Bicyclic heteroaromatic compounds and their use as pest control agents - Patents.com

Abstract

The present invention discloses N-substituted bicyclic heteroaromatic compounds of formula (I). JPEG2024546050000097.jpg2833 Formula (I) In the formula, R, R 1 , R 2 , R 4、 W 1 , W 2 , A and Het are as defined in the detailed description. The present invention further discloses methods for preparing the compounds of formula (I) and methods for using the compounds of formula (I) as pesticides.

Description

[Technical field]

[0001] The present invention relates to compounds of formula (I). More particularly, the present invention relates to N-substituted bicyclic heteroaromatic compounds of formula (I) and methods for their preparation. The present invention further relates to compositions containing these compounds and their use as pest control agents. [Background technology]

[0002] Invertebrate pests, especially arthropods and nematodes, destroy growing and harvested crops, thereby causing serious economic losses to the food supply. Similarly, insects also attack wooden houses and commercial structures, causing similarly large economic losses to property. Therefore, there is a continuous need for new agents to combat invertebrate pests such as insects, arachnids and nematodes. Modern insecticides and acaricides currently available must meet many requirements, for example, regarding activity level, long-term efficacy, breadth of insecticidal spectrum, environmental and toxicological safety, and additional beneficial effects, as well as their usability. Over the past decades, efforts have been made to develop selective insecticides that act specifically on biochemical modes of action present only in insects or mites, but which, in addition, exhibit properties that differ in an advantageous way from known insecticides.

[0003] Fused bicyclic heteroaromatic compounds having insecticidal activity are known in the prior art, for example, in Patent Documents 1-5. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] International Publication No. 2007 / 115647 [Patent Document 2] International Publication No. 2012 / 136751 [Patent Document 3] International Publication No. 2014 / 076272 [Patent Document 4] International Publication No. 2020 / 025658 [Patent Document 5] International Publication No. 2020 / 011808 Summary of the Invention [Problem to be solved by the invention]

[0005] However, there remains a continuing need for new compounds that are more effective, less toxic, environmentally safer, and / or have different mechanisms of action in combating invertebrate pests.

[0006] Surprisingly, it has now been found that N-substituted bicyclic heteroaromatic compounds of formula (I) have advantages over the prior art, for example by exhibiting improved insecticidal activity.

[0007] In view of the above, the present invention contemplates such compounds which satisfy or overcome the shortcomings associated with the prior art. Surprisingly, it has now been found that certain novel insecticidally active N-substituted bicyclic heteroaromatic compounds which are the subject of the present invention possess favorable properties as insecticides and are desirably environmentally safe. [Means for solving the problem]

[0008] The present invention provides N-substituted bicyclic heteroaromatic compounds of formula (I) or a salt, stereoisomer, metal complex, polymorph or N-oxide thereof: [ka] Formula (I) In the formula, R, R 1 , R 2 , R 4、 W 1 , W 2 , A and Het are as defined in the detailed description.

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

[0010] In another embodiment, the present invention provides a composition for controlling or preventing invertebrate pests comprising a biologically effective amount of a compound of formula (I) or a salt, stereoisomer, metal complex, polymorph, or N-oxide thereof, and at least one additional component selected from the group consisting of surfactants and adjuvants.

[0011] In yet another embodiment, the composition further comprises at least one additional biologically active and compatible compound selected from a fungicide, an insecticide, a nematicide, an acaricide, a biopesticide, a herbicide, a plant growth regulator, an antibiotic, a fertilizer, or a nutrient.

[0012] In yet another embodiment, the present invention provides the use of a compound of formula (I) or its salts, stereoisomers, metal complexes, polymorphs, or N-oxides, compositions or combinations thereof for combating invertebrate pests in agricultural and horticultural crops and parasites in animals or wooden residential and commercial structures.

[0013] In yet another embodiment, the present invention provides a method of combating invertebrate pests comprising contacting a biologically effective amount of a compound of formula (I) or its salts, stereoisomers, metal complexes, polymorphs, or N-oxides thereof, as well as compositions or combinations thereof, with the invertebrate pests, their habitat, breeding grounds, food supply, plants, seeds, soil, areas, materials or environments, or materials, plants, seeds, soil, surfaces or spaces to be protected from pest attack or infestation. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] <Definition> The definitions provided herein for terms used in this disclosure are for illustrative purposes only and are not intended to limit the scope of the inventions disclosed in this disclosure.

[0015] As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having," "contains," "characterized by," or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitations expressly stated. For example, a composition, mixture, method, or process that includes a list of elements is not necessarily limited to only those elements, but can include other elements not expressly listed or inherent to such composition, mixture, method, or process.

[0016] The transitional phrase "consisting of" excludes any unspecified element, step, or ingredient. When recited in a claim, it closes the claim to include materials other than those recited, except for impurities ordinarily associated therewith. When the term "consisting of" appears in a clause in the body of a claim rather than immediately following the preamble, it limits only the elements recited in that clause and does not exclude other elements from the claim as a whole.

[0017] The transitional phrase "consisting essentially of" is used to define a composition or method that includes materials, steps, features, components or elements in addition to those literally disclosed, provided that these additional materials, steps, features, components or elements do not materially affect the basic and novel characteristics of the claimed invention. The term "consisting essentially of" sits intermediate between "comprises" and "consisting of."

[0018] Further, unless expressly stated to the contrary, "or" refers to an inclusive "or" and not an exclusive "or." For example, condition A "or" B is when A is true (or exists) and B is false (or does not exist), when A is false (or does not exist) and B is true (or exists), or when both A and B are true (or exist).

[0019] Also, the indefinite articles "a" and "an" preceding an element or component of the invention are intended to be open ended with regard to the number of instances (i.e., occurrences) of that element or component. Thus, "a" or "an" should be read to include one or at least one, and the singular form of an element or component also includes the plural, unless the number is clearly implied to be singular.

[0020] As referred to in this disclosure, the term "invertebrate pests" includes arthropods, gastropods and nematodes that are economically important as pests. The term "arthropods" includes insects, mites, spiders, scorpions, centipedes, millipedes, pillbugs and symphylans. The term "gastropods" includes snails, slugs and other stem worms. The term "nematodes" refers to living organisms of the phylum Nematoda. The term "helminths" includes roundworms, filarial worms, phytophagous nematodes (Nematoda), trematodes (Tematoda), acanthocephalans and tapestries (Cestoda).

[0021] The term "agronomic" refers to the production of field crops such as for food, feed and fiber, and includes the growing of corn, soybeans and other legumes, rice, grains (e.g., wheat, oats, barley, rye, rice, corn), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, peppers, eggplant, canola, melons), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome fruits, stone fruits, citrus fruits), small fruits (berries, cherries), and other specialty crops (e.g., canola, sunflowers, olives).

[0022] The term "non-agronomic" refers to crops other than field crops, such as horticultural crops (e.g., greenhouse plants, nursery plants, ornamental plants not grown outdoors), residential, agricultural, commercial and industrial structures, turf (e.g., turf farms, pastures, golf courses, lawns, sports fields), wood products, storage, forestry agriculture and vegetation management, public health (i.e., humans) and animal health (e.g., domestic animals such as pets, livestock, poultry, non-domestic animals such as wildlife) uses, etc.

[0023] Nonagronomic applications include protecting animals from invertebrate parasitic pests by administering to the animal to be protected a parasiticidal effective amount (i.e., biologically effective) of the compounds of the present invention, typically in the form of a veterinary formulated composition. As referred to in this disclosure and claims, the terms "parasiticidal" and "parasiticidal" refer to an observable effect on invertebrate parasitic pests to protect the animal from the pest. A parasiticidal effect typically relates to reducing the occurrence or activity of the target invertebrate parasitic pest. Such effects on pests include death, growth retardation, reduced mobility or reduced ability to persist on or within the host animal, reduced feeding, and inhibition of reproduction. These effects on invertebrate parasitic pests provide control (including prevention, reduction, or elimination) of infestation or infection of the animal.

[0024] The compounds of the present disclosure may exist in pure form or as a mixture of different possible isomeric forms, such as stereoisomers. The various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, and geometric isomers. Any desired mixture of these isomers is within the scope of the claims of the present disclosure. Those skilled in the art will understand that one stereoisomer may be more active and / or exhibit beneficial effects when enriched with respect to the other isomers or separated from the other isomers. Furthermore, those skilled in the art will know the processes or methods or techniques to separate, enrich, and / or selectively prepare said isomers.

[0025] Here, the meaning of various terms used in the specification will be explained.

[0026] The term "enantiomerically enriched" refers to a chiral substance whose enantiomeric ratio is greater than 50:50 and less than 100:0. As used herein, the term "aliphatic compound" or "aliphatic group" refers to an organic compound in which carbon atoms are linked in straight chains, branched chains, or non-aromatic rings.

[0027] The term "alkyl" used alone or in compound words such as "alkylthio" or "haloalkyl" or -N(alkyl) or alkylcarbonylalkyl or alkylsulfonylamino, means any straight or branched chain C1-C 10 It includes alkyl, preferably C1-C8 alkyl, more preferably C1-C6 alkyl, and most preferably C1-C4 alkyl. Representative examples of alkyl include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl, or isomers thereof. When alkyl is at the terminal of a composite substituent, the terminal portion of the composite substituent, e.g., cycloalkyl, may be mono- or polysubstituted, identically or differently and independently, by alkyl, such as, for example, alkylcycloalkyl. The same applies to composite substituents terminated by other radicals, e.g., alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy, etc.

[0028] As used herein, the term "cyanoalkyl" refers to an alkyl group having 1 to 10 carbon atoms ("C1-C 10 "C1-C6-cyanoalkyl" refers to a straight or branched alkyl group having 1 to 6 ("C1-C6-cyanoalkyl") carbon atoms (as described above), preferably wherein 1 or 2, preferably 1, of the hydrogen atoms of these groups are replaced with a cyano (CN) group. Non-limiting examples are cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 2-cyanopropyl, 3-cyanopropyl, 1-cyanobutyl, 2-cyanobutyl, 3-cyanobutyl, 4-cyanobutyl, and the like.

[0029] The term "alkenyl" used alone or in combination means straight or branched chain C2-C 10-alkenes, preferably C2-C8-alkenes, more preferably C2-C6-alkenes, and most preferably C2-C4-alkenes.Representative examples of alkenes include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl nyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-di, 3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3 2-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl and different isomers."Alkenyl" also includes polyenes, such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl as part of a compound substituent, such as, for example, haloalkenyl, unless otherwise defined.

[0030] The term "alkynyl" used alone or in compound words means straight or branched C2-C 10 -alkynes, preferably C2-C8-alkynes, more preferably C2-C6-alkynes, and most preferably C2-C4-alkynes. Non-limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3- The term "alkynyl" includes pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 3-methyl-4-pentynyl, 3-methyl-, 1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl, as well as different isomers. This definition also applies to alkynyl as part of a complex substituent, such as haloalkynyl, unless otherwise specified. The term "alkynyl" can also include moieties that consist of multiple triple bonds, such as 2,5-hexadiynyl.

[0031] As used herein, the term "cycloalkyl" refers to an alkyl group having 3 to 10 carbon atoms (C 10"-cycloalkyl" refers to an alkyl closed to form a ring group having carbon atoms. Preferably C3-C8-cycloalkyl, more preferably C3-C6-cycloalkyl. Non-limiting examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as part of a composite substituent, such as cycloalkylalkyl, unless otherwise specifically defined.

[0032] "Bicycloalkyl" or "bicyclic alkyl" means a saturated or partially unsaturated fused, spiro or bridged bicyclic ring assembly. In certain embodiments, "bicycloalkyl" represented alone or along with another radical, includes any of the following radicals: (C4-C 15 ) Bicycloalkyl, (C4-C 10 ) Bicycloalkyl, (C6-C 10 )bicycloalkyl or (C8-C 10 )bicycloalkyl. Alternatively, "bicycloalkyl," either alone or represented along with another radical, can be a (C7)bicycloalkyl, a (C8)bicycloalkyl or a (C 10 ) bicycloalkyl.

[0033] The term "cycloalkenyl" refers to an alkenyl that is closed to form a ring containing a monocyclic partially unsaturated hydrocarbyl group. Non-limiting examples include, but are not limited to, cyclopropenyl, cyclopentenyl, and cyclohexenyl. This definition also applies to cycloalkenyl as part of a compound substituent, such as cycloalkenylalkyl, unless otherwise specifically defined elsewhere.

[0034] The term "cycloalkynyl" refers to an alkynyl closed to form a ring, including a monocyclic partially unsaturated group. Non-limiting examples include, but are not limited to, cyclopropynyl, cyclopentynyl, and cyclohexynyl. This definition also applies to cycloalkynyl as part of a compound substituent, such as cycloalkynylalkyl, unless otherwise specifically defined elsewhere.

[0035] The terms "cycloalkoxy", "cycloalkenyloxy", etc. are similarly defined. Non-limiting examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy, and cyclohexyloxy. This definition also applies to cycloalkoxy as part of a compound substituent, such as cycloalkoxyalkyl, unless specifically defined elsewhere.

[0036] As used herein, the term "cyanocycloalkyl" refers to a cycloalkyl group having 3 to 10 carbon atoms ("C 10 "-cyanoalkyl" refers to an alkyl (as described above) closed to form a ring group having carbon atoms, where one or two, preferably one, of the hydrogen atoms of these groups are replaced by a cyano (CN) group. Non-limiting examples include 1-cyanocyclopropyl, 2-cyanocyclopropyl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 1-cyanocyclopentyl, 2-cyanocyclopentyl, 3-cyclopentyl, 4-cyclopentyl, 1-cyanohexyl, 2-cyanohexyl, 3-cyanocyclohexyl, 4-cyanocyclohexyl, and the like.

[0037] The term "halogen", alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. Furthermore, when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Non-limiting examples of "haloalkyl" include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro-2,2,2 trifluoroethyl, and 1,1,1-trifluoroprop-2-yl. This definition also applies to haloalkyl as part of a compound substituent, such as haloalkylaminoalkyl, unless specifically defined elsewhere.

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

[0039] The term "haloalkoxy" refers to a straight or branched chain alkoxy group, in which some or all of the hydrogen atoms may be replaced with halogen atoms as described above. Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2-trichloroethoxy, pentafluoroethoxy, and 1,1,1-trifluoroprop-2-oxy. This definition also applies to haloalkoxy, such as haloalkoxyalkyl, as part of a compound substituent, unless specifically defined elsewhere.

[0040] The term "haloalkylthio" refers to a straight or branched chain alkylthio group, some or all of the hydrogen atoms of which may be replaced with halogen atoms as described above. Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethylthio and 1,1,1-trifluoroprop-2-ylthio. This definition also applies to haloalkylthio as part of a compound substituent, such as haloalkylthioalkyl, unless otherwise defined.

[0041] Non-limiting examples of "haloalkylsulfinyl" include CF3S(O), CCl3S(O), CF3CH2S(O) and CF3CF2S(O). Examples of "haloalkylsulfonyl" include CF3S(O), CCl3S(O), CF3CH2S(O) and CF3CF2S(O).

[0042] The term "hydroxy" means -OH, amino means -NRR, where R may be any available substituent such as H or alkyl, carbonyl means -C(O)-, carbonyloxy means -OC(O)-, sulfinyl means SO, sulfonyl means S(O)2, nitro means -NO2, and cyano means -CN.

[0043] The term "alkoxy", used alone or in compound words, means C1-C 10 Alkoxy includes, preferably, C1-C8 alkoxy, more preferably, C1-C6 alkoxy, and most preferably, C1-C4 alkoxy. Examples of alkoxy include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, and 3-methylpentoxy. , 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,3-dimethylbutoxy, 1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy as well as the different isomers. This definition also applies to alkoxy as part of a compound substituent, such as haloalkoxy, alkynylalkoxy, etc., unless otherwise specifically defined.

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

[0045] The term "alkoxyalkoxy" denotes an alkoxy substitution on an alkoxy.

[0046] The term "(alkylsulfanyl: S-alkyl)" as used herein refers to a straight or branched chain saturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, and more preferably 1 to 4 carbon atoms, attached via a sulfur atom. The term "alkylthio" includes branched or straight chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 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 the different isomers.

[0047] Halocycloalkyl, halocycloalkenyl, alkylcycloalkyl, halocycloalkylalkyl, cycloalkylalkyl, cycloalkoxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylcarbonyl, cycloalkylcarbonyl, haloalkoxylalkyl, and the like are defined as in the above examples.

[0048] The term "alkylthioalkyl" denotes alkylthio substitution on alkyl. Representative examples of "alkylthioalkyl" include -CH2SCH2, -CH2SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and CH3CH2SCH2CH2. "Alkylthioalkoxy" denotes alkylthio substitution on alkoxy. The term "cycloalkylalkylamino" denotes cycloalkyl substitution on alkylamino.

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

[0050] The term "alkoxycarbonyl" refers to an alkoxy group attached to the backbone via a carbonyl group (-CO-). This definition also applies to alkoxycarbonyl as part of a compound substituent, such as cycloalkylalkoxycarbonyl, unless otherwise specifically defined.

[0051] The term "alkylsulfoxyl (S(=O)-alkyl)" as used herein refers to a straight or branched saturated alkyl group (as described above) of 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms (C1-C6-alkylsulfinyl), more preferably 1 to 4 carbon atoms, bonded at any position of the alkyl group via the sulfur atom of the sulfinyl group. Non-limiting examples of "alkylsulfinyl" include methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 1-methylpentylsulfinyl, The term "arylsulfonyl" includes 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2 trimethylpropylsulfinyl, 1,2,2 trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl and different isomers. The term "arylsulfonyl" includes Ar-S(O), where Ar may be any carbocyclic or heterocyclic ring. This definition also applies to alkylsulfinyl as part of a compound substituent, such as haloalkylsulfinyl, unless otherwise specifically defined.

[0052] The term "alkylsulfonyl" (S(=O)2-alkyl), as used herein, refers to a linear or branched saturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms (C1-C6-alkylsulfonyl), preferably 1 to 4 carbon atoms, bonded at any position of the alkyl group via the sulfur atom of the sulfonyl group. Non-limiting examples of "alkylsulfonyl" include methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 1-methylpentylsulfonyl, The term "arylsulfonyl" includes 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2 trimethylpropylsulfonyl, 1,2,2 trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl as well as different isomers. The term "arylsulfonyl" includes Ar-S(O)2, where Ar may be any carbocyclic or heterocyclic ring. This definition also applies to alkylsulfonyl as part of a compound substituent, such as alkylsulfonylalkyl, unless otherwise defined.

[0053] "Alkylamino", "dialkylamino", etc. are defined similarly to the above examples.

[0054] The term "aryl" as used herein refers to a group that includes any carbon-based aromatic group, including, but not limited to, phenyl, naphthalene, biphenyl, anthracene, and the like. Aryl groups may be substituted or unsubstituted. Furthermore, aryl groups may be a single ring structure, or may be fused ring structures or may include multiple ring structures that are linked through one or more bridging groups, such as carbon-carbon bonds.

[0055] The term "aryl" also includes "aralkyl" and refers to an aryl hydrocarbon radical containing an alkyl portion as defined above. Examples include benzyl, phenylethyl, and 6-naphthylhexyl. The term "aralkenyl" as used herein refers to an aryl hydrocarbon radical containing an alkenyl portion as defined above and an aryl portion as defined above. Examples include styryl, 3-(benzyl)prop-2-enyl, and 6-naphthylhex-2-enyl.

[0056] The term "hetero" in reference to a ring refers to a ring in which at least one ring atom is not carbon and which can contain from 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, provided that each ring contains no more than 4 nitrogens, no more than 2 oxygens, and no more than 2 sulfurs.

[0057] The term "aromatic" indicates that the Huckel rule is satisfied, and the term "non-aromatic" indicates that the Huckel rule is not satisfied.

[0058] The terms "heterocycle", "heterocyclic", or "heterocyclic ring system" include "aromatic heterocycles" or "heteroaryl bicyclic ring systems", where the rings may be aromatic or non-aromatic, and "non-aromatic heterocyclic ring systems" or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds, where a heterocycle is an N, O, S(O) ring. 0~2 and / or the C ring members of the heterocycle can be replaced by C(=O), C(=S), C(=CR*R*) and C=NR*, where * indicates an integer.

[0059] The term "non-aromatic heterocycle" or "non-aromatic heterocycle" refers to a 3-15-membered, preferably 3-12-membered, saturated or partially unsaturated heterocycle containing 1-4 heteroatoms from the group oxygen, nitrogen and sulfur, and includes monocyclic, bicyclic or tricyclic heterocycles containing, in addition to the carbon ring members, 1-3 nitrogen atoms and / or 1 oxygen or sulfur atom, or 1-2 oxygen and / or sulfur atoms, and in the case where the ring contains multiple oxygen atoms, they are not directly adjacent. For example, oxiranyl, oxetanyl, aziridinyl, azetidinyl, thietanyl, thietanyl 1-oxide, thietanyl 1,1-dioxide, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 6-isoxazolidinyl, 7-isoxazolidinyl, 8-isoxazolidinyl, 9-isoxazolidinyl, 10-isoxazolidinyl, 11-isoxazolidinyl, 12-isoxazolidinyl, 13-isoxazolidinyl, 14-isoxazolidinyl, 15-isoxazolidinyl, 16-isoxazolidinyl, 17-isoxazolidinyl, 18-isoxazolidinyl, 19-isoxazolidinyl, 20-isoxazolidinyl, 21-isoxazolidinyl, 22-isoxazolidinyl, 23-isoxazolidinyl, 24-isoxazolidinyl, 25-isoxazolidinyl, 26-isox lysinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 1-imidazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1 ,2,4-Oxadiazolidin-3-yl, 1,2,4-Oxadiazolidin-5-yl, 1,2,4-Thiadiazolidin-3-yl, 1,2,4-Thiadiazolidin-5-yl, 1,2,4-Triazolidin-5-yl, 1,2,4-Triazolidin-1-yl, 1,2,4-Triazolidin-3-yl, 1,3,4-Oxadiazolidin-2-yl, 1,3,4-Thiadiazolidin-2-yl , 1,3,4-triazolidin-1-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-thiazolidin-2-yl, 1,3,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-Dihydrothien-3-yl, pyrrolinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2, 3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, pyrazinyl, morpholinyl, thiomorpholinyl, 1,3-Dioxan-5-yl, 2-Tetrahydropyranyl, 4-Tetrahydropyranyl, 2-Tetrahydrothienyl, 3-Hexahydropyridazinyl, 4-Hexahydropyridazinyl, 2-Hexahydropyrimidinyl, 4-Hexahydropyrimidinyl, 5-Hexahydropyrimidinyl, 2-Piperazinyl, 1,3,5-Hexahydrotriazin-2-yl, 1,2,4-Hexahydrotriazin-3-yl, Cycloserine, 2,3,4,5-Tetrahydro[1H] Azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,4,7-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,6,7-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl hexahydroazepin-1- or -2- or -3- or -4-yl, tetra- and hexahydrooxepinyl, for example 2,3,4,5-tetrahydro[1H]oxepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,4,7-tetrahydro[1H]oxepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,6,7-tetrahydro[1H]oxepin-2- or -3- or -4- or -5- or -6- or -7-yl, Examples of heterocyclic groups include, but are not limited to, hexahydroazepin-1- or -2- or -3- or -4-yl, tetra- and hexahydro-1,3-diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl, tetra- and hexahydro-1,3-dioxepinyl, and tetra- and hexahydro-1,4-dioxepinyl. This definition also applies to heterocyclyl as part of a compound substituent, such as heterocyclylalkyl, unless otherwise defined elsewhere.

[0060] The term "heteroaryl" or "aromatic heterocyclic" means a 5- or 6-membered fully unsaturated monocyclic ring system containing 1 to 4 heteroatoms from the group oxygen, nitrogen, and sulfur, and if the ring contains more than one oxygen atom, they are not directly adjacent; a 5-membered heteroaryl containing 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur or oxygen atom; a 5-membered heteroaryl group which may contain 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur or oxygen atom as ring members in addition to carbon atoms. Examples include, but are not limited to, furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,3,4-triazolyl, tetrazolyl, nitrogen-linked 5-membered heteroaryl containing 1 to 4 nitrogen atoms, or benzofused nitrogen-linked 5-membered heteroaryl containing 1 to 3 nitrogen atoms, 5-membered heteroaryl groups which may contain 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms as ring members in addition to the carbon atoms, and in which two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member may be bridged by a buta-1,3-diene-1,4-diyl group in which one or two carbon atoms may be replaced by a nitrogen atom. wherein these rings are attached to the backbone via one of the nitrogen ring members and include, but are not limited to, 1-pyrrolyl, 1-pyrazolyl, 1,2,4 triazol-1-yl, 1-imidazolyl, 1,2,3 triazol-1-yl and 1,3,4 triazol-1-yl.

