mixture of 1,4-dioxane (4 mL) and water (1 mL) was added sodium carbonate (102 mg, 0.96 mmol) and tetrakis(triphenylphosphine)palladium(0) (22.18 mg, 0.02 mmol). The reaction mixture was thoroughly deoxygenated by three vacuum / nitrogen cycles and heated at 100°C for 2 h. 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 and concentrated under reduced pressure to afford the crude product, which was purified by silica gel column chromatography using 20% ​​ethyl acetate in hexane as eluent to afford 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 H-NMR (400MHz, DMSO-d6) δ9.47(dd,J=7.3,1.0Hz,1H),8.55(d,J=8.6Hz,1H),8.44(d,J=8.3Hz,1H),8.26-8.29(m,2 ESI MS(m / z)466.85,47.85.00[(MH) + Cl 35,37 ].

[0415] Example 9: Synthesis of 6-chloro-3-(ethylsulfonyl)-2-(tributylstannyl)pyridine (Intermediate-5) in Example 7

[0416] Step-1: 6-chloro-3-(ethylsulfonyl)-2-(tributylstannyl)pyridine

[0417] To a stirred solution of 2-bromo-6-chloro-3-(ethylsulfonyl)pyridine (2.0g, 7.03mmol) in anhydrous toluene (160mL), n-butyllithium (2.5M solution in n-hexane) (5.30mL, 10.54mmol) was dropwise added at -78°C in a 15min period. The reaction mixture was stirred while the temperature was maintained at -78°C for 1h until the solution became crimson. Tri-n-butyltin chloride (3.80mL, 14.06mmol) was dropwise added to the above-mentioned reaction mixture, the reaction was stirred for 12h, while the reaction was warmed to 25°C. After the reaction was complete, the reaction mixture was cooled to 0°C and quenched by dropwise addition of water (50mL). The reaction mixture was extracted with ethyl acetate (2x50mL). The combined ethyl acetate layers were washed with brine (100 mL) and water (100 mL), dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified by silica gel column chromatography using 20% ​​ethyl acetate in hexane as eluent to give 6-chloro-3-(ethylsulfonyl)-2-(tributylstannyl)pyridine (1.3 g, 2.63 mmol, 37% yield). 1 H-NMR (400MHz, DMSO-d6) δ8.27(dd,J=8.2,1.3Hz,1H),7.66(dd,J=8.2,1.3Hz,1H),3.36(q,J=7.4H z,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) + Cl 35,37 ].

[0418] 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)

[0419] Step 1: 5-(6-chloro-5-(ethylthio)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0420] A stirred solution of 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, 26.30 mmol) in anhydrous tetrahydrofuran (100 mL) was thoroughly deoxygenated by three vacuum / nitrogen cycles, followed by the addition of 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 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 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 15% ethyl acetate in hexane as eluent to afford 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. 1 H-NMR (400MHz, DMSO-d6) δ9.45(dd,J=7.5,0.9Hz,1H),8.97(d,J=2.2Hz,1H),8.40(d,J=2.2 Hz,1H),8.07(d,J=7.6Hz,1H),7.38(s,1H),3.22(q,J=7.3Hz,2H),1.35(t,J=7.3Hz,3H); ESI MS(m / z)358.95,360.70[(MH) + Cl 35,37 ].

[0421] Step 2: 5-(6-chloro-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0422] 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 meta-chloroperbenzoic acid (4.80 g, 16.72 mmol) in portions at 0-5 ° C. The reaction mixture was stirred at 25 ° C. for 5 h. After the reaction mixture was completed, the reaction mixture was cooled to 0 ° C. and 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 obtain the crude product, which was purified by silica gel column chromatography using 30% ethyl acetate in hexane as eluent to obtain 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. 1 H-NMR (400MHz, DMSO-d6) δ9.56(d,J=2.1Hz,1H),9.50(dd,J=7.5,0.8Hz,1H),9.11(d,J=2.4H z,1H),8.14(d,J=7.6Hz,1H),7.49(s,1H),3.65(q,J=7.4Hz,2H),1.21(t,J=7.5Hz,3H)); ESI MS(m / z)390.95,392.95[(MH) + Cl 35,37 ].

[0423] Step 3: 5-(5-(ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

[0424] To a stirred solution of 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) in anhydrous N,N-dimethylformamide (3 mL) 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 mixture, 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 give a crude product which was purified by silica gel column chromatography using 40% ethyl acetate in hexane as 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). 1 H-NMR (400MHz, DMSO-d6) δ9.78(d,J=2.2Hz,1H),9.57(dd,J=7.3,1.0Hz,1H),9.29(d,J=2.2Hz,1H),8.25(d,J =7.6Hz,1H),7.55(s,1H),6.91(s,1H),3.76(q,J=7.3Hz,2H),2.36(d,J=0.7Hz,3H),1.27(t,J=7.3Hz,3H); ESI MS(m / z)504.75(MH) + .

[0425] Example 11: Synthesis of 2-chloro-3-(ethylthio)-5-(tributylstannyl)pyridine (Intermediate-2) in Example 10 Step-1: 2-chloro-3-(ethylthio)-5-(tributylstannyl)pyridine

[0426] To the stirred solution of 5-bromo-2-chloro-3-(ethylmercapto)pyridine (2.0g, 7.92mmol) in anhydrous toluene (40mL), n-butyllithium (1.6M solution in n-hexane) (6.0mL, 9.50mmol) was added dropwise at -78 DEG C in the 15min period. The reaction mixture was stirred while the temperature was maintained at -78 DEG C for 1h, until the solution became dark red. Tri-n-butyltin chloride (2.60mL, 9.50mmol) was added dropwise into the above-mentioned reaction mixture, the stirring reaction was 12h, while the reaction was warming to 25 DEG C. After the reaction was completed, the reaction mixture was cooled to 0 DEG C, and quenched by adding water (50mL). The reaction mixture was extracted with ethyl acetate (2x50mL). The combined ethyl acetate layers were washed with brine (100 mL) and water (100 mL), dried over anhydrous sodium sulfate and concentrated to obtain the crude product, which was purified by silica gel column chromatography using 20% ​​ethyl acetate in hexane as eluent to obtain crude 2-chloro-3-(ethylthio)-5-(tributylstannyl)pyridine (1.5 g, 3.24 mmol, 41% yield), which was used in the next step without any further purification.

[0427] 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)

[0428] Step 1: 6-Bromo-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine

[0429] To a stirred solution of 3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (1 g, 6.58 mmol) in ethanol (30 mL) was added 2-bromomalondialdehyde (1.0 g, 6.58 mmol) in portions over a 15-min period at 25°C, followed by the dropwise addition of concentrated hydrochloric acid (0.8 mL). The reaction was stirred at 25°C for 12 h. After completion of the reaction, the reaction volume was reduced by half. The reaction mixture was cooled to 0°C and treated with saturated sodium bicarbonate solution (50 mL) while stirring for 30 min. The resulting precipitate of 6-bromo-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (1.4 g, 5.24 mmol, 80% yield) was filtered, washed with water (20 mL), and dried under vacuum. 1 H-NMR (400MHz, DMSO-d6) δ10.06 (d, J = 2.4 Hz, 1H), 9.18 (d, J = 2.4 Hz, 1H).

[0430] Step 2: 6-(6-chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine

[0431] 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). 1 H-NMR (400MHz, DMSO-d6) δ9.88(d,J=2.4Hz,1H),9.29(d,J=2.4Hz,1H),8.12(d,J= 8.6Hz,1H),7.67(d,J=8.3Hz,1H),3.01(q,J=7.2Hz,2H),1.16(t,J=7.3Hz,3H),ESI MS(m / z)359.80(MH) + .

[0432] Step 3: 6-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine

[0433] 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, 37% yield) was prepared from 6-(6-chloro-3-(ethylsulfanyl)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(400MHz,DMSO-d6)δ9.84-9.85(m,1H),9.22-9.23(m,1H),8.54-8.57 (m,1H),8.01-8.04(m,1H),3.25(q,J=7.3Hz,2H),1.04(t,J=7.3Hz,3H),ESI MS(m / z)391.80(MH) + .

[0434] 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

[0435] The title compound 6-(3-(ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl-1,2,4-triazol-1-pyridine-2-pyridin-2-yl)-2-(trifluoromethyl)-1,2,4-triazolo[1,5-a]pyrimidine (95 mg, 0.224 mmol, 35% yield) 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 (400MHz, DMSO-d6) δ9.95(d,J=2.1Hz,1H),9.56(s,1H),9.37(d,J=2.4Hz,1H),8.78(d,J= 8.6Hz,1H),8.45(s,1H),8.24(d,J=8.6Hz,1H),3.28(q,J=7.3Hz,2H),1.06(t,J=7.3Hz,3H),ESI MS(m / z)424.95(MH) + .

