TW202304919A - Fused heterocyclic compounds and their use as pest control agents - Google Patents

Abstract

The present invention discloses a fused heterocyclic compound of formula (I), wherein, Q, R ¹, Z, A, G ¹, G ², E, Y and m are as defined in the detailed description. The present invention further discloses methods for their preparation and use of the compounds of formula (I) as a pest control agent.

Description

Fused heterocyclic compounds and their use as pest control agents

This invention relates to fused heterocyclic compounds. More specifically, the present invention relates to fused heterocyclic compounds of formula (I) and methods for their preparation. The present invention also relates to the use of the fused heterocyclic compound of formula (I) as a pest control agent.

Modern insecticides and acaricides currently available have to fulfill many requirements, eg with regard to degree of activity, long-lasting efficacy, beneficial side effects and their possible uses. Efforts have been made over the past few decades to develop selective insecticides that specifically act on a biochemical mode of action in insects or mites, but otherwise in a manner different from The known insecticides exhibit their properties in an advantageous manner.

Heterocyclic compounds having insecticidal activity are known and described in prior art such as PCT Patent Publication No. WO2020250183, PCT Patent Publication No. WO2018221720 and PCT Patent Publication No. WO201765228.

There is a constant need for novel compounds that are more effective, less toxic, safer for the environment, and/or have a different mode of action.

In view of the above facts, the present invention contemplates such compounds which meet or overcome the disadvantages associated with the prior art.

It has now been surprisingly found that certain novel insecticidally active fused heterocyclic compounds having sulfur-containing substituents which are the subject of the present invention have more advantageous properties as expected as insecticides.

式(I) 其中，Q、Z、Y、m、R ¹、A、G ¹、G ²、D及E係如以下說明所詳細定義。 Accordingly, the present invention provides fused heterocyclic compounds of formula (I) or agriculturally acceptable salts, isomers/structural isomers, stereoisomers, diastereomers, mirror isomers, mutual Allomers, metal complexes, isomorphs or N-oxides.

Formula (I) wherein, Q, Z, Y, m, R ¹ , A, G ¹ , G ² , D and E are defined in detail in the following description.

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

In another embodiment, the present invention provides a composition for controlling or preventing invertebrate pests, the composition comprising an effective amount of the compound of formula (I), its agriculturally acceptable salt, isomeric Compounds/structural isomers, stereoisomers, diastereoisomers, enantiomers, tautomers, metal complexes, isomers or N-oxides, and at least one selected from surfactants and other components of the group consisting of additives.

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

In another embodiment, the present invention provides compounds of formula (I) and agriculturally acceptable salts, isomers/structural isomers, stereoisomers, diastereomers, mirror isomers, Use of tautomers, metal complexes, allomers or N-oxides, compositions or combinations thereof for controlling invertebrate pests or animal parasites in agricultural and/or horticultural crops.

In yet another embodiment, the present invention provides a method of controlling an invertebrate pest comprising causing the invertebrate pest, its habitat, breeding ground, food supply, plant, seed, soil, area, material or insect and acarid to The environment in which pests are growing or may grow, or the material, plant, seed, soil, surface or space to be protected from pest attack or infestation and the compound of formula (I) or its salt, isomer/structural isomer, An effective dose of a stereoisomer, metal complex, isomer, or N-oxide composition or combination thereof is contacted.

Definitions provided herein for terms used herein are for illustrative purposes only and do not in any way limit the scope of the invention disclosed herein.

As used herein, the terms "comprises, comprising", "includes, including", "has, having", "contains, containing", "characterized by" or any other variation thereof, to cover the non-exclusive inclusion, subject to any limitations expressly stated. For example, a composition, mixture, process, or method consisting of a list of elements is not necessarily limited to those elements, but may include elements not expressly listed or other elements inherent in such composition, mixture, process, or method.

The conjunction "consisting of" (consisting of) excludes any unspecified element, step or ingredient. If present in a claim item, it will render the claim item incapable of containing material other than that stated, except as impurities with which it is normally associated. When the phrase "consisting of" appears in a sentence in the body of a claim rather than immediately following the preamble, it restricts only the elements specified in that sentence; other Components are not excluded from the overall request item.

The conjunction phrase "consisting essentially of" (consisting essentially of) is used to define a composition or method comprising materials, steps, features, ingredients or elements, except for those disclosed in the context, these additional The materials, steps, features, components or elements do not materially affect the basic and novel characteristics of the claimed invention. The phrase "consisting essentially of" occupies the middle position between "including" and "consisting of".

Further, unless expressly stated to the contrary, "or" means an inclusive "or" rather than an exclusive "or". For example, a condition A "or" B is satisfied by any of the following: A is true (or exists), B is false (or does not exist), A is false (or does not exist), B is true (or exists ), and both A and B are true (or exist).

Likewise, the indefinite article "a" (a and an) preceding an element or component of the invention is intended not to limit the instance (ie, the number of occurrences) of that element or component. Thus, "a" (a or an) should be read to include one or at least one, and word forms of elements or components in the singular include the plural unless it is obvious that the number is meant in the singular.

The term "invertebrate pest" as used herein includes pests such as arthropods, gastropods and nematodes of economic importance. The term "arthropod" includes insects, mites, spiders, scorpions, centipedes, millipedes, bulb bugs and myriapods. The term "gastropod" includes snails, slugs and other stalks. The term "nematode" refers to living organisms of the Phylum Nematoda. The term "worm" includes roundworms, heartworms, herbivorous nematodes (Nematoda), trematodes (Tematoda), acanthocephala, and tapeworms (Cestoda).

The term "agronomy" refers to the production of field crops, such as for food, feed and fiber, and includes corn, soybeans and other legumes, rice, grains (such as wheat, oats, barley, rye, rice, maize), leaf Vegetables (such as lettuce, kale, and other rapeseed crops), fruit vegetables (such as tomato, pepper, eggplant, cruciferous plants, and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (such as pome fruit, stone fruits and citrus), small fruits (berries, cherries) and other specialty crops (e.g. canola, sunflower, olives).

The term "nonagronomic" refers to crops other than agricultural crops, such as horticultural crops (e.g., greenhouses, nurseries, or ornamentals that are not grown in fields), residential, agricultural, commercial and industrial structures, turf (e.g., sod farms, pastures, Golf courses, lawns, sports fields), wood products, stored products, agroforestry and vegetation management, public health (i.e. humans) and animal health (e.g. domesticated animals (e.g. pets, livestock and poultry) and non-domesticated animals (e.g. wild animals ))Applications.

Non-agronomic applications include the protection of animals against invertebrate parasitism by administering to the animal to be protected a parasiticidally effective (i.e. biologically effective) amount of a compound of the invention, usually in the form of a composition formulated for veterinary use. Infestation by pests. As referred to in the specification and claims of this case, the terms "parasiticidal" and "parasiticidal" refer to the observable effect on invertebrate parasitic pests of protecting animals from infestation by the pests. A parasiticidal effect generally involves reducing the occurrence or activity of a target invertebrate parasitic pest. Such effects on pests include necrosis, death, stunted growth, reduced mobility or ability to remain in or on the body of the host animal, reduced feeding and inhibited reproduction. These effects on invertebrate parasitic pests provide control (including prevention, reduction or elimination) of parasitic infestation or infection in animals.

The compounds of the invention may exist in pure form or as different possible isomers, for example stereoisomers or structural isomers. Various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformational isomers, tautomers, optical isomers, isomers, and geometric isomers. Any desired mixtures of these isomers are within the scope of the claims herein. Those of ordinary skill in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other isomer or when it is isolated from the other isomer . Furthermore, processes or methods or techniques for separating, concentrating and/or selectively preparing said isomers are known to those having ordinary skill in the art.

Definitions of various terms used herein will now be explained.

As used herein, the term "aliphatic compound" or "aliphatic group" refers to an organic compound whose carbon atoms are connected in a straight chain, branched chain or non-aromatic ring.

The term "alkyl", whether used alone or in compound form (such as "alkylthio" or "haloalkyl" or -N(alkyl) or alkylcarbonylalkyl or alkylsulfonamido, Including straight chain or branched C ₁ to C ₂₄ alkyl, preferably C ₁ to C ₁₅ alkyl, more preferably C ₁ to C ₁₀ alkyl, most preferably C ₁ to C ₆ alkyl. Non-limiting examples include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl base, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl 1,2-dimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl or different Isomers. If the alkyl group is at the end of the composite substituent, such as in an alkylcycloalkyl group, the initial part of the composite substituent, such as a cycloalkyl group, may be identically or differently and independently monosubstituted by an alkyl group or multiple substitutions. The same applies to composite substituents in which other groups such as alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy, etc. are terminally located.

The term "alkenyl", whether used alone or as a compound, includes straight or branched C ₂ -C ₂₄ olefins, preferably C ₂ -C ₁₅ olefins, more preferably C ₂ -C ₁₀ olefins , most preferably C ₂ -C ₆ olefins. Non-limiting examples of alkenes include vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 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 Alkenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl Alkenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl Base-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethane Base-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl Base-1-pentenyl, 2-methyl-1-pentenyl, 1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl Base-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 as part of a composite substituent, eg haloalkenyl and the like.

Non-limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl Base, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2- Methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl , 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl Base-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl base, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butyne base, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2 -butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl and the different isomers. This definition also applies to alkenyl as part of a composite substituent, eg haloalkynyl, etc., unless specifically defined elsewhere. The term "alkynyl" may also include moieties consisting of multiple triple bonds, eg 2,5-hexadiynyl.

The term "cycloalkyl" refers to an alkyl group that is closed to form a ring. Non-limiting examples include cyclopropyl, cyclopentyl, and cyclohexyl. This definition also applies to cycloalkyl as part of a composite substituent, eg cycloalkylalkyl etc., unless specifically defined elsewhere.

The term "cycloalkenyl" refers to an alkenyl group closed to form a ring including a monocyclic, partially unsaturated hydrocarbon group. Non-limiting examples include cyclopropenyl, cyclopentenyl, and cyclohexenyl. This definition also applies to cycloalkenyl as part of a composite substituent, eg cycloalkenylalkyl, etc., unless specifically defined elsewhere.

The term "cycloalkynyl" refers to an alkynyl group that is closed to form a ring, including monocyclic, partially unsaturated groups. Non-limiting examples include cyclopropynyl, cyclopentynyl, and cyclohexynyl. This definition also applies to cycloalkynyl as part of a composite substituent, eg cycloalkynylalkyl, etc., unless specifically defined elsewhere.

The terms "cycloalkoxy" and "cycloalkenyloxy" are similarly defined. Non-limiting examples of cycloalkoxy include cyclopropoxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as part of a composite substituent, eg cycloalkoxyalkyl, etc., unless specifically defined elsewhere.

The term "halogen", whether used alone or in compound form (eg "haloalkyl"), includes fluorine, chlorine, bromine or iodine. In addition, when used in compound words such as "haloalkyl", said alkyl group may be partially or completely substituted by halogen atoms, and the halogen atoms may be the same or different. Non-limiting examples of "haloalkyl" include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichloro Fluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-tri Fluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl , pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl and 1,1,1-trifluoropropan-2-yl. Unless specifically defined elsewhere, this definition also applies to haloalkyl as part of a composite substituent, eg haloalkylaminoalkyl and the like.

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

The term "haloalkoxy" refers to straight-chain or branched-chain alkoxy groups, wherein some or all of the hydrogen atoms in these groups may be replaced by the above-mentioned halogen atoms. Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chloro Fluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2 -Difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro -2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1-trifluoroprop-2-oxy. Unless specifically defined elsewhere, this definition also applies to haloalkoxy as part of a composite substituent, eg haloalkoxyalkyl and the like.

The term "haloalkylthio" refers to a straight-chain or branched alkylthio group in which some or all of the hydrogen atoms in these groups may be replaced by the above-mentioned halogen atoms. Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chloro Fluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2-di Fluoroethylthio, 2-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio , 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethylthio and 1, 1,1-trifluoropropan-2-thiol. Unless specifically defined elsewhere, this definition also applies to haloalkylthio as part of a composite substituent, eg haloalkylthioalkyl and the like.

Non-limiting examples of "haloalkylsulfinyl" include CF ₃ S(O), CCl ₃ S(O), CF ₃ CH ₂ S(O), and CF ₃ CF ₂ S(O). Non-limiting examples of "haloalkylsulfonyl" include CF ₃ S(O) ₂ , CCl ₃ S(O) ₂ , CF ₃ CH ₂ S(O) ₂ , and CF ₃ CF ₂ S(O) ₂ .

The term "hydroxy" refers to -OH, and amine 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, sulfonyl refers to S(O) ₂ , oxa refers to =O .

The term "alkoxy", whether used alone or as a compound, includes C ₁ to C ₂₄ alkoxy, preferably C ₁ to C ₁₅ alkoxy, more preferably C ₁ to C ₁₀ alkoxy Oxygen, preferably C ₁ to C ₆ alkoxy. Examples of alkoxy include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1- Dimethylethoxy, pentyloxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethyl Propoxy, Hexyloxy, 1,1-Dimethylpropoxy, 1,2-Dimethylpropoxy, 1-Methylpentyloxy, 2-Methylpentyloxy, 3-Methyl Pentyloxy, 4-methylpentyloxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-di Methylbutoxy, 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 and different isomers things. This definition also applies to alkoxy as part of a composite substituent, eg haloalkoxy, alkynylalkoxy, etc., unless specifically defined elsewhere.

The term "alkoxyalkyl" denotes an alkoxy substitution on an alkyl group. Non-limiting examples of "alkoxyalkyl" include CH ₃ OCH ₂ , CH _{3 OCH} 2 CH ₂ , CH ₃ CH ₂ OCH ₂ , CH ₃ CH ₂ CH ₂ CH ₂ OCH ₂ and CH ₃ CH ₂ OCH _{2 CH2} .

The term "alkoxyalkoxy" means an alkoxy substitution on an alkoxy group.

The term "alkylthio" includes functional groups of branched or straight-chain alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2 -Methylthio, 1,1-dimethylethylthio, pentylthio, 1-methylethylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio , 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio , 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1 ,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio and other different isomers.

Halocycloalkyl, Halocycloalkenyl, Alkylcycloalkyl, Cycloalkylalkyl, Cycloalkoxyalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Haloalkylcarbonyl , cycloalkylcarbonyl, haloalkoxyalkyl, etc. are defined similarly to the above examples.

The term "alkylthioalkyl" denotes an alkylthio substitution on an alkyl group. Non-limiting examples of "alkylthioalkyl" include -CH ₂ SCH ₂ , -CH ₂ SCH ₂ CH ₂ , CH ₃ CH ₂ SCH ₂ , CH ₃ CH ₂ CH ₂ CH ₂ SCH ₂ and CH ₃ CH ₂ SCH _{2CH2 .} "Alkylthioalkoxy" means an alkylthio substitution on an alkoxy group. The term "cycloalkylalkylamino" denotes cycloalkyl substitution on an alkylamine group.

Terms "alkoxyalkoxyalkyl", "alkylaminoalkyl", "dialkylaminoalkyl", "cycloalkylaminoalkyl", "cycloalkylaminocarbonyl", etc. , defined similarly to "alkylthioalkyl" or "cycloalkylalkylamino".

The term "alkoxycarbonyl" refers to an alkoxy group bonded to the main chain through a carbonyl group (-CO-). Unless specifically defined elsewhere, this definition also applies to alkoxycarbonyl as part of a composite substituent, eg cycloalkylalkoxycarbonyl and the like.

The term "alkoxycarbonylalkylamino" denotes an alkoxycarbonyl substitution on an alkylamine group. "Alkylcarbonylalkylamino" means an alkylcarbonyl substitution on an alkylamino group. The terms alkylthioalkoxycarbonyl, cycloalkylalkylaminoalkyl, etc. are defined similarly.

Non-limiting examples of "alkylsulfinyl" include methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, Acyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methyl Butylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl Sulfonyl, 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 Sulfonyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl, and 1-ethyl-2-methylpropylsulfinyl groups and different isomers. The term "arylsulfinyl" includes Ar-S(O), where Ar can be any carbocyclic or heterocyclic ring. Unless specifically defined elsewhere, this definition also applies to alkylsulfinyl groups as part of a composite substituent, eg haloalkylsulfinyl and the like.

Non-limiting examples of "alkylsulfonyl" include methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylsulfonyl, Propylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methyl Butylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1,1-dimethyl Propylsulfonyl, 1,2-dimethylpropylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2 ,2-Dimethylbutylsulfonyl, 2,3-Dimethylbutylsulfonyl, 3,3-Dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2- Ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl and different isomers. 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, eg haloalkylsulfonyl and the like.

The definitions of "alkylamino group", "dialkylamino group" and the like are similar to the above examples.

The term "carbocycle" (or carbocyclic or carbocyclyl) includes "aromatic carbocyclic systems" and "non-aromatic carbocyclic systems" or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds in which the rings can be Is aromatic or non-aromatic (where aromatic means that Huckel's rule is satisfied, and non-aromatic means that Huckel's rule is not satisfied).

Non-limiting examples of non-aromatic heterocyclic ring systems include cyclopropyl, cyclobutyl, cyclopentyl, norbornyl, and the like. Non-limiting examples of aromatic carbocyclic ring systems are phenyl, naphthyl, and the like.

The term "aryl" as used herein is a group containing any carbon-based aromatic group, including but not limited to phenyl, naphthalene, biphenyl, anthracene, and the like. Aryl groups can be substituted or unsubstituted. Furthermore, aryl groups can be monocyclic structures or comprise multiple ring structures which are either fused ring structures or connected through one or more bridging groups such as carbon-carbon bonds.

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

The term "hetero" in relation to rings refers to a ring having at least one ring atom other than carbon and which may contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, assuming each ring Contains not more than 4 nitrogens, not more than 2 oxygens and not more than 2 sulfurs.

The term "aromatic" means that Hückel's rule is satisfied, and the term "non-aromatic" means that Hückel's rule is not satisfied.

The term "heterocycle" (heterocyclic) or "heterocyclic ring system" includes "aromatic heterocycle" or "heteroaromatic ring system" as well as "non-aromatic heterocycle system" or polycyclic or bicyclic (spiro, Fused, bridged, non-fused) ring compounds, wherein the ring may be aromatic or non-aromatic, wherein the heterocyclic ring contains at least one heteroatom selected from N, O, S(O) _0-2 , and/or hetero Carbocyclic members of the ring may be substituted by C(=O), C(=S), C(=CR*R*) and C=NR*, where * represents an integer.

The term "non-aromatic heterocycle" (non-aromatic heterocycle or non-aromatic heterocyclic) refers to three to fifteen members containing 1 to 4 heteroatoms selected from O, N and S, preferably three to twelve membered saturated or partially unsaturated heterocycle: mono-, bi- or tricyclic heterocycle containing, in addition to carbon ring members, one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atom; if the ring contains more than one oxygen atom, they are not directly adjacent; non-limiting examples: oxetanyl, oxiranyl, aziridinyl, Tetrahydrofuryl, tetrahydrothiophenyl, pyrrolidinyl, isoxazolidinyl, isothiazolidinyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, 1,2,4-oxadiazole Alkyl, 1,2,4-Thiadiazolidinyl, 1,2,4-Triazolinyl, 1,2,4-Triazolidin-3-yl, 1,2,3-Triazolidinyl , 1,3,4-oxadiazolidinyl, 1,3,4-thiadiazolidinyl, 1,3,4-triazolidinyl, dihydrofuryl, dihydrothienyl, pyrrolinyl, Isoxazolyl, isothiazolyl, dihydropyrazolyl, dihydrooxazolyl, dihydrothiazolyl, piperidinyl, pyrazinyl, morpholinyl, thiomorpholinyl, 1,3-di Oxan-5-yl (1,3-dioxan-5-yl), tetrahydropyranyl, tetrahydrothiophenyl, hexahydropyridazinyl, hexahydropyrimidinyl, piperazinyl, and cycloserine. Unless specifically defined elsewhere, this definition also applies to heterocyclyl as part of a composite substituent, eg heterocyclylalkyl and the like.

The term "heteroaryl" or "aromatic heterocycle" means a five or six membered, fully unsaturated monocyclic ring system containing 1 to 4 heteroatoms selected from O, N and S; if the ring contains more than one oxygen atoms, they are not directly adjacent; five-membered heteroaryl containing 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur or oxygen atom; five-membered heteroaryl, in addition to carbon atoms, It may contain 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur or oxygen atom as ring members. Non-limiting examples: furyl, thienyl, pyrrolyl, pyrazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1, 2,4-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl , l,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 Heteroaryl: A five-membered heteroaryl group that, in addition to carbon atoms, may also contain 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms as ring members, of which two adjacent carbon ring members or one nitrogen and one phase Adjacent carbon ring members may be bridged by groups of but-1,3-diene-1,4-diyl, in which 1 or 2 carbon atoms may be replaced by nitrogen atoms, where these rings pass through one of the nitrogen ring members - attached to the main chain, non-limiting examples: 1-pyrrolyl, 1-pyrazolyl, 1,2,4-triazol-1-yl, 1-imidazolyl, 1,2,3-triazole- 1-yl and 1,3,4-triazol-1-yl.

Six-membered heteroaryl containing 1 to 4 nitrogen atoms: six-membered heteroaryl containing, in addition to carbon atoms, 1 to 3 and 1 to 4 nitrogen atoms respectively as ring members, non-limiting example: pyridine Base, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazine- 3-yl; benzo-fused five-membered heteroaryl containing 1 to 3 nitrogen atoms or 1 nitrogen and 1 oxygen or sulfur atom: non-limiting examples are indolyl, benzimidazolyl, indazole benzofuryl, benzothienyl, benzothiazolyl, benzoxazolyl; benzofused six-membered heteroaryl containing 1 to 3 nitrogen atoms, non-limiting examples: quinolinyl, Isoquinolyl, quinoxalinyl, phthalazinyl, quinazolinyl and cinnamyl.

Five to six membered bicyclic heteroaryl systems (bicyclic 5-6 heteroaryl systems) with a bridgehead (ring junction) nitrogen atom and containing 1 to 3 nitrogen atoms or 1 nitrogen atom and 1 oxygen or sulfur atom: Non-limiting examples include imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine, [1,2,4]triazolo[1,5-a]pyrimidine, [1,2 ,4]triazolo[1,5-b]pyridazine, [1,2,4]triazolo[1,5-a]pyrazine, [1,2,4]triazolo[1,5 -a]pyridine, imidazo[1,2-c]pyrimidine, imidazo[1,2-b]pyridazine, [1,2,4]triazolo[1,5-c]pyrimidine, 1-methyl- 1H-indole, imidazo[1,2-a]pyrazine, pyrazolo[1,5-a]pyridine and [1,2,4]triazolo[4,3-a]pyridine.

The term "trialkylsilyl" includes 3 branched and/or straight chain alkyl groups attached to and through a silicon atom, such as trimethylsilyl, triethylsilyl and tert-butyl Base-dimethylsilyl. "Halotrialkylsilyl" means that at least one of the three alkyl groups is partially or completely substituted by the same or different halogen atoms. The term "alkoxytrialkylsilyl" means that at least one of the three alkyl groups is substituted by one or more alkoxy groups which may be the same or different. The term "trialkylsilyloxy" denotes a functional group of a trialkylsilyl group linked via oxygen.

Non-limiting examples of "alkylcarbonyl" include C(O) _CH3 , C(O) _{CH2CH2CH3 ,} and C( _O )CH( _CH3 ) ₂ . Non-limiting examples of "alkoxycarbonyl" include CH ₃ OC(=O), CH ₃ CH ₂ OC(=O), CH ₃ CH ₂ CH ₂ OC(=O), (CH ₃ ) ₂ CHOC(= O) and the different isomers of butaneoxycarbonyl or pentaneoxycarbonyl. Non-limiting examples of "alkylaminocarbonyl" include CH ₃ NHC(=0), CH ₃ CH ₂ NHC(=0), CH ₃ CH ₂ CH ₂ NHC(=0), (CH ₃ ) ₂ CHNHC( =0) and the different isomers of butylaminocarbonyl or pentylaminocarbonyl. Non-limiting examples of "dialkylaminocarbonyl" include (CH ₃ ) ₂ NC(=0), (CH ₃ CH ₂ ) ₂ NC(=0), CH ₃ CH ₂ (CH ₃ )NC(=0 ), CH ₃ CH ₂ CH ₂ (CH ₃ )NC(=O), and (CH ₃ ) ₂ CHN(CH ₃ )C(=O). Non-limiting examples of " _{alkoxyalkylcarbonyl} " include _CH3OCH2C ( ₌ O ₎ , _CH3OCH2CH2C (=O) _{, CH3CH2OCH2C} (= _O ), _{CH3 CH2CH2CH2OCH2C} ( ₌ 0) _{and CH3CH2OCH2CH2C (} = _{0 ) .} Non-limiting examples of "alkylsulfanylcarbonyl" include CH ₃ SCH ₂ C(=0), CH ₃ SCH ₂ CH ₂ C(=0), CH ₃ CH ₂ SCH ₂ C(=0), CH _{3 CH2CH2CH2SCH2C ( =} 0) and _{CH3CH2SCH2CH2C ( =} 0 _{) .} The terms haloalkylsulfonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkylamino, etc. are similarly defined.

Non-limiting examples of "alkylaminoalkylcarbonyl" include CH ₃ NHCH ₂ C(=0 ₎ , CH ₃ NHCH ₂ CH ₂ C(=0), CH ₃ CH 2 NHCH ₂ C(=0), CH ₃ CH ₂ CH ₂ CH ₂ NHCH ₂ C(=0) and CH ₃ CH ₂ NHCH ₂ CH ₂ C(=0).

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

The term "sulfuramide" refers to A-R'C=SNR''-B, wherein R' and R'' represent substituents, and A and B represent any groups.

The total number of carbon atoms in a substituent is indicated by the prefix "C _i -C _j ", where i and j are numbers from 1 to 21. For example, C ₁ -C ₃ alkylsulfonyl means methylsulfonyl to propanesulfonyl; C ₂ alkoxyalkyl means CH ₃ OCH ₂ ; C ₃ alkoxyalkyl means for example CH ₃ CH(OCH ₃ ), CH ₃ OCH ₂ CH ₂ or CH ₃ CH ₂ OCH ₂ ; C ₄ alkoxyalkyl refers to various isomers of alkyl substituted by alkoxy groups containing a total of 4 carbon atoms, examples include CH ₃ CH ₂ CH ₂ OCH ₂ and CH ₃ CH ₂ OCH ₂ CH ₂ . In the above description, when the compound of formula (I) consists of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacing hydrogen on said carbon or nitrogen.

When a compound is substituted by a substituent with a subscript indicating that the number of said substituents may exceed 1, then said substituents (when they exceed 1) are independently selected from the defined substituents Group. Furthermore, when the subscript _m in (R) m represents an integer ranging from, for example, 0 to 4, then the number of substituents may be selected from an integer ranging from 0 to 4.

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

The embodiments herein and their various features and advantageous details are explained with reference to the non-limiting examples in the description. 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 merely to facilitate an understanding of ways in which the embodiments herein may be practiced and to further enable those of ordinary skill in the art to practice the embodiments herein. Therefore, these examples should not be construed as limiting the scope of the embodiments herein.

The description of specific embodiments will fully reveal the general nature of the embodiments here, and others can easily modify and/or adapt them to specific embodiments for various applications by applying existing knowledge without departing from the general concept Therefore, such adaptations and modifications should and are intended to be understood within the meaning and range of equivalence of the disclosed embodiments. It is to be understood that the phraseology or terms used herein are for the purpose of description rather than limitation. Therefore, while the embodiments herein have been described in terms of preferred embodiments, those of ordinary skill in the art will recognize that the embodiments herein can be modified within the spirit and scope of the embodiments described implement.

Any discussion of documents, acts, materials, devices, objects, etc. in the specification is intended only to provide a background to the case. It should not be taken as an acknowledgment that any or all of these matters formed part of the prior art base or were general knowledge in the field relevant to this case that existed anywhere before the priority date of this case.

Although the numerical values mentioned in the description and description/claims may constitute a key part of the present invention, any deviation from these numerical values shall still fall within the scope of the present invention if the deviation follows the same scientific principles as disclosed in the present invention. The compounds according to the invention may, if appropriate, exist as mixtures of the different possible isomeric forms, especially stereoisomers, for example E and Z, threo and erythro, and also optical isomers. But there are also tautomers if appropriate. Any desired mixtures of E and Z isomers, threo and erythro isomers and optical isomers and possible tautomeric forms are disclosed and claimed.

The term "pest" as used for the purposes herein includes, but is not limited to, fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, Insects and rodents. In addition, pests are animals that are harmful to humans or associated with humans (including crops, livestock and forestry).

The term "plants" is understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants, including genetically modified plants, including plant cultivars protected and not protected by plant breeders' rights, obtainable by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or a combination of these methods .

For the purposes of the present invention, the term "plant" includes living organisms of the kind exemplified by trees, shrubs, herbs, grasses, ferns and mosses, which normally grow on a site and absorb water and all of their It needs substances and synthesizes nutrients in its leaves through photosynthesis.

Examples of "plants" for the purposes of the present invention include, but are not limited to, agricultural crops (such as wheat, rye, barley, triticale, oats or rice); sugar beets (such as sugar beet or fodder beet); fruits and fruit trees (such as pear fruit, stone or soft fruit (such as apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries); legumes (such as lentils, peas, alfalfa or soybeans); oil plants (such as canola, mustard, olive, sunflower, coconut, cocoa beans, castor oil plants, oil palm, peanuts, or soybeans); cucurbits (such as squash, cucumber, or melon); fiber plants (such as cotton, flax, hemp, or jute) ; citrus fruits and citrus trees (such as oranges, lemons, grapefruits, or oranges); any garden plant; vegetables (such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, cucurbits, or peppers); laurel plants of the family Cucurbitaceae; oleaginous plants; energy and raw material plants (such as cereals, corn, soybeans, other legumes, canola, sugar cane or oil palm); tobacco; nuts; coffee ; tea; cocoa; bananas; pepper; vines (table and brewing grapes); hops (hop); turf; sweet leaves (also known as stevia); natural rubber plants or ornamental and forestry plants (e.g. , broad-leaved or evergreen plants (such as conifers)); and plant propagation material (such as seeds) and crop material of these plants.

Preferably, plants for the purposes of the present invention include, but are not limited to, cereals, corn, rice, soybeans and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, Cucurbitaceae , 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 intended for human and animal use.

The term "plant parts" is understood to mean all parts and organs of above- and below-ground plants. For the purposes of the present invention, the term plant part includes, but is not limited to, cuttings, leaves, shoots, tubers, flowers, seeds, branches, roots (including taproots, lateral roots, root hairs, root tips, root caps, rhizomes), Branches, shoots, fruits, fruiting bodies, bark, stems, buds, auxiliary buds, meristems, nodes and internodes.

The term "lotus thereof" includes the surroundings of soil, plants or plant parts and equipment or implements used before, during or after sowing/planting plants or plant parts.

The compound(s) of the present invention are applied to plants or plant material or their locus in compositions optionally containing other compatible compounds, including by techniques known to those of ordinary skill in the art, including but not limited to Spraying, coating, dipping, fumigating, impregnating, injecting and dusting.

The term "applied" means attached to a plant or plant part by physical or chemical (including dipping) means.

Fused heterocyclic compounds and their use as pest control agents are described in the prior art, inter alia PCT Patent Publication No. WO2020/250183, wherein Q is described as a fused bicyclic ring. The present invention provides compounds of formula (I), wherein Q is a monocyclic six-membered heterocyclic ring. It has now been surprisingly found that certain novel insecticidally active fused heterocyclic compounds having sulfur-containing substituents which are the subject of the present invention have advantageous properties as expected to be more favorable as insecticides. It has now surprisingly been found that the novel compounds, wherein Q represents a monocyclic six-membered heterocycle, are effective against a wider range of pathogens than the compounds disclosed by the prior art.

式(I) 其中， R ¹係選自由C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基及C ₃-C ₈-環烷基-C ₁-C ₆-烷基所組成之群組； Y係獨立地選自O或NR ^Y； R ^Y係選自由氫、腈基、C ₁-C ₄-烷基、C ₂-C ₄-烯基、C ₂-C ₄-炔基、C ₁-C ₄-鹵烷基、C ₂-C ₄-鹵烯基、C ₃-C ₅-環烷基及C ₃-C ₅-環烷基-C ₁-C ₃-烷基所組成之群組； A代表N或CR ²； G ¹及G ²代表N或C；當兩個G同時均不為氮時； R ²係選自由氫、鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR ⁴、CR′′=NR ⁵、NR ⁵R ⁶、S(O) _0-2R ⁷、C(=O)R ⁸、S(O) _0-1R ⁹=NR ¹⁰、N=S(O) _0-1(R ⁹) ₂、P(=O)(OR′′) ₂、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組；其中各脂族基團可選擇性地被一個或多個R ^2a基團所取代，R ²之環基團可選擇性地被一個或多個R ^2b基團所取代； R ^2a係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₃-C ₈-環烷基、OR ⁴、CR′′=NR ⁵、NR ⁵R ⁶、S(O) _0-2R ⁷、C(=O)R ⁸、S(O) _0-1R ⁹=NR ¹⁰、N=S(O) _0-1(R ⁹) ₂、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ^2b係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR ⁴、CR′′=NR ⁵、NR ⁵R ⁶、S(O) _0-2R ⁷、C(=O)R ⁸、Si(R′′) ₃、S(O) _0-1R ⁹=NR ¹⁰及N=S(O) _0-1(R ⁹) ₂所組成之群組；或 兩個R ^2a或兩個R ^2b取代基與其所連接的原子或與其他原子一起形成三至七員環，該其他原子係選自由以下所組成之群組：C、N、O以及S，且選擇性地包含1至3個選自由C(=O)、C(=S)、S(O) _0-2及Si(R′) ₂所組成之群組的環員 (ring members)，該三至七員環的部分可被一個或多個R ^2ab基團所取代； R ^2ab係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR ⁴、NR ⁵R ⁶、S(O) _0-2R ⁷、S(O) _0-1R ⁹=NR ¹⁰、N=S(O) _0-1(R ⁹) ₂、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； Q代表六員雜環，其可選擇性地被一個或多個R ³基團所取代； R ³係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR ⁴、CR′′=NR ⁵、NR ⁵R ⁶、S(O) _0-2R ⁷、C(=O)R ⁸、S(O) _0-1R ⁹=NR ¹⁰、N=S(O) _0-1(R ⁹) ₂、P(=O)(OR′′) ₂、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組；其中各脂族基團可選擇性地被一個或多個R ^3a基團所取代，R ³之環基團可選擇性地被一個或多個R ^3b基團所取代； R ^3a係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₃-C ₈-環烷基、OR ⁴、CR′′=NR ⁵、NR ⁵R ⁶、S(O) _0-2R ⁷、C(=O)R ⁸、S(O) _0-1R ⁹=NR ¹⁰、N=S(O) _0-1(R ⁹) ₂、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ^3b係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR ⁴、C(R′′) ₂=NR ⁵R ⁶、C(R′′) ₂-OR ⁴、CR′′=NR ⁵、NR ⁵R ⁶、S(O) _0-2R ⁷、C(=O)R ⁸、S(O) _0-1R ⁹=NR ¹⁰、N=S(O) _0-1(R ⁹) ₂、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； 兩個R ^3a或兩個R ^3b與其所連接的原子或與其他原子一起形成三至七員環，該其他原子係選自由以下所組成之群組：C、N、O以及S，且選擇性地包含1至3個選自由C(=O)、C(=S)、S(O) _m及Si(R′′) ₂所組成之群組的環員，該三至七員環的部分可被一個或多個R ^3ab基團所取代；其中R ^3ab係選自由氫、鹵素、腈基、C ₁-C ₆-烷基、C ₁-C ₆-鹵烷基、C ₃-C ₈-環烷基、OR ⁴、NR ⁵R ⁶及S(O) _0-2R ⁷所組成之群組； Z代表直接鍵結 (direct bond)或O； 環E代表與環D稠合的五或六員雜環；其中該環E選擇性地被一個或多個R ¹¹基團所取代； R ¹¹係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR ⁴、CR′′=NR ⁵、NR ⁵R ⁶、S(O) _0-2R ⁷、C(=O)R ⁸、S(O) _0-1R ⁹=NR ¹⁰、N=S(O) _0-1(R ⁹) ₂、P(=O)(OR′′) ₂、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組；其中各脂族基團可選擇性地被一個或多個R ^11a基團所取代，R ¹¹之環基團可選擇性地被一個或多個R ^11b基團所取代； R ^11a係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₃-C ₈-環烷基、OR ⁴、CR′′=NR ⁵、NR ⁵R ⁶、S(O) _0-2R ⁷、C(=O)R ⁸、S(O) _0-1R ⁹=NR ¹⁰、N=S(O) _0-1(R ⁹) ₂、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ^11b係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR ⁴、C(R′′) ₂-NR ⁵R ⁶、C(R′′) ₂-OR ⁴、CR′′=NR ⁵、NR ⁵R ⁶、S(O) _0-2R ⁷、C(=O)R ⁸、S(O) _0-1R ⁹=NR ¹⁰、N=S(O) _0-1(R ⁹) ₂、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ⁴係選自由氫、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、S(O) ₂R ⁷、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組；其中各脂族基團可選擇性地被R ^4a基團所取代，R ⁴之環基團可選擇性地被一個或多個R ^4b基團所取代； R ^4a係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₃-C ₈-環烷基、OR′′、NR′R′′、S(O) _0-2R′、C(=O)R′、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ^4b係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR′′、NR′R′′、S(O) _0-2R′、C(=O)R′、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ⁵係選自由氫、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR ⁴、NR′R′′、S(O) _0-2R ⁷、C(=O)R ⁸、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組；其中各脂族基團可選擇性地被R ^5a基團所取代，R ⁵之環基團可選擇性地被一個或多個R ^5b基團所取代； R ^5a係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₃-C ₈-環烷基、OR′′、NR′R′′、S(O) _0-2R′、C(=O)R′、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ^5b係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR′′、NR′R′′、S(O) _0-2R′、Si(R′′) ₃、C(=O)R′、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ⁶係選自由氫、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₁-C ₆-環烷基及C(=O)R ⁸所組成之群組；或 R ⁵及R ⁶與其所連接的原子或與其他原子可一起形成四至七員環，該其他原子係選自由以下所組成之群組：C、N、O、C(=O)、C(=S)、S(O) _0-2及Si(R′′) ₂，該四至七員非芳香環的部分選擇性地被一個或多個R′基團所取代； R ⁷係選自由C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、NR ⁵R ⁶、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組；其中各脂族基團可選擇性地被一個或多個R ^7a基團所取代，R ⁷之環基團可選擇性地被一個或多個R ^7b基團所取代； R ^7a係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₃-C ₈-環烷基、OR′′、NR′R′′、S(O) _0-2R′、C(=O)R′、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ^7b係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR′′、NR′R′′、S(O) _0-2R′、C(=O)R′、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ⁸係選自由氫、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR ⁴、NR ⁵R ⁶、N=S(O) _0-1(R ⁹) ₂、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組；其中各脂族基團可選擇性地被一個或多個R ^8a基團所取代，R ⁸之環基團可選擇性地被一個或多個R ^8b基團所取代； R ^8a係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₃-C ₈-環烷基、OR′′、NR′R′′、S(O) _0-2R′、C(=O)R′、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ^8b係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR′′、NR′R′′、S(O) _0-2R′、C(=O)R′、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ⁹係選自由C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₆-環烷基及C(=O)R ⁸所組成之群組； R ¹⁰係選自由氫、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、Si(R′′) ₃、S(O) _0-2R ⁷及C(=O)R ⁸所組成之群組； 兩個R ₉取代基或R ₉及R ₁₀取代基與其所連接的原子或與其他原子一起形成四至七員環，該其他原子係選自由以下所組成之群組：C、N、O以及S，且選擇性地包含1至3個選自由C(=O)、C(=S)、S(O) _0-2及Si(R′′) ₂所組成之群組的環員，該四至七員環的部分可被一個或多個R′基團所取代； R′係選自由R′′、OR′′、N(R′′) ₂、S(O) _0-2R′′、C(=O)R′′、C(=O)OR′′及C(=O)N(R′′) ₂所組成之群組； R′′係選自由氫、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基及C ₃-C ₈-環烷基所組成之群組；其中各R′′可選擇性地被鹵素所取代； R ¹至R ¹¹、R ^2a、R ^2b、R ^2ab、R ^3a、R ^3b、R ^3ab、R ^4a、R ^4b、R ^5a、R ^5b、R ^7a、R ^7b、R ^8a及R ^8b中的各基團可選擇性地被一個或多個選自由鹵素、腈基、R′′、OR′′、SR′′、N(R′′) ₂、COOR′′及CON(R′′) ₂所組成之群組的基團所取代； m為0～2之整數； 或其立體異構物或鹽。 Accordingly, the present invention provides a compound of formula (I),

Formula (I) wherein, R ¹ is selected from C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ The group consisting of -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl and C ₃ -C ₈ -cycloalkyl-C ₁ -C ₆ -alkyl; Y is independently selected from O or NR ^Y ; ^RY is selected from the group consisting of hydrogen, nitrile, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl, The group consisting of C ₂ -C ₄ -haloalkenyl, C ₃ -C ₅ -cycloalkyl and C ₃ -C ₅ -cycloalkyl-C ₁ -C ₃ -alkyl; A represents N or CR ² ; G ¹ and G ² represent N or C; when both G are not nitrogen at the same time; R ² is selected from hydrogen, halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -ene C ₂ -C ₆ -alkynyl, C _{1 -C} 6 -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) _2. P(=O)(OR'') ₂ , Si(R'') ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl The group formed; wherein each aliphatic group can be optionally substituted by one or more R ^2a groups, and the ring group of R ² can be optionally substituted by one or more R ^2b groups; R ^2a is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ - C ₈ -cycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ = NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , Si(R′′) ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -group consisting of heterocyclyl; R ^2b is selected from halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ - C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 The group consisting of R ⁷ , C(=O)R ⁸ , Si(R′′) ₃ , S(O) _0-1 R ⁹ =NR ¹⁰ and N=S(O) _0-1 (R ⁹ ) ₂ or two R ^2a or two R ^2b substituents form a three to seven membered ring with the atom to which they are attached or together with other atoms selected from the group consisting of C, N, O and S, and optionally comprising 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O) _0-2 and Si(R') ₂ ), the part of the three to seven membered ring may be substituted by one or more R ^2ab groups; R ^2ab is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl , C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , NR ⁵ R ⁶ , S( O) _0-2 R ⁷ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , Si(R′′) ₃ , C ₆ -C ₁₀ - A group consisting of aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; Q represents a six-membered heterocyclic ring, which may optionally be replaced by one or more R ³ groups Substitution; R ³ is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ^8. S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , P(=O)(OR′′) ₂ , Si(R′′) ₃ , The group consisting of C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; wherein each aliphatic group may optionally be replaced by one or more R ^3a group, R ³ ring group can be optionally substituted by one or more R ^3b groups; R ^3a is selected from halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ - C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , Si(R′ ') ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ^3b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -Alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkane base, OR ⁴ , C(R′′) ₂ =NR ⁵ R ⁶ , C(R′′) ₂ -OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , Si(R′′) ₃ , C ₆ -C ₁₀ -A group consisting of aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; two R ^3a or two R ^3b together with the atom to which they are attached or together with other atoms form a three For seven-membered rings, the other atoms are selected from the group consisting of C, N, O and S, and optionally contain 1 to 3 atoms selected from C(=O), C(=S), S (O) _m and Si(R'') ₂ ring members of the group consisting of, the part of the three to seven member ring can be replaced by one or more R ^3ab groups; wherein R ^3ab is selected from hydrogen, Halogen, nitrile, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , NR ⁵ R ⁶ and S(O) _0-2 R A group consisting of ⁷ ; Z represents a direct bond (direct bond) or O; Ring E represents a five or six-membered heterocyclic ring fused to Ring D; wherein the ring E is optionally replaced by one or more R ¹¹ groups Substituted by group; R ¹¹ is selected from halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl , C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O )R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , P(=O)(OR′′) ₂ , Si(R′′) _3. The group consisting of C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclic; wherein each aliphatic group can be optionally replaced by one or more Two R ^11a groups are substituted, and the ring group of R ¹¹ can be optionally substituted by one or more R ^11b groups; R ^11a is selected from halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , Si(R ′′) ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ^11b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -Alkyl, C ₂ -C ₆ -Alkenyl, C ₂ -C ₆ -Alkynyl, C ₁ -C ₆ -Haloalkyl, C ₂ -C ₆ -Haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , C(R′′) ₂ -NR ⁵ R ⁶ , C(R′′) ₂ -OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _{0 -2} R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , Si(R′′) ₃ , C The group consisting of ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ⁴ is selected from the group consisting of hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, S(O ) ₂ R ⁷ , the group consisting of Si(R′′) ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; wherein each aliphatic The group group can be optionally substituted by R ^4a group, and the ring group of R ⁴ can be optionally substituted by one or more R ^4b groups; R ^4a is selected from the group consisting of halogen, nitrile, C ₁ - C ₆ -Alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C(=O)R', Si(R'') ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C The group consisting of ₃ -C ₁₀ -heterocyclyl; R ^4b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl , C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R ′, C(=O)R′, Si(R′′) ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl Group; R ⁵ is selected from hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , NR′R′′, S(O) _0-2 R ⁷ , C(=O)R ⁸ , Si(R′′) ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -arylalkyl and C ₃ -C ₁₀ -heterocyclyl group; wherein each aliphatic group can optionally be replaced by R ^5a group Substituted, the ring group of R ⁵ can be optionally substituted by one or more R ^5b groups; R ^5a is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ - Alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R ′, C(=O)R′, Si(R′′) ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl Group; R ^5b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', Si(R'') ₃ , C(= O) the group consisting of R', C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ⁶ is selected from the group consisting of hydrogen, C ₁ -C ₆ -Alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₁ -C ₆ -cyclo A group consisting of alkyl and C(=O)R ⁸ ; or R ⁵ and R ⁶ and the atoms to which they are attached or together with other atoms may form a four to seven membered ring selected from the group consisting of Group: C, N, O, C(=O), C(=S), S(O) _0-2 and Si(R'') ₂ , the part of the four to seven membered non-aromatic ring is optionally replaced by a or multiple R'groups; R ⁷ is selected from C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -halogenyl base, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, NR ⁵ R ⁶ , C The group consisting of ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; wherein each aliphatic group can optionally be replaced by one or more R ^7a The ring group of R ⁷ can be optionally substituted by one or more R ^7b groups; R ^7a is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _{0- 2} The group consisting of R', C(=O)R', C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ^7b is selected from Free halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -halogen Alkenyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C(=O)R', C ₆ -C ₁₀ -aryl, The group consisting of C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ⁸ is selected from the group consisting of hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , NR ⁵ R ⁶ , N=S (O) _0-1 (R ⁹ ) ₂ , the group consisting of C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; wherein each aliphatic The group can be optionally substituted by one or more R ^8a groups, and the ring group of R ⁸ can be optionally substituted by one or more R ^8b groups; R ^8a is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR'' , NR′R′′, S(O) _0-2 R′, C(=O)R′, C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ - The group consisting of heterocyclyl; R ^8b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C(=O )R', C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -arane The group consisting of radical and C ₃ -C ₁₀ -heterocyclyl; R ⁹ is selected from the group consisting of C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C The group consisting of ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₆ -cycloalkyl and C(=O)R ⁸ ; R ¹⁰ is selected from the group consisting of hydrogen, nitrile C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -Cycloalkyl, Si(R'') ₃ , S(O) _0-2 R ⁷ and C(=O)R ⁸ group consisting of; two R ₉ substituents or R ₉ and The R ₁₀ substituent forms a four to seven membered ring with the atom to which it is attached or together with other atoms selected from the group consisting of C, N, O and S, and optionally containing 1 to 3 Ring members selected from the group consisting of C(=O), C(=S), S(O) _0-2 , and Si(R'') ₂ , portions of the four to seven membered rings may be replaced by one or more Substituted by R'groups;R' is selected from R'', OR'', N(R'') ₂ , S(O) _0-2 R'', C(=O)R'', C The group consisting of (=O)OR'' and C(=O)N(R'') ₂ ; R'' is selected from the group consisting of hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkene The group consisting of radical, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl and C ₃ -C ₈ -cycloalkyl; wherein each R'' can be optionally substituted by halogen; Each of R ¹ to R ¹¹ , R ^2a , R ^2b , R ^2ab , R ^3a , R ^{3b , R 3ab , R 4a , R 4b , R 5a , R 5b} , R ^7a , ^{R 7b ,} R ^8a , and R ^8b The group can be optionally represented by one or more groups selected from halogen, nitrile, R'', OR'', SR'', N(R'') ₂ , COOR'' and CON(R'') ₂ Substituted by a group consisting of groups; m is an integer from 0 to 2; or a stereoisomer or salt thereof.