[0061] 6-membered heteroaryl containing 1 to 4 nitrogen atoms includes, but is not limited to, 6-membered heteroaryl groups that can contain, in addition to carbon atoms, 1 to 3 and 1 to 4 nitrogen atoms as ring members, respectively, such as pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, and 1,2,4,5-tetrazin-3-yl. Benzo-fused 5-membered heteroaryl containing 1 to 3 nitrogen atoms or 1 nitrogen atom and 1 oxygen atom or sulfur atom is, for example, indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, indazol-1-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl, indazol-7-yl, indazol-2-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1-benzothiophen-6-yl, 1-benzothiophen-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl and 1,3-benzoxazol-7-yl.Benzofused 6-membered heteroaryl containing 1 to 3 nitrogen atoms includes, but is not limited to, for example, quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, and isoquinolin-8-yl. This definition also applies to heteroaryl as part of a compound substituent, such as heteroarylalkyl, unless otherwise defined.

[0062] The term "trialkylsilyl" includes three branched and / or straight chain alkyl groups linked by bonds to a silicon atom, such as trimethylsilyl, triethylsilyl, and t-butyl-dimethylsilyl. "Halotrialkylsilyl" indicates that at least one of the three alkyl groups is partially or fully substituted with halogen atoms, which may be the same or different. The term "alkoxytrialkylsilyl" indicates that at least one of the three alkyl groups is substituted with one or more alkoxy groups, which may be the same or different. The term "trialkylsilyloxy" indicates a trialkylsilyl moiety attached via an oxygen.

[0063] Non-limiting examples of "alkylcarbonyl" include C(O)CH3, C(O)CH2CH2CH3 and C(O)CH(CH3). Non-limiting examples of "alkoxycarbonyl" include CH3OC(=O), CH3CH2OC(=O), CH3CH2CH2OC(=O), (CH3)2CHOC(=O) and the different butoxy- or pentoxycarbonyl isomers. Non-limiting examples of "alkylaminocarbonyl" include CH3NHC(=O), CH3CH2NHC(=O), CH3CH2CH2NHC(=O), (CH3)2CHNHC(=O) and the different butylamino- or pentylaminocarbonyl isomers. Non-limiting examples of "dialkylaminocarbonyl" include (CH3)2NC(=O), (CH3CH2)2NC(=O), CH3CH2(CH3)NC(=O), CH3CH2CH2(CH3)NC(=O), and (CH3)2CHN(CH3)C(=O). Non-limiting examples of "alkoxyalkylcarbonyl" include CH3OCH2C(=O), CH3OCH2CH2C(=O), CH3CHOCH2C(=O), CH3CH2CH2CH2OCH2C(=O), and CH3CHOCH2CH2C(=O). Non-limiting examples of "alkylthioalkylcarbonyl" include CHSCHC(=O), CHSCHCHC(=O), CHCHSCHC(=O), CHCHCHCHSCHC(=O) and CHCHSCHCHC(=O). The terms "haloalkylsulfonylaminocarbonyl", "alkylsulfonylaminocarbonyl", "alkylthioalkoxycarbonyl", "alkoxycarbonylalkylamino", and the like are similarly defined.

[0064] Non-limiting examples of "alkylaminoalkylcarbonyl" include CH3NHCH2C(=O), CH3NHCH2CH2C(=O), CH3CH2NHCH2C(=O), CH3CH2CH2CH2NHCH2C(=O) and CH3CH2NHCH2CH2C(=O).

[0065] The term "amide" refers to A-R'C=ONR''-B, where R' and R'' represent substituents and A and B represent optional groups.

[0066] The term "thioamide" refers to A-R'C=SNR''-B, where R' and R'' represent substituents and A and B represent optional groups.

[0067] The term "(Halo)C i ~C j -Cycloalkyl-C i ~C j -alkyl" is C i ~C j -Cycloalkyl-C i ~C j -Alkyl or C i ~C j -Cycloalkyl-C i ~C j -Alkyl optionally contains one or more halogens, e.g., C i ~C j -Halocycloalkyl-C i ~C j -Alkyl, C i ~C j -Cycloalkyl-C i ~C j -Haloalkyl, C i ~C j -Halocycloalkyl-C i ~C j -haloalkyl. i ~C j -Cycloalkyl-C i ~C j Examples of "-alkyl" include, but are not limited to, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, chlorocyclopropylmethyl, cyclopropyl-chloromethyl, chlorocyclopropyl-chloromethyl, chlorocyclopropylethyl, and cyclopropylchloroethyl.

[0068] The total number of carbon atoms in the substituent is "C i ~Cj」 The alkyl groups are represented by the prefixes i and j, where i and j are numbers from 1 to 21. For example, C1-C3 alkylsulfonyl means methylsulfonyl to propylsulfonyl, C2 alkoxyalkyl means CH3OCH2, and C3 alkoxyalkyl means, for example, CH3CH(OCH 3) , CH3OCH2CH2 or CH3CHOCH2, and C4 alkoxyalkyl refers to the various isomers of alkyl groups substituted with alkoxy groups containing a total of 4 carbon atoms, including, for example, CH3CH2CH2OCH2 and CH3CHOCH2CH2. In the above description, when the compound of formula (I) contains one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

[0069] When a compound is substituted with a substituent having a subscript indicating that the number of said substituents may be more than one, said substituents (if more than one) are independently selected from the group of defined substituents. m When the subscript m represents an integer in the range of, for example, 0 to 4, the number of substituents may be selected from integers in the range of 0 to 4.

[0070] If a group contains a substituent which may be hydrogen, then the group is recognized as being unsubstituted if the substituent is hydrogen.

[0071] The term "optionally substituted" is used interchangeably herein with the phrase "substituted or unsubstituted." Unless otherwise indicated, an optionally substituted group may have a substituent at each substitutable position of the group, and each substitution is independent of the others. An optionally substituted group may have no substituents. Thus, the phrase "optionally substituted with one or more substituents" means that the number of substituents may vary from 0 to the number of positions available for substitution.

[0072] The embodiments of the present specification and various features and advantageous details thereof are described in the description with reference to non-limiting embodiments. Descriptions of well-known components and processing techniques are omitted so as not to unnecessarily obscure the embodiments of the present specification. The examples used in the present specification are intended only to facilitate the understanding of how the embodiments of the present specification can be implemented and to enable those skilled in the art to implement the embodiments of the present specification. Therefore, the examples should not be interpreted as limiting the scope of the embodiments of the present specification.

[0073] The description of the specific embodiments will fully clarify the general nature of the embodiments of the present specification, so that others can easily modify and / or adapt such specific embodiments to various applications by applying current knowledge without departing from the general concept. Therefore, such adaptations and modifications should be and are intended to be understood within the meaning and range of equivalents of the disclosed embodiments. It should be understood that the terms or terms used in the present specification are for the purpose of description and not for the purpose of limitation. Thus, although the embodiments of the present specification have been described in terms of preferred embodiments, those skilled in the art will recognize that the embodiments of the present specification can be modified and implemented within the spirit and scope of the embodiments described herein.

[0074] Any discussion of documents, acts, materials, devices, articles or the like which has been included in the present specification is solely for the purpose of providing a context for the disclosure and is not to be construed as an admission that any or all of such matters form part of the prior art base or were common general knowledge in the art relevant to the disclosure as they existed prior to the priority date of this application.

[0075] The numerical values ​​given in the specification and in the specification / claims may form an important part of the invention, but any deviation from such numerical values ​​is within the scope of the invention, provided that the deviation is in accordance with the same scientific principles as those of the invention disclosed in the present invention. The compounds of the invention of the present invention can exist as mixtures of different possible isomers, in particular E and Z, threo and erythro stereoisomers, and optical isomers, where appropriate, but also tautomers. Both E and Z isomers, as well as threo and erythro isomers, and optical isomers, any desired mixtures of these isomers and possible tautomers are disclosed and claimed.

[0076] For purposes of this disclosure, the term "pest" includes, but is not limited to, fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, insects, and rodents, and is an animal or plant that is harmful to humans or human concerns, including crops, livestock, and forestry.

[0077] The term "plants" is understood herein to mean all plants and plant populations, such as desirable and undesirable wild plants or crop plants (including naturally occurring crop plants). Crop plants are plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or by a combination of these methods, including transgenic plants, and including plant cultivars that can and cannot be protected by plant breeder's rights.

[0078] For purposes of this disclosure, the term "plant" includes the types of organisms exemplified by trees, shrubs, herbs, grasses, ferns, and mosses, which typically grow locally, absorb water and necessary substances through their roots, and synthesize nutrients in their leaves by photosynthesis.

[0079] Examples of "plants" for the purposes of the present invention include, but are not limited to, crop plants such as wheat, rye, barley, lima beans, oats or rice; beets, e.g., sugar beet or fodder beet; pome fruits, drupes or soft fruits, e.g., apple, pear, plum, peach, almond, cherry, strawberry, raspberry, blackberry or gooseberry; legumes, e.g., lentil, pea, alfalfa or soybean; oilseed rape, mustard, olive, sunflower, coconut, cocoa bean, castor oil plant, oil palm, ground nuts or soybeans; cucurbits, e.g., pumpkin, cucumber, melon; fiber plants, e.g., cotton, flax, hemp, jute; citrus fruits, e.g., orange, lemon, grapefruit, mandarin orange, citrus fruits. Preferred include plants such as: horticultural plants such as spinach, lettuce, asparagus, cabbage, carrot, onion, tomato, potato, cucurbits, peppers, laurel trees such as avocado, cinnamon, camphor, cucurbits, oregano, energy and feedstock plants such as cereals, maize, soybean, other legumes, rapeseed, sugarcane, oil palm, tobacco, nuts, coffee, tea, cocoa, banana, chilli peppers, grapes (table grapes and grape juice grapes), hops, grass, sweet leaf (also called stevia), natural rubber plants or flowers, ornamental and forestry plants such as shrubs, broadleaf or evergreen trees, e.g. conifers, and plant propagation material such as seeds and crop material of these plants.

[0080] Preferably, plants for the purposes of the present invention include, but are not limited to, cereals, corn, rice, soybeans and other legumes, fruit and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbits, olive plants, tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton, potato, tomato, onion, pepper and vegetables, ornamentals, any flowering plants and other plants for human and animal use.

[0081] The term "plant parts" is understood to mean all parts and organs of a plant, above and below ground. For the purposes of this disclosure, the term "plant parts" includes, but is not limited to, cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots including the taproot, lateral roots, root hairs, root tips, root caps, rhizomes, slips, shoots, fruits, fruiting bodies, bark, stems, buds, accessory buds, meristems, nodes and internodes.

[0082] The term "locus" includes the soil, the surroundings of the plant or plant parts, and any equipment or tools used before, during or after sowing / planting the plant or plant parts.

[0083] Application of the compounds of the present disclosure, or application of the compounds of the present disclosure, optionally in compositions with other compatible compounds, to plants or plant materials or their locus includes application by techniques known to those skilled in the art, including, but not limited to, spraying, coating, dipping, fumigating, impregnating, injecting and dusting.

[0084] The term "applied" means physically or chemically attached to the plant or plant part and includes impregnation.

[0085] Thus, the present invention provides N-substituted bicyclic heteroaromatic compounds of formula (I). [ka] Formula (I) Where: R is hydrogen, cyano, NO2, C1-C 10 -Alkyl, C1-C 10 -Cyanoalkyl, C2-C 10 -Alkenyl, C2-C 10 -Alkynyl, C1-C 10 -Haloalkyl, C2-C 10 -Haloalkenyl, C2-C 10 -haloalkynyl, -OR 5 , -C2~C 10 -Alkyl-OR 5 , -C(=O)-R'', -C1~C 10-Alkyl-C(=O)-R'', -C1~C6-Alkyl-NR'R'', -C(=O)-NR'R'', -C1~C 10 -Alkyl-C(=O)-NR'R'', -C2~C6-Alkenyl-C(=O)-N(R'R'', -C1~C 10 -Alkyl-S(O) n R 6 , -S(O) n R 6 , -S(O)2-phenyl, -S(O)2-C3~C 10 -Heterocyclyl, C3-C 10 -Cycloalkyl, C3-C 10 -Halocycloalkyl, C3-C 10 -Cyanocycloalkyl, (halo)C3-C 10 -Cycloalkyl-C1~C 10 -Alkyl, C3-C 10 -Cyanocycloalkyl-C1~C 10 -Alkyl, C4-C 10 -Cycloalkenyl, C4-C 10 -Cycloalkynyl, bicyclic C5-C 12 -Alkyl, bicyclic C7-C 12 -Alkenyl, C6-C 10 -Aryl, C6-C 10 -Aryl-C1-C6-alkyl, C3-C 10 -heterocyclyl and C 10 -heterocyclyl-C1-C6-alkyl, where each group is one or more R b and optionally substituted with R b is halogen, CN, C1-C6-alkyl, C1-C6-cyanoalkyl, C1-C6-haloalkyl, -OR 5 , -C(=O)-R'', -NR'R'', -S(O) n R″ and C3-C6-cycloalkyl; or R is phenyl, naphthyl and C3-C 10 -heterocyclyl, each of which is optionally selected from the group consisting of one or more R x (which may be substituted with Rx are halogens, hydrogen, cyano, NO2, C1-C 10 -Alkyl, C1-C 10 -Cyanoalkyl, C2-C 10 -Alkenyl, C2-C 10 -Alkynyl, C1-C 10 -Haloalkyl, C2-C 10 -Haloalkenyl, C2-C 10 -haloalkynyl, -OR 5 , -C1~C6-alkyl-OR 5 , -C(=O)-R'', -NR'R'', -C1~C6-alkyl-NR'R'', -NR'C(=O)-R'', -C(=O)-NR'R'', -C1~C 10 -Alkyl-C(=O)-NR'R'', -C1-C6-alkyl-S(O) n R 6 , -S(O) n R 6 , C3~C 10 -Cycloalkyl, C3-C 10 -Halocycloalkyl, C3-C 10 -Cyanocycloalkyl, -SF5, -SCN, -S(=O) 0~1 (R 8 )(=NR 7 ), -N=S(=O) 0~1 (R 9 )(R 10 ), (Halo) C3~C 10 -Cycloalkyl-C1-C6-alkyl, C3-C 10 -Cycloalkyl-C1-C6-alkenyl, C3-C 10 -Cycloalkyl-C1-C6-alkynyl, C3-C 10 -Cyanocycloalkyl-C1-C6-alkyl, C4-C 10 -Cycloalkenyl, bicyclic C5-C 12 -Alkyl, bicyclic C7-C 12 -alkenyl, phenyl, benzyl, phenylethyl, C3-C6-heterocyclyl and C3-C6-heterocyclyl-C1-C6 alkyl, wherein each group is selected from the group consisting of one or more R c (optionally substituted with R cis selected from the group consisting of halogen, CN, C1-C6-alkyl and C1-C6-alkoxy, A is CR a or N, R a is selected from the group consisting of hydrogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-cycloalkyl and -(C=O)-R'', W 1 and W 2 is independently selected from O or S; "n" is an integer ranging from 0 to 2, R 1 and R 2 is independently selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl and C1-C4-haloalkyl; Het is selected from 5- to 6-membered heterocyclyl rings, optionally with one or more R 3 may be substituted with R 3 is independently selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl and C1-C6-haloalkyl; R 4 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy; R 5 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C2-C6-haloalkynyl-C1-C4-alkyl, C3-C 10 -Cycloalkyl, C3-C 10 -Halocycloalkyl and (Halo)C 10 -cycloalkyl-C1-C6-alkyl, R 6 is hydrogen, -NR'R'', C1-C6-alkyl, C1-C6-haloalkyl, C3-C 10-Cycloalkyl, C3-C 10 -Halocycloalkyl and (Halo)C 10 -cycloalkyl-C1-C6-alkyl, R 7 is selected from the group consisting of hydrogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, (halo)C3-C6-cycloalkyl-C1-C4-alkyl, C1-C6-alkylcarbonyl and C1-C4-haloalkylcarbonyl, R 8 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, (halo)C3-C6-cycloalkyl-C1-C4-alkyl, C1-C6-haloalkyl and C3-C6-halocycloalkyl, R 9 and R 10 is independently selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, (halo)C3-C6-cycloalkyl-C1-C4-alkyl, C1-C4-haloalkyl and C3-C6-halocycloalkyl, or R 9 and R 10 can form, together with the S atom to which they are attached, a 4-6 membered heterocycle, in which the C atoms of the heterocycle may optionally be substituted with C(=O) or C(=S), and the ring may optionally be substituted with one or more R c may be substituted with R' is selected from the group consisting of hydrogen and C1-C6-alkyl, wherein said alkyl is optionally substituted with one or more halogens or C3-C6-cycloalkyl; R'' is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C 10 -cycloalkyl, -N(R')2 and -OR', each of which is optionally substituted with one or more halogens; or R″ represents phenyl, said phenyl being optionally substituted by the group selected from halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkyl, Or, R′ and R″ together with the N atom to which they are attached can form a 4-6 membered heterocycle, in which the C atoms of the heterocycle can optionally be substituted with C(═O) or C(═S), and the ring can optionally be substituted with one or more R c may be substituted with and / or a salt, stereoisomer, metal complex, polymorph, or N-oxide thereof.

[0086] In one embodiment, the compound of formula (I) is represented by a compound of formula (IA): [ka] Formula (IA) In the formula, R 1 , R 2 , R 4 , R and Het are as defined above.

[0087] In another embodiment, the compound of formula (I) is represented by a compound of formula (IB): [ka] Formula (IB) In the formula, R 1 , R 2 , R 4 , R and Het are as defined above.

[0088] In yet another embodiment, the compound of formula (I) is represented by a compound of formula (IC): [ka] Formula (IC) In the formula, R 1 , R 2 , R 4 , R and Het are as defined above.

[0089] In yet another embodiment, the compound of formula (I) is represented by a compound of formula (ID). [ka] Expression (ID) In the formula, R 1 , R 2 , R 4 , R and Het are as defined above.

[0090] The following list refers to the compounds of formula (I) of the present invention and is intended to illustrate the substituent W 1 , W 2 , R, R x , A, R a , R b , R c , n, R 1 , R 2 ,Het,R. 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R′ and R″. For any one of these substituents, any of the definitions given below may be combined with any of the definitions of any other substituents given below or anywhere else in this specification.

[0091] In one embodiment of the present invention, W 1 and W 2 is independently selected from O or S.

[0092] In another embodiment of the present invention, W 1 and W 2 is O.

[0093] In yet another embodiment of the present invention, W 1 and W 2 is S.

[0094] In yet another embodiment of the present invention, W 1 is S and W 2 is O.

[0095] In a preferred embodiment of the present invention, W 1 and W 2 is O.

[0096] R is hydrogen, cyano, NO2, C1-C 10 -Alkyl, C1-C 10 -Cyanoalkyl, C2-C 10 -Alkenyl, C2-C 10 -Alkynyl, C1-C 10 -Haloalkyl, C2-C 10 -Haloalkenyl, C2-C 10 -haloalkynyl, -OR 5 , -C2~C 10 -Alkyl-OR 5 , -C(=O)-R'', -C1~C 10 -Alkyl-C(=O)-R'', -C1~C6-Alkyl-NR'R'', -C(=O)-NR'R'', -C1~C 10 -Alkyl-C(=O)-NR'R'', -C2~C6-Alkenyl-C(=O)-N(R'R'', -C1~C 10 -Alkyl-S(O) n R 6 , -S(O) n R 6 , -S(O)2-phenyl, -S(O)2-C5~C 10 -Heterocyclyl, C3-C 10 -Cycloalkyl, C3-C 10 -Cyanocycloalkyl, (halo)C3-C 10 -Cycloalkyl-C1~C 10 -Alkyl, C3-C 10 -Cyanocycloalkyl-C1~C 10 -alkyl, phenyl-C1-C6-alkyl and C3-C 10 -heterocyclyl-C1-C6-alkyl, where each group is one or more R b may be optionally substituted with

[0097] In another embodiment of the present invention, R is hydrogen, cyano, C1-C 10 -Alkyl, C1-C 10 -Cyanoalkyl, C2-C 10 -Alkenyl, C2-C 10 -Alkynyl, C1-C 10 -Haloalkyl, -C(=O)-R'', -OR 5 , -C1~C 10 -Alkyl-C(=O)-R'', -C1~C 10 -Alkyl-OR 5 , S(O)2-phenyl, -S(O)2-C3~C 10 -Heterocyclyl, C3-C 10 -Cycloalkyl, C3-C 10 -Cyanocycloalkyl, (halo)C3-C 10 -Cycloalkyl-C1-C6-alkyl, phenyl-C1-C4-alkyl or C3-C 10 -heterocyclyl-C1-C4-alkyl, where each group is selected from one or more R b may be optionally substituted with

[0098] In a preferred embodiment of the present invention, R is hydrogen, cyano, C1-C6-alkyl, C1-C6-cyanoalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, -C(=O)-R'', -OR 5 , -C1~C6-alkyl-C(=O)-R'', -C1~C6-alkyl-OR 5 , S(O)2-phenyl, -S(O)2-C3~C 10 -heterocyclyl, C3-C6-cycloalkyl, C3-C6-cyanocycloalkyl, (halo)C3-C6-cycloalkyl-C1-C3-alkyl, phenyl-C1-C3-alkyl or C3-C6-heterocyclyl-C1-C3-alkyl, wherein each group may be optionally substituted by one or more Rb.

[0099] In one embodiment of the present invention, R b is halogen, CN, C1-C6-alkyl, C1-C6-cyanoalkyl, C1-C6-haloalkyl, -OR5 , -C(=O)-R'', -NR'R'', -S(O) n R″ or C3-C6-cycloalkyl.

[0100] In a preferred embodiment of the present invention, R b are independently selected from CN, halogen, methyl, ethyl, and cyclopropyl.

[0101] In another embodiment of the present invention, R is selected from phenyl or naphthyl, where each group is one or more R x may be optionally substituted with

[0102] In yet another embodiment of the present invention, R is C 10 heterocyclyl, wherein the C3 to C 10 -heterocyclyl group is one or more R x may be optionally substituted with

[0103] In yet another embodiment of the present invention, R is C 10 -heterocyclyl. 10 -Heterocyclyl is oxetanyl, azetidinyl, thietanyl, thietanyl 1-oxide, thietanyl 1,1-dioxide, tetrahydro-2H-pyran-4-yl, thienyl, furanyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl. and wherein the heterocyclyl ring is bonded via either a carbon or a nitrogen ring atom and the heterocyclyl ring is optionally selected from the group consisting of one or more R xmay be substituted with.

[0104] In yet another embodiment of the present invention, R is hydrogen, cyano, C1-C6-alkyl, C1-C6-cyanoalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, -C(=O)-R'', -OR 5 , -C1~C6-alkyl-C(=O)-R'', -C1~C6-alkyl-OR 5 , -S(O)2-phenyl, -S(O)2-C3~C 10 -heterocyclyl, C3-C6-cycloalkyl, C3-C6-cyanocycloalkyl, (halo)C3-C6-cycloalkyl-C1-C3-alkyl, phenyl-C1-C3-alkyl or C3-C6-heterocyclyl-C1-C3-alkyl, each group optionally being substituted by one or more Rb, or R is phenyl, naphthyl, oxetanyl, azetidinyl, thietanyl, thietanyl 1-oxide, thietanyl 1,1-dioxide, tetrahydro-2H-pyran-4-yl, thienyl, furanyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl. , 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,3,4-triazolyl, tetrazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiazolyl, benzoxazolyl, 2,2-difluorobenzo[d][1,3]dioxol-5-yl, quinolinyl, or isoquinolinyl, wherein each group is selected from one or more of R x may be optionally substituted with

[0105] In a preferred embodiment of the invention, R is selected from phenyl, naphthyl, pyridinyl, pyrazolyl, thiazolyl, pyrrolyl, imidazolyl, thiophen-3-yl, tetrahydro-2H-pyran-4-yl, or 2,2-difluorobenzo[d][1,3]dioxol-5-yl, where each group is selected from one or more R x may be optionally substituted with

[0106] In a more preferred embodiment of the invention, R is phenyl, wherein said phenyl is one or more R x may be optionally substituted with

[0107] In the most preferred embodiments of the invention, R is selected from the following: [ka]

[0108] In one embodiment of the present invention, R x are each independently halogen, hydrogen, cyano, NO2, C1-C 10 -Alkyl, C1-C 10 -Cyanoalkyl, C2-C 10 -Alkenyl, C2-C 10 -Alkynyl, C1-C 10 -Haloalkyl, C2-C 10 -Haloalkenyl, C2-C 10 -haloalkynyl, -OR 5 , -C1~C6-alkyl-OR 5 , -C(=O)-R'', -NR'R'', -S(O) n R 6 , SF5, -SCN, -S(=O) 0~1 (R 8 )(=NR 7 )-N=S(=O) 0~1 (R 9 )(R 10 ), C3~C 10 -Cycloalkyl, C3-C 10 -Halocycloalkyl, C3-C 10 -Cyanocycloalkyl, (halo)C3-C 10-Cycloalkyl-C1-C6-alkyl, C3-C 10 -cyanocycloalkyl-C1-C6-alkyl, phenyl or C3-C6-heterocyclyl, where each group is selected from one or more R c may be optionally substituted with

[0109] In another embodiment of the present invention, R x is halogen, hydrogen, cyano, NO2, C1-C6-alkyl, C1-C6-cyanoalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, -OR 5 , -C(=O)-R'', -NR'R'', -C(=O)-NR'R'', -S(=O) 0~1 (R 8 )(=NR 7 ), -N=S(=O) 0~1 (R 9 )(R 10 ) or -S(O) n R 6 wherein each group is independently selected from one or more R c (optionally substituted with).