[0436] 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)

[0437] 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, 45% yield) 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). 1H-NMR (400MHz, DMSO-d6) δ9.94(d,J=2.4Hz,1H),9.33(d,J=2.2Hz,1H),8.62(d,J=8.6Hz,1H),8.46(d,J=8.6 Hz,1H),8.37(dd,J=6.8,2.2Hz,2H),7.56(d,J=8.1Hz,2H),3.28(q,J=7.3Hz,2H),1.07(t,J=7.3Hz,3H),ESI MS(m / z)517.90(MH) + .

[0438] 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)

[0439] Step 1: 6-(6-chloro-5-(ethylthio)pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine

[0440] 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 H-NMR (400MHz, DMSO-d6) δ9.88(d,J=2.4Hz,1H),9.29(d,J=2.4Hz,1H),8.12(d,J= 8.6Hz,1H),7.67(d,J=8.3Hz,1H),3.01(q,J=7.2Hz,2H),1.16(t,J=7.3Hz,3H),ESI MS(m / z)359.80(MH) + .

[0441] Step 2: 6-(6-chloro-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine

[0442] 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-(ethylsulfanyl)pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (780 mg, 2.17 mmol) using the reaction conditions described in step 3 of compound 9 (Example 4). 1 H-NMR (400MHz, DMSO-d6) δ9.84-9.85(m,1H),9.22-9.23(m,1H),8.54-8.57(m,1H),8.01-8.04(m,1H),3.25(q,J=7.3Hz,2H),1.04(t,J=7.3Hz,3H).

[0443] Step 3: Synthesis of 6-(5-(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine

[0444] 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, 39% yield) 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 (400MHz, DMSO-d6) δ10.25(d,J=2.4Hz,1H),9.63(d,J=2.4Hz,1H),9.44(d,J=2.1Hz,1H),8.89(d,J=2. 1Hz,1H),7.72(dt,J=9.3,2.4Hz,2H),7.50(d,J=7.9Hz,2H),3.18(q,J=7.4Hz,2H),1.07(t,J=7.3Hz,3H),ESI MS(m / z)517.75(MH) + .

[0445] 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)

[0446] a) Step-1: 2-(Trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one

[0447] To a stirred solution of 3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine (15 g, 99.0 mmol) in anhydrous N,N-dimethylformamide (100 mL), a solution of (E)-3-ethoxyacrylate (28.7 mL, 197.00 mmol) in anhydrous N,N-dimethylformamide (5 mL) was added dropwise at room temperature over a 15 min period, followed by the addition of potassium carbonate (34.1 g, 247.0 mmol). The reaction was heated at 100 ° C for 16 h. 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 dropwise addition of acetic acid (15 mL) at 0 ° C and then further stirred at room temperature for 2 h. The resulting mixture was extracted with ethyl acetate (2x200 mL), and the combined ethyl acetate layers were washed with water (100 mL), brine (200 mL), dried over anhydrous sodium sulfate, filtered and concentrated to obtain the crude product, which was purified by silica gel CombiFlash system using 60% ethyl acetate in hexane as eluent to obtain 2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one (10 g, 49.0 mmol, 49.70% yield). 1 HNMR(400MHz, DMSO-d6)δ8.66(d,J=7.9Hz,1H),6.32(d,J=7.6Hz,1H); ESI MS(m / z)204.90(MH) + .

[0448] b) Step-2: 5-Bromo-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine

[0449] 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 was added phosphorus(V)oxybromide (42.1 g, 147.0 mmol). The reaction mixture was heated at 100° C. for 5 h. After the reaction was complete, the reaction mixture was cooled to room temperature and diluted with water (200 mL). The aqueous layer was extracted with ethyl acetate (2x200 mL), and the combined ethyl acetate layers were washed with saturated sodium bicarbonate solution (200 mL), water (100 mL), brine (100 mL), dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified on a silica gel CombiFlash system using 10% ethyl acetate in hexane 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 (400MHz, DMSO-d6) δ9.49 (q, J = 2.4Hz, 1H), 7.85 (d, J = 7.1Hz, 1H).

[0450] c) Step-3: 5-(5-bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 90)

[0451] 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 of compound 38 (Example 1). 1 H-NMR (400MHz, DMSO-d6) δ9.31(dd,J=7.3,0.9Hz,1H),8.63(d,J=1.8Hz,1H),8.15(d,J=1.8 Hz,1H),7.87(d,J=7.3Hz,1H),7.37(s,1H),3.05(q,J=7.3Hz,2H),1.23(t,J=7.3Hz,3H); ESI MS(m / z)404.70,405.70[(MH) + Br 79,81 ].

[0452] d) Step-4: 5-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 99)

[0453] 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-(ethylsulfanyl)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). 1 H-NMR (400MHz, DMSO-d6) δ9.45(dd,J=7.3,0.9Hz,1H),9.22(d,J=2.1Hz,1H),8.65(d,J=2.1 Hz,1H),7.65(d,J=7.3Hz,1H),7.49(s,1H),3.93(q,J=7.4Hz,2H),1.29(t,J=7.5Hz,3H); ESI MS(m / z)434.65,435.65[(MH) + Br 79,81 ].

[0454] 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)

[0455] To a stirred solution of 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) in toluene (10 mL) was added tripotassium phosphate (365 mg, 1.71 mmol) and 2-di-tert-butylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl (146 mg, 0.034 mmol). The reaction mixture was thoroughly deoxygenated by three vacuum / nitrogen cycles, then tris(dibenzylideneacetone)dipalladium(0) (315 mg, 0.035 mmol) was added and 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 afford the crude product, which was purified on a silica gel CombiFlash system using 60% ethyl acetate in hexanes as eluent to afford 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, 20.08% yield) as a solid. 1 H-NMR (400MHz, DMSO-d6) δ9.92-9.78(m,2H),9.64(d,J=2.4Hz,1H),8.94(d,J=2 .1Hz,1H),8.04(d,J=7.0Hz,1H),4.01(q,J=7.3Hz,2H),1.34(t,J=7.5Hz,3H)ESI MS(m / z)493.00(MH) + .

[0456] Example 16: Synthesis of 5-(6-cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 180)

[0457] a) Step-1: 5-(6-chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 165)

[0458] 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 (400MHz, DMSO-d6) δ9.59 (d, J=7.1Hz, 1H), 8.19-8.15 (m, 1H), 8.10 (d, J= 8.8Hz,1H),7.70(d,J=8.6Hz,1H),3.05(q,J=7.3Hz,2H),1.27-1.22(m,3H)ESI MS(m / z)360,362[(MH) + Cl 35,37 ].

[0459] a) Step-4: 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 169)

[0460] 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-(ethylsulfanyl)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 H-NMR (400MHz, DMSO-d6) δ9.77(d,J=7.1Hz,1H),8.54(d,J=8.3Hz,1H),8.06(d,J= 8.6Hz,1H),7.97(d,J=7.1Hz,1H),3.86(q,J=7.4Hz,2H),1.27(t,J=7.5Hz,3H)ESI MS(m / z)392,394[(MH) + Cl 35,37 ].

[0461] 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)

[0462] To a stirred solution of 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) in a mixture of dioxane (8 mL) and water (2 mL) was added tripotassium phosphate (406 mg, 1.92 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (52.1 mg, 0.06 mmol) in sequence. The reaction mixture was thoroughly deoxygenated by three vacuum / nitrogen cycles and heated at 110°C for 3 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, filtered, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product, which was purified by a silica gel CombiFlash system using 25% ethyl acetate in hexane as 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 H-NMR (400MHz, DMSO-d6) δ9.71(d,J=7.1Hz,1H),8.32(d,J=8.3Hz,1H),7.94(d,J=7.1Hz,1H),7.80(d ,J=8.6Hz,1H),3.83(q,J=7.4Hz,2H),2.41-2.34(m,1H),1.25(t,J=7.5Hz,3H),1.18-1.09(m,4H)ESI MS(m / z)397.55(MH) + .

[0463] Example 17: Synthesis of 5-(3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 152)

[0464] Step-1: 5-(3-(Ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 153)

[0465] 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 in the next step without purification.

[0466] 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 g, 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 (400MHz, DMSO-d6) δ9.57(d,J=7.3Hz,1H),8.57(dd,J=4.4,1.4Hz,1H),8.24(d,J=7.3Hz,1H) ,8.05(dd,J=8.3,1.2Hz,1H),7.58(q,J=4.3Hz,1H),3.03(q,J=7.3Hz,2H),1.25(t,J=7.3Hz,3H)ESI MS(m / z)325.90(MH) + .

[0467] Step-2: 5-(3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 152)

[0468] 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% yield) 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 (400MHz, DMSO-d6) δ9.92-9.78(m,2H),9.64(d,J=2.4Hz,1H),8.94(d,J=2 .1Hz,1H),8.04(d,J=7.0Hz,1H),4.01(q,J=7.3Hz,2H),1.34(t,J=7.5Hz,3H)ESI MS(m / z)493(MH) + .