The following examples provide definitions, including preferred definitions, of substituents for compounds of formula (I) according to the present invention. For any of these substituents, any definition given below may be combined with any definition given below or elsewhere herein for any other substituent.

In addition, the examples of the invention described herein can be combined in any way, and the parameters described in the examples are not only related to the compound of formula (I), but also to the starting compounds and intermediates that can be used to prepare the compound of formula (I). related to body compounds.

式(IA) 其中， R ¹、Q、Z、A、G ¹、G ²、E及m係如前述的詳細說明所定義。 In one embodiment, the compound of formula (I) is represented by the compound of formula (IA);

Formula (IA) wherein, R ¹ , Q, Z, A, G ¹ , G ² , E and m are as defined in the foregoing detailed description.

其中， R ¹、Q、Z、R ^Y、A、G ¹、G ²、E及m係如前述的詳細說明所定義。 In another embodiment, the compound of formula (I) is represented by a compound of formula (IB);

Wherein, R ¹ , Q, Z, ^RY , A, G ¹ , G ² , E and m are as defined in the foregoing detailed description.

One embodiment of the present invention provides a compound of formula (I); wherein Z is a direct bond, and R ¹ , Q, Y, A, G ¹ , G ² , E and m are as defined in the foregoing detailed description.

One embodiment of the present invention provides a compound of formula (I); wherein Z is O (oxygen atom), and R ¹ , Q, Y, A, G ¹ , G ² , E and m are as defined in the foregoing detailed description.

In one embodiment, the present invention provides compounds of formula (I), wherein the fused ring system DE comprises at least one nitrogen atom.

In one embodiment, Q is selected from Q1, Q2 or Q3.

其中，A ₁、A ₂、A ₃係獨立地選自C或N，條件是A ₁、A ₂、A ₃中的至少一個不是同時為氮；符號

表示環DE的連接點。 In one embodiment, Q represents a six-membered heteroaromatic ring (heteroaromatic ring or aromatic heterocyclic ring) containing at least one nitrogen atom, and is represented by Q1,

Wherein, A ₁ , A ₂ , A ₃ are independently selected from C or N, provided that at least one of A ₁ , A ₂ , A ₃ is not simultaneously nitrogen; the symbol

Indicates the connection point of ring DE.

In a preferred embodiment, Q1 is selected from Q1a, Q1b, Q1c, Q1d and Q1e.

In one embodiment, Q represents a six-membered heteroaromatic ring (heteroaromatic ring or aromatic heterocyclic ring) containing at least one nitrogen atom, Z represents O (oxygen atom); and Q is connected to ring DE through Z.

； 其中，QZ基團係選擇性地被一個或多個R ³取代。 In a preferred embodiment, Q1 represents a six-membered heteroaromatic ring (heteroaromatic ring or aromatic heterocyclic ring) containing at least one nitrogen atom, Z represents O (oxygen atom); and the Q1Z group is selected from:

; Wherein, the QZ group is optionally substituted by one or more R ³ .

； 其中，Q2基團係選擇性地被一個或多個R ³取代；符號

表示環DE的連接點。 In another embodiment, Q represents a six-membered non-aromatic heterocyclic ring containing at least one nitrogen atom, and is represented by Q2:

; Wherein, Q2 group is selectively replaced by one or more R ³ ; symbol

Indicates the connection point of ring DE.

In a preferred embodiment, Q2 represents a six-membered non-aromatic heterocyclic ring containing at least one nitrogen atom, Z represents a direct bond, and Q2 is connected to ring DE through a nitrogen atom.

其中，符號

表示環DE的連接點。 In a preferred embodiment, Q2 is selected from:

Among them, the symbol

Indicates the connection point of ring DE.

In one embodiment, Q2 represents a six-membered non-aromatic heterocyclic ring containing at least one nitrogen atom, Z represents a direct bond, and Q2 is connected to ring DE through a nitrogen atom.

In a preferred embodiment, Q2 is selected from Q2a, Q2c, Q2d and Q2f, more preferably selected from Q2a and Q2c.

； 其中，Q3基團係選擇性地被一個或多個R ³取代；符號

表示環DE的連接點。 In yet another embodiment, Q represents a six-membered non-aromatic partially unsaturated heterocyclic ring containing at least one nitrogen atom and is represented by Q3:

; Wherein, Q3 group is selectively replaced by one or more R ³ ; symbol

Indicates the connection point of ring DE.

其中，R ³及R ⁵與前述所定義的相同，符號

表示環DE的連接點。 In a preferred embodiment, Q3 is selected from:

Wherein, R ³ and R ⁵ are the same as defined above, and the symbols

Indicates the connection point of ring DE.

In a preferred embodiment, Q3 is selected from Q3a, Q3b, Q3c and Q3f, and R ⁵ is selected from hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₃ -C ₈ -cycloalkyl and C ₃ -C ₈ -cycloalkyl-C ₁ -C ₆ -alkyl; wherein R ⁵ is optionally substituted by one or more halogens.

In another more preferred embodiment, Q3 is selected from Q3aa, Q3ba, Q3ca and Q3fa.

According to a more preferred embodiment, Q represents a six-membered heteroaromatic ring (heteroaromatic ring or aromatic heterocyclic ring) containing at least one nitrogen atom, and Z represents a direct bond.

According to a preferred embodiment, Q is more preferably selected from Q1a, Q1d, Q1e, Q2a, Q2c, Q3a, Q3b, Q3c and Q3f.

其中，#表示與環Q的連接點，且

表示與基團-S(Y) _mR ¹的連接點。 In another embodiment, the fused ring system DE is selected from the group consisting of DE-1 to DE-15:

Among them, # represents the connection point with the ring Q, and

Indicates ^the point of attachment to the group -S(Y) _mR1 .

In a preferred embodiment, the ring DE is selected from DE-1, DE-7 and DE-11, even more preferably from DE-7.

In one embodiment, R ³ is selected from halogen, -S(O) _0-2 C ₁ -C ₆ -haloalkyl, -S(O)(NR ^Y ) C ₁ -C ₆ -haloalkyl, C ₁ -C ₄ haloalkyl and C ₁ -C ₄ haloalkoxy.

In another embodiment, R ³ is selected from C ₁ -C ₄ haloalkyl, preferably from C ₁ -C ₂ haloalkyl, more preferably from CF ₃ .

In yet another embodiment, R ³ is selected from C ₁ -C ₄ haloalkoxy, C ₂ -C ₄ haloalkenyloxy, preferably selected from C ₁ -C ₃ haloalkoxy, more preferably The ground system is selected from -O-CH ₂ CF ₂ CF ₃ .

In yet another embodiment, R ³ is -S(O) _0-2 C ₁ -C ₆ -haloalkyl, more preferably -S(O) _0-2 CF ₃ .

In one embodiment, R ¹¹ is selected from halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ - Haloalkenyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cyanocycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , phenyl, four to six membered heterocyclic groups, preferably is selected from five-membered nitrogen-containing heterocyclic rings.

式(I-1) 其中， R ¹係C ₁-C ₆-烷基或C ₃-環烷基； Y係NR ^Y或O； R ^Y係選自由氫、腈基、C ₁-C ₄-烷基、C ₂-C ₄-烯基、C ₂-C ₄-炔基、C ₁-C ₄-鹵烷基、C ₂-C ₄-鹵烯基、C ₃-C ₅-環烷基及C ₃-C ₅-環烷基-C ₁-C ₃-烷基所組成之群組； Z代表直接鍵結或O； Q代表六員雜環，其可選擇性地被一個或多個R ³基團所取代； R ³係選自由鹵素、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、C ₁-C ₆-鹵烷氧基、S(O) _0-2、C ₁-C ₆-鹵烷基、-S(O) _0-1R ⁹=NR ¹⁰及C ₃-C ₁₀-雜環基所組成之群組；其中R ³之C ₃-C ₁₀-雜環基可選擇性地被一個或多個R ^3b基團所取代； R ^3b係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₁-C ₆-鹵烷基、C ₁-C ₆-鹵烷氧基、S(O) _0-2C ₁-C ₆-烷基及S(O) _0-2C ₁-C ₆-鹵烷基所組成之群組； R ¹¹係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR ⁴、CR′′=NR ⁵、NR ⁵R ⁶、S(O) _0-2R ⁷、C(=O)R ⁸、-S(O) _0-1R ⁹=NR ¹⁰、-N=S(O) _0-1(R ⁹) ₂、-P(=O)(OR′′) ₂、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組；其中各脂族基團可選擇性地被一個或多個R ^11a基團所取代，R ¹¹之環基團可選擇性地被一個或多個R ^11b基團所取代； R ^11a係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₃-C ₈-環烷基、OR ⁴、CR′′=NR ⁵、NR ⁵R ⁶、S(O) _0-2R ⁷、C(=O)R ⁸、S(O) _0-1R ⁹=NR ¹⁰、N=S(O) _0-1(R ⁹) ₂、Si(R′′)3、C ₆- _C10-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ^11b係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR ⁴、C(R′′) ₂-NR ⁵R ⁶、C(R′′) ₂-OR ⁴、CR′′=NR ⁵、NR ⁵R ⁶、S(O) _0-2R ⁷、C(=O)R ⁸、S(O) _0-1R ⁹=NR ¹⁰、N=S(O) _0-1(R ⁹) ₂、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ⁴係選自由氫、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、S(O) ₂R ⁷、Si(R′′) ₃、苯基、苯甲基及C ₃-C ₁₀-雜環基所組成之群組；其中各脂族基團可選擇性地被R ^4a基團所取代，R ⁴之環基團可選擇性地被一個或多個R ^4b基團所取代； R ^4a係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₃-C ₈-環烷基、OR′′、NR′R′′、S(O) _0-2R′、C(=O)R′、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ^4b係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR′′、NR′R′′、S(O) _0-2R′、C(=O)R′、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ⁵係選自由氫、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR ⁴、NR′R′′、S(O) _0-2R ⁷、C(=O)R ⁸、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組；其中各脂族基團可選擇性地被R ^5a基團所取代，R ⁵之環基團可選擇性地被一個或多個R ^5b基團所取代； R ^5a係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₃-C ₈-環烷基、OR′′、NR′R′′、S(O) _0-2R′、C(=O)R′、Si(R′′) ₃、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ^5b係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR′′、NR′R′′、S(O) _0-2R′、Si(R′′) ₃、C(=O)R′、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ⁶係選自由氫、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₁-C ₆-環烷基及C(=O)R ⁸所組成之群組；或 R ⁵及R ⁶與其所連接的原子或與其他原子一起形成四至七員環，該其他原子係選自由以下所組成之群組：C、N、O、C(=O)、C(=S)、S(O) _0-2及Si(R′′) ₂，該四至七員非芳香環的部分選擇性地被一個或多個R′基團所取代； R ⁷係選自由C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、NR ⁵R ⁶、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組；其中各脂族基團可選擇性地被一個或多個R ^7a基團所取代，R ⁷之環基團可選擇性地被一個或多個R ^7b基團所取代； R ^7a係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₃-C ₈-環烷基、OR′′、NR′R′′、S(O) _0-2R′、C(=O)R′、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ^7b係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR′′、NR′R′′、S(O) _0-2R′、C(=O)R′、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ⁸係選自由氫、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR′′、NR ⁵R ⁶、N=S(O) _0-1(R ⁹) ₂、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組；其中各脂族基團可選擇性地被一個或多個R ^8a基團所取代，R ⁸之環基團可選擇性地被一個或多個R ^8b基團所取代； R ^8a係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₃-C ₈-環烷基、OR′′、NR′R′′、S(O) _0-2R′、C(=O)R′、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ^8b係選自由鹵素、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、OR′′、NR′R′′、S(O) _0-2R′、C(=O)R′、C ₆-C ₁₀-芳基、C ₇-C ₁₄-芳烷基及C ₃-C ₁₀-雜環基所組成之群組； R ⁹係選自由C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₆-環烷基及C(=O)R ⁸所組成之群組； R ¹⁰係選自由氫、腈基、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基、C ₂-C ₆-鹵烯基、C ₃-C ₈-環烷基、Si(R′′) ₃、S(O) _0-2R ⁷及C(=O)R ⁸所組成之群組； 兩個R ₉或R ₉及R ₁₀與其所連接的原子或與其他原子一起形成四至七員環，該其他原子係選自由以下所組成之群組：C、N、O、C(=O)、C(=S)、S(O) _0-2及Si(R′′) ₂，該四至七員環的部分可被一個或多個R′基團所取代； R′係選自由R′′、OR′′、N(R′′) ₂、C(=O)R′′、C(=O)OR′′及C(=O)N(R′′) ₂所組成之群組； R′′係選自由氫、C ₁-C ₆-烷基、C ₂-C ₆-烯基、C ₂-C ₆-炔基、C ₁-C ₆-鹵烷基及C ₃-C ₈-環烷基所組成之群組；其中各R′′可選擇性地被鹵素所取代； m為0～2之整數； 或其立體異構物及鹽。 In one embodiment, the compound of formula (I) is represented by the compound of formula (I-1);

Formula (I-1) wherein, R ¹ is C ₁ -C ₆ -alkyl or C ₃ -cycloalkyl; Y is NR ^Y or O; ^RY is selected from hydrogen, nitrile, C ₁ -C ₄ - Alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl, C ₂ -C ₄ -haloalkenyl, C ₃ -C ₅ -cycloalkyl and the group consisting of C ₃ -C ₅ -cycloalkyl-C ₁ -C ₃ -alkyl; Z represents a direct bond or O; Q represents a six-membered heterocyclic ring, which may optionally be surrounded by one or more R ³ group is substituted; R ³ is selected from halogen, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, C ₁ -C ₆ - The group consisting of haloalkoxy, S(O) _0-2 , C ₁ -C ₆ -haloalkyl, -S(O) _0-1 R ⁹ =NR ¹⁰ and C ₃ -C ₁₀ -heterocyclyl Group; wherein the C ³ _{-C 10} -heterocyclic group of R 3 can be optionally substituted by one or more R ^3b groups; R ^3b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -haloalkoxy, S(O) _0-2 C ₁ -C ₆ -alkyl and S(O) _0-2 C ₁ -C ₆ - The group consisting of haloalkyl; R ¹¹ is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , -S(O) _0-1 R ⁹ =NR ¹⁰ , -N=S(O) _0-1 (R ⁹ ) ₂ , -P(=O)(OR′′) _2. The group consisting of Si(R'') ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclic; wherein each aliphatic group It can be optionally substituted by one or more R ^11a groups, and the ring group of R ¹¹ can be optionally substituted by one or more R ^11b groups; R ^11a is selected from halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , CR' ′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , Si(R'')3, C _{6 -C10} -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ^11b is selected from the group consisting of halogen, nitrile C ₁ -C ₆ -alkyl, C _{2 -C} 6 -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , C(R′′) ₂ -NR ⁵ R ⁶ , C(R′′) ₂ -OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S( O) _0-2 R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , Si(R′′) _3. The group consisting of C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ⁴ is selected from hydrogen, C ₁ -C ₆ -alk C ₂ -C ₆ -alkenyl, C _{2 -C} 6 -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, The group consisting of S(O) ₂ R ⁷ , Si(R′′) ₃ , phenyl, benzyl and C ₃ -C ₁₀ -heterocyclyl; wherein each aliphatic group can be optionally replaced by R ^4a group, the ring group of R ⁴ can be optionally substituted by one or more R ^4b groups; R ^4a is selected from halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ - C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _{0 -2} R', C(=O)R', Si(R'') ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl The group consisting of; R ^4b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkane radical, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C(=O)R', Si(R'') ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ⁵ is selected from the group consisting of hydrogen, C ₁ -C ₆ -Alkyl, C ₂ -C ₆ -Alkenyl, C ₂ -C ₆ -Alkynyl, C ₁ -C ₆ -Haloalkyl, C ₂ -C ₆ -Haloalkenyl, C ₃ -C ₈ -Cycloalkyl, OR ⁴ , NR′R′′, S(O) _0-2 R ⁷ , C(=O)R ⁸ , Si(R′′) ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aryl The group consisting of C ₃ -C ₁₀ -heterocyclic group; wherein each aliphatic group can be optionally substituted by R ^5a group, and the ring group of R ⁵ can be optionally replaced by one or more R ^5b group is substituted; R ^5a is selected from halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ - Haloalkyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C(=O)R', Si(R'') ₃ , The group consisting of C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ^5b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ - Alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl , OR'', NR'R'', S(O) _0-2 R', Si(R'') ₃ , C(=O)R', C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -Aralkyl and C ₃ -C ₁₀ -heterocyclyl group; R ⁶ is selected from hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C The group consisting of ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₁ -C ₆ -cycloalkyl and C(=O)R ⁸ ; or R ⁵ and R form ^a four to seven membered ring with the atom to which they are attached or together with other atoms selected from the group consisting of: C, N, O, C(=O), C(=S) , S(O) _0-2 and Si(R'') ₂ , part of the four to seven-membered non-aromatic ring is selectively substituted by one or more R'groups; R ⁷ is selected from C ₁ -C ₆ -Alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cyclo The group consisting of alkyl, NR ⁵ R ⁶ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; wherein each aliphatic group can be selected is optionally substituted by one or more R ^7a groups, and the ring group of R ⁷ can be optionally substituted by one or more R ^7b groups; R ^7a is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -Alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -Haloalkyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C(=O)R', C ₆ -C ₁₀ -aryl The group consisting of C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ^7b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C(=O)R', C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl The group consisting of; R ⁸ is selected from hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR'', NR ⁵ R ⁶ , N=S(O) _0-1 (R ⁹ ) ₂ , C ₆ -C ₁₀ - The group consisting of aryl, C ₇ -C ₁₄ -arylalkyl and C ₃ -C ₁₀ -heterocyclyl; wherein each aliphatic group is optionally substituted by one or more R ^8a groups, The ring group of R ⁸ can be optionally substituted by one or more R ^8b groups; R ^8a is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C (=O)R', C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ^8b is selected from the group consisting of halogen, nitrile , C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C(=O)R', C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ - the group consisting of aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ⁹ is selected from the group consisting of C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkyne The group consisting of C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₆ -cycloalkyl and C(=O)R ⁸ ; R ¹⁰ is selected from Hydrogen, Nitrile, C ₁ -C ₆ -Alkyl, C ₂ -C ₆ -Alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, Si(R′′) ₃ , S(O) _0-2 A group formed by R ⁷ and C(=O)R ⁸ ; two R ₉ or R ₉ and R ₁₀ form a four to seven-membered ring with the atoms they are connected to or with other atoms, and the other atoms are selected from Free from the group consisting of: C, N, O, C(=O), C(=S), S(O) _0-2 and Si(R'') ₂ , the part of the four to seven membered ring can be Substituted by one or more R'groups;R' is selected from the group consisting of R'', OR'', N(R'') ₂ , C(=O)R'', C(=O)OR'' and the group consisting of C(=O)N(R'') ₂ ; R'' is selected from the group consisting of hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -A group consisting of alkynyl, C ₁ -C ₆ -haloalkyl and C ₃ -C ₈ -cycloalkyl; wherein each R'' can be optionally substituted by halogen; m is an integer from 0 to 2 ; or stereoisomers and salts thereof.

In one embodiment, the compound of formula (I-1), wherein the -S(Y) _m R ¹ group represents S(O) _0-2 R ¹ or S(O)(=NR ^Y )R ¹ ; preferably Preferably, S(O) ₂ C ₁ -C ₃ (cyclo)alkyl; wherein, more preferably, the (cyclo)alkyl is selected from ethyl, isopropyl and cyclopropyl.

In a preferred embodiment-A, the compound of formula (I-1), wherein, R ¹ is C ₁ -C ₄ -alkyl or C ₃ -cycloalkyl; Z represents a direct bond or O; preferably , Z is a direct bond; Q is selected from Q1a, Q1d, Q1e, Q2a, Q2c, Q3a, Q3b, Q3c or Q3f; preferably, Q1a, Q1d and Q1e; ^R is selected from halogen, -S(O ) _0-2 C ₁ -C ₄ -haloalkyl, -S(O)(NR ^Y )C ₁ -C ₆ -haloalkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy group; preferably, C ₁ -C ₄ haloalkoxy; R ¹¹ is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₁ -C ₆ - Haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cyanocycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , -S(O) _0-1 R ⁹ =NR ¹⁰ , -N=S(O) _0-1 (R ⁹ ) ₂ , ( Un)substituted phenyl or (un)substituted four to six membered heterocyclyl; R ⁵ is selected from hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, -C(=O)R ⁸ , (un)substituted phenyl or (un)substituted C ₃ -C ₁₀ -heterocyclyl; and R ⁸ is selected from C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl; R ⁶ is selected from hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -cycloalkyl or C(=O) C ₁ -C ₆ alkoxy; R ⁷ is selected from C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, NR ⁵ R ⁶ , (un)substituted phenyl, (un)substituted benzyl or (un)substituted four to six membered heterocyclic groups; R ⁹ is selected from C ₁ -C ₆ -Alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl and C ₃ -C ₈ -cycloalkane The group consisting of radicals; R ¹⁰ is selected from the group consisting of hydrogen, nitrile, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl and C(=O ) The group formed by R ⁸ .

In a more preferred embodiment, the compound of formula (I-1), wherein R ¹¹ is selected from CHF ₂ , CF ₃ , CH ₂ CF ₃ , -NHCH ₂ CH ₃ , -N(CH ₃ )CH ₂ CH ₃ , -NH(C(CH ₃ ) ₃ ), -N(CH ₃ )(C(CH ₃ ) ₃ ), -N(CH ₃ )COCH ₃ , -N(CH ₃ )CO(cyclopropyl), -N =S(O)(CH ₃ ) ₂ , cyclopropyl, cyanocyclopropyl, 3-chloro-pyrazol-1-yl (3-chloro-pyrazol-1-yl), 3-trifluoromethyl- Pyrazol-1-yl (3-trifluoromethyl-pyrazol-1-yl), 1,2,4-triazol-1-yl (1,2,4-triazol-1-yl), pyrimidin-2-yl ( pyrimidin-2-yl), pyridazin-2-yl (pyridazyn-2-yl) or pyridazin-3-yl (pyridazyn-3-yl); wherein R ¹¹ is selectively replaced by F, Cl, CN, methyl Substituted by group or methoxy group.

In another preferred embodiment, the compound of formula (I-1), wherein R ⁴ is selected from hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ - the group consisting of cycloalkyl; wherein R ⁴ is optionally substituted by R ^4a , and R ^4a is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkane radical, C ₃ -C ₈ -cycloalkyl, OR''.

In another preferred embodiment, the compound of formula (I-1), wherein -S(Y) _m R ¹ group represents S(O) _0-2 R ¹ ; preferably, S(O) ₂ C ₁ -C ₂ alkyl; more preferably, S(O) ₂ ethyl.

In yet another preferred embodiment, the compound of formula (I-1), wherein -S(Y) _m R ¹ group represents S(O)(=NR ^Y )R ¹ ; ^RY is hydrogen or C ₁ - C ₃ -alkyl, preferably hydrogen, methyl, ethyl or isopropyl; and R ¹ is C ₁ -C ₃ -alkyl; more preferably R ¹ is methyl, ethyl, isopropyl base; most preferably, R ¹ is ethyl.

In another preferred embodiment-A, the compound of formula (I-1), wherein Z is O.

In one embodiment, the compound of formula (I) is especially selected from: 2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazine-2 -yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one (2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2- yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one); 7-bromo-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoro Propoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (7-bromo-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy )pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); 7-cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3- Pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (7-cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3 -pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); 7-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3- Pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (7-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3 -pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); ((2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy Base) pyrazin-2-yl) pyrazolo[1,5-a]pyrimidin-7-yl)imino)dimethyl-l6-pyridine (((2-(ethylthio)-3-(5- (2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)imino)dimethyl-l6-sulfanone); ((2-(ethylsulfonate Acyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)ylidene Amino) dimethyl-l6-yl (((2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a]pyrimidin-7-yl)imino)dimethyl-l6-sulfanone); N-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoro Propoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine (N-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3 ,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine); 2-(ethylthio)-N-methyl-3-(5-(2,2,3 ,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylthio)-N-methyl-3-(5-( 2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine); 2-(ethylthio)-3-(5-(2,2 ,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)pyrazolo[1,5-a ]pyrimidin-7-amine); 2-(ethylthio)-7-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl) Pyrazolo[1,5-a]pyrazolo[1, 5-a]pyrimidine); 7-ethoxy-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl) Pyrazolo[1,5-a]pyrazolo[1, 5-a]pyrimidine); 2-(ethylsulfonyl)-N-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl )pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylsulfonyl)-N-methyl-3-(5-(2,2,3,3,3-pentafluoro ropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine); 2-(ethylsulfonyl)-N,N-dimethyl-3-(5-(2,2 ,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylsulfonyl)-N,N-dimethyl-3- (5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine); N-(cyclopropylmethyl)-2-( Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine-7- Amine (N-(cyclopropylmethyl)-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7- amine); 2-(ethylsulfonyl)-N-isobutyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazole And[1,5-a]pyrimidin-7-amine (2-(ethylsulfonyl)-N-isobutyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[ 1,5-a]pyrimidin-7-amine); N-(cyclopropylmethyl)-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropane Oxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine (N-(cyclopropylmethyl)-2-(ethylthio)-3-(5-(2,2,3, 3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine); 2-(ethylthio)-N,N-dimethyl-3-(5-(2 ,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylthio)-N,N-dimethyl- 3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine); N-cyclopropyl-2-(ethyl Sulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1 ,5-a]pyrazin-7-amine (N-cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a]pyrimidin-7-amine); N-ethyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazine-2- Base) pyrazolo[1,5-a]pyrimidin-7-amine (N-ethyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2- yl)pyrazolo[1,5-a]pyrimidin-7-amine); N-ethyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoro Propoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine (N-ethyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3 ,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine); (7-cyclopropyl-3-(5-(2,2,3,3,3-penta Fluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(imino)-16-((7-cyclopropyl-3-( 5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(imino)-l6-sulfanone); 6-bromo -2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine ( 6-bromo-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); 2-(ethyl Sulfonyl)-7-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-7-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); 6-cyclopropane Base-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy) Pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (6-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2 -yl)pyrazolo[1,5-a]pyrimidine); 2-(Ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl )pyrazolo[1,5-a]pyrimidine (2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a ]pyrimidine); (6-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a] Pyrazin-2-yl)(ethyl)(imino)-l6-pyrazin ((6-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo [1,5-a]pyrimidin-2-yl)(ethyl)(imino)-l6-sulfanone); 2-(ethylsulfonyl)-3-(5-(2,2,3,3,3 -pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy) pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); N-(tert-butyl)-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3 -pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-6-amine (N-(tert-butyl)-2-(ethylsulfonyl)-3-(5-( 2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-6-amine); 6-bromo-2-(ethylsulfonyl)-3-( 5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (6-bromo-2-(ethylsulfonyl)-3- (5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); 6-cyclopropyl-2-(ethylsulfonyl)-3 -(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (6 -cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine);((2-(B Sulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-6-yl ) imino) dimethyl-l6-pyrazin (((2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a]pyrimidin-6-yl)imino)dimethyl-l6-sulfanone); ethyl ((2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoro Propoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-6-yl)imino)(methyl)-16-(ethyl((2-(ethylsulfonyl)-3 -(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-6-yl)imino)(methyl)-l6-sulfanone); 2- (Ethylsulfonyl)-6-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5- a] pyrimidine (2-(ethylsulfonyl)-6-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); B Base ((2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a] Pyrazin-6-yl)imino)(methyl)-l6-pyrazin (ethyl((2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2- yl)pyrazolo[1,5-a]pyrimidin-6-yl)imino)(methyl)-l6-sulfanone); ((2-(ethylthio)-3-(5-(2,2,3,3 ,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-6-yl)imino)dimethyl-l6-pyridine (((2-(ethylthio )-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazi n-2-yl)pyrazolo[1,5-a]pyrimidin-6-yl)imino)dimethyl-l6-sulfanone); 2-(ethylsulfonyl)-3-(5-(2,2,3 ,3,3-pentafluoropropoxy)pyrazin-2-yl)-6-(pyrimidin-5-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(5 -(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-6-(pyrimidin-5-yl)pyrazolo[1,5-a]pyrimidine); 7-bromo-2-(ethylthio base)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine (7-bromo-2- (ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine); 6-(3,5-difluorophenyl )-2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a ] pyrimidine (6-(3,5-difluorophenyl)-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a ]pyrimidine); 2-(ethylsulfonyl)-6-(4-fluorophenyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazine-2 -yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-6-(4-fluorophenyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2 -yl)pyrazolo[1,5-a]pyrimidine); 1-(2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridine oxazin-2-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethan-1-one (1-(2-(ethylsulfonyl)-3-(5-(2,2,3,3 ,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethan-1-one); 7-bromo-2-(ethylsulfonyl)-3-(6 -(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine (7-bromo-2-(e thylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine); 7-bromo-2-(ethylsulfonyl )-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (7-bromo-2-( ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); N-(tert-butyl)-2-(ethyl Sulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine (N-(tert-butyl)-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7 -amine); 2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-N-(2,2 ,2-Trifluoroethyl)pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin- 2-yl)-N-(2,2,2-trifluoroethyl)pyrazolo[1,5-a]pyrimidin-7-amine); 2-(ethylsulfonyl)-7-(4-fluorophenyl) -3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-7- (4-fluorophenyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); 2-(ethylsulfonyl) -3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylsulfonyl )-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine); 2-(ethylthio)-3 -(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1 ,5-a]pyrazin-5(4H)-one (2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5- a]pyrimidin-5(4H)-one); 2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)- 7-(pyrimidin-2-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl )-7-(pyrimidin-2-yl)pyrazolo[1,5-a]pyrimidine); 7-cyclopropyl-2-(ethylthio)-3-(6-(2,2,3,3, 3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine (7-cyclopropyl-2-(ethylthio)-3-(6-(2,2,3,3 ,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine); 5-bromo-2-(ethylthio)-3-(5-(2,2,3,3,3- Pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (5-bromo-2-(ethylthio)-3-(5-(2,2,3,3,3 -pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); N-(2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy Oxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)cyclopropanecarboxamide (N-(2-(ethylthio)-3-(5-(2,2 ,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)cyclopropanecarboxamide); 7-cyclopropyl-2-(ethylsulfonyl)-3- (6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine (7-cyclopropyl-2-(ethylsulfonyl)-3 -(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine); 2-(ethylthio)-3-(6-(2, 2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-N-(2,2,2-tri Fluoroethyl)pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl) -N-(2,2,2-trifluoroethyl)pyrazolo[1,5-a]pyrimidin-7-amine); N-(tert-butyl)-2-(ethylthio)-3-(6-(2 ,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine (N-(tert-butyl)-2-(ethylthio )-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine); 2-(ethylthio)-3 -(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylthio)- 3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine); 5-bromo-2-(ethylsulfonyl Base)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (5-bromo-2- (ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); 2-(ethylsulfonyl)-3 -(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-N-(2,2,2-trifluoroethyl)pyrazolo[1,5 -a]pyridazin-7-amine (2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-N-(2,2,2-trifluoroethyl )pyrazolo[1,5-a]pyrimidin-7-amine); N-(tert-butyl)-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3- Pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine (N-(tert-butyl)-2-(ethylsulfonyl)-3-(6-(2 ,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidi n-7-amine); 2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7-( Pyrimidin-2-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7 -(pyrimidin-2-yl)pyrazolo[1,5-a]pyrimidine); N-(2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoro Propoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)acetamide (N-(2-(ethylsulfonyl)-3-(5-(2,2, 3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)acetamide); N-(2-(ethylsulfonyl)-3-(5-( 2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)pivalamide (N-(2-( ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)pivalamide); 2-(ethylthio )-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-5-(pyrimidin-2-yl)pyrazolo[1,5-a ]pyrimidine (2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-5-(pyrimidin-2-yl)pyrazolo[1,5-a ]pyrimidine); 2-(ethylsulfonyl)-N,N-dimethyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl )pyrazolo[1,5-a]pyrimidin-5-amine (2-(ethylsulfonyl)-N,N-dimethyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2 -yl)pyrazolo[1,5-a]pyrimidin-5-amine); 2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy) Pyrazin-2-yl)-5-(pyrimidin-2-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3 -pentafluoropropoxy )pyrazin-2-yl)-5-(pyrimidin-2-yl)pyrazolo[1,5-a]pyrimidine); N-(2-(ethylsulfonyl)-3-(5-(2,2 ,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclopropanecarboxamide (N-(2-(ethylsulfonyl) -3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclopropanecarboxamide); 5-cyclopropyl-2- (Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (5 -cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); 5-cyclopropyl- 2-(Ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (5 -cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); (5-cyclopropyl -3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl) (imino)-l6-pyrazin ((5-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-2 -yl)(ethyl)(imino)-l6-sulfanone); N-(2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy) Pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-5-yl)acetamide (N-(2-(ethylsulfonyl)-3-(5-(2,2,3,3, 3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-5-yl)acetamide); 2-(ethylsulfonyl)-N-neopentyl-3-(5-(2 ,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine- 7-amine (2-(ethylsulfonyl)-N-neopentyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7- amine); 2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7-(trifluoromethyl)pyridine Azolo[1,5-a]pyrimidine (2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7-(trifluoromethyl)pyrazolo[1 ,5-a]pyrimidine); 2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7- (Trifluoromethyl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7 -(trifluoromethyl)pyrazolo[1,5-a]pyrimidine); N-((5-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazine- 2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(oxo)-16-sulfenyl)amide (N-((5-cyclopropyl-3-(5 -(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(oxo)-l6-sulfaneylidene)cyanamide); 2- (Ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine-7(4H )-ketone (2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one ); 2,7-bis(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5- a] pyrimidine (2,7-bis(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); (7 -Cyclopropyl-3-(6-(2,2,3 ,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(imino)-l6-pyridine ((7 -cyclopropyl-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(imino)-l6- sulfanone); 2-(ethylsulfonyl)-N-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo [1,5-a]pyrazin-5-amine (2-(ethylsulfonyl)-N-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1 ,5-a]pyrimidin-5-amine); 2-(ethylsulfonyl)-N-neopentyl-3-(5-(2,2,3,3,3-pentafluoropropoxy) Pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-5-amine (2-(ethylsulfonyl)-N-neopentyl-3-(5-(2,2,3,3,3-pentafluoropropoxy )pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-5-amine); 2-(ethylsulfonyl)-5-methyl-3-(5-(2,2,3,3 ,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-5-methyl-3-(5-(2,2,3, 3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); ((2-(ethylsulfonyl)-3-(5-(2,2,3,3,3 -pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-5-yl)imino)dimethyl-l6-pyridine (((2-(ethylsulfonyl)- 3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-5-yl)imino)dimethyl-l6-sulfanone); 2-( Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-N-(2,2,2-trifluoroethyl )pyrazolo[1,5-a]pyrimidin-5-amine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropro poxy)pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)pyrazolo[1,5-a]pyrimidin-5-amine); 2-(ethylsulfonyl)-N-isobutyl -3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-5-amine (2-(ethylsulfonyl )-N-isobutyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-5-amine); 2-(ethyl Sulfonyl)-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)-3-(5-(2,2,3,3,3-pentafluoro Propoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl) -3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); 2-(Ethylsulfonyl)-3-(5 -(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-5-(1H-1,2,4-triazol-1-yl)pyrazol[1,5 -a] pyrimidine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-5-(1H-1,2,4-triazol-1 -yl)pyrazolo[1,5-a]pyrimidine); 2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazine-2 -yl)-5-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-3 -(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-5-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyrazolo[1 ,5-a]pyrimidine); ((2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrimidine Azolo[1,5-a]pyrimidin-7-yl)imino)dimethyl-l6-sulfonyl (((2-(ethylsulfonyl)-3-(6-(2,2,3,3,3 -pentaf luoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-7-yl)imino)dimethyl-l6-sulfanone); ethyl ((2-(ethylsulfonyl)-3-(6- (2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-7-yl)imino)(methyl)-l6 -碸 (ethyl((2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-7-yl) imino)(methyl)-l6-sulfanone); diethyl((2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazine -3-yl)pyrazolo[1,5-a]pyrimidin-7-yl)imino)-l6-sulfonyl (diethyl((2-(ethylsulfonyl)-3-(6-(2,2,3 ,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-7-yl)imino)-l6-sulfanone); N-(2-(ethylsulfonyl)-3- (6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-7-yl)acetamide (N-( 2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-7-yl)acetamide); N-( 2-(Ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine -7-yl)cyclopropaneformamide (N-(2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5- a]pyrimidin-7-yl)cyclopropanecarboxamide); 2-(ethylsulfonyl)-N-methyl-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazine -3-yl)pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylsulfonyl)-N-methyl-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin -3 -yl)pyrazolo[1,5-a]pyrimidin-7-amine); 2-(Ethylsulfonyl)-N-isopropyl-3-(6-(2,2,3,3,3- Pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylsulfonyl)-N-isopropyl-3-(6-(2,2,3 ,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine); 2-(ethylsulfonyl)-3-(6-(2,2,3, 3,3-pentafluoropropoxy)pyridazin-3-yl)-7-(pyrimidin-2-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(6- (2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-7-(pyrimidin-2-yl)pyrazolo[1,5-a]pyrimidine); 2-(ethylsulfonyl)- 3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7-(1H-1,2,4-triazol-1-yl)pyrazole [1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7-(1H-1,2,4 -triazol-1-yl)pyrazolo[1,5-a]pyrimidine); 2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy) Pyrazin-2-yl)-7-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidine (2-( ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl )pyrazolo[1,5-a]pyrimidine); 2-(ethylsulfonyl)-7-(1-methyl-1H-pyrazol-5-yl)-3-(5-(2,2, 3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazol[1,5-a]pyrimidine (2-(ethylsulfonyl)-7-(1-methyl-1H-pyrazol-5-yl )-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine); N- Cyclopropyl-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5 -a] pyridazin-7-amine (N-cyclopropyl-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a ]pyrimidin-7-amine); 2-(ethylsulfonyl)-7-(1-methyl-1H-pyrazol-5-yl)-3-(6-(2,2,3,3, 3-pentafluoropropoxy)pyridazin-3-yl)pyrazol[1,5-a]pyrimidine (2-(ethylsulfonyl)-7-(1-methyl-1H-pyrazol-5-yl)-3- (6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine); 2-(ethylsulfonyl)-7-(1-methyl -3-(trifluoromethyl)-1H-pyrazol-5-yl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyridine Azolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-3-(6-(2,2,3 ,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine); 2-(ethylsulfonyl)-7-(1-methyl-3-(trifluoromethyl) -1H-pyrazol-5-yl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a] Pyrimidine (2-(ethylsulfonyl)-7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin- 2-yl)pyrazolo[1,5-a]pyrimidine); 2-(ethylsulfonyl)-7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl )-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-7 -(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-3-(6-(2,2,3,3,3-pentafluoropropo xy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine); 7-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-penta Fluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidine (7-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy )pyridin-2-yl)pyrazolo[1,5-a]pyrimidine); 2-(ethylsulfonyl)-7-(1-methyl-1H-pyrazol-5-yl)-3-(5 -(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazol[1,5-a]pyrimidine (2-(ethylsulfonyl)-7-(1-methyl-1H- pyrazol-5-yl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidine); 7-cyclopropyl-2- (Ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidine (7-cyclopropyl- 2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidine); (7-(tert-butylamino )-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl )(imino)-l6-yl ((7-(tert-butylamino)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5- a]pyrimidin-2-yl)(ethyl)(imino)-l6-sulfanone); 7-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3- Pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidine (7-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3- pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidine); 2-(ethylsulfonyl)-N-methyl-3-(5-(2,2,3,3,3- Pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylsulfonyl) -N-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine); N-(tert-butyl )-2-(Ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a ]pyridazin-7-amine (N-(tert-butyl)-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5 -a]pyrimidin-7-amine);(7-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1 ,5-a]pyrimidin-2-yl)(ethyl)(imino)-l6-pyridinium ((7-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin- 2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(imino)-l6-sulfanone); 3-(7-cyclopropyl-2-(ethylthio)pyrazolo[ 1,5-a]pyrimidin-3-yl)-1-methyl-6-(2,2,3,3,3-pentafluoropropoxy)pyridin-2(1H)-one (3-(7 -cyclopropyl-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-1-methyl-6-(2,2,3,3,3-pentafluoropropoxy)pyridin-2(1H)-one ); 2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)-N-(2,2,2- Trifluoroethyl)pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl )-N-(2,2,2-trifluoroethyl)pyrazolo[1,5-a]pyrimidin-7-amine); N-ethyl-2-(ethylsulfonyl)-3-(5-(2 ,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine (N-ethyl-2-(ethylsulfonyl)-3-( 5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1, 5-a]pyrimidin-7-amine); N-ethyl-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazine -3-yl)pyrazolo[1,5-a]pyrimidin-7-amine (N-ethyl-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin -3-yl)pyrazolo[1,5-a]pyrimidin-7-amine); (7-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridine -2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(imino)-l6-((7-cyclopropyl-3-(5-(2,2, 3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(imino)-l6-sulfanone); N-ethyl-2-(ethyl Sulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine ( N-ethyl-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine); N -((7-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidine-2 -yl)(ethyl)(oxo)-16-sulfenyl)cyanamide (N-((7-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2 -yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(oxo)-l6-sulfaneylidene)cyanamide); N-((7-cyclopropyl-3-(5-(2,2 ,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(oxo)-16-sulfenyl) Nitrilamide (N-((7-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)( ethyl)(oxo)-l6-sulfaneylidene)cyanamide); 2-(ethylsulfonyl)-3-(5 -(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)-7-(pyrimidin-2-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl )-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)-7-(pyrimidin-2-yl)pyrazolo[1,5-a]pyrimidine); 3-( 7-cyclopropyl-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-1-methyl-6-(2,2,3,3,3- Pentafluoropropoxy)pyridin-2(1H)-one (3-(7-cyclopropyl-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-1-methyl-6-(2 ,2,3,3,3-pentafluoropropoxy)pyridin-2(1H)-one); N-cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3 ,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine (N-cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2 ,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine); N-(cyclopropylmethyl)-2-(ethylsulfonyl)- 3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine (N-(cyclopropylmethyl)- 2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine); 2-(ethyl Sulfonyl)-N-isopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidine -7-amine (2-(ethylsulfonyl)-N-isopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7 -amine); 2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-7-(trifluoromethyl) Pyrazolo[1,5-a]pyrimidine (2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluor (opropoxy)pyridazin-3-yl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine); ((2-(ethylsulfonyl)-3-(5-(2,2,3,3 ,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)imino)dimethyl-l6-pyridine (((2-(ethylsulfonyl) -3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)imino)dimethyl-l6-sulfanone); 2- (Ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine-7-carboxylic acid Ethyl ester (ethyl 2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine-7-carboxylate); 2 -(Ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-7-(trifluoromethyl)pyrazolo [1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-7-(trifluoromethyl)pyrazolo[1,5 -a]pyrimidine); and ethyl 2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazole And[1,5-a]pyrimidine-7-carboxylate (ethyl 2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1 ,5-a] pyrimidine-7-carboxylate).

The term (un)substituted means that said group is unsubstituted, or said group is independently selected from halogen, nitrile, C ₁ -C 6 -alkyl, C 2 -C ₆ -alkenyl, C ₂ -C ₆ -alkenyl, ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, C ₁ -C ₆ -alkoxy and -S(O) _0-2 C ₁ -C ₆ -alkyl substituents are substituted.