[0110] In another embodiment of the present invention, R c is halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, -C(=O)-R'', -NR'R'', -S(O) n R″ or C3-C6-cycloalkyl.

[0111] In yet another embodiment of the present invention, R c is selected from halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy.

[0112] In a preferred embodiment of the present invention, R xis independently selected from halogen, hydrogen, cyano, methoxy, ethoxy, isopropoxy, cyclopropoxy, cyclobutoxy, allyloxy, propargyloxy, cyclopropylmethyloxy, cyclopropyl, difluoromethyl, trifluoroethyl, trifluoromethyl, methyl, ethyl, propyl, -SMe, -SCF3, -SO2Me, -NO2, dimethylamino, diethylamino, fluoromethoxy, difluoromethoxy, fluoroethoxy, trifluoromethoxy, or trifluoroethoxy, where each group is selected from one or more R c may be optionally substituted with

[0113] In one embodiment of the present invention, R 5 is selected from hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C2-C4-haloalkynyl-C1-C2-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl or (halo)C3-C6-cycloalkyl-C1-C4-alkyl.

[0114] In another embodiment of the present invention, R 5 is selected from hydrogen, C1-C3-alkyl, C1-C3-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl or C3-C6-cycloalkyl-C1-C3-alkyl.

[0115] In a preferred embodiment of the present invention, R 5 is selected from hydrogen, methyl, ethyl, propyl, butyl, allyl, propargyl, difluoromethyl, trifluoromethyl, trifluoroethylcyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl or cyclobutylethyl.

[0116] In one embodiment of the present invention, OR 5is selected from hydroxy, methoxy, ethoxy, propoxy, butyloxy, allyloxy, propargyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclopropylmethoxy, cyclopropylethoxy, cyclobutylmethoxy, fluoromethoxy, difluoromethoxy, fluoroethoxy, trifluoromethoxy or trifluoroethoxy.

[0117] In one embodiment of the invention, OR' is selected from hydroxy, methoxy, ethoxy, propoxy, butyloxy, cyclopropyloxy, cyclobutyloxy, cyclobutyloxy, cyclopentyloxy, fluoromethoxy, difluoromethoxy, fluoroethoxy, trifluoromethoxy or trifluoroethoxy.

[0118] In one embodiment of the present invention, C1-C6-alkyl-OR 5 is selected from hydroxymethyl, methoxymethyl, ethoxymethyl, propoxymethyl, hydroxyethyl, methoxyethyl, ethoxyethyl, propoxyethyl, cyclopropylmethoxymethyl, cyclobutylmethoxymethyl or cyclopentylmethoxymethyl.

[0119] In one embodiment of the present invention, R 6 is selected from hydrogen, -NR'R'', C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl or C3-C6-cycloalkyl-C1-C4-alkyl.

[0120] In another embodiment of the invention, R6 is selected from hydrogen, -NR'R'', C1-C3-alkyl, C1-C3-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl or C3-C6-cycloalkyl-C1-C6-alkyl.

[0121] In a preferred embodiment of the present invention, R 6is selected from methyl, ethyl, propyl, difluoromethyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl or cyclobutylethyl.

[0122] In one embodiment of the present invention, R 7 is selected from hydrogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, (halo)C3-C6-cycloalkyl-C1-C3-alkyl, C1-C3-alkylcarbonyl or C1-C3-haloalkylcarbonyl.

[0123] In another embodiment of the present invention, R 8 is selected from C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C3-alkyl, C1-C4-haloalkyl or C3-C6-halocycloalkyl.

[0124] In yet another embodiment of the present invention, R 9 and R 10 is independently selected from C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C3-alkyl, C1-C4-haloalkyl or C3-C6-halocycloalkyl.

[0125] In one embodiment of the invention, R' is selected from hydrogen or C1-C3-alkyl, wherein said alkyl may be optionally substituted with one or more halogens or C3-C6-cycloalkyl.

[0126] In another embodiment of the present invention, R'' is selected from hydrogen, C1-C3-alkyl, C1-C3-haloalkyl, C3-C6-cycloalkyl, -N(R')2 or -OR'.

[0127] In another embodiment of the invention, R' and R'' together with the N atom to which they are attached can form a 4-6 membered heterocyclic ring, in which the C atoms of the heterocyclic ring can be optionally substituted with C(=O) or C(=S), wherein said ring can be formed by the addition of one or more R c may be optionally substituted with

[0128] In one embodiment of the present invention, R 1 and R 2 are independently selected from hydrogen, halogen, cyano, C1-C4-alkyl, or C1-C4 haloalkyl.

[0129] In another embodiment of the present invention, R 1 and R 2 is independently selected from hydrogen or halogen.

[0130] In a preferred embodiment of the present invention, R 1 and R 2 is hydrogen.

[0131] In one embodiment of the present invention, R 3 are independently selected from hydrogen, halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl.

[0132] In another embodiment of the present invention, R 3 is independently selected from halogen or C1-C4-haloalkyl.

[0133] In yet another embodiment of the present invention, R 3 is independently selected from: [ka] where TIFF2024546050000010.tif118 is a combination.

[0134] In a preferred embodiment of the present invention, R 3 is independently selected from halogen, CN, difluoromethyl or trifluoromethyl.

[0135] In a more preferred embodiment of the present invention, R 3 is chloro.

[0136] In one embodiment of the present invention, R 4 is selected from hydrogen, halogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy.

[0137] In another embodiment of the present invention, R 4 is selected from hydrogen, halogen, methoxy or cyano.

[0138] In a preferred embodiment of the present invention, R 4 is hydrogen.

[0139] In one embodiment of the invention, A is CR a or N, where R a is selected from the group consisting of hydrogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-cycloalkyl and -(C=O)-R''.

[0140] In a preferred embodiment of the invention, A is nitrogen (N).

[0141] In one embodiment of the invention, Het is selected from 5-6 membered heterocyclyl rings, which are optionally R 3 may be substituted with.

[0142] In another embodiment of the invention, Het is selected from one of Het-1 to Het-6. [ka] where # indicates the point of attachment to the remainder of the molecule. m is 0, 1 or 2. R3 is the same as described above in this specification.

[0143] In yet another embodiment of the invention, Het is selected from one of Het-1-a to Het-6-b. [ka] where # indicates the point of attachment to the remainder of the molecule. m is 0, 1 or 2. R 3 is the same as described above in this specification.

[0144] In a preferred embodiment of the invention, Het is selected from one of the following: [ka] where # indicates the point of attachment to the remainder of the molecule. m is 0, 1 or 2. R 3 is the same as defined herein above.

[0145] In a more preferred embodiment of the invention, Het is selected from one of the following: [ka] where # indicates the point of attachment to the remainder of the molecule. R 3 is independently selected from halogen or C1-C4-haloalkyl, preferably halogen, difluoromethyl or trifluoromethyl, more preferably halogen is chloro.

[0146] In another preferred embodiment, the present invention provides compounds of formula (I): [ka] Formula (I) Where: R is phenyl, naphthyl and C3-C10 -heterocyclyl, each of which is optionally selected from one or more of R x may be substituted with R x are halogens, hydrogen, cyano, NO2, C1-C 10 -Alkyl, C1-C 10 -Cyanoalkyl, C2-C 10 -Alkenyl, C2-C 10 -Alkynyl, C1-C 10 -Haloalkyl, C2-C 10 -Haloalkenyl, C2-C 10 -haloalkynyl, -OR 5 , -C1~C6-alkyl-OR 5 , -C(=O)-R'', -NR'R'', -C1~C6-alkyl-NR'R'', -NR'C(=O)-R'', -C(=O)-NR'R'', -C1~C 10 -Alkyl-C(=O)-NR'R'', -C1~C6-Alkyl-S(O)nR 6 , -S(O) n R 6 , C3~C 10 -Cycloalkyl, C3-C 10 -Halocycloalkyl, C3-C 10 -Cyanocycloalkyl, -SF5, -SCN, -S(=O) 0~1 (R 8 )(=NR 7 ), -N=S(=O) 0~1 (R 9 )(R 10 ), (Halo) C3~C 10 -Cycloalkyl-C1-C6-alkyl, C3-C 10 -Cycloalkyl-C1-C6-alkenyl, C3-C 10 -Cycloalkyl-C1-C6-alkynyl, C3-C 10 -Cyanocycloalkyl-C1-C6-alkyl, C4-C 10 -Cycloalkenyl, bicyclic C5-C 12 -Alkyl, bicyclic C7-C 12-alkenyl, phenyl, benzyl, phenylethyl, C-C-heterocyclyl and C-C-heterocyclyl-C-C-alkyl, where each group is one or more of R c and optionally substituted with R c is selected from the group consisting of halogen, CN, C1-C6-alkyl and C1-C6-alkoxy, A is CR a or N, R a is selected from the group consisting of hydrogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-cycloalkyl and -(C=O)-R'', W 1 and W 2 is independently selected from O or S; "n" is an integer ranging from 0 to 2, R 1 and R 2 is independently selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl and C1-C4-haloalkyl; Het is selected from 5- to 6-membered heterocyclyl rings, optionally with one or more R 3 may be substituted with R 3 is independently selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl and C1-C4-haloalkyl; R 4 is selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, R 5is selected from the group consisting of hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C2-C4-haloalkynyl-C1-C2-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl and (halo)C3-C6-cycloalkyl-C1-C4-alkyl, R 6 is hydrogen, -NR'R'', C1-C4-alkyl, C1-C4-haloalkyl, C3-C 10 -Cycloalkyl, C3-C 10 -Halocycloalkyl, and (halo)C 10 -cycloalkyl-C1-C6-alkyl, R 7 is selected from the group consisting of hydrogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, (halo)C3-C6-cycloalkyl-C1-C3-alkyl, C1-C3-alkylcarbonyl and C1-C3-haloalkylcarbonyl, R 8 is independently selected from the group consisting of C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, (halo)C3-C6-cycloalkyl-C1-C3-alkyl, C1-C4-haloalkyl and C3-C6-halocycloalkyl; R 9 and R 10 are independently selected from the group consisting of C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, (halo)C3-C6-cycloalkyl-C1-C3-alkyl, C1-C4-haloalkyl and C3-C6 halocycloalkyl, or R 9 and R 10 can form, together with the S atom to which they are attached, a 4-6 membered heterocycle, in which the C atoms of the heterocycle may optionally be substituted with C(=O) or C(=S), and the ring may optionally be substituted with one or more Rc may be substituted with R' is selected from the group consisting of hydrogen and C1-C6-alkyl, wherein said alkyl is optionally substituted with one or more halogens or C3-C6 cycloalkyl; R'' is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C 10 -cycloalkyl, -N(R')2 and -OR', each of which is optionally substituted with one or more halogens; or R" represents phenyl, said phenyl optionally substituted with a group selected from halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkyl, said alkyl optionally substituted with one or more halogens, or R' and R'' may together with the N atom to which they are attached form a 4-6 membered heterocycle, the C atoms of which may be optionally substituted by C(=O) or C(=S), and the ring may be formed by one or more R c and optionally substituted with and / or a salt, stereoisomer, metal complex, polymorph, or N-oxide thereof.

[0147] In yet another preferred embodiment, the present invention provides compounds of formula (I): [ka] Formula (I) In the formula, R is phenyl and C3-C 10 -heterocyclyl, wherein phenyl and C3-C 10 Heterocyclyl is a heterocyclic group consisting of one or more R x may be optionally substituted with R x is halogen, hydrogen, cyano, NO2, C1-C6-alkyl, C1-C6-cyanoalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, -OR5 , -C1~C6-alkyl-OR 5 , -C(=O)-R'', -NR'R'', -C1~C6-alkyl-NR'R'', -NR'C(=O)-R'', -C(=O)-NR'R'', -C1~C6-alkyl, -C(=O)-NR'R'', -C1~C6-alkyl-S(O) n R 6 , -S(O) n R 6 , -S(=O) 0~1 (R 8 )(=NR 7 ) and -N=S(=O) 0~1 (R 9 )(R 10 ), wherein each group optionally has one or more R c may be substituted with R c is selected from the group consisting of halogen, CN, C1-C4-alkyl and C1-C4-alkoxy, A represents nitrogen (N); W 1 and W 2 is O, "n" is an integer ranging from 0 to 2, R 1 and R 2 is hydrogen, Het is selected from either Het-1-a, Het-3-a or Het-5-a. [ka] "m" is an integer ranging from 0 to 2, R 3 is selected from halogen or C1-C4-haloalkyl; R 4 is selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl and C1-C4-haloalkyl, R 5 is selected from the group consisting of hydrogen, C1-C3-alkyl, C1-C3-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and C3-C6-cycloalkyl-C1-C3-alkyl, R 6is selected from the group consisting of hydrogen, -NR'R'', C1-C3-alkyl, C1-C3-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and C3-C6-cycloalkyl-C1-C6-alkyl, R 7 is selected from the group consisting of hydrogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, (halo)C3-C6-cycloalkyl-C1-C3-alkyl, C1-C3-alkylcarbonyl and C1-C3-haloalkylcarbonyl, R 8 is independently selected from the group consisting of C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C3-alkyl, C1-C4-haloalkyl and C3-C6-halocycloalkyl, R 9 and R 10 are independently selected from the group consisting of C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C3-alkyl, C1-C4-haloalkyl or C3-C6-halocycloalkyl, or R 9 and R 10 can form, together with the S atom to which they are attached, a 4-6 membered heterocycle, the C atoms of which may optionally be substituted with C(=O) or C(=S), and the ring may optionally be substituted with one or more R c may be substituted with R' is selected from the group consisting of hydrogen and C1-C3-alkyl, said alkyl optionally being substituted with one or more halogens or C3-C6-cycloalkyl; R″ is selected from the group consisting of hydrogen, C1-C3-alkyl, C1-C3-haloalkyl, C3-C6-cycloalkyl, —N(R′)2 and —OR′, each of which may be optionally substituted with one or more halogens, or R" represents phenyl, said phenyl being optionally substituted by the group selected from halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkyl, or R′ and R″ together with the N atom to which they are attached may form a 4-6 membered heterocycle, the C atoms of which may optionally be substituted by C(═O) or C(═S), and the ring may optionally be substituted by one or more R c may be substituted with and / or a salt, stereoisomer, metal complex, polymorph or N-oxide thereof.

[0148] In a more preferred embodiment, the compound of formula (I) is 3-allyl-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-ethylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-methylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(cyclopropylmethyl)pyrido[ 2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(2-methylallyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-((2-chlorothiazol-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3,8-bis((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 2-(8-((6-chloropyridin- 3-(3-chloropropyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dioneacetic acid, 8-((6-chloropyridin-3-yl)methyl)-3-(3-fluoropropyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione 4-(8-((6-chloropyridin-3-yl)methyl)-2,4-dioxo-4,8-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)butanenitrile, 3-butyl-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-propylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(prop-2-yn-1-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-isopropylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 2-(8-((6-chloropyridin-3-yl)methyl)-2,4-dioxo-4,8-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)acetonitrile, 8-((6-chloropyridin-3-yl)methyl)-3-(pent-4-en-1-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6 -chloropyridin-3-yl)methyl)-3-(cyclobutylmethyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(but-3-en-1-yl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(4-methylpent-3-en-1-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(4,4,4 trifluorobutyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(2-fluoroethyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(5,6,6 trifluorohex-5-en-1-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(2-ethoxyethyl)pyrido[2,3-d]pyrimidine 8-((6-chloropyridin-3-yl)methyl)-3-((2,2-difluorocyclopropyl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(4,4-difluorobut-3-en-1-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(2,2,2 trifluoroethyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(2,2-difluoroethyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-2,4-dioxo-4,8-dihydropyrido[2,3-d]pyrimidine-3(2H)-carbonitrile, 8-((6-chloropyridin-3-yl)methyl)-3-(2,2,3,3-pentafluoropropyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin- 3-(methoxymethyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-ethylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-methylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 2-(8-((2-chlorothiazol-5-yl)methyl)-3-methylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione 8-((2-chlorothiazol-5-yl)methyl)-2,4-dioxo-4,8-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)acetonitrile, 8-((2-chlorothiazol-5-yl)methyl)-3-isopropylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-2,4-dioxo-4,8-dihydropyrido[2,3-d]pyrimidine-3(2H)-carbonitrile, 8-((2-chlorothiazol-5-yl)methyl)-3-(2-fluoroethyl)pyrido[2 ,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(2,2,2-trifluoroethyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(2,2-difluoroethyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(2,2,3,3-pentafluoropropyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-allyl-8-((2-chlorothiazol-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(prop-2-yn-1-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-acetyl-8-((2-chlorothiazol-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(4,4,4 trifluoro butyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(cyclopropylmethyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(cyclopropanecarbonyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-acetyl-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2 -chlorothiazol-5-yl)methyl)-3-(4,4-difluorobut-3-en-1-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(cyclopropanecarbonyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-chloropropyl)-8-((2-chlorothiazol-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-fu phenylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(3-cyclopropylprop-2-yn-1-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(4-methoxypyridin-2-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(3-methoxyphenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(2-methoxyphenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(4-methoxyphenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(tert-butyl)-8-((6-chloropyridin-3-yl)methyl)-3-(4-methoxyphenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione 8-((6-chloropyridin-3-yl)methyl)-3-(3-methylbutan-2-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-phenylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(sec-butyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(3-methylbutan-2-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, chloropyridin-3-yl)methyl)-3-cyclopropylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(3-methylbutan-2-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(sec-butyl)-8-((2-chlorothiazol-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-cyclopropylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione 1-(8-((6-chloropyridin-3-yl)methyl)-2,4-dioxo-4,8-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)cyclopropane-1-carbonitrile, 1-(8-((2-chloropyrimidin-5-yl)methyl)-2,4-dioxo-4,8-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)cyclopropane-1-carbonitrile, 1-(8-((2-chlorothiazol-5-yl)methyl)-2,4-dioxo-4,8-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)cyclopropane-1-carbonitrile, 8-((2-chlorothiazol-5-yl)methyl)-3-(4-methoxyphenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(3-methoxyphenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(2-methoxyphenyl)pyrido[2,3-d]pyrimidine-2,4(3H, ,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(4-methylpentan-2-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(pentan-2-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(1-methoxypropan-2-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(1-methoxypropan-2-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl )-3-(1-methoxybutan-2-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(4-methylpentan-2-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(4-chlorophenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(4-chlorophenyl)-8-((2-chlorothiazol-5-yl)methyl)pyrido[2,3-d]pyrimidine -2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(1-methyl-1H-pyrazol-4-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(4-chlorophenyl)-8-((2-chloropyrimidin-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-ethylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-ethylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(tert-pentyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(pentan-2-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(3-(trifluoromethyl)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(3-(trifluoromethyl)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(1-methyl-1H-pyrazol-4-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(1-methoxypropan-2-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(1-methoxypropan-2-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, thiazol-5-yl)methyl)-3-(1-methoxybutan-2-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(1-methylcyclopropyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(2-methoxyethyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-chlorophenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3- d]pyrimidine-2,4(3H,8H)-dione, 3-(8-((6-chloropyridin-3-yl)methyl)-2,4-dioxo-4,8-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)benzonitrile, 3-(3-chlorophenyl)-8-((2-chloropyrimidin-5-yl)methyl)pyrido[2,3-d]pyrimidin-2,4(3H,8H)-dione, 3-(8-((2-chloropyrimidin-5-yl)methyl)-2,4-dioxo-4,8-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)benzonitrile, 8 -((6-chloropyridin-3-yl)methyl)-3-(1,1,1-trifluoropropane-di-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(1-methylcyclopropyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(2-methoxyethyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(3,5-dichlorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(4-(trifluoromethyl)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 4-(8-((6-chloropyridin-3-yl)methyl)-2,4-dioxo-4,8-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)benzonitrile, 8-((6-chloropyridin-3-yl)methyl)-3-(3,4-dichlorophenyl)pyrido[2,3-d]pyrimidine 3-(4-bromophenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(4-bromophenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3,5-bis(trifluoromethyl)phenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-bromo-5-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione phenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-chloro-5-(trifluoromethyl)phenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(1-ethyl-1H-pyrazol-4-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(3 -ethoxyphenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(1-methyl-1H-pyrazol-5-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(2-fluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(3-fluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(3,4-difluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(3,5-difluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(4-fluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3- (3-fluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(2,4-dichlorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(3,4-difluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(m-tolyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione , 8-((6-chloropyridin-3-yl)methyl)-3-(4-(methylthio)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(3-(trifluoromethoxy)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(3-(difluoromethoxy)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(3-(difluoromethoxy)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)- 3-(p-tolyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(4-(trifluoromethoxy)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(4-(difluoromethoxy)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(m-tolyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(4-(methylthio)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(3-(trifluoromethoxy)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(3-(difluoromethoxy)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyrimidinyl)methyl)-3-(4-(methylthio)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione 2-chloro-5-(8-((6-chloropyridin-3-yl)methyl)-2,4-dioxo-4,8-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)benzonitrile; 3-(4-chloro-2-fluorophenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido [2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-cyclopentylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(4-methylcyclohexyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(4-chloro-3-fluorophenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-cyclopentylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, Lysin-3-yl)methyl)-3-(2,4-difluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(3,5-difluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(3,5-difluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(p-tolyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(3-fluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(p-tolyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(4-chlorophenyl)-8-((6-(trifluoromethyl)pyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 2-chloro-5-(8-((2-chloropyrimidin-5-yl)methyl)-2,4-dioxo-4,8-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)benzonitrile, 3-(4-chloro-2-fluorophenyl)-8-((2-chloropyrimidin-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-(( 2-chloropyrimidin-5-yl)methyl)-3-cyclohexylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(4-(methylthio)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(3-(trifluoromethoxy)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(3-( difluoromethoxy)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(4-(methylsulfonyl)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(4-fluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-chloro-4-fluorophenyl)-8-((2-chloropyrimidin-5-yl)methyl)pyrido[2,3 -d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(4-(dimethylamino)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(4-fluorophenyl)-8-((6-(trifluoromethyl)pyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-chlorophenyl)-8-((6-(trifluoromethyl)pyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(3,4-dichlorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(4-bromophenyl)-8-((2-chloropyrimidin-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(4-(difluoromethoxy)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl) ethyl)-3-(tetrahydro-2H-pyran-4-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(2-fluorophenyl)-8-((6-(trifluoromethyl)pyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(tetrahydro-2H-pyran-4-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-chloro-4-fluorophenyl)-8-((6-chloropyridine- 3-(3-chloro-4-fluorophenyl)-8-((2-chlorothiazol-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 2-chloro-5-(8-((2-chlorothiazol-5-yl)methyl)-2,4-dioxo-4,8-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)benzonitrile, 3-(4-chloro-3-methoxyphenyl)-8-((2-chlorothiazol-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(2-chloro-4-fluorophenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-chloro-2-fluorophenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(4-chloro-3-methoxyphenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(4-chloro-3-methoxyphenyl)-8-((2-chloropyrimidin-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-(trifluoromethyl)phenyl)-8-((6-(trifluoromethyl)pyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(2,3-difluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(2,3-difluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-benzyl-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-cyclopentylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-cyclopentylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-cyclopentylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(thiophen-3-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(thiophen-3-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(thiophen-3-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-ethyl-8-((6-(trifluoromethyl)pyridin-3-yl )methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(3,4-dichlorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(4-(difluoromethoxy)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(4-methylcyclohexyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(4-methylcyclohexyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(3-(difluoromethyl)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(3-(difluoromethyl)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(4-chlorophenyl)-8 -((6-chloropyridin-3-yl)methyl)-2-thioxo-2,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one, 8-((6-chloropyridin-3-yl)methyl)-3-(4-fluorophenyl)-2-thioxo-2,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one, 8-((6-chloropyridin-3-yl)methyl)-2-thioxo-3-(3-(trifluoromethyl)phenyl)-2,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one, 3-(4-bromophenyl)-8-((6 -chloropyridin-3-yl)methyl)-2-thioxo-2,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one, 3-(4-chlorophenyl)-8-((tetrahydrofuran-3-yl)methyl)pyrido[2,3-d]pyrimidin-2,4(3H,8H)-dione, 3-(4-chloro-2-fluorophenyl)-8-((2-chlorothiazol-5-yl)methyl)pyrido[2,3-d]pyrimidin-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(4-methoxy-3-(trifluoromethyl)pyrido[2,3-d]pyrimidin-4(3H)-one, 3-(3-chloro-4-(trifluoromethoxy)phenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(o-tolyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(2-chlorophenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(2-fluorophenyl)pyrido[2,3-d]pyrimidine-2,4 (3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(3,5-dichlorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-bromophenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(3-(difluoromethyl)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)- 8-((2-chloropyrimidin-5-yl)methyl)-3-(2,3-difluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(2,6-difluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(2,4-difluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(2,4-difluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione 3-(4-chloro-3-fluorophenyl)-8-((2-chloropyrimidin-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-2-thioxo-3-(4-(trifluoromethoxy)phenyl)-2,8-dihydropyrido[2,3-d]pyrimidine-4(3H)-one, 3-(4-chlorophenyl)-8-((2-chloropyrimidin-5-yl)methyl)-2-thioxo-2,8-Dihydropyrido[2,3-d]pyrimidin-4(3H)-one, 8-((6-chloropyridin-3-yl)methyl)-3-(3-(2,2,2 trifluoroethoxy)phenyl)pyrido[2,3-d]pyrimidin-2,4(3H,8H)-dione, 3-(3-chloro-4-(trifluoromethoxy)phenyl)-8-((2-chlorothiazol-5-yl)methyl)pyrido[2,3-d]pyrimidin-2,4(3H,8H)-di, , 8-((2-chloropyrimidin-5-yl)methyl)-3-(4-fluoro-3-(trifluoromethyl)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(2,3-difluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(2,6-difluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(2,6-difluorophenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-chloro-2-fluorophenyl)-8-((2-chlorothiazol-5-yl)methyl)-pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-chloro-4-fluorophenyl)-8-((6-chloropyridin-3-yl)methyl)-2-thioxo-2,8-dihydropyrido[2,3-d]pyrimidine-4(3H)-one, 3-(4 -Chloro-3-(trifluoromethyl)phenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(4-chloro-3-methoxyphenyl)-8-((6-chloropyridin-3-yl)methyl)-2-thioxo-2,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one, 8-((6-chloropyridin-3-yl)methyl)-3-(thiophen-3-yl)-2-thioxo-2,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one , 8-((6-chloropyridin-3-yl)methyl)-3-(4-fluoro-3-(trifluoromethyl)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(4-(2,2,2 trifluoroethoxy)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(4-chloro-3-(trifluoromethyl)phenyl)-8-((2-chloropyrimidin-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(2-chloro-4-fluorophenyl)-8-((2-chloropyrimidin-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-chloro-2-fluorophenyl)-8-((2-chloropyrimidin-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-chloro-4-(trifluoromethoxy)phenyl)-8-((2-chloropyrimidin-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6- chloropyridin-3-yl)methyl)-3-(2,4-difluorophenyl)-2-thioxo-2,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one, 8-((6-chloropyridin-3-yl)methyl)-3-(3-fluoro-4-methoxyphenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-bromo-4-methoxyphenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-bromophenyl)-8-((2-chloro pyrimidin-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-bromo-4-fluorophenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(4-bromo-3-fluorophenyl)-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(3-bromo-4-fluorophenyl)-8-((2-chloropyrimidin-5-yl)methyl)pyrido[2,3-d ]pyrimidine-2,4(3H,8H)-dione, 3-(4-bromo-3-fluorophenyl)-8-((2-chloropyrimidin-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(2-chloro-4-fluorophenyl)-8-((6-chloropyridin-3-yl)methyl)-2-thioxo-2,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one, 3-(2-chloro-4-fluorophenyl)-8-((2-chlorothiazol-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(1-methyl-1H-pyrazol-3-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(1-phenylethyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(3,4-dichlorophenyl)-2-thioxo-2,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one, 8-((6- chloropyridin-3-yl)methyl)-3-(1-phenylethyl)-2-thioxo-2,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one, 8-((2-chlorothiazol-5-yl)methyl)-3-(4-fluoro-3-(trifluoromethyl)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chlorothiazol-5-yl)methyl)-3-(4-(2,2,2 trifluoroethoxy)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-( (2-chloropyrimidin-5-yl)methyl)-3-(3-fluoro-5-(trifluoromethyl)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(4-cyclopropylphenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((6-chloropyridin-3-yl)methyl)-3-(3-((trifluoromethyl)thio)phenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 8-((2-chloropyrimidin-5-yl)methyl)-3-(4-cyclopropylphenyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(4-bromo-3-fluorophenyl)-8-((2-chlorothiazol-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, 3-(4-bromo-3-fluorophenyl)-8-((2-chlorothiazol-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione, and 3-(3-bromophenyl)-8-((2-chlorothiazol-5-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione.