[0469] Example 18: Synthesis of 5-(5-(cyclopropylmethoxy)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 161):

[0470] 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

[0471] To a stirred solution of 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) in dioxane (8 mL) under a nitrogen atmosphere was added potassium acetate (0.90 g, 9.17 mmol) followed by [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.19 g, 0.23 mmol). The reaction mixture was thoroughly deoxygenated by three vacuum / nitrogen cycles and heated at 90°C for 1 hour. 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, filtered, and concentrated under reduced pressure to give a crude product, which was purified on a silica gel CombiFlash system using 30% ethyl acetate in hexane as 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). ESI MS (m / z) 481.75 (MH) - .

[0472] Step-2: Synthesis of 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-ol (Compound 109)

[0473] To 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 hydrogen peroxide (7.93 mL, 78 mmol) dropwise 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, filtered, and concentrated under reduced pressure to give the crude product, which was purified using a silica gel CombiFlash system using 50% ethyl acetate in hexane as 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 H-NMR (400MHz, DMSO-d6) δ11.47(s,1H),9.66(d,J=7.1Hz,1H),8.57(d,J=2.4Hz,1H),7.9 2(d,J=7.1Hz,1H),7.85(d,J=2.4Hz,1H),3.98(q,J=7.4Hz,2H),1.29(t,J=7.5Hz,3H)ESI MS(m / z)373.85(MH) + .

[0474] Step-3: Synthesis of 5-(5-(cyclopropylmethoxy)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 161)

[0475] To a stirred solution of 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) in anhydrous N,N-dimethylformamide (2 mL) was added cesium carbonate (349 mg, 1.07 mmol). The reaction mixture was stirred at room temperature for 12 hours. 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), and the combined ethyl acetate layers were separated, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give the crude product, which was purified on a silica gel CombiFlash system using 20% ​​ethyl acetate in hexane as the 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 H-NMR (400MHz, DMSO-d6) δ9.68(d,J=7.1Hz,1H),8.78(d,J=2.7Hz,1H),7.94-7.92(m,2H),4.15(d, J=7.1Hz,2H),3.97(q,J=7.4Hz,2H),1.30(t,J=7.5Hz,4H),0.65-0.61(m,2H),0.43-0.40(m,2H)ESI MS(m / z)428.15(MH) + .

[0476] Example 19: Synthesis of 2-(5-(3,5-difluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine (Compound 122):

[0477] Step-1: Synthesis of 5-bromo-3-(ethylthio)pyridinecarbonitrile

[0478] To the stirred solution of 5-bromo-3-fluoropyridine nitrile (10g, 49.8mmol) in tetrahydrofuran (100mL), under nitrogen atmosphere, sodium hydride (1.2g, 49.8mmol) was added at -15 ° C, then ethyl mercaptan (3.1g, 49.8mmol) was added dropwise at the same temperature. At room temperature, reaction mixture was stirred for 16h. After the reaction was complete, reaction mixture was quenched with frozen water (500mL) and extracted with ethyl acetate (2x500mL). The ethyl acetate layer merged was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product, which was purified by silica gel CombiFlash system using a hexane solution of 10% ethyl acetate as eluent. The bromo-3-fluoropyridine nitrile (12g, 49.4mmol, 99% yield) was obtained. 1 H-NMR (400MHz, CHCl3-d) δ8.49 (d, J = 2.1Hz, 1H), 7.84-7.82 (m, 1H), 3.07 (q, J = 7.4Hz, 2H), 1.41 (t, J = 7.5Hz, 3H); ESI MS (m / z) 242.95 (MH)+.

[0479] Step-2: Synthesis of 5-bromo-3-(ethylthio)pyridine amidine hydrochloride

[0480] At 0 ℃, under nitrogen, to a stirred solution of 5-bromo-3-(ethylthio)pyridine carbonitrile (10g, 41.1mmol) in methanol (500mL), sodium methoxide (2.22g, 41.1mmol) was added. The reaction mixture was stirred at room temperature for 16 hours. Then ammonium chloride (2.20g, 41.1mmol) was added to the reaction mixture and stirred at room temperature for 1 hour, and then refluxed for 6 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure, and diluted with ethyl acetate. The obtained white solid was filtered and dried under reduced pressure to obtain 5-bromo-3-(ethylthio)pyridine amidine hydrochloride (5.0g, 16.86mmol, 41.0% yield). 1 H-NMR (400MHz, DMSO-d6) δ9.56 (s, 3H), 8.66 (d, J = 2.0Hz, 1H), 8.35-8.34 (m, 1H), 3.16-3.09 (m, 2H), 1.22 (t, J = 7.2Hz, 3H); ESI MS (m / z) 260 (MH)+.

[0481] Step-3: Synthesis of 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-5-nitropyrimidin-4(3H)-one

[0482] To a stirred solution of 5-bromo-3-(ethylthio)pyridinamidine hydrochloride (5 g, 16.9 mmol) and (E)-ethyl 3-(dimethylamino)-2-nitroacrylate (3.2 g, 16.9 mmol) in methanol (50 mL) 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 on a silica gel CombiFlash system using 10% methanol in dichloromethane as 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 (400MHz, DMSO-d6) δ13.61(s,1H),8.91(s,1H),8.62(d,J=1.8Hz,1H),8.17(d,J=1.8Hz,1H),3.06(q,J=7.3Hz,2H),1.24(t,J=7.3Hz,3H); ESI MS(m / z)358.8(MH)+.

[0483] Step-4: Synthesis of 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-4-chloro-5-nitropyrimidine

[0484] Phosphorus oxychloride (POCl3) (39.3 mL, 420 mmol) was added to 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-5-nitropyrimidin-4(3H)-one (7.5 g, 21.0 mmol) at 0°C. The reaction mixture was warmed to room temperature and then heated at 100°C for 3 h. After completion of the reaction, the excess phosphorus oxychloride (POCl3) was evaporated under reduced pressure; the reaction mixture was diluted with ice water (200 ml) and neutralized with saturated aqueous sodium bicarbonate 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 the crude product, which was purified on a silica gel CombiFlash system using 50% ethyl acetate in hexane as the eluent to obtain 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-4-chloro-5-nitropyrimidine (5 g, 13.3 mmol, 63.4% yield). 1 H-NMR (400MHz, DMSO-d6) δ 8.93 (s, 1H), 8.64 (d, J = 2.0Hz, 1H), 8.19 (d, J = 2.0Hz, 1H), 3.09-3.03 (m, 2H), 1.26-1.21 (m, 3H); ESI MS (m / z) 376.8 (MH)+.

[0485] Step-5: Synthesis of 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-N-methyl-5-nitropyrimidin-4-amine

[0486] To a stirred solution of 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-4-chloro-5-nitropyrimidine (4.5 g, 12 mmol) in 1,4-dioxane (45 mL) at 0 ° C. under nitrogen was added a solution of methylamine (30 mL, 60 mmol) in tetrahydrofuran. 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-nitropyrimidine-4-amine (4.4 g, 11.9 mmol, 99% yield). 1 H-NMR (400MHz, DMSO-d6) δ9.20 (s, 1H), 8.99 (d, J = 4.4Hz, 1H), 8.56 (d, J = 2.0Hz, 1H), 8. 13(d,J=2.0Hz,1H),3.10(d,J=4.9Hz,3H),3.03(q,J=7.3Hz,2H),1.22-1.16(m,3H); ESI MS(m / z)369.9(MH)+.

[0487] Step-6: Synthesis of 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-N4-methylpyrimidine-4,5-diamine

[0488] To a stirred solution of 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-N-methyl-5-nitropyrimidin-4-amine (5 g, 13.5 mmol) in ethanol (50 mL) and water (50 mL) was added iron powder (7.5 g, 135 mmol) followed by ammonium chloride (7.2 g, 135 mmol). The reaction mixture was heated at 80 ° C for 16 h. After the reaction was complete, 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 obtain 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 was used directly in the next step. ESI MS (m / z) 341.9 (MH) +.

[0489] Step-7: Synthesis of 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine (Compound 112)

[0490] At room temperature, trifluoroacetic anhydride (33.2 mL, 235 mmol) was added to 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-N4-methylpyrimidine-4,5-diamine (4 g, 11.76 mmol). The reaction mixture was heated at 50 ° C for 20 h. After the reaction was completed, the reaction mixture was concentrated under reduced pressure and diluted with ice water (200 mL). The reaction mixture was alkalized with 1N NaOH aqueous solution and extracted with ethyl acetate (2x150 mL). The combined ethyl acetate layer was dried over anhydrous sodium sulfate, filtered and concentrated to obtain a crude product, which was purified by a silica gel column CombiFlash system using a hexane solution of 30% ethyl acetate as an eluent to obtain 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 H-NMR (400MHz, DMSO-d6) δ9.52(s,1H),8.60(d,J=2.0Hz,1H),8.18(d,J=2.0H z,1H),3.98(d,J=1.0Hz,3H),3.03(q,J=7.4Hz,2H),1.16(t,J=7.3Hz,3H); ESI MS(m / z)419.8(MH)+.