The compounds of the present invention may exist as one or more stereoisomers. Various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. Those of ordinary skill in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other isomer or when it is isolated from the other isomer . Furthermore, processes or methods or techniques for separating, concentrating and/or selectively preparing said isomers are known to those having ordinary skill in the art. The compounds of the present invention may exist as a mixture of stereoisomers, as individual stereoisomers, or in optically active forms.

In cases where the compound of formula (I) is or is capable of forming a cation, the anionic portion of the salt may be inorganic or organic. Alternatively, where the compound of formula (I) is or is capable of forming an anion, the cationic portion of the salt may be inorganic or organic.

Examples of the inorganic anionic portion of a salt include, but are not limited to, chloride, bromide, iodide, fluoride, sulfate, phosphate, nitrate, nitrite, bicarbonate, and bisulfate. Examples of organic anion moieties of salts include, but are not limited to: formates, alkanoates, carbonates, acetates, trifluoroacetates, trichloroacetates, propionates, glycolates, thiocyanates, Lactate, Succinate, Malate, Citrate, Benzoate, Cinnamate, Oxalate, Alkyl Sulfate, Alkyl Sulfonate, Aryl Sulfonate, Aryl Disulphonate salts, alkyl phosphonates, aryl phosphonates, aryl diphosphonates, p-toluene sulfonates and salicylates. Examples of inorganic cationic moieties of salts include, but are not limited to, alkali metals and alkaline earth metals. Examples of organic cationic moieties of salts include, but are not limited to, pyridine, methylamine, imidazole, benzimidazole, histidinium, phosphazene, tetramethylammonium, tetrabutylammonium, choline, and trimethylamine.

In one embodiment, the present invention provides a compound of formula (I), its agriculturally acceptable salt, stereoisomer, isomorph or N-oxide thereof and its compound with excipient, inert carrier or any other Essential ingredients (such as surfactants, additives, composition of solid diluents and liquid diluents).

Compounds of formula (I) include all stereoisomers, N-oxides and salts thereof, and usually exist in more than one form, so formula (I) includes all crystalline and non-crystalline forms represented by compounds of formula (I) . Amorphous forms include solid examples, such as waxes and gums, and liquid examples, such as solutions and melts. Crystalline forms include embodiments that represent substantially single crystal types as well as embodiments that represent mixtures of allotropes (ie, different crystal types). The term "polymorph" refers to a specific crystalline form of a compound that can crystallize through different crystalline forms having different molecular arrangements and/or conformations in the crystal lattice. Although allomers can have the same chemical composition, they can also differ in composition due to the presence or absence of co-crystallization water or other molecules, which can be weakly or strongly bound in the crystal lattice. Allomorphs may differ in chemical, physical, and biological properties, such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate, and bioavailability. Those of ordinary skill in the art will understand that an allomorph of a compound represented by formula (I) is a mixture of allomorphs relative to another allomorph or the same isomorph as the compound represented by formula (I) , may exhibit beneficial effects (eg, suitability for preparation of useful formulations, improved biological properties). Preparation and isolation of specific isomorphs of compounds represented by formula (I) can be achieved by methods known to those of ordinary skill in the art, including, for example, crystallization using selected solvents and temperatures.

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

The compounds of the present invention defined by formula (I) and/or table (I) can be prepared by known methods in various ways as described in Scheme-1 to Scheme-15 below. Compounds of the invention can be prepared by the schemes shown below, wherein, unless otherwise stated, each variable is as defined above for compounds of formula (I).

其中，Q、R ¹、A、G ¹、G ²、E及m係如前述所定義。 Process -1 :

Wherein, Q, R ¹ , A, G ¹ , G ² , E and m are as defined above.

Formula (I) compound (its Z represents direct bond, and with formula (IAa) representation) can be obtained from the compound of formula (Int-2b) under standard Suzuki cross-coupling conditions (standard Suzuki cross coupling conditions) with boronic acid or formula (Int-1d) derived from the reaction of borate ester compounds. The Suzuki cross-coupling reaction can be performed in a suitable solvent such as tetrahydrofuran (THF), N,N', dimethylformamide (DMF), 1,2-dimethoxyethane, 1,4-dioxane ) or solvent systems (such as tetrahydrofuran (THF)/water, 1,2-dimethoxyethane/water mixture, 1,4-dioxane/water, etc.), catalyzed by palladium-based catalysts (including but not Limited to [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) ([1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)) or tetrakis(triphenylphosphino) ) Palladium(0) (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. The reaction temperature may preferably range from ambient temperature (20°C) to the boiling point of the reaction mixture, or as described in the literature, at a temperature between 70°C and 150°C under microwave irradiation to generate the formula (I) compound, the above literature can be referred to Chem. Soc. Rev. 2014, 43, 412-443 or PCT Patent Publication No. WO2014070978.

Alternatively, the compound of formula (Int-2b) can be combined with a heteroaryl tin compound of formula (Int-1d) in a catalyst (such as bis(triphenylphosphine)palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(II), (0), 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) chloride, tris(dibenzylideneacetone)dipalladium(0) and palladium(II) acetate), nickel In the presence of catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride) and copper catalysts such as copper(I) iodide and copper(I) chloride, in the presence of bases such as gold hydride, alkali gold carbonate and organic base), in a suitable solvent such as acetonitrile, tetrahydrofuran (THF), N,N'-dimethylformamide (DMF), 1,2-dimethyl Oxyethane, 1,4-dioxane), between 25 °C and the reflux temperature of the solvent, or in the temperature range between 70 °C and 150 °C under microwave irradiation coupling. Ligands and/or inorganic halides can be added to the reaction as desired. Examples of ligands used in the reaction include triphenylphosphine, Xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphine base) ferrocene, 2-(dicyclohexylphosphino)-2',4',6'-triisopropyl-1,1'-biphenyl, 2-aminoethanol, 8-hydroxyquinoline and 1,10-phenanthroline (1,10-phenanthroline). Examples of the inorganic halides used include alkali metal fluorides such as potassium fluoride and sodium fluoride and alkali metal halides such as lithium chloride, sodium chloride and sodium chloride.

其中，R ¹、A、G ¹、G ²、E及m係如前述所定義。 Process -2 :

Wherein, R ¹ , A, G ¹ , G ² , E and m are as defined above.

Scheme-2 represents the preparation method of the compound of formula (Int-2b). The compound of formula (Int-2) can be prepared by literature method (PCT Patent Publication No. WO2020/250183), and the compound of formula (Int-2) can be further converted into formula (22) under Curtius rearrangement conditions compound. Such rearrangement can be achieved using sodium azide or diphenyl azide in the presence of a base such as triethylamine or diisopropylethylamine in a solvent such as methanol, ethanol, tert-butanol or benzene Methanol) at a temperature of about 25 to 150 °C. Compounds of formula (Int-2a) can be synthesized by simple deprotection of the corresponding carbamates under basic or acidic or hydrogenation conditions (depending on the nature of the corresponding carbamates) get. In the case of R'' = tert-butyl, acidic conditions (e.g. hydrochloric acid) can be used in the presence of dioxane or dichloromethane or dichloroethane or chloroform at temperatures ranging from 0 to 120 °C salt or trifluoroacetic acid). When R'' = methyl or ethyl, basic conditions (e.g. lithium hydroxide or sodium hydroxide or potassium hydroxide). Deprotection can be carried out under hydrogenation (e.g. by hydrogen gas) in the presence of palladium metal (e.g. palladium on carbon or palladium(II) hydroxide) in the presence of methanol or ethanol or ethyl acetate at temperatures typically between 1 and at a pressure of 10 bar (bar) and at 25 °C.

(Int-2a) amine derivatives can be obtained by diazotation using, for example, sodium nitrite or tert-butyl nitrite, followed by a suitable copper halide in a suitable solvent (e.g. dichloromethane, 1,2-bis Chloroethane, toluene or water), in the temperature range of 0 to 100 ° C into compounds of formula (Int-2b), where X is a halogen.

Process -3 :

Scheme-3 describes the preparation of stannanes of formula (Int-1d) from the appropriate halide or triflate of the compound of formula (Int-1a) with a reagent such as hexamethyl ditin or triethyltin chloride) in the presence of a catalyst such as tetrakis(triphenylphosphine)palladium(0) in the presence of a base such as potassium carbonate in a suitable solvent such as N, N'-dimethylformamide (DMF)) or a mixture of two or more suitable solvents, between 25 °C and the reflux temperature of each solvent, or between 70 °C and 160 °C The reaction is carried out in the temperature range under microwave irradiation, and the stannane of formula (Int-1d) is prepared.

Alternatively, a compound of formula (Int-1d) can be prepared from a compound of formula (Int-1a) in a suitable aprotic solvent such as tetrahydrofuran (THF) at a temperature range between -100 °C and 25 °C, with Reagents such as n-butyllithium are reacted, and then reacted with reagents such as hexamethanol in a suitable aprotic solvent such as tetrahydrofuran (THF) at a temperature range between -100 °C and 50 °C. base ditin or triethyltin chloride) obtained by reaction.

其中，Q、R ¹、A、G ¹、G ²、E及m係如前述所定義。 Process -4 :

Wherein, Q, R ¹ , A, G ¹ , G ² , E and m are as defined above.

Alternatively, the compound of formula (I) (whose Z represents a direct bond and is represented by a compound of formula (IAa)) can be obtained by a nickel-catalyzed reductive coupling reaction between a compound of formula (Int-2b) and a compound of formula (Int-1a). Get it. The reaction can be controlled by nickel(II) chloride hexahydrate, nickel(II) chloride anhydrous, nickel(II) iodide, nickel(II) ethylene glycol dimethyl ether complex, bis(triphenylphosphine ) nickel(II) chloride or bis(1,5-cyclooctadiene)nickel(0), catalyzed in the presence of an equivalent excess of zinc or manganese metal. Ligands can be used to support each catalyst if desired or suggested. Examples of ligands include, but are not limited to, 1,10-phenanthroline, 4,7-dimethyl-1,10-phenanthroline, or 4,7-dimethoxy-1,10-phenanthroline, 3,4-Dimethyl-1,10-phenanthroline, or 2,2'-bipyridine, or 4,4'-dimethyl-2,2'-bipyridine, or 4,4'-bipyridine tert-butyl-2,2'-bipyridine, or triphenylphosphine, or 1,2-bis(diphenylphosphino)ethane, or 1,3-bis(diphenylphosphino)propane. Any additives may or may not be required in the above reactions. In this case, examples of additives include, but are not limited to, sodium iodide, potassium iodide, lithium chloride, lithium methoxide, trimethylchlorosilane, or magnesium(II) chloride. The reaction can be carried out in a suitable solvent (such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone or N,N'-dimethylpropyleneurea (DMPU)) in the temperature range between 25 °C and 100 °C. Such reactions have been described in the literature, eg J. Org. Chem. , 2014 , 79 , 777-782 or Top. Curr. Chem. ( 2016 ) 374:43.

其中，Q、Z、R ¹、A、G ¹、G ²、E及m係如前述所定義。 Process -5 :

Wherein, Q, Z, R ¹ , A, G ¹ , G ² , E and m are as defined above.

Compounds of formula (IAa-1) can be prepared by reacting compounds of formula (Int-2b) with cyclic amide compounds of formula (Q2) (which can be carried out by literature procedures described in U.S. Patent Publication No. US2019/0327970 preparation). The above transformations can be performed using bases such as alkali gold carbonates, alkali gold hydrides, sodium or potassium tert-butoxide, lithium hexamethyldisilazane, sodium or potassium, diisopropylethylamine, pyridine, 1 ,8-diazabicyclo[5.4.0]undec-7-ene (1,8-diazabicyclo[5.4.0]undec-7-ene), 4-(dimethylamino)pyridine), in appropriate In a solvent (such as acetonitrile, tetrahydrofuran, dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide or N-methyl-2-pyrrolidone), at 25 ° in the temperature range between C and 120 °C.

Alternatively, compounds of formula (IAa-1) can be prepared by metal catalysis. Alternatively, compounds of formula (IAa-1) can be prepared by metal catalysis. Examples of metal catalysts include, but are not limited to, copper catalysts such as copper(I) iodide, copper(I) bromide, copper(I) chloride, copper(I) oxide, copper(I) triflate salt benzene complexes or 2-thiophenecarboxylate copper(I) salts), nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel chloride), and ligands such as 1,10-phenanthroline, 8 -Hydroquinoline, trans-1,2-cyclohexanediamine, trans-1,2-bis(methylamino)cyclohexane, N,N-dimethylethylenediamine, 2,2'-bipyridine , 2-aminoethanol, triphenylphosphine, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, XantPhos ((5-diphenylphosphino) base-9,9-dimethylxanthen-4-yl)diphenylphosphine ((5-di-phenylphosphanyl-9,9-dimethyl-xanthen-4yl)diphenylphosphane)), XPhos (2-dicyclohexyl Phosphino-2',4',6'-triisopropylbiphenyl (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl)), RuPhos (2-dicyclohexylphosphino-2',6 '-Diisopropoxybiphenyl (2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl)), BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (2, 2'-bis(diphenylphosphino)-1,1'-binaphthalene)) or 1,1'-bis(diphenylphosphino)ferrocene (1,1'-bis(diphenylphosphino)ferrocene)). Examples of suitable bases include, but are not limited to, alkali gold carbonate, diisopropylethylamine, pyridine, 1,8-diazabicyclo[5.4.0]undecyl-7-ene, or 4-(dimethyl Amino)pyridine in a suitable solvent (e.g. acetonitrile, dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide or N-methyl-2-pyrrolidone) in the temperature range of 25 °C to 120 °C.

其中，Q、Z、R ¹、A、G ¹、G ²、E及m係如前述所定義。 Process -6 :

Wherein, Q, Z, R ¹ , A, G ¹ , G ² , E and m are as defined above.

Compounds of formula (IAa-2) can be prepared by reacting compounds of formula (Int-2b) with hydroxyl compounds of formula (Int-1c). The reaction is usually in the presence of a base (such as alkali carbonate and alkali gold hydride), in a suitable solvent (including but not limited to acetonitrile, tetrahydrofuran, N,N-dimethylformamide), between 0 and within a temperature range between 150 °C. The compound of formula (Int-3c) can be prepared according to the methods described in PCT Patent Publication No. WO2005/018557, PCT Patent Publication No. WO2009/149188, PCT Patent Publication No. WO2010/104818 and PCT Patent Publication No. WO2015/153304.

Alternatively, the compound of formula (IAa-2) can be prepared by reacting the hydroxyl derivative of (Int-1c) with the compound of formula (Int-2b) in the presence of a metal catalyst and a base. Examples of metal catalysts include, but are not limited to, copper(I) iodide, copper(I) bromide, copper(I) chloride, copper(I) oxide, copper(I) trifluoromethanesulfonate benzene complex, and tetrafluoromethanesulfonate (Acetoform) copper (I), copper (I) 2-thiophene carboxylate; nickel catalysts such as bis(cyclooctadiene) nickel (0) and nickel (II) chloride, preferably by ligand Support, the above ligands such as 1,10-phenanthroline, 8-hydroquinoline, trans-1,2-cyclohexanediamine, trans-1,2-bis(methylamino)cyclohexane, N,N -Dimethylethylenediamine, 2,2'-bipyridine, 2-aminoethanol, triphenylphosphine, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenyl phosphino)propane, XantPhos (5-diphenylphosphino-9,9-dimethylxanthene-4-yl)diphenylphosphine), XPhos (2-dicyclohexylphosphino-2', 4',6'-triisopropylbiphenyl), RuPhos (2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl), BINAP (2,2'-bis(diphenyl phosphino)-1,1'-binaphthyl) or 1,1'-bis(diphenylphosphino)ferrocene. Examples of bases include, but are not limited to, alkali gold carbonate, alkali gold hydride, triethylamine, diisopropylethylamine, pyridine, and 4-(dimethylamino)pyridine. Suitable solvents for carrying out these reactions are acetonitrile, tetrahydrofuran, N,N-dimethylformamide or aromatic hydrocarbons. Typical temperatures for performing such reactions are between 0 and 130 °C.

其中，Q、Z、R ¹、R ^Y、A、G ¹、G ²、E及n係如前述所定義。 Process -7 :

Wherein, Q, Z, R ¹ , ^RY , A, G ¹ , G ² , E and n are as defined above.

As described in Chem. Commun. , 2017 , 53, 2064; Tertahedron Lett. 2005 , 46, 8007 and PCT Patent Publication No. WO2015071180A1, the compound of formula (IB) can pass through the sulfinic compound of formula (IA) whose n=0 It is obtained by sulfimination/sulfoximination.

Process -8 :

According to Scheme-8, the present invention provides a process for the preparation of intermediate compounds of formula (4), starting from the appropriate halide or triflate of formula (Int-1a), wherein Q is as described above definition.

The compound of formula (3) can be obtained by making the compound of formula (Int-1a) and the compound of formula (2) (in this case, R'' is preferably lower alkyl, such as methyl, ethyl or tert-butyl ester) , in alkali (such as alkali gold carbonate (such as sodium, potassium or cesium; hereinafter collectively referred to as alkali gold carbonate), alkali gold hydride (such as sodium hydride or potassium hydride; hereinafter collectively referred to as alkali gold hydride), tert-butanol sodium or potassium, lithium hexamethyldisilazane, sodium or potassium), in an appropriate solvent (such as tetrahydrofuran, dioxane, acetonitrile, dimethylsulfoxide, N,N-dimethylformamide or N,N-dimethylacetamide) at a temperature range between 0 and 120 °C.

Alternatively, compounds of formula (4) can be prepared under metal catalysis in the presence of a base. Useful metal catalysts such as palladium(II) acetate, bis(dibenzylideneacetone)palladium(0) (Pd(dba) ₂ ), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba ) ₃ , which are optionally in the form of chloroform adducts); tetrakis(triphenylphosphine)palladium(0); copper catalysts (such as copper(I) iodide, copper(I) bromide, copper chloride( I), copper(I) oxide, copper(I) trifluoromethanesulfonate benzene complex, copper(I) 2-thiophenecarboxylate); and ligands (e.g. triphenylphosphine, 1,1'- Bis(diphenylphosphino)ferrocene, XantPhos (5-diphenylphosphino-9,9-dimethylxanth-4-yl)diphenylphosphine), XPhos (2-dicyclohexyl Phosphino-2',4',6'-triisopropylbiphenyl), RuPhos (2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl), BINAP (2,2 '-bis(diphenylphosphino)-1,1'-binaphthyl), L-proline, 2-pyridinecarboxylic acid, optionally in the form of its hydrochloride; examples of bases include, but are not limited to, alkali gold Carbonate, sodium or potassium tert-butoxide, lithium, sodium, or lithium hexamethyldisilazane, sodium, or potassium, in an appropriate solvent (such as tetrahydrofuran, dioxane, dimethylsulfoxide, N,N-dimethoxy methylformamide and N,N-dimethylacetamide) in the temperature range between 0 and 150 °C.

The compound of formula (4) can be obtained from the compound of formula (3) through the decarboxylation reaction under basic or acidic conditions to convert the alkyl ester group. Acidic conditions can be achieved by using reagents such as p-toluenesulfonic acid, trifluoroacetic acid, hydrochloric acid, etc.; basic conditions can be achieved by using lithium hydroxide, sodium hydroxide or potassium hydroxide. Suitable solvents for carrying out such reactions are, for example, acetonitrile, dioxane, dimethylsulfoxide, dichloromethane, 1,2-dichloroethane, methanol, ethanol, 2-propanol and water at 25 °C to 150 °C temperature range. Examples of this are described in the literature, eg in European Patent No. EP1674455, European Patent No. EP1548007.

Alternatively, compounds of formula (4) can be formed in a single step by reacting compounds of formula (1 ) with acetonitrile in the presence of a base. Examples of such bases are, for example, n-butyllithium, tert-butyllithium, methyllithium, phenyllithium, or lithium, sodium or potassium hexamethyldisilazane. Suitable solvents for such reactions are eg tetrahydrofuran, methyltetrahydrofuran, diethyl ether in the temperature range between -78 and 0 °C. Such examples are described in the literature, eg Tetrahedron Letters , 2014 , 55, 5963.

其中，Q、R ¹、R ²、X、Y及m係如前述所定義。 Process -9 :

Wherein, Q, R ¹ , R ² , X, Y and m are as defined above.

Described in Scheme-9 is a method for the synthesis of compounds of formula (Q-Int-1aa). The (organosulfanyl) alkene of formula (5) can permeate the nitrile compound of formula (4) and _CS in base (such as alkali gold carbonate, alkali gold hydride, lithium hexamethyldisilazane, sodium or Potassium, sodium hydroxide or potassium hydroxide) in a suitable solvent such as tetrahydrofuran, acetonitrile and N,N-dimethylamide at a temperature range between 0 and 50 °C And formed. Compounds of formula (5) can be cyclized to aminopyrazole derivatives (6) using hydrazine. Such methods are described in the literature, eg in Russian Journal of Organic Chemistry , 2014 , 50(3), 412-421. In an acidic medium using an acid such as acetic acid or p-toluenesulfonic acid, in a suitable solvent such as ethanol, 2-propanol, toluene, xylene, N,N-dimethylformamide, in the presence of In the temperature range between 80 and 130 °C, reagents such as (7) can be used to convert the respective aminopyrazole derivatives into compounds of formula (8). ( Journal of Medicinal Chemistry , 58(18), 7140-7163; 2015 ).

The conversion reaction of the compound of formula (8) into the compound of formula (9) can be carried out in a solvent in the presence of a halogenating agent, in the presence or absence of a base. Examples of solvents include, but are not limited to, acetonitrile, chloroform, tetrahydrofuran, 1,4-dioxane, toluene, N,N-dimethylformamide, and the like. Examples of halogenating agents include, but are not limited to, phosphorus oxychloride, thionyl chloride, phosphorus pentachloride, oxalyl chloride, and the like. Examples of bases include, but are not limited to, N,N-dimethylaniline, diisopropylethylamine, N-methylmorpholine, and the like. The reaction can be carried out at a temperature in the range of 50-200°C.

Compounds of formula (Q-Int-1aa) (wherein Y=0, m=1 (subarium) and/or m=2 (sulfide)) can be oxidized by corresponding sulfides of formula (9), using suitable oxidizing agents and Obtained under conditions well known to those skilled in the art. Oxidizing agents can be used for the above purposes, such as m-chloroperbenzoic acid (mCPBA), hydrogen peroxide/glacial acetic acid, hydrogen peroxide/trifluoroacetic acid, hydrogen peroxide/potassium permanganate, hydrogen peroxide/ P-toluenesulfonyl imidazole, urea hydrogen peroxide/trifluoroacetic acid, potassium persulfate (oxone), sodium periodate, sodium hypochlorite and other organic peracids, etc. Examples of solvents that can be used in the above reaction include halogenated hydrocarbons (such as dichloromethane, chloroform), alcohols (such as methanol and ethanol) and mixtures thereof.

其中，Q、R ¹、R ²、R ⁴、X、Y及m係如前述所定義。 Process -10 :

Wherein, Q, R ¹ , R ² , R ⁴ , X, Y and m are as defined above.

Pyrazole derivatives of formula (6) can be combined with 1,3-dimethyluracil type compounds (1,3-dimethyl uracil type compounds) of formula (10) or alkoxy acrylate derivatives of formula (11) (alkoxyacrylate derivatives), in the presence of a base, undergo cyclocondensations (cyclocondensations) to obtain pyrimidin-5-one derivatives (pyrimidin-5-one derivatives) of formula (12). Examples of bases include sodium ethoxide, sodium methoxide, sodium or potassium tert-butoxide, alkali gold carbonate, potassium phosphate, and the like. Examples of solvents that can be used in this method include methanol, ethanol, isopropanol, ethylene glycol, N,N-dimethylacetamide, N,N-dimethylformamide, and the like. The corresponding reactions can be carried out at temperatures ranging from about 50°C to about 150°C. Such reactions are well known and alternative reactions are fully described in the literature, for example in J. Org. Chem. 2007, 72, 1046 or PCT Patent Publication No. WO2018081417. For example, as described in PCT Patent Publication No. WO201108689, phosphoryl chloride or bromide can be used to halogenate compounds of formula (12) to give compounds of formula (13). The compound of formula (Q-Int-1ab) can be obtained from the compound of formula (13) in a manner similar to that described in step-5 of Scheme-9.

其中，Q、R ¹、X、Y及m係如前述所定義。 Process -11 :

Wherein, Q, R ¹ , X, Y and m are as defined above.

The malondialdehyde compound of formula (14) of bisacetal protected malonaldehyde can be obtained by using a halogenating agent (such as bromine, iodine, chlorine, N-bromosuccinimide, N-iodide) under acidic conditions. succinimide or N-chlorosuccinimide) to be activated by halogenation under acidic conditions using a compound independently selected from hydrochloric acid, sulfuric acid, methanesulfonic acid, trifluoroacetic acid, tetrafluoroboric acid or p-toluenesulfonic acid Acids, established in a suitable solvent such as water, whereby halogenated aldehydes such as chloromalonal, iodomalonal or bromomalonal of formula (15) are obtained. After step 2, compounds of formula (15) can be reacted with pyrazole derivatives of formula (6) under suitable condensation conditions to give compounds of formula (17). Examples of solvents that can be used in this step include, but are not limited to, dimethyloxide, N,N-dimethylacetamide, N,N-dimethylformamide, and mixtures thereof. The reaction can be carried out at a temperature ranging from about 50°C to about 150°C. The compound of formula (17) can be further easily oxidized to the corresponding sulfone (Y=0, m=1) or sulfide (Y=0, m=2) under the reaction conditions described in step 5 of Scheme-9 , to obtain a compound of formula (Q-Int-lac).

Alternatively, the compound of formula (17) can also be prepared by cyclization of pyrazole derivatives of formula (6) with commercially available 2-halogenated-propondialdehydes of formula (16) under acid-catalyzed conditions. Examples of such acids include, but are not limited to, acetic acid, sulfonic acids (such as PTSA), sulfuric acid, and hydrochloric acid. Examples of solvents that can be used in this step include, but are not limited to, methanol, ethanol, isopropanol, ethylene glycol, and the like. Each reaction can be carried out at a temperature ranging from about 0°C to about 150°C. ( J. Het. Chem. 1974, 44, 51).

其中，Q、R ¹、R ⁴、X、Y及m係如前述所定義。 Process -12 :

Wherein, Q, R ¹ , R ⁴ , X, Y and m are as defined above.

Compounds of formula (Q-Int-1aa/1ab/lac) can be coupled with boronic acid or boronic acid ester compounds of formula (18) under standard Suzuki cross-coupling conditions to give compounds of formula (Q-1aa). Suzuki cross-coupling reactions can be prepared by palladium-based catalysts, including but not limited to [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) or tetrakis(triphenylphosphine)palladium(0) ), in a suitable solvent (such as tetrahydrofuran (THF), N,N'-dimethylformamide (DMF), 1,2-dimethoxyethane, 1,4-dioxane) or solvent system (eg tetrahydrofuran (THF)/water, 1,2-dimethoxyethane/water mixture, 1,4-dioxane/water, etc.) for catalysis. The reaction is usually carried out in the presence of a base such as potassium carbonate, cesium carbonate or potassium phosphate. The reaction temperature can preferably be in the range from ambient temperature (20 °C) to the boiling point of the reaction mixture, as described in the literature, can refer to Chem. Soc. Rev. 2014, 43, 412-443 or PCT patent publication No. WO2014070978.

Alternatively, the compound of formula (Q-1aa) can also be formed by subjecting the corresponding sulfide to the Suzuki conditions described above, followed by oxidation under any given conditions in step 5 of Scheme-9.

其中，Q、R ¹、R ⁵、R ⁶、X、Y及m係如前述所定義。 Process -13 :

Wherein, Q, R ¹ , R ⁵ , R ⁶ , X, Y and m are as defined above.

The compound of formula (Q-1ab) can be prepared by reacting the compound of formula (Q-Int-1aa/1ab/1ac) with the reagent NH=S(O)R ⁵ R ⁶ represented by formula ( 19 ), wherein R ⁵ and R ⁶ are as defined in formula (I). The reaction can be carried out by palladium-based catalysts (examples of which include but are not limited to bis(dibenzylideneacetone)palladium(0)(Pd(dba) ₂ ), tris(dibenzylideneacetone)dipalladium(0)(Pd2 (dba) ₃ , optionally in the form of chloroform adducts) or palladium(II) acetic acid) and ligands such as XantPhos (5-diphenylphosphino-9,9-dimethylxanthene- 4-yl)diphenylphosphine), XPhos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl), RuPhos (2-dicyclohexylphosphino-2', 6'-diisopropoxybiphenyl) or BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)), in a base (such as sodium carbonate, potassium or cesium; tert The catalysis is carried out in the presence of a solvent or mixture of solvents such as dioxane, 1,2-dimethoxyethane or toluene, preferably under an inert atmosphere, in the presence of sodium or potassium butoxide; or potassium phosphate. The reaction temperature can preferably be carried out in the range from room temperature to the boiling point of the reaction mixture, or the reaction can be carried out under microwave irradiation. Such reactions have been described, for example, in PCT Patent Publication No. WO2018/099812, as well as alternative conditions such as iron or copper catalysis. The above reactions and alternative conditions such as iron or copper catalysis have been described in documents such as PCT Patent Publication No. WO2018/099812.

其中，Q、R ¹、R ⁵、R ⁶、X、Y及m係如前述所定義。 Process -14 :

Wherein, Q, R ¹ , R ⁵ , R ⁶ , X, Y and m are as defined above.

The compound of formula (Q-1ac) can be prepared by reacting the compound of formula (Q-Int-1aa/1ab/1ac) with the reagent of formula (20) in the presence of a base, wherein R ^{and R} are as in formula ( as defined in I). Examples of bases include, but are not limited to, sodium, potassium or cesium carbonate, sodium or potassium tert-butoxide, diisopropylethylamine, triethylamine or DBU, in a mixture selected from tetrahydrofuran, N,N-dimethyl solvents such as methyl formamide or acetonitrile. The reaction can be carried out at a temperature in the range of about 25 to about 130°C.

Alternatively, the compound of formula (Q-lac) can be prepared by reacting the compound of formula (Q-Int-1aa/1ab/lac) under the catalytic conditions described in step 1 of Scheme-13.

其中，Q、R ¹、Y、R ⁴、X及m係如前述所定義。 Process -15 :

Wherein, Q, R ¹ , Y, R ⁴ , X and m are as defined above.

The compound of formula (Q-1ad) can be prepared by reacting the compound of formula (Q-Int-1aa/1ab/1ac) with the reagent of formula (21) in the presence of a base, wherein ^R is as in formula X defined. Examples of bases include, but are not limited to, alkali gold hydride, alkali gold carbonate, sodium or potassium tert-butoxide, diisopropylethylamine, triethylamine or DBU, whereby tetrahydrofuran, N,N-di Solvents such as methylformamide or acetonitrile. The reaction can be carried out at a temperature in the range of about 25 to about 130°C.

Alternatively, compounds of formula (Q-1ad) can be prepared from compounds of formula (Q-Int-1aa/1ab/lac) using copper-catalyzed conditions. Copper-based catalysts for the above purposes include, for example, copper(I) iodide, copper(I) bromide, copper(I) chloride or copper(I) acetate, and ligands such as 1,10-phenanthroline, 4,7-Dimethyl-1,10-phenanthroline, 4,7-dimethoxy-1,10-phenanthroline, 4,7-diphenyl-1,10-phenanthroline or L - proline, in the presence of a base such as sodium, potassium or cesium carbonate; or sodium or potassium tert-butoxide, in a solvent or solvent mixture such as dioxane, 1,2-dimethoxyethyl alkanes, toluene, acetonitrile or N,N-dimethylformamide), preferably under an inert atmosphere. The reaction temperature is preferably carried out within the temperature range from room temperature to the boiling point of the reaction mixture, or the reaction can be carried out under microwave irradiation.

In another embodiment, the present invention provides a method of preparing a compound of formula (I) or a salt thereof.

Compounds of formula (I), including their stereoisomers, salts and N-oxides, as well as their precursors in the synthesis process, can be prepared by the above methods. If an individual compound cannot be prepared via the above-mentioned routes, it can be prepared via other compounds derived from formula (I) or the respective precursors, or by conventional modification of the synthetic routes described. For example, in individual cases certain compounds of formula (I) can advantageously be prepared by derivatizing other compounds of formula (I), for example by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, Oxidation, etc., or through routine modification of the synthetic route.

The reaction mixture is worked up in a customary manner, for example by mixing with water, separation of the phases and, if appropriate, chromatographic purification of the crude product. Some intermediates and final products were obtained as colorless or light brown viscous oils which were purified or freed of volatile components under reduced pressure and moderately elevated temperature. If intermediates and final products are obtained in solid form, they can also be purified by recrystallization or digestion.

If an individual compound cannot be prepared by the above-mentioned routes, it can be prepared by other compounds derived from formula (I). However, if the individual syntheses result in a mixture of isomers, separation is generally not required, since in some cases the individual isomers may be lost during workup for use or during application (e.g. in the presence of light, free radical generation, under the action of agents, acids or bases) for interconversion. This transformation can also take place after use, for example during phytotreatment among plants to be treated, or in harmful fungi to be controlled.

式(I-1) The compounds of formula (I) in the following Tables A-1 to A-93 can be prepared according to the above-mentioned methods. The following examples are intended to illustrate the invention and show preferred compounds of formula (I) in the form of compounds of formula (I-1).

Formula (I-1)

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-1 provides 28 compounds of formula (I-1) (compounds A-1.001 to A-1.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

For example, A-1.015 is:

   21

1

   12

   22

2

   13

   23

3

   14

   24

4

   15

   25

5

   16

   26

6

   17

   27

7

   18

   28

8 -CHF ₂    19

         9 CF ₂CH ₃    20

         10 CH ₃                   Table B: Substituent definitions for R ¹¹ serial number R ¹¹ 11

twenty one

1

12

twenty two

2

13

twenty three

3

14

twenty four

4

15

25

5

16

26

6

17

27

7

18

28

8 - CHF ₂ 19

9 CF ₂ CH ₃ 20

10 _CH3

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-2 provides 28 compounds of formula (I-1) (compounds A-2.001 to A-2.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-3 provides 28 compounds of formula (I-1) (compounds A-3.001 to A-3.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-4 provides 28 compounds of formula (I-1) (compounds A-4.001 to A-4.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-5 provides 28 compounds of formula (I-1) (compounds A-5.001 to A-5.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-6 provides 28 compounds of formula (I-1) (compounds A-6.001 to A-6.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-7 provides 28 compounds of formula (I-1) (compounds A-7.001 to A-7.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-8 provides 28 compounds of formula (I-1) (compounds A-8.001 to A-8.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-9 provides 28 compounds of formula (I-1) (compounds A-9.001 to A-9.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-10 provides 28 compounds of formula (I-1) (compounds A-10.001 to A-10.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-11 provides 28 compounds of formula (I-1) (compounds A-11.001 to A-11.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-12 provides 28 compounds of formula (I-1) (compounds A-12.001 to A-12.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-13 provides 28 compounds of formula (I-1) (compounds A-13.001 to A-13.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-14 provides 28 compounds of formula (I-1) (compounds A-14.001 to A-14.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-15 provides 28 compounds of formula (I-1) (compounds A-15.001 to A-15.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-16 provides 28 compounds of formula (I-1) (compounds A-16.001 to A-16.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-17 provides 28 compounds of formula (I-1) (compounds A-17.001 to A-17.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-18 provides 28 compounds of formula (I-1) (compounds A-18.001 to A-18.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-19 provides 28 compounds of formula (I-1) (compounds A-19.001 to A-19.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-20 provides 28 compounds of formula (I-1) (compounds A-20.001 to A-20.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-21 provides 28 compounds of formula (I-1) (compounds A-21.001 to A-21.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-22 provides 28 compounds of formula (I-1) (compounds A-22.001 to A-22.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-23 provides 28 compounds of formula (I-1) (compounds A-23.001 to A-23.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-24 provides 28 compounds of formula (I-1) (compounds A-24.001 to A-24.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-25 provides 28 compounds of formula (I-1) (compounds A-25.001 to A-25.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-26 provides 28 compounds of formula (I-1) (compounds A-26.001 to A-26.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-27 provides 28 compounds of formula (I-1) (compounds A-27.001 to A-27.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-28 provides 28 compounds of formula (I-1) (compounds A-28.001 to A-28.028), wherein Q and Z are

, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-29 provides 28 compounds of formula (I-1) (compounds A-29.001 to A-29.028), wherein Q and Z are

, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-30 provides 28 compounds of formula (I-1) (compounds A-30.001 to A-30.028), wherein Q and Z are

, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，-S(Y) _mR ¹為-S(O) ₂Et，且R ¹¹係如表B中所定義。 Table A-31 provides 28 compounds of formula (I-1) (compounds A-31.001 to A-31.028), wherein Q and Z are

, -S(Y) _m R ¹ is -S(O) ₂ Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-32 provides 28 compounds of formula (I-1) (compounds A-32.001 to A-32.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-33 provides 28 compounds of formula (I-1) (compounds A-33.001 to A-33.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-34 provides 28 compounds of formula (I-1) (compounds A-34.001 to A-34.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-35 provides 28 compounds of formula (I-1) (compounds A-35.001 to A-35.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-36 provides 28 compounds of formula (I-1) (compounds A-36.001 to A-36.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-37 provides 28 compounds of formula (I-1) (compounds A-37.001 to A-37.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-38 provides 28 compounds of formula (I-1) (compounds A-38.001 to A-38.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-39 provides 28 compounds of formula (I-1) (compounds A-39.001 to A-39.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-40 provides 28 compounds of formula (I-1) (compounds A-40.001 to A-40.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-41 provides 28 compounds of formula (I-1) (compounds A-41.001 to A-41.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-42 provides 28 compounds of formula (I-1) (compounds A-42.001 to A-42.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-43 provides 28 compounds of formula (I-1) (compounds A-43.001 to A-43.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-44 provides 28 compounds of formula (I-1) (compounds A-44.001 to A-44.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-45 provides 28 compounds of formula (I-1) (compounds A-45.001 to A-45.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-46 provides 28 compounds of formula (I-1) (compounds A-46.001 to A-46.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-47 provides 28 compounds of formula (I-1) (compounds A-47.001 to A-47.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-48 provides 28 compounds of formula (I-1) (compounds A-48.001 to A-48.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-49 provides 28 compounds of formula (I-1) (compounds A-49.001 to A-49.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-50 provides 28 compounds of formula (I-1) (compounds A-50.001 to A-50.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-51 provides 28 compounds of formula (I-1) (compounds A-51.001 to A-51.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-52 provides 28 compounds of formula (I-1) (compounds A-52.001 to A-52.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-53 provides 28 compounds of formula (I-1) (compounds A-53.001 to A-53.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-54 provides 28 compounds of formula (I-1) (compounds A-54.001 to A-54.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-55 provides 28 compounds of formula (I-1) (compounds A-55.001 to A-55.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-56 provides 28 compounds of formula (I-1) (compounds A-56.001 to A-56.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-57 provides 28 compounds of formula (I-1) (compounds A-57.001 to A-57.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-58 provides 28 compounds of formula (I-1) (compounds A-58.001 to A-58.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，-S(Y) _mR ¹為-S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-59 provides 28 compounds of formula (I-1) (compounds A-30.001 to A-30.028), wherein Q and Z are

, -S(Y) _m R ¹ is -S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，-S(Y) _mR ¹為-S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-60 provides 28 compounds of formula (I-1) (compounds A-60.001 to A-60.028), wherein Q and Z are

, -S(Y) _m R ¹ is -S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，-S(Y) _mR ¹為-S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-61 provides 28 compounds of formula (I-1) (compounds A-61.001 to A-61.028), wherein Q and Z are

, -S(Y) _m R ¹ is -S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，-S(Y) _mR ¹為-S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-62 provides 28 compounds of formula (I-1) (compounds A-62.001 to A-62.028), wherein Q and Z are

, -S(Y) _m R ¹ is -S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-63 provides 28 compounds of formula (I-1) (compounds A-63.001 to A-63.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-64 provides 28 compounds of formula (I-1) (compounds A-64.001 to A-64.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-65 provides 28 compounds of formula (I-1) (compounds A-65.001 to A-65.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-66 provides 28 compounds of formula (I-1) (compounds A-66.001 to A-66.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-67 provides 28 compounds of formula (I-1) (compounds A-67.001 to A-67.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-68 provides 28 compounds of formula (I-1) (compounds A-68.001 to A-68.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-69 provides 28 compounds of formula (I-1) (compounds A-69.001 to A-69.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-70 provides 28 compounds of formula (I-1) (compounds A-70.001 to A-70.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-71 provides 28 compounds of formula (I-1) (compounds A-71.001 to A-71.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-72 provides 28 compounds of formula (I-1) (compounds A-72.001 to A-72.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-73 provides 28 compounds of formula (I-1) (compounds A-73.001 to A-73.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-74 provides 28 compounds of formula (I-1) (compounds A-74.001 to A-74.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-75 provides 28 compounds of formula (I-1) (compounds A-75.001 to A-75.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-76 provides 28 compounds of formula (I-1) (compounds A-76.001 to A-76.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-77 provides 28 compounds of formula (I-1) (compounds A-77.001 to A-77.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-78 provides 28 compounds of formula (I-1) (compounds A-78.001 to A-78.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-79 provides 28 compounds of formula (I-1) (compounds A-79.001 to A-79.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-80 provides 28 compounds of formula (I-1) (compounds A-80.001 to A-80.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-81 provides 28 compounds of formula (I-1) (compounds A-81.001 to A-81.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-82 provides 28 compounds of formula (I-1) (compounds A-82.001 to A-82.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-83 provides 28 compounds of formula (I-1) (compounds A-83.001 to A-83.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-84 provides 28 compounds of formula (I-1) (compounds A-84.001 to A-84.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-85 provides 28 compounds of formula (I-1) (compounds A-85.001 to A-85.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-86 provides 28 compounds of formula (I-1) (compounds A-86.001 to A-86.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-87 provides 28 compounds of formula (I-1) (compounds A-87.001 to A-87.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-88 provides 28 compounds of formula (I-1) (compounds A-88.001 to A-88.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-89 provides 28 compounds of formula (I-1) (compounds A-89.001 to A-89.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，Z為直接鍵結，-S(Y) _mR ¹為S(O)(NMe)Et，且R ¹¹係如表B中所定義。 Table A-90 provides 28 compounds of formula (I-1) (compounds A-90.001 to A-90.028), wherein Q is

, Z is a direct bond, -S(Y) _m R ¹ is S(O)(NMe)Et, and R ¹¹ is as defined in Table B.

，-S(Y) _mR ¹為-S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-91 provides 28 compounds of formula (I-1) (compounds A-91.001 to A-91.028), wherein Q and Z are

, -S(Y) _m R ¹ is -S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，-S(Y) _mR ¹為-S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-92 provides 28 compounds of formula (I-1) (compounds A-92.001 to A-92.028), wherein Q and Z are

, -S(Y) _m R ¹ is -S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

，-S(Y) _mR ¹為-S(O)(=NH)Et，且R ¹¹係如表B中所定義。 Table A-93 provides 28 compounds of formula (I-1) (compounds A-93.001 to A-93.028), wherein Q and Z are

, -S(Y) _m R ¹ is -S(O)(=NH)Et, and R ¹¹ is as defined in Table B.

In one embodiment, the present invention provides a composition for controlling or preventing invertebrate pests. The above composition comprises a biologically effective amount of the compound of formula (I), its agronomically acceptable salt, isomer/structural isomer, stereoisomer, diastereomer, mirror isomer, Tautomers, metal complexes, isomers or N-oxides and at least one additional component selected from the group consisting of surfactants and auxiliary agents.

In another embodiment, the above composition further comprises at least one additional bioactive compatible compound selected from the group consisting of fungicides, insecticides, nematocides, acaricides, biopesticides, herbicides , plant growth regulators, antibiotics, fertilizers or nutrients.

In yet another embodiment, the present invention provides a compound of formula (I) or its N-oxide and salt can be converted into conventional types of agricultural chemical composition, such as: solution, emulsion, suspension, powder, powder, ointment, Granules, compressed preparations, capsules and mixtures thereof. Examples of composition types are 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, Wet powders or powders (such as WP, SP, WS, DP, DS), compressed preparations (such as BR, TB, DT), granules (such as WG, SG, GR, FG, GG, MG), insecticidal preparations ( e.g. LN) and gel formulations for the treatment of plant propagation material such as seeds (e.g. GF). These and other formulation types are defined in "Catalogue of pesticide Formulation types and international coding system", Technical Monograph No. 2, 6 ^th Ed. May 2008, CropLife International.

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

Examples of suitable auxiliaries for formulations and/or agrochemical compositions according to the invention are solvents, liquid carriers, solid carriers or extenders, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, enhancers Solvents, penetration enhancers, protective colloids, adhesives, thickeners, humectants, insect repellants, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, defoamers, colorants, thickeners Agents and Adhesives.

Suitable solvents and liquid carriers are water and organic solvents such as medium to high boiling mineral oil fractions such as kerosene, diesel oil; vegetable or animal oils; aliphatic, cyclic and aromatic hydrocarbons such as toluene, paraffin, tetralin, Alkylated naphthalene compounds; alcohols such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; ethylene glycol; dimethylsulfoxide; ketones such as cyclohexanone; esters such as lactate , carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphates; amines; amides such as N-methylpyrrolidone, fatty acid dimethylamide; and mixtures thereof.

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

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

Suitable anionic surfactants are alkali metal, alkaline earth metal or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefinsulfonates, lignosulfonates, sulfonates of fatty acids and oils, ethoxylated alkylphenols Sulfonates of sulfonates, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalene, sulfonates of decyl and tridecylbenzene, sulfonates of naphthalene and alkylnaphthalene, sulfonates sulfosuccinate or sulfosuccinamate. Examples of sulfates are fatty acid and oil sulfates, ethoxylated alkylphenol sulfates, alcohol sulfates, ethoxylated alcohol sulfates or fatty acid ester sulfates. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohol or alkylphenol ethoxylates.