[0149] The compounds of the present invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. Those skilled in the art will understand that one stereoisomer may be more active and / or exhibit beneficial effects when enriched with respect to or separated from other stereoisomers. Furthermore, those skilled in the art will know how to separate, enrich and / or selectively prepare said stereoisomers. The compounds of the present invention may exist as a mixture of stereoisomers, individual stereoisomers, or optically active forms.

[0150] When the compound of formula (I) is cationic or can form a cation, the anion portion of the salt can be inorganic or organic. Alternatively, when the compound of formula (I) is anionic or can form an anion, the cationic portion of the salt can be inorganic or organic. Examples of inorganic anion portions of the salt include, but are not limited to, chloride, bromide, iodide, fluoride, sulfate, phosphate, nitrate, nitrite, bicarbonate and hydrogen sulfate. Examples of organic anion portions of the salt include, but are not limited to, formate, alkanoate, carbonate, acetate, trifluoroacetate, trichloroacetate, propionate, glycolate, thiocyanate, lactate, succinate, malate, citrate, benzoate, cinnamate, oxalate, alkyl sulfate, alkyl sulfonate, aryl sulfonate, aryl disulfonate, alkyl phosphonate, aryl phosphonate, aryl diphosphonate, p-toluene sulfonate and salicylate. The inorganic cation portion of the salt includes, but is not limited to, alkali metals, alkaline earth metals, and the organic cation portion of the salt includes, but is not limited to, pyridine, methylamine, imidazole, benzimidazole, hydidine, phosphazene, tetramethylammonium, tetrabutylammonium, choline, and trimethylamine.

[0151] The metal ions in the metal complexes of the compounds of formula (I) are in particular elements of the second main group, such as calcium, magnesium, elements of the third and fourth main groups, such as aluminum, tin, lead, elements of the first to eighth transition groups, such as chromium, manganese, iron, cobalt, nickel, copper, zinc, etc. Metal ions of elements of the fourth period and the first to eighth transition groups are particularly preferred. Here, the metals can be present in the various valencies that they can assume.

[0152] In one embodiment, the present invention provides a compound of formula (I) in the form of a salt, metal complex, stereoisomer, polymorph or N-oxide thereof, and a composition thereof comprising an excipient, an inert carrier or any other necessary ingredient, such as a surfactant, an additive, a solid diluent and a liquid diluent. The salt of the compound of formula (I) is preferably a veterinarily and / or agriculturally acceptable salt, preferably an agriculturally acceptable salt. They can be formed in the usual manner, for example, when the compound of formula (I) has a basic functional group, by reacting the compound with an acid of the anion.

[0153] The term "N-oxide" includes any compound of Formula (I) having at least one tertiary nitrogen atom oxidized to an N-oxide moiety.

[0154] Compounds of formula (I) (including all stereoisomers, N-oxides and salts thereof) typically exist in more than one form, and thus formula (I) includes all crystalline and non-crystalline forms of the compounds represented by formula (I). Non-crystalline forms include embodiments that are solids, such as waxes and gums, and liquids, such as solutions and melts. Crystalline forms include embodiments that represent essentially a single crystal type and embodiments that represent a mixture of polymorphs (i.e., different crystal types). The term "polymorph" refers to a particular crystalline form of a compound that can crystallize in different crystalline forms, these forms having different arrangements and / or conformations of the molecules in the crystal lattice. Polymorphs can have the same chemical composition, but can also differ in composition due to the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in chemical, physical and biological properties, such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspendability, dissolution rate and bioavailability. One of ordinary skill in the art will appreciate that a polymorph of a compound of formula (I) may exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) over another polymorph or mixture of polymorphs of the same compound of formula (I). Preparation and isolation of a particular polymorph of a compound of formula (I) can be accomplished by methods known to those of ordinary skill in the art, including, for example, crystallization using a selected solvent and temperature.

[0155] In one embodiment, the present invention provides a process for the preparation of a compound of formula (I) or a salt thereof, wherein A is N. [ka] Formula (I)

[0156] The compounds of the invention as defined in formula (I) and / or table (I) can be prepared by known methods and in a variety of ways as depicted in the following schemes: The compounds of the invention can be prepared as shown in the following schemes, in which, unless otherwise indicated, the definitions of each variable are as defined above for compounds of formula (I).

[0157] <General synthesis scheme> [Reaction Scheme 1] [ka] In the formula, R, R 1 , R 2 , R 4 , LG and Het have the above mentioned meanings.

[0158] Compounds of formula (I) can be prepared from compounds of formula (2A) via N-alkylation by reacting with compounds of formula (4C). LG is preferably a halogen (preferably iodide or bromide) or tosylate or nosylate or mesylate, and the reaction is carried out in the presence of a suitable base such as sodium or potassium or cesium carbonate or sodium hydride, optionally in the presence of a suitable catalyst such as sodium iodide or tert-butylammonium iodide or tert-butylammonium bromide, and in a suitable solvent such as N,N,-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, tetrahydrofuran or acetonitrile, at a temperature between 0°C and 150°C, following the same procedure as disclosed in Journal of Medicinal Chemistry, 2002, 45(1), 219-232.

[0159] Alternatively, the compound of formula (I) can be prepared by metal catalysis. Examples of metal catalysts used in such reactions include copper catalysts such as copper(I) iodide, copper(I) bromide, copper(I) chloride, copper(I) oxide, trifluoromethanesulfonic acid copper(I) salt benzene complex, 2-thiophene carboxylic acid copper(I) salt, and nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel chloride, and palladium catalysts and ligands such as palladium acetate, for example, 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)ethane, 1,4-bis(diphenylphosphino)ethane, 1,5-bis(diphenylphosphino)ethane, 1,6-bis(diphenylphosphino)ethane, 1,7-bis(diphenylphosphino)ethane, 1,8-bis(diphenylphosphino)ethane, 1,9-bis(diphenylphosphino)ethane, 1,10-bis(diphenylphosphino)ethane, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)ethane, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)ethane, 1,4-bis(diphenylphosphino)ethane, 1,5-bis(diphenylphosphino)ethane, 1,6-bis(diphenylphosphino)ethane, 1,7-bis(diphenylphosphino)ethane, 1,8-bis(diphenylphosphino)ethane, 1,9-bis (5-di-phenylphosphino)propane, XantPhos ((5-di-phenylphosphanyl-9,9-dimethyl-xanthen-4-yl)diphenylphosphane), XPhos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl), RuPhos (2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl), BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthalene), and 1,1'-bis(diphenylphosphino)ferrocene. Examples of suitable bases include, but are not limited to, alkali metal carbonates, sodium or potassium tert-butoxide, or diisopropylethylamine, or pyridine, or 1,8-diazabicyclo[5.4.0]undec-7-ene, or 4-(dimethylamino)pyridine, in a suitable solvent such as acetonitrile or dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, at a temperature ranging from about 25° C. to about 120° C., following similar procedures as disclosed in Chem Rev, 2004, 248, 2337-2364.

[0160] [Reaction Scheme 2] [ka] In the formula, R, R 1, R 2 , R 4 and Het have the above mentioned meanings.

[0161] In another method, compounds of formula (I), where R is aryl or heteroaryl, can be prepared from compounds of formula (4B) under Chan-Lam coupling conditions. The reaction conditions include, but are not limited to, carrying out the reaction in the presence of a copper source, such as copper(I) iodide or copper(II) acetate, optionally in the presence of a suitable base, such as pyridine or potassium phosphate, in an inert solvent, such as dichloromethane, dioxane or dimethylsulfoxide, at a temperature ranging from about 25° C. to about 150° C., optionally under microwave conditions, preferably under an oxygen atmosphere, following a similar procedure as disclosed in Tetrahedron Letters, 2015, 56(33), 4843-4847.

[0162] [Reaction Scheme 3] [ka] In the formula, X is a halogen and R 1 , R 2、 R 4 and Het, has the above meaning.

[0163] Compounds of formula (3) can be converted to compounds of formula (5A) by reaction with compounds of formula (4A) in the presence of an inert solvent such as ethanol, n-butanol, tetrahydrofuran, dimethylsulfoxide or mixtures thereof, and a suitable base such as triethylamine, diisopropylamine 1,8-diazabicyclo[5.4.0]undec-7-ene, N-methylpyrrolidine or pyridine. The reaction can be carried out at a temperature ranging from about 50° C. to about 180° C., optionally under microwave conditions, following similar procedures as disclosed in the prior art, for example WO2006 / 020070, WO2007 / 021450.

[0164] Compounds of formula (5A) can undergo a cyclocondensation reaction when treated with 1,3-diketone compounds of formula (6A), optionally in the presence of a suitable base, to give bicyclic compounds of formula (2A). Examples of suitable bases include, but are not limited to, piperidine, morpholine, N-methylpiperazine, diethylamine, triethylamine, and the like. Examples of suitable solvents include, but are not limited to, methanol, ethanol, isopropanol, ethylene glycol, and the like. The reaction can be carried out at a temperature ranging from 50°C to 150°C. When one of the electrophilic centers of compounds of formula (6A) is protected (e.g., an aldehyde masked as a ketal), the condensation can be carried out in the presence of a suitable solvent and in the presence of a suitable acid, such as acetic acid, sulfonic acid, sulfuric acid, hydrochloric acid, and the like. Examples of suitable solvents include, but are not limited to, methanol, ethanol, isopropanol, ethylene glycol, and the like. The reaction can be carried out at a temperature ranging from about 50°C to about 150°C.

[0165] [Reaction Scheme 4] [ka] In the formula, X is a halogen, and R, R 1 , R 2、 R 4 and Het have the above mentioned meanings.

[0166] Compounds of formula (I) can be prepared from compounds of formula (11) by reaction with a carbonylating reagent such as CDI, diethyl carbonate, phosgene, triphosgene or ethyl chloroformate in the presence of a suitable solvent such as tetrahydrofuran and a suitable base such as an organic or inorganic base selected from, but not limited to, triethylamine or potassium carbonate at a temperature ranging from about 0° C. to about 150° C.

[0167] Compounds of formula (11) can be prepared from compounds of formula (9) via N-alkylation by reacting with compounds of formula (10) where LG is halogen, tosylate, nosylate, or mesylate, preferably halogen. The reaction is carried out in the presence of a suitable base, optionally in the presence of a suitable catalyst such as sodium iodide or tert-butylammonium iodide or tert-butylammonium bromide, and in a suitable solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, acetone, tetrahydrofuran, or acetonitrile, at a temperature ranging from about 0° C. to about 150° C.

[0168] Further, the compound of formula (9) can be obtained by reacting the compound of formula (8) with the compound of formula (7) in the presence of a suitable reagent such as methanesulfonyl chloride, oxalyl chloride, thionyl chloride or a coupling reagent such as EDC.HCl / HOBt, HATU, T3P, in the presence of a suitable base such as an organic or inorganic base selected from, but not limited to, triethylamine, N,N-diisopropylethylamine or potassium carbonate, in a suitable solvent such as N,N-dimethylformamide at a temperature ranging from about 0° C. to about 50° C.

[0169] [Reaction Scheme 4A] [ka] In the formula, X is a halogen, and R, R 1 , R 2、 R 4 , LG and Het have the above mentioned meanings.

[0170] Compounds of formula (I) can be prepared from compounds of formula (11-A) by reaction with a carbonylating reagent such as CDI, diethyl carbonate, phosgene, triphosgene or ethyl chloroformate in the presence of a suitable solvent such as tetrahydrofuran and a suitable base such as an organic or inorganic base selected from, but not limited to, triethylamine or potassium carbonate at a temperature ranging from about 0° C. to about 150° C.

[0171] Compounds of formula (11-A) can be prepared from compounds of formula (9) via N-alkylation by reacting with compounds of formula (10) (wherein LG is halogen, tosylate, nosylate, or mesylate, preferably halogen). The reaction is carried out optionally in the presence of a suitable base, optionally in the presence of a suitable catalyst such as sodium iodide or tert-butylammonium iodide or tert-butylammonium bromide, and in a suitable solvent such as N,N,-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, acetone, tetrahydrofuran, or acetonitrile, at a temperature ranging from about 0° C. to about 150° C.

[0172] Further, the compound of formula (9) can be obtained by reacting the compound of formula (8) with the compound of formula (7) in the presence of a suitable reagent such as methanesulfonyl chloride, oxalyl chloride, thionyl chloride or a coupling reagent such as EDC.HCl / HOBt, HATU, T3P, in the presence of a suitable base such as an organic or inorganic base selected from, but not limited to, triethylamine, N,N-diisopropylethylamine or potassium carbonate, in a suitable solvent such as N,N-dimethylformamide at a temperature ranging from about 0° C. to about 50° C.

[0173] [Reaction Scheme 5] [ka] In the formula, R, R 1 , R 2、 R 4 , LG and Het have the above mentioned meanings.

[0174] Compounds of formula (I) can be prepared from compounds of formula (12) via N-alkylation by reacting with compounds of formula (10). LG is preferably a halogen (preferably iodide, bromide or chloride), tosylate, nosylate or mesylate, and the reaction is carried out according to similar procedures disclosed in Chem.Res.Toxicol.12(1),1999,46-52 and FR2983200, optionally in the presence of a suitable base, optionally in the presence of a suitable catalyst such as sodium iodide, tert-butylammonium iodide or tert-butylammonium bromide, and in the presence of a suitable solvent such as N,N,-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, tetrahydrofuran, acetonitrile or acetone, at a temperature ranging from about 0°C to about 150°C.

[0175] Compounds of formula (12) can be prepared from compounds of formula (9) by reaction with a carbonylating reagent, such as CDI, diethyl carbonate, phosgene, triphosgene or ethyl chloroformate, in the presence of a suitable solvent, such as tetrahydrofuran, and in the presence of a suitable base, such as an organic or inorganic base selected from, but not limited to, triethylamine or potassium carbonate, at a temperature ranging from about 0° C. to about 150° C.

[0176] [Reaction Scheme 6] [ka] In the formula, R, R 1 , R 2、 R 4 , LG and Het have the meanings given above.

[0177] Compounds of formula (IB) can be prepared from compounds of formula (11) by reaction with a thiocarbonylating reagent, such as thio-CDI (1,1'-thiocarbonyldiimidazole) or thiophenyl chloroformate, in the presence of a suitable solvent, such as tetrahydrofuran, dichloromethane, 1,2-dichloroethane or acetonitrile, and a suitable base, such as an organic or inorganic base selected from, but not limited to, triethylamine, pyridine or potassium carbonate, at a temperature ranging from about 0°C to about 150°C.

[0178] [Reaction Scheme 7] [ka] In the formula, R, R 1 , R 2、 R 4 , LG and Het have the meanings given above.

[0179] Compounds of formula (13) can be prepared by treating compounds of formula (7) with Lawesson's reagent in the presence of a suitable solvent such as toluene, chlorobenzene, dioxane or tetrahydrofuran at a temperature ranging from about 50° C. to about 150° C. Alternatively, a similar transformation can be carried out using phosphorus pentasulfide (P2S5) in the presence of a suitable solvent such as toluene, xylene, dioxane or tetrahydrofuran, optionally in the presence of a suitable base such as pyridine or diethylisopropylamine, at a temperature ranging from about 50° C. to about 150° C.

[0180] Compounds of formula (14) can be prepared via N-alkylation by reacting compounds of formula (13) with compounds of formula (10). LG is preferably a halogen (preferably iodide, bromide or chloride) or a tosylate or a nosylate or a mesylate, and the reaction can be carried out optionally in the presence of a suitable base, optionally in the presence of a suitable catalyst such as sodium iodide or tert-butylammonium iodide or tert-butylammonium bromide, and in a suitable solvent such as N,N,-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, tetrahydrofuran, acetonitrile or acetone, at a temperature ranging from about 0° C. to about 150° C.

[0181] Compounds of formula (IC) can be prepared by reacting compounds of formula (14) with a carbonylating reagent, such as CDI, diethyl carbonate, phosgene, triphosgene, ethyl chloroformate or phenyl chloroformate, in the presence of a suitable solvent, such as tetrahydrofuran, dichloromethane, 1,2-dichloroethane or acetonitrile, and in the presence of a suitable base, such as an organic or inorganic base selected from, but not limited to, triethylamine, pyridine or potassium carbonate, at a temperature ranging from about 0° C. to about 150° C.

[0182] Compounds of formula (ID) can be prepared under the same conditions as described for compounds of formula (IC) by using a thiocarbonylating reagent such as thioCDI or thiophenyl chloroformate instead of the carbonylating agent.

[0183] In one embodiment, the present invention provides a method for synthesizing a compound of formula (I), comprising steps selected from a) to e).

[0184] a) Reaction of a compound of formula (III) with a compound of formula (VI), optionally in the presence of a suitable catalyst, a suitable solvent and a suitable base, to obtain a compound of formula (II) or formula (IIB), which is further reacted with a carbonylating or thiocarbonylating reagent in the presence of a suitable solvent and a suitable base to obtain a compound of formula (I). [ka] Or, b) Reacting a compound of formula (III) with a carbonylating or thiocarbonylating reagent in the presence of a suitable solvent and a suitable base to obtain a compound of formula (VIII), which is further reacted with a compound of formula (VI) optionally in the presence of a suitable catalyst, a suitable solvent and a suitable base to obtain a compound of formula (I). [ka] c) Further, the compound of formula (III) can be obtained by reacting the compound of formula (IV) with the compound of formula (V) in the presence of a suitable reagent, a suitable solvent and a suitable base to obtain the compound of formula (III). [ka] Or, d) The compound of formula (I) can be obtained by reacting a compound of formula (IIA) with a compound of formula (IIIA) or (IVB), optionally in the presence of a suitable catalyst, a suitable solvent and a suitable base. [ka] e) reacting a compound of formula (IIIB) with a compound of formula (IVA) in the presence of a suitable catalyst, a suitable solvent and a suitable base to obtain a compound of formula (VA), optionally in the presence of a base, by cyclocondensation reaction of the compound of formula (VA) with a compound of formula (VIA) to obtain a compound of formula (IIA). [ka] wherein X is a halogen; LG is a halogen, tosylate, nosylate, or mesylate; preferably, LG is a halogen, preferably iodide, bromide, or chloride; W 1 , W 2 , R 1 , R 2 , R 4 , R and Het are as defined above.

[0185] An embodiment of the present invention provides compounds of formula (II) and (IIA). [ka] where LG is a halogen (preferably iodide, bromide or chloride), tosylate, nosylate or mesylate. Het, R 4 , R 1 , R 2 , R,W 1 and W 2 is as defined above.

[0186] Yet another embodiment provided by the present invention is a compound of formula (IIB): [ka] In the formula, R is phenyl and C3-C 10 -heterocyclyl, each group optionally containing one or more R x LG is halogen (preferably iodide, bromide or chloride) or tosylate or nosylate or mesylate; Het, R 4 , R 1 , R 2 , R,W 1 and W 2 is as defined above.

[0187] In one embodiment, the present invention provides compounds of formula (I) as set forth in Tables 1-7, which can be prepared according to the methods described above. The following examples are intended to illustrate the present invention and show preferred compounds of formula (I) in the form of compounds of formula (I). Formula (I-1) is a compound of formula (I-2) which is a cyclic or cyclic aryl group having one or more R x may be optionally replaced by [ka]

[0188] Table D shown below shows the variable W of the compound of formula (I-1). 1 , W 2 and Rx This document describes the following: [Table 1] [Table 2] [Table 3] [Table 4] Here, CyPr is cyclopropyl.