[0491] Step-8: Synthesis of 2-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine (Compound 113)

[0492] 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-(ethylsulfanyl)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). 1 H-NMR (400MHz, DMSO-d6) δ9.54(s,1H),9.18(d,J=2.4Hz,1H),8.63(d,J=2.1H z,1H),3.98(d,J=1.2Hz,3H),3.83(q,J=7.4Hz,2H),1.25(t,J=7.3Hz,3H); ESI MS(m / z)450(MH)+.

[0493] Step-9: 2-(5-(3,5-difluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine (Compound 122)

[0494] 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) under nitrogen was added (3,5-difluorophenyl)boronic acid (70.1 mg, 0.44 mmol) and potassium carbonate (135 mg, 0.98 mmol). 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloromethane complex (36.3 mg, 0.045 mmol) was added to the reaction mixture, which was 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 give the crude product, which was purified by silica gel column CombiFlash system using 50% ethyl acetate in hexane as 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. 1 H-NMR (400MHz, DMSO-d6) δ9.55(s,1H),9.37(d,J=2.2Hz,1H),8.68(d,J=2.2Hz,1H),7.82-7.78(m,2 H),7.43(tt,J=9.3,2.3Hz,1H),4.04-3.99(m,3H),3.83(q,J=7.4Hz,2H),1.28(t,J=7.5Hz,3H); ESI MS(m / z)484.05(MH)+.

[0495] Example 20: Synthesis of (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)(imino)(methyl)-16-sulfoxide (Compound 200)

[0496] Step-1: Synthesis of 5-(3-(ethylsulfonyl)-6-(methylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 195)

[0497] To a stirred solution of 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Step-1; Example 7) (600 mg, 1.53 mmol) in anhydrous N,N-dimethylformamide (4 mL) at 0°C, an aqueous solution of sodium thiomethoxide (0.46 mL, 1.38 mmol) was added dropwise over 15 minutes. The reaction mixture was allowed to warm to room temperature and further stirred for 2 hours. After completion of the reaction, the reaction 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 20% ​​ethyl acetate in hexane as eluent to obtain 5-(3-(ethylsulfonyl)-6-(methylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (400 mg, 0.99 mmol, 64.7% yield). 1 H-NMR (400MHz, DMSO-d6) δ9.45-9.42(m,1H),8.24-8.22(m,1H),7.74(d,J=8.6Hz,1H),7.69(d,J =7.3Hz,1H),7.45(d,J=6.1Hz,1H),3.82(q,J=7.4Hz,2H),2.62(s,3H),1.25(t,J=7.3Hz,3H); ESI MS(m / z)402.90(MH) + .

[0498] Step-2: Synthesis of (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)(imino)(methyl)-16-sulfoxide (Compound 200)

[0499] To a stirred solution of 5-(3-(ethylsulfonyl)-6-(methylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (400 mg, 0.99 mmol) in methanol (15 mL) was added ammonium carbamate (233 mg, 2.98 mmol) in portions, followed by iodosobenzene diacetate (640 mg, 1.99 mmol) under cooling at 0 ° C. After the addition was complete, the reaction mixture was warmed to room temperature and further stirred for 15 h. After the reaction was complete, the reaction mixture was diluted with ice water (150 mL) and extracted with dichloromethane (2x50 mL). The combined dichloromethane layers were dried over anhydrous sodium sulfate, filtered and concentrated to obtain the crude product, which was purified by silica gel column chromatography using 90% ethyl acetate in hexane as the eluent to obtain (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)(imino)(methyl)-16-sulfoxide (70 mg, 0.16 mmol, 16.25% yield). 1 H-NMR (400MHz, DMSO-d6) δ9.51(dd,J=7.3,0.7Hz,1H),8.80(d,J=8.3Hz,1H),8.44(d,J=8.3Hz,1H),7.77(d,J=7 .1Hz,1H),7.54(s,1H),4.88(s,1H),4.02-3.93(m,2H),3.29(d,J=1.2Hz,3H),1.23(dt,J=51.4,7.2Hz,3H); ESI MS(m / z)434.30(MH) + .

[0500] Example 21: Synthesis of 5-(3-(ethylsulfonyl)-6-(methylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 196)

[0501] 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) following the reaction conditions described in Step 4 of compound 38 (Example 1). 1H-NMR (400MHz, DMSO-d6) δ9.52(dd,J=7.3,0.7Hz,1H),8.85(d,J=8.1Hz,1H),8.46(d,J=8.3Hz,1H) ,7.80(d,J=7.3Hz,1H),7.56(s,1H),3.97(q,J=7.4Hz,2H),3.44(s,3H),1.30(t,J=7.5Hz,3H); ESI MS(m / z)434.95(MH) + .

[0502] Example 22a: Synthesis of 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetonitrile (Compound 217)

[0503] 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)

[0504] 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 the solution, followed by stirring at the same temperature for 15 min, followed by the addition of 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Step-1; Example 7) (600 mg, 1.54 mmol). After the addition was complete, the reaction mixture was warmed to room temperature and stirred for a further 12 h. The reaction mixture was then diluted with an ice-cold saturated solution of ammonium chloride (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 give the crude product, which was purified by silica gel column chromatography using 40% ethyl acetate in hexane as eluent to give tert-butyl 2-cyano-2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetate (500 mg, 1.01 mmol, 65.7% yield). 1H-NMR (400MHz, DMSO-d6) δ13.92(s,1H),9.55(d,J=6.1Hz,1H),8.10(d,J=9.5Hz,1H),7.78(d,J=7.6Hz ,1H),7.59(s,1H),7.37(d,J=9.5Hz,1H),3.56(q,J=7.2Hz,2H),1.44(s,9H),1.20(t,J=7.3Hz,3H); ESI MS(m / z)494.30(MH) - .

[0505] Step-2: Synthesis of 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetonitrile (Compound 217)

[0506] 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 the reaction was complete, trifluoroacetic acid (TFA) was evaporated to give a 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 silica gel column chromatography using 40% ethyl acetate in hexane as eluent to afford 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 H-NMR (400MHz, DMSO-d6) δ9.46(dd,J=7.3,0.7Hz,1H),8.55(d,J=8.3Hz,1H),7.88(d,J=8.3Hz,1H) ,7.62(d,J=7.1Hz,1H),7.48(s,1H),4.51(s,2H),3.86(q,J=7.4Hz,2H),1.24(t,J=7.3Hz,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) was obtained as a by-product during the synthesis. 1H-NMR (400MHz, DMSO-d6) δ9.43(dd,J=7.3,1.0Hz,1H),8.44(d,J=8.3Hz,1H),7.89(s,1H),7.78(d,J=8.3 Hz,1H),7.57(d,J=7.3Hz,1H),7.45(s,1H),3.84(q,J=7.3Hz,2H),1.10(S,9H),1.11(t,J=7.3Hz,3H); ESI MS(m / z)470.05(MH) + (Compound 225)

[0507] Example 23: Synthesis of N-(ethyl(oxo)(5-(4-(trifluoromethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-16-sulfanylidene)cyanamide (Compound 199)

[0508] Step-1: Synthesis of ethyl(imino)(5-(4-(trifluoromethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-16-sulfoxide (Compound 98)

[0509] The title compound, ethyl(imino)(5-(4-(trifluoromethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-16-sulfoxide (460 mg, 0.89 mmol, 43.2% yield), 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). 1 H-NMR (400MHz, DMSO-d6) δ9.42(dd,J=7.3,1.0Hz,1H),9.28(d,J=2.2Hz,1H),8.65(d,J=2.2Hz,1H),8.04(dd,J=6.6, 2.2Hz,2H),7.58(dd,J=11.9,7.7Hz,3H),7.41(s,1H),4.46(s,1H),3.71(q,J=7.3Hz,2H),1.25(t,J=7.5Hz,3H); ESI MS(m / z)516.10(MH) + .

[0510] Step-2: Synthesis of N-(ethyl(oxo)(5-(4-(trifluoromethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-16-sulfanylidene)cyanamide (Compound 199)

[0511] To a stirred solution of ethyl(imino)(5-(4-(trifluoromethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-16-sulfoxide (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 h. 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 give the crude product, which was purified on a silica gel CombiFlash system using 40% ethyl acetate in hexane 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)-16-sulfanyl)cyanamide (140 mg, 0.26 mmol, 44.5% yield). 1 H-NMR (400MHz, DMSO-d6) δ9.55-9.52(m,2H),8.80(d,J=2.0Hz,1H),8.11(dd,J=6.8,2.2Hz,2H),7.84(d,J=7.3Hz,1 H),7.64(d,J=7.8Hz,2H),7.58(s,1H),4.43(qd,J=14.4,7.3Hz,2H),1.47(t,J=7.3Hz,3H); ESIMS(m / z)541.05(MH) + .