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 which have been alkoxylated with 1 to 50 equivalents, such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters. Ethylene oxide and/or propylene oxide can be used for the alkoxylation reaction, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucosamides 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 polyglycosides. Examples of polymeric surfactants are homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol or vinyl acetate.

Suitable cationic surfactants are quaternary surfactants such as quaternary ammonium compounds having one or two hydrophobic groups, or salts of long chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are block polymers of type A-B or A-B-A comprising polyethylene oxide and polypropylene oxide blocks, or type A-B-C comprising alkanols, polyethylene oxide and polypropylene oxide block polymers. Suitable polyelectrolytes are polyacids or bases. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers. Examples of polybasic bases are polyvinyl amines or polyethylene amines.

Suitable adjuvants are compounds which themselves have negligible or even no pesticidal activity, which improve the biological performance of the compounds of formula (I) on the target. Adjuvants are, for example, surfactants, mineral or vegetable oils and other auxiliaries. Further examples are set out in "Knowles, Adjuvants and added, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5".

Suitable thickeners are polysaccharides (eg Sanxian gum, carboxymethylcellulose), inorganic clays (organically modified or not), polycarboxylates and silicates. Suitable fungicides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones. Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin. Suitable defoamers are silicones, long-chain alcohols and salts of fatty acids. Suitable colorants such as red, blue or green are low water soluble pigments and water soluble dyes. Examples are inorganic colorants (such as iron oxide, titanium oxide, hexacyanoferric) and organic colorants (such as alizarin, azo and phthalocyanine colorants). Suitable tackifiers or adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological or synthetic waxes and cellulose ethers.

The types of compositions and their preparation methods are as follows:

i) Water-soluble concentrates (SL, LS)

10-60 wt% of the compound of formula (I) (or its N-oxide or salt) and 5-15 wt% of wetting agent (such as alcohol alkoxylate) are dissolved in water added to 100 wt% and/ Or water-soluble solvents (such as alcohols). The active substance dissolves on dilution with water.

ii) Dispersible Concentrate (DC)

5-25 wt% of a compound of formula (I) (or its N-oxide or salt) and 1-10 wt% of a dispersant (such as polyvinylpyrrolidone) are dissolved in an organic solvent added to 100 wt% (such as ring Hexanone). Dilution with water gives a dispersion.

iii) Emulsifiable Concentrates (EC)

15-70 wt% of the compound of formula (I) (or its N-oxide or salt) and 5-10 wt% of emulsifiers (such as calcium dodecylbenzenesulfonate and ethoxylated castor oil) are dissolved In water-insoluble organic solvents (such as aromatic hydrocarbons) added to 100 wt%. Dilution with water gives an emulsifier.

iv) Emulsions (EW, EO, ES)

5-40 wt% of the compound of formula (I) (or its N-oxide or salt) and 1-10 wt% of emulsifiers (such as calcium dodecylbenzenesulfonate and ethoxylated castor oil) are dissolved In 20-40 wt% of water-insoluble organic solvents (such as aromatic hydrocarbons). Then, by using an emulsifier, the mixture was added to water up to 100 wt% to make it a uniform emulsion. Dilute with water to obtain an emulsion.

v) Suspensions (SC, OD, FS)

Add 2-10 wt% of dispersant and wetting agent (such as sodium lignosulfonate and alcohol ethoxylate) to 20-60 wt% of the compound of formula (I) (or its N-oxide or salt) , 0.1-2 wt% thickener (such as Sanxian gum) and water added to 100 wt% are pulverized in a stirring ball mill to obtain a good active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS-type compositions, add up to 40 wt% of binder (such as polyvinyl alcohol).

vi) Water Dispersible Granules and Water Soluble Granules (WG, SG)

Add 50-80 wt% of the compound of formula (I) (or its N-oxide or salt) to 100 wt% of dispersant and wetting agent (such as sodium lignosulfonate and alcohol ethoxylate) Finely ground and prepared as water-dispersible or water-soluble granules by technical equipment (eg extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.

vii) Water Dispersible Powder and Water Soluble Powder (WP, SP, WS)

50-80 wt% of the compound of formula (I) (or its N-oxide or salt) is added with 1-5 wt% of dispersant (such as sodium lignosulfonate), 1-3 wt% of wetting agent (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier (e.g. silica gel) in a rotor-stator mill. Dilution with water gives a stable dispersion or solution of the active substance.

viii) Gels (GW, GF)

Add 3-10 wt% of dispersant (such as sodium lignosulfonate) and 1-5 wt% of thickener to 5-25 wt% of the compound of formula (I) (or its N-oxide or salt) (e.g. carboxymethyl cellulose) and water up to 100% by weight are pulverized in an agitating ball mill to obtain a good active substance suspension. Dilution with water gives a stable suspension of the active substance.

ix) Microemulsions (ME)

5-20 wt% of the compound of formula (I) (or its N-oxide or salt) is added to 5-30 wt% of the organic solvent mixture (such as fatty acid dimethylamide and cyclohexanone), 10-25 Surfactant mixture (eg alcohol ethoxylates and arylphenol ethoxylates) in wt % and water up to 100 % wt. The mixture was stirred for one hour to spontaneously generate a thermodynamically stable microemulsion.

x) Microcapsules (CS)

Including 5-50 wt% of the compound of formula (I) (or its N-oxide or salt), 0-40 wt% of water-insoluble organic solvent (such as aromatic hydrocarbon) and 2-15 wt% of acrylic acid monomer (e.g. methyl methacrylate, methacrylic acid and di- or triacrylates) are dispersed into an aqueous solution of protective colloids (e.g. polyvinyl alcohol). Free radical polymerization leads to the formation of poly(meth)acrylate microcapsules. Alternatively, 5-50 wt% of the compound of formula (I) of the present invention, 0-40 wt% of water-insoluble organic solvents (such as aromatic hydrocarbons) and isocyanate monomers (such as diphenylmethylene- 4,4'-diisocyanate) is dispersed into an aqueous solution of a protective colloid such as polyvinyl alcohol. Addition of polyamines such as hexamethylenediamine leads to the formation of polyurea microcapsules. The amount of monomer is 1-10 wt%. Its weight percent is relative to the total CS composition.

xi) Dustable powders (DP, DS)

1-10 wt% of a compound of formula (I) (or N-oxide or salt thereof) is finely ground and intimately mixed with up to 100 wt% of a solid carrier such as finely divided kaolin.

xii) Particles (GR, FG)

0.5-30 wt% of a compound of formula (I) (or N-oxide or salt thereof) is finely ground and combined with a solid carrier (eg silicate) added to 100 wt%. Granulation is achieved by extrusion, spray drying or fluidized bed.

xiii) Ultra Low Volume Liquid (UL)

1-50 wt% of the compound of formula (I) (or N-oxide or salt thereof) is dissolved in an organic solvent (eg aromatic hydrocarbon) added to 100 wt%.

Composition types i) to xiii) can optionally include further additives, such as 0.1-1 wt% bactericide, 5-15 wt% antifreeze, 0.1-1 wt% defoamer and 0.1-1 wt% 1 wt% coloring agent.

In another embodiment, the present invention provides an agricultural chemical composition comprising a compound of formula (I), which comprises 0.01-95% by weight, preferably 0.1-90%, more preferably 0.1-70%, Especially 10-60% active ingredients. The active ingredient is used in a purity (according to NMR spectrum) of 90% to 100%, preferably 95% to 100%.

For the treatment of plant propagation material, especially seeds, water soluble concentrates (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS) are commonly used , water dispersible powders (WS), water soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) for slurry processing. After two to ten times of dilution, the composition has an active substance concentration of 0.01 to 60%, preferably 0.1 to 40%, by weight in the ready-to-use formulation. Application can be done before or during sowing.

The methods for applying the compound of formula (I), its composition and its composition to plant propagation materials, especially seeds, respectively, include: dressing (dressing), coating (coating), granulating, dusting, soaking (soaking) ) and in-furrow application methods. Preferably, the compound of formula (I), its composition and its composition are respectively applied to the plant propagation material by methods that do not induce germination (eg by seed dressing, granulation, coating and dusting).

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

When treating plant propagation material such as seeds, e.g. by dusting, coating or drenching the seeds, 0.1 to 1000 g, preferably 1 to 1000 g, per 100 kg of plant propagation material (preferably seeds) , more preferably 1 to 100 grams, and more preferably 5 to 100 grams of active ingredient is usually required.

When used to protect materials or store products, the amount of active substance used depends on the type of application and the desired effect. Usually the amount used for material protection is 0.001 gram to 2 kilograms, preferably 0.005 gram to 1 kilogram of active substance per cubic meter of treated material.

Different types of oils, wetting agents, adjuvants, fertilizers or micronutrients and other insecticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides) can be used as pre- The mixture is added to the active substance or composition containing the active substance, or, if appropriate, not added until 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.

Users typically apply the compositions of the invention from a pre-dose device, knapsack sprayer, spray can, aircraft spray or irrigation system. Usually, the agrochemical composition is prepared with water, buffer and/or other adjuvants to the required application concentration, so as to obtain the ready-to-use spray liquid or the agrochemical composition of the present invention. Usually, 20 to 6000 liters, preferably 35 to 1000 liters, more preferably 50 to 500 liters of the ready-to-use spray liquid are applied per hectare of agriculturally useful area.

According to one embodiment, the individual components of the composition according to the invention, for example part of a kit or part of a binary or ternary mixture, can be mixed by the user himself in a spray tank or other auxiliary equipment, if appropriate.

The compounds and compositions of the present invention are thus useful agronomically for the protection of field crops from herbivorous invertebrate pests and also non-agronomically for the protection of other horticultural crops and plants from herbivorous invertebrates Infestation by pests. This application includes the protection of crops and other plants (ie agronomic and non-agronomic) that contain genetic material introduced through genetic engineering (ie gene transfer) or modified through mutagenesis to provide advantageous traits.

The compounds of the invention are characterized by good metabolism and/or soil residual patterns and exhibit activity in controlling a range of agronomic and nonagronomic invertebrate pests. The compounds of the present invention are active ingredients with preventive and/or therapeutic value in the field of pest control, and can be used to control insecticide-resistant pests such as insects and mites even at low application rates, and are harmful to warm-blooded animals, fish and plants. It is well tolerated.

In the context of this specification, "invertebrate pest control" means the inhibition of invertebrate pest development (including mortality) that results in a significant reduction in ingestion or other injury or damage by the pest; related terms are similarly defined . As stated in the present specification, the term "invertebrate pest" includes economically important pests such as arthropods, gastropods and nematodes. The term "arthropod" includes insects, mites, spiders, scorpions, centipedes, millipedes, bulb bugs and myriapods.

The term "gastropod" includes snails, slugs and other stalks. The term "nematodes" includes all worms such as roundworms, heartworms and herbivorous nematodes (Nematoda), trematodes (Tematoda), acanthocephala and tapeworms (Cestoda). Those of ordinary skill in the art will recognize that not all compounds are equally effective against all pests.

The compounds of the present invention exhibit activity against economically important pests of agronomic, forest, greenhouse, nursery, ornamental, turfgrass, food and fiber, public and animal health, household and commercial structures, household and stored products. These pests include larvae of the order Lepidoptera, such as armyworms, cutworms, loopers, and heliothines (e.g., fall armyworm, Spodoptera fugiperda J. E. Smith), beet armyworm (beet armyworm, Spodoptera exigua Hbner), cabbage armyworm (black cutworm, Agrotis ipsilon Hufnagel), cabbage looper (cabbage looper, Trichoplusia ni Hbner), tobacco armyworm (tobacco budworm , Heliothis virescens Fabricius)); from borer, casebearer, webworm, coneworm, cabbageworm and roll Skeletonizers (for example, European corn borer ( Ostrinia nubilalis Hbner), navel orangeworm ( Amyelois transitella Walker), corn root webworm ( Crambus caliginosellus Clemens), grass bugs (sod worm, Herpetogrammalicarsisalis Walker); leafrollers, budworms, seed worms and fruit worms of the family Tortricidae (for example, codling moth , Cydia pomonella Linnaeus), grape berry moth ( Endopiza viteana Clemens), oriental fruit moth (Oriental fruit moth, Grapholita molesta Busck)); and many other economically important Lepidoptera (e.g. diamondback moth (diamondback moth, Plutella xylostella Linnaeus), red bollworm (pink bollw orm, Pectinophora gossypiella Saunders), gypsy moth, Lymantria dispar Linnaeus); nymphs and adults of the order Blattodea, which includes those from the Blattellidae and Blattidae families Cockroach (for example, oriental cockroach (oriental cockroach, Blatta orientalis Linnaeus), Asian cockroach (Asian cockroach, Blatella asahinai Mizukubo), German cockroach (German cockroach, Blattella germanica Linnaeus), brown-banded cockroach ( brownbanded cockroach, Supella longipalpa Fabricius), American cockroach (American cockroach, Periplaneta Americana Linnaeus), brown cockroach (brown cockroach, Periplaneta brunnea Burmeister), Madeira cockroach (Madeira cockroach, Leucophaea maderae Fabricius)); Coleoptera ( Defoliator larvae and adults of Coleoptera), which include weevils from the families Anthribidae, Bruchidae and Curculionidae (e.g., boll weevil , Anthonomus grandis Boheman), rice water weevil (rice water weevil, Lissorhoptrus oryzophilus Kuschel), grain weevil (granary weevil, Sitophilus granaries Linnaeus), rice weevil (rice weevil, Sitophilus oryzae Linnaeus)); Chrysomelidae family flea beetle, cucumber beetle, rootworm, leaf beetle, potato beetle and leafminer (e.g., Colorado potato (Colorado potato beetle, Leptinotarsa decemlineara Say), western corn rootworm (western corn rootworm, Diabrotica virgifera virgifera LeConte); chafers and other beetles from the Scaribaeidae family (e.g., Japanese beetle, Popillia japonica Newman) and European chafer, Rhizotrogus majalis Razoumowsky); carpet beetle from the family Dermestidae; wireworm from the family Elateridae; Bark beetle from the family Scolytidae and flour beetle from the family Tenebrionidae. In addition, it includes: adults and larvae of the order Dermaptera, including earwigs from the family Forficulidae (e.g., European earwig, Forficula auricularia Linnaeus), black ground Centipedes (black earwig, Chelisoches morio Fabricius)); adults and nymphs of the orders Hemiptera and Homoptera, such as plant bugs from the Miridae family, plant bugs from the cicada ( Cicadas from the family Cicadidae, leafhoppers from the family Cicadellidae (e.g. Empoasca spp.), from the family Fulgoroidae and from planthoppers (Delphacidae) Planthopper (planthopper) from family Psyllidae, psyllid from family Psyllidae, whitefly from family Aleyrodidae, aphid from family Aphididae , from phylloxera in the family Phylloxeridae, mealybug from the family Pseudococcidae, from the families Coccidae, Diaspididae and Margarodidae ) from the family Scale bug (scale), from the family Tingidae family from the lace bug (lace bug), from the Lygaeidae family from the wheat long bug (chinch bug) (for example, the genus Blissus spp. )) and other seed bugs, spittlebugs from the family Cercopidae, red bugs and cotton bugs from the family Pyrrhocoridae stainer). Also included are adults and larvae of the order Acari (mite), such as spider mite and red mite of the family Tetranychidae (e.g., European red mite, Panonychus ulmi Koch), two spotted spider mite, Tetranychus urticae Koch, McDaniel mite, Tetranychus mcdanieli McGregor), flat mite of the family Tenuipalpidae (e.g., citrus short beard mite (citrus flat mite, Brevipalpus lewisi McGregor), rust mite and bud mite of the family Eriophyidae and other spider mites and mites important to the state of human and animal health, Namely, dust mites of the Epidermoptidae family, ticks of the Ixodidae family (e.g., deer tick, Ixodes scapularis Say), Australian paralysis tick , Ixodes holocyclus Neumann), American dog tick (American dog tick, Dermacentor variabilis Say), lone star tick (lone star tick, Amblyomma americanum Linnaeus) and Psoroptidae, Pyemotidae and Sarcoptidae ) family scab mite (scab mite, itch mite); adults and larvae of Orthoptera (Orthoptera), which include grasshopper (grasshopper), locust (locust) and cricket (cricket) (for example, migratory grasshopper (migratory grasshopper) ( For example, blood black locust ( Melanoplus sanguinipes Fabricius ), different species of grasshopper ( M. differentialis Thomas ), American grasshopper (for example, Schistocerca Americana Drury ), desert locust (de sert locust, Schistocerca gregaria Forskal), migratory locust (Locusta migratoria Linnaeus), house cricket ( Acheta domesticus Linnaeus), mole cricket ( Gryllotalpa spp. )); Adults and larvae, which include leafminers, midges, fruit flies (Tephritidae), frit flies (for example, Oscinella frit Linnaeus), Soil maggots, house flies (e.g., Musca domestica Linnaeus), lesser house flies (e.g., Fannia canicularis Linnaeus), yellow toilet flies ( femoralisStein), stable flies (e.g., Stomoxys calcitra ns Linnaeus), face flies, horn flies, blow flies ( For example, Chrysomya spp. ( Chi ysomya spp. ), Phormia spp. ), and other fly pests, horse flies (e.g. Tabanus spp. ), skin Bot fly (e.g. Gastrophilus spp. , Oestrus spp. ), cattle grub (e.g. Hypoderma spp. ), deer fly ) (e.g. Chrysops spp. ), ked (e.g. Melophagus ovinus Linnaeus) and other Brachycera suborders, mosquitoes (e.g. Aedes spp. , Anopheles spp. , Culex spp. ), black flies (e.g., Prosimulium sp . p. ), gnats ( Simulium spp. )), biting midges, sand flies, sciarids and other Nematocera; of the order Thysanoptera Adults and larvae, which include onion thrips ( Thrips tabaci Lindeman) and other leaf-eating thrips; pests of the order Hymenoptera including ants of the family Formicidae, such as red bowback Red carpenter ant, Camponotus ferrugineus Fabricius, black carpenter ant, Camponotus pennsylvanicus De Geer, Pharaoh ant, Monomorium pharaonis Linnaeus, little fire ant, Wasmannia auropunctata Roger ), fire ant, Solenopsis geminate Fabricius, red imported fire ant, Solenopsis invicta Buren, Argentine ant, Iridomyrmex humilis Mayr, crazy ant, Paratrechina longicornis Latreille, pavement ant ants (pavement ant, Tetramorium caespitum Linnaeus), cornfield ants (cornfield ant, Lasius alienus Frster) and odorous house ants (odorous house ant, Tapinoma sessile Say). Other Hymenoptera include bees (including carpenter bees), hornets, yellow jackets, and wasps; pests of the Isoptera order, which includes eastern subterranean termite, Reticulitermes flavipes Kollar), western subterranean termite, Reticulitermes hesperus Banks, Formosan subterranean termite, Coptotermes formosanus Shiraki, West Indian drywood termite, Incisitermes Snygrider Other economically important termites; pests of the order Thysanura, such as silverfish ( Lepisma saccharina Linnaeus) and silverfish (firebrat, Thermobia domestica Packard); pests of the order Mallophaga and including head lice (head louse, Pediculus humanus capitis De Geer), body louse ( Pediculus humanus Linnaeus), chicken body louse ( Menacanthus stramineus Nitszch), dog biting louse ( Trichodectes canis De Geer), fluff Fluff louse, Goniocotes gallinae De Geer, sheep body louse, Bovicola ovis Schrank, short-nosed cattle louse, Haematopinus eurysternus Nitzsch, long-nosed cattle louse , Linognathus vituli Linnaeus) and other sucking and chewing parasitic lice that attack humans and animals; pests of the order Siphonoptera, which include Oriental rat flea (oriental rat flea, Xenopsylla cheopis Rothschild), cat flea (cat flea, Ctenocephalides felis Bouche), dog flea (dog flea, Ctenocephalides canis Curtis), chicken flea (hen flea, Ceratophyllus gallinae Schrank), sucking flea ( sticktight flea, Echidnophaga gallinacea Westwood), human flea ( Pulex irritans Linnaeus) and other fleas that afflict mammals and birds. Other arthropod pests covered include: spiders of the order Araneae, such as brown recluse spiders, Loxosceles reclusa Gertsch and Mulaik, and black widow spiders (black widow spiders, Latrodectus mactans Fabricius) and gnatflies ( Scutigeromorpha), such as the common house centipede ( Scutigera coleoptrata Linnaeus). The compounds of the present invention are also effective against members of the class Nematodes, Taenias, Trematodes and Acanthocephales, members of which include Strongylida, Ascaridida, Oxyurida, and Brachycephales. Economically important members of the orders Rhabditida, Spirurida and Enoplida, such as, but not limited to, economically important agricultural pests (i.e. root-knot nematodes of the genus Meloidogyne) (root knot nematode), root rot nematode (Pratylenchus) rot nematode (lesion nematode), stub root nematode (Trichodorus) stubby root nematode (stubby root nematode), etc.) and animal and human health harmful animals (ie All economically important flukes, tapeworms and roundworms such as Strongylus vulgaris in horses, Toxocara canis in dogs, Haemonchus contortus in sheep, heartworm in dogs Dirofilaria immitis Leidy, Anoplocephala perfoliata for horses, Fasciola hepatica Linnaeus for ruminants, etc.).

The compounds of the present invention exhibit particularly high activity against harmful animals of the order Lepidoptera, for example, cotton leaf moth ( Alabama argillacea Hbner, cotton leaf worm), fruit tree yellow curler moth ( Archips argyrospila Walker, fruit tree leaf roller), European leaf roller ( A. rosana Linnaeus, European leaf roller) and other tortrix species ( Archips species ), rice stem borer ( Chilo suppressalis Walker, rice stem borer), rice leaf roller ( Cnaphalocrosis medinalis Guenee, rice leaf roller), corn root web caterpillar ( Crambus caliginosellus Clemens, corn root webworm), berry grass net caterpillar ( Crambus teterrellus Zincken, bluegrass webworm), codling moth ( Cydia pomonella Linnaeus, codling moth), Egyptian diamond borer ( Earias insulana Boisduval, spiny bollworm), spotted bollworm ( Earias vittella Fabricius, spotted bollworm), American bollworm ( Helicoveipa armigera Hύbner, American bollworm), corn earworm ( Helicoverpa zea Boddie, corn earworm), tobacco armyworm ( Heliothis virescens Fabricius, tobacco budworm), Herpetogramma licarsisalis Walker, sod webworm, Lobesia botrana Denis and Schiffermüller, grape berry moth, Pectinophora gossypiella Saunders, pink bollworm, citrus Leaf miner ( Phyllocnistis citrella Stainton, citrus leafminer), large white butterfly ( Pieris b rassicae Linnaeus, large white butterfly), Pieris rapae Linnaeus, small white butterfly, diamondback moth ( Plutella xylostella Linnaeus, diamondback moth), beet armyworm ( Spodoptera exigua Hübner, beet armyworm), spodoptera litura Fabricius , tobacco cutworm, cluster caterpillar), fall armyworm ( Spodoptera frugiperda J.E. Smith, fall armyworm), trichoplusia ni Hübner, cabbage looper, and tomato leafminer ( Tuta absoluta Meyrick, tomato leafminer).

The compounds of the present invention also have commercially significant activity against members of the order Homoptera, including: Acyrthosiphon pisum Harris (pea aphid), cowpea aphid ( Aphis craccivora Koch, cowpea aphid), black bean aphid ( Aphis fabae Scopoli, black bean aphid), cotton aphid ( Aphis gossypii Glover, cotton aphid, melon aphid), apple aphid ( Aphis pomi De Geer, apple aphid), rust spiral aphid ( Aphis spiraecola Patch, spirea aphid), potato aphid ( Aulacorthum solani Kaltenbach, foxglove aphid), strawberry aphid ( Chaetosiphon fragaefolii Cockerell, strawberry aphid), Russian wheat aphid ( Diuraphis noxia Kurdjumov/Mordvilko, Russian wheat aphid), rose apple aphid ( Dysaphis plantaginea Paaserini, rosy apple aphid), apple aphid ( Eriosoma lanigerum Hausmann, woolly apple aphid), peach aphid ( Hyalopterus pruni Geoffroy, mealy plum aphid), turnip aphid ( Lipaphis erysimi Kaltenbach, turnip aphid), wheat aphid ( Metopolophium dirrhodum Walker, cereal aphid), Macrosiphum euphorbiae Thomas, potato aphid, Myzus persicae Sulzer, peach-potato aphid, green peach aphid, Nasonovia ribisnigri Mosley, lettuce aphid, Pemphigus spp. ) (root aphid and gall aphid), corn leaf aphid ( Rhopalosiphum maidis Fitch , corn leaf aphid), grain aphid ( Rhopalosiphum padi Linnaeus, bird cherry-oat aphid), wheat aphid ( Schizaphis graminum Rondani, greenbug), wheat long tube aphid ( Sitobion avenae Fabricius, English grain aphid), alfalfa Spotted aphid ( Therioaphis maculate Buckton, spotted alfalfa aphid), orange aphid ( Toxoptera aurantii Boyer de Fonscolombe, black citrus aphid ) and brown citrus aphid ( Toxoptera citricida Kirkaldy, brown citrus aphid); Adelges spp. (Adelgid); American hickory phylloxera ( Phylloxera devastatrix Pergande, pecan phylloxera) ; ), citrus whitefly ( Dialeurodes citri Ashmead, citrus whitefly) and greenhouse whitefly ( Trialeurodes vaporariorum Westwood, greenhouse whitefly); potato leafhopper ( Empoasca fabae Harris, potato leafhopper), small brown planthopper ( Laodelphax striatellus Fallen, small brown planthopper ), purple leafhopper ( Macrolestes quadrilineatus Forbes, aster leafhopper), green leafhopper ( Nephotettix cinticeps Uhler, green leafhopper), rice leafhopper ( Nephotettix nigropictus Stal, rice leafhopper), brown planthopper ( Nilaparvata lu gens Stal, brown planthopper), corn planthopper ( Peregrinus maidis Ashmead, corn planthopper), white-backed planthopper ( Sogatella furcifera Horvath, white-backed planthopper), rice planthopper ( Sogatodes orizicola Muir, rice delphacid), apple leafhopper ( Typhlocyba pomaria McAfee, white apple leafhopper), Erythroneoura spp. (grape leafhopper); Periodic cicada ( Magicidada septendecim Linnaeus, periodic cicada); Icerya purchase Maskell, cottony cushion scale ), Quadraspidiotus perniciosus Comstock (San Jose scale); Citrus mealybug ( Planococcus citri Risso, citrus mealybug); Pseudococcus spp. (Other mealybug complexes); Pear psylla ( Cacopsylla pyricola Foerster, pear psylla), persimmon psylla ( Trioza diospyri Ashmead, persimmon psylla).

The compounds of the present invention may also be active against members of the order Hemiptera, including: Acrosternum hilare Say, green stink bug, Amrasca biguttulla biguttulla , cotton jassid, squash bug ( Anasa tristis De Geer, squash bug), wheat bug ( Blissus leucopterus leucopterus Say, chinch bug), bed bug ( Cimex lectularius Linnaeus , bed bug), cotton net bug ( Corythuca gossypii Fabricius , cotton lace bug), potato bug ( Cyrtopeltis modesta Distant, tomato bug), cotton stink bug ( Dysdercus suturellus Herrich-Schffer, cotton stainer), brown stink bug ( Euchistus servus Say, brown stink bug), one-spotted stink bug ( Euchistus variolarius Palisotde Beauvois, one-spotted stink bug), Graptόsthetus spp. (complex of broad shield bug), Leptoglossus corculus Say, leaf-footed pine seed bug, Lygus lineolaris Palisot de Beauvois, tarnished plant bug ), rice green bug ( Nezara viridula Linnaeus, southern green stink bug), rice bug ( Oebalus pugnax Fabricius, rice stink bug), large milkweed plant bug ( Oncopeltus fasciatus Dallas, large milkweed bug), cotton jumping bug ( Pseudatomoscelis seriatus Reuter, cotton fleahopper).

Other insect orders controlled by the compounds of formula (I) of the present invention include: Thysanoptera (for example, Western flower thrips ( Frankliniella occidentalis Pergande, western flower thrips), citrus thrips ( Scirthothrήps citri Moulton, citrus thrips), soybean thrips ( Sericothrips variabilis Beach, soybean thrips), small yellow thrips ( Scirtothrips dorsalis , chilli thrips or yellow tea thrips) and onion thrips ( Thrips tabaci Lindeman, onion thrips)); and Coleoptera (for example, potato beetle ( Leptinotarsa decemlineata Say , Colorado potato beetle), Mexican bean beetle ( Epilachna varivestis Mulsant, Mexican bean beetle) and nematodes of the genus Agriotes, Athous or Limonius).

In particular, the compounds of formula (I), their N-oxides, their isomers, their allomorphs and their salts are particularly suitable for effective combating of pests derived from insects of the order Lepidoptera, e.g. Tiger ( Agrotis ypsilon ), yellow cutworm ( Agrotis segetum ), cottonleaf moth ( Alabama argillacea ), bean moth ( Anticarsia gemmatalis ), apple nest moth ( Argyresthia conjugella ), owl moth ( Autographa gamma ), pine moth Inchworm ( Bupalus piniarius ), Cacoecia murinana , Cotton brown-banded tortrix ( Capua reticulana ), inchworm ( Cheimatobia brumata ), spruce leaf tortrix ( Choristoneura fumiferana ), western spruce aphid ( Choristoneura occidentalis ), American armyworm ( Cirphis unipuncta ), codling moth ( Cydia pomonella ), European pine caterpillar ( Dendrolimus pini ), melon borer ( Diaphania nitidalis ), giant corn borer ( Diatraea grandiosella ), cotton moth ( Earias insulana ), Square cotton bollworm ( Earias vittella ), lesser corn borer ( Elasmopalpus lignosellus ), grape moth ( Eupoecilia ambiguella ), European pine moth ( Evetria bouliana ), cutworm ( Feltia subterranea ), greater wax moth ( Galleria mellonella ), plum Small borer ( Grapholita funebrana ), pear borer ( Grapholita molesta ), tomato armyworm ( Helicoverpa armigera ), American tobacco armyworm ( Helicoverpa virescens ), cotton bollworm ( Helicoverpa zea ), cabbage borer ( Hellula undalis ), gray skirt looper moth ( Hibernia defoliaria ), American white moth ( Hyphantria cunea ), apple nest moth ( Hypono meuta malellus ), tomato beetle moth ( Keiferia lycopersicella ), hemlock looper moth ( Lambdina fiscellaria ), beet armyworm ( Laphygma exigua ), coffee leafminer ( Leucoptera coffeeella ), spinner leafminer ( Leucoptera scitella ), spotted leafminer Lithocolletis blancardella , Lobesia botrana , Loxostege sticticalis , Leucinodes orbonalis , Lymantria dispar , Lymantria monacha , Narrow-winged Leafminer ( Lyonetia clerkella ), Canopy Caterpillar ( Malacosoma neustria ), Cabbage Spodoptera ( Mamestra brassicae ), Douglas Fir Thymus ( Orgyia pseudotsugata ), European Corn Borer ( Ostrinia nubilalis ), Winter Spodoptera ( Panolis flammea ), red bell Pectinophora gossypiella , Variegated cutworm ( Peridroma saucia ), Phalera bucephala , Potato tuber moth ( Phthorimaea operculella ), Orange miner ( Phyllocnistis citrella ), Cabbage butterfly ( Pieris brassicae ), Clover green Noctuid moth ( Plathypena scabra ), diamondback moth ( Plutella xylostella ), soybean moth ( Pseudoplusia includesens ), pine leaf tortrix ( Rhyacionia frustrana ), tomato leaf miner ( Scrobipalpula absoluta ), wheat moth ( Sitotroga cerealella ), grape leaf tortrix ( Sparganothis pilleriana ), grass armyworm ( Spodoptera frugiperda ), gray winged moth ( Spodoptera littoralis ), litura litura ( Spodoptera litura ), Spodoptera exigua , Thaumatopoea pityocampa , Tortrix viridana , Trichoplusia ni , and Zeiraphera canadensis ; and beetles ( Coleoptera ) such as Agrilus sinuatus , Agriotes lineatus , Agriotes obscurus , Amphimallus solstitialis , Anisandrus dispar , boll weevil Anthonomus grandis , Apple Blossom Weevil ( Anthonomus pomorum ), Aphthona euphoridae , Red-tailed click beetle ( Athous haemorrhoidalis ), Atomaria linearis , Blastophagus piniperda , Blitophaga undata , broad bean weevil ( Bruchus rufimanus ), pea weevil ( Bruchus pisorum ), lentil weevil ( Bruchus lentis ), apple leaf curl weevil ( Byctiscus betulae ), beet giant tortoise beetle ( Cassida nebulosa ), bean leaf beetle ( Cerotoma trifurcata ), Cetonia aurata , Cabbage Pod Weevil ( Ceuthorrhynchus assimilis ), Stem Weevil ( Ceuthorrhynchus napi ), Beet Weevil ( Chaetocnema tibialis ), Tobacco Weevil ( Conoderus vespertinus ), Asparagus Crioceris asparagi , Ctenicera ssp. , Diabrotica longicornis , Diabrotica semipunctata , Diabrotica undecimpunctata , Brazilian leaf beetle ( Diabrotica speciosa ), Corn root leaf beetle ( Diabrotica virgifera ), Mexican bean beetle (Epilachna varivestis ), tobacco flea beetle ( Epitrix hirtipennis ), cotton borer ( Eutinobothrus brasiliensis ), pine weevil ( Hylobius abietis ), Egyptian clover weevil ( Hypera brunneipennis ), cloverleaf weevil ( Hypera postica ) , spruce beetle ( Ips typographus ), barbed mud beetle ( Lema bilineata ), black horned mud beetle ( Lema melanopus ), potato beetle ( Leptinotarsa decemlineata ), Beet Weevil ( Limonius californicus ), Rice Weevil ( Lissorhoptrus oryzophilus ), Cotton Nematode ( Melanotus communis ), Rapeseed Beetle ( Meligethes aeneus ), Melolontha hippocastani , Western Maybeetle ( Melolontha melolontha ), Oulema oryzae , Black vine weevil ( Ortiorrhynchus sulcatus ), Strawberry root weevil ( Otiorrhynchus ovatus ), Horseradish weevil ( Phaedon cochleariae ), Pear cut leaf weevil ( Phyllobius pyri ), rapeseed weevil Flea beetle ( Phyllotreta chrysocephala ), scarab ( Phyllophaga sp. ), garden beetle ( Phyllopertha horticola ), turnip beetle ( Phyllotreta nemorum ), yellow curly beetle ( Phyllotreta striolata ), Japanese beetle ( Popillia japonica ) , pea leaf weevil ( Sitona lineatus ) and grain elephant ( Sitophilus granaria ); flies, mosquitoes ( Diptera ) such as Aedes aegypti , Aedes albopictus , Aedes albopictus ( Aedes vexans ), Anastrepha ludens , Anopheles maculipennis , Anopheles crucians , Anopheles albimanus , Anopheles gambiae , Anopheles fischeri ( Anopheles freeborni ), Anopheles leucosphyrus , Anopheles minimus , Anopheles quadrimaculatus , red-headed blowfly ( Calliphora vicina ), Mediterranean fruit fly ( Ceratitis capitata ), gold maggot Chrysomya bezziana , Chrysomya hominivorax , Chrysomya macellaria , Chrysops discalis , Chrysops silacea , Chrysops atlanticus , sheepskin Cochliomyia hominivorax , Contarinia sorghicola , Cordylobia anthropophaga , Culicoides furens , Culex pipiens , Culex nigripalpus , Culex quinquefasciatus , Culex tarsalis , Culiseta inornata , Culiseta melanura , Dacus cucurbitae , Dacus oleae ), Brassica gall fly ( Dasineura brassicae ), onion fly ( Delia antique ), corn fly ( Delia coarctata ), gray field fly ( Delia platura ), cabbage fly ( Delia radicum ), human skin fly Fly ( Dermatobia hominis ), yellow-bellied fly ( Fan nia canicularis ), Geomyza Tripunctata , Gasterophilus intestinalis , Glossina morsitans , Glossina palpalis , Glossina fuscipes , Glossina tsetse ( 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 , Grass fly ( Opomyza florum ), Swedish straw fly ( Oscinella frit ), sugar beet leafminer ( Pegomya hysocyami ), onion fly ( Phorbia antiqua ), cabbage fly ( Phorbia brassicae ), wheat fly ( Phorbia coarctata ), silver-footed sandfly ( Phlebotomus argentipes ), Columbia scale mosquito ( Psorophora columbiae ), carrot stem fly ( Psila rosae ), heterochromatic scale mosquito ( Psorophora discolor ), mixed black mosquito ( Prosimulium mixtum ), cherry fruit fly ( Rhagoletis cerasi ), apple fruit fly ( Rhago letis pomonella ), red-tailed meat fly ( Sarcophaga haemorrhoidalis ), meat fly species ( Sarcophaga sp. ), gnat ( Simulium vittatum ), sting fly ( Stomoxys calcitrans ), gadfly ( Tabanus bovinus ), black fly ( Tabanus atratus ), Horse flies ( Tabanus lineola ), pseudo-barrel flies ( Tabanus similis ), common mosquitoes ( Tipula oleracea ) and European mosquitoes ( Tipula paludosa ); termites ( Isoptera ), such as the European carpenter termite ( Calotermes flavicollis ) ), common termites ( Leucotermes flavipes ), golden heterotermes ( Heterotermes aureus ), yellow-breasted termites ( Reticulitermes flavipes ), southern termites ( Reticulitermes virginicus ), southern European reticulite termites ( Reticulitermes lucifugus ), sandy termites ( Reticulitermes santonensis ), Reticulitermes grassei, Termes natalensis and Coptotermes formosanus ; cockroaches ( Blattaria Blattodea ), such as German cockroach ( Blattella germanica ), Asian cockroach ( Blattella asahinae ), Periplaneta americana , Periplaneta japonica , Periplaneta brunnea , Periplaneta fuligginosa , Periplaneta australasiae , and Blatta orientalis ); ants, bees, wasps, sawflies ( Hymenoptera ), e.g. Athalia rosae, Atta cephalotes, Atta ca piguara ), tropical leafcutter ants ( Atta cephalotes ), bright leafcutter ants ( Atta laevigata ), strong leafcutter ants ( Atta robusta ), South American leafcutter ants ( Atta sexdens ), Texas leafcutter ants ( Atta texana ), tail lifters Crematogaster spp. , Hoplocampa minuta , Hoplocampa testudinea , Lasius niger , Monomorium pharaonis , Solenopsis geminata ), Red Fire Ant ( Solenopsis invicta ), Black Fire Ant ( Solenopsis richteri ), California Fire Ant ( Solenopsis xyloni ), Red Harvester Ant ( Pogonomyrmex barbatus ), California Harvester Ant ( Pogonomyrmex californicus ), Bighead Ant ( Pheidole megacephala ), Western Ant Bee ( Dasymutilla occidentalis ), Bombus spp. , Vespula squamosa , common wasp ( Paravespula vulgaris ), tree wasp ( Paravespula pennsylvanica ), German wasp ( Paravespula germanica ), white-faced wasp ( Dolichovespula maculata ), yellow-fronted wasp ( Vespa crabro ), ocher wasp ( Polistes rubiginosa ), Florida ants ( Camponotus floridanus ) and Argentine ants ( Linepithema humile ); crickets, grasshoppers, locusts ( Orthoptera ), Examples include house cricket ( Acheta domestica ), European mole cricket ( Gryllotalpa gryllotalpa ), migratory locust ( Locusta migratoria ), double-banded grasshopper ( Melanoplus bivittatus ), red-legged grasshopper ( Melanoplus femur-rubrum ), Mexican grasshopper ( Melanoplus me xicanus ), migratory grasshopper ( Melanoplus sanguinipes ), rocky mountain grasshopper ( Melanoplus spretus ), red-winged grasshopper ( Nomadacris septemfasciata ), American grasshopper ( Schistocerca americana ), desert locust ( Schistocerca gregaria ), Moroccan grasshopper ( Dociostaurus maroccanus ), greenhouse Cricket ( Tachycines aynamorus ), Senegalese grasshopper ( Oedaleus senegalensis ), stinky locust ( Zonozerus variegatus ), spotted horned locust ( Hieroglyphus daganensis ), Indian yellow sandalwood locust ( Kraussaria angulifera ), Italian locust ( Calliptamus italicus ), Australian plague locust Grasshoppers ( Chortoicetes terminifera ) and South African locusts ( Locustana pardalina ); Araneid a , such as black widow spiders ( Latrodectus mactans ) and brown recluse spiders ( Loxosceles reclusa ); fleas ( Siphonaptera ), such as cat combs Ctenocephalides felis , Ctenocephalides canis , Xenopsylla cheopis , Pulex irritans , Tunga penetrans , and Nosopsyllus fasciatus ; silverfish and housefish ( firebrat ); centipedes ( Chilopoda ), e.g. Scutigera oleoptrata ; millipedes ( Diplopoda ), e.g. Narceus spp. ; earwigs (earwig ) ( Dermaptera ) such as forficula auricularia; lice ( Phthiraptera ) such as Pediculus humanus capitis , Pediculus humanus corporis ), Pthirus pubis , cattle lice ( Haematopinus eurysternus ), pig lice ( Haematopinus suis ), bovine jaw lice ( Linognathus vituli ), cattle bird lice ( Bovicola bovis ), chicken lice ( Menopon allinae ), large Chicken lice ( Menacanthus stramineus ) and small short-nosed cow lice ( Solenopotes capillatus ); from the order of the Collembola ( springtails ), e.g. Onychiurus ssp.

The compound of formula (I) of the present invention is suitable for controlling nematodes: plant parasitic nematodes, such as root knot nematodes ( root knot nematodes ), northern root knot nematodes ( Meloidogyne hapla ), southern root knot nematodes ( Meloidogyne incognita ), Javan root knot nematodes Meloidogyne javanica and other Meloidogyne species; cyst-forming nematodes , Globodera rostochiensis and other Globodera species; wheat cyst nematodes ( Heterodera avenae ), soybean cyst nematode ( Heterodera glycines ), sugar beet cyst nematode ( Heterodera schachtii ), clover cyst nematode ( Heterodera trifolii ) and other cyst nematode ( Heterodera ) species; seed gall nematodes ( Seed gall nematodes ), grain Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species 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 and other Ditylenchus species ( Ditylenchus ) species; Trypanosoma ( Awl nematodes ), Trypanosoma ( Dolichodorus ) species; Spiral nematodes ( Spiral nematodes ), Helicotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes , Hemiccliophora species and Hemicriconemoides species; rice root nematodes Hirshmanniella species; Lance nematodes , Hoploaimus species; false rootknot nematodes , Nacobbus species; Needle nematodes ), Longidorus elongatus and other Longidorus species; Lesion nematodes , Pratylenchus neglectus , Pratylenchus penetrans , curved root rot Nematodes ( Pratylenchus curvitatus ), Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Kidney Reniform nematodes, Rotylenchus robustus and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Stubby root nematodes ( Trichodorus primitivus ) and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni , Tylenchorhynchus dubius and other dwarf nematode genera ( Tylencho rhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species.

The compound of formula (I) of the present invention is also effective for controlling arachnids ( arachnids ) (Arachnoidea ( Arachnoidea )), such as the order Acarina ( Acarina ), for example, Argasidae ( Argasidae ), ticks ( Ixodidae ) and Sarcoptidae , such as Amblyomma americanum , Amblyomma variegatum, Argas persicus , Boophilus annulatus , Boophilus decoloratus , Boophilus microplus , Dermacentor silvarum , Hyalomma truncatum , Ixodes ricinus , Ixodes rubicundus , Ornithodorus moubata , Otobius megnini , Dermanyssus gallinae , Psoroptes ovis , Rhipicephalus appendiculatus , Rhipicephalus evertsi , Sarcoptes scabiei and Eriophyidae spp. , such as Aculus schlechtendali , Phyllocoptrata oleivora, and Eriophyes sheldoni ; Tarsonemidae spp. , such as fairy Phytonemus pallidus and Polyphagotarsonemus latus ; Tenuipalpidae spp. , such as Brevipalpus phoenicis; Tetranychidae spp. , such as cinnabar leaf Mite ( Tetranychus cinnabarinus ), Tetranychus kanzawai , Pacific red spider mite ( Tetra nychus pacificus ), cotton spider mite ( Tetranychus telarius ) and cotton spider mite ( Tetranychus urticae ), apple spider mite ( Panonychus ulmi ), orange spider mite ( Panonychus citri ) and grass mite ( oligonychus pratensis ).