[0189] Each of Tables 1 to 7 following Table D above comprises 189 compounds of formula (I-1), 1 , W 2 and R x has the value given in each row of Table 1, and Het is defined in the associated Tables 1-7.

[0190] Thus, compound 1.1 corresponds to a compound of formula (I-1), where W 1 , W 2 and R x is as defined in row 1 of Table 1 and Het is as defined in Table D. Compound 1.2 corresponds to the compound of formula (I-1), where W 1 , W 2 and R x is as defined in row 2 of Table 1, Het is as defined in Table 1, and so on.

[0191] Table 1: This table shows that Het in the formula TIFF2024546050000039.tif2122, R 3 is Cl, and W 1 , W 2 and R x As defined in Table D, 189 compounds 1.1 to 1.189 are disclosed. For example, compound No. 1.1 has the following structure: [ka]

[0192] Table 2: This table shows that Het in the formula TIFF2024546050000041.tif2121, R 3 is CF3 and W 1 , W 2 and R x We disclose 189 compounds 2.1 to 2.189, wherein:

[0193] Table 3: This table shows that Het in the formula TIFF2024546050000042.tif2023, R 3 is Cl, and W 1 , W 2 and R x

[0033] Disclosed are 189 compounds 3.1 to 3.189, wherein:

[0194] Table 4: This table shows that Het in the formula TIFF2024546050000043.tif2122, R 3 is H and W 1 , W 2 and R x Disclosed are 189 compounds 4.1 to 4.189, wherein are as defined in Table D.

[0195] Table 5: This table shows that Het in the formula TIFF2024546050000044.tif2022, R 3 is CF3 and W 1 , W 2 and R x Disclosed are 189 compounds 5.1 to 5.189, wherein are as defined in Table D.

[0196] Table 6: This table shows that Het in the formula TIFF2024546050000045.tif2023, R 3 is Cl, and W 1 , W 2 and R xDisclosed are 189 compounds 6.1 to 6.189, wherein are as defined in Table D.

[0197] Table 7: This table shows that Het in the formula TIFF2024546050000046.tif2024, R 3 is CF3 and W 1 , W 2 and R x Disclosed are 189 compounds 7.1 to 7.189, wherein are as defined in Table D.

[0198] Depending on the nature of the substituents, the compounds of formula (I) and intermediates thereto may exist in pure form or as a mixture of different possible isomers, such as stereoisomers. The different stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, and geometric isomers.

[0199] Depending on the nature of the substituents, the compounds of formula (I) described in the general formula and intermediates thereof can also exist in one or more geometric isomeric forms depending on the relative position (syn / anti or cis / trans) of the substituents. The present invention therefore relates equally to all syn / anti (or cis / trans) isomers and all possible syn / anti (or cis / trans) mixtures, in all proportions. The syn / anti (or cis / trans) isomers can be separated according to the general methods known per se to those skilled in the art.

[0200] In another embodiment, the present invention provides a process for preparing a compound of formula (I) or a salt thereof.

[0201] The compounds of formula (I), including their stereoisomers, salts, and N-oxides, as well as their precursors in the synthetic process, can be prepared by the methods described above. If the individual compounds cannot be prepared directly via the above routes, they can be prepared by derivatization of other compounds (I) or the respective precursors, or by routine modification of the synthetic routes described. For example, in individual cases, certain compounds of formula (I) can be advantageously prepared from other compounds of formula (I) by derivatization, such as ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation, etc., or by routine modification of the synthetic routes described.

[0202] The reaction mixture is worked up in a conventional manner, for example by mixing with water, separating the phases and, if necessary, chromatographic purification of the crude product. Some of the intermediates and final products are obtained in the form of a colorless or slightly brownish viscous oil and are purified or freed from volatile components under reduced pressure and at moderately elevated temperatures. If the intermediates and final products are obtained as solids, purification can also be carried out by recrystallization or digestion.

[0203] If the individual compounds of formula (I) are not obtained by the above routes, they can be prepared by derivatization of other compounds of formula (I). However, if a mixture of isomers is obtained by synthesis, separation is generally not necessary, since the individual isomers may be interconverted during post-treatment or application for use (e.g. under the action of light, acid or base). Such conversions may also occur after use, for example in the treatment of plants in treated plants, or in harmful fungi to be controlled.

[0204] In one embodiment, the present invention provides a composition for controlling or preventing invertebrate pests, comprising a biologically effective amount of a compound of formula (I), an agriculturally acceptable salt, stereoisomer, metal complex, polymorph or N-oxide thereof, and at least one additional component selected from the group consisting of surfactants and adjuvants.

[0205] In another embodiment, the compounds of formula (I) of the present invention are also read as including salts thereof. Exemplary salts include, but are not limited to, hydrochloride, hydrobromide, hydroiodide, acetate, trifluoroacetate, and trifluoromethanesulfonate.

[0206] In yet another embodiment, the composition further comprises at least one additional biologically active and compatible compound selected from a fungicide, an insecticide, a nematicide, an acaricide, a biopesticide, a herbicide, a plant growth regulator, an antibiotic, a fertilizer, or a nutrient.

[0207] In yet another embodiment, the present invention provides a compound of formula (I) or its N-oxide or salt processed into conventional types of agrochemical compositions, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, compresses, 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, pastilles, wettable powders or dusts (WP, SP, WS, DP, DS, etc.), compresses (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticidal articles (e.g., LN), and gel formulations (e.g., GF) for the treatment of plant propagation materials such as seeds. These and further composition types are defined in "Catalogue of Agrochemical Formulation Types and International Code System", Technical Monograph No. 2, 6th Edition, May 2008, CropLife International.

[0208] The compositions are prepared in a known manner, such as described in Mollet and Grubemann, "Formulation Technology", Wiley VCH, Weinheim, 2001, or Knowles, "New Developments in Crop Protection Product Formulation", Agrow Reports DS243, T and F Informa, London, 2005.

[0209] Formulation auxiliaries suitable for preparing the compositions according to the invention are known per se.Examples of suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, moisturizers, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, antifoaming agents, colorants, tackifiers or binders.

[0210] Suitable solvents and liquid carriers are water and organic solvents, for example medium to high boiling mineral oil fractions, such as kerosene, diesel, oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, such as toluene, paraffins, tetrahydronaphthalene, alkylated naphthalenes, alcohols, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol, glycols, dimethyl sulfoxide, ketones, such as cyclohexanone, esters, such as lactates, carbonates, fatty acid esters, γ-butyrolactone, fatty acids, phosphonates, amines, amides, such as N-methylpyrrolidone, fatty acid dimethylamides, and mixtures thereof.

[0211] Suitable solid carriers or fillers are mineral earths such as silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide, polysaccharide powders such as cellulose, starch, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, products of vegetable origin such as grain flour, bark flour, wood flour, nut meals, and mixtures thereof.

[0212] 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 and Detergents", McCutcheon's Directories, Glen Rock, USA, 2008 (International Edition or North American Edition).

[0213] Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, α-olefinsulfonates, ligninsulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinates. Examples of sulfates are sulfates of fatty acids and oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols or fatty acid esters. Examples of phosphates are phosphoric acid esters. Examples of carboxylates are alkylcarboxylates and carboxylated alcohols or alkylphenol ethoxylates.

[0214] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide can be used for alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homeopolymers or copolymers of vinylpyrrolidone, vinyl alcohol or vinyl acetate.

[0215] Suitable cationic surfactants are quaternary surfactants, such as quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetaines and imidazolines. Suitable block polymers are AB or ABA type block polymers containing blocks of polyethylene oxide and polypropylene oxide, or ABC type block polymers containing alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are polyacrylic acid or alkali salts of polyacid copolymers. Examples of polybases are polyvinylamine or polyethyleneamine.

[0216] Suitable adjuvants are compounds that have negligible or no insecticidal activity themselves and improve the biological performance of compound I on the target. Examples are surfactants, mineral or vegetable oils, and other adjuvants. Further examples are described in Knowles, Adjuvants and additives, Agrow Reports DS256, TandF Informa UK, 2006, chapter 5.

[0217] Suitable thickeners are polysaccharides (e.g., xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or not), polycarboxylates, and silicates. Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinone and benzisothiazolinone. Suitable antifreeze agents are ethylene glycol, propylene glycol, urea, and glycerin. Suitable defoamers are silicones, long-chain alcohols, and fatty acid salts. Suitable colorants (e.g., red, blue, or green) are low water-soluble pigments and water-soluble dyes, such as inorganic colorants (e.g., iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (e.g., alizarin, azo, and phthalocyanine colorants). Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological or synthetic waxes, and cellulose ethers.

[0218] Examples of composition types and their preparation are as follows: i) Water-soluble concentrates (SL, LS) 10-60% by weight of compound (I) or its N-oxide or salt and 5-15% by weight of a wetting agent (e.g., alcohol alkoxylate) are dissolved in water and / or a water-soluble solvent (e.g., alcohols) up to 100% by weight. The active substance dissolves upon dilution with water. ii) Dispersible Concentrate (DC) 5-25% by weight of compound (I) or its nitric oxide or salt and 1-10% by weight of a dispersant (e.g., polyvinylpyrrolidone) are dissolved in 100% by weight or less of an organic solvent (e.g., cyclohexanone). Dilution with water gives a dispersion. iii) Emulsifiable concentrate (EC) 15-70% by weight of compound (I) or its nitric oxide or salt and 5-10% by weight of an emulsifier (e.g., calcium dodecylbenzenesulfonate, castor oil ethoxylate) are dissolved in 100% by weight or less of a water-insoluble organic solvent (e.g., aromatic hydrocarbon). An emulsion is obtained by diluting with water. iv) Emulsions (EW, EO, ES) 5-40% by weight of compound (I) or its nitric oxide or salt and 1-10% by weight of an emulsifier (e.g., calcium dodecylbenzenesulfonate, castor oil ethoxylate) are dissolved in 20-40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon). This mixture is introduced into water up to 100% by weight in an emulsifier to obtain a homogeneous emulsion. The mixture is diluted with water to obtain an emulsion. v) Suspensions (SC, OD, FS) In a stirred ball mill, 20-60% by weight of compound (I) or nitrogen oxides or their salts are milled with 2-10% by weight of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylates), 0.1-2% by weight of thickeners (e.g. xanthan gum) and up to 100% by weight of water to obtain a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance. In FS type compositions, up to 40% by weight of a binder (e.g. polyvinyl alcohol) is added. vi) Water-dispersible granules and water-soluble granules (WG, SG) 50-80% by weight of compound (I) or N-oxide or its salt is finely ground with the addition of up to 100% by weight of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylates) and prepared into water-dispersible or water-soluble granules using industrial equipment (e.g. extrusion, spray tower, fluidized bed). By diluting with water, a stable dispersion or solution of the active substance can be obtained. vii) Water-dispersible and water-soluble powders (WP, SP, WS) 50-80% by weight of compound (I) or N-oxide or its salt is ground in a rotor-stator mill with 1-5% by weight of a dispersant (e.g., sodium lignosulfonate), 1-3% by weight of a wetting agent (e.g., alcohol ethoxylate) and up to 100% by weight of a solid carrier, e.g., silica gel. By dilution with water, a stable dispersion or solution of the active substance can be obtained. viii) Gel (GW, GF) 5-25% by weight of compound (I) or the N-oxide or salt thereof is ground in a stirred ball mill and 3-10% by weight of a dispersing agent (e.g. sodium lignosulfonate), 1-5% by weight of a thickener (e.g. carboxymethylcellulose) and up to 100% by weight of water are added to obtain a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance. ix) Microemulsion (ME) 5-20% by weight of Compound (I) or N-oxide or its salt is added to 5-30% by weight of an organic solvent blend (such as fatty acid dimethylamides and cyclohexanone), 10-25% by weight of a surfactant blend (e.g., alcohol ethoxylates and arylphenol ethoxylates) and up to 100% water. The mixture is stirred for 1 hour and a thermodynamically stable microemulsion spontaneously forms. x) Microcapsules (CS) An oil phase containing 5-50% by weight of the compound (I) or N-oxide or its salt, 0-40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and 2-15% by weight of an acrylic monomer (e.g., methyl methacrylate, methacrylic acid, and diol triacrylate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Microcapsules of polymethyl acrylate are produced by radical polymerization initiated by a radical initiator. Alternatively, an oil phase containing 5-50% by weight of the compound (I) of the present invention, 0-40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and an isocyanate monomer (e.g., diphenylmethene-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Addition of a polyamine (e.g., hexamethylenediamine) produces polyurea microcapsules. The monomer is 1-10% by weight. The weight percentage relates to the total CS composition. xi) Dustable powder (DP, DS) 1-10% by weight of compound (I) or an N-oxide or salt thereof is finely ground and intimately mixed with up to 100% by weight of a solid carrier, for example finely divided kaolin. xii) Granules (GR, FG) 0.5-30% by weight of compound I or an N-oxide or a salt thereof is finely ground and mixed with up to 100% by weight of a solid carrier (e.g., a silicate). Granulation is achieved by extrusion, spray drying or in the fluidized bed. xiii) Ultra low volume liquid (UL) 1-50% by weight of compound (I) or an N-oxide or a salt thereof is dissolved in up to 100% by weight of an organic solvent, such as an aromatic hydrocarbon.

[0219] Compositions types i) to xiii) may, if necessary, contain further auxiliaries such as 0.1 to 1% by weight of a bactericide, 5 to 15% by weight of an antifreeze agent, 0.1 to 1% by weight of an antifoam agent and 0.1 to 1% by weight of a colorant.

[0220] In another embodiment, the present invention provides an agrochemical composition comprising a compound of formula (I) which comprises 0.01-95% by weight, preferably 0.1-90% by weight, more preferably 1-70% by weight, especially 10-60% by weight of active substance. The active substance is used with a purity of 90%-100%, preferably 95%-100% (according to NMR spectrum).

[0221] Water-soluble concentrates (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry processing (DS), water-dispersible powders for slurry processing (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually used for the purpose of treating plant propagation material, in particular seeds. The compositions in question, after 2-10-fold dilution, give active substance concentrations of 0.01-60% by weight, preferably 0.1-40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing.

[0222] Methods of applying the compounds of formula (I) or compositions thereof, respectively, to plant propagation material, particularly seeds, include dressing, coating, pelleting, spraying, soaking and in-furrow application of propagation material. Preferably, the compounds of formula (I) or compositions thereof, respectively, are applied to the plant propagation material by methods that do not induce germination, such as seed dressing, pelleting, coating and spraying.

[0223] When used in plant protection, the amount of active substance applied is, depending on the type of effect desired, between 0.001 and 2 kg / ha, preferably between 0.005 and 2 kg / ha, more preferably between 0.02 and 0.9 kg / ha, particularly preferably between 0.05 and 0.75 kg / ha.

[0224] For the treatment of plant propagation material such as seeds, for example by spraying, coating or soaking the seeds, amounts of active substance in the range of 0.1 to 1000 g, preferably 1 to 200 g, more preferably 5 to 150 g, most preferably 10 to 100 g per 100 kilograms of plant propagation material (preferably seeds) are generally required.

[0225] When used in the protection of materials or stored products, the amount of active substance applied depends on the type of application area and the desired effect. Amounts customarily applied in the protection of materials range from 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.

[0226] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients, and other agricultural chemicals (e.g. herbicides, insecticides, fungicides, growth regulators, safety agents, antibiotics, fertilizers, nutrients and biostimulants) can be added to the active substances or compositions containing them as premixes or, if appropriate, cannot be added until just before use (tank mix). These agents can be mixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0227] The user can usually apply the composition according to the invention from a pre-dosing device, a knapsack sprayer, a spray tank, a sprayer, or an irrigation system. Usually, the agrochemical composition is prepared to the desired application concentration with water, buffers, and / or further auxiliaries, and a ready-to-use spray solution or agrochemical composition according to the invention is thus obtained. Usually, 20-6000 liters, preferably 35-1000 liters, more preferably 50-500 liters of ready-to-use spray solution are applied per hectare of agriculturally useful area.

[0228] According to one embodiment, the individual components of the composition according to the invention, such as parts of a kit or parts of a two- or three-component mixture, can be mixed by the user himself in a spray tank, with the aid of further auxiliaries, if necessary.

[0229] The compounds and compositions of the invention are thus agriculturally useful for protecting field crops from phytophagous invertebrate pests, and also non-agronomically useful for protecting other horticultural crops and plants from phytophagous invertebrate pests, including protecting crops and other plants (i.e., both agronomic and non-agronomic) that contain genetic material introduced by genetic engineering (i.e., transgenic) or modified by mutagenesis to provide advantageous traits.

[0230] The compounds of the present invention are characterized by favorable metabolism and / or soil residual patterns and exhibit activity controlling a spectrum of agricultural and non-agricultural invertebrate pests. They are preventively and / or therapeutically valuable active ingredients in the field of pest control, can be used even at low application rates against insecticide-resistant pests such as insects and mites, and are well tolerated by warm-blooded species, fish and plants.

[0231] In the present invention, "invertebrate pest control" means the inhibition of the development (including mortality) of invertebrate pests, thereby causing a significant reduction in feeding damage or other injury or damage caused by the pest. Related expressions are defined similarly. As referred to in the present invention, the term "invertebrate pests" includes arthropods, gastropods and nematodes that are economically important as pests. The term "arthropods" includes insects, mites, spiders, scorpions, centipedes, millipedes, pillbugs and symphylans.

[0232] The term "gastropods" includes snails, slugs and other stem worms. The term "nematodes" includes all helminths, such as roundworms, heartworms, and phytophagous nematodes (Nematoda), trematodes (Nematoda), acanthocephalans, and cestodes (Cestoda). Those skilled in the art will recognize that not all compounds are equally effective against all pests.

[0233] The compounds of the invention are active against economically important agricultural, forestry, greenhouse, nursery, ornamental, turfgrass, food and fiber, public and animal health, home and commercial, household and stored product pests. These include the noctuidae (e.g. cutworms (Spodoptera exigua Hubner), ladybirds (Agrotis ipsilon Hufnagel), cabbage white butterflies (Trichoplusia ni Hubner), cigarette flukes (Heliothis virescens Fabricius), burrowers, stretcher beetles, fall webworms, brittle stars, sponges, cabbage worms and skeletonizers (e.g. European warblers (Ostrinia nubilalis Hubner)), navel oranges (Amyelois transitella Walker), fall webworms (Crambus caliginosellus Clemens), sod webworms (Herpetogramma licarsisalis These include lepidopteran larvae such as armyworms, cutworms, loopers, and heliotines of the Agromyzidae family (e.g., Cydia pomonella Linnaeus, Endopiza viteana Clemens, and Grapholita molesta Busck), leafminers, assassin bugs, seed bugs, and earthworms of the Agromyzidae family (e.g., Plutella xylostella Linnaeus, Pectinophora gossypiella Saunders, and Lymantria dispar Linnaeus), and many other economically important Lepidopteran insects (e.g., Blattella germanica and Blattella germanica (e.g., Blatta orientalis Linnaeus, Blatella asahinai Mizukubo), German cockroach (Blattella gemnanica Linnaeus), German cockroach (Supella longipalpa Fabricius), American cockroach (Periplaneta americana)nymphs and adults of the order Blattella, including cockroaches (British cockroach, Periplaneta brunnea Burmeister, Leucophaea maderae Fabricius), nymphs and adults of the order Coleoptera, including weevils (e.g. Anthonomus grandis Boheman, Lissorhoptrus oryzophilus Kuschel, Sitophilus granarius Linnaeus, Sitophilus oryzae Linnaeus), flea beetles, cucumber beetles, rootworms, leafminers, and leafminers (e.g. Leptinotarsa ​​decemlineata Say, Diabrotica virgifera virgifera LeConte), other beetles of the Scarabaeidae family (e.g. Japanese rhinoceros beetle (Popillia japonica Newman) and western sawtooth beetle (Rhizotrogus majalis Razoumowsky), carpet beetles of the Scolytidae family, nematodes of the Scolytidae family, bark beetles of the Scolytidae family and scarab beetles of the Scolytidae family, as well as adults and larvae of Dermoptera (e.g. European earwig (Forficula auricularia Linnaeus), black earwig (Chelisoches mono Fabricius), adults and nymphs of Hemiptera and Homoptera, aphids of the Hemiptera family, cicadas of the Cicadidae family, leafhoppers of the Cicadidae family (e.g. Empoasca spp.), planthoppers of the families Firgorosidae and Delphacidae, leafhoppers of the family Membranaceae, plantains of the family Psyllidaceae, buntings of the family Emberizidae, aphids of the family Aphididae, phylloxera of the family Phylloxeridae, mealybugs of the family Pseudococcidae, scales of the family Coccidae, Lygaeidae and Margaretidae, house bugs of the family Ploceidae, stink bugs of the family Hemiptera, stink bugs of the family Hemiptera (e.g. Blissusspp.) and other seed insects of the family Coccidae, mealybugs of the family Tetranychus urticae, red worms and cotton bugs of the family Pseudococcidae, and also adults and larvae of the order Acari, such as the Tetranychidae and Tetranychus urticae (e.g. Panonychus ulmi Koch, Tetranychus urticae Koch, Tetranychus mcdanieli McGregor), the Flathead mites of the family Tetranychus urticae (e.g. Brevipalpus lewisi McGregor), the Russet mites of the family Tetranychus scabra and the Sterling mites, as well as other folivorous mites and mites important for human and animal health, i.e. the House mite family Acaridae, the Hair follicle mites of the family Astigmata, the Grain mites of the family Ixodes (e.g. Ixodes scapularis Say), Australian ticks (Ixodes holocyclus Neumann), American dog ticks (Dermacentor variabilis Say), ticks and mites of the families Ixodes, Tetranychus and Sarcoptes, adult and immature insects of the Orthoptera including grasshoppers, locusts and crickets (e.g. migratory grasshoppers (e.g. Melanoplus sanguinipes Fabricius, M. differentialis Thomas), American grasshoppers (e.g. Schistocerca americana Drury), desert locusts (Gryllotalpa spp.), migratory grasshoppers (Locusta migratoria Linnaeus), house crickets (Acheta domesticus Linnaeus), and mole crickets (Acheta domesticus Linnaeus)), leafminers, midges, fruit flies and frit flies (e.g. Oscinella frit Linnaeus), soil maggots, houseflies (e.g. Musca domestica Linnaeus), small flies (e.g. Fannia canicularis Linnaeus, F. femoralis Stein), stable flies (Stomoxys calcitrans Linnaeus, etc.), pine flies, tree flies, blow flies (e.g. ChiysomyaPhonnia spp.), and other pests Musk flies, horse flies (e.g. Tabanus spp.), sawflies (e.g. Gastrophilus spp., Oestrus spp.), cattle larvae (e.g. Panonychus ulmi Koch, Tetranychus urticae Koch, Tetranychus mcdanieli McGregor), deer flies (e.g. Brevipalpus lewisi McGregor), grasshoppers (e.g. migratory grasshoppers (e.g. Melanoplus sanguinipes Fabricius, M. differentialis Thomas), American grasshoppers (e.g. Schistocerca americana Drury), desert locusts (Gryllotalpa spp.), migratory grasshoppers (Locusta migratoria adult and immature Diptera including house crickets (Acheta domesticus Linnaeus), mole crickets (Acheta domesticus Linnaeus) and other Brachycera, mosquitoes (e.g. Aedes spp., Anopheles spp., Culex spp.), blackflies (e.g. Prosimulium spp., Simulium spp.), biting midges, stable flies, small flies and other nematodes; adult and immature Thripida including onion thrips and other leaf-feeding thrips; ants (e.g. Fannia canicularis Linnaeus, F. femoralis Stein), wasps (including carpenter bees), hornets, Japanese yellow wasps and wasps; and termites (Reticulitermes flavipes). Isoptera pests including Formosan Termite (Reticulitermes hesperus Banks), Coptotermes formosanus Shiraki, Incisitermes immigrans Snyder and other economically important termites, as well as silverfish (Lepisma saccharinaThe pests of the order Malophaga, such as the head louse (Pediculus humanus capitis De Geer), body louse (Pediculus humanus Linnaeus), chicken body louse (Menacanthus stramineus Nitszch), dog louse (Trichodectes cams De Geer), Japanese bean louse (Goniocotes gallinae De Geer), sheep louse (Bovicola ovis Schrank), short-nosed cattle louse (Haematopinus eurystemus Nitzsch), long-nosed cattle louse (Linognathus vituli Linnaeus, and other sucking or biting parasitic lice which attack humans and animals; as well as pests of the order Vipera, specifically the rat flea (Xenopsylla cheopis Rothschild), the cat flea (Ctenocephalides felis Bouche), the dog flea (Ctenocephatides canis Curtis), the chicken flea (Ceratophyllus gallinae Schrank), the sticky flea (Echidnophaga gallinacea Westwood), the human flea (Pulex irritans Linnaeus), and other fleas which plague mammals and birds. Other arthropod pests include spiders from the order Araneae, such as the brown recluse spider (Loxosceles reclusa Gertsch and Mulaik) and the black widow spider (Latrodectus mactans Fabricius), and centipedes from the order Centipedes, such as the house centipede (Scutigera coleoptrata Linnaeus), as well as, but are not limited to, economically important agricultural pests (i.e., root-knot nematodes of the genus Meloidogyne, wound nematodes of the genus Pratylenchus, short-root nematodes of the genus Trichodorus, etc.) and animal and human health pests (i.e., Strongylus vulgaris in horses, Toxocara canis in dogs, and others).canis in sheep, Diroflaria immitis Leidy in dogs, Anoplocephala peifoliata in horses, Fasciola hepatica Linnaeus in ruminants, etc. All economically important trematodes, cestodes and roundworms are included in the list of economically important orders of Strongylidae, Ascarida, Oxyurida, Rhabditida, Spirurida and Enomaleurota. Members of the classes Nematoda, Cestoda, Trematoda and Acanthocephala, including members of the orders Priida, also have activity.