[0512] Example 24: Synthesis of 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine (Compound 223)

[0513] Step-1: Synthesis of tert-butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)carbamate (Compound 222)

[0514] A solution of 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) in dioxane (25 mL) was degassed under a nitrogen atmosphere for 10-15 min. 4,5-bis(diphenylphosphino-9,9-dimethylxantphos) (239 mg, 0.41 mmol) was then added, followed by palladium(II) acetate (18.57 mg, 0.08 mmol) and stirred under nitrogen for a few more minutes. The reaction mixture was heated at 100 ° C for 12 h. After completion of the reaction, the reaction mixture was filtered through celite and then 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 the crude compound, which was purified on a silica gel 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, 58.5% yield) as a solid. 1 H-NMR (400MHz, DMSO-d6) δ10.29(s,1H),9.38(dd,J=7.3,0.7Hz,1H),8.94(d,J=2.4Hz,1H),8.72(d,J=2 .2Hz,1H),7.62(d,J=7.3Hz,1H),7.43(s,1H),3.93(q,J=7.4Hz,2H),1.52(s,9H),1.32-1.26(m,3H); ESI MS(m / z)472(MH)+.

[0515] Step-2: Synthesis of 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine (Compound 223)

[0516] To tert-butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)carbamate (620 mg, 1.31 mmol) in dioxane (5 ml) was added concentrated hydrochloric acid (300 mg, 2.63 mmol) at 0 ° C. and the reaction mixture was stirred at room temperature for 12 h. After completion of the reaction, the reaction mixture was diluted with water (10 mL) and extracted with dichloromethane (3x10 mL). The combined organic layers were washed with brine solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude compound, which was purified by a silica gel CombiFlash system using ethyl acetate and dichloromethane as eluents to obtain 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 H-NMR (400MHz, DMSO-d6) δ9.27(dd,J=7.3,1.0Hz,1H),8.25(d,J=2.4Hz,1H),7.63(d,J=2.7Hz,1H) ,7.59(d,J=7.3Hz,1H),7.32(s,1H),6.47(s,2H),3.95(q,J=7.4Hz,2H),1.27(t,J=7.5Hz,3H); ESI MS(m / z)371.85(MH)+.

[0517] Example 25: Synthesis of 5-(ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine (Compound 218)

[0518] Step-1: tert-Butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(methyl)carbamate (Compound 224)

[0519] To a stirred solution of 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) in N,N-dimethylformamide (15 ml) was added sodium hydride (30.5 mg, 1.27 mmol) slowly at 0°C under nitrogen. The reaction mixture was then stirred at 0°C for 15 minutes, followed by the addition of iodomethane (0.20 ml, 3.18 mmol). The reaction mixture was warmed to room temperature and stirred for 12 h. 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 solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude compound, which was purified on a silica gel 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)pyridinepyridine-3-methylcarbamate (350 mg, 0.72 mmol, 68.0 % yield) as a solid. 1 H-NMR (400MHz, DMSO-d6) δ9.40(dd,J=7.3,1.0Hz,1H),8.99(d,J=2.4Hz,1H),8.43(d,J=2.6Hz,1H),7.64 (d,J=7.3Hz,1H),7.44(s,1H),3.91(q,J=7.4Hz,2H),3.36(s,3H),1.45(s,9H),1.27(t,J=7.5Hz,3H); ESI MS(m / z)486(MH)+.

[0520] Step 2: 5-(Ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine (Compound 218)

[0521] 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, 43% yield) was prepared from tert-butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(methyl)carbamate (220 mg, 0.45 mmol) according to the reaction conditions described in step 2 of compound 223 (Example 24). 1H-NMR (400MHz, DMSO-d6) δ9.28(dd,J=7.3,1.0Hz,1H),8.27(d,J=2.7Hz,1H),7.60(d,J=7.3Hz,1H),7.51(d,J=2.7 Hz,1H),7.32(s,1H),7.07(q,J=5.1Hz,1H),3.97(q,J=7.4Hz,2H),2.85(d,J=4.9Hz,3H),1.29(t,J=7.5Hz,3H); ESI MS(m / z)386(MH)+.

[0522] Example 26: Synthesis of 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)acetonitrile (Compound 232)

[0523] 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) was added potassium fluoride (0.40 g, 6.89 mmol) and the reaction mixture was stirred under nitrogen purge for 10 min, followed by the addition of 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloromethane adduct (0.188 g, 0.23 mmol). The resulting reaction mixture was heated at 90 ° C for 3 h. 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), and the combined organic layers were washed with brine solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude compound, which was used directly in the next reaction. ESI MS (m / z) 423.85 (MH) + .

[0524] The crude product was dissolved in methanol (25 ml) and potassium fluoride (0.137 g, 2.36 mmol) in water (5 ml) was added. The resulting reaction mixture was stirred at 90 ° C for 16 h. The reaction mixture was cooled to room temperature and diluted with water (30 mL). The aqueous layer was extracted with ethyl acetate (3x20 ml), and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and condensed under reduced pressure to give the crude product. Ethyl acetate in hexane was used as the eluent and purified by a silica gel CombiFlash system to give 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)acetonitrile (420 mg, 1.06 mmol, 45.0% yield) as a solid.1 H-NMR (400MHz, DMSO-d6) δ9.45(dd,J=7.3,1.0Hz,1H),9.02(d,J=2.2Hz,1H),8.52(d,J=2.2Hz,1H) ,7.66(d,J=7.3Hz,1H),7.48(s,1H),4.38(s,2H),3.91(q,J=7.4Hz,2H),1.28(t,J=7.3Hz,3H); ESI MS(m / z)395.6(MH)+.

[0525] Example 27: Synthesis of 5-(6-ethyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 173)

[0526] 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, 0.61 mmol) in dioxane (6 mL) was thoroughly deoxygenated by three vacuum / nitrogen cycles, followed by the addition of tetrakis(triphenylphosphine)palladium(0) (59.1 mg, 0.05 mmol). 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 (2×5 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 silica gel column chromatography using 20% ​​ethyl acetate in hexane as eluent to obtain 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) in solid form. 1 H-NMR (400MHz, DMSO-d6) δ9.43 (dt, J=7.3, 0.9Hz, 1H), 8.43 (dd, J=8.3, 1.0Hz, 1H), 7.87 (dd, J=8.3, 1.0Hz, 1H), 7.62(dd,J=7.2,1.1Hz,1H),7.46(d,J=2.7Hz,1H),3.84(q,J=7.4Hz,2H),2.16(s,3H),1.25(t,J=7.5Hz,3H); ESI MS(m / z)395.00(MH) + .

[0527] Example 28: Synthesis of 5-(3-(ethylsulfonyl)-6-isopropoxypyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 240)

[0528] To a stirred solution of propan-2-ol (46.1 mg, 0.77 mmol) in THF (4 mL) 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 allowed to warm to room temperature and stirred for a further 6 hours. After completion of the reaction, the reaction mixture was diluted with saturated aqueous 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 the crude product, which was purified by silica gel column chromatography using 20% ​​ethyl acetate in hexane as the eluent to obtain 5-(3-(ethylsulfonyl)-6-isopropoxypyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (98 mg, 0.24 mmol, 30.8% yield). 1 H-NMR (400MHz, DMSO-d6) δ9.43(dd,J=7.3,0.7Hz,1H),8.28(d,J=9.0Hz,1H),7.65(d,J=7.3Hz,1H),7.45(s,1H), 7.13(d,J=8.8Hz,1H),5.40-5.33(m,1H),3.78(q,J=7.3Hz,2H),1.34(d,J=6.1Hz,6H),1.24(t,J=7.5Hz,3H); ESI MS(m / z)414.60(MH) + .

[0529] Example 29: Synthesis of 5-(3-(ethylsulfonyl)-6-isopropoxypyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 241)

[0530] To a stirred solution of 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) in anhydrous acetonitrile (4 mL) at room temperature was added 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 (2×30 mL). The combined ethyl acetate layers were washed with water (50 mL), brine solution (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated to obtain the crude product, which was purified by silica gel column chromatography using 40% ethyl acetate in hexane as eluent to afford 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). 1 H-NMR (400MHz, DMSO-d6) δ9.35(dd,J=7.3,0.7Hz,1H),7.87(d,J=9.0Hz,1H),7.74(d,J=7.3Hz,1H),7.50(d,J=7.3Hz,1H),7.3 7(s,1H),6.67(d,J=9.0Hz,1H),4.02(q,J=7.1Hz,1H),3.63(q,J=7.3Hz,2H),2.01(t,J=7.5Hz,3H),1.62(d,J=6.1Hz,6H); ESI MS(m / z)414(MH) + .