In one embodiment of the present invention, the present invention provides a compound of formula (I), which is useful for controlling insects selected from the group consisting of sucking or piercing insects, for example from the orders Thysanoptera, Diptera and Hemiptera. Insects of the order Hemiptera, especially the following species: Thysanoptera: tobacco brown thrips ( Frankliniella fusca ), alfalfa thrips ( Frankliniella occidentalis ), flower thrips ( Frankliniella tritici ), orange thrips ( Scirtothrips citri ), Scirtothrips dorsalis , Thrips oryzae , Thrips palmi , and Thrips tabaci ; Diptera: Aedes aegypti ), Aedes albopictus , Aedes vexans , Anastrepha ludens , Anopheles maculipennis , Anopheles crucians , Anopheles pauci ( Anopheles albimanus ), Anopheles gambiae ( Anopheles gambiae ), Anopheles freeborni , Anopheles leucosphyrus , Anopheles minimus , Anopheles quadrimaculatus , Anopheles quadrimaculatus Ceratitis capitata , Chrysomya bezziana , Chrysomya hominivorax , Chrysomya macellaria , Chrysomya macellaria , Chrysops discalis , yellow ocher stain Chrysops silacea , Chrysops atlanticus , Cochliomyia hominivorax , Contarinia sorghicola , C. ordylobia anthropophaga ), Culicoides furens , Culex pipiens , Culex nigripalpus , Culex quinquefasciatus , Culex tarsalis , Culex tarsalis Culiseta inornata , Culiseta melanura , Dacus cucurbitae , Dacus oleae , Dasineura brassicae , Delia antique ), Delia coarctata , Delia platura , Delia radicum , Dermatobia hominis , Fannia canicularis , Three-spotted grass fly ( Geomyza Tripunctata ), Gasterophilus intestinalis , Glossina morsitans , Glossina palpalis , Glossina fuscipes , Glossina tachinoides , Horn fly ( 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 , Hessian straw fly ( Mayetiola destructor ), Qiujia Musca autumnalis , Musca domestica , Muscina stabulans , Oestrus ovis , Opomyza florum , Oscinella frit , Beet leafminer ( Pegomya hysocyami ), onion fly ( Phorbia antiqua ), cabbage fly ( Phorbia brassicae ), wheat fly ( Phorbia coarctata ), silver-footed sandfly ( Phlebotomus argentipes ), Columbia scaled mosquito ( Psorophora columbiae ), carrot stalk fly ( Psila rosae ), Psorophora discolor , Prosimulium mixtum , Rhagoletis cerasi , Rhagoletis pomonella , Sarcophaga haemorrhoidalis , Sarcophaga spp . Gnats ( Simulium vittatum ), gnat flies ( Stomoxys calcitrans ), gadflies ( Tabanus bovinus ), black flies ( Tabanus atratus ), barbed horseflies ( Tabanus lineola ), sting flies ( Tabanus similis ), common gnats ( Tipula oleracea ) and European mosquito ( Tipula paludosa ); Hemiptera (Hemiptera), especially aphids ( aphids ): donkey bean aphid ( Acyrthosiphon onobrychis ), larch ball aphid ( Adelges laricis ), watercress aphid ( Aphidula nasturtii ), broad bean aphid ( Aphis fabae ), Aphis forbesi , apple aphid ( Aphis pomi ), cotton aphid ( Aphis gossypii ), gooseberry aphid ( Aphis grossulariae ), schneideri ( Aphis schneideri ), spirea aphid ( Aphis spiraecola ) , Aphis sambuc i ), pea aphid ( Acyrthosiphon pisum ), potato aphid ( Aulacorthum solani ), thistle aphid ( Brachycaudus cardui ), round-tailed aphid ( Brachycaudus helichrysi ), peach black aphid ( Brachycaudus persicae ), plum aphid ( Brachycaudus prunicola ), Brevicoryne brassicae , Capitophorus horni , Cerosipha gossypii , Chaetosiphon fragaefolii , Cryptomyzus ribis , Normany Dreyfusia nordmannianae , Dreyfusia piceae , Dysaphis radicola , Dysaulacorthum pseudosolani , Dysaphis plantaginea , Dysaphis pyri , Vicia faba Leafhopper ( Empoasca fabae ), plum aphid ( Hyalopterus pruni ), tea currant aphid ( Hyperomyzus lactucae ), wheat aphid ( Macrosiphum avenae ), euphorbia aphid ( Macrosiphum euphorbiae ), rose aphid ( Macrosiphon rosae ), Megoura viciae , Melanaphis pyrarius , Metopolophium dirhodum , Myzodes persicae , Myzus ascalonicus , Myzus ascalonicus cerasi ), Myzus variants , Nasonovia ribis-nigri , Nilaparvata lugens , Pemphigus bursarius , Perkinsiella saccharicida , hops Aphids ( Phorodon humuli ), Psylla mali , Psylla piri , Rhopalomyzus ascalonicus , Rhopalosiphum maidis , Rhopalosiphum padi , applegrass Rhopalosiphum insertum , Sappaphis mala , Sappaphis mali , Schizaphis graminum , Schizoneura lanuginosa , Sitobion avenae ), greenhouse whitefly ( Trialeurodes vaporariorum ), large orange aphid ( Toxoptera aurantiiiand ) and grape phylloxera ( Viteus vitifolii ).

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

Known and reported fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics and nutrients can be combined with at least one compound of formula (I) according to the invention . For example, fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, Fertilizers and nutrients may be combined with at least one compound of formula (I) according to the invention.

Fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients reported in PCT Patent Publication No. WO2016156129 and/or PCT Patent Publication No. WO2017153200 The references are incorporated herein as non-limiting examples to be combined with at least one compound of formula (I) according to the invention.

In particular, the compounds of the present invention may be mixed with at least one additional biologically active compatible compound (mixing pair), including but not limited to insecticides, fungicides, nematocides, bactericides, acaricides, growth regulators (e.g. rooting stimulants, chemical fungicides, semiochemicals, repellents, attractants, pheromones, feeding stimulants, other biologically active compounds) or entomopathogenic bacteria, viruses or fungi, and Form a multi-component pesticide that provides a wider range of agricultural uses.

Examples of such biologically active compounds or agents/mixture pairs with which the compound of formula (I) of the present invention can be combined/formulated are disclosed in PCT Patent Publication No. WO2019072906A1 (pages 27 to 37).

In one embodiment, biological agents for use in admixture with the compounds of the invention include Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, and naturally occurring and genetically modified viral insecticides, It includes members of the family Baculoviridae as well as entomophagous fungi.

In some cases, resistance management will be especially beneficial in combination with other invertebrate pest control compounds, or agents with similar control spectrum but different modes of action. Accordingly, the compositions of the present invention may further comprise a biologically effective amount of at least one additional invertebrate pest control compound or agent having similar control properties but a different mode of action. Contacting plants or plant loci genetically modified to express plant protection compounds (eg proteins) with biologically effective amounts of compounds of the invention may also provide broader plant protection and facilitate resistance management.

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

The present invention also provides a method of controlling an invertebrate pest, the method comprising: causing the invertebrate pest, its habitat, breeding ground, food supply, plant, seed, soil, area, material, or the invertebrate pest to The environment in which it grows or may grow, or the material, plant, seed, soil, surface or space to be protected from pest attack or infestation, and a biologically effective amount of a compound of formula (I), its agronomically acceptable salt, iso Conformers/structural isomers, stereoisomers, diastereoisomers, enantiomers, tautomers, metal complexes, isomers, or N-oxide compositions or combinations thereof.

Invertebrate pest control and protection of agronomic, horticultural and specialty crops, animal and human health by applying an effective amount of one or more compounds of the present invention to the pest environment (including agronomic and/or non-agronomic crop infestation ), applied to the area to be protected, or applied directly to the pests to be controlled. Accordingly, the present invention further includes methods of controlling foliar and soil invertebrates and protecting agronomic and/or nonagronomic crops, the method comprising subjecting the invertebrates or their environment to a biologically effective amount of one or more of these species. The compound of the invention is contacted, or with a composition comprising at least one such compound, or comprising at least one such compound and an effective amount of at least one additional biologically active compound or agent. A preferred method of contact is by spraying. Alternatively, granular compositions comprising a compound of the invention may be applied to plant foliage or to the soil. Compounds of the invention may also be produced by contacting plants with a composition comprising a compound of the invention applied as a soil drench of a liquid formulation, a granular formulation applied to the soil, a nursery box treatment, or by dipping a transplant. Plant uptake for efficient delivery. Other methods of exposure include via direct and residual sprays, air sprays, gels, seed coatings, microencapsulation, systemic absorption, baits, ear tags, boluses, nebulizers, fumigants, aerosols, dusts, and many others or administer the compound or composition of the present invention.

The compounds of the present invention may be incorporated into baits that are consumed by invertebrate pests or used in devices such as traps, bait stations and the like. Granules or baits containing 0.01%-5% active ingredient, 0.05%-10% humectant, and 40%-99% vegetable powder, which can be used at very low application rates, especially by ingestion rather than by direct Effective control of soil insects at contact lethal doses of the active ingredient. The compounds of the invention may be used in their pure form, but most commonly they will be in formulations comprising one or more compounds together with suitable carriers, diluents and surfactants, and possibly in combination with foodstuffs depending on the intended end use. Preferred methods of application include spraying an aqueous dispersion of the compound or a refined oil solution. Combinations with spray oils, spray oil concentrates, spreaders, adhesives, adjuvants, other solvents and synergists such as piperonylbutoxide often enhance compound efficacy.

The rate of application required for effective control (i.e. "biologically effective amount") should be considered as the species of invertebrate to be controlled, the life cycle of the pest, its life stage, its size, location, season, Depending on such factors as the subject crop or animal, feeding behaviour, mating behaviour, ambient humidity, temperature and the like. Under normal circumstances, an application rate of about 0.01 kg to 2 kg of active ingredient per hectare is sufficient to control pests in agroecosystems, but as little as 0.0001 kg per hectare may be sufficient or as much as 8 kg per hectare may be required of. For non-agronomic applications, effective application rates should be in the range of about 1.0 mg/m2 to 50 mg/m2, but as little as 0.1 mg/m2 may be sufficient or as much as 150 mg/m2 Meters may be required. One of ordinary skill in the art can readily determine the biologically effective amount required for the desired degree of invertebrate pest control.

Animal pests (i.e. arthropods, gastropods and nematodes), plants, the soil or water in which the plants grow can be passed through any application mode known in the technical field of this case and the compound of formula (I), its N-oxide And salt, or the composition contacting that comprises formula (I) compound, its N-oxide and salt. The term "contact" as used herein includes direct contact (application of the compound/composition directly to the animal pest or plant, usually to the leaves, stems or roots of the plant) and indirect contact (application of the compound/composition to the animal pest or plant location).

The compound of the present invention or the pesticidal composition comprising said compound can be used to protect growing plants/crops from animal pests (especially Insecta, Acaridae or Arachnida) attack or infection. The term "crop" refers to both growing and harvested crops.

In one embodiment, the present invention provides a method of protecting crops from attack or infestation by invertebrate pests, the method comprising: reacting the crops with a biologically effective amount, an isomer, of a compound or composition of the present invention , allomorphs, N-oxides or combinations thereof.

The compounds of the present invention, per se or in the form of compositions, can be obtained by applying an insecticidally effective amount of the active compound to insects or plants, plant propagation material (such as seeds, soil, surfaces, materials or objects protected from insecticidal attack). space). The abovementioned applications can be carried out before and after the plants, plant propagation material (eg seeds, soil, surface, material or space) have been infested by insects.

In one embodiment, the present invention provides a method for protecting seeds from soil insects and protecting seedling roots and shoots from soil and foliar insects, the method comprising: prior to sowing and/or germination, exposing the seeds to The compound or composition of the present invention, its N-oxide or salt is contacted.

Furthermore, the present invention provides a method for treating or protecting animals from infestation or infection by parasites, the method comprising: administering a biologically effective amount of the compound or composition of the present invention, its isomers, isomorphs , N-oxide or biologically acceptable salt, administered orally, topically or parenterally to the animal.

For the treatment of agricultural crops, the application rate (application effective dose) of the compound of the present invention may be in the range of 1 gram of active ingredient (gai) to 5000 grams of active ingredient (gai) per hectare in agricultural or horticultural crops, preferably 1 gram per hectare. 25 grams to 600 grams per hectare, more preferably 50 grams to 500 grams per hectare.

The compounds and compositions of the present invention are especially suitable for controlling a large number of insects on various cultivated plants such as cereals, root crops, oil crops, vegetables, spices, ornamentals such as durum and other wheat seeds, barley , oats, rye, corn (feed corn and sugar corn/sweet corn and common corn), soybeans, oil crops, cruciferous plants, cotton, sunflowers, bananas, rice, canola, radish canola, sugar beet, fodder beet, eggplant , potatoes, grasses, lawns, turf, forage grasses, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, peppers, cucumbers, melons, Brassica species, melons, Beans, peas, garlic, onions, carrots, tubers such as potatoes, sugar cane, tobacco, grapes, petunia, geranium/pelargoniums, pansies and impatiens.

In particular, the compounds or compositions of the present invention can be used to protect crops such as cereals, corn, rice, soybeans and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbits family, oleaginous plants, tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton, potato, tomato, onion, pepper and other vegetables and ornamental plants.

The compounds of the present invention are effective both through contact (through soil, glass, walls, mosquito nets, carpets, plant parts or animal parts) and ingestion (baits or plant parts).

The compounds of the present invention are also useful against non-crop invertebrate pests such as ants, termites, wasps, flies, mosquitoes, crickets or cockroaches. For use against said non-crop pests, the compounds of the invention are preferably used in bait compositions.

Baits can be liquid, solid or semi-solid formulations (eg gels). Solid baits can be formed into various shapes and forms suitable for individual application, such as granules, blocks, sticks, discs. Liquid baits can be filled in various devices such as open containers, sprinklers, droplet sources or evaporation sources to ensure proper application. Gels can be based on aqueous or oily bases and can be formulated to specific needs in terms of viscosity, water retention or aging characteristics.

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 the bait. Attraction can be manipulated by the use of feeding stimulants or sex pheromones. Food stimulants are selected from, for example (but not limited to) animal and/or vegetable proteins (meat meal, fish meal or blood meal, insect parts, egg yolk), fats and oils from animal and/or vegetable origin, or mono-organic sugars, Oligo- or polyorganic sugars, especially selected from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decayed parts of fruits, crops, plants, animals, insects or specific parts thereof may also be used as feeding stimulants. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and known to those skilled in the art.

When used in bait compositions, the typical content of the active ingredient is 0.001% to 15% by weight, ideally 0.001% to 5% by weight of active compound.

Formulations of the compounds of the invention in the form of aerosols (e.g. in spray cans), oil sprays or pump sprays are highly suitable for non-professional users for controlling insects such as flies, fleas, ticks, mosquitos or cockroaches. pests. The aerosol formulation is preferably composed of the following: active compound; solvent, such as low carbon alcohol (such as methanol, ethanol, propanol, butanol), ketone (such as acetone, methyl ethyl ketone), with a temperature of about 50 ° C to 250 Paraffin hydrocarbons (such as kerosene), dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, aromatic hydrocarbons (such as toluene, xylene), water in the boiling point range of ℃; in addition, additives, Such as emulsifiers, such as sorbitan monooleate, oleyl ethoxylates with 3 to 7 moles of ethylene oxide, fatty alcohol ethoxylates, perfume oils (such as essential oils), medium-carbon fatty acids Esters with lower alcohols, aromatic carbonyl compounds; where appropriate, stabilizers (such as sodium benzoate), amphoteric surfactants, lower carbon epoxides, triethyl orthoformate; and when necessary, propellants such as propane , butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide or a mixture of these gases.

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

The compounds of the present invention and their respective compositions can also be used in mosquito coils and fumigation coils, chimneys, evaporator panels or long-term evaporators as well as moth papers, moth mats or other heat-independent evaporator systems.

The method of controlling infectious diseases transmitted by insects (such as malaria, dengue and yellow fever, lymphatic filariasis and leishmaniasis) with compounds of formula (I) and their respective compositions also includes treatment sheds Houses and housing surfaces, air spraying and impregnating curtains, tents, linen, mosquito nets, fly traps or the like. The insecticidal composition for application to fibres, fabrics, knits, nonwovens, netting materials or foils and tarpaulins preferably comprises a mixture comprising an insecticide, optionally a repellent and at least one binder . Suitable repellents are e.g. N,N-diethyl-m-toluamide (DEET), N,N-diethylphenylacetamide (DEPA), 1-(3-cyclohex-1-yl -Carbonyl)-2-methylpiperazine, (2-hydroxymethylcyclohexyl)acetolactone, 2-ethyl-1,3-hexanediol, indalone, methyl neodecylamide (MNDA), pyrethroids not used for insect control (such as {(+/-)-3-allyl-2-methyl-4-oxocyclopenta-2-(+) -alkenyl-(+)-trans-chrysanthemum ester (Esbiothrin)), plant-derived or equivalent repellants (e.g. limonene, eugenol, (+)-eucamalol (1) , (-)-1-epieucanol), or repellants derived from crude plant extracts of plants (such as lemon amine (Eucalyptus maculata), vitex rotundifolia, palmarosa (Cymbopogan martinii) , Lemongrass (Cymbopogan citratus), Citronella (Cymopogan nartdus)). Suitable binders are selected from, for example, polymers and copolymers of vinyl esters of aliphatic acids such as vinyl acetate and vinyl versatate, acrylates and methacrylates of alcohols such as acrylic acid butyl ester, 2-ethylhexyl ester and methyl acrylate), mono- and dienically unsaturated hydrocarbons (such as styrene) and aliphatic dienes (such as butadiene).

Impregnation of curtains and mosquito nets is generally carried out by dipping the fabric material in an emulsion or dispersion or spraying the emulsion or dispersion onto the net.

The compounds and mixtures of the present invention and their compositions can be used for the protection of wooden materials such as trees, wooden fences, sleepers, frames, works of art, etc. and buildings, and also for the protection of construction materials, furniture, leather, fibers, vinyl products , wires and cables, etc. from ants and/or termites, and to control ants and termites that cause damage to crops or humans (such as when pests invade houses and public facilities). The compounds of the present invention are not only applied to the surrounding soil surface or subfloor soil to protect wooden materials, but also to wood products (such as concrete surfaces under floors, niche posts, beams, plywood, furniture, etc.), wood products (such as particleboard , half board, etc.) and vinyl products (such as coated wires, vinyl sheets, thermal insulation materials (such as foamed styrene), etc.).

In the case of application against ants that harm crops or humans, the compound of the present invention is applied to crops or surrounding soil, or directly to ant nests and the like.

seed treatment

The invention further provides a seed comprising a compound of the invention, especially the seed in an amount of about 0.0001% to about 1% by weight of the seed before treatment.

The compounds according to the invention are also suitable for the treatment of seeds to protect the seeds from pests, especially soil-dwelling insects and acarid pests, and to protect the roots and shoots of the resulting plants from soil and foliar pests.

The compounds of the invention are especially useful for protecting the seeds from soil pests and the roots (white grubs, termites, nematodes) and shoots of the resulting plants from soil pests and foliar insects. It is preferred to protect the roots and shoots of the resulting plants. Even more preferred are the shoots of the resulting plants protected from piercing-sucking insects, most preferably from aphids, jassids, thrips and whiteflies.

Accordingly, the present invention includes a method of protecting seeds from insects, especially soil insects, and seedling roots and shoots of the seeds from insects, especially soil and foliar insects, comprising: Before sowing the seed and/or after the seed has pregerminated, the seed is contacted with a compound of the invention. Especially preferred is a method of protecting the roots and shoots of plants; more preferred is a method of protecting the shoots of plants from piercing and sucking insects; and most preferred is a method of protecting plants The buds are protected from aphid attack.

The term "seed" covers all kinds of seeds and plant propagules, including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruits, tubers, grains, cuttings, cuttings and the like, and In a preferred embodiment it means real seeds.

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

The invention also includes seeds coated with or containing active compounds. Such seeds may be coated with a seed coating composition comprising a compound of the present invention. For example, the seed coating composition is reported in European Patent No. EP3165092, European Patent No. EP3158864, PCT Patent Publication No. WO2016198644, PCT Patent Publication No. WO2016039623, PCT Patent Publication No. WO2015192923, Canadian Patent No. Patent Publication No. US2004237395, PCT Patent Publication No. WO2011028115, European Patent No. EP2229808, PCT Patent Publication No. WO2007067042, European Patent No. EP1795071, European Patent No. EP1273219, PCT Patent Publication No. WO200178507, European Patent No. EP1247436, Dutch Patent No. NL1012918 and Canadian Patent No. CA2083415.

The phrase "coated with and/or containing" generally means that the active ingredient is mostly on the surface of the propagation product at the time of application, although a greater or lesser portion of the ingredient may penetrate into the propagation product, depending on the method of application. When the propagation product is (re)planted, it absorbs the active ingredient.

Suitable seeds are, for example, seeds of cereals, root crops, oil crops, vegetables, spices, ornamental plants, such as durum wheat and other wheat, barley, oats, rye, corn (fodder corn and sugar corn/sweet corn and common corn) ), soybeans, oil plants, cruciferous plants, cotton, sunflower, banana, rice, rapeseed, turnip rape, sugar beet, fodder beet, eggplant, potato, grass, lawn, turf, fodder grass, tomato, leek, pumpkin/ Pumpkins, kale, iceberg lettuce, peppers, cucumbers, melons, Brassicas, melons, beans, peas, garlic, onions, carrots, tubers such as potatoes, sugar cane, tobacco, grapes, petunias, geraniums/geraniums, Seeds of pansies and impatiens.

In addition, the compounds according to the invention can also be used for the treatment of seeds from plants which have been bred (including genetically engineered) to be tolerant to the action of herbicides or fungicides or insecticides.

For example, the compounds of the present invention can be used in the treatment of seeds from plants for herbicidal activity selected from the group consisting of sulfonylureas, imidazolinones, glufosinate-ammonium or glyphosate-isopropylammonium and similar active substances. (See e.g. European Patent No. EP242236, European Patent No. EP242246) (PCT Patent Publication No. WO92/00377) (US Patent No. EP257993, U.S. Patent Publication No. US5013659), or in genetically modified crop plants (e.g. cotton ), which have the ability to produce Bacillus thuringiensis toxin (Bt toxin) and make these plants resistant to certain pests (European Patent No. EP142924, European Patent No. EP193259).

Furthermore, the compounds according to the invention can be used for the treatment of seeds from plants which have modified properties compared to existing plants, which can be produced, for example, by conventional breeding methods and/or by producing mutants, or by recombinant procedures. For example, many cases have been described for the purpose of modifying starch synthesized in plants (e.g. PCT Patent Publication No. WO92/11376, PCT Patent Publication No. WO92/14827, PCT Patent Publication No. Recombinant modification of crop plants for the purpose of breeding crop plants (PCT Patent Publication No. WO91/13972).

Seed treatment application of the compounds according to the invention is carried out by spraying or sowing the plants before sowing and before emergence of the plants.

Compositions particularly suitable for seed treatment are, for example: Water Soluble Concentrates (SL, LS) Emulsions (EW, EO, ES) Suspensions (SC, OD, FS) Water Dispersible Granules and Water Soluble Granules (WG, SG) Water Dispersible Powder and Water Soluble Powder (WP, SP, WS) Gels (GW, GF) Pulverizable powders (DP, DS)

Conventional seed treatment formulations include, for example, flowable concentrates (FS), solutions (LS), powders (DS) for dry treatments, water-dispersible powders (WS) for slurry treatments, water-soluble powders (SS) ) and emulsions (ES and EC) and gel formulations (GF). These formulations can be applied to the seed diluted or undiluted. It can be applied directly to the seeds before sowing, or after they have germinated.

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

Other preferred FS formulations of the compounds of the invention for seed treatment 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 Surfactants, such as 0.05 to 5% by weight of wetting agents and 0.5 to 15% by weight of dispersants, up to 5 to 20% by weight (such as 5 to 20% by weight) of antifreeze agents, 1 to 15% by weight (such as 1 to 20% by weight) 15% by weight) of pigments and/or dyes, 0 to 40% by weight (eg 1 to 40% by weight) of binders (adhesives/adhesives), optionally up to 5% by weight (eg 0.1 to 5% by weight) Thickeners, optionally 0.1 to 2% by weight of defoamers and optionally preservatives (such as biocides, antioxidants, etc., for example, in an amount of 0.01 to 1% by weight) and up to 100% by weight of fillers /carrier.

Seed treatment formulations may additionally contain binders and, optionally, colorants.

Binders may be added to improve the adhesion of the treated active material to the seed. Suitable binders are homopolymers and copolymers from alkylene oxides such as ethylene oxide or propylene oxide, polyvinyl acetate, polyvinyl alcohol, polyvinylpyrrolidone and its copolymers, ethylene-vinyl acetate Copolymers, homopolymers and copolymers of acrylic acid, polyvinylamine, polyvinylamide and polyvinylpyrimidine, polysaccharides (such as cellulose, cellulose and starch), homopolymers and copolymers of polyolefins (such as olefin/ Homopolymers and copolymers of maleic anhydride copolymers, polyurethanes, polyesters, polystyrene).

Optionally, coloring agents can also be included in the formulation. Colorants or dyes suitable for seed treatment formulations are Rhodamine B, C.I. Pigment Red 1 12, C.I. Solvent Red 1, Pigment Blue 15:4, Pigment Blue 15:3, Pigment Blue 15:2, Pigment Blue 15:1, Pigment Blue 80, Pigment Yellow 1, Pigment Yellow 13, Pigment Red 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.

An example of a gelling agent is carrageenan ( ^Satiagel® ).

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, especially It is 1 gram to 200 grams per 100 kilograms of seeds. Accordingly, the present invention also provides seed comprising a compound of formula (I) or an agriculturally acceptable salt of formula (I) as defined herein. The amount of the compound of formula (I) or its agriculturally acceptable salt is usually 0.1 g to 10 kg per 100 kg of seeds, preferably 1 g to 5 kg per 100 kg of seeds, especially 1 g to 1000 g per 100 kg of seeds .

digital technology

The compounds of the invention can be used in combination with models, such as embedded in computer programs, for site-specific crop management, satellite farming, precision farming or precision agriculture. Such models support data from various sources (e.g. soil, weather, crops (e.g. variety, growth stage, plant health), weeds (e.g. variety, growth stage), disease, pests, nutrients, water, humidity, biomass, satellite data , production, etc.) in order to optimize profitability, sustainability and environmental protection. In particular, such models help to optimize agronomic decisions, control the precision of pesticide application and document the work done.

For example, if a model simulates pest development and calculates that a threshold for recommending application of a compound of the invention to a crop has been reached, the compound of the invention can be applied to the crop according to an appropriate dosage regimen.

Commercially available systems that include agronomic models are, for example, FieldScripts ^™ from The Climate Corporation, Xarvio ^™ from BASF, AGLogic ^™ from John Deere, and the like.

The compounds of the present invention can also be used in combination with intelligent spraying equipment, such as spot spraying attached to or mounted on agricultural vehicles (such as tractors, robots, helicopters, aircraft, unmanned aerial vehicles (UAVs, such as drones, etc.) ) or precision spraying equipment. Such devices typically include an input sensor (such as a camera) and a processing unit configured to analyze the input data and to provide a decision based on the analysis of the input data to treat the compound of the invention in a specific and precise manner. Applied to crops (respectively weeds) in the same way. The use of such smart spraying equipment usually also requires a positioning system (such as a GPS receiver) to locate the recorded data and guide or control agricultural vehicles; it also requires geographic information systems (GIS) to represent information on an understandable map , and appropriate agricultural vehicles are also required to perform the required agricultural actions (such as spraying).

In one example, pests can be detected from images taken by the camera. In one example, pests can be identified and/or classified based on the image. Such identification and/or classification may utilize image processing algorithms. Such image processing algorithms can utilize machine learning algorithms, such as trained neural networks, decision trees, and utilize artificial intelligence algorithms. In this way, the compounds described herein can be used only when needed.

animal health

The present invention also provides agricultural and/or veterinary compositions comprising at least one compound of formula (I).

In one embodiment, the present invention provides compounds of formula (I), agriculturally acceptable salts, isomers/structural isomers, stereoisomers, diastereomers, mirror isomers, tautomers The use of compounds, metal complexes, allomorphs or N-oxide compositions or combinations thereof for controlling invertebrate pests in crops and/or horticultural crops or parasites in animals.

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

It is therefore an object of the present invention to provide new methods of 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 animals, which can be applied through lower doses than those required by existing insecticides. Another object of the present invention is to provide insecticides for animals which provide long-term control of parasites.

The present invention also relates to a composition comprising at least one compound of formula (I), an N-oxide or a veterinarily acceptable salt thereof and an acceptable carrier in an effective amount for killing parasites, which is used for preventing and treating parasites in animals. Parasites on the body.

The present invention also provides a method for treating, controlling, preventing and protecting animals from parasitic infestation and infection, the method comprising orally, topically or parenterally administering or administering to the animal a parasiticidally effective amount of compounds or compositions containing such compounds.

The present invention also provides a process for the preparation of a composition for treating, controlling, preventing or protecting animals from parasitic infestation or infection, the composition comprising a parasiticidally effective amount of a compound of the present invention or a compound comprising the compound Composition.

The activity of compounds against agricultural pests does not indicate their suitability for controlling endoparasites and ectoparasites in and on animals, which requires, for example, low non-emetic doses (in the case of oral application), metabolic Compatibility, low toxicity and safe handling.

It has surprisingly been found that the compounds according to the invention are suitable for combating endoparasites and ectoparasites in and on animals.

The compounds of the present invention and compositions comprising the same are preferably used for the control and prevention of infestations and infections in animals including warm-blooded animals (including humans) and fish. It is suitable, for example, for the control and prevention of infestations and infections of mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, buffaloes , donkeys, yellow deer, and reindeer; and fur animals, such as mink, chinchilla, and raccoon; birds, such as chicken, geese, turkey, and duck; and fish, such as freshwater and saltwater fish, such as trout, carp, and eel.

The compounds of the present invention and compositions comprising the same are preferably used for the control and prevention of infestations and infections in domestic animals such as dogs or cats.

Infestations of warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nose worms, ticks, biting flies, moss flies, flies, myiasis larvae, chiggers, gnats, mosquitoes and fleas.

The compounds according to the invention and compositions comprising them are suitable for the systemic and/or non-systemic control of ectoparasites and/or endoparasites. It is active against all or part of the stages of development.

The compounds of the invention and compositions comprising them are especially useful for controlling ectoparasites.

The compounds of the present invention are especially useful against parasites of the following orders and species, respectively: fleas ( Siphonaptera ), such as Ctenocephalides felis , Ctenocephalides cams , Indian rats Fleas ( Xenopsylla cheopis ), human fleas ( Pulex irritans ), latent fleas ( Tunga penetrans ) and striped rat fleas ( Nosopsyllus fasciatus ), cockroaches ( Blattaria-Blattodea ), e.g. German cockroaches ( Blattella germanica ), Asian cockroaches ( Blattella asahinae ), American cockroaches ( Periplaneta americana ), Japanese cockroaches ( Periplaneta japonica ), brown cockroaches ( Periplaneta brunnea ), black-breasted cockroaches ( Peroplaneta fuligginosa ), Australian cockroaches ( Periplaneta australasiae ) and oriental cockroaches Cockroaches ( Blatta orientalis ), flies, mosquitoes (Diptera) such as 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 ), deer fly ( Chrysops discalis ), deer fly ( Chrysops silacea ), Chrysops atlanticus , Cochliomyia hominivorax , Cordylobia anthropophaga , Culicoides furens , Culex pipiens , Culex nigripalpus ), Culex quinquefasciatus , Culex tarsalis , Culiseta inornata , Culiseta melanura , Dermatobia hominis , Fannia canicularis , Gasterophilus intestinalis , Glossina morsitans , Glossina palpalis , Glossina fuscipes , Glossina tachinoides , Haematobia irritans , Saddle Haplodiplosis equestris , Hippelates spp. , Hypoderma lineata , Leptoconops torrens , Lucilia caprina , Lucilia cuprina , mercerized Lucilia sericata , Lycoria pectoralis , Mansonia spp. , Musca domestica , Muscina stabulans , Oestrus ovis , silvery Phlebotomus argentipes , Psorophora columbiae , Psorophora discolor , Prosimulium mixtum , Sarcophaga haemorrhoidalis , Sarcophaga sp. ), Chlorophytum gnat ( Simulium vittatum ), barb fly ( Stomoxys calcitrans ), gadfly ( Tabanus bovinus ), black horsefly ( Tabanus atratus ), slender horsefly ( Tabanus lineola ) and zebrafly ( Tabanus similis ), lice (lice ( Phthiraptera )), such as Pediculus humanus capitis , Pediculus humanus corporis , Pthirus pubis , Haematopinus eurysternus , Haematopinus suis , bovine jaw louse ( Linognathus vituli ), Bovicola bovis , Menopon gallinae , Menacanthus stramineus and Solenopotes capillatus , ticks and parasitic mites ( Parasitiformes )): Ticks (suborder Ixodida ), such as Ixodes scapularis , Ixodes holocyclus , Ixodes pacificus , Rhiphicephalus sanguineus , Angler's Rocky Mountain Tick ( Dermacentor andersoni ), Dog Tick ( Dermacentor variabilis ), American Flower Tick ( Amblyomma americanum ), Gulf Ear Tick ( Ambryommama culatum ), Rodent Tick ( Ornithodorus hermsi ), Relapsing Fever Tick Lice ( Ornithodorus turicata ) and parasitic mites ( Mesostigmata ), such as Ornithonyssus bacoti and Dermanyssus gallinae , Actinedida (former stigmata ( Prostigmata )) and Acaridida ( Astigma ata )), such as Acarapis spp. , Cheyletiella spp. , Ornithocheyletia spp. , Myobia spp. , Myobia spp. ( Psorergates spp. ), Demodex spp. , Trombicula spp. , Listrophorus spp. , Acarus spp. , Tyrophagus spp. ), Caloglyphus spp. , Hypodectes spp. , Pterolichus spp. , Psoroptes spp. , Chorioptes spp. , ear mange Otodectes spp. , Sarcoptes spp. , Notoedres spp. , Knemidocoptes spp. , Cytodites spp. and Laminosioptes spp. ), stink bugs ( Heteropterida ): Temperate bedbugs ( Cimex lectularius ), tropical bedbugs ( Cimex hemipterus ), old insectivorous stinkbugs ( Reduvius senilis ), Triatoma spp . , red-bellied bugs Rhodnius ssp. , Panstrongylus ssp. , and Arilus critatus , Anoplurida , e.g. Haematopinus spp . Pediculus spp. , Phtirus spp. and Solenopotes spp. , Mallophagida ( Arnblycerina and Ischnocerina ) , such as Trimenopon spp. , Menopon spp. , Trimenopon spp . noton spp. ), Bovicola spp. , Werneckiella spp. , Lepikentron spp . , Trichodectes spp. and Felicola spp. .

Ascaris nematodes (Roundworms Nematoda) :

Roundworms ( Wipeworm ) and Trichinosis ( Trichosyringida ) such as Trichinellidae ( Trichinella spp. ), ( Trichuridae ) Trichuris spp. ), Capillaria spp. , Rhabditida , e.g. Rhabditis spp. , Strongyloides spp. , Helichalobus spp. ), Strongylidae , e.g. Strongylus spp. , Ancylostoma spp. , Necator americanus , Bunostomum spp. ( Hookworm ), hair Trichostrongylus spp. , Haemonchus contortus. , Ostertagia spp. , Cooperia spp. , Nematodirus spp. , Dictyocaulus spp. , Cyathostoma spp. , Oesophagostomum spp. , Stephanurus dentatus , Ollulanus spp . Chabertia spp. , Stephanurus dentatus , Syngamus trachea , Ancylostoma spp. , Uncinaria spp. , Globocephalus spp . Necator spp. , Metastrongylus spp. , Muellerius capillaris, Protostrongylus spp. , Angiostrongylus us spp. ), Parelaphosstrongylus spp. ), cat lungworm ( Aleurostrongylus abstrusus ) and kidney nematode ( Dioctophyma renale ), gastrointestinal roundworms ( Ascaridida ) such as human roundworm ( Ascaris lumbricoides ), pig Ascaris suum , Ascaridia galli , Parascaris equorum , Enterobius vermicularis ( Threadworm ), Toxocara canis , Toxascaris leonine , Skrjabinema spp. and Oxyuris equi , Camallanida , e.g. Dracunculus medinensis ( Guinea worm ), Spirurida ), such as Thelazia spp. , Wuchereria spp . , Brugia spp. , Onchocerca spp. , Heartworm ( Dirofilaria spp. ), Dipetalonema spp. , Setaria spp. , Elaeophora spp. , Spirocerca lupi and Habronema spp . ), hookworms (Acanthocephala ( Acanthocephala )), such as Acanthocephalus spp. , Macracanthorhynchus hirudinaceus and Oncicola spp. , planarians Species ( Plathelminthes ): flukes ( Trematoda ), e.g. Faciola spp. , Fascioloides magna , Paragonimus spp. , Dicoela ( D icrocoelium spp. ), Fasciolopsis buski , Chinese liver fluke ( Clonorchis sinensis ), Schistosoma spp. , Trichobilharzia spp. , winged winged fluke ( Alaria alata ), Paragonimus spp. and Nanocyetes spp. , Cercomeromorpha , especially Cestoda , Tapeworms , such as 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 .

The compounds of formula (I) and compositions comprising them are especially useful for controlling pests of the orders Diptera, Fleas and Ticks.

In one embodiment, the present invention provides a compound of formula (I) and a composition comprising the compound for controlling mosquitoes.

In one embodiment, the present invention provides a use of a compound of formula (I) and a composition comprising the compound for controlling flies.

In one embodiment, the present invention provides a use of a compound of formula (I) and a composition comprising the compound for controlling fleas.

The use of the compound of the present invention and the composition comprising the compound for combating ticks is also another embodiment of the present invention.

The compounds according to the invention are also especially useful against endoparasites (Ascaris nematodes, hookworms and planarians).

In one embodiment, administration of the compounds of the invention can be done prophylactically as well as therapeutically.

In another embodiment, the administration of the compound of the invention is carried out directly or in a suitable formulation, orally, topically/transdermally or parenterally.

For oral administration to warm-blooded animals, the compounds of the invention may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets Doses, Boluses and Capsules. Alternatively, the compounds of the present invention can be administered to animals in their drinking water. For oral administration, the selected dosage form should provide the animal with 0.01 mg to 100 mg of the compound of the present invention per kilogram of animal body weight per day, preferably 0.5 mg to 100 mg of the compound of the present invention per kilogram of animal body weight per day.

Alternatively, compounds of the invention may be administered to animals parenterally, eg, by intrarumen, 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 invention may be formulated as implants for subcutaneous administration. Additionally, the compounds of the present invention can be administered transdermally to animals. For parenteral administration, the selected dosage form should provide the animal with 0.01 mg to 100 mg of the compound of the present invention per kilogram of animal body weight per day.

The compounds of the invention may also be in the form of dips, powders, powders, loops, wafers, sprays, shampoos, drop-and-pour formulations and in the form of ointments or oil-in-water emulsions or water-in-oil emulsions. applied to animals. For surface application, dips and sprays generally contain from 0.5 ppm to 5000 ppm and preferably from 1 ppm to 3000 ppm of the compound of the invention. In addition, the compounds of the present invention may be formulated as ear tags for animals, especially quadrupeds such as cattle and sheep.

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

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. The solution is sterile filtered and aseptically filled.

Oral solutions are administered directly. Concentrates are administered orally after pre-diluted to the concentration used. Oral solutions and concentrates are prepared according to the prior art and as described above for injectable solutions, sterile procedures not being necessary.

Solutions for use on the skin are dripped, spread, wiped, sprayed or sprayed on.

Solutions for application to the skin are prepared according to the prior art and as described above for injection solutions, sterile procedures not being necessary.

The gel is applied or spread on the skin or introduced into a body cavity. Gels are prepared by treating solutions prepared as described for injectable solutions with sufficient thickening agent formed of a clear material having an ointment-like consistency.

Pour-on formulations are poured or sprayed on a defined area of the skin and 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. Where appropriate, other auxiliaries are added, such as coloring agents, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives.

Emulsions can be administered orally, transdermally, or by injection. Emulsions are either water-in-oil or oil-in-water.

This is achieved by dissolving the active compound in a hydrophobic phase or in a hydrophilic phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries (such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity Reinforcing substances) are prepared by homogenizing it with other phase solvents.

Suspensions can be administered orally or topically/transdermally. They are prepared by suspending the active compounds in suspending agents, if appropriate by adding further auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers.

Liquid suspensions are all homogeneous solvents and solvent mixtures.

Semisolid formulations can be administered orally or topically/transdermally. It differs from the aforementioned suspensions and emulsions only by its higher viscosity.

To prepare solid preparations, the active compound is mixed with suitable excipients (via addition of auxiliaries where appropriate) and brought into the desired form.

In general, "parasiticidally effective amount" means the amount of active ingredient required to achieve an observable effect on growth, including necrosis, death, delay, prevention and removal, destruction or otherwise reduction of the target Effects on the emergence and activity of living organisms. The parasiticidally effective amount of the various compounds/compositions used in the present invention may vary. A 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 application, and the like. Compositions useful in the present invention generally contain from about 0.001% to 95% of a compound of the present invention.

In general, it is appropriate to administer the compounds of the present invention in a total amount of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day. The ready-to-use preparations contain the effect at a concentration of 10 ppm to 80% by weight, preferably 0.1% to 65% by weight, more preferably 1% to 50% by weight, most preferably 5% to 40% by weight Compounds acting on parasites, preferably ectoparasites. The preparation diluted before use contains the compound acting on ectoparasites in a concentration of 0.5% to 90% by weight, preferably 1% to 50% by weight. Furthermore, the formulations contain the compounds according to the invention against endoparasites in concentrations of 10 ppm to 2% by weight, preferably 0.05% to 0.9% by weight, especially preferably 0.005% to 0.25% by weight.

In a preferred embodiment, the compositions comprising the compounds of the invention are applied transdermally/topically.

In another embodiment, the surface application is in the form of shaped articles containing the compound, such as loops, discs, ear tags, strips and adhesive strips and foils for fixing on body parts.

It is generally advisable to administer a solid formulation releasing a total amount of 10 mg to 300 mg, preferably 20 mg to 200 mg, most preferably 25 mg to 160 mg, of the compound of the invention per kg body weight of the animal treated over a period of three weeks. thing.

In the preparation of 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 which are well compatible with the compounds of the invention. A detailed list of plastics and elastomers and procedures for the preparation of shaped articles is set forth, for example, in PCT Patent Publication No. WO 2003/086075.

Positive crop response:

The compounds of the present invention are not only effective in controlling insect and acarid pests, but also exhibit positive crop responses, such as plant growth promoting effects such as enhanced root growth and increased resistance to drought, high salinity, high temperature, cold, frost or light radiation receptivity), increased flowering, improved nutrient utilization (such as increased nitrogen assimilation), improved plant product quality, increased productive tiller (tiller) number, enhanced resistance to fungi, insects and pests, etc., thereby increasing Yield.