[0234] The compounds of the invention are effective against Lepidoptera pests such as Alabama argillacea Hubner (cotton leaf parasite), Archips argyrospila Walker (fruit leaf parasite), A. rosana Linnaeus (European leaf parasite) and other Archips species, Chilo suppressalis Walker (rice stem parasite), Cnaphalocrosis medinalis Guenee (rice leaf parasite), Crambus caliginosellus Clemens (corn root parasite), Crambus teerrellus Zincken (bluegrass parasite), Cydia pomonella Linnaeus (codling moth), Earias insulana Boisduval (spiny bug), Earias vittella Fabricius (spotted bug), Helicoveipa armigera Hbner (fall webworm), Helicoverpa zea Boddie (corn worm), Heliothis virescens Fabricius (tobacco budworm), Herpetogramma licarsisalis Walker (sod webworm), Lobesia botrana Denis and Schiffeπnaller (grapeberry moth), Pectinophora gossypiella Saunders (pink gall midge), Phyllocnistis citrella Stainton (citrus leafminer), Pieris brassicae Linnaeus (large white butterfly), Pieris rapae Linnaeus (small white butterfly), Plutella xylostella Linnaeus (diamondback moth), Spodoptera exigua Hubner (ladybird beetle), Spodoptera litura Fabricius (common cutworm, gregarious caterpillar), Spodoptera frugiperda (common cutworm JEIt is active against the autumn armyworm, Trichoplusia ni Hubner, and tomato leafminer, Tula absoluta Meyrick.

[0235] Compounds of the invention also have significant activity against members of the order Homoptera, including: Acyrthisiplionpisum Harris (pea aphid), Aphis craccivora Koch (cowpea aphid), Aphis fabae Scopoli (black bean aphid), Aphis gossypii Glover (cotton aphid, melon aphid), Aphis pomi De Geer (apple aphid), Aphis spiraecola Patch (parasitic aphid), Aulacorthum solani Kaltenbach (fox aphid), Chaetosiphon fragaefolii Cockerell (strawberry aphid), Diuraphis noxia Kurdjumov / Mordvilko (Russian wheat aphid), Dysaphis plantaginea Paaserini (rosy apple aphid), Eriosoma lanigerum Hausmann (woolly apple aphid), Hyalopterus pruni Geoffroy (mealy plum aphid), Lipaphis erisimi Kaltenbach (bear aphid), Metopolophium dirrhodum Walker (cereal aphid), Macrosipum euphorbiae Thomas (qtato aphid), Myzus persicae Sulzer (peach aphid, peach aphid), Nasonovia ribisnigri Mosley (lettuce aphid), Pemphigus spp.(root and gall aphids), Rhopalosiphum maidis Fitch (corn leaf aphid), Rhopalosiphum padi Linnaeus (bird cherry aphid), Schizaphis graminum Rondani (green stink bug), Sitobion avenae Fabricius (English cereal aphid), Therioaphis maculata Buckton (spotted alfalfa aphid), Toxoptera aurantii, Boyer de Fonscolombe (black citrus aphid) and Toxoptera citiicida Kirkaldy (brown citrus aphid), Adelges spp. (adelgids), Phylloxera devastatrix Pergande (pecan phylloxera), Bemisia tabaci Gennadius (tobacco whitefly, sweet potato whitefly), Bemisia argentifolii Bellows and Perring(silverleaf mosquito), Dialeurodes citri Ashmead(citrus mosquito), Trialeurodes vaporariorum Westwood(household mosquito), Empoasca fabae Harris(potato leafhopper), Laodelphax striatellus Fallen(small springtail), Macrolestes quadrilineatus Forbes(aster leafhopper), Nephotettix cinticeps Uhler(green leafhopper), Nephotettix nigropictus Stal(rice leafhopper), Nilaparvata lugens Stal(brown leafhopper), Peregrinus maidis Ashmead(corn leafhopper), Sogatella furcifera Horvath(white-backed planthopper), Sogatodes orizicola Muir(rice delphid), Typhlocyba pomaria McAfee white apple leafhopper, Erythroneoura spp.(grape leafhopper), Magicidada septendecim Linnaeus (periodic cicada), Icerya purchasi Maskell (cotton-like cushion scale), Quadraspidiotus perniciosus Comstock (San Jose scale), Planococcus citri Risso (citrus mealybug), Pseudococcus spp. (other mealybug complex), Cacopsylla pyricola Foerster (Japanese plantain), Trioza diospyri Ashmead (oyster plantain).

[0236] These compounds also have activity against members of the order Hemiptera, such as: Acrostemum hilare Say (green stink bug), Anasa tristis De Geer (pumpkin bug), Blissus leucopterus leucopterus Say (cotten stink bug), Corythuca gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), Dysdercus suturellus Herrich-S chaffer (cotton stainer), Euchistus servus Leptoglossus corculus Say, Lygus lineolaris Palisot de Beauvois, Nezara viridula Linnaeus, Oebalus pugnax Fabricius, Oncopeltus fasciatus DaEas, Pseudatomoscelis seriatus Reuters, including Say (brown stink bug), Euchistus variolrius Palisot de Beauvois (single stink bug), Graptsthetus spp.

[0237] Other insects controlled by the compounds of formula (I) of the present invention include thrips (e.g., Frankliniella occidentalis Pergande, western flower thrips), Scirthothopscitri Moulton, Sericothrips variabilis Beach, and Thrips tabaci Lindeman, onion thrips, and Coleoptera (e.g., Leptinotarsa ​​decemlineata Say, Colorado potato beetle, Epilachna varivestis Mulsant, Mexican bean beetle, and nematodes of the genera Agriotes, Athous, and Limonius).

[0238] In one embodiment of the invention, the invention provides that the compounds of formula (I) are useful for controlling insects of the genus Thrips, Dipteran and Hemiptera, preferably selected from sucking or piercing insects, such as in particular the following species: Thrips: Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci. Diptera: Aedes aegypti, Aedes albopictus, Aedes aegypti, Anopheles stephensis, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilus intestinalis, Glossina morsitans, Glossina pallis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga spp., Simulium vittatum, Stomoxyscalcitr, Tabanus bovinus, Tabanus atratus, Tabanus lineola, Tabanus similis, Tipula oleracea, Tipula paludosa. Hemiptera, especially aphids: Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphum rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mail, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphismala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantii and Viteus vitifolii.

[0239] The compounds of formula (I), their N-oxides, their isomers, their polymorphs and their salts are also suitable for efficiently combating the following pests: Insects of the order Lepidoptera (Lepidoptera), such as Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Chilo infuscatellus, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Earias vittella, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholita funebrana, Grapholita molesta, Helicoverpa armigera, Helicoverpa virescens, Helicoverpa zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Leucinodes orbonalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosomaneustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Platypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scirpophaga incertulas, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothi pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Spodoptera exigua, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, Zeiraphera canadensis. Beetles (beetles), for example, Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aphthona euphoridae, Athus haemorrhoidalis, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Ctenicera ssp., Diabrotica longicornis, Diabrotica semipunctata, Diabrotica undecimpunctata Diabrotica speciosa, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa ​​decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllobius pyri, Phyllotreta chrysocephala, Phyllophaga sp., Phylopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus, Sitophilus granaria, and flies and mosquitoes (Diptera) such as Aedes aegypti, Aedes albopictus, Aedes aegypti, Anastrepha ludens, Anopheles stephensis, Contarinia sorghicola, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilus intestinalis, Glossina morsitans, Glossina pallis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemya platura, Hypoderma lineata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga haemorrhoidalis, Sarcophaga spp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, Tabanus similis, Tipula oleracea, Tipula paludosa; termites (Isoptera) such as Calotermes flavicollis, Leucotermes flavipus, Heterotermes aureus, Reticulitermes flavipus, Reticulitermes virginicus, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes gracei, Thermes natalensis, and Coptotermes formosanus; cockroaches (Blattaria Blattodea) such as Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuliginosa, Periplaneta australasiae, Blatta orientalis, ants, wasps, wasps, sawflies (Hymenoptera), such as Athalia rosae, Atta cephalotes, Atta capiguara, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Lasius niger, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex californicus, Pheidole megacephala, Dasymutilla occidentalis, Bombus spp., Vespula squamosa, Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolichovespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, Linepithema humile, as well as crickets, grasshoppers, locusts (Orthoptera), such as Acheta domestica, Grylllotalpa grylllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Calliptamus italicus, Chortoicetes terminifera, Locustana pardalina, Araneae such as Latrodectus mactans and Loxosceles reclusa, Fleas (Siphonaptera) such as Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, Nosopsyllus fasciatus, Silverfish, Firebrats (Thysanura) such as Lepisma saccharina, Thermobia domestica, Centipedes (Chilopoda) such as Scutigera oleoptrata, Millipedes (Diplopoda) such as Narceus spp., Earwigs (Dermaptera), e.g. forficula auricularia, Lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon allinae, Menacanthus stramineus, Solenopotes capillatus. Collembola ( Collembola), for example Onychiurus ssp. .

[0240] The compounds of formula (I) according to the invention are also suitable for controlling the following nematodes: Plant parasitic nematodes, such as the root-knot nematodes Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species; the cyst-forming nematodes Globodera rostochiensis and other Globodera species; the Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; the bollworms Anguina species; the stem and leaf nematodes Aphelenchoides species; the nematode Belonolaimus longicaudatus and other Belonolaimus species; the pinewood nematode Bursaphelenchus xylophilus and other Bursaphelenchus spp.; ring nematodes, Criconema spp., Criconemella spp., Criconemoides spp., Mesocriconema spp.; stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus spp.; awl nematodes, Dolichodorus spp.; spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus spp.; sheath and sheath nematodes, Hemicycliophora spp. and Hemicriconemoides spp.; Hirshmanniella spp.; Lance nematodes, Hoploaimus spp.; false root-knot nematodes, Nacobbus spp.; Needle nematodes, Longidorus elongatus and other Longidorus spp.; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi, other Pratylenchus species; Burning nematodes, Radopholus similis, other Pratylenchus species; Reniform nematodes, Rotylenchus robustus, other Rotylenchus species; Scutellonema species; Stubbyroot nematodes, Trichodorus primitivus, other Trichodorus spp., Paratrichodorus spp.; stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, other Tylenchorhynchus spp.; Citrus nematodes, Tylenchulus spp.; Dagger nematodes, Xiphinema spp. and other plant parasitic nematode species.

[0241] The compounds of formula (I) and their salts are also useful in controlling spiders (Arachnida), such as Acarians (mites). For example, Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Eriophyidae spp. Aculus schlechtendali, Phyllolocoptrata oleivora, Eriophyes sheldoni, Tarsonemidae spp. Such as spp. Brevipalpus phoenicis, Tetranychidae spp. Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri and oligonychus pratensis.

[0242] In one embodiment of the invention, the invention provides compounds of formula (I) useful for controlling insects selected from sucking or borer insects such as insects from the genera Thrips, Diptera and Hemiptera, in particular the following species: Thrips genus: Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci. Diptera: Aedes aegypti, Aedes albopictus, Aedes aegypti, Anopheles stephensis, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilus intestinalis, Glossina morsitans, Glossina pallis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga spp., Simulium vittatum, Stomoxyscalcitr, Tabanus bovinus, Tabanus atratus, Tabanus lineola, Tabanus similis, Tipula oleracea, Tipula paludosa. Hemiptera, especially aphids: Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphum rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mail, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphismala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantiiand, and Viteus vitifolii.

[0243] In one preferred embodiment, the compounds of formula (I) of the present invention are particularly useful for controlling, for example, Frankliniella occidentalis, Empoasca fabae, Nilaparvata lugens, Nephotettix virescens, Aphis gossypii, Myzus persicae, Bemisia tabaci and Bemisia argentifolii.

[0244] In one embodiment, the present invention provides a composition comprising a biologically effective amount of a compound of formula (I) and at least one additional biologically active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers, nutrients and biostimulants.The compounds used in the composition and in combination with the compound of formula (I) are also called active compatible compounds.

[0245] Known and reported fungicides, insecticides, nematicides, acaricides, biological pesticides, herbicides, plant growth regulators, antibiotics and nutrients can be combined with at least one compound of formula (I) of the present disclosure. For example, fungicides, insecticides, nematicides, acaricides, biological pesticides, herbicides, plant growth regulators, antibiotics, fertilizers, nutrients and biostimulants disclosed and reported in WO2016156129 and / or WO2017153200 can be combined with at least one compound of formula (I) of the present disclosure.

[0246] The fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients reported in WO2016156129 and / or WO2017153200 are hereby incorporated by reference as non-limiting examples for combination with at least one compound of formula (I) of the present disclosure.

[0247] In particular, the compounds of the present invention may be mixed with at least one further biologically active compatible compound (mixing partner) including, but not limited to, insecticides, fungicides, nematicides, bactericides, acaricides, growth regulators such as root stimulants, chemical fungicides, semi-chemicals, repellents, attractants, pheromones, feeding stimulants, other biologically active compounds or entomopathogenic bacteria, viruses or fungi to form multi-component insecticides which provide an even broader spectrum of agricultural usefulness.

[0248] Examples of such biologically active compounds or agents / mixing partners with which the compounds of formula (I) of the present invention can be combined / formulated are disclosed in WO2019072906A1 (pages 27-37).

[0249] In one embodiment, biological agents for combination with the compounds of formula (I) of the present invention include Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, and naturally occurring genetically modified viral insecticides and insectivorous fungi including members of the Baculoviridae family.

[0250] In certain embodiments, combination with other invertebrate pest control compounds or agents that have a similar control spectrum but a different mode of action is particularly advantageous for resistance management.Thus, the composition of the present invention can further comprise a biologically effective amount of at least one additional invertebrate pest control compound or agent that has a similar control spectrum but a different mode of action.Contacting a plant or a plant locus that has been genetically modified to express a plant protection compound (e.g., protein) with a biologically effective amount of the compound of the present invention also provides a broader plant protection spectrum and is advantageous for resistance management.

[0251] In one embodiment of the present invention, the biologically effective amount of the compound of formula (I) in the composition is in the range of 0.1 to 99% by weight based on the total weight of the composition, preferably in the range of 5 to 50% by weight based on the total weight of the composition.

[0252] The invention further provides a method of combating invertebrate pests, the method comprising contacting the invertebrate pest, its habitat, breeding ground, food supply, plants, seeds, soil, the area, material or environment in which the invertebrate pest is growing or may grow, or the material, plant, seed, soil, surface or space to be protected from pest attack or infestation, with a biologically effective amount of a compound of formula (I) or an agriculturally acceptable salt, stereoisomer, metal complex, polymorph, or N-oxide thereof and / or compositions or combinations thereof.

[0253] Control of invertebrate pests and protection of agricultural, horticultural and specialty crops, animal and human health is achieved by applying one or more of the compounds of the present invention in an effective amount to the pest's environment, including agricultural and / or non-agricultural infestation sites, to the area to be protected, or directly to the pest to be controlled. Thus, the present invention further includes a method for the control of foliage and soil-dwelling invertebrates and protection of agricultural and / or non-agricultural crops, which method comprises contacting the invertebrate or its environment with a biologically effective amount of one or more of the compounds of the present invention, or a composition comprising at least one such compound, or a composition comprising at least one such compound and at least one additional biologically active compound or agent. The preferred method of contact is by spraying. Alternatively, a granular composition comprising the compound of the present invention can be applied to the plant's foliage or soil. The compounds of the present invention are effective for delivery via plant uptake by contacting the plant with a composition comprising the compound of the present invention applied as a soil drench of a liquid formulation, a granular formulation to the soil, a nursery box treatment, or a transplant drench. Other methods of contact include application of the compounds or compositions of the present invention by direct and residual spraying, aerial spraying, seed coating, microencapsulation, systemic incorporation, bait, ear tag, bolus, fog, fumigant, aerosol, dust and many others.

[0254] The compounds of the invention can be incorporated into baits or devices such as traps that are consumed by invertebrates. Granules or baits containing 0.01-5% active ingredient, 0.05-10% moisture retaining agent, and 40-99% vegetable flour are effective in controlling soil insects at very low application rates, especially at doses of active ingredient that are lethal by ingestion rather than direct contact. The compounds of the invention can be applied in their pure state, but most often application is in a formulation containing one or more compounds with suitable carriers, diluents, and surfactants, possibly in combination with food, depending on the intended end use. The preferred method of application involves spraying an aqueous dispersion or refined oil solution of the compound. Combinations with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance the effectiveness of the compounds.

[0255] The application rate required for effective control (i.e., the "biologically effective amount") depends on factors such as the species of invertebrate to be controlled, the pest's life cycle, life stage, its size, location, time of year, the host crop or animal, feeding behavior, mating behavior, ambient humidity, temperature, and the like. Under normal circumstances, an application rate of about 0.01 to 2 kg of active ingredient per hectare is sufficient to control pests in agricultural ecosystems, although as little as 0.0001 kg per hectare may be sufficient, or as much as 8 kg may be necessary. In non-agricultural applications, effective application rates range from about 1.0 to 50 mg per square meter, although as little as 0.1 mg per square meter may be sufficient, or as much as 150 mg per square meter may be necessary. Those skilled in the art can readily determine the biologically effective amount required for the desired level of invertebrate pest control.

[0256] The term "animal pests" includes arthropods, gastropods and nematodes. Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, especially insects. Insects that are particularly associated with crops are typically referred to as crop pests.

[0257] Animal pests, i.e., arthropods, plants, soil or water in which the plants grow, can be contacted with the compounds of formula (I), their N-oxides and salts or compositions containing them by any application method known in the art. As used herein, "contacting" includes both direct contact (applying the compound / composition directly to the animal pest or plant, typically to the leaves, stems or roots of the plant) and indirect contact (applying the compound / composition to the locus of the animal pest or plant).

[0258] The compounds of the present invention or pesticidal compositions containing them can be used to protect growing plants and crops from attack or infestation by animal pests, particularly insects and mites, by contacting the plants / crops with an insecticidally effective amount of at least one compound of the present invention. The term "crops" refers to both growing and harvested crops.

[0259] The compounds of the present invention are also suitable for use in combating or controlling animal pests.Therefore, the present invention also relates to a method of combating or controlling animal pests, which comprises contacting an animal pest, its habitat, breeding ground, or food supply, or plant propagation materials such as crops, plants, seeds, or soil, or areas, materials, or environments in which an animal pest is growing or may grow, with an insecticidally effective amount of the compounds of the present invention.

[0260] In one embodiment, the invention provides a method for protecting crops from attack or infestation by invertebrate pests comprising contacting the crops with a biologically effective amount of a compound or composition, isomer, polymorph, N-oxide or salt thereof of the invention.

[0261] The compounds of the invention are used as such or in the form of a composition by treating the insects or plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms, with an insecticidally effective amount of the active compound. Application can be carried out both before and after the infestation by insects of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms.

[0262] In one embodiment, the present invention provides a method for protecting a seed from soil insects and protecting the seedling roots and shoots from soil and foliage insects comprising contacting the pre-sown and / or pre-germinated seed with a compound or composition of the present invention, an N-oxide or salt thereof.

[0263] The present invention further provides a method for treating or protecting an animal from parasitic infestation or infection comprising orally, topically or parenterally administering or applying to the animal a biologically effective amount of a compound of formula (I) or a composition of the invention, an isomer, polymorph, N-oxide or a veterinarily acceptable salt thereof.

[0264] When used to treat crops, the application rate of the compounds of the invention (application of an effective dose) may range from 1 to 2000 g ai, and for agricultural or horticultural crops may range from 10 to 500 g per hectare, more preferably from 50 to 200 g per hectare.

[0265] The compounds and compositions of the present invention are particularly useful for the control of numerous insects on a variety of cultivated plants such as cereals, root crops, oil crops, vegetables, spices, ornamentals, e.g., durum and other wheat seeds, barley, oats, rye, corn (fodder and sugar / sweet corn and field corn), soybeans, oil crops, canola, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugar beet, fodder beet, eggplant, potato, grass, turf, lawn, forage grass, tomato, leek, pumpkin / squash, cabbage, iceberg lettuce, pepper, cucumber, melon, brassica, melon, bean, pea, garlic, onion, carrot, potato, sugar cane, tobacco, grapes, petunias, geranium / pelargonium, pansy, and impatiens.

[0266] In particular, the compounds or compositions of the present invention are useful in the protection of cereals, maize, sorghum, bajra, rice, soybean, oilseeds and other legumes, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbits, oil plants, tobacco, coffee, tea, cocoa, sugar beet, sugarcane, cotton, potato, tomato, onion, pepper, ornamentals, rapeseeds, fruiting vegetables, leafy vegetables, rapeseeds, and other vegetables.

[0267] The compounds of the invention are effective both through contact (via soil, glass, walls, bed nets, carpets, plant parts or animal parts) and through ingestion (bait or plant parts).

[0268] The compounds of the invention may also be applied against non-crop invertebrate pests such as ants, termites, wasps, flies, mosquitoes, crickets or cockroaches. For use against said non-crop pests, the compounds of the invention are preferably used in a bait composition.

[0269] As used herein, the term "non-crop pests" refers to pests that are specifically associated with non-crop targets, such as ants, termites, wasps, flies, mites, mosquitoes, crickets, or cockroaches.

[0270] The baits may be liquid, solid or semi-solid formulations (e.g. gels). Solid baits can be formed into various shapes and forms suitable for the respective application, such as granules, blocks, sticks, discs, etc. Liquid baits can be filled into various devices, such as open containers, spray devices, droplet sources, or evaporation sources, to ensure proper application. Gels can be based on aqueous or oily matrices and can be formulated for the specific application in terms of adhesion, water retention or aging properties.

[0271] The bait used in the composition is a product that is attractive enough to entice insects such as ants, termites, wasps, flies, mosquitoes, crickets, or cockroaches to eat it. This attractiveness can be manipulated by using feeding stimulants or sex pheromones. Feeding stimulants are selected, for example, from animal and / or vegetable proteins (meat, fish or blood meal, insect parts, egg yolk), fats and oils of animal and / or vegetable origin, or mono-, oligo- or polysaccharides, in particular sucrose, lactose, fructose, dextrose, glucose, starch, pectin, or molasses or honey, but are not limited thereto. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as feeding stimulants. Sex pheromones are known to be more specific to insects. Specific pheromones are described in the literature and are known to the skilled person.

[0272] For use in bait compositions, the typical content of active ingredient is from 0.001 to 15% by weight of active compound, preferably from 0.001 to 5% by weight.

[0273] Formulation of the compounds of the invention as aerosols (eg spray cans), oil sprays or pump sprays are highly suitable for non-professional users to control pests such as flies, fleas, ticks, mosquitoes or cockroaches. Aerosol formulations preferably consist of the active compound, solvents such as lower alcohols (e.g. methanol, ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffinic hydrocarbons (e.g. kerosene) having a boiling range of about 50 to 250° C., aromatic hydrocarbons such as dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, toluene, xylene, water, as well as auxiliaries such as sorbitol monooleate, oleyl ethoxylates with 3 to 7 moles of ethylene oxide, emulsifiers such as fatty alcohol ethoxylates, fragrance oils such as ether oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, stabilizers such as sodium benzoate if appropriate, amphoteric surfactants, lower epoxides, triethyl orthoformate, and, if necessary, propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases. The oil spray formulation differs from the aerosol formulation in that no propellant is used.

[0274] Oil spray formulations differ from aerosol formulations in that no propellant is used. When used in a spray composition, the active ingredient content is 0.001-80% by weight, preferably 0.01-50% by weight, and most preferably 0.01-15% by weight.

[0275] The compounds of the present invention and their respective compositions can also be used in mosquito coils, fumigation coils, smoke cartridges, vaporizer plates or long-term vaporizers, as well as moss papers, moss pads or other heat-independent vaporizer systems.