[0531] Example 30: Synthesis of 5-(6-ethyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Compound 209)

[0532] 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) following the reaction conditions described in Step 9 of compound 122 (Example 19). 1H-NMR (400MHz, DMSO-d6) δ9.42(dd,J=7.3,0.7Hz,1H),8.39(d,J=8.1Hz,1H),7.74(d,J=8.3Hz,1H),7.63(d,J=7.3 Hz,1H),7.44(s,1H),3.83(q,J=7.4Hz,2H),2.95(q,J=7.6Hz,2H),1.27(t,J=7.3Hz,3H),1.27(t,J=7.3Hz,3H); ESI MS(m / z)385.35(MH) + .

[0533] Example 31: Synthesis of 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinonitrile (Compound 138)

[0534] Step-1: Synthesis of 5-(ethylthio)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinonitrile

[0535] To a stirred solution of 5-(5-bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (Step-3; Example 1) (1.0 g, 2.48 mmol) in anhydrous N,N-dimethylformamide (20 mL) under a nitrogen atmosphere was added zinc cyanide (1.019 g, 8.68 mmol). To the above solution was added tris(dibenzylideneacetone)dipalladium(0) (0.114 g, 0.12 mmol), followed by 1,1'-bis(diphenylphosphino)ferrocene (0.137 g, 0.25 mmol). The resulting reaction mixture was heated at 150°C for 2 h. After completion of the reaction, the reaction mixture was filtered through celite and washed with ethyl acetate. The organic layer was washed with brine solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude product, which was purified on a silica gel CombiFlash system using 15% ethyl acetate in hexanes as eluent to afford 5-(ethylthio)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinonitrile (300 mg, 0.86 mmol, 34.6 % yield) as a solid. 1 H-NMR (400MHz, DMSO-d6) δ9.39-9.37(m,1H),8.94(d,J=1.7Hz,1H),8.48(d,J=1.7Hz,1 H),7.93(d,J=7.3Hz,1H),7.45(s,1H),3.09(q,J=7.3Hz,2H),1.24(t,J=7.3Hz,3H); ESI MS(m / z)350.0(MH) + .

[0536] Step-2: Synthesis of 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinonitrile (Compound 138)

[0537] The title compound 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinonitrile (72 mg, 0.19 mmol, 13.19% yield) was prepared from 5-(ethylsulfanyl)-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 H-NMR (400MHz, DMSO-d6) δ9.50-9.48(m,2H),8.99(d,J=1.8Hz,1H),7.69(d,J=7.3Hz,1H),7.54(s,1H),3.92(q,J=7.4Hz,2H),1.30(t,J=7.5Hz,3H); ESI MS(m / z)381.95(MH) + .

[0538] Example 32: Synthesis of ((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-sulfoxide (Compound 172)

[0539] 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), dimethylsulfenyl imide (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. Tris(dibenzylideneacetone)dipalladium(0) (46.9 mg, 0.05 mmol) was added to the above solution, 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 (2×20 mL). The combined ethyl acetate layers were dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product, which was purified by silica gel column chromatography using 90% ethyl acetate in hexane as the eluent to give ((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-sulfoxide (112 mg, 0.25 mmol, 48.9% yield). 1H-NMR (400MHz, DMSO-d6) δ9.41(dd,J=7.3,1.0Hz,1H),8.09(d,J=8.8Hz,1H),7.57(d,J=7.3Hz,1H),7.4 2(s,1H),6.93(d,J=8.8Hz,1H),3.74(q,J=7.4Hz,2H),3.43(d,J=20.1Hz,6H),1.23(t,J=7.5Hz,3H); ESI MS(m / z)447.90(MH) + .

[0540] The following compounds in Table 1 were obtained using appropriate starting materials and following similar procedures as described in Examples 1 to 32.

[0541] Table-1

[0542]

[0543]

[0544]

[0545]

[0546]

[0547]

[0548]

[0549]

[0550]

[0551]

[0552]

[0553]

[0554]

[0555]

[0556]

[0557]

[0558]

[0559]

[0560]

[0561]

[0562]

[0563]

[0564]

[0565]

[0566]

[0567]

[0568]

[0569]

[0570]

[0571]

[0572]

[0573]

[0574]

[0575]

[0576] *Compound names generated using Chemdraw Professional 19.1

[0577] As described herein, compounds of formula (I) exhibit insecticidal activity against a wide variety of insects that attack important agricultural crops.The activity of the compounds of the invention was evaluated as described in the following tests.

[0578] Biological Examples:

[0579] Example A: Cotton bollworm (Helicoverpa armigera)

[0580] A diet incorporation method was used, in which the required amount of test compound was weighed and dissolved in a test tube containing a solvent solution. The test tube was placed on a vortex at 2000 rpm for 90 minutes for proper mixing. When the temperature in the bioassay container reached approximately 50°C, the semi-synthetic diet was incorporated into the solution. The compound and diet were thoroughly stirred for proper mixing and then cooled for 30 minutes. The solidified diet was cut into equal pieces, and each piece was transferred to a cell of a bioassay tray. A single starved third-instar larva was released into each of the cells of the bioassay tray, and the tray was covered with a lid. The bioassay tray was maintained under laboratory conditions at a temperature of 25°C and a relative humidity of 70%. Observations of dead, moribund, and living larvae were recorded 96 hours after larval release. The percentage mortality was calculated by combining dead and moribund larvae and comparing the results with an untreated control. Compounds 4 7 8 29 34 38 39 4166 70 75 76 94 96 98 100 111 126 127 136 155 156 160 166 192 203 229 231 and 235 were recorded to cause ≥70% mortality at 300 PPM.

[0581] Example B: Spodoptera litura

[0582] A diet incorporation method was used, in which the required amount of test compound was weighed and dissolved in a test tube containing a solvent solution. The test tube was placed on a vortex at 2000 rpm for 90 minutes for proper mixing. When the temperature in the bioassay container reached approximately 50°C, the semi-synthetic diet was incorporated into the solution. The compound and diet were thoroughly stirred for proper mixing and then cooled for 30 minutes. The solidified diet was cut into equal pieces, and each piece was transferred to a cell of a bioassay tray. A single starved third-instar larva was released into each of the cells of the bioassay tray, and the tray was covered with a lid. The bioassay tray was maintained under laboratory conditions at a temperature of 25°C and a relative humidity of 70%. Observations of dead, moribund, and living larvae were recorded 96 hours after larval release. The percentage mortality was calculated by combining dead and moribund larvae and comparing the results with an untreated control. Compounds 4 17 29 37 38 39 6676 87 94 96 98 100 101 111 125 126 127 136 155 156 168 192 193 203 205 208 231 234 and 235 were recorded to cause ≥70% mortality at 300 PPM.

[0583] Example C: Diamondback moth (Plutella xylostella)

[0584] The test was performed using the leaf dip method, where the desired amount of compound was weighed and dissolved in a test tube containing the solvent solution. Proper mixing was achieved by vortexing at 2000 rpm for 90 minutes and then diluting with 0.01% Triton-X solution to obtain the desired test concentration. Cabbage leaves were dipped into the compound solution for 10 seconds, shade-dried for 20 minutes, and then transferred to cells in bioassay trays. A single second-instar larva was released into each cell and the trays were covered with lids. The bioassay trays were then maintained under laboratory conditions at 25°C and 70% relative humidity. Observations for dead, moribund, and living larvae were recorded for 72 hours after release. Percent mortality was calculated by combining dead and moribund larvae and comparing the results with an untreated control. Compound 3 4 6 7 8 10 15 16 17 18 20 23 27 28 29 31 32 34 37 38 39 40 41 47 54 66 67 69 70 71 75 78 79 80 86 87 88 89 94 95 96 97 98 100 101 102 103 104 105 111 116 117 118 119 121 122 123 124 125 126 127 128 129 131 132 135 136 140 141 142 144 146 148 149 155 156 160 161 162 164 166 167 168 170 171 173 174 176 177 178 180 181 182 183 184 185 186 187 189 190 191 192 193 199 201 202 203 205 208 209 210 211 212 213 216 217 218 220 222 223 224 226 227 229 230 231 232 233 234 235 236 238 239 240 241 242 243 244 and 245 recorded mortality rates ≥70% at 300 PPM.