Chemical example:

The following examples illustrate, but are not limited to, the manner and method of preparing the compounds of the present invention and include the best mode contemplated by the inventors for carrying out the invention.

example -1 : 7- Cyclopropyl -2-( ethylsulfonyl )-3-(5-(2,2,3,3,3- Pentafluoropropoxy ) pyrazine -2- base ) Pyrazolo [1,5-a] Pyrimidine ( 7-cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine ; compound 3 ) Synthesis

step - 1 : 5-(2,2,3,3,3- Pentafluoropropoxy ) pyrazine -2- carboxylic acid (5-(2,2,3,3,3-pentafluoropropoxy)pyrazine-2-carboxylic acid)

Sodium hydride (NaH ). The reaction mixture was stirred at 25 °C for 12 hours. After the reaction was complete, the reaction mixture was poured into ice water (200 mL) and extracted with ethyl acetate (3 x 100 mL). The combined ethyl acetate layers were washed with water (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 5-(2,2,3,3,3-pentafluoropropoxy)pyrazine-2 as a solid - Formic acid (9 g , z, 52.4% yield). ¹ H-NMR (400 MHz, DMSO- d 6) δ 13.47 (s, 1H), 8.85-8.84 (m, 1H), 8.57 (d, J = 1.2 Hz, 1H), 5.21 (td, J = 13.7, 1.0 Hz, 2H); ESI MS (m/z) 270.85(MH)-.

step -2 : 5-(2,2,3,3,3- Pentafluoropropoxy ) pyrazine -2- base ) Methanol (5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)methanol)

To a stirred solution of 5-(2,2,3,3,3-pentafluoropropoxy)pyrazine-2-carboxylic acid (1 g, 3.67 mmol) in tetrahydrofuran (THF; 30 mL) at 25 °C 1,1'-Carbonyldiimidazole (CDI; 0.89 g, 5.51 mmol) was added in . The reaction mixture was stirred at 25 °C for 12 hours. Sodium borohydride ( _NaBH4 ; 0.28 g, 7.35 mmol) in water (10 mL) was added to the reaction mixture as a solution, and the resulting mixture was stirred at 25 °C for 2 hours. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate (EtOAc; 2 x 100 mL). The combined ethyl acetate layers were washed with brine (100 mL), dried over sodium sulfate and concentrated to give the crude product, which was subjected to flash column chromatography on silica gel using 20% ethyl acetate Hexane solution was used as eluent for purification to give (5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)methanol (650 mg, 2.52 mmol) as an oily substance ; 68.5% yield). ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.39 (d, J = 1.5 Hz, 1H), 8.26 (t, J = 0.7 Hz, 1H), 5.49 (t, J = 5.7 Hz, 1H), 5.13 (td, J = 13.8, 1.1 Hz, 2H), 4.58-4.57 (m, 2H); ESI MS (m/z) 258.55 (MH)+.

step - 3 : 2-( Chloromethyl )-5-(2,2,3,3,3- Pentafluoropropoxy ) pyrazine (2-(chloromethyl)-5-(2,2,3,3,3-pentafluoropropoxy)pyrazine)

(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)methanol (6 g, 23.24 mmol) in toluene (100 mL) was stirred at 25 °C Thionyl chloride (8.5 ml, 116 mmol) was added to the solution. The reaction mixture was stirred at 100 °C for 12 hours. After the reaction was complete, the reaction mixture was cooled to 25 °C and poured into water. The aqueous layer was extracted with ethyl acetate (EtOAc; 2 x 50 mL), and the combined ethyl acetate layers were washed with saturated aqueous sodium bicarbonate (50 mL), brine (50 mL), dried over anhydrous sodium sulfate and concentrated to get the crude product. The crude product was purified by silica gel flash column chromatography using 10% ethyl acetate in hexane as eluent to give 2-(chloromethyl)-5-(2,2,3,3 ,3-pentafluoropropoxy)pyrazine (4.7 g, 16.99 mmol; 73.1% yield). ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.50-8.46 (m, 1H), 8.42-8.38 (m, 1H), 5.19-5.05 (m, 2H), 4.88-4.80 (m, 2H).

step -4 : 2-(5-(2,2,3,3,3- Pentafluoropropoxy ) pyrazine -2- base ) Acetonitrile (2-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)acetonitrile)

To a stirred solution of 2-(chloromethyl)-5-(2,2,3,3,3-pentafluoropropoxy)pyrazine (5.0 g, 18.08 mmol) in acetonitrile (5 mL) was added three Methylsilyl nitrile (4.9 mL, 36.2 mmol) and tetra-n-butylammonium fluoride (tetra -n -butylammonium fluoride; TBAF) (36.2 mL, 36.2 mmol), and the resulting mixture was stirred at 25 °C 14 hours. After the reaction was complete, the reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate (2 x 100 mL). The combined ethyl acetate layers were washed with brine (50 mL), dried over sodium sulfate and concentrated to give the crude product, which was subjected to flash column chromatography on silica gel using 20% ethyl acetate in hexane as eluent Purification was performed to give 2-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)acetonitrile (3.2 g, 11.98 mmol; 66.3% yield). ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.50 (d, J = 1.2 Hz, 1H), 8.28 (t, J = 0.6 Hz, 1H), 5.18-5.09 (m, 2H), 4.23 (s , 2H); ESI MS (m/z) 265.85 (MH)-.

step -5 : 3,3- pair ( Ethylthio )-2-(5-(2,2,3,3,3- Pentafluoropropoxy ) pyrazine -2- base ) Acrylonitrile (3,3-bis(ethylthio)-2-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)acrylonitrile)

Dissolve 2-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)acetonitrile (3 g, 11.23 mmol) in acetonitrile (60 mL) at 25 °C Potassium hydroxide (1.32 g, 23.58 mmol) was added to the stirred solution of . The resulting mixture was stirred at 25 °C for 1 h. Then, the reaction mixture was cooled to -5 °C, and carbon disulfide (0.81 mL, 13.48 mmol) was added dropwise over 10 minutes. After the addition was complete, the reaction mixture was stirred at -5 °C for 1 h. Then, ethyl iodide (2.0 mL, 24.70 mmol) was added dropwise to the reaction mixture at the same temperature within 15 minutes. The resulting reaction mixture was stirred at 0 °C for 2 hours, then at 25 °C for 16 hours. The reaction mixture was concentrated under reduced pressure, and the resulting crude product was purified by silica gel flash column chromatography using 10% ethyl acetate in hexane as the eluent to obtain 3,3-bis(ethylthio)- 2-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)acrylonitrile (2.6 g, 6.51 mmol; 58.0% yield). ¹ H-NMR (400 MHz, CHCl ₃ - d ) δ 8.44 (d, J = 1.5 Hz, 1H), 8.39 (d, J = 1.5 Hz, 1H), 4.91-4.85 (m, 2H), 3.10 (q , J = 7.3 Hz, 2H), 2.96 (q, J = 7.4 Hz, 2H), 1.42 (q, J = 7.3 Hz, 3H), 1.29-1.24 (m, 3H); ESI MS (m/z) 399.85 (MH)+.

step -6 : 3-( Ethylthio )-4-(5-(2,2,3,3,3- Pentafluoropropoxy ) pyrazine -2- base )-1H- pyrazole -5- amine (3-(ethylthio)-4-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-1H-pyrazol-5-amine)

At 0 °C, 3,3-bis(ethylthio)-2-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)acrylonitrile ( To a stirred solution of 4.1 g, 10.27 mmol) in a mixture of acetonitrile (30 mL) and ethanol (30 mL) was added dropwise hydrazine hydrate (0.63 mL, 10.27 mmol (79% w/v)). The resulting mixture was stirred at 0 °C for 1 h. The reaction mixture was diluted with ice water (20 mL) and the precipitated solid was filtered. The solid was washed with water and dried under reduced pressure to give the crude product, which was purified by flash column chromatography on silica gel using 100% ethyl acetate in hexane as eluent to give 3-(ethyl sulfide yl)-4-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-1H-pyrazol-5-amine (2.8 g, 7.58 mmol; 73.9% Yield). ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 11.91 (s, 1H), 8.64 (d, J = 26.7 Hz, 1H), 8.39 (s, 1H), 6.05 (d, J = 11.5 Hz, 2H ), 5.19-5.08 (m, 2H), 3.05-2.82 (m, 2H), 1.33-1.20 (m, 3H); ESI MS (m/z) 370.10 (MH)+.

step -7 : 2-( Ethylthio )-3-(5-(2,2,3,3,3- Pentafluoropropoxy ) pyrazine -2- base ) Pyrazolo [1,5-a] pyrimidine -7(4H)- ketone (2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one)

To 3-(ethylthio)-4-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-1H-pyrazol-5-amine (2.5 g , 6.77 mmol) in acetic acid (25 mL) was added methyl 3,3-dimethoxypropionate (1.50 g, 10.15 mmol). The resulting mixture was heated at 100 °C for 16 h. It was cooled to 25 °C under reduced pressure. Water was added to the crude product, and then the above crude product was extracted with ethyl acetate (3 x 100 mL). The combined ethyl acetate layers were washed with water (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product, which was subjected to silica gel flash column chromatography using 5% methanol in dichloromethane as The eluate was purified to give 2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1 ,5-a]pyrimidin-7(4H)-one (1.5 g, 3.56 mmol; 52.6% yield). ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 12.05 (s, 1H), 8.58 (d, J = 1.5 Hz, 1H), 8.49 (d, J = 1.5 Hz, 1H), 7.81 (d, J = 7.6 Hz, 1H), 5.85 (d, J = 7.3 Hz, 1H), 5.19 (dd, J = 13.7, 13.0 Hz, 2H), 3.25 (q, J = 7.3 Hz, 2H), 1.37 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 421.50 (MH)+.

step -8 : 7- bromine -2-( ethylsulfonyl )-3-(5-(2,2,3,3,3- Pentafluoropropoxy ) pyrazine -2- base ) Pyrazolo [1,5-a] pyrimidine (7-bromo-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine)

At 25 °C, to 2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1, 5-a] A stirred solution of pyrimidin-7(4H)-one (1.6 g, 3.80 mmol) in acetonitrile (30 mL) was added potassium carbonate (1.05 g, 7.59 mmol) and phosphorus oxybromide (2.18 g, 7.59 mmol). The resulting mixture was heated at 90 °C for 6 hours. After the reaction was complete, the reaction mixture was cooled to 0 °C and diluted with ice-water mixture (50 mL). The pH of the mixture was adjusted to 7-8 by slowly adding a saturated aqueous solution of sodium bicarbonate. The aqueous layer was extracted with ethyl acetate (3 x 100 mL), and the combined ethyl acetate layers were washed with water (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product, which was flashed through silica gel Column chromatography, using 50% ethyl acetate in hexane as eluent, was purified to give 7-bromo-2-(ethylsulfonyl)-3-(5-(2,2,3 ,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (0.6 g, 1.162 mmol; 30.6% yield). ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.77 (t, J = 1.1 Hz, 1H), 8.55 (d, J = 1.5 Hz, 1H), 8.48 (d, J = 4.6 Hz, 1H), 7.65 (d, J = 4.6 Hz, 1H), 3.92 (s, 3H), 3.25 (q, J = 7.3 Hz, 2H), 1.40 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 483.95 (MH; 79Br)+, 485.95 (MH; 81Br)+.

step -9 : 7- bromine -2-( ethylsulfonyl )-3-(5-(2,2,3,3,3- Pentafluoropropoxy ) pyrazine -2- base ) Pyrazolo [1,5-a] pyrimidine (7-bromo-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine)

At 0-5 °C, to 7-bromo-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl) A stirred solution of pyrazolo[1,5-a]pyrimidine (0.3 g, 0.62 mmol) in dichloromethane (10 mL) was added portion wise to m-chloroperbenzoic acid ( m -chloroperbenzoic acid; 0.3 g , 1.30 mmol). The resulting mixture was stirred at 25 °C for 2 h. After the reaction was complete, the reaction mixture was diluted with aqueous sodium thiosulfate, and the reaction mixture was extracted with dichloromethane (2 x 15 mL). The combined ethyl acetate layer was washed with a saturated aqueous solution of sodium bicarbonate (50 mL) and water (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product, which was subjected to silica gel flash column chromatography , purified using 35% ethyl acetate in hexane as eluent to give 7-bromo-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3- Pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (210 mg, 0.41 mmol; 65.7% yield). ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.69 (d, J = 1.5 Hz, 1H), 8.63-8.62 (m, 2H), 7.90 (d, J = 4.4 Hz, 1H), 5.23 (t , J = 13.7 Hz, 2H), 3.78-3.73 (m, 2H), 1.27-1.22 (m, 3H); ESI MS (m/z) 517.90 (MH; 79Br)+, 519.90 (MH; 81Br)+.

step -10 : 7- Cyclopropyl -2-( ethylsulfonyl )-3-(5-(2,2,3,3,3- Pentafluoropropoxy ) pyrazine -2- base ) Pyrazolo [1,5-a] pyrimidine (7-cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine)

To 7-bromo-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1, 5-a] A stirred solution of pyrimidine (150 mg, 0.29 mmol) and cyclopropylboronic acid (125 mg, 1.45 mmol) in a mixture of dioxane (6 mL) and water (2 mL) was added to tripotassium phosphate (154 mg , 0.73 mmol). The reaction mixture was thoroughly deoxygenated by passing through vacuum/nitrogen cycles three times. Then 1,1'-bis(diphenylphosphino)ferrocene-dichloropalladium(II) dichloromethane complex (23.8 mg, 0.03 mmol) was added to the reaction mixture, and then Heat for 2 hours. After the reaction was complete, the reaction mixture was cooled to 25 °C and filtered through a pad of celite. The filtrate was concentrated under reduced pressure, and the crude product was purified by silica gel flash column chromatography using 20% ethyl acetate in hexane as eluent to obtain 7-cyclopropyl-2-(ethylsulfonate Acyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (65 mg, 0.136 mmol ; 46.9% yield). ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.71 (d, J = 1.5 Hz, 1H), 8.66 (d, J = 4.4 Hz, 1H), 8.61 (d, J = 1.5 Hz, 1H), 7.06 (d, J = 4.6 Hz, 1H), 5.22 (t, J = 13.3 Hz, 2H), 3.76 (q, J = 7.4 Hz, 2H), 2.90-2.84 (m, 1H), 1.43-1.38 (m , 2H), 1.27-1.16 (m, 5H); ESI MS (m/z), 478.15 (MH)+.

Example -2 : N- cyclopropyl -2-( ethylthio )-3-(5-(2,2,3,3,3 -pentafluoropropoxy ) pyrazin -2- yl ) pyrazolo [1,5-a] pyrimidin -7- amine ( N-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1 ,5-a] pyrimidin-7-amine ; compound 7 ) synthesis

At 0 °C, to 7-bromo-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazole A stirred solution of di[1,5-a]pyrimidine (step-8; Example 1; 0.15 g, 0.310 mmol) in N,N-dimethylformamide (DMF; 2 mL) was added dropwise to cyclopropylamine ( 0.09 g, 1.55 mmol). The resulting mixture was stirred at 25 °C for 3 h. The reaction mixture was diluted with ice-cold water (10 mL), and the aqueous layer was extracted with ethyl acetate (3 x 10 mL). The combined ethyl acetate layers were washed with water (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product, which was subjected to silica gel flash column chromatography using 1% methanol in dichloromethane as The eluate was purified to give N-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazine-2 as a solid -yl)pyrazolo[1,5-a]pyrimidin-7-amine (90 mg, 0.195 mmol; 63.1% yield). ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.24 (d, J = 1.5 Hz, 1H), 8.45 (d, J = 1.5 Hz, 1H), 8.30 (d, J = 5.4 Hz, 1H), 8.23 (s, 1H), 6.44 (d, J = 5.4 Hz, 1H), 5.18-5.11 (m, 2H), 3.26 (t, J = 7.3 Hz, 2H), 2.73 (dt, J = 8.7, 3.4 Hz , 1H), 1.34 (t, J = 7.3 Hz, 3H), 0.92-0.85 (m, 2H), 0.78-0.74 (m, 2H); ESI MS (m/z) 460.50 [(MH)+].

Example -3 : 7 - Ethoxy -2-( ethylthio )-3-(5-(2,2,3,3,3 -pentafluoropropoxy ) pyrazin -2- yl ) pyrazolo [1,5-a] pyrazin -2-yl)pyrazolo[1,5-a ]pyrimidine ; compound 11 ) synthesis

To a stirred solution of ethanol (0.05 g, 1.03 mmol) in anhydrous tetrahydrofuran (THF; 5 mL) at 0 °C was added sodium hydride (0.03 g, 0.77 mmol), followed by 7-bromo-2-(ethylsulfur yl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (0.25 g, 0.52 mmol) After adding tetrahydrofuran (THF; 5 mL), the reaction mixture was stirred at the same temperature for 30 minutes. After stirring the reaction at 0 °C for 15 minutes, the reaction mixture was heated to 25 °C and stirred for an additional 2 hours. After the reaction was complete, ice-cold water (10 mL) was added to the reaction mixture, and the resulting precipitate was filtered, then washed with water (10 mL) and concentrated under reduced pressure to obtain a crude product. The crude product was purified by washing with diethyl ether to give 7-ethoxy-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazine- 2-yl)pyrazolo[1,5-a]pyrimidine (85 mg, 0.189 mmol; 36.6% yield). ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.21 (d, J = 1.5 Hz, 1H), 8.53 (d, J = 5.1 Hz, 1H), 8.50 (d, J = 1.5 Hz, 1H), 6.73 (d, J = 5.4 Hz, 1H), 5.16 (dd, J = 13.8, 12.8 Hz, 2H), 4.58 (q, J = 7.0 Hz, 2H), 3.19 (q, J = 7.4 Hz, 2H), 1.49 (t, J = 7.1 Hz, 3H), 1.36 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 450.60 [(MH)+].

Example -4 : ((2-( Ethylsulfonyl )-3-(5-(2,2,3,3,3 -pentafluoropropoxy ) pyrazin -2- yl ) pyrazolo [1 ,5-a] pyrimidin -7- yl ) imino ) dimethyl -λ ⁶ -pyridine ( ((2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy) synthesis of pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)imino)dimethyl-λ ⁶ -sulfanone ; compound 6 )

To 7-bromo-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1, A stirred solution of 5-a]pyrimidine (200 mg, 0.39 mmol) in toluene ^{(6 mL) was added with iminodimethyl-λ 6 -sulfanone} (72.2 mg, 0.77 mmol), triphosphate Potassium phosphate, tribasic; 164 mg, 0.77 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl; 36.9 mg, 0.077 mmol), then the reaction mixture was degassed under nitrogen for 5 minutes. Tris(dibenzylideneacetone)dipalladium(0) (35.5 mg, 0.04 mmol) was added, degassing was continued for another 5 minutes, and the reaction mixture was heated to 110 °C for 2 hours. After completion of the reaction, the reaction mixture was filtered through a pad of celite and washed with ethyl acetate. The combined organic layers were washed with water (50 mL) and dried over sodium sulfate, concentrated under reduced pressure to give crude product. The crude product was purified by flash column chromatography on silica gel using 1-2% methanol in dichloromethane to give ((2-(ethylsulfonyl)-3-(5-(2 ,2,3,3,3-pentafluoropropoxy)pyrazin-2)-yl)pyrazolo[1,5-a]pyrimidin-7-yl)imino)dimethyl-l6-pyridine (90 mg, 0.17 mmol; 44.0% yield). ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.72 (d, J = 1.5 Hz, 1H), 8.57 (d, J = 1.5 Hz, 1H), 8.41 (d, J = 5.1 Hz, 1H), 6.82 (d, J = 5.1 Hz, 1H), 5.25-5.18 (m, 2H), 3.74 (t, J = 7.5 Hz, 2H), 3.69 (s, 6H), 1.22 (t, J = 7.5 Hz, 3H) ; ESI MS (m/z), 528.90 (MH)+.

Example -5 : 7- cyclopropyl -2-( ethylsulfonyl )-3- iodopyrazolo [1,5-a] pyrimidine (7-cyclopropyl-2-(ethylsulfonyl)-3-iodopyrazolo[1 ,5-a]pyrimidine) synthesis

step 1 : 2-( Ethylthio )-7- Hydroxypyrazolo [1,5-a] pyrimidine -3- ethyl formate (ethyl 2-(ethylthio)-7-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylate) Synthesis

At 120 °C, 5-amino-3-(ethylthio)-1H-pyrazole-4-carboxylic acid ethyl ester (10 g, 46.5 mmol) and 3,3-dimethoxypropionic acid methyl ester (9.9 ml, 69.7 mmol) in acetic acid (250 mL) was heated for 18 hours. After the reaction was complete, the acetic acid was removed under reduced pressure, and the crude reaction mixture was diluted with cold water to give a pale yellow precipitate. The yellow solid was filtered and washed with water (500 mL) and n-hexane (500 mL), followed by drying under reduced pressure to give 2-(ethylthio)-7-hydroxypyrazolo[1,5-a]pyrimidine - Ethyl 3-carboxylate (10 g, 37.4 mmol; 81% yield). ¹ H-NMR (400 MHz, DMSO- d6 ) δ 11.87 (s, 1H), 7.76 (d, J = 7.6 Hz, 1H), 5.91 (d, J = 7.6 Hz, 1H), 4.29 (q, J = 7.1 Hz, 2H), 3.10-3.17 (m, 2H), 1.32-1.37 (m, 3H), 1.26-1.32 (m, 3H); ESI MS (m/z) 268 (MH)+.

step 2 : 7- bromine -2-( Ethylthio ) Pyrazolo [1,5-a] pyrimidine -3- ethyl formate (ethyl 7-bromo-2-(ethylthio)pyrazolo[1,5-a]pyrimidine-3-carboxylate) Synthesis

To ethyl 2-(ethylthio)-7-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylate (5 g, 18.7 mmol) stirred in acetonitrile (100 mL) at 25 °C Potassium carbonate (K ₂ CO ₃ ; 7.76 g, 56.1 mmol) and phosphorus oxybromide (16.1 g, 56.1 mmol) were added to the solution, and the resulting mixture was heated at 95° C. for 4 hours. The reaction mixture was cooled to 25 °C, and the reaction mixture was added to a cold water mixture (250 mL), then basified with a saturated solution of sodium bicarbonate (adjusted to its pH = 7-8), and dissolved in ethyl acetate (2 x 250 mL) extraction. The combined organic layers were washed with a saturated solution of brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude compound, which was subjected to silica gel flash column chromatography using 50% ethyl acetate in hexane Purification was carried out as eluent to give ethyl acetate 7-bromo-2-(ethylthio)pyrazolo[1,5-a]pyrimidine-3-carboxylate (5 g, 15.1 mmol; 81% yield Rate). ¹ H-NMR (400 MHz, CHLOROFORM- d ) δ 8.43 (d, J = 4.6 Hz, 1H), 7.20 (d, J = 4.6 Hz, 1H), 4.47 (q, J = 7.1 Hz, 2H), 3.30 (q, J = 7.4 Hz, 2H), 1.47-1.51 (m, 3H), 1.42-1.60 (m, 3H); ESI MS (m/z) 331.75 (MH)+.

step 3 : 7- Cyclopropyl -2-( Ethylthio ) Pyrazolo [1,5-a] pyrimidine -3- ethyl formate (ethyl 7-cyclopropyl-2-(ethylthio)pyrazolo[1,5-a]pyrimidine-3-carboxylate) Synthesis

Ethyl 7-bromo-2-(ethylthio)pyrazolo[1,5-a]pyrimidine-3-carboxylate (7 g, 21.20 mmol), cyclopropylboronic acid (7.28 g, 85 mmol) were removed under nitrogen. ) and tripotassium phosphate (13.45 g, 63.6 mmol) in dioxane (70 mL) for 10 minutes, followed by the addition of 1,1'-bis(diphenylphosphino)ferrocene-palladium dichloride (II ) dichloromethane adduct (1,1'-bis(diphenylphosphino) ferrocene-palladium(II) dichloride dichloromethane adduct; 1.73 g, 2.12 mmol). The resulting reaction mixture was heated at 90 °C for 3 hours. After the reaction was complete, the reaction mixture was cooled to 25 °C, filtered through a pad of celite and washed with ethyl acetate. The organic layer was washed with water (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the crude product, which was subjected to flash column chromatography on silica gel and washed with 50% ethyl acetate in hexane. Purified to give ethyl-7-cyclopropyl-2-(ethylthio)pyrazolo[1,5-a]pyrimidine-3-carboxylate (3 g, 10.3 mmol; 48.6% yield). ¹ H-NMR (400 MHz, CHLOROFORM- d ) δ 8.55 (d, J = 4.8 Hz, 1H), 6.39 (d, J = 4.8 Hz, 1H), 4.53-4.44 (m, 2H), 3.35-3.24 ( m, 2H), 1.50-1.37 (m, 8H), 1.22-1.12 (m, 2H); ESI MS (m/z) 291.95 (MH)+.

step 4 : 7- Cyclopropyl -2-( Ethylthio ) Pyrazolo [1,5-a] pyrimidine -3- carboxylic acid (7-cyclopropyl-2-(ethylthio)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid) Synthesis

To a stirred solution of ethyl 7-cyclopropyl-2-(ethylthio)pyrazolo[1,5-a]pyrimidine-3-carboxylate (3 g, 10.3 mmol) in ethanol (30 mL) was added hydroxide Lithium monohydrate (4.32 g, 103 mmol) in water (30 mL). The reaction mixture was stirred at 60 °C for 4 hours. After the reaction was complete, the resulting mixture was then heated at 95 °C for 4 hours. The reaction mixture was cooled to 25 °C, concentrated under reduced pressure to obtain a residue, which was acidified (adjusted to pH=1) by concentrated hydrochloric acid (HCl). The resulting solid was filtered and dried under reduced pressure to give 7-cyclopropyl-2-(ethylthio)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (2.2 g, 8.4 mmol; 81 %Yield). ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.51 (d, J = 4.9 Hz, 1H), 6.81 (d, J = 4.8 Hz, 1H), 3.20-3.14 (m, 2H), 2.85-2.73 (m, 1H), 1.38 (t, J = 7.3 Hz, 3H), 1.35-1.31 (m, 2H), 1.24-1.20 (m, 2H); ESI MS (m/z) 264.00 (MH)+.

step 5 : 7- Cyclopropyl -2-( Ethylthio )-3- Iodopyrazolo [1,5-a] pyrimidine (7-cyclopropyl-2-(ethylthio)-3-iodopyrazolo[1,5-a]pyrimidine) Synthesis

Under nitrogen atmosphere and 0 °C, to the N,N of 7-cyclopropyl-2-(ethylthio)pyrazolo[1,5-a]pyrimidine-3-carboxylic - To a stirred solution of dimethylformamide (50 mL) was added iodine (9.64 g 38.0 mmol) and potassium phosphate (3.31 g, 18.99 mmol). The reaction mixture was heated at 100 °C for 8 hours. After the reaction was completed, the reaction mixture was cooled to 25 °C, and then a mixture of 15% aqueous sodium thiosulfate and saturated aqueous _NaHCO3 was added with stirring. The aqueous layer was extracted with dichloromethane (4 x 25 mL), and the combined organic layers were dried under reduced pressure to obtain the crude product, which was subjected to silica gel flash column chromatography using 20-40% ethyl acetate Purification with alkane solution as eluent to obtain 7-cyclopropyl-2-(ethylthio)-3-iodopyrazolo[1,5-a]pyrimidine (5 g, 14.48 mmol; 76% yield). ¹ H-NMR (400 MHz, CHLOROFORM- d ) δ 8.34 (d, J = 4.8 Hz, 1H), 6.25 (d, J = 4.4 Hz, 1H), 3.29-3.23 (m, 2H), 2.95-2.84 ( m, 1H), 1.46 (t, J = 7.6 Hz, 3H), 1.36-1.30 (m, 2H), 1.15-1.11 (m, 2H).

step 6 : 7- Cyclopropyl -2-( ethylsulfonyl )-3- Iodopyrazolo [1,5-a] pyrimidine (7-cyclopropyl-2-(ethylsulfonyl)-3-iodopyrazolo[1,5-a]pyrimidine) Synthesis

Add 7-cyclopropyl-2-(ethylthio)-3-iodopyrazolo[1,5-a]pyrimidine (200 mg, 0.58 mmol) in dichloromethane (10 mL ) was added m-chloroperoxybenzoic acid (mCPBA; 286 mg, 1.16 mmol), and the reaction mixture was stirred at 25 °C for a further 12 hours. After the reaction was complete, the reaction mixture was diluted with dichloromethane (15 mL). The organic layer was washed with 1 N sodium hydroxide (NaOH; 10 mL), dried over anhydrous sodium sulfate and filtered under reduced pressure and the organic layer was concentrated to obtain a crude product, which was subjected to silica gel flash column chromatography using 20- Purification with 40% ethyl acetate in hexane as eluent gave 7-cyclopropyl-2-(ethylsulfonyl)-3-iodopyrazolo[1,5-a]pyrimidine as a solid (150 mg, 0.398 mmol; 68.6% yield). ¹ H-NMR (400 MHz, CHLOROFORM- d ) δ 8.56 (d, J = 4.6 Hz, 1H), 6.54 (d, J = 4.6 Hz, 1H), 3.48 (q, J = 7.4 Hz, 2H), 3.02 -2.95 (m, 1H), 1.49-1.45 (m, 2H), 1.44-1.37 (m, 3H), 1.16-1.12 (m, 2H); ESI MS (m/z) 377.85 (MH)+.

Example -6 : 3-(7- cyclopropyl -2-( ethylthio ) pyrazolo [1,5-a] pyrimidin -3- yl )-1- methyl -6-(2,2,3 ,3,3- pentafluoropropoxy ) pyridin -2(1H)-one ( 3-(7-cyclopropyl-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-1-methyl -6-(2,2,3,3,3-pentafluoropropoxy)pyridin-2(1H)-one ; compound 110 ) synthesis

step 1 : 1- methyl -6-(2,2,3,3,3- Pentafluoropropoxy )-3-(4,4,5,5- Tetramethyl -1,3,2- Dioxaborolane -2- base ) (1-methyl-6-(2,2,3,3,3-pentafluoropropoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2 (1H)- ketone ) Synthesis

Toluene (1 mL) to 3-bromo-1-methyl-6-(2,2,3,3,3-pentafluoropropoxy)pyridin-2(1H)-one (500 mg, 1.49 mmol) A stirred solution of bis(pinacolato)diboron (bis(pinacolato)diboron; 756 mg, 2.98 mmol) and potassium acetate (292 mg, 2.98 mmol) were added, and the resulting mixture was deoxygenated under nitrogen flow for 10 minutes. Then PdCl ₂ (dppf)-CH ₂ Cl ₂ adduct (60.8 mg, 0.074 mmol) was added to the above reaction mixture, and the resulting mixture was stirred at 100° C. for 1 hr. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (50 mL) and water (50 mL). The aqueous layer was extracted with ethyl acetate (2 X 30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give the crude product 1-methyl-6-(2,2,3,3,3-pentafluoropropoxy)-3- (4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one (400 mg, 1.488 mmol; 70.2% yield ), the crude product was used in the next step without further purification. ESI MS (m/z) 301.90 (MH)+.

step 2 : 3-(7- Cyclopropyl -2-( Ethylthio ) Pyrazolo [1,5-a] pyrimidine -3- base )-1- methyl -6-(2,2,3,3,3- Pentafluoropropoxy ) pyridine -2(1H)- ketone( 3-(7-cyclopropyl-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-1-methyl-6-(2,2,3,3,3-pentafluoropropoxy)pyridin-2( 1H)-one) ; compound 110 )Synthesis

7-Cyclopropyl-2-(ethylthio)-3-iodopyrazolo[1,5-a]pyrimidine (1 g, 2.90 mmol), 1-methyl-6-(2 ,2,3,3,3-pentafluoropropoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine -2(1H)-ketone (2.22 g, 5.79 mmol) and potassium carbonate (K ₂ CO ₃ ; 1.20 g, 8.69 mmol) in 1,4-dioxane (10 mL ) and water (1 mL) for 10 minutes, followed by the addition of 1,1'-bis(diphenylphosphino)ferrocene-dichloropalladium(II) dichloromethane adduct (0.24 g, 0.29 mmol ). The resulting reaction mixture was heated at 110 °C for 4 hours. After the reaction was complete, the reaction mixture was cooled to 25 °C, filtered through a pad of celite and washed with ethyl acetate. The ethyl acetate layer was washed with water (25 mL) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude product, which was subjected to silica gel flash column chromatography using 80% ethyl acetate in hexane Purified by washing to give 3-(7-cyclopropyl-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-1-methyl-6-(2,2 , 3,3,3-pentafluoropropoxy)pyridin-2(1H)-one (150 mg, 0.316 mmol; 10.91% yield). ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.28 (d, J = 4.4 Hz, 1H), 7.50 (d, J = 8.1 Hz, 1H), 6.61 (d, J = 4.4 Hz, 1H), 6.04 (d, J = 8.1 Hz, 1H), 5.07 (t, J = 12.6 Hz, 2H), 3.37 (d, J = 9.5 Hz, 3H), 3.10 (q, J = 7.3 Hz, 2H), 2.81- 2.77 (m, 1H), 1.32-1.28 (m, 5H), 1.22-1.16 (m, 2H); ESI MS (m/z) 475.55 (MH)+.

Example -7 : 3-(7- cyclopropyl -2-( ethylsulfonyl ) pyrazolo [1,5-a] pyrimidin -3- yl )-1- methyl -6-(2,2 ,3,3,3- pentafluoropropoxy ) pyridin -2(1H)-one ( 3-(7-cyclopropyl-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-1 -methyl-6-(2,2,3,3,3-pentafluoropropoxy)pyridin-2(1H)-one ; compound 119 ) synthesis

The title compound 3-(7-cyclopropyl-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-1-methyl-6-(2, 2,3,3,3-Pentafluoropropoxy)pyridin-2(1H)-one (170 mg, 0.34 mmol; 12.7% yield) was synthesized from 7-cyclopropyl-2-(ethylsulfonyl )-3-iodopyrazolo[1,5-a]pyrimidine (1.0 g, 2.65 mmol), prepared by the procedure described in step 2 of Example-6. ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.52 (d, J = 4.6 Hz, 1H), 7.55 (d, J = 8.3 Hz, 1H), 6.96 (d, J = 4.6 Hz, 1H), 6.08 (d, J = 7.9 Hz, 1H), 5.11 (t, J = 12.7 Hz, 2H), 3.54 (q, J = 7.4 Hz, 2H), 3.38-3.36 (m, 4H), 2.83-2.79 (m , 1H), 1.39-1.34 (m, 2H), 1.25-1.18 (m, 5H); ESI MS (m/z) 506.70 (MH)+.

The compounds in Table 1 below were obtained using appropriate starting materials and following procedures analogous to those described in Example-1 to Example-7, or according to General Scheme 1 to General Scheme 15 described herein.