[0276] The method of controlling infectious diseases transmitted by insects (malaria, dengue, yellow fever, lymphatic filariasis, leishmaniasis, etc.) using the compounds of formula (I) and their respective compositions also includes the treatment of surfaces of sheds and houses, aerial spraying and impregnation of curtains, tents, clothing, mosquito nets, tsetse fly traps, etc. Insecticidal compositions for application to fibres, wovens, knitted goods, nonwovens, netting materials or foils and tarpaulins preferably comprise a mixture comprising an insecticide, optionally a repellent and at least one binder. Suitable repellents include, for example, pyrethroids not used for insect control, such as N,N-diethyl-meta-toluamide (DEET), N,N-diethylphenylacetamide (DEPA), 1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine, (2-hydroxymethylcyclohexyl)acetic acid lactone, 2-ethyl-1,3-hexanediol, indalone, methylneodecanamide (MNDA), (+ / -)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysanthemate (esbiothrin), limonene, eugenol, repellents derived from or identical to plant extracts, such as (+)-eucamalol (1), (-)-1-epi-eucamalol or the like, such as Eucalyptus maculata, Vitex rotundifolia, Cymbopogan Crude plant extracts from plants such as Cymbopogan citratus (lemongrass), Cymopogan nartdus (citronella). Suitable binders are selected, for example, from vinyl esters of aliphatic acids (vinyl acetate, versatate, etc.), acrylic and methacrylic esters of alcohols such as butyl acrylate, 2-ethylhexyl acrylate, methyl acrylate, polymers and copolymers of mono- and diethylenically unsaturated hydrocarbons such as styrene, and aliphatic dienes such as butadiene.

[0277] Impregnation of curtains and mosquito nets is generally carried out by dipping the textile material into an emulsion or dispersion of the insecticide or by spraying the netting.

[0278] The compound of the present invention and its composition can be used to protect not only wood materials such as trees, wooden fences, and sleepers, buildings such as houses, barns, and factories, but also building materials, furniture, leather, textiles, vinyl products, electric wires, cables, etc. from ants and / or termites, and to prevent the damage caused by ants and termites to agricultural crops or humans (such as intrusion into houses and public facilities).The compound of the present invention can be applied not only to the surrounding soil surface or underfloor soil to protect wood materials, but also to the surface of underfloor concrete, underfloor pillars, beams, plywood, lumber products such as furniture, wood products such as particle boards and half boards, coated electric wires, vinyl sheets, insulation materials such as polystyrene foam, etc.

[0279] When applied to ants that are harmful to agricultural crops, wooden houses, or humans, the compounds of the present invention are applied to the agricultural crops or the surrounding soil, or directly to the ant nest or the like.

[0280] The preferred application method in the field of crop protection is application to the leaves of plants (foliar application), the frequency and rate of application can be selected to match the risk of infestation by the pest in question. Alternatively, the active ingredient can reach the plant via the root system by watering the plant locus with a liquid composition (systemic action) or by incorporating the active ingredient in solid form at the plant locus, for example in the form of granules, into the soil (soil application). In the case of rice crops, such granules can be metered into flooded rice fields.

[0281] <Digital Technology> The compounds of the present invention can be used in combination with models incorporated into computer programs for, for example, site-specific crop management, satellite agriculture, precision agriculture or precision agriculture. Such models support site-specific management of agricultural sites using data from various sources such as soil, weather, crops (e.g., variety, growth stage, plant health), weeds (e.g., type, growth stage), diseases, pests, nutrients, water, moisture, biomass, satellite data, yield, etc., with the aim of optimizing profitability, sustainability and environmental protection. In particular, such models help optimize agricultural decisions, control the accuracy of pesticide spraying, and record the work carried out.

[0282] As an example, if the model models a pest infestation and calculates that a threshold has been reached at which it is recommended to apply a compound of the present invention to the crop plant, the compound of the present invention can be applied to the crop plant according to an appropriate dose regime.

[0283] Commercially available systems that include agricultural models include, for example, FieldScript™ from The Climate Corporation, Xarvio™ from BASF, and AGLogic™ from John Deere.

[0284] The compounds of the present invention can also be used in combination with smart spraying devices, such as spot spraying or precision spraying devices attached to or housed in agricultural vehicles, such as tractors, robots, helicopters, airplanes, unmanned aerial vehicles (UAVs), such as drones. Such devices usually include input sensors (e.g., cameras, etc.) and a processing unit configured to analyze the input data and provide a decision based on the analysis of the input data to specifically and precisely apply the compounds of the present invention to crop plants (respectively weeds). The use of such smart spraying devices usually also requires a location system (e.g., a GPS receiver) to localize the recorded data and to guide or control the agricultural vehicle. It also requires a geographic information system (GIS) to represent the information on a clear map, and a suitable agricultural vehicle to perform the required agricultural activities, such as spraying.

[0285] As an example, pests can be detected from images captured by a camera. Pests can be identified and / or classified based on the images. Such identification and / or classification can utilize image processing algorithms. Such image processing algorithms can utilize machine learning algorithms such as trained neural networks, decision trees, and can utilize artificial intelligence algorithms. In this way, the compounds described herein can be applied only when necessary.

[0286] <Seed treatment> The present invention further provides seeds comprising a compound of the present invention, particularly in an amount ranging from about 0.0001% to about 1% by weight of the seed before treatment.

[0287] The compounds according to the invention are also suitable for the treatment of seeds to protect them against pests, especially soil-dwelling and acarine pests, and to protect the roots and shoots of the resulting plants against soil and foliar pests.

[0288] The compounds of the present invention are particularly useful for protecting seeds from soil pests, and for protecting the roots (termites and nematodes) and shoots of the resulting plants from soil pests and foliar pests.Protection of the roots and shoots of the resulting plants is preferred.More preferred is protection of the shoots of the resulting plants from stinging and sucking insects, most preferred is protection from aphids, jaccids, thrips and whiteflies.

[0289] Thus, the present invention includes a method for protecting seeds from insects, particularly soil-borne insects, and for protecting seedling roots and shoots from insects, particularly soil-borne and foliar insects, which comprises contacting the seeds with a compound of the present invention before sowing and / or after germination. Particularly preferred is a method for protecting the roots and shoots of plants, more preferably a method for protecting the shoots of plants from piercing and sucking insects, and most preferably a method for protecting the shoots of plants from aphids.

[0290] The term "seed" encompasses all types of seeds and plant propagation materials, including, but not limited to, true seeds, seed pieces, suckers, corms, bulbs, fruits, tubers, grains, cuttings, cut shoots, and the like, and in a preferred embodiment refers to true seeds.

[0291] 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.

[0292] The present invention also includes seeds coated or containing the active compound of formula (I).Seeds can be coated with seed coating compositions containing the compounds of the present invention.For example, seed coating compositions reported in EP3165092, EP3158864, WO2016 / 198644, WO2016 / 039623, WO2015 / 192923, CA2940002, US2006 / 150489, US2004 / 237395, WO2011 / 028115, EP2229808, WO2007 / 067042, EP1795071, EP1273219, WO2001 / 078507, EP1247436, NL1012918 and CA2083415.

[0293] The term "coated and / or containing" generally means that the active ingredient is mostly present on the surface of the propagation product when applied, although depending on the application method, most or a small part of the ingredient may penetrate into the propagation product. When the propagation product is (re)planted, it may absorb the active ingredient along with moisture.

[0294] Suitable seeds are cereal, root crop, oil crop, vegetable, spice and ornamental seeds, such as durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet corn and field maize), soybean, oil crops, rapeseed, cotton, sunflower, banana, rice, oilseed rape, turnip rape, sugar beet, fodder beet, eggplant, potato, grass, turf, lawn, fodder grass, tomato, leek, pumpkin / squash, cabbage, iceberg lettuce, pepper, cucumber, melon, rapeseed, melon, beans, peas, garlic, onion, carrot, tubers such as potato, sugarcane, tobacco, grapes, petunia, geranium / pelargonium, pansy and impatiens.

[0295] Furthermore, the compounds of the invention can be used to treat the seed of plants which have been made resistant to the action of herbicides or fungicides or insecticides by breeding, including genetic engineering methods.

[0296] For example, the compounds of the invention can be used to treat the seeds of plants which are resistant to herbicides from the group consisting of sulfonylureas, imidazolinones, glufosinate ammonium or glyphosate-isopropylammonium and similar active substances (see, for example, EP 242236, EP 242246) (WO 92 / 00377) (EP 257993, US 5013659) or can be used in transgenic crop plants, such as cotton, which have the ability to produce Bacillus thuringiensis toxins (Bt toxins) which make the plant resistant to certain pests (EP 142924, EP 193259).

[0297] Furthermore, the compounds of the present invention can be used to treat the seeds of plants with modified properties compared to existing plants, which can be produced, for example, by traditional breeding methods and / or mutant generation or by recombinant procedures.For example, many cases of recombinant modification of crop plants have been described, for example, for the purpose of modifying the starch synthesized in the plant (for example, WO92 / 11376, WO92 / 14827, WO91 / 19806), or of recombinant modification of transgenic crop plants with modified fatty acid composition (WO91 / 13972).

[0298] Seed treatment applications of the compounds of the invention are carried out by dusting or spraying the seeds before sowing of the plants and before emergence of the plants.

[0299] Particularly useful compositions for seed treatment are, for example: A. Soluble concentrates (SL, LS) B. Emulsions (EW, EO, ES) C. Suspension (SC, OD, FS) D. Water-dispersible granules and water-soluble granules (WG, SG) E. Water-dispersible and water-soluble powders (WP, SP, WS) F. Gel formulation (GF) G. Dusty powders (DP, DS)

[0300] Conventional seed treatment formulations include, for example, thick flow agents FS, solutions LS, powders for dry treatment DS, water-dispersible powders WS for slurry treatment, water-soluble powders SS, emulsions ES and EC, gel formulations GF, etc. These formulations can be applied to seeds diluted or undiluted. Application to seeds is carried out before sowing, directly on the seeds, or after the seeds have germinated.

[0301] In one embodiment, the FS formulation is used for seed treatment. Typically, the FS formulation may contain 1-800 g / l of active ingredient, 1-200 g / l of surfactant, 0-200 g / l of antifreeze agent, 0-400 g / l of binder, 0-200 g / l of pigment, and up to 1 liter of solvent, preferably water.

[0302] In particular, FS formulations of the compounds of the invention for seed treatment usually contain 0.1-80% by weight (1-800 g / l) of active ingredient, 0.1-20% by weight (1-200 g / l) of at least one surfactant, for example 0.05-5% by weight of a wetting agent and 0.5-15% by weight of a dispersing agent, up to 20% by weight (for example 5-20% by weight) of an antifreeze agent, 0-15% by weight (for example 1-15% by weight) of a pigment and / or dye, 0-40% by weight (for example 1-40% by weight) of a binder (sticker / adhesive), optionally up to 5% by weight (for example 0.1-5% by weight) of a thickener, optionally 0.1-2% by weight of an antifoaming agent, and optionally preservatives such as biocides, antioxidants, etc. (for example in amounts of 0.01-1% by weight), and up to 100% by weight of fillers / excipients.

[0303] The seed treatment formulation may further comprise a binder and optionally a colorant.

[0304] Binders can be added to improve the adhesion of active substances on the seeds after treatment.Suitable binders are homo- and copolymers from alkylene oxides such as ethylene oxide or propylene oxide, polyvinyl acetate, polyvinyl alcohol, polyvinylpyrrolidone and their copolymers, ethylene-vinyl acetate copolymers, acrylic homo- and copolymers, polyethyleneamines, polyethyleneamides and polyethylenepyrimidines, polysaccharides such as cellulose, tylose and starch, polyolefin homo- and copolymers such as olefin / maleic anhydride copolymers, polyurethanes, polyesters, polystyrene homo- and copolymers.

[0305] Optionally, a colorant can also be included in the formulation. Suitable colorants or dyes for seed treatment formulations are Rhodamine B, CI Pigment Red 1 12, CI Solvent Red 1, Pigment Blue 15:4, Pigment Blue 15:3, Pigment Blue 15:2, Pigment Blue 15:1, Pigment Blue 80, Pigment Yellow 1, Pigment Yellow 13, Pigment Red 1:12, Pigment Red 48:2, Pigment Red 48:1, Pigment Red 57:1, Pigment Red 53:1, Pigment Orange 43, Pigment Orange 34, Pigment Orange 5, Pigment Green 36, Pigment Green 7, Pigment White 6, Pigment Brown 25, Basic Violet 10, Basic Violet 49, Acid Red 51, Acid Red 52, Acid Red 14, Acid Blue 9, Acid Yellow 23, Basic Red 10, Basic Red 108.

[0306] An example of a gelling agent is carrageen (Satiagel®).

[0307] In the treatment of seeds, the application rate of the compound of the invention is generally 0.1 g to 5 kg per 100 kg of seeds, preferably 1 g to 1 kg per 100 kg of seeds, more preferably 1 g to 200 g per 100 kg of seeds, in particular 5 g to 150 g per 100 kg of seeds, and 10 g to 100 g per 100 kg of seeds. Thus, the invention also provides seeds comprising a compound of formula (I) or an agriculturally useful salt of formula (I) as defined herein. The amount of the compound of formula (I) or an agriculturally useful salt thereof is generally 0.1 g to 5 kg per 100 kg of seeds, preferably 1 g to 1 kg per 100 kg of seeds, in particular 1 g to 200 g per 100 kg of seeds, and in particular 5 g to 150 g per 100 kg of seeds, and 10 g to 100 g per 100 kg of seeds.

[0308] <Animal Health> The present invention also provides agricultural and / or veterinary compositions comprising at least one compound of formula (I).

[0309] In one embodiment, the invention provides the use of a compound of formula (I), an agriculturally acceptable salt, stereoisomer, metal complex, polymorph or N-oxide, composition or combinations thereof to combat invertebrate pests or animal parasites in agricultural and / or horticultural crops.

[0310] The compounds of formula (I), their N-oxides and / or veterinarily acceptable salts are also particularly suitable for use in combating parasites in and on animals.

[0311] The present invention also provides compositions for combating parasites in and on animals comprising an insecticidally effective amount of at least one compound of formula (I), an N-oxide or a veterinarily acceptable salt thereof, and an acceptable carrier.

[0312] The present invention also provides a method for the treatment, control, prevention and protection of an animal from parasitic infestation and infection, which method comprises orally, topically or parenterally administering or applying to the animal an insecticidally effective amount of a compound of the present invention or a composition comprising same.

[0313] The invention also provides a method for preparing a composition for the treatment, control, prevention or protection of an animal from infestation or infection by a parasite which comprises an insecticidally effective amount of a compound of the invention or a composition comprising same.

[0314] The activity of compounds against agricultural pests does not suggest their suitability for controlling endo- and ectoparasites in and on animals, which requires, for example, low dosages for oral administration, non-emetic dosages, metabolic compatibility with animals, low toxicity, and safe handling. Surprisingly, it has now been found that the compounds of the present invention are suitable for combating endo- and ectoparasites in and on animals.

[0315] The compounds of the present invention and compositions containing them are preferably used to control and prevent parasitism and infection in animals, including warm-blooded animals (including fish).They are suitable for controlling and preventing parasitism and infection in mammals such as cattle, sheep, pigs, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, buffalo, donkeys, fallow deer and reindeer, and also suitable for controlling and preventing parasitism and infection in fur-bearing animals such as mink, chinchilla and raccoon, birds such as chicken, goose, turkey and duck, and fish such as fresh and saltwater fishes such as trout, carp and eel.

[0316] The compounds of the present invention and compositions containing them are preferably used to control and prevent parasites and infections in domestic animals such as dogs or cats.

[0317] Infestations in warm-blooded animals and fish include, but are not limited to, lice, body lice, mites, nose bot, pubic lice, face lice, musk flies, flies, meat fly larvae, chiggers, black flies, mosquitoes and fleas.

[0318] The compounds of the invention and compositions containing them are suitable for the systemic and / or non-systemic control of ecto- and / or endoparasites. They may be active against all or some stages of development.

[0319] The compounds of the invention are particularly useful for combating ectoparasites.

[0320] The compounds of the invention are particularly useful for combating parasites of the following orders and species: Fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides cams, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus, cockroaches (Blattaria Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuliginosa, Periplaneta australasiae, and 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, Chrysomiya bezziana, Chrysomiya hominivorax, Chrysomiya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pi pi ens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilusintestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorroidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, Tabanus similis, Lice (Phthiraptera), Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae、Menacanthus stramineus、Solenopotes capillatus etc.turicata and parasitic mites (Mesostigmata), such as Ornithonyssus bacoti and Dermanyssus gallinae, Actinedida (Prostigmata) and Acaridida (Astigmata), such as Acarapis spp., Cheyleella spp., Ornithocheyletia spp., Myobia, Psorergates, Demodex, Trombicula, Listrophorus, Acarus, Tyrophagus, Caloglyphus, Hypodectes, Pterolichus, P genus soroptes, genus Chorioptes, genus Otodectes, genus Sarcoptes, genus Notoedres, genus Knemidocoptes, genus Cytodites, genus Laminosioptes, Bugs(Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, the genera Triatoma, Rhodnius, Panstrongylus, and Arilus critatus, the Anopurida such as Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp., the Mallophagida (suborders Arnblycerina and Ischnocerina) such as Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.

[0321] Nematodes and Trichinella (Trichosyringida) are, for example, the Trichinella family (Trichinella genus), (Trichinella family), Trichinella, Trichinella, Rhabditida, for example, Rhabditis, Strongyloides, Helicepharobus, Nematoda, for example, Strongylus, Ancylostoma, Necator americanus, Bunostomum spp. (hookworms), Trichostrongylus spp., Haemonchus contortus, Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Esophagostomia spp., Stephanurus dentatus, Orlanus spp., Chavertia spp., Stephanurus dentatus, Tracheostomia spp., Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muerarius capillaris, Protostrongylus spp., Angiostrongylus spp., Parellaphostrongylus spp., Aleurostrongylus abstrusus and Dioctophyma renale, Intestinal roundworms (roundworms) such as Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis, Toxocara canis, Toxascaris leonine, Skrjabinema spp. and Oxyuris equi, Camallanida, e.g. Dracunculus medinensis, Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp.a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi and Habronema spp., Thorny head worms(Acanthocephala), Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp., Planarians (Platelmintes), Flukes (Trematoda), Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria a lata, Paragonimus spp. and Nanocyetes spp., Cercomeromorpha, in particular cestodes (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. .

[0322] The compounds of formula (I) and compositions containing them are particularly useful for controlling pests from the orders Diptera, Vipera and Ixodida.

[0323] In one embodiment, the invention provides the use of compounds of formula (I) and compositions containing them to combat mosquitoes.

[0324] In one embodiment, the invention provides the use of compounds of formula (I) and compositions containing them for combating flies.

[0325] In one embodiment, the invention provides the use of compounds of formula (I) and compositions containing them to combat fleas.

[0326] The use of the compounds of the invention and compositions containing them to combat mites is yet another embodiment of the invention.

[0327] The compounds of the invention are also particularly useful for combating endoparasites (nematodes, spinocerephagida, planarians).

[0328] In one embodiment, the administration of the compounds of the invention can be done both prophylactically and therapeutically.

[0329] In another embodiment, administration of the compounds of the invention is performed orally, topically / transdermally or parenterally, either directly or in a suitable formulation.

[0330] For oral administration to warm-blooded animals, the compounds of the invention can be formulated as animal feed, animal feed premix, animal feed concentrate, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. Additionally, the compounds of the invention can be administered to animals in their drinking water. For oral administration, the dosage form selected should provide the animal with 0.01 to 100 mg / kg animal body weight / day of the compound of the invention, preferably 0.5 to 100 mg / kg animal body weight / day.

[0331] Alternatively, the compounds of the invention can be administered to animals parenterally, for example, by intraluminal, intramuscular, intravenous or subcutaneous injection. The compounds of the invention can be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds of the invention can be formulated into an implant for subcutaneous administration, or the compounds of the invention can be administered transdermally to animals. For parenteral administration, the dosage form selected should provide the animal with 0.01 to 100 mg / kg of animal body weight / day of the compound of the invention.

[0332] The compounds of the present invention can also be applied topically to animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations, and in the form of ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 to 5,000 ppm, preferably 1 to 3,000 ppm, of the compounds of the present invention. Additionally, the compounds of the present invention can be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.

[0333] Suitable formulations are solutions such as oral solutions, concentrates for oral administration after dilution, solutions for application to the skin or body cavities, injection formulations and gels, emulsions and suspensions for oral or transdermal administration, semisolid formulations, formulations in which the active compound is treated with an ointment base, oil-in-water or water-in-oil emulsion base, solid formulations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules, aerosols, inhalants and shaped articles containing the active compound.

[0334] Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and adding additional ingredients, such as acids, bases, buffer salts, preservatives, solubilizers, etc. as needed. The solution is filtered and filled aseptically.

[0335] Suitable solvents are physiologically acceptable solvents such as water, ethanol, butanol, benzyl alcohol, glycerol, alkanols such as propylene glycol, polyethylene glycol, N-methylpyrrolidone, 2-pyrrolidone, and mixtures thereof.

[0336] The active compound can, if desired, be dissolved in physiologically acceptable vegetable or synthetic oils suitable for injection.

[0337] Suitable solubilizers are solvents which promote the dissolution of the active compound in the main solvent or prevent its precipitation, such as polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan esters.

[0338] Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n-butanol.

[0339] Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the concentration to be used. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, and do not require aseptic technique.

[0340] Solutions for use on the skin may be dripped, spread, rubbed, sprinkled or sprayed.

[0341] Solutions for application on the skin are prepared according to the state of the art and as described above for injection solutions, without the need for aseptic technique.

[0342] Further suitable solvents are polypropylene glycol, phenylethanol, phenoxyethanol, esters such as ethyl acetate or butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers, for example dipropylene glycol monomethyl ether, ketones such as acetone, methyl ethyl ketone, aromatic hydrocarbons, vegetable and synthetic oils, dimethylformamide, dimethylacetamide, transcutol, solketal, propylene carbonate, and mixtures thereof.

[0343] It may be advantageous to add thickeners during preparation. Suitable thickeners are inorganic thickeners such as bentonite, colloidal silicic acid, aluminum monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates.

[0344] Gels are applied or spread on the skin or introduced into body cavities. They are prepared by treating a solution prepared in the same manner as for an injection solution with sufficient thickening agent to obtain a transparent substance having an ointment-like consistency. The thickening agents used are those described above.

[0345] Pour-on formulations are injected or sprayed onto a limited area of ​​the skin, allowing the active compound to penetrate the skin and act systemically. Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in a suitable skin-compatible solvent or solvent mixture. If necessary, other auxiliaries such as colorants, bioabsorption promoters, antioxidants, light stabilizers, adhesives, etc. are added.

[0346] Suitable solvents are, for example, water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, ketones such as diethylene glycol monobutyl ether, acetone, methyl ethyl ketone, cyclic carbonates such as propylene carbonate, ethylene carbonate, aromatic and / or aliphatic hydrocarbons, vegetable oils or synthetic oils, dimethylformamide, dimethylacetamide, methylpyrrolidone, n-alkylpyrrolidones such as n-butylpyrrolidone or octylpyrrolidone, N-methylpyrrolidone, 2-pyrrolidone, 2-,2-dimethyl-4-oxymethylene-1,3-dioxolane or glycerol formal.

[0347] Suitable colorants are, for example, all colorants approved for use on animals which can be dissolved or suspended.

[0348] Suitable absorption promoters are, for example, spreading oils such as dimethyl sulfoxide, isopropyl myristate, dipropylene glycol pelargonate, silicone oils and their copolymers with polyethers, fatty acid esters, triglycerides or fatty alcohols.

[0349] Suitable antioxidants are, for example, sulfites or metabisulfites, such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole or tocopherol.

[0350] A suitable light stabilizer is, for example, novantisolic acid. Suitable adhesives are, for example, cellulose derivatives, starch derivatives, polyacrylates or natural polymers such as alginates, gelatin, etc. The emulsions can be administered orally, transdermally or as injections. The emulsions are either water-in-oil or oil-in-water type.

[0351] These are prepared by dissolving the active compound in either the hydrophobic or hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, where appropriate, other auxiliaries such as colorants, absorption promoters, preservatives, antioxidants, light stabilizers, viscosity-increasing substances, etc.