[0585] Example D: Bemisia tabaci

[0586] The test was conducted using the leaf dip method, where the desired amount of compound was weighed and dissolved in a test tube containing the solvent solution. The solution was maintained on a vortex at 2000 rpm for 90 minutes for proper mixing, and then diluted to the desired test concentration with a 0.01% Triton-X solution. Eggplant (Brinjal) leaves were dipped in the compound solution for 10 seconds, allowed to dry in the shade for 20 minutes, and then placed with the leaves facing up in 4 ml of 1% agar solution in individual perforated container lids. A known number of newly emerged whitefly adults were collected using a modified aspirator and released into a perforated container containing the lid of the treated leaf. The containers were maintained in a plant growth chamber at 25°C and 70% relative humidity. Observations for dead, moribund, and living adults were recorded 72 hours after release. Percent mortality was calculated by combining dead and moribund adults and comparing the results to an untreated control. Compounds 55, 87, and 198 resulted in ≥70% mortality at 300 PPM.

[0587] Example E: Green peach aphid (Myzus persicae)

[0588] The test was conducted using the leaf dip method, in which the desired amount of compound was weighed and dissolved in a test tube containing the solvent solution. The solution was then mixed by vortexing at 2000 rpm for 90 minutes and then diluted to the desired test concentration with 0.01% Triton-X solution. Pepper leaves were dipped in the compound solution for 10 seconds, shade-dried for 20 minutes, and then placed with the leaf facing up in a cell of a bioassay tray containing 4 ml of 1% agar solution. A known number of third-instar nymphs collected in a Petri dish were released into the cell along with the treated leaves, and the cell was covered with a perforated lid for improved aeration. The tray was placed in a plant growth chamber at 25°C and 70% relative humidity. Observations for dead, moribund, and living nymphs were recorded 72 hours after release. Percent mortality was calculated by combining dead and moribund nymphs and comparing the results with an untreated control. Compounds 11, 87, 106, 107, 108, 109, 141, 160, 167, 182, 198, 220, 234, and 244 were recorded to cause mortality > 70% at 300 PPM.

[0589] Example F: Brown Planthopper (Nilaparvata lugens)

[0590] The test was conducted using the seedling dip method, in which the desired amount of compound was weighed and dissolved in a test tube containing the solvent solution. The test tube was placed on a vortex at 2000 rpm for 90 minutes for proper mixing, and then diluted to the desired test concentration with 0.01% Triton-X solution. Rice seedlings were dipped in the compound solution for 10 seconds, shade-dried for 20 minutes, and then placed in glass test tubes with the roots kept in water. Fifteen third-instar nymphs were released into each test tube, which was then placed in a plant growth chamber maintained at 25°C and 75% relative humidity. Observations for dead, moribund, and living nymphs were recorded for 72 hours after release. Percent mortality was calculated by combining dead and moribund nymphs and comparing the results to an untreated control. Compounds 41, 87, 115, 116, 130, 141, 149, 166, 167, 168, 174, 182, and 198 resulted in ≥70% mortality at 300 ppm.

[0591] The invention has been described with reference to certain preferred embodiments and other embodiments will become apparent to those skilled in the art from consideration of the specification. It will be apparent to those skilled in the art that many modifications can be made to the materials and methods without departing from the scope of the invention.

Claims

1. A compound of formula (I), or an agriculturally acceptable salt thereof: in, R 1 Selected from C1-C2-alkyl; Y represents O or NR Y ; R Y is selected from hydrogen, cyano and C1-C4-alkyl; R 2 is selected from 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 、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, phenyl, benzyl and C3-C 10 -heterocyclic group; wherein R 2 Each group is optionally replaced by one or more R 2a group substitution; R 2a is selected from halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, OR 4 NR 5 R 6 、C(=O)R 8 、S(O) 0-2 R 7 , phenyl, benzyl and C3-C 10 -heterocyclic group; where R 2a Each group is optionally replaced by one or more R 2aa group substitution; R 2aa is selected from 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 and S(O) 0-2 R 7 ; Q is a group selected from the group consisting of formula Q1, Q2 and Q5, which is replaced by one or more R 3 and R 3’ replace; The premise is that Q is attached to the C2 or C5 carbon of the pyridine ring; R 3 is a C1-C2-haloalkyl group; R 3 ' is hydrogen; R 4 is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, phenyl, benzyl and C3-C 10 -heterocyclic group; wherein R 4 Each group of R 4a replace; R 4a is selected from halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl and C(=O)R′; R 5 is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C8-cycloalkyl, OR 4 、S(O) 0-2 R 7 、C(=O)R 8 、C6-C 10 -aryl, C7-C 14 -aralkyl and C3-C 10 -heterocyclic group; wherein R 5 Each group of R 5a replace; R 5a is OR′; R 6 is selected from hydrogen and C1-C6-alkyl; R 7 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl and C3-C8-cycloalkyl; R 8 is selected from 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 , phenyl, benzyl and C3-C 10 -heterocyclic group; R 9 is selected from C1-C6-alkyl, C1-C6-haloalkyl and C3-C8-cycloalkyl; R 10 is selected from hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl and C3-C8-cycloalkyl; Two R's 9 Substituent or R 9 and R 10 The substituents together with the atoms to which they are attached or together with other atoms selected from C, N, O, S, and optionally including 1 to 3 atoms selected from C(=O), C(=S), S(O) 0-2 and the ring members of Si(R')2, may form a 4- to 7-membered ring, some of which are optionally substituted with one or more R' groups; R' is selected from hydrogen, C1-C6-alkyl, C3-C8-cycloalkyl and N(R")2; R" is selected from hydrogen and C1-C6-alkyl; "n" is an integer from 0 to 1; "m" is an integer from 0 to 3.

2. The compound of formula (I) according to claim 1, wherein Q is selected from the formula Q 1a , Q 1b , Q 2a , Q 2b and Q5; in, R 3 and R 3' Same as defined in claim 1.

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

4. The compound of formula (I) according to claim 1, wherein The compound of formula (I) is represented by the compound of formula (Ib); in, R 1 、R 2 , Q, Y, n and m are the same as defined in claim 1.

5. The compound of formula (I) according to claim 1, wherein Q is the formula Q 1a or Q 1b ; in, R 3 and R 3' Same as defined in claim 1.