Table 1 Compound number Compound name data 1 2-(Ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine-7 (4H)-keto(2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7(4H) -one) ¹ H-NMR (400 MHz, DMSO- d6 ) δ 12.03 (s, 1H), 8.58 (d, J = 1.5 Hz, 1H), 8.49 (d, J = 1.5 Hz, 1H), 7.81 (d, J = 7.6 Hz, 1H), 5.85 (d, J = 7.3 Hz, 1H), 5.19 (t, J = 13.7 Hz, 2H), 3.25 (q, J = 7.3 Hz, 2H), 1.37 (t, J = 7.3 Hz , 3H); ESI MS (m/z) 419.40, 421.50 (MH)+. 2 7-Bromo-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a ] pyrimidine (7-bromo-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d6 ) δ 9.17 (d, J = 1.5 Hz, 1H), 8.54 (d, J = 1.5 Hz, 1H), 8.47 (d, J = 4.6 Hz, 1H), 7.57 (d, J = 4.6 Hz, 1H), 5.18 (t, J = 13.8 Hz, 2H), 3.23 (q, J = 7.3 Hz, 2H), 1.41 (t, J = 7.3 Hz, 3H); ESI MS ( m/z), 483.95, 485.95 [(MH)+ Br79, 81]. 3 7-cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1 ,5-a]pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine ) ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.71 (d, J = 1.5 Hz, 1H), 8.66 (d, J = 4.4 Hz, 1H), 8.61 (d, J = 1.5 Hz, 1H), 7.06 (d, J = 4.6 Hz, 1H), 5.22 (t, J = 13.3 Hz, 2H), 3.76 (q, J = 7.4 Hz, 2H), 2.90-2.84 (m, 1H), 1.43-1.38 (m, 2H), 1.27-1.16 (m, 5H); ESI MS (m/z), 478.15 (MH)+. 4 7-cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1 ,5-a]pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine ) ¹ H-NMR (400 MHz, DMSO- d6 ) δ 9.21 (d, J = 1.5 Hz, 1H), 8.51 (q, J = 1.5 Hz, 2H), 6.77 (d, J = 4.6 Hz, 1H), 5.17 (t, J = 13.3 Hz, 2H), 3.23 (q, J = 7.3 Hz, 2H), 2.84 (d, J = 5.1 Hz, 1H), 1.40 (t, J = 7.3 Hz, 3H), 1.36-1.33 (m, 2H), 1.27-1.24 (m, 2H); ESI MS (m/z), 446.00 (MH)+. 5 ((2-(Ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine -7-yl)imino)dimethyl-l6-pyridine (((2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo [1,5-a]pyrimidin-7-yl)imino)dimethyl-l6-sulfanone_ ¹ H-NMR (400 MHz, DMSO- d6 ) δ 9.23 (d, J = 1.5 Hz, 1H), 8.47 (d, J = 1.5 Hz, 1H), 8.28 (d, J = 5.1 Hz, 1H), 6.58 (d, J = 5.1 Hz, 1H), 5.16 (t, J = 13.6 Hz, 2H), 3.63 (s, 6H), 3.19 (q, J = 7.4 Hz, 2H), 1.34 (t, J = 7.5 Hz , 3H); ESI MS (m/z), 496.90 (MH)+. 6 ((2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a ]pyrimidin-7-yl)imino)dimethyl-l6-pyridine (((2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl )pyrazolo[1,5-a]pyrimidin-7-yl)imino)dimethyl-l6-sulfanone) ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.72 (d, J = 1.5 Hz, 1H), 8.57 (d, J = 1.5 Hz, 1H), 8.41 (d, J = 5.1 Hz, 1H), 6.82 (d, J = 5.1 Hz, 1H), 5.25-5.18 (m, 2H), 3.74 (t, J = 7.5 Hz, 2H), 3.69 (s, 6H), 1.22 (t, J = 7.5 Hz, 3H) ; ESI MS (m/z), 528.90 (MH)+. 7 N-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a]pyrazin-7-amine (N-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a ]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d6 ) δ 9.24 (d, J = 1.5 Hz, 1H), 8.45 (d, J = 1.5 Hz, 1H), 8.30 (d, J = 5.4 Hz, 1H), 8.23 (s, 1H), 6.44 (d, J = 5.4 Hz, 1H), 5.18-5.11 (m, 2H), 3.26 (t, J = 7.3 Hz, 2H), 2.73 (dt, J = 8.7, 3.4 Hz, 1H), 1.34 (t, J = 7.3 Hz, 3H), 0.92-0.85 (m, 2H), 0.78-0.74 (m, 2H); ESI MS (m/z) 460.50 [(MH)+]. 8 2-(Ethylthio)-N-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5- a]pyrazin-7-amine (2-(ethylthio)-N-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a] pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d6 ) δ 9.25 (d, J = 1.5 Hz, 1H), 8.45 (d, J = 1.5 Hz, 1H), 8.26 (d, J = 5.4 Hz, 1H), 7.98 (q, J = 4.8 Hz, 1H), 6.22 (d, J = 5.6 Hz, 1H), 5.15 (dd, J = 13.8, 12.8 Hz, 2H), 3.26 (q, J = 7.3 Hz, 2H), 3.02 (d, J = 4.9 Hz, 3H), 1.36 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 435.55 [(MH)+]. 9 2-(Ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-N-(2,2,2-trifluoroethane Base) pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-N -(2,2,2-trifluoroethyl)pyrazolo[1,5-a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d6 ) δ 9.24 (d, J = 1.5 Hz, 1H), 8.47-8.42 (m, 2H), 8.34 (d, J = 5.4 Hz, 1H), 6.60 (d, J = 5.4 Hz, 1H), 5.16 (dd, J = 13.8, 12.8 Hz, 2H), 4.43-4.34 (m, 2H), 3.27 (d, J = 7.6 Hz, 2H), 1.37 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 502.40 [(MH)+]. 10 2-(Ethylthio)-7-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5- a] pyrimidine (2-(ethylthio)-7-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d6 ) δ 9.21 (d, J = 1.5 Hz, 1H), 8.57 (d, J = 4.3 Hz, 1H), 8.51 (d, J = 1.5 Hz, 1H), 7.08 (dd, J = 4.3, 0.9 Hz, 1H), 5.17 (td, J = 13.8, 0.8 Hz, 2H), 3.22 (q, J = 7.4 Hz, 2H), 2.76 (s, 3H), 1.39 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 420.40 [(MH)+]. 11 7-ethoxy-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a] pyrimidine (7-ethoxy-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d6 ) δ 9.21 (d, J = 1.5 Hz, 1H), 8.53 (d, J = 5.1 Hz, 1H), 8.50 (d, J = 1.5 Hz, 1H), 6.73 (d, J = 5.4 Hz, 1H), 5.16 (dd, J = 13.8, 12.8 Hz, 2H), 4.58 (q, J = 7.0 Hz, 2H), 3.19 (q, J = 7.4 Hz, 2H), 1.49 (t, J = 7.1 Hz, 3H), 1.36 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 450.60 [(MH)+]. 12 2-(Ethylsulfonyl)-N-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1, 5-a]pyrazin-7-amine (2-(ethylsulfonyl)-N-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5- a] pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.75 (d, J = 1.5 Hz, 1H), 8.56 (d, J = 1.5 Hz, 1H), 8.44 (d, J = 4.6 Hz, 1H), 8.37 (d, J = 5.4 Hz, 1H), 6.43 (d, J = 5.6 Hz, 1H), 5.21 (t, J = 13.8 Hz, 2H), 3.77 (q, J = 7.4 Hz, 2H), 3.04 (d , J = 4.9 Hz, 3H), 1.23 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 466.85 [(MH)+]. 13 2-(Ethylsulfonyl)-N,N-dimethyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo [1,5-a]pyrimidin-7-amine (2-(ethylsulfonyl)-N,N-dimethyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo [1,5-a]pyrimidin-7-amine) ¹ H NMR (400 MHz, DMSO- d6 ) δ 8.73 (d, J = 1.5 Hz, 1H), 8.57 (d, J = 1.5 Hz, 1H), 8.37 (d, J = 5.4 Hz, 1H), 6.51 ( d, J = 5.4 Hz, 1H), 5.21 (t, J = 13.8 Hz, 2H), 3.74 (q, J = 7.4 Hz, 2H), 3.41 (s, 6H), 1.24 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 480.95 [(MH)+]. 14 N-(cyclopropylmethyl)-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyridine Azolo[1,5-a]pyrimidin-7-amine (N-(cyclopropylmethyl)-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl )pyrazolo[1,5-a]pyrimidin-7-amine) ¹ H NMR (400 MHz, DMSO- d6 ) δ 8.75 (d, J = 1.5 Hz, 1H), 8.56 (d, J = 1.2 Hz, 1H), 8.51 (s, 1H), 8.35 (d, J = 5.4 Hz, 1H), 6.59 (d, J = 5.4 Hz, 1H), 5.21 (t, J = 13.7 Hz, 2H), 3.79 (q, J = 7.4 Hz, 2H), 3.36 (t, J = 5.9 Hz, 2H), 1.26-1.20 (m, 4H), 0.52-0.47 (m, 2H), 0.36 (q, J = 4.9 Hz, 2H); ESI MS (m/z) 507.00 [(MH)+]. 15 2-(Ethylsulfonyl)-N-isobutyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1 ,5-a]pyrazin-7-amine (2-(ethylsulfonyl)-N-isobutyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d6 ) δ 8.74 (d, J = 1.5 Hz, 1H), 8.56 (d, J = 1.2 Hz, 1H), 8.49 (t, J = 6.5 Hz, 1H), 8.33 (d, J = 5.4 Hz, 1H), 6.54 (d, J = 5.6 Hz, 1H), 5.24-5.17 (m, 2H), 3.78 (q, J = 7.4 Hz, 2H), 3.28 (d, J = 6.8 Hz, 2H), 3.16 (d, J = 5.1 Hz, 1H), 1.24 (t, J = 7.3 Hz, 3H), 0.94 (d, J = 6.8 Hz, 6H); ESI MS (m/z) 509.00 [(MH)+]. 16 N-(cyclopropylmethyl)-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo [1,5-a]pyrazin-7-amine (N-(cyclopropylmethyl)-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo [1,5-a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d6 ) δ 9.25 (d, J = 1.5 Hz, 1H), 8.46-8.43 (m, 1H), 8.23 (d, J = 5.6 Hz, 1H), 8.15 (d, J = 5.1 Hz, 0H), 8.03 (t, J = 6.2 Hz, 1H), 6.37 (d, J = 5.4 Hz, 1H), 5.15 (t, J = 13.4 Hz, 2H), 3.34 (t, J = 6.6 Hz, 2H), 3.27 (t, J = 7.3 Hz, 2H), 1.36 (t, J = 7.5 Hz, 3H), 1.23-1.17 (m, 1H), 0.52-0.47 (m, 2H), 0.37- 0.33 (m, 2H); ESI MS (m/z) 475.70 [(MH)+]. 17 2-(ethylthio)-N,N-dimethyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1 ,5-a]pyrazin-7-amine (2-(ethylthio)-N,N-dimethyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1 ,5-a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d6 ) δ 9.27 (d, J = 1.5 Hz, 1H), 8.46 (d, J = 1.5 Hz, 1H), 8.25 (d, J = 5.6 Hz, 1H), 6.29 (d, J = 5.4 Hz, 1H), 5.15 (dd, J = 13.8, 12.8 Hz, 2H), 3.39 (s, 6H), 3.16 (q, J = 7.3 Hz, 2H), 1.38 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 449.65 [(MH)+]. 18 N-cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1 ,5-a]pyrazin-7-amine (N-cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.76 (s, 1H), 8.72 (d, J = 1.2 Hz, 1H), 8.56 (d, J = 1.2 Hz, 1H), 8.42 (d, J = 5.4 Hz, 1H), 6.65 (d, J = 5.4 Hz, 1H), 5.21 (t, J = 13.6 Hz, 2H), 3.76 (q, J = 7.4 Hz, 2H), 2.77-2.73 (m, 1H ), 1.23 (t, J = 7.5 Hz, 3H), 0.92-0.88 (m, 2H), 0.80-0.77 (m, 2H); ESI MS (m/z) 493.00 (MH)+. 19 N-ethyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5- a]pyrazin-7-amine (N-ethyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a] pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.25 (d, J = 1.5 Hz, 1H), 8.45 (d, J = 1.5 Hz, 1H), 8.23 (d, J = 5.5 Hz, 1H), 8.00 (t, J = 6.3 Hz, 1H), 6.30 (d, J = 5.5 Hz, 1H), 5.15 (dd, J = 14.2, 13.3 Hz, 2H), 3.52-3.45 (m, 2H), 3.27 (q , J = 7.4 Hz, 2H), 1.36 (t, J = 7.5 Hz, 3H), 1.24 (t, J = 7.2 Hz, 3H); ESI MS (m/z) 448.95 (MH)+. 20 N-ethyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1, 5-a]pyrazin-7-amine (N-ethyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5- a] pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.74 (d, J = 1.2 Hz, 1H), 8.56 (d, J = 1.5 Hz, 1H), 8.46 (t, J = 6.2 Hz, 1H), 8.35 (d, J = 5.4 Hz, 1H), 6.52 (d, J = 5.6 Hz, 1H), 5.24-5.15 (m, 2H), 3.80-3.74 (m, 2H), 3.54-3.47 (m, 2H) , 1.26-1.16 (m, 6H); ESI MS (m/z) 481.35 (MH)+. twenty one (7-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine-2- Base)(ethyl)(imino)-l6-pyrazin((7-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a]pyrimidin-2-yl)(ethyl)(imino)-l6-sulfanone) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.89 (d, J = 1.5 Hz, 1H), 8.64 (d, J = 4.4 Hz, 1H), 8.61 (d, J = 1.5 Hz, 1H), 7.01 (d, J = 4.6 Hz, 1H), 5.22 (t, J = 13.8 Hz, 2H), 4.70 (s, 1H), 3.66-3.60 (m, 2H), 2.89-2.82 (m, 1H), 1.41 -1.37 (m, 2H), 1.31 (t, J = 7.3 Hz, 3H), 1.28-1.24 (m, 2H); ESI MS (m/z) 476.90 (MH)+. twenty two 6-Bromo-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a ] pyrimidine (6-bromo-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.66 (d, J = 2.2 Hz, 1H), 9.10 (d, J = 1.5 Hz, 1H), 8.75 (d, J = 2.2 Hz, 1H), 8.54-8.53 (m, 1H), 5.21-5.14 (m, 2H), 3.18 (q, J = 7.3 Hz, 2H), 1.38-1.35 (m, 3H); ESI MS (m/z) 485.90 (MH) +. twenty three 2-(Ethylsulfonyl)-7-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1, 5-a] pyrimidine (2-(ethylsulfonyl)-7-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.73 (d, J = 4.3 Hz, 1H), 8.72-8.71 (m, 1H), 8.61 (d, J = 1.5 Hz, 1H), 7.38 (dd , J = 4.3, 0.9 Hz, 1H), 5.23 (dd, J = 13.8, 12.8 Hz, 2H), 3.75 (q, J = 7.4 Hz, 2H), 2.83 (s, 3H), 1.26-1.21 (m, 3H); ESI MS (m/z) 452.00 (MH)+. twenty four 6-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a] pyrimidine (6-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.15 (d, J = 1.5 Hz, 1H), 8.97 (d, J = 1.8 Hz, 1H), 8.58 (d, J = 2.1 Hz, 1H), 8.51 (d, J = 1.5 Hz, 1H), 5.17 (dd, J = 14.2, 13.3 Hz, 2H), 3.17 (q, J = 7.4 Hz, 2H), 2.08-2.01 (m, 1H), 1.36 (t , J = 7.3 Hz, 3H), 1.03-0.96 (m, 2H), 0.94-0.88 (m, 2H); ESI MS (m/z) 446.30 (MH)+. 25 2-(Ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (2 -(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.19-9.17 (m, 2H), 8.68 (q, J = 1.9 Hz, 1H), 8.52 (d, J = 1.5 Hz, 1H), 7.11 (dd , J = 6.9, 4.1 Hz, 1H), 5.21-5.14 (m, 2H), 3.19 (q, J = 7.3 Hz, 2H), 1.37 (t, J = 7.3 Hz, 3H); ESI MS (m/z ) 406.15 (MH)+. 26 (6-Cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine-2- Base)(ethyl)(imino)-l6-pyrazin((6-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a]pyrimidin-2-yl)(ethyl)(imino)-l6-sulfanone) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.11 (dd, J = 2.2, 0.5 Hz, 1H), 8.83 (d, J = 1.5 Hz, 1H), 8.70 (d, J = 2.1 Hz, 1H ), 8.60 (d, J = 1.5 Hz, 1H), 5.21 (dd, J = 13.8, 12.8 Hz, 2H), 4.64 (s, 1H), 3.57 (q, J = 7.3 Hz, 2H), 1.26 (t , J = 7.3 Hz, 3H), 1.07-1.02 (m, 2H), 0.96-0.92 (m, 2H); ESI MS (m/z) 477.05 (MH)+. 27 2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.39 (dd, J = 7.1, 1.7 Hz, 1H), 8.83 (q, J = 2.0 Hz, 1H), 8.72 (d, J = 1.2 Hz, 1H ), 8.62 (d, J = 1.5 Hz, 1H), 7.43 (dd, J = 7.1, 4.2 Hz, 1H), 5.23 (t, J = 13.6 Hz, 2H), 3.74 (q, J = 7.4 Hz, 2H ), 1.23 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 438.00 (MH)+. 28 N-(tert-butyl)-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo [1,5-a]pyrimidin-6-amine (N-(tert-butyl)-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl )pyrazolo[1,5-a]pyrimidin-6-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.24 (d, J = 1.5 Hz, 1H), 8.46 (d, J = 1.5 Hz, 1H), 8.25 (d, J = 5.6 Hz, 1H), 6.74 (s, 1H), 6.53 (d, J = 5.6 Hz, 1H), 5.15 (dd, J = 13.8, 12.8 Hz, 2H), 3.23 (q, J = 7.3 Hz, 2H), 1.52 (s, 9H ), 1.36 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 476.60 (MH)+. 29 6-Bromo-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a] pyrimidine (6-bromo-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.91 (d, J = 2.0 Hz, 1H), 8.92 (d, J = 2.2 Hz, 1H), 8.67 (d, J = 1.5 Hz, 1H), 8.62 (d, J = 1.5 Hz, 1H), 5.22 (dd, J = 14.3, 13.3 Hz, 2H), 3.74 (q, J = 7.4 Hz, 2H), 1.22 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 517.85 (MH)+. 30 6-cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1 ,5-a]pyrazolo[1,5-a]pyrimidine ) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.17 (dd, J = 2.1, 0.6 Hz, 1H), 8.73 (d, J = 2.2 Hz, 1H), 8.69 (d, J = 1.5 Hz, 1H ), 8.61 (d, J = 1.5 Hz, 1H), 5.22 (dd, J = 13.9, 13.0 Hz, 2H), 3.72 (q, J = 7.4 Hz, 2H), 2.15-2.09 (m, 1H), 1.21 (t, J = 7.5 Hz, 3H), 1.09-1.00 (m, 2H), 0.97-0.93 (m, 2H); ESI MS (m/z) 477.80 (MH)+. 31 ((2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a ]pyrimidin-6-yl)imino)dimethyl-l6-pyridine (((2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl )pyrazolo[1,5-a]pyrimidin-6-yl)imino)dimethyl-l6-sulfanone) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.68 (t, J = 2.2 Hz, 2H), 8.60 (d, J = 1.5 Hz, 1H), 8.50 (d, J = 2.4 Hz, 1H), 5.25-5.18 (m, 2H), 3.72 (q, J = 7.3 Hz, 2H), 3.39 (s, 6H), 1.23 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 529.25 (MH )+. 32 Ethyl((2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a]pyrimidin-6-yl)imino)(methyl)-l6-sulfonyl(ethyl((2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin -2-yl)pyrazolo[1,5-a]pyrimidin-6-yl)imino)(methyl)-l6-sulfanone) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.68 (t, J = 2.2 Hz, 2H), 8.60 (d, J = 1.5 Hz, 1H), 8.52 (d, J = 2.4 Hz, 1H), 5.25-5.18 (m, 2H), 3.69 (q, J = 7.3 Hz, 2H), 3.54 (q, J = 7.3 Hz, 2H), 3.25 (s, 3H), 1.34 (t, J = 7.5 Hz, 3H ), 1.22 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 543.05 (MH)+. 33 2-(Ethylsulfonyl)-6-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1, 5-a] pyrimidine (2-(ethylsulfonyl)-6-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.24 (q, J = 1.1 Hz, 1H), 8.75 (d, J = 2.2 Hz, 1H), 8.70 (d, J = 1.5 Hz, 1H), 8.61 (d, J = 1.5 Hz, 1H), 5.22 (t, J = 13.8 Hz, 2H), 3.73 (q, J = 7.4 Hz, 2H), 2.41 (d, J = 1.0 Hz, 3H), 1.24- 1.19 (m, 3H); ESI MS (m/z) 452.05 (MH)+. 34 Ethyl((2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a ]pyrimidin-6-yl)imino)(methyl)-l6-pyrazin(ethyl((2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2 -yl)pyrazolo[1,5-a]pyrimidin-6-yl)imino)(methyl)-l6-sulfanone) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.12 (d, J = 1.5 Hz, 1H), 8.56 (d, J = 2.4 Hz, 1H), 8.50 (d, J = 1.5 Hz, 1H), 8.41 (d, J = 2.4 Hz, 1H), 5.16 (t, J = 13.3 Hz, 2H), 3.48 (q, J = 7.2 Hz, 2H), 3.25 (s, 3H), 3.17 (q, J = 7.3 Hz, 2H), 1.38-1.31 (m, 6H); ESI MS (m/z) 511.00 (MH)+. 35 ((2-(Ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine -6-yl) imino) dimethyl-l6-yl (((2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo [1,5-a]pyrimidin-6-yl)imino)dimethyl-l6-sulfanone) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.13 (d, J = 1.5 Hz, 1H), 8.55 (d, J = 2.4 Hz, 1H), 8.50 (d, J = 1.5 Hz, 1H), 8.39 (d, J = 2.4 Hz, 1H), 5.20-5.13 (m, 2H), 3.34 (s, 6H), 3.17 (q, J = 7.3 Hz, 2H), 1.36 (t, J = 7.3 Hz, 3H ); ESI MS (m/z) 497.00 (MH)+. 36 2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-6-(pyrimidin-5-yl)pyridine Azolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-6-(pyrimidin-5-yl )pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.98 (d, J = 2.2 Hz, 1H), 9.37 (s, 2H), 9.33 (d, J = 2.2 Hz, 1H), 9.31 (s, 1H ), 8.75 (d, J = 1.2 Hz, 1H), 8.65 (d, J = 1.5 Hz, 1H), 5.24 (t, J = 13.3 Hz, 2H), 3.78 (q, J = 7.4 Hz, 2H), 1.28-1.23 (m, 3H); ESI MS (m/z) 516.05 (MH)+. 37 7-Bromo-2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a ]pyrimidine (7-bromo-2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.72 (d, J = 9.3 Hz, 1H), 8.46 (d, J = 4.6 Hz, 1H), 7.59 (d, J = 4.6 Hz, 1H), 7.52 (d, J = 9.5 Hz, 1H), 5.35-5.29 (m, 2H), 3.23 (q, J = 7.4 Hz, 2H), 1.42 (t, J = 7.3 Hz, 3H); ESI MS (m/ z) 485.85 (MH)+. 38 6-(3,5-Difluorophenyl)-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazine-2- Base) pyrazolo[1,5-a]pyrimidine (6-(3,5-difluorophenyl)-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin- 2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.90 (d, J = 2.2 Hz, 1H), 9.29 (d, J = 2.2 Hz, 1H), 8.74 (d, J = 1.5 Hz, 1H), 8.64 (d, J = 1.5 Hz, 1H), 7.81-7.75 (m, 2H), 7.41 (tt, J = 9.3, 2.2 Hz, 1H), 5.24 (t, J = 13.8 Hz, 2H), 3.77 (q , J = 7.3 Hz, 2H), 1.25 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 550.00 (MH)+. 39 2-(Ethylsulfonyl)-6-(4-fluorophenyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyridine Azolo[1,5-a]pyrazin-2-yl)pyrazolo [1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.77 (d, J = 2.2 Hz, 1H), 9.22 (d, J = 2.3 Hz, 1H), 8.75 (d, J = 1.5 Hz, 1H), 8.64 (d, J = 1.5 Hz, 1H), 7.99-7.94 (m, 2H), 7.45-7.40 (m, 2H), 5.24 (dd, J = 13.8, 12.8 Hz, 2H), 3.77 (q, J = 7.3 Hz, 2H), 1.25 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 532.05 (MH)+. 40 1-(2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5- a] pyrimidin-6-yl) ethane-1-one (1-(2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[ 1,5-a]pyrimidin-6-yl)ethan-1-one) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 10.15 (d, J = 2.2 Hz, 1H), 9.13 (d, J = 2.1 Hz, 1H), 8.72 (d, J = 1.2 Hz, 1H), 8.64 (d, J = 1.5 Hz, 1H), 5.23 (t, J = 13.4 Hz, 2H), 3.79 (q, J = 7.4 Hz, 2H), 2.69-2.65 (m, 3H), 1.25 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 479.95 (MH)+. 41 7-Bromo-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5 -a]pyrimidine (7-bromo-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.64 (d, J = 4.4 Hz, 1H), 8.20 (d, J = 9.3 Hz, 1H), 7.92 (d, J = 4.6 Hz, 1H), 7.61-7.59 (m, 1H), 5.36 (dd, J = 13.7, 13.0 Hz, 2H), 3.83 (q, J = 7.4 Hz, 2H), 1.28-1.23 (m, 3H); ESI MS (m/z ) 517.85(MH)+. 42 7-Bromo-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a] pyrimidine (7-bromo-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, CHLOROFORM- d ) δ 8.77-8.76 (m, 1H), 8.50-8.47 (m, 2H), 7.45 (d, J = 4.4 Hz, 1H), 4.90 (td, J = 12.7 , 1.0 Hz, 2H), 3.80-3.74 (m, 2H), 1.46 (td, J = 7.5, 2.3 Hz, 3H); ESI MS (m/z) 517.80 (MH)+. 43 N-(tert-butyl)-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo [1,5-a]pyrimidin-7-amine (N-(tert-butyl)-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl )pyrazolo[1,5-a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, CHLOROFORM- d ) δ 8.79 (d, J = 1.5 Hz, 1H), 8.41 (d, J = 1.5 Hz, 1H), 8.36 (d, J = 5.4 Hz, 1H), 6.74 (s, 1H), 6.36 (d, J = 5.4 Hz, 1H), 4.88 (td, J = 12.8, 1.0 Hz, 2H), 3.77 (q, J = 7.4 Hz, 2H), 1.58 (s, 9H) , 1.42 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 508.90 (MH)+. 44 2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-N-(2,2,2-tri Fluoroethyl)pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl) -N-(2,2,2-trifluoroethyl)pyrazolo[1,5-a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.89 (t, J = 7.0 Hz, 1H), 8.74 (d, J = 1.2 Hz, 1H), 8.58 (d, J = 1.5 Hz, 1H), 8.48 (d, J = 5.1 Hz, 1H), 6.84 (d, J = 5.6 Hz, 1H), 5.25-5.18 (m, 2H), 4.40 (dd, J = 16.5, 9.4 Hz, 2H), 3.79 (q , J = 7.3 Hz, 2H), 1.24 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 534.95 (MH)+. 45 2-(Ethylsulfonyl)-7-(4-fluorophenyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyridine Azolo[1,5-a]pyrazin-2-yl)pyrazolo [1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.87 (d, J = 4.4 Hz, 1H), 8.73 (d, J = 1.5 Hz, 1H), 8.63 (d, J = 1.5 Hz, 1H), 8.25-8.22 (m, 2H), 7.62 (d, J = 4.4 Hz, 1H), 7.55-7.51 (m, 2H), 5.24 (dd, J = 13.9, 13.0 Hz, 2H), 3.72 (q, J = 7.3 Hz, 2H), 1.25 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 532.10 (MH)+. 46 2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine -7-amine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.75-8.73 (m, 1H), 8.56 (d, J = 1.5 Hz, 1H), 8.32-8.27 (m, 2H), 6.38 (d, J = 5.4 Hz, 2H), 5.21 (dd, J = 14.3, 13.3 Hz, 2H), 3.77 (q, J = 7.3 Hz, 2H), 1.24 (t, J = 7.3 Hz, 3H); ESI MS (m/z ) 452.90 (MH)+. 47 2-(Ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine-5 (4H)-Keto(2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-5(4H) -one) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 11.77 (s, 1H), 8.73 (s, 1H), 8.51-8.46 (m, 2H), 6.01 (d, J = 7.8 Hz, 1H), 5.19 -5.12 (m, 2H), 3.11 (q, J = 7.3 Hz, 2H), 1.33 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 421.95 (MH)+. 48 2-(Ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7-(pyrimidin-2-yl)pyrazolo [1,5-a]pyrimidine (2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7-(pyrimidin-2-yl)pyrazolo [1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6) δ 9.24 (d, J = 1.5 Hz, 1H), 9.12 (d, J = 4.9 Hz, 2H), 8.84 (d, J = 4.4 Hz, 1H), 8.54 (d, J = 1.5 Hz, 1H), 7.76 (t, J = 5.0 Hz, 1H), 7.44 (d, J = 4.4 Hz, 1H), 5.19 (t, J = 13.3 Hz, 2H), 3.02 ( q, J = 7.3 Hz, 2H), 1.30 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 483.90 (MH)+. 49 7-cyclopropyl-2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5 -a]pyrimidine (7-cyclopropyl-2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.78 (d, J = 9.5 Hz, 1H), 8.50 (d, J = 4.6 Hz, 1H), 7.48 (d, J = 9.3 Hz, 1H), 6.78 (d, J = 4.6 Hz, 1H), 5.34-5.28 (m, 2H), 3.23 (q, J = 7.3 Hz, 2H), 2.89-2.83 (m, 1H), 1.41 (t, J = 7.3 Hz , 3H), 1.37-1.31 (m, 2H), 1.30-1.24 (m, 2H); ESI MS (m/z) 446.30 (MH)+. 50 5-Bromo-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a ] pyrimidine (5-bromo-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.09 (d, J = 7.3 Hz, 1H), 9.01 (d, J = 1.5 Hz, 1H), 8.54 (d, J = 1.5 Hz, 1H), 7.29 (d, J = 7.1 Hz, 1H), 5.19 (t, J = 13.6 Hz, 2H), 3.18 (q, J = 7.3 Hz, 2H), 1.36 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 485.75 (MH)+. 51 N-(2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a] Pyrimidin-7-yl)cyclopropanecarboxamide (N-(2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a]pyrimidin-7-yl)cyclopropanecarboxamide) ¹ H-NMR (400 MHz, DMSO- d 6) δ 11.45 (s, 1H), 8.70-8.68 (m, 2H), 8.61 (d, J = 1.2 Hz, 1H), 7.90 (d, J = 5.1 Hz , 1H), 5.23 (t, J = 13.8 Hz, 2H), 3.81 (q, J = 7.4 Hz, 2H), 2.61-2.58 (m, 1H), 1.26 (t, J = 7.3 Hz, 3H), 1.22 (d, J = 3.9 Hz, 1H), 1.02-0.99 (m, 4H); ESI MS (m/z) 521.45 (MH)+. 52 7-cyclopropyl-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1 ,5-a]pyrimidine ) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.67 (d, J = 4.4 Hz, 1H), 8.23 (d, J = 9.0 Hz, 1H), 7.57 (d, J = 9.0 Hz, 1H), 7.07 (d, J = 4.6 Hz, 1H), 5.39-5.32 (m, 2H), 3.84 (q, J = 7.4 Hz, 2H), 2.90-2.86 (m, 1H), 1.44-1.39 (m, 2H) , 1.28-1.23 (m, 5H); ESI MS (m/z) 477.60 (MH)+. 53 2-(Ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-N-(2,2,2-trifluoroethane Base) pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-N -(2,2,2-trifluoroethyl)pyrazolo[1,5-a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.85-8.80 (m, 1H), 8.48 (t, J = 6.7 Hz, 1H), 8.33 (d, J = 5.4 Hz, 1H), 7.45 (d , J = 9.3 Hz, 1H), 6.62 (d, J = 5.6 Hz, 1H), 5.30 (t, J = 13.3 Hz, 2H), 4.44-4.35 (m, 2H), 3.28 (d, J = 7.3 Hz , 2H), 1.37 (dd, J = 15.0, 7.8 Hz, 3H); ESI MS (m/z) 503.05 (MH)+. 54 N-(tert-butyl)-2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1 ,5-a]pyridazin-7-amine (N-(tert-butyl)-2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo [1,5-a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.81 (d, J = 9.3 Hz, 1H), 8.24 (d, J = 5.6 Hz, 1H), 7.44 (d, J = 9.3 Hz, 1H), 6.78 (s, 1H), 6.55 (d, J = 5.6 Hz, 1H), 5.29 (dd, J = 14.1, 13.3 Hz, 2H), 3.24 (q, J = 7.4 Hz, 2H), 1.53 (s, 9H ), 1.38 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 477.15(MH)+. 55 2-(Ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine-7 -amine (2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.25 (d, J = 1.5 Hz, 1H), 8.44 (d, J = 1.5 Hz, 1H), 8.16 (d, J = 5.4 Hz, 1H), 7.92 (s, 2H), 6.18 (d, J = 5.1 Hz, 1H), 5.15 (t, J = 13.6 Hz, 2H), 3.25 (q, J = 7.3 Hz, 2H), 1.38-1.32 (m, 3H ); ESI MS (m/z) 421.10 (MH)+. 56 5-Bromo-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a] pyrimidine (5-bromo-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.32 (d, J = 7.3 Hz, 1H), 8.63 (dd, J = 3.9, 1.5 Hz, 2H), 7.63 (d, J = 7.1 Hz, 1H ), 5.23 (dd, J = 13.8, 12.8 Hz, 2H), 3.72 (q, J = 7.4 Hz, 2H), 1.22 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 517.95 (MH )+. 57 2-(Ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-N-(2,2,2-tri Fluoroethyl)pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl) -N-(2,2,2-trifluoroethyl)pyrazolo[1,5-a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.92 (t, J = 6.6 Hz, 1H), 8.48 (d, J = 5.4 Hz, 1H), 8.28 (d, J = 9.3 Hz, 1H), 7.55 (d, J = 9.3 Hz, 1H), 6.86 (d, J = 5.4 Hz, 1H), 5.34 (t, J = 13.7 Hz, 2H), 4.46-4.38 (m, 2H), 3.88 (q, J = 7.4 Hz, 2H), 1.25 (q, J = 7.3 Hz, 3H); ESI MS (m/z) 535.60 (MH)+. 58 N-(tert-butyl)-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo [1,5-a]pyridazin-7-amine (N-(tert-butyl)-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl )pyrazolo[1,5-a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.37 (d, J = 5.6 Hz, 1H), 8.28 (d, J = 9.3 Hz, 1H), 7.54 (d, J = 9.3 Hz, 1H), 6.98 (s, 1H), 6.77 (d, J = 5.6 Hz, 1H), 5.34 (t, J = 13.6 Hz, 2H), 3.87 (q, J = 7.3 Hz, 2H), 1.55 (s, 9H), 1.26 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 509.75 (MH)+. 59 2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7-(pyrimidin-2-yl)pyridine Azolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7-(pyrimidin-2-yl )pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.17 (d, J = 5.1 Hz, 2H), 8.99 (d, J = 4.2 Hz, 1H), 8.75 (d, J = 1.5 Hz, 1H), 8.64 (d, J = 1.5 Hz, 1H), 7.81 (t, J = 5.0 Hz, 1H), 7.77 (d, J = 4.2 Hz, 1H), 5.24 (t, J = 13.6 Hz, 2H), 3.68 ( q, J = 7.4 Hz, 2H), 1.22 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 516.00 (MH)+. 60 N-(2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5- a] pyrimidin-7-yl) acetamide (N-(2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a]pyrimidin-7-yl)acetamide) ¹ H-NMR (400 MHz, DMSO- d 6) δ 11.18 (s, 1H), 8.70-8.69 (m, 2H), 8.61 (d, J = 1.5 Hz, 1H), 7.93 (d, J = 5.1 Hz , 1H), 5.22 (t, J = 13.7 Hz, 2H), 3.80 (q, J = 7.4 Hz, 2H), 2.41 (s, 3H), 1.25 (t, J = 7.3 Hz, 3H); ESI MS ( m/z) 495.40 (MH)+. 61 N-(2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5- a]pyrimidin-7-yl)pivalamide (N-(2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1, 5-a]pyrimidin-7-yl)pivalamide) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.79 (s, 1H), 8.76 (d, J = 4.9 Hz, 1H), 8.74 (d, J = 1.2 Hz, 1H), 8.62 (d, J = 1.5 Hz, 1H), 7.82 (d, J = 5.1 Hz, 1H), 5.23 (t, J = 13.7 Hz, 2H), 3.79 (q, J = 7.3 Hz, 2H), 1.35 (s, 9H), 1.28 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 537.20 (MH)+. 62 2-(Ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-5-(pyrimidin-2-yl)pyrazolo [1,5-a]pyrimidine (2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-5-(pyrimidin-2-yl)pyrazolo [1,5-a]pyrimidine) ¹ H-NMR (400 MHz, CHLOROFORM- d ) δ 9.42 (d, J = 1.5 Hz, 1H), 8.99 (d, J = 4.9 Hz, 2H), 8.75 (d, J = 7.1 Hz, 1H), 8.45 (d, J = 1.5 Hz, 1H), 8.03 (d, J = 7.3 Hz, 1H), 7.42 (t, J = 4.8 Hz, 1H), 4.92 (td, J = 13.0, 1.0 Hz, 2H), 3.32 (q, J = 7.4 Hz, 2H), 1.50 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 483.95 (MH)+. 63 2-(Ethylsulfonyl)-N,N-dimethyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo [1,5-a]pyrimidin-5-amine (2-(ethylsulfonyl)-N,N-dimethyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo [1,5-a]pyrimidin-5-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.86-8.84 (m, 2H), 8.52 (d, J = 1.5 Hz, 1H), 6.95 (d, J = 8.1 Hz, 1H), 5.18 (t , J = 13.8 Hz, 2H), 3.77 (q, J = 7.3 Hz, 2H), 3.19 (s, 6H), 1.21 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 481.00 (MH )+. 64 2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-5-(pyrimidin-2-yl)pyridine Azolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-5-(pyrimidin-2-yl )pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6) δ 9.52 (d, J = 7.6 Hz, 1H), 9.10 (d, J = 4.6 Hz, 2H), 8.90 (d, J = 1.5 Hz, 1H), 8.66 (d, J = 1.5 Hz, 1H), 8.27 (d, J = 7.3 Hz, 1H), 7.71 (t, J = 4.9 Hz, 1H), 5.26 (s, 2H), 3.79 (d, J = 7.3 Hz, 2H), 1.25 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 515.95 (MH)+. 65 N-(2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5- a]pyrimidin-5-yl)cyclopropaneformamide (N-(2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1 ,5-a]pyrimidin-5-yl)cyclopropanecarboxamide) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 11.53 (s, 1H), 9.22 (d, J = 7.8 Hz, 1H), 8.76 (d, J = 1.5 Hz, 1H), 8.59 (d, J = 1.5 Hz, 1H), 8.08 (d, J = 7.8 Hz, 1H), 5.25-5.18 (m, 2H), 3.71 (q, J = 7.3 Hz, 2H), 2.08 (t, J = 6.0 Hz, 1H ), 1.22 (t, J = 7.3 Hz, 3H), 0.91-0.89 (m, 4H); ESI MS (m/z) 520.85 (MH)+. 66 5-cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1 ,5-a]pyrazolo[1,5-a]pyrimidine ) 1H-NMR (400 MHz, DMSO- d 6) δ 9.19 (d, J = 7.3 Hz, 1H), 8.74 (d, J = 1.5 Hz, 1H), 8.60-8.58 (m, 1H), 7.36 (d, J = 7.3 Hz, 1H), 5.22 (t, J = 13.4 Hz, 2H), 3.76 (q, J = 7.4 Hz, 2H), 2.35-2.30 (m, 1H), 1.23-1.11 (m, 7H); ESI MS (m/z) 477.95 (MH)+. 67 5-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a] pyrimidine (5-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.15 (d, J = 1.5 Hz, 1H), 8.97 (d, J = 7.1 Hz, 1H), 8.48 (d, J = 1.5 Hz, 1H), 7.07 (d, J = 7.1 Hz, 1H), 5.20-5.13 (m, 2H), 3.28 (s, 1H), 3.15 (q, J = 7.4 Hz, 2H), 2.33-2.27 (m, 1H), 1.35 (t, J = 7.3 Hz, 3H), 1.21-1.14 (m, 4H); ESI MS (m/z) 446.25 (MH)+. 68 (5-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine-2- Base)(ethyl)(imino)-l6-pyrazin((5-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a]pyrimidin-2-yl)(ethyl)(imino)-l6-sulfanone) ¹ H-NMR (400 MHz, DMSO- d 6) δ 9.13 (d, J = 7.3 Hz, 1H), 8.90 (d, J = 1.2 Hz, 1H), 8.59 (d, J = 1.5 Hz, 1H), 7.31 (d, J = 7.3 Hz, 1H), 5.21 (t, J = 13.3 Hz, 2H), 4.65 (s, 1H), 3.64-3.55 (m, 2H), 2.35-2.32 (m, 1H), 1.28 (t, J = 7.3 Hz, 3H), 1.22-1.13 (m, 4H); ESI MS (m/z) 477.30 (MH)+. 69 N-(2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5- a] pyrimidin-5-yl) acetamide (N-(2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a]pyrimidin-5-yl)acetamide) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 11.22 (s, 1H), 9.22 (d, J = 7.6 Hz, 1H), 8.76 (d, J = 1.5 Hz, 1H), 8.59 (d, J = 1.5 Hz, 1H), 8.06 (d, J = 7.8 Hz, 1H), 5.25-5.18 (m, 2H), 3.71 (q, J = 7.4 Hz, 2H), 2.17 (s, 3H), 1.21 (q , J = 7.5 Hz, 4H); ESI MS (m/z) 495.15 (MH)+. 70 2-(Ethylsulfonyl)-N-neopentyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1 ,5-a]pyrazin-7-amine (2-(ethylsulfonyl)-N-neopentyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.74 (d, J = 1.5 Hz, 1H), 8.56 (d, J = 1.5 Hz, 1H), 8.33 (d, J = 5.4 Hz, 1H), 8.20 (t, J = 7.0 Hz, 1H), 6.67 (d, J = 5.6 Hz, 1H), 5.24-5.17 (m, 2H), 3.79 (q, J = 7.4 Hz, 2H), 1.25 (t, J = 7.5 Hz, 3H), 0.95 (d, J = 14.9 Hz, 10H); ESI MS (m/z) 523.05 (MH)+. 71 2-(Ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7-(trifluoromethyl)pyrazolo[ 1,5-a] pyrimidine (2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7-(trifluoromethyl)pyrazolo[1,5- a] pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.14 (d, J = 1.5 Hz, 1H), 8.86 (d, J = 4.2 Hz, 1H), 8.57 (d, J = 1.5 Hz, 1H), 7.65 (d, J = 4.4 Hz, 1H), 5.19 (dd, J = 13.8, 12.8 Hz, 2H), 3.19 (q, J = 7.3 Hz, 2H), 1.39 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 474.00 (MH)+. 72 2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7-(trifluoromethyl)pyrazole And[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7-(trifluoromethyl)pyrazolo[1, 5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.01 (d, J = 4.2 Hz, 1H), 8.67 (d, J = 1.2 Hz, 1H), 8.65 (d, J = 1.5 Hz, 1H), 7.99 (d, J = 4.2 Hz, 1H), 5.24 (dd, J = 14.7, 13.7 Hz, 2H), 3.73 (q, J = 7.3 Hz, 2H), 1.25 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 506.10 (MH)+. 73 N-((5-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine -2-yl)(ethyl)(oxo)-l6-sulfinyl)nitrile amine (N-((5-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin -2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(oxo)-l6-sulfaneylidene)cyanamide) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.30 (d, J = 7.3 Hz, 1H), 8.89 (d, J = 1.5 Hz, 1H), 8.60 (d, J = 1.5 Hz, 1H), 7.48 (d, J = 7.3 Hz, 1H), 5.23 (t, J = 14.1 Hz, 2H), 4.30-4.19 (m, 2H), 2.40-2.37 (m, 1H), 1.32 (t, J = 7.3 Hz , 3H), 1.24-1.18 (m, 4H); ESI MS (m/z) 502.10 (MH)+. 74 2-(Ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine-7 (4H)-keto(2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidin-7(4H) -one) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 12.13 (s, 1H), 8.15 (d, J = 9.3 Hz, 1H), 7.85-7.83 (m, 1H), 7.57 (d, J = 9.3 Hz , 1H), 5.89 (d, J = 7.6 Hz, 1H), 5.31 (dd, J = 13.7, 12.7 Hz, 2H), 3.26 (t, J = 7.3 Hz, 2H), 1.37 (t, J = 7.3 Hz , 3H); ESI MS (m/z) 422.10 (MH)+. 75 2,7-bis(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a] Pyrimidine (2,7-bis(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6) δ 9.21 (d, J = 1.5 Hz, 1H), 8.51-8.50 (m, 2H), 7.13 (d, J = 4.9 Hz, 1H), 5.17 (dd , J = 13.8, 12.8 Hz, 2H), 3.29 (t, J = 3.7 Hz, 2H), 3.19 (q, J = 7.4 Hz, 2H), 1.44-1.37 (m, 6H); ESI MS (m/z ) 466.00 (MH)+. 76 (7-cyclopropyl-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine-2- Base)(ethyl)(imino)-l6-pyridine((7-cyclopropyl-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5 -a]pyrimidin-2-yl)(ethyl)(imino)-l6-sulfanone) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.66 (d, J = 4.6 Hz, 1H), 8.50 (d, J = 9.3 Hz, 1H), 7.59 (d, J = 9.3 Hz, 1H), 7.03 (d, J = 4.6 Hz, 1H), 5.35 (t, J = 13.6 Hz, 2H), 4.90 (s, 1H), 3.71-3.66 (m, 2H), 2.90-2.84 (m, 1H), 1.42 -1.38 (m, 2H), 1.35 (t, J = 7.3 Hz, 3H), 1.29-1.25 (m, 2H); ESI MS (m/z) 477.45 (MH)+. 77 2-(Ethylsulfonyl)-N-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1, 5-a]pyrazin-5-amine (2-(ethylsulfonyl)-N-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5- a]pyrimidin-5-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.87 (s, 1H), 8.65 (d, J = 7.6 Hz, 1H), 8.51 (d, J = 1.2 Hz, 1H), 8.07 (d, J = 4.6 Hz, 1H), 6.54 (d, J = 7.8 Hz, 1H), 5.22-5.15 (m, 2H), 3.75 (q, J = 7.4 Hz, 2H), 3.56 (s, 3H), 1.26-1.16 (m, 3H); ESI MS (m/z) 467.20 (MH)+. 78 2-(Ethylsulfonyl)-N-neopentyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1 ,5-a]pyrazin-5-amine (2-(ethylsulfonyl)-N-neopentyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a]pyrimidin-5-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.80 (s, 1H), 8.65 (d, J = 7.3 Hz, 1H), 8.51 (s, 1H), 7.97-7.93 (m, 1H), 6.68 (d, J = 7.6 Hz, 1H), 5.19 (t, J = 13.6 Hz, 2H), 3.75 (q, J = 7.1 Hz, 2H), 3.24 (d, J = 5.9 Hz, 2H), 1.23-1.18 (m, 3H), 0.93 (d, J = 10.0 Hz, 9H); ESI MS (m/z) 522.60 (MH)+. 79 2-(Ethylsulfonyl)-5-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1, 5-a] pyrimidine (2-(ethylsulfonyl)-5-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6) δ 6.72-6.81 (1H), 6.21-6.25 (1H), 6.09-6.13 (1H), 4.78-4.87 (1H), 2.65-2.83 (2H), 1.13 -1.32 (2H), 0.10-0.19 (3H), -1.32--1.19 (3H); ESI MS (m/z) 451.65 (MH)+. 80 ((2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a ]pyrimidin-5-yl)imino)dimethyl-l6-pyridine (((2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl )pyrazolo[1,5-a]pyrimidin-5-yl)imino)dimethyl-l6-sulfanone) ¹ H-NMR (400 MHz, DMSO- d 6) δ 8.87-8.92 (1H), 8.70-8.74 (1H), 8.51-8.55 (1H), 6.60-6.65 (1H), 5.07-5.26 (2H), 3.66 -3.76 (2H), 3.45-3.53 (6H), 1.12-1.27 (3H); ESI MS (m/z) 529.20 (MH)+. 81 2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-N-(2,2,2-tri Fluoroethyl)pyrazolo[1,5-a]pyrimidin-5-amine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl) -N-(2,2,2-trifluoroethyl)pyrazolo[1,5-a]pyrimidin-5-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.83 (d, J = 7.6 Hz, 1H), 8.77 (d, J = 1.5 Hz, 1H), 8.61 (t, J = 6.4 Hz, 1H), 8.53 (d, J = 1.5 Hz, 1H), 6.71 (d, J = 7.8 Hz, 1H), 5.19 (t, J = 14.1 Hz, 2H), 4.28 (td, J = 9.7, 6.2 Hz, 2H), 3.76 (q, J = 7.4 Hz, 2H), 1.21 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 535.00 (MH)+. 82 2-(Ethylsulfonyl)-N-isobutyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1 ,5-a]pyrazin-5-amine (2-(ethylsulfonyl)-N-isobutyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5 -a]pyrimidin-5-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.82 (d, J = 1.0 Hz, 1H), 8.65 (d, J = 7.6 Hz, 1H), 8.51 (d, J = 1.2 Hz, 1H), 8.09 (t, J = 5.1 Hz, 1H), 6.59 (d, J = 7.8 Hz, 1H), 5.19 (t, J = 13.9 Hz, 2H), 3.75 (q, J = 7.4 Hz, 2H), 3.19 ( t, J = 6.1 Hz, 2H), 1.98-1.89 (m, 1H), 1.22-1.16 (m, 3H), 0.93 (d, J = 6.6 Hz, 6H); ESI MS (m/z) 508.60 (MH )+. 83 2-(Ethylsulfonyl)-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)-3-(5-(2,2,3,3 ,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol -1-yl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.48 (d, J = 7.6 Hz, 1H), 8.74 (d, J = 1.5 Hz, 1H), 8.64 (d, J = 1.5 Hz, 1H), 7.87 (d, J = 7.6 Hz, 1H), 6.97 (s, 1H), 5.24 (t, J = 13.6 Hz, 2H), 3.80 (q, J = 7.3 Hz, 2H), 2.74 (s, 3H), 1.26 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 586.05 (MH)+. 84 2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-5-(1H-1,2,4 -Triazol-1-yl)pyrazol[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)- 5-(1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.60-9.56 (m, 2H), 8.87 (d, J = 1.5 Hz, 1H), 8.63 (d, J = 1.5 Hz, 1H), 8.46 (s , 1H), 7.85 (d, J = 7.6 Hz, 1H), 5.25 (t, J = 13.8 Hz, 2H), 3.81 (q, J = 7.3 Hz, 2H), 1.27-1.22 (m, 3H); ESI MS (m/z) 505.00 (MH)+. 85 2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-5-(3-(trifluoromethyl )-1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3 -pentafluoropropoxy)pyrazin-2-yl)-5-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6) δ 9.93 (d, J = 0.6 Hz, 1H), 9.64 (d, J = 7.6 Hz, 1H), 8.88 (d, J = 1.2 Hz, 1H), 8.65 (d, J = 1.2 Hz, 1H), 7.88 (d, J = 7.6 Hz, 1H), 5.25 (t, J = 13.4 Hz, 2H), 3.81 (q, J = 7.4 Hz, 2H), 1.26 ( t, J = 7.5 Hz, 3H); ESI MS (m/z) 572.40(MH)+. 86 ((2-(Ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a ]pyridazin-7-yl)imino)dimethyl-l6-pyridine (((2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl )pyrazolo[1,5-a]pyrimidin-7-yl)imino)dimethyl-l6-sulfanone) ¹ H-NMR (400 MHz, DMSO- d 6) δ 8.42 (d, J = 5.2 Hz, 1H), 8.27 (d, J = 9.2 Hz, 1H), 7.55-7.47 (m, 2H), 6.83 (d , J = 5.2 Hz, 1H), 5.34 (t, J = 13.4 Hz, 2H), 3.83 (q, J = 7.4 Hz, 2H), 3.70 (s, 6H), 1.23 (t, J = 7.5 Hz, 3H ); ESI MS (m/z) 529.00 (MH)+. 87 Ethyl((2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5 -a]pyrimidin-7-yl)imino)(methyl)-l6-sulfonyl(ethyl((2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin -3-yl)pyrazolo[1,5-a]pyrimidin-7-yl)imino)(methyl)-l6-sulfanone) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.41 (d, J = 5.1 Hz, 1H), 8.26 (d, J = 9.3 Hz, 1H), 7.53 (d, J = 9.0 Hz, 1H), 6.84 (d, J = 5.1 Hz, 1H), 5.37-5.30 (m, 2H), 3.86-3.79 (m, 4H), 3.64 (s, 3H), 1.41 (t, J = 7.3 Hz, 3H), 1.24 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 543.45 (MH)+. 88 Diethyl((2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1, 5-a]pyrimidin-7-yl)imino)-l6-sulfonyl(diethyl((2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3- yl)pyrazolo[1,5-a]pyrimidin-7-yl)imino)-l6-sulfanone) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.39 (d, J = 5.1 Hz, 1H), 8.25 (d, J = 9.3 Hz, 1H), 7.53 (d, J = 9.0 Hz, 1H), 6.84 (d, J = 5.1 Hz, 1H), 5.33 (t, J = 13.6 Hz, 2H), 3.84-3.77 (m, 6H), 1.38 (t, J = 7.3 Hz, 6H), 1.24 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 557.20 (MH)+. 89 N-(2-(Ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5- a] pyridazin-7-yl) acetamide (N-(2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5 -a]pyrimidin-7-yl)acetamide) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 11.21 (s, 1H), 8.70 (d, J = 5.1 Hz, 1H), 8.22 (d, J = 9.0 Hz, 1H), 7.94 (d, J = 5.1 Hz, 1H), 7.57 (d, J = 9.3 Hz, 1H), 5.39-5.32 (m, 2H), 3.86 (q, J = 7.3 Hz, 2H), 2.42 (s, 3H), 1.27 (t , J = 7.5 Hz, 3H); ESI MS (m/z) 495.10 (MH)+. 90 N-(2-(Ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5- a]pyrimidin-7-yl)cyclopropaneformamide (N-(2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1 ,5-a]pyrimidin-7-yl)cyclopropanecarboxamide) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 11.48 (s, 1H), 8.69 (d, J = 5.1 Hz, 1H), 8.22 (d, J = 9.3 Hz, 1H), 7.91 (d, J = 4.9 Hz, 1H), 7.57 (d, J = 9.3 Hz, 1H), 5.39-5.32 (m, 2H), 3.87 (q, J = 7.4 Hz, 2H), 2.63-2.58 (m, 1H), 1.28 (t, J = 7.5 Hz, 3H), 1.04-0.99 (m, 4H); ESI MS (m/z) 521.10 (MH)+. 91 2-(Ethylsulfonyl)-N-methyl-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1, 5-a] pyridazin-7-amine (2-(ethylsulfonyl)-N-methyl-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5- a] pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.48 (q, J = 4.8 Hz, 1H), 8.38 (d, J = 5.4 Hz, 1H), 8.31 (d, J = 9.3 Hz, 1H), 7.53 (d, J = 9.3 Hz, 1H), 6.44 (d, J = 5.4 Hz, 1H), 5.34 (dd, J = 13.8, 12.8 Hz, 2H), 3.86 (q, J = 7.4 Hz, 2H), 3.04 (d, J = 4.9 Hz, 3H), 1.24 (t, J = 7.5 Hz, 4H); ESI MS (m/z) 467.10 (MH)+. 92 2-(Ethylsulfonyl)-N-isopropyl-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1 ,5-a]pyridazin-7-amine (2-(ethylsulfonyl)-N-isopropyl-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5 -a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.36-8.31 (m, 1H), 8.28 (d, J = 9.3 Hz, 1H), 8.10 (s, 1H), 7.52 (d, J = 9.3 Hz , 1H), 6.58 (d, J = 6.1 Hz, 1H), 5.34 (dd, J = 13.7, 12.7 Hz, 2H), 4.07 (s, 1H), 3.89-3.82 (m, 2H), 1.34 (t, J = 3.3 Hz, 6H), 1.27-1.22 (m, 3H); ESI MS (m/z) 495.30 (MH)+. 93 2-(Ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-7-(pyrimidin-2-yl)pyridine Azolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-7-(pyrimidin-2-yl )pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.16 (t, J = 4.9 Hz, 2H), 9.00 (d, J = 4.4 Hz, 1H), 8.26 (d, J = 9.3 Hz, 1H), 7.81 (t, J = 4.9 Hz, 1H), 7.79 (d, J = 4.2 Hz, 1H), 7.61 (d, J = 9.3 Hz, 1H), 5.37 (t, J = 13.7 Hz, 2H), 3.77- 3.69 (m, 2H), 1.23 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 516.60 (MH)+. 94 2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7-(1H-1,2,4 -Triazol-1-yl)pyrazol[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)- 7-(1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 10.00 (s, 1H), 8.97 (d, J = 4.6 Hz, 1H), 8.75 (d, J = 1.5 Hz, 1H), 8.66 (d, J = 1.5 Hz, 1H), 8.63 (s, 1H), 7.90 (d, J = 4.6 Hz, 1H), 5.24 (t, J = 13.3 Hz, 2H), 3.85 (q, J = 7.4 Hz, 2H), 1.28 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 505.20 (MH)+. 95 2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)-7-(3-(trifluoromethyl )-1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3 -pentafluoropropoxy)pyrazin-2-yl)-7-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 10.12 (s, 1H), 9.02 (d, J = 4.6 Hz, 1H), 8.74 (s, 1H), 8.67 (s, 1H), 7.99 (d , J = 4.6 Hz, 1H), 5.25 (t, J = 13.8 Hz, 2H), 3.85 (q, J = 7.2 Hz, 2H), 1.27 (t, J = 7.3 Hz, 3H); ESI MS (m/ z) 573.05 (MH)+. 96 2-(Ethylsulfonyl)-7-(1-methyl-1H-pyrazol-5-yl)-3-(5-(2,2,3,3,3-pentafluoropropoxy) Pyrazin-2-yl)pyrazol[1,5-a]pyrimidine (2-(ethylsulfonyl)-7-(1-methyl-1H-pyrazol-5-yl)-3-(5-(2,2, 3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.91 (d, J = 4.3 Hz, 1H), 8.73 (d, J = 1.5 Hz, 1H), 8.64 (d, J = 1.5 Hz, 1H), 7.74 (d, J = 2.1 Hz, 1H), 7.63 (d, J = 4.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 5.24 (td, J = 13.8, 0.7 Hz, 2H), 3.96 (s, 3H), 3.73 (q, J = 7.3 Hz, 2H), 1.23 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 518.10 (MH)+. 97 N-cyclopropyl-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1 ,5-a]pyridazin-7-amine (N-cyclopropyl-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5 -a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.80 (s, 1H), 8.42 (d, J = 5.4 Hz, 1H), 8.27 (d, J = 9.3 Hz, 1H), 7.53 (d, J = 9.3 Hz, 1H), 6.66 (d, J = 5.4 Hz, 1H), 5.34 (t, J = 13.7 Hz, 2H), 3.84 (q, J = 7.4 Hz, 2H), 2.75 (t, J = 2.8 Hz, 1H), 1.24 (t, J = 7.3 Hz, 3H), 0.92-0.77 (m, 4H); ESI MS (m/z) 493.25 (MH)+. 98 2-(Ethylsulfonyl)-7-(1-methyl-1H-pyrazol-5-yl)-3-(6-(2,2,3,3,3-pentafluoropropoxy) Pyridazin-3-yl)pyrazol[1,5-a]pyrimidine (2-(ethylsulfonyl)-7-(1-methyl-1H-pyrazol-5-yl)-3-(6-(2,2, 3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.92 (d, J = 4.4 Hz, 1H), 8.24 (d, J = 9.3 Hz, 1H), 7.74 (d, J = 2.2 Hz, 1H), 7.65 (d, J = 4.4 Hz, 1H), 7.62-7.60 (m, 1H), 7.03 (d, J = 2.0 Hz, 1H), 5.37 (dd, J = 13.7, 12.7 Hz, 2H), 3.97 (s , 3H), 3.81 (q, J = 7.4 Hz, 2H), 1.24 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 518.35 (MH)+. 99 2-(ethylsulfonyl)-7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-3-(6-(2,2,3,3 ,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol -5-yl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.97 (d, J = 4.4 Hz, 1H), 8.24 (d, J = 9.3 Hz, 1H), 7.75 (d, J = 4.4 Hz, 1H), 7.63-7.60 (m, 1H), 7.46 (d, J = 0.5 Hz, 1H), 5.37 (t, J = 13.3 Hz, 2H), 4.04 (s, 3H), 3.81 (q, J = 7.4 Hz, 2H ), 1.24 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 586.50 (MH)+. 100 2-(ethylsulfonyl)-7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-3-(6-(2,2,3,3 ,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol -5-yl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyrazin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.96 (d, J = 4.2 Hz, 1H), 8.73 (d, J = 1.5 Hz, 1H), 8.65 (d, J = 1.5 Hz, 1H), 7.73 (d, J = 4.2 Hz, 1H), 7.45 (d, J = 0.5 Hz, 1H), 5.27-5.20 (m, 2H), 4.03 (s, 3H), 3.74 (q, J = 7.4 Hz, 2H ), 1.23 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 586.05 (MH)+. 101 2-(ethylsulfonyl)-7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-3-(6-(2,2,3,3 ,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine (2-(ethylsulfonyl)-7-(1-methyl-3-(trifluoromethyl)-1H-pyrazol -5-yl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.72 (d, J = 9.5 Hz, 1H), 8.46 (d, J = 5.4 Hz, 1H), 8.24 (d, J = 9.3 Hz, 1H), 7.54 (d, J = 9.0 Hz, 1H), 6.89 (d, J = 5.6 Hz, 1H), 5.35 (t, J = 13.8 Hz, 2H), 5.02 (d, J = 6.8 Hz, 1H), 3.86 ( q, J = 7.4 Hz, 2H), 1.58 (d, J = 6.8 Hz, 3H), 1.26 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 549.20 (MH)+. 102 7-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5- a]pyrimidine (7-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6) δ 8.48 (m, J = 4.6 Hz, 3H), 7.64 (d, J = 2.4 Hz, 1H), 6.72 (d, J = 8.8 Hz, 1H), 5.01 (t, J = 13.1 Hz, 2H), 3.35 (q, J = 7.4 Hz, 2H), 2.87-2.81 (m, 1H), 1.41-1.31 (m, 3H), 1.29-1.25 (m, 2H) , 1.24-1.21 (m, 2H); ESI MS (m/z) 509.75 (MH)+. 103 2-(Ethylsulfonyl)-7-(1-methyl-1H-pyrazol-5-yl)-3-(5-(2,2,3,3,3-pentafluoropropoxy) Pyridin-2-yl)pyrazol[1,5-a]pyrimidine (2-(ethylsulfonyl)-7-(1-methyl-1H-pyrazol-5-yl)-3-(5-(2,2,3 ,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.64 (d, J = 4.6 Hz, 1H), 8.51 (d, J = 2.4 Hz, 1H), 7.96 (d, J = 8.8 Hz, 1H), 7.68 (dd, J = 8.8, 3.2 Hz, 1H), 7.01 (d, J = 4.6 Hz, 1H), 5.03 (t, J = 13.1 Hz, 2H), 3.88 (q, J = 7.4 Hz, 2H), 2.89-2.83 (m, 1H), 1.42-1.37 (m, 2H), 1.29-1.21 (m, 5H); ESI MS (m/z) 477.25 (MH)+. 104 2-(Ethylsulfonyl)-7-(1-methyl-1H-pyrazol-5-yl)-3-(5-(2,2,3,3,3-pentafluoropropoxy) Pyridin-2-yl)pyrazol[1,5-a]pyrimidine (7-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl )pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.47-8.41 (m, 3H), 7.66 (dd, J = 8.8, 3.2 Hz, 1H), 7.53 (d, J = 4.4 Hz, 1H), 4.99 (dd, J = 13.6, 12.6 Hz, 2H), 3.21 (q, J = 7.4 Hz, 2H), 1.40 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 484.95 (MH)+. 105 (7-(tert-butylamino)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5-a] Pyrimidin-2-yl)(ethyl)(imino)-l6-pyridazin((7-(tert-butylamino)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3 -yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(imino)-l6-sulfanone) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.61 (d, J = 9.3 Hz, 1H), 8.36 (d, J = 5.6 Hz, 1H), 7.56 (d, J = 9.3 Hz, 1H), 7.05 (s, 1H), 6.74 (d, J = 5.6 Hz, 1H), 5.33 (t, J = 13.3 Hz, 2H), 4.97 (s, 1H), 3.83-3.72 (m, 2H), 1.55 (s , 9H), 1.33 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 508.50 (MH)+. 106 7-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5- a]pyrimidine (7-cyclopropyl-2-(ethylthio)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.60 (d, J = 4.4 Hz, 1H), 8.53-8.52 (m, 1H), 7.94 (dd, J = 8.8, 0.5 Hz, 1H), 7.86 (d, J = 4.4 Hz, 1H), 7.70 (dd, J = 8.8, 2.9 Hz, 1H), 5.04 (t, J = 13.1 Hz, 2H), 3.88 (q, J = 7.3 Hz, 2H), 1.25 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 516.85 (MH)+. 107 2-(Ethylsulfonyl)-N-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5 -a] pyridin-7-amine (2-(ethylsulfonyl)-N-methyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a ]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.47-8.46 (m, 1H), 8.37-8.35 (m, 2H), 8.03 (dd, J = 8.8, 0.5 Hz, 1H), 7.65 (dd, J = 8.8, 3.2 Hz, 1H), 6.39 (d, J = 5.6 Hz, 1H), 5.01 (t, J = 13.6 Hz, 2H), 3.90 (q, J = 7.4 Hz, 2H), 3.03 (d, J = 4.9 Hz, 3H), 1.23 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 466.10 (MH)+. 108 N-(tert-butyl)-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo [1,5-a]pyridazin-7-amine (N-(tert-butyl)-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl )pyrazolo[1,5-a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.47 (d, J = 2.4 Hz, 1H), 8.36 (d, J = 5.6 Hz, 1H), 8.02 (d, J = 8.8 Hz, 1H), 7.66 (dd, J = 8.8, 2.9 Hz, 1H), 6.87 (s, 1H), 6.72 (d, J = 5.6 Hz, 1H), 5.05-4.99 (m, 2H), 3.91 (q, J = 7.4 Hz , 2H), 1.55 (s, 9H), 1.25 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 508.10 (MH)+. 109 (7-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-2-yl )(ethyl)(imino)-l6-pyridine((7-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5- a]pyrimidin-2-yl)(ethyl)(imino)-l6-sulfanone) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.64 (d, J = 4.4 Hz, 1H), 8.53 (d, J = 2.4 Hz, 1H), 8.30 (dd, J = 8.8, 0.5 Hz, 1H ), 7.73-7.70 (m, 1H), 6.99 (d, J = 4.4 Hz, 1H), 5.07-5.00 (m, 3H), 3.71-3.65 (m, 2H), 2.87-2.81 (m, 1H), 1.40-1.35 (m, 5H), 1.31-1.22 (m, 3H); ESI MS (m/z) 476.45 (MH)+. 110 3-(7-Cyclopropyl-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-1-methyl-6-(2,2,3,3,3 -Pentafluoropropoxy)pyridin-2(1H)-one (3-(7-cyclopropyl-2-(ethylthio)pyrazolo[1,5-a]pyrimidin-3-yl)-1-methyl-6-( 2,2,3,3,3-pentafluoropropoxy)pyridin-2(1H)-one) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.28 (d, J = 4.4 Hz, 1H), 7.50 (d, J = 8.1 Hz, 1H), 6.61 (d, J = 4.4 Hz, 1H), 6.04 (d, J = 8.1 Hz, 1H), 5.07 (t, J = 12.6 Hz, 2H), 3.37 (d, J = 9.5 Hz, 3H), 3.10 (q, J = 7.3 Hz, 2H), 2.81- 2.77 (m, 1H), 1.32-1.28 (m, 5H), 1.22-1.16 (m, 2H); ESI MS (m/z) 475.55 (MH)+. 111 2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)-N-(2,2,2-trifluoro Ethyl)pyrazolo[1,5-a]pyrimidin-7-amine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)- N-(2,2,2-trifluoroethyl)pyrazolo[1,5-a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.79 (t, J = 6.9 Hz, 1H), 8.48-8.45 (m, 2H), 8.01 (d, J = 8.9 Hz, 1H), 7.66 (dd , J = 8.6, 3.1 Hz, 1H), 6.80 (d, J = 5.5 Hz, 1H), 5.02 (t, J = 13.0 Hz, 2H), 4.44-4.36 (m, 2H), 3.92 (q, J = 7.4 Hz, 2H), 1.24 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 534.05 (MH)+. 112 N-ethyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5 -a] pyridin-7-amine (N-ethyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a ]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.47 (d, J = 3.1 Hz, 1H), 8.36 (dd, J = 13.8, 5.8 Hz, 2H), 8.02 (d, J = 8.6 Hz, 1H ), 7.65 (dd, J = 8.9, 3.1 Hz, 1H), 6.48 (d, J = 5.5 Hz, 1H), 5.01 (t, J = 13.3 Hz, 2H), 3.91 (q, J = 7.3 Hz, 2H ), 3.53-3.47 (m, 2H), 1.24 (td, J = 7.3, 3.6 Hz, 6H); ESI MS (m/z) 479.90 (MH)+. 113 N-ethyl-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1, 5-a] pyridazin-7-amine (N-ethyl-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5- a] pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.50 (t, J = 6.4 Hz, 1H), 8.35 (d, J = 5.4 Hz, 1H), 8.30 (d, J = 9.0 Hz, 1H), 7.53 (d, J = 9.0 Hz, 1H), 6.54 (d, J = 5.6 Hz, 1H), 5.34 (t, J = 13.3 Hz, 2H), 3.86 (q, J = 7.4 Hz, 2H), 3.55- 3.48 (m, 2H), 1.24 (q, J = 7.3 Hz, 6H); ESI MS (m/z) 480.90 (MH)+. 114 (7-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidin-2-yl )(ethyl)(imino)-l6-pyridine((7-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5- a]pyrimidin-2-yl)(ethyl)(imino)-l6-sulfanone) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.57 (d, J = 4.4 Hz, 1H), 8.47 (d, J = 2.4 Hz, 1H), 7.81-7.79 (m, 1H), 7.64 (dd , J = 8.8, 2.9 Hz, 1H), 6.95 (d, J = 4.6 Hz, 1H), 5.06-4.99 (m, 2H), 3.82-3.70 (m, 2H), 2.88-2.83 (m, 1H), 2.56 (s, 3H), 1.41-1.36 (m, 2H), 1.23 (t, J = 7.3 Hz, 5H); ESI MS (m/z) 490.45 (MH)+. 115 N-ethyl-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1, 5-a] pyridazin-7-amine (N-ethyl-2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)pyrazolo[1,5- a] pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.32-8.28 (m, 4H), 7.52 (d, J = 9.3 Hz, 1H), 6.39 (d, J = 5.1 Hz, 1H), 5.37-5.30 (m, 2H), 3.86 (q, J = 7.4 Hz, 2H), 1.27-1.21 (m, 3H); ESI MS (m/z) 452.85 (MH)+. 116 N-((7-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidine- 2-yl)(ethyl)(oxo)-l6-sulfenyl)nitrile amine (N-((7-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin- 2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(oxo)-l6-sulfaneylidene)cyanamide) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.11 (d, J = 4.9 Hz, 2H), 8.80 (d, J = 4.2 Hz, 1H), 8.50-8.46 (m, 2H), 7.76 (t , J = 4.9 Hz, 1H), 7.68 (dd, J = 8.8, 3.2 Hz, 1H), 7.39 (d, J = 4.4 Hz, 1H), 5.03-4.97 (m, 2H), 2.98 (q, J = 7.3 Hz, 2H), 1.29 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 483.00 (MH)+. 117 N-((7-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a]pyrimidine- 2-yl)(ethyl)(oxo)-l6-sulfenyl)nitrile amine (N-((7-cyclopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin- 2-yl)pyrazolo[1,5-a]pyrimidin-2-yl)(ethyl)(oxo)-l6-sulfaneylidene)cyanamide) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.74 (d, J = 4.4 Hz, 1H), 8.53 (d, J = 3.2 Hz, 1H), 8.17 (d, J = 9.0 Hz, 1H), 7.75 (dd, J = 8.8, 2.9 Hz, 1H), 7.13 (d, J = 4.6 Hz, 1H), 5.05 (t, J = 13.4 Hz, 2H), 4.39 (dq, J = 25.0, 7.1 Hz, 2H ), 2.88-2.84 (m, 1H), 1.45-1.31 (m, 7H); ESI MS (m/z) 500.85 (MH)+. 118 2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)-7-(pyrimidin-2-yl)pyrazole And[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)-7-(pyrimidin-2-yl) pyrazolo[1,5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.16-9.14 (m, 2H), 8.96 (d, J = 4.2 Hz, 1H), 8.53 (d, J = 2.4 Hz, 1H), 7.99 (dd , J = 8.8, 0.5 Hz, 1H), 7.80 (t, J = 4.9 Hz, 1H), 7.74-7.71 (m, 2H), 5.05 (t, J = 13.1 Hz, 2H), 3.80 (q, J = 7.3 Hz, 2H), 1.21 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 514.80 (MH)+. 119 3-(7-cyclopropyl-2-(ethylsulfonyl-3-yl)pyrazolo[1,5-a]pyrimidinyl)-1-methyl-6-(2,2,3,3 ,3-Pentafluoropropoxy)pyridin-2(1H)-one(3-(7-cyclopropyl-2-(ethylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)-1-methyl-6 -(2,2,3,3,3-pentafluoropropoxy)pyridin-2(1H)-one) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.52 (d, J = 4.6 Hz, 1H), 7.55 (d, J = 8.3 Hz, 1H), 6.96 (d, J = 4.6 Hz, 1H), 6.08 (d, J = 7.9 Hz, 1H), 5.11 (t, J = 12.7 Hz, 2H), 3.54 (q, J = 7.4 Hz, 2H), 3.38-3.36 (m, 4H), 2.83-2.79 (m , 1H), 1.39-1.34 (m, 2H), 1.25-1.18 (m, 5H); ESI MS (m/z) 506.70 (MH)+. 120 N-cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1, 5-a] pyridin-7-amine (N-cyclopropyl-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5- a] pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.65 (s, 1H), 8.47-8.40 (m, 2H), 8.00 (dd, J = 8.8, 0.5 Hz, 1H), 7.65 (dd, J = 8.8, 3.2 Hz, 1H), 6.61 (d, J = 5.4 Hz, 1H), 5.01 (dd, J = 13.4, 12.5 Hz, 2H), 3.88 (q, J = 7.4 Hz, 2H), 2.74 (d, J = 1.5 Hz, 1H), 1.23 (t, J = 7.3 Hz, 3H), 0.91-0.76 (m, 4H); ESI MS (m/z) 491.90 (MH)+. 121 N-(cyclopropylmethyl)-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazole And[1,5-a]pyrimidin-7-amine (N-(cyclopropylmethyl)-2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl) pyrazolo[1,5-a]pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.47 (d, J = 2.4 Hz, 1H), 8.33 (d, J = 5.6 Hz, 1H), 8.04-8.02 (m, 1H), 7.65 (dd , J = 8.8, 3.2 Hz, 1H), 6.56 (d, J = 5.6 Hz, 1H), 5.01 (t, J = 13.1 Hz, 2H), 3.92 (q, J = 7.4 Hz, 2H), 3.35 (d , J = 7.1 Hz, 2H), 1.26-1.19 (m, 4H), 0.52-0.47 (m, 2H), 0.40-0.34 (m, 2H); ESI MS (m/z) 505.90 (MH)+. 122 2-(Ethylsulfonyl)-N-isopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1, 5-a] pyridin-7-amine (2-(ethylsulfonyl)-N-isopropyl-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5- a] pyrimidin-7-amine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.46 (d, J = 2.7 Hz, 1H), 8.34 (d, J = 5.4 Hz, 1H), 8.01 (d, J = 8.8 Hz, 1H), 7.92 (d, J = 8.8 Hz, 1H), 7.65 (dd, J = 8.8, 2.9 Hz, 1H), 6.52 (d, J = 5.6 Hz, 1H), 5.01 (t, J = 13.3 Hz, 2H), 4.09-4.02 (m, 1H), 3.91 (q, J = 7.4 Hz, 2H), 1.34 (d, J = 6.4 Hz, 6H), 1.24 (t, J = 7.3 Hz, 3H); ESI MS (m/ z) 493.95 (MH)+. 123 2-(Ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-7-(trifluoromethyl)pyrazolo[ 1,5-a]pyrimidine (2-(ethylthio)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-7-(trifluoromethyl)pyrazolo[1,5- a] pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.87 (d, J = 4.4 Hz, 1H), 8.71 (d, J = 9.3 Hz, 1H), 7.68 (d, J = 4.4 Hz, 1H), 7.55 (d, J = 9.3 Hz, 1H), 5.33 (dd, J = 13.7, 12.7 Hz, 2H), 3.20 (q, J = 7.3 Hz, 2H), 1.40 (t, J = 7.3 Hz, 3H); ESI MS (m/z) 474.00 (MH)+. 124 ((2-(Ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl)pyrazolo[1,5-a] Pyridin-7-yl)imino)dimethyl-l6-pyridin (((2-(ethylsulfonyl)-3-(5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl) pyrazolo[1,5-a]pyrimidin-7-yl)imino)dimethyl-l6-sulfanone) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 8.47 (d, J = 2.7 Hz, 1H), 8.40 (d, J = 5.1 Hz, 1H), 8.00-7.98 (m, 1H), 7.65 (dd , J = 8.8, 2.9 Hz, 1H), 6.78 (d, J = 5.1 Hz, 1H), 5.02 (t, J = 13.3 Hz, 2H), 3.87 (q, J = 7.4 Hz, 2H), 3.68 (s , 6H), 1.22 (t, J = 7.5 Hz, 3H); ESI MS (m/z) 527.85 (MH)+. 125 2-(Ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-7-(trifluoromethyl)pyrazole And[1,5-a]pyrimidine (2-(ethylsulfonyl)-3-(6-(2,2,3,3,3-pentafluoropropoxy)pyridazin-3-yl)-7-(trifluoromethyl)pyrazolo[1, 5-a]pyrimidine) ¹ H-NMR (400 MHz, DMSO- d 6 ) δ 9.02 (d, J = 4.2 Hz, 1H), 8.17 (d, J = 9.0 Hz, 1H), 8.01 (d, J = 4.2 Hz, 1H), 7.62 (d, J = 9.0 Hz, 1H), 5.41-5.34 (m, 2H), 3.79 (q, J = 7.4 Hz, 2H), 1.25 (q, J = 7.6 Hz, 3H); ESI MS (m/ z) 505.80 (MH)+. * Compound names were generated using Chemdraw Professional 19.1