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

7. The compound of formula (I) according to claim 1, wherein The compound of formula (I) is selected from 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(6-(3,5-dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 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; 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; 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; 5-(ethylsulfonyl)-N-(4-(trifluoromethoxy)phenyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; 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; 7-(5-bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 7-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 7-(5-(3,5-dichlorophenyl)-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 7-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-phenylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(4-fluorophenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 4-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)benzonitrile; 5-(3-(ethylsulfonyl)-6-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(6-(4-chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(3-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 3-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)benzonitrile; 5-(5-bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 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; 5-(6-(3-chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 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; 5-(3-(ethylsulfonyl)-6-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 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; 5-(5-(ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylthio)-5-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 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; 5-(3-(ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(6-chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(ethylsulfonyl)-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(3-(ethylthio)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(4-fluoro-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(6-(4-bromo-1H-imidazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(6-(4-chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 6-(6-(3,5-dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 4-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)pyridin-2-yl)benzonitrile; 6-(3-(ethylsulfonyl)-6-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(3-methyl-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(6-(3-bromo-1H-1,2,4-triazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(6-(4-chloro-1H-pyrazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(1-methyl-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(6-chloro-5-(ethylthio)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(ethylsulfonyl)-6-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylthio)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(6-chloro-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(3-(ethylsulfonyl)-6-(1H-1,2,3-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylthio)-5-(1-methyl-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(5-(ethylsulfonyl)-6-(4-(trifluoromethoxy)phenyl)pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(3-methyl-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(4-fluoro-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(1-methyl-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(ethylsulfonyl)-6-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 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; 5-(5-(3,5-dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(3,5-dichlorophenyl)-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 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; 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; 6-(6-chloro-5-(ethylthio)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; (5-bromo-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(ethyl)(imino)-16-sulfoxide; 5-(5-(ethylsulfonyl)-6-(3-methyl-1H-pyrazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(ethylsulfonyl)-6-(1H-1,2,4-triazol-1-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; ((5-(ethylthio)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)dimethyl-16-sulfoxide; ((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)dimethyl-16-sulfoxide; 5-(5-(4-bromo-1H-pyrazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(4-chloro-1H-pyrazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 6-(5-bromo-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(6-chloro-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(4-fluorophenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(pyrimidin-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; Ethyl(imino)(5-(4-(trifluoromethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-16-sulfoxide; 5-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(5-(4-chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(5-(3,5-dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(5-(3,5-difluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(4-fluorophenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; ((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)dimethyl-16-sulfoxide; Diethyl((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)-16-sulfoxide; Ethyl((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)(methyl)-16-sulfoxide; 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-ol; 6-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(3-chloro-5-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 2-(5-bromo-3-(ethylthio)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 6-(3-(ethylsulfonyl)-5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; Diethyl((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)-16-sulfoxide; Ethyl((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)(methyl)-16-sulfoxide; 2-(3-(ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(3-(ethylsulfonyl)-5-(4-fluorophenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(3-(ethylsulfonyl)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(3-(ethylsulfonyl)-5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(5-(3,5-difluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(5-(4-chlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(5-(4-chloro-3-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 5-(5-(3,5-difluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(4-chloro-3-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(3-chloro-4-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 2-(5-(3,5-dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(3-(ethylsulfonyl)-5-(3-methyl-1H-1,2,4-triazol-1-yl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(5-(3-chloro-5-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)thiazole; 5-(3-(ethylsulfonyl)-5-(1-methyl-1H-pyrazol-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 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; 5-(3-(ethylsulfonyl)-5-(pyrimidin-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(5-cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 6-(6-(3-chloro-5-fluorophenyl)-5-(ethylsulfonyl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinonitrile; Diethyl((5-(ethylsulfonyl)-6-(9-methyl-8-(trifluoromethyl)-9H-purin-2-yl)pyridin-3-yl)imino)-16-sulfoxide; 5-(3-(ethylsulfonyl)-6-(3-fluoro-1H-pyrazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; N-cyclopropyl-5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; 5-(5-cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(2-methoxypyrimidin-5-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(3-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 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; 5-(3-(ethylsulfonyl)-5-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 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; 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; ((5-(ethylsulfonyl)-6-(9-methyl-8-(trifluoromethyl)-9H-purin-2-yl)pyridin-3-yl)imino)dimethyl-16-sulfoxide; 5-(ethylsulfonyl)-6-(9-methyl-8-(trifluoromethyl)-9H-purin-2-yl)pyridin-3-ol; 5-(3-(ethylsulfonyl)-5-methylpyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 6-(5-(ethylsulfonyl)-6-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridin-3-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(3,4-dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 2-(3-(ethylsulfonyl)-5-(1H-1,2,4-triazol-1-yl)pyridin-2-yl)-9-methyl-8-(trifluoromethyl)-9H-purine; 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; 5-(6-chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(cyclopropylmethoxy)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(5-(4-chloro-3-fluorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(5-(3,4-dichlorophenyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-methylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(6-chloro-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(Ethylsulfonyl)-N,N-dimethyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; 5-(ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; N-cyclopropyl-5-(ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; 5-(6-chloro-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; N-cyclopropyl-5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine; 5-(6-cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; ((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-sulfoxide; 5-(3-(ethylsulfonyl)-6-(prop-1-yn-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; N-cyclopropyl-5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; N-cyclopropyl-5-(ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; 5-(5-(3-bromo-1H-1,2,4-triazol-1-yl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-(prop-1-yn-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; ((5-(ethylthio)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-sulfoxide; 5-(6-cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(3-(ethylthio)-6-methylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-methylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-methylpyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; ((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-sulfoxide; ((5-(ethylthio)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)dimethyl-16-sulfoxide; Ethyl((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)(methyl)-16-sulfoxide; 5-(3-(ethylthio)-6-methylpyridin-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 5-(6-cyclopropyl-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-cyclopropyl-3-(ethylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylthio)-5-(4-fluorophenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylthio)-5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; Ethyl(5-(4-fluorophenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(imino)-16-sulfoxide; Ethyl(imino)(5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-16-sulfoxide; (6-chloro-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(ethyl)(imino)-16-sulfoxide; 5-(3-(ethylsulfonyl)-6-(methylthio)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(methylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylthio)-5-vinylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; (5-((dimethyl)oxo)-16-imino)amino)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(ethyl)(imino)-16-sulfoxide; N-(ethyl)oxo)(5-(4-(trifluoromethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-16-thiocyanamide; (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)(imino)(methyl)-16-sulfoxide; 5-(3-(ethylsulfonyl)-5-(2-methylprop-1-en-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; Ethyl(imino)(5-(2-methylprop-1-en-1-yl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-16-sulfoxide; Ethyl(imino)(5-(3-(trifluoromethyl)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-16-sulfoxide; 5-(3-(ethylsulfonyl)-5-(prop-1-en-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(2-cyclopropylvinyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; N-((5-((dimethyl)oxo)-16-imino)amino)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(ethyl)(oxo)-16-imino)cyanamide; N-(ethyl)oxo)(5-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-16-thiocyanamide; N-(ethyl)5-(4-fluorophenyl)-2-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(oxo)-16-thiocyanamide; 5-(6-ethyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(2-methylprop-1-en-1-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-ethyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-5-vinylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-cyclobutyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; tert-Butyl 2-cyano-2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetate; 5-(3-(ethylsulfonyl)-6-(prop-1-en-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; (E)-5-(6-(2-cyclopropylvinyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetonitrile; 5-(ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine; 2-(5-(ethylthio)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)acetonitrile; 2-((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)oxy)-2-methylpropanamide; 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-ol; tert-Butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)carbamate; 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine; tert-Butyl (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(methyl)carbamate; N-(tert-Butyl)-2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)acetamide; 5-(3-(ethylsulfonyl)-6-methoxypyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(6-ethoxy-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(6-cyclobutyl-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(difluoromethoxy)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(Ethylsulfonyl)-N,N-dimethyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-amine; 5-(3-(ethylsulfonyl)-5-(pyrimidin-2-yl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)acetonitrile; N-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)cyclopropanecarboxamide; 1-((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)hexahydro-1,6-thiopyran 1-oxide; 1-((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)imino)-116-thietane 1-oxide; 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-ol; 5-(3-(ethylsulfonyl)-6-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-isopropylpyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-(2,2,2-trifluoroethoxy)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(3-(ethylsulfonyl)-6-isopropoxypyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(ethylsulfonyl)-N-isopropyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; N-(cyclopropylmethyl)-5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; 5-(3-(ethylsulfonyl)-6-(thietan-3-yloxy)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(ethylsulfonyl)-N-propyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-amine; 1-((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)imino)-116-thietane 1-oxide; N-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)cyclopropanecarboxamide; 1-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)cyclopropane-1-carbonitrile; N-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-N-methylacetamide; 1-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)urea; 1-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-1,3-dimethylurea; 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-2-methylpropionitrile; 5-(3-(ethylsulfonyl)-5-(trifluoromethyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)picolinamide; 5-(Ethylsulfonyl)-N-methyl-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)picolinamide; 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinate; 5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)nicotinateazetidin-1-yl; (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)methanone; (5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)(morpholinyl)methanone; N-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)cyclopropanesulfonamide; N-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-N-methylcyclopropanesulfonamide; N-((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)(methyl)(oxo)-16-sulfanylide)cyanamide; Ethyl(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)((trifluoromethyl)imino)-16-sulfoxide; 2-((5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)oxy)-2-methylpropionitrile; 5-(3-(ethylsulfonyl)-5-(pyridin-2-yloxy)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 5-(5-(2,2-difluorocyclopropyl)-3-(ethylsulfonyl)pyridin-2-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; tert-Butyl 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)hydrazine-1-carboxylate; 1-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)ethan-1-one; N-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-2-yl)-O-methylhydroxylamine and 2-(5-(ethylsulfonyl)-6-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyridin-3-yl)-1,1,1-trifluoropropan-2-ol.

8. A composition comprising a compound of formula (I) according to claim 1 or an agriculturally acceptable salt thereof, and at least one additional component selected from the group consisting of an adjuvant.

9. The composition according to claim 8, wherein The composition additionally comprises at least one biologically active compatible compound selected from the group consisting of a fungicide, an insecticide, an herbicide, a plant growth regulator, a fertilizer or a nutrient.

10. The composition according to claim 8, wherein The compound of formula (I) accounts for 0.1% to 99% by weight of the total weight of the composition.

11. The composition according to claim 8, wherein The compound of formula (I) accounts for 5% to 50% by weight of the total weight of the composition.

12. A method for controlling insect and acarid pests, comprising contacting the insect and acarid pests, their habitats, breeding grounds, food supplies, plants, seeds, soil or environments in which the insect and acarid pests grow or may grow, or materials, plants, seeds, soil, surfaces or spaces to be protected from attack or infestation by pests with a biologically effective amount of a compound of formula (I) according to claim 1 or an agriculturally acceptable salt thereof, or a composition according to claim 8, with the proviso that the method does not include methods of treating the human or animal body by surgery or therapy.

13. A method for protecting crops from attack or infestation by insect and acarid pests, comprising contacting the crops with a compound of formula (I) according to claim 1 or an agriculturally acceptable salt thereof or a composition according to claim 8.

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

15. A method for protecting seeds, plants and plant parts from soil insects and protecting seedling roots and shoots from soil and foliar insects, comprising contacting the seeds before sowing and / or after pre-germination with a compound of formula (I) according to claim 1 or an agriculturally acceptable salt thereof or a composition according to claim 8.

16. Use of the compound of formula (I) or an agriculturally acceptable salt thereof according to claim 1 or the composition according to claim 8 for controlling insect and acarid pests in agricultural and horticultural crops.

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