As described herein, compounds of formula (I) have been shown to exert insecticidal activity against a variety of insects that attack important agricultural crops. The activity of the compounds of the invention was assessed by as described in the following assays:

Biological example:

example A : Tomato Moth ( Helicoverpa armigera )

Use the diet incorporation method, in which the required amount of test compound is weighed out and dissolved in a test tube containing a solvent solution. Place the tubes in a vortex at 2000 rpm for 90 min for proper mixing. When the temperature in the bioassay vessel is approximately 50 °C, add the semi-synthetic feed to this solution. Stir compound and feed well for proper mixing and allow to cool for 30 minutes. The solidified feed was cut into aliquots, and each aliquot was transferred to one of the cells of the bioassay tray. Release a single starved third instar larva into each cell of the bioassay tray and cover the assay tray with a lid. The bioassay trays were then maintained under laboratory conditions at a temperature of 25 °C and a relative humidity of 70%. Dead, moribund and surviving larvae were recorded 96 hours after larval release. The calculated percent mortality was obtained by combining the percent mortality of dead and dying larvae and comparing it to one of the untreated ones. The following compounds were reported to have a mortality rate greater than or equal to 70% at 300 ppm: 3, 5, 6, 16, 21, 43, 44, 45, 48, 52, 101, 103, 108, 120, and 121.

example B : Spodoptera litura ( Spodoptera litura )

The feed incorporation method is used, in which the required amount of the test compound is weighed and dissolved in a test tube containing a solvent solution. Place the tubes in a vortex at 2000 rpm for 90 min for proper mixing. When the temperature in the bioassay vessel is approximately 50 °C, add the semi-synthetic feed to this solution. Stir compound and feed well for proper mixing and allow to cool for 30 minutes. The solidified feed was cut into aliquots, and each aliquot was transferred to one of the cells of the bioassay tray. Release a single starved third instar larva into each cell of the bioassay tray and cover the assay tray with a lid. The bioassay trays were then maintained under laboratory conditions at a temperature of 25 °C and a relative humidity of 70%. Dead, moribund and surviving larvae were recorded 96 hours after larval release. The calculated percent mortality was obtained by combining the percent mortality of dead and dying larvae and comparing it to one of the untreated ones. The following compounds were reported to have a mortality rate greater than or equal to 70% at 300 ppm: 3, 4, 5, 14, 16, 21, 43, 45, 48, 52, 70, 72, 103, 116, 119, and 121.

example C : diamondback moth ( Plutella xylostella )

Tests are performed using the leaf dip method, in which the desired amount of compound is weighed and dissolved in a test tube containing a solvent solution. The tubes were placed in a vortex at 2000 rpm for 90 minutes for proper mixing and then diluted to the desired assay concentration with 0.01% Triton-X solution. Immerse cabbage leaves in the compound solution for 10 s, dry in the shade for 20 min, and transfer to the cells of the bioassay tray. Release a single starved second instar larvae into each cell of the bioassay tray and cover the assay tray with a lid. The bioassay trays were then maintained under laboratory conditions at a temperature of 25 °C and a relative humidity of 70%. Dead, moribund and surviving larvae were recorded 72 hours after larval release. The calculated percent mortality was obtained by combining the percent mortality of dead and dying larvae and comparing it to one of the untreated ones. The following compounds were reported to have a mortality rate greater than or equal to 70% at 300 ppm: 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 33, 36, 39, 40, 42, 43, 44, 45, 46, 48, 49, 51, 52, 54, 55, 57, 58, 59, 60, 61, 63, 64, 68, 69, 70, 71, 72, 73, 75, 76, 77, 79, 81, 84, 86, 87, 88, 89, 90, 91, 92, 93, 94, 96, 97, 98, 100, 101, 102, 103, 105, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124 and 125.

example D. : Bemisia tabaci ( Bemisia tabaci )

Tests are performed using the leaf dip method, in which the desired amount of compound is weighed and dissolved in a test tube containing a solvent solution. The tubes were placed in a vortex at 2000 rpm for 90 minutes for proper mixing and then diluted to the desired assay concentration with 0.01% Triton-X solution. Eggplant (brinjal) leaves were immersed in the compound solution for 10 seconds, dried in the shade for 20 minutes, and then placed with the abaxial side of the leaves facing up in an atmosphere containing 4 mL of solidified 1% agaric-agaric solution. Cover the hole container. Known numbers of newly hatched adult whitefly were collected by a modified aspirator and released into a perforated container with a lid containing the treated leaf. Store containers in a plant growth chamber at 25 °C and 70% relative humidity. Dead, moribund and surviving adults were recorded 72 hours after adult release. The calculated percent mortality was obtained by combining the percent mortality of dead and dying adults and comparing it to one of the untreated ones. The following compounds were reported to have a mortality rate greater than or equal to 70% at 300 ppm: 52, 108 and 119.

example E. : Peach aphid ( Myzus persicae )

Tests are performed using the leaf dip method, in which the desired amount of compound is weighed and dissolved in a test tube containing a solvent solution. The tubes were placed in a vortex at 2000 rpm for 90 minutes for proper mixing and then diluted to the desired assay concentration with 0.01% Triton-X solution. Pepper (capsicum) leaves were immersed in the compound solution for 10 seconds, dried in the shade for 20 minutes, and then placed with the abaxial side up on the bioassay plates each containing 4 mL of solidified 1% agar-agar solution. A known number of third instar nymphs were collected in Petri dishes and released into units with treated leaves covered with perforated lids for better ventilation. Store the assay trays in a plant growth chamber at 25 °C and 70% relative humidity. Dead, moribund and surviving nymphs were recorded 72 hours after nymph release. The calculated percent mortality was obtained by combining the percent mortality of dead and dying nymphs and comparing it to one of the untreated ones. The following compounds were reported to have a mortality rate greater than or equal to 70% at 300 ppm: 3, 6, 12, 13, 15, 20, 23, 27, 43, 46, 48, 52, 58, 59, 72, 76, 86, 93, 96, 103, 110, 114, 116, 118, 119 and 124.

example f : Brown rice lice ( Nilaparvata lugens )

Tests are performed using the seedling dip method, in which the desired amount of compound is weighed and dissolved in a test tube containing a solvent solution. The tubes were placed in a vortex at 2000 rpm for 90 minutes for proper mixing and then diluted to the desired assay concentration with 0.01% Triton-X solution. Rice (paddy) seedlings were immersed in the compound solution for 10 seconds, dried in the shade for 20 minutes, and then the seedlings were placed in glass test tubes and the roots were kept in water. Fifteen third instar nymphs were released into each test tube and the tubes were stored in a plant growth chamber at 25 °C and 75% relative humidity. Dead, moribund and surviving nymphs were recorded 72 hours after nymph release. The calculated percent mortality was obtained by combining the percent mortality of dead and dying nymphs and comparing it to one of the untreated ones. The following compounds were reported to have a mortality rate greater than or equal to 70% at 300 ppm: 3, 6, 12, 13, 21, 23, 24, 28, 29, 43, 52, 58, 59, 76, 93, 108 and 109.

While the invention has been described in terms of certain preferred embodiments, other embodiments will be apparent to those of ordinary skill in the art to which the subject matter pertains in view of the specification. It will be apparent to those of ordinary skill in the art that various modifications in the materials and methods can be made without departing from the scope of the invention.

Claims (19)

A compound of formula (I),

Formula (I) wherein, R ¹ is selected from C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ The group consisting of -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl and C ₃ -C ₈ -cycloalkyl-C ₁ -C ₆ -alkyl; Y is independently selected from O or NR ^Y ; ^RY is selected from the group consisting of hydrogen, nitrile, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl, The group consisting of C ₂ -C ₄ -haloalkenyl, C ₃ -C ₅ -cycloalkyl and C ₃ -C ₅ -cycloalkyl-C ₁ -C ₃ -alkyl; A represents N or CR ² ; G ¹ and G ² represent N or C; when both G are not nitrogen at the same time; R ² is selected from hydrogen, halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -ene C ₂ -C ₆ -alkynyl, C _{1 -C} 6 -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) _2. P(=O)(OR'') ₂ , Si(R'') ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl The group formed; wherein each aliphatic group can be optionally substituted by one or more R ^2a groups, and the ring group of R ² can be optionally substituted by one or more R ^2b groups; R ^2a is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ - C ₈ -cycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ = NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , Si(R′′) ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -group consisting of heterocyclyl; R ^2b is selected from halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ - C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 The group consisting of R ⁷ , C(=O)R ⁸ , Si(R′′) ₃ , S(O) _0-1 R ⁹ =NR ¹⁰ and N=S(O) _0-1 (R ⁹ ) ₂ or two R ^2a or two R ^2b substituents form a three to seven membered ring with the atom to which they are attached or together with other atoms selected from the group consisting of C, N, O and S, and optionally comprising 1 to 3 ring members selected from the group consisting of C(=O), C(=S), S(O) _0-2 and Si(R') ₂ ), the part of the three to seven membered ring may be substituted by one or more R ^2ab groups; R ^2ab is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl , C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , NR ⁵ R ⁶ , S( O) _0-2 R ⁷ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , Si(R′′) ₃ , C ₆ -C ₁₀ - A group consisting of aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; Q represents a six-membered heterocyclic ring, which may optionally be replaced by one or more R ³ groups Substitution; R ³ is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ^8. S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , P(=O)(OR′′) ₂ , Si(R′′) ₃ , The group consisting of C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; wherein each aliphatic group may optionally be replaced by one or more R ^3a group, R ³ ring group can be optionally substituted by one or more R ^3b groups; R ^3a is selected from halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ - C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , Si(R′ ') ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ^3b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -Alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkane base, OR ⁴ , C(R′′) ₂ =NR ⁵ R ⁶ , C(R′′) ₂ -OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , Si(R′′) ₃ , C ₆ -C ₁₀ -A group consisting of aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; or two R ^3a or two R ^3b are formed with the atom to which they are attached or together with other atoms Three to seven membered rings, the other atoms are selected from the group consisting of C, N, O and S, and optionally contain 1 to 3 atoms selected from the group consisting of C(=O), C(=S), S(O) _m and Si(R'') ₂ ring members of the group consisting of, the part of the three to seven member ring can be substituted by one or more R ^3ab groups; wherein R ^3ab is selected from hydrogen , halogen, nitrile, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , NR ⁵ R ⁶ and S(O) _0-2 The group formed by R ⁷ ; Z represents direct bond (direct bond) or O; Ring E represents five or six membered heterocyclic rings fused with ring D; wherein the ring E is selectively replaced by one or more R ¹¹ Substituted by the group; R ¹¹ is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -halogenyl base, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(= O)R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , P(=O)(OR′′) ₂ , Si(R′′ ) ₃ , the group consisting of C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; wherein each aliphatic group can be optionally replaced by one or Multiple R ^11a groups are substituted, and the ring group of R ¹¹ can be optionally substituted by one or more R ^11b groups; R ^11a is selected from halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , Si(R ′′) ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ^11b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -Alkyl, C ₂ -C ₆ -Alkenyl, C ₂ -C ₆ -Alkynyl, C ₁ -C ₆ -Haloalkyl, C ₂ -C ₆ -Haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , C(R′′) ₂ -NR ⁵ R ⁶ , C(R′′) ₂ -OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _{0 -2} R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , Si(R′′) ₃ , C The group consisting of ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ⁴ is selected from the group consisting of hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, S(O ) ₂ R ⁷ , the group consisting of Si(R′′) ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; wherein each aliphatic The group group can be optionally substituted by R ^4a group, and the ring group of R ⁴ can be optionally substituted by one or more R ^4b groups; R ^4a is selected from the group consisting of halogen, nitrile, C ₁ - C ₆ -Alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C(=O)R', Si(R'') ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C The group consisting of ₃ -C ₁₀ -heterocyclyl; R ^4b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl , C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R ′, C(=O)R′, Si(R′′) ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl Group; R ⁵ is selected from hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , NR′R′′, S(O) _0-2 R ⁷ , C(=O)R ⁸ , Si(R′′) ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -arylalkyl and C ₃ -C ₁₀ -heterocyclyl group; wherein each aliphatic group can optionally be replaced by R ^5a group Substituted, the ring group of R ⁵ can be optionally substituted by one or more R ^5b groups; R ^5a is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ - Alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R ′, C(=O)R′, Si(R′′) ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl Group; R ^5b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', Si(R'') ₃ , C(= O) the group consisting of R', C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ⁶ is selected from the group consisting of hydrogen, C ₁ -C ₆ -Alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₁ -C ₆ -cyclo A group consisting of alkyl and C(=O)R ⁸ ; or R ⁵ and R ⁶ and the atoms to which they are attached or together with other atoms may form a four to seven membered ring selected from the group consisting of Group: C, N, O, C(=O), C(=S), S(O) _0-2 and Si(R'') ₂ , the part of the four to seven membered non-aromatic ring is optionally replaced by a or multiple R'groups; R ⁷ is selected from C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -halogenyl base, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, NR ⁵ R ⁶ , C The group consisting of ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; wherein each aliphatic group can optionally be replaced by one or more R ^7a The ring group of R ⁷ can be optionally substituted by one or more R ^7b groups; R ^7a is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _{0- 2} The group consisting of R', C(=O)R', C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ^7b is selected from Free halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -halogen Alkenyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C(=O)R', C ₆ -C ₁₀ -aryl, The group consisting of C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ⁸ is selected from the group consisting of hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , NR ⁵ R ⁶ , N=S (O) _0-1 (R ⁹ ) ₂ , the group consisting of C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; wherein each aliphatic The group can be optionally substituted by one or more R ^8a groups, and the ring group of R ⁸ can be optionally substituted by one or more R ^8b groups; R ^8a is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR'' , NR′R′′, S(O) _0-2 R′, C(=O)R′, C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ - The group consisting of heterocyclyl; R ^8b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C(=O )R', C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -arane The group consisting of radical and C ₃ -C ₁₀ -heterocyclyl; R ⁹ is selected from the group consisting of C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C The group consisting of ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₆ -cycloalkyl and C(=O)R ⁸ ; R ¹⁰ is selected from the group consisting of hydrogen, nitrile C ₁ -C ₆ -alkyl, C _{2 -C} 6 -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -Cycloalkyl, Si(R'') ₃ , S(O) _0-2 R ⁷ and C(=O)R ⁸ group consisting of; two R ₉ substituents or R ₉ and The R ₁₀ substituent forms a four to seven membered ring with the atom to which it is attached or together with other atoms selected from the group consisting of C, N, O and S, optionally containing 1 to 3 Ring members selected from the group consisting of C(=O), C(=S), S(O) _0-2 , and Si(R'') ₂ , portions of the four to seven membered rings may be replaced by one or more Substituted by R'groups;R' is selected from R'', OR'', N(R'') ₂ , S(O) _0-2 R'', C(=O)R'', C The group consisting of (=O)OR'' and C(=O)N(R'') ₂ ; R'' is selected from the group consisting of hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkene The group consisting of radical, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl and C ₃ -C ₈ -cycloalkyl; wherein each R'' can be optionally substituted by halogen; Each of R ¹ to R ¹¹ , R ^2a , R ^2b , R ^2ab , R ^3a , R ^{3b , R 3ab , R 4a , R 4b , R 5a , R 5b} , R ^7a , ^{R 7b ,} R ^8a , and R ^8b The group can be optionally represented by one or more groups selected from halogen, nitrile, R'', OR'', SR'', N(R'') ₂ , COOR'' and CON(R'') ₂ Substituted by a group consisting of groups; m is an integer from 0 to 2; or an agrochemically acceptable salt, stereoisomer, isomorph, metal complex or N-oxide. The compound of formula (I) as claimed in item 1, wherein the compound of formula (I) is represented by the compound of formula (I-1);

Formula (I-1) wherein, R ¹ is C ₁ -C ₆ -alkyl or C ₃ -cycloalkyl; Y is NR ^Y or O; ^RY is selected from hydrogen, nitrile, C ₁ -C ₄ - Alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl, C ₂ -C ₄ -haloalkenyl, C ₃ -C ₅ -cycloalkyl and the group consisting of C ₃ -C ₅ -cycloalkyl-C ₁ -C ₃ -alkyl; Z represents a direct bond or O; Q represents a six-membered heterocyclic ring, which may optionally be surrounded by one or more R ³ group is substituted; R ³ is selected from halogen, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, C ₁ -C ₆ - The group consisting of haloalkoxy, S(O) _0-2 , C ₁ -C ₆ -haloalkyl, -S(O) _0-1 R ⁹ =NR ¹⁰ and C ₃ -C ₁₀ -heterocyclyl Group; wherein the C ³ _{-C 10} -heterocyclic group of R 3 can be optionally substituted by one or more R ^3b groups; R ^3b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -haloalkoxy, S(O) _0-2 C ₁ -C ₆ -alkyl and S(O) _0-2 C ₁ -C ₆ - The group consisting of haloalkyl; R ¹¹ is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , -S(O) _0-1 R ⁹ =NR ¹⁰ , -N=S(O) _0-1 (R ⁹ ) ₂ , -P(=O)(OR′′) _2. The group consisting of Si(R'') ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclic; wherein each aliphatic group It can be optionally substituted by one or more R ^11a groups, and the ring group of R ¹¹ can be optionally substituted by one or more R ^11b groups; R ^11a is selected from halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , CR' ′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , Si(R'')3, C _{6 -C10} -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ^11b is selected from the group consisting of halogen, nitrile C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , C(R′′) ₂ -NR ⁵ R ⁶ , C(R′′) ₂ -OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S( O) _0-2 R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , Si(R′′) _3. The group consisting of C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ⁴ is selected from hydrogen, C ₁ -C ₆ -alk C ₂ -C ₆ -alkenyl, C _{2 -C} 6 -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, The group consisting of S(O) ₂ R ⁷ , Si(R′′) ₃ , phenyl, benzyl and C ₃ -C ₁₀ -heterocyclyl; wherein each aliphatic group can be optionally replaced by R ^4a group, the ring group of R ⁴ can be optionally substituted by one or more R ^4b groups; R ^4a is selected from halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ - C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _{0 -2} R', C(=O)R', Si(R'') ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl The group consisting of; R ^4b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkane radical, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C(=O)R', Si(R'') ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ⁵ is selected from the group consisting of hydrogen, C ₁ -C ₆ -Alkyl, C ₂ -C ₆ -Alkenyl, C ₂ -C ₆ -Alkynyl, C ₁ -C ₆ -Haloalkyl, C ₂ -C ₆ -Haloalkenyl, C ₃ -C ₈ -Cycloalkyl, OR ⁴ , NR′R′′, S(O) _0-2 R ⁷ , C(=O)R ⁸ , Si(R′′) ₃ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aryl The group consisting of C ₃ -C ₁₀ -heterocyclic group; wherein each aliphatic group can be optionally substituted by R ^5a group, and the ring group of R ⁵ can be optionally replaced by one or more R ^5b group is substituted; R ^5a is selected from halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ - Haloalkyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C(=O)R', Si(R'') ₃ , The group consisting of C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ^5b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ - Alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl , OR'', NR'R'', S(O) _0-2 R', Si(R'') ₃ , C(=O)R', C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -Aralkyl and C ₃ -C ₁₀ -heterocyclyl group; R ⁶ is selected from hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C The group consisting of ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₁ -C ₆ -cycloalkyl and C(=O)R ⁸ ; or R ⁵ and R form ^a four to seven membered ring with the atom to which they are attached or together with other atoms selected from the group consisting of: C, N, O, C(=O), C(=S) , S(O) _0-2 and Si(R'') ₂ , part of the four to seven-membered non-aromatic ring is selectively substituted by one or more R'groups; R ⁷ is selected from C ₁ -C ₆ -Alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cyclo The group consisting of alkyl, NR ⁵ R ⁶ , C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; wherein each aliphatic group can be selected is optionally substituted by one or more R ^7a groups, and the ring group of R ⁷ can be optionally substituted by one or more R ^7b groups; R ^7a is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -Alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -Haloalkyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C(=O)R', C ₆ -C ₁₀ -aryl The group consisting of C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ^7b is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C(=O)R', C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl The group consisting of; R ⁸ is selected from hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR'', NR ⁵ R ⁶ , N=S(O) _0-1 (R ⁹ ) ₂ , C ₆ -C ₁₀ - The group consisting of aryl, C ₇ -C ₁₄ -arylalkyl and C ₃ -C ₁₀ -heterocyclyl; wherein each aliphatic group is optionally substituted by one or more R ^8a groups, The ring group of R ⁸ can be optionally substituted by one or more R ^8b groups; R ^8a is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C (=O)R', C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ -aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ^8b is selected from the group consisting of halogen, nitrile , C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR'', NR'R'', S(O) _0-2 R', C(=O)R', C ₆ -C ₁₀ -aryl, C ₇ -C ₁₄ - the group consisting of aralkyl and C ₃ -C ₁₀ -heterocyclyl; R ⁹ is selected from the group consisting of C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkyne The group consisting of C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₆ -cycloalkyl and C(=O)R ⁸ ; R ¹⁰ is selected from Hydrogen, Nitrile, C ₁ -C ₆ -Alkyl, C ₂ -C ₆ -Alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, Si(R′′) ₃ , S(O) _0-2 A group formed by R ⁷ and C(=O)R ⁸ ; two R ₉ or R ₉ and R ₁₀ form a four to seven-membered ring with the atoms they are connected to or with other atoms, and the other atoms are selected from Free from the group consisting of: C, N, O, C(=O), C(=S), S(O) _0-2 and Si(R'') ₂ , the part of the four to seven membered ring can be Substituted by one or more R'groups;R' is selected from the group consisting of R'', OR'', N(R'') ₂ , C(=O)R'', C(=O)OR'' and the group consisting of C(=O)N(R'') ₂ ; R'' is selected from the group consisting of hydrogen, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -A group consisting of alkynyl, C ₁ -C ₆ -haloalkyl and C ₃ -C ₈ -cycloalkyl; wherein each R'' can be optionally substituted by halogen; m is an integer from 0 to 2 ; or stereoisomers and salts thereof. The formula (I) compound as described in claim item 1 or 2, wherein Q is selected from Q1, Q2 or Q3,

,

or

and R ³ and R ⁵ are as defined in Claim 1. The formula (I) compound as described in claim item 3, wherein Q1, Q2 or Q3Q are selected from Q1a, Q1b, Q1c, Q1d, Q1e, Q2a, Q2b, Q2c, Q2d, Q2e, Q2f, Q2g, Q3a, Q3b, Q3c, Q3d, Q3e, Q3f or Q3g,

. The compound of formula (I) as claimed in claim 3, wherein Q1, Q2 or Q3Q is selected from Q1a, Q1d, Q1e, Q2a, Q2c, Q3a, Q3b, Q3c or Q3f. The formula (I) compound as described in claim item 1 or 2, wherein R ³ is selected from halogen, -S(O) _0-2 C ₁ -C ₆ -haloalkyl, C ₁ -C ₄ haloalkyl and C ₁ -C ₄ haloalkoxy. The compound of formula (I) as claimed in item 1 or 2, wherein R ¹¹ is selected from halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₁ -C ₆ - Haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, C ₃ -C ₈ -cyanocycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , S(O) _0-1 R ⁹ =NR ¹⁰ , N=S(O) _0-1 (R ⁹ ) ₂ , phenyl, A group consisting of four to six membered heterocyclic groups; wherein R ¹¹ is selectively substituted by F, Cl, CN, methyl or methoxy. The compound of formula (I-1) as described in claim item 2, wherein: R ¹ is C ₁ -C ₄ -alkyl; Z represents a direct bond or O; Q is selected from Q1a, Q1d, Q1e, Q2a, Q2c , Q3a, Q3b, Q3c or Q3f; R ³ is selected from halogen, -S(O) _0-2 C ₁ -C ₄ -haloalkyl, -S(O)(NR ^Y )C ₁ -C ₆ -halogen Alkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy; R ¹¹ is selected from the group consisting of halogen, nitrile, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C _{1 -C} 6 -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, OR ⁴ , CR′′=NR ⁵ , NR ⁵ R ⁶ , S(O) _0-2 R ⁷ , C(=O)R ⁸ , -S(O) _0-1 R ⁹ =NR ¹⁰ , -N=S(O) _0-1 (R ⁹ ) _2. (Un)substituted phenyl or (un)substituted four to six-membered heterocyclic group; R ⁵ is selected from hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -C ₈ -cycloalkyl, (un)substituted phenyl or (un)substituted C ₃ -C ₁₀ -heterocyclyl; R ⁶ is selected from hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -cycloalkyl or C(=O)R ⁸ ; and R ⁸ is selected from C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl or C ₃ -C ₈ -cycloalkyl; R ⁷ is selected from C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl, NR ⁵ R ⁶ , ( Un)substituted phenyl, (un)substituted benzyl or (un)substituted four to six membered heterocyclyl; R ⁹ is selected from C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl , C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl and C ₃ -C ₈ -cycloalkyl; R ¹⁰ is selected from The group consisting of hydrogen, nitrile, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -cycloalkyl and C(=O)R ⁸ . The compound of formula (I-1) as described in Claim 2, wherein R ¹¹ is selected from CHF ₂ , CF ₃ , CH ₂ CF ₃ , -NHCH ₂ CH ₃ , -N(CH ₃ )CH ₂ CH ₃ , - NH(C(CH ₃ ) ₃ ), -N(CH ₃ )(C(CH ₃ ) ₃ ), -N(CH ₃ )COCH ₃ , -N(CH ₃ )CO(cyclopropyl), -N= S(O)(CH ₃ ) ₂ , cyclopropyl, 3-chloro-pyrazol-1-yl (3-chloro-pyrazol-1-yl), 3-trifluoromethyl-pyrazol-1-yl ( 3-trifluoromethyl-pyrazol-1-yl), 1,2,4-triazol-1-yl (1,2,4-triazol-1-yl), pyrimidin-2-yl (pyrimidin-2-yl), Pyridazin-2-yl (pyridazyn-2-yl) or pyridazin-3-yl (pyridazyn-3-yl); wherein R ¹¹ is optionally substituted by F, Cl, CN, methyl or methoxy . A composition comprising the compound of formula (I) as described in Claim 1 or its agronomically acceptable salt, stereoisomer, isomorph or N-oxide, and at least one selected from surfactants and auxiliary Additional ingredient of the group consisting of agents. The composition as claimed in item 10, wherein said composition further comprises at least one selected from fungicides, insecticides, nematocides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics , fertilizer or nutrient bioactive compatible compounds. The composition according to claim 10, wherein the compound of formula (I) accounts for 0.1-99 wt% of the total weight of the composition, preferably accounts for 5-50 wt% of the total weight of the composition. A composition comprising a biologically effective amount of the compound of formula (I) as described in Claim 1, and at least one selected from fungicides, insecticides, nematocides, acaricides, biological insecticides, herbicides , plant growth regulators, antibiotics, fertilizers and nutrients bioactive compatible compounds. A method for controlling insects and acarid pests, comprising: causing the insects and the acarid pests, their habitats, breeding grounds, food supplies, plants, seeds, soil, areas, materials or the insects and the acarid pests to be The environment that grows or may grow, or the material, plant, seed, soil, surface or space that is protected from pest attack or infestation and the formula (I) compound, salt, stereotype as described in claim 1 or 10 or 13 Isomers, allomorphs, metal complexes, N-oxide compositions, or combinations thereof. A method for protecting crops from attacking or infesting by insects and acarid pests, comprising: making the crops with the compound of formula (I), salt, stereoisomer, isomorph as described in claim 1 or 10 or 13 , metal complexes, N-oxide compositions or combinations thereof. The method according to claim 14 or 15, wherein said method comprises applying an effective dose of the compound of formula (I) to agricultural or horticultural crops, and the amount is 1 gai to 5000 gai per hectare. A method of protecting seeds, plants and plant parts from soil insects and protecting seedling roots and shoots from soil and foliar insects, comprising: before sowing and/or after pre-germination, making the seeds with the same as claim 1 Or the compound of formula (I) described in 10 or 13, salts, stereoisomers, isomers, metal complexes, N-oxide compositions or combinations thereof are contacted. A use of a compound of formula (I), salt, N-oxide, isomer, isomorph, composition or combination thereof as described in Claim 1 or 10 or 13, which is used to control crops and horticultural crops , insect and mite pests in household and vector control, and parasites on animals. A kind of seed, comprising formula (I) compound or salt, metal complex, N-oxide, stereoisomer, allomorph, composition or combination thereof as described in claim 1 or 10 or 13, wherein the The amount of the compound of formula (I) in the seed is from about 0.0001 wt% to about 1 wt%.