[0352] Suitable hydrophobic phases (oils) are liquid paraffin, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, etc., synthetic triglycerides such as caprylic / capric acid biglyceride, chain lengths C1 to C6. 12 triglyceride mixtures with vegetable fatty acids or other specially selected natural fatty acids, partial glyceride mixtures of saturated or unsaturated fatty acids which may also contain hydroxyl groups, mono- and diglycerides of Cs-do fatty acids, fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol perargonate, etc., with chain length C 16 ~C 18 Esters of medium-chain-length branched-chain fatty acids with saturated fatty alcohols, isopropyl myristate, isopropyl palmitate, chain length C 12 ~C 18 Caprylic / capric esters of saturated fatty alcohols such as isopropyl stearate, oleyl, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters such as synthetic duck fat, dibutyl phthalate, diisopropyl adipate, and ester mixtures related to the latter, fatty alcohols such as isotridecyl alcohol, fatty acids such as 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol, and oleic acid, and mixtures thereof. Suitable hydrophilic phases are water, alcohols such as propylene glycol, glycerol, sorbitol, and mixtures thereof.

[0353] Suitable emulsifiers are, for example, nonionic surfactants, such as polyethoxylated castor oil, polyethoxylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ethers, amphoteric surfactants, such as disodium N-lauryl-p-iminodipropionate or lecithin.

[0354] Suitable anionic surfactants are, for example, sodium lauryl sulfate, fatty alcohol ether sulfates, mono / dialkyl polyglycol ether orthophosphate monoethanolamine salts. A suitable cationic active surfactant is cetyltrimethylammonium chloride.

[0355] Suitable further auxiliaries are, for example, substances which increase the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes, colloidal silicic acid or mixtures of the abovementioned substances.

[0356] Suspensions can be administered orally or topically / dermally. Suspensions are prepared by suspending the active compound in a suspension, where appropriate with the addition of other auxiliaries such as wetting agents, colorants, bioabsorption promoters, preservatives, antioxidants, light stabilizers, etc.

[0357] Liquid suspending agents are all homogeneous solvents and solvent mixtures.

[0358] Suitable wetting agents (dispersing agents) are the emulsifying agents mentioned above.

[0359] Other auxiliaries that may be mentioned are those mentioned above.

[0360] Semi-solid formulations can be administered orally or topically / dermally. They differ from the suspensions and emulsions described above only in that they are more viscous.

[0361] To prepare solid formulations, the active compound is mixed with suitable excipients and, if necessary, with the addition of auxiliaries, brought into the desired form.

[0362] Suitable excipients are all physiologically acceptable solid inert substances. These can be inorganic or organic substances. Inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, hydrogen carbonates, aluminum oxide, titanium oxide, silicic acid, clayey earth, precipitated or colloidal silica, phosphates. Organic substances are, for example, food and feed, such as sugar, cellulose, milk powder, animal meals, cereal meals and chips, starch, etc.

[0363] Suitable auxiliaries are the abovementioned preservatives, antioxidants and / or colorants.

[0364] Other suitable auxiliaries are lubricants and glidants such as magnesium stearate, stearic acid, talc, bentonite, disintegration-promoting substances such as starch or cross-linked polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyrrolidone, and dry binders such as microcrystalline cellulose.

[0365] Generally, "parasiticidally effective amount" means the amount of active ingredient required to achieve an observable effect on growth, including the effect of killing, retarding, preventing and eliminating, destroying, or otherwise reducing the occurrence and activity of the target organism. The parasiticidally effective amount may vary with the various compounds / compositions used in the present invention. The parasiticidally effective amount of the composition also varies with the general conditions, such as the desired parasiticidal effect and duration, the target species, and the method of application. The compositions that can be used in the present invention generally contain about 0.001-95% of the compound of the present invention.

[0366] In general, it is preferred to apply the compounds of the invention in a total amount of 0.5 to 100 mg / kg per day, preferably 1 to 50 mg / kg per day. The ready-to-use formulations contain the compounds acting against parasites, preferably ectoparasites, in an amount 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. The formulations diluted before use contain the compounds acting against ectoparasites in an amount of 0.5 ppm to 90% by weight, preferably 1 to 50% by weight. Furthermore, the formulations contain the compounds of the invention acting against endoparasites in an amount of 10 ppm to 2% by weight, preferably 0.05 to 0.9% by weight, particularly preferably 0.005 to 0.25% by weight.

[0367] In one embodiment, a composition containing a compound of the invention is applied to the skin / topically.

[0368] In another embodiment, topical application is in the form of a shaped article containing the compound, such as collars, medallions, ear tags, bands for fastening on body parts, and adhesive strips and foils.

[0369] In general, it is preferred to apply a solid formulation, which releases a total amount of the compound of the invention in the range of 10-300 mg / kg, preferably 20-200 mg / kg, most preferably 25-100 mg / kg body weight of the administered animal over a period of three weeks.

[0370] Thermoplastics and flexible plastics, as well as elastomers and thermoplastic elastomers, are used to prepare molded articles.Suitable plastics and elastomers are polyvinyl resins, polyurethanes, polyacrylates, epoxy resins, cellulose, cellulose derivatives, polyamides and polyesters, which are fully compatible with the compounds of the present invention.A detailed list of plastics and elastomers and the preparation procedure of molded articles are described, for example, in WO2003 / 086075.

[0371] Positive crop response The compounds of the present invention not only effectively control insect and acarid pests, but also exhibit positive crop responses such as plant growth promoting effects such as enhanced root growth, increased tolerance to drought, high salt, high temperature, cold, frost or light exposure, improved flowering, improved nutrient utilization (e.g. improved nitrogen assimilation), improved plant product quality, increased number of productive tillers, increased resistance to fungi, insects, pests, etc., resulting in increased yields. EXAMPLES

[0372] [Chemical Examples] The following examples illustrate, without limiting the invention, the methods and processes for making the compounds of the present invention, and include the best mode contemplated by the inventors for carrying out the invention.

[0373] <Example 1> Synthesis of 8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione acetate (compound 10) [ka] Step-1: 6-(((6-chloropyridin-3-yl)methyl)amino)pyrimidine-2,4(1H,3H)-dione To a stirred suspension of 6-chloropyrimidine-2,4(1H,3H)-dione (1.0 g, 6.82 mmol) and (6-chloropyridin-3-yl)methanamine (1.17 g, 8.19 mmol) in n-butanol (10 mL) was added N,N-diisopropylethylamine (2.4 mL, 13.65 mmol) at 25° C. The reaction mixture was stirred at 150° C. for 1.5 h under microwave conditions. The resulting solid was filtered, washed with ethyl acetate (3×20 mL) and dried under reduced pressure to give 6-(((6-chloropyridin-3-yl)methyl)amino)pyrimidine-2,4(1H,3H)-dione (1.5 g, 5.9 mmol, 87% yield). 1H-NMR (400MHz, DMSO-d6) δ10.20(d,J=20.2Hz,2H), 8.37(d,J=1.8Hz,1H), 7.78(dd,J=8.3,2.4Hz,1H), 7.51( d,J=8.3Hz,1H), 6.67(t,J=6.0Hz,1H), 4.40(d,J=1.5Hz,1H), 4.31(d,J=5.8Hz,2H)ESIMS(m / z)252.95(MH)+.

[0374] Step-2: 8-(((6-chloropyridin-3-yl)methyl)pyrimidine[2,3-d]pyrimidine-2,4(3H,8H)-dione acetate To a stirred suspension of 6-(((6-chloropyridin-3-yl)methyl)amino)pyrimidine-2,4(1H,3H)-dione (7.5 g, 29.7 mmol) in acetic acid (100 mL) was added 1,1,3,3-tetraethoxypropane (7.85 g, 35.6 mmol) and the resulting reaction mixture was stirred at 80° C. for 4 h. After completion of the reaction, the reaction mixture was cooled to 25° C. and concentrated under reduced pressure to give the crude product, which was washed with ethyl acetate (3×30 mL) and dried under reduced pressure to give 8-((6-chloropyridin-3-yl)methyl)pyrimidine[2,3-d]pyrimidine-2,4(3H,8H)-dione acetate (7.6 g, 21.8 mmol, 73% yield). 1 H-NMR(400MHz, DMSO-d6)(m, 3H)δ11.94(s, 1H), 10.93(s, 1H), 8.65(dd,J=6.6,1.7Hz,1H), 8.51(d,J=2.1Hz,1H), 8.41(dd,J=7.2,1.7Hz,1H), 7. 88(dd,J=8.3,2.4Hz,1H), 7.52(dd,J=8.3,0.6Hz,1H), 6.96(dd,J=7.3,6.7Hz,1H), 5.60(d,J=17.7Hz,2H), 1.91-1.86;ESIMS(m / z)288.9(MH)+.

[0375] <Example 2> Synthesis of ethyl 2-(8-((6-chloropyridin-3-yl)methyl)-2,4-dioxo-4,8-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)acetate (compound 8) [ka] To a stirred mixture of 8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione acetate (300 mg, 1.04 mmol) and ethyl 2-bromoacetate (0.148 mL, 1.25 mmol) in N,N-dimethylformamide (4 mL) was added potassium carbonate (1.0 g, 7.27 mmol). The reaction mixture was stirred at 25° C. for 24 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane (5 mL) and filtered. The filtrate was purified by silica gel column chromatography to give ethyl 2-(8-((6-chloropyridin-3-yl)methyl)-2,4-dioxo-4,8-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)acetate (61 mg, 0.163 mmol, 15.66% yield). 1 H-NMR(400MHz,DMSO-d6)δ8.77(dd,J=6.4,1.7Hz,1H),8.54-8.51(m,2H),7.90(dd,J=8.3,2.4Hz,1H),7.52(d,J=8.3H) z,1H),7.08(t,J=7.0Hz,1H),5.63(s,2H),4.57(s,2H),4.14-4.08(m,2H),1.22-1.16(m,3H);ESIMS(m / z)374.9(MH)+.

[0376] <Example 3> Synthesis of 3-butyl-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione (compound 13) [ka] To a stirred suspension of 8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione acetate (Step-2 of Example 1) (300 mg, 1.04 mmol) in N,N-dimethylformamide (4 mL) was added sodium hydride (83 mg, 2.08 mmol) at 0° C. The resulting mixture was stirred at 50° C. for 0.5 h, followed by addition of 1-bromobutane (214 mg, 1.56 mmol) at 50° C. Stirring was continued at the same temperature for 6 h. After completion of the reaction, the reaction mixture was cooled to 25° C. and excess sodium hydride was quenched by adding a few drops of water. The resulting reaction mixture was diluted with dichloromethane (5 mL) and centrifuged. The resulting liquid was concentrated under reduced pressure to obtain a crude product, which was then purified by silica gel column chromatography to obtain 3-butyl-8-((6-chloropyridin-3-yl)methyl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione (57 mg, 0.165 mmol, yield 15.91%). 1 H-NMR(400MHz,DMSO-d6)δ8.68(dd,J=6.6,1.7Hz,1H),8.52(d,J=2.2Hz,1H), 8.46(dd,J=7.5,1.8Hz,1H),7.89(dd,J=8.3,2.4Hz,1H),7.52(d,J=8.1Hz,1H) ,7.01(t,J=7.0Hz,1H),5.60(s,2H),3.82(t,J=7.3Hz,2H),1.53-1.46(m,2H), 1.27(td,J=14.9,7.6Hz,2H),0.88(t,J=7.3Hz,3H);ESIMS(m / z)344.90(MH)+.

[0377] <Example 4> Synthesis of 8-((6-chloropyridin-3-yl)methyl)-3-phenylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione (compound 53) [ka] Step-1: 2-Amino-N-phenylnicotinamide To a stirred solution of 2-aminonicotinic acid (0.5 g, 3.62 mmol) in N,N-dimethylformamide (5 mL) were added EDC.HCl (1.04 g, 5.43 mmol), HOBt (0.83 g, 5.43 mmol), N,N-diisopropylethylamine (1.90 ml, 10.86 mmol) and aniline (0.494 mL, 5.43 mmol) successively at 25° C., and the resulting mixture was stirred at 25° C. for 16 h. After completion of the reaction, the reaction mixture was poured into water (100 mL). The aqueous layer was extracted with ethyl acetate (2×200 mL), and the combined organic layers were washed with saturated aqueous brine solution (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel to give the desired product as a solid (0.672 g, 3.15 mmol, 87% yield). 1 H-NMR (400MHz, DMSO-d6) δ10.12(s, 1H), 8.12(dd,J=4.8,1.8Hz,1H), 8.02(dd,J=7.7,1.8Hz,1H), 7.69-7.66(m , 2H), 7.36-7.31(m, 2H), 7.11-7.07(m, 1H), 6.94(s, 2H), 6.65(dd,J=7.7,4.8Hz,1H);ESIMS(m / z)213.95(MH)+.

[0378] Step-2: 2-Amino-1-((6-chloropyridin-3-yl)methyl)-3-(phenylcarbamoyl)pyridine-1-iodide To a stirred solution of 2-amino-N-phenylnicotinamide (0.44 g, 2.04 mmol) in N,N-dimethylformamide (5 mL) was added 2-chloro-5-(chloromethyl)pyridine (0.40 g, 2.45 mmol) and sodium iodide (0.46 g, 3.07 mmol) at 25° C. The reaction mixture was stirred at 90° C. for 16 h. After completion of the reaction, the reaction mixture was cooled to 25° C. and concentrated under reduced pressure to obtain the crude product, which was purified by column chromatography on silica gel to obtain the desired product as a solid (0.532 g, 1.570 mmol, 77% yield). 1H-NMR (400MHz, DMSO-d6) δ10.84(s, 1H), 9.00(s, 2H), 8.55(dd,J=7.6,1.2Hz,1H), 8.48-8.41(m, 2H), 7.78(dd,J=8.3,2.7Hz,1H ), 7.70(d,J=7.6Hz,2H), 7.60(d,J=8.3Hz,1H), 7.40-7.36(m, 2H), 7.18-7.14(m, 2H), 5.70(s, 2H);ESIMS(m / z)338.85(MH-I)+.

[0379] Step-3: 8-((6-chloropyridin-3-yl)methyl)-3-phenylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione (compound 53) To a stirred solution of 2-amino-1-((6-chloropyridin-3-yl)methyl)-3-(phenylcarbamoyl)pyridine-1-iodide (512 mg, 1.51 mmol) in tetrahydrofuran (6 mL) at 25 °C, triethylamine (0.42 mL, 3.02 mmol) was added at 25 °C, followed by CDI (490 mg, 3.02 mmol). The reaction mixture was stirred at 100 °C for 4-5 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and poured into water (20 mL). The aqueous layer was extracted with ethyl acetate (2 × 80 mL) and the combined organic layers were washed with saturated aqueous salt solution (2 × 20 mL), dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure to give a crude solid, which was purified by flash chromatography using a mixture of dichloromethane in methanol as eluent to give the desired product as a solid (150 mg, 0.411 mmol, 27.2% yield). 1 H-NMR (400MHz, DMSO-d6) δ8.74(dd,J=6.6,1.7Hz,1H), 8.56(d,J=2.2Hz,1H), 8.49(dd,J=7.3,1.7Hz,1H), 7.94(dd,J=8.3,2.4Hz,1H), 7.56-7. 54(m, 1H), 7.44(td, J=6.7, 1.5Hz, 2H), 7.38-7.34(m, 1H), 7.19-7.17(m, 2H), 7.05(dd,J=7.2,6.5Hz,1H), 5.65(s, 2H);ESIMS(m / z)364.95(MH)+

[0380] <Example 5> Synthesis of 8-((2-chlorothiazol-5-yl)methyl)-3-(1-methyl-1H-pyrazol-4-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione (compound 89) [ka] Step-1: 2-Amino-N-(1-methyl-1H-pyrazol-4-yl)nicotinamide The title compound was prepared from 2-aminonicotinic acid (1.0 g, 7.24 mmol) and 1-methyl-1H-pyrazol-4-amine (2.0 g, 20.63 mmol) according to the reaction conditions described in step-1 of Example 4 (2.68 g, 12.34 mmol, 90% yield). 1 H-NMR (400MHz, DMSO-d6) δ10.30(s, 1H), 8.10(dd,J=4.9,1.8Hz,1H), 8.00-7.97(m, 2H), 7.52(d ,J=0.6Hz,1H), 7.05(s, 2H), 6.63(dd,J=7.8,4.7Hz,1H), 3.81(s, 3H);ESIMS(m / z)218.00(MH)+.

[0381] Step-2: 2-amino-1-((2-chlorothiazol-5-yl)methyl)-3-((1-methyl-1H-pyrazol-4-yl)carbamoyl)pyridin-1-ium iodide The title compound was prepared from 2-amino-N-(1-methyl-1H-pyrazol-4-yl)nicotinamide (0.80 g, 3.68 mmol) and 2-chloro-5-(chloromethyl)thiazole (0.68 g, 4.05 mmol) according to the reaction conditions described in step-2 of Example 4 (1.10 g, 2.307 mmol, 62% yield). 1H-NMR (400MHz, DMSO-d6) δ11.00(s, 1H), 9.26(s, 2H), 8.49-8.45(m, 2H), 8.00(s, 1H), 7.88(s, 1H), 7.60(d,J=0.6Hz,1H), 7.15(t,J=7.0Hz,1H), 5.75(s, 2H), 3.82(s, 3H);ESIMS(m / z)348.95(MH-I)+.

[0382] Step-3: 8-((2-chlorothiazol-5-yl)methyl)-3-(1-methyl-1H-pyrazol-4-yl)pyrido[2,3-d]pyrimidine-2,4(3H,8H)-dione (compound 89) The title compound was prepared from 2-amino-1-((2-chlorothiazol-4-yl)methyl)-3-((1-methyl-1H-pyrazol-5-yl)carbamoyl)pyridine-1-iodide (0.50 g, 1.05 mmol) according to the reaction conditions described in step-3 of Example 4 (0.150 g, 0.40 mmol, 38% yield). 1 H-NMR (400MHz, DMSO-d6) δ8.73(dd,J=6.6,1.7Hz,1H), 8.49(dd,J=7.3,1.7Hz,1H), 7.88(s, 1H), 7.84(d,J=0.5 Hz,1H), 7.46(d,J=0.6Hz,1H), 7.06(dd,J=7.5,6.5Hz,1H), 5.70(s, 2H), 3.86(s, 3H);ESIMS(m / z)374.85(MH)+.

[0383] <Example 6> Synthesis of 3-(4-bromophenyl)-8-((6-chloropyridin-3-yl)methyl)-2-thioxo-2,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one (Compound 191) [ka] Step-1: 2-Amino-N-(4-bromophenyl)nicotinamide To a stirred solution of 2-aminonicotinic acid (1.3 g, 9.41 mmol) in N,N-dimethylformamide (12 mL) at 25° C., EDC.HCl (2.71 g, 14.12 mmol), HOBt (2.162 g, 14.12 mmol), N,N-diisopropylethylamine (4.93 mL, 28.2 mmol) and 4-bromoaniline (1.78 g, 10.35 mmol) were added sequentially. The resulting reaction mixture was stirred at 25° C. for 16 h. After completion of the reaction, the reaction mixture was poured into water (250 mL) and the aqueous layer was extracted with ethyl acetate (2×200 mL). The combined organic layers were separated, washed with brine solution (2×150 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude compound, which was purified by washing with a mixture of dichloromethane and pentane to give a solid 2-amino-N-(4-bromophenyl)nicotinamide (2.50 g, 8.56 mmol, 91% yield). ESIMS(m / z)293.90(MH)+

[0384] Step-2: 2-amino-3-((4-bromophenyl)carbamoyl)-1-((6-chloropyridin-3-yl)methyl)pyridine-1-iodide To a stirred solution of 2-amino-N-(4-bromophenyl)nicotinamide (1 g, 3.42 mmol) in N,N-dimethylformamide (10 mL) was added 2-chloro-5-(chloromethyl)pyridine (0.61 g, 3.77 mmol) and sodium iodide (0.77 g, 5.13 mmol) at 25° C., and the resulting reaction mixture was stirred at 90° C. for 16 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give the crude compound, which was purified by column chromatography on silica gel to give 2-amino-3-((4-bromophenyl)carbamoyl)-1-((6-chloropyridin-3-yl)methyl)pyridine-1-iodide as a solid (1.47 g, 2.69 mmol, 79% yield). 1H-NMR (400MHz, DMSO-d6) δ10.92(s, 1H), 8.95(s, 2H), 8.54-8.52(m, 1H), 8.45-8.41(m, 2H), 7.76(dd,J=8.4,2.6Hz ,1H), 7.68(dt,J=9.3,2.4Hz,2H), 7.61-7.56(m, 3H), 7.17(t,J=7.0Hz,1H), 5.63(s, 2H);ESIMS(m / z)418.45(MH)+

[0385] Step-3: 3-(4-bromophenyl)-8-((6-chloropyridin-3-yl)methyl)-2-thioxo-2,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one To a stirred solution of 2-amino-3-((4-bromophenyl)carbamoyl)-1-((6-chloropyridin-3-yl)methyl)pyridine-1-iodide (0.65 g, 1.19 mmol) in tetrahydrofuran (6 mL) was added triethylamine (0.331 ml, 2.372 mmol) and di(1H-imidazol-1-yl)methanethione (0.53 g, 2.37 mmol) at 25° C. The reaction mixture was stirred at 100° C. for 5 hours. After completion of the reaction, the reaction mixture was poured into water (200 mL) and extracted with ethyl acetate (2×200 mL). The combined organic layers were washed with 1N HCl (100 mL), brine solution (2×100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude compound which was purified by silica gel column chromatography to give the desired product 3-(4-bromophenyl)-8-((6-chloropyridin-3-yl)methyl)-2-thioxo-2,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one as a solid (0.150 g, 0.326 mmol, 27.5% yield). 1H-NMR (400MHz, DMSO-d6) δ8.96(dd,J=6.4,1.5Hz,1H), 8.67(d,J=2.1Hz,1H), 8.56(dd,J=7.5,1.7Hz,1H), 8.06(dd,J=8.4,2.6Hz,1H), 7.62 (dd,J=6.6,2.0Hz,2H), 7.56(d,J=8.3Hz,1H), 7.24(dd,J=7.5,6.6Hz,1H), 7.11(dd,J=6.6,2.0Hz,2H), 5.71(s, 2H)ESIMS(m / z)460.85(MH)+

[0386] The following compounds in Table A were obtained following analogous procedures described in Examples 1 to 6 using the appropriate starting materials. [Table 5] [Table 6] [Table 7] [Table 8] [Table 9] [Table 10] [Table 11] [Table 12] [Table 13] [Table 14] [Table 15] [Table 16]

Table 17

Table 18

Table 19

Table 20

Table 21

Table 22

Table 23

Table 24

Table 25

Table 26

Table 27

Table 28

Table 29

Table 30

Table 31

Table 32

Table 33

[0387] As described herein, the compounds of formula (I) exhibit insecticidal activity against a number of insects that attack important agricultural crops. The compounds of the present invention were evaluated for their activity as described in the following tests.

[0388] [Biological Examples] Example A: Bemisia tabaci The test used the leaf dip method, where the required amount of compound was weighed and dissolved in a tube containing a solvent solution. The tube was vortexed at 2000 rpm for 90 minutes to ensure proper mixing, after which the mixture was diluted with 0.01% Triton-X solution to the desired test concentration. Brinal leaves were dipped into the compound solution for 10 seconds, dried in the shade for 20 minutes, and then placed abaxial side up on 4 ml of 1% agar solution in each container cap. A known number of newly emerged adult whiteflies were collected using a modified aspirator and released into perforated containers containing the caps containing the treated leaves. The containers were placed in a plant growth chamber at 25°C and 70% relative humidity. Observations of dead, moribund, and live adults were recorded 72 hours after release. Mortality was calculated as dead and moribund adults combined and compared to untreated controls. Compounds 32, 53, 58, 79, 80, 81, 82, 84, 87, 88, 89, 94, 95, 96, 101, 102, 103, 104, 105, 106, 107, 108, 109, 112, 113, 11 4, 115, 116, 117, 118, 119, 120, 123, 124, 125, 126, 127, 130, 135, 138, 139, 140, 144, 145, 147, 150, 154, 156, 1 58, 159, 164, 167, 168, 169, 170, 171, 188, 189, 191, 198, 199, 200, 201, 202, 206, 207, 208, 209, 210, 213, 216, 223, 224, 225, 227, 228, 231, 232, 233, 234, 235, 236, 238, 242, 243, 244, 246, and 247 recorded mortality rates of 70% or more at 300 PPM.

[0389] Example B: Myzus persicae The leaf immersion method was used for the test, where the required amount of compound was weighed and dissolved in a tube containing a solvent solution. The tube was vortexed at 2000 rpm for 90 min to ensure proper mixing, and the mixture was diluted to the desired test concentration with 0.01% Triton-X solution. Pepper leaves were immersed in the compound solution for 10 s, dried in the shade for 20 min, and then placed abaxial side up in a single cell of a bioassay tray containing 4 ml of solid 1% agar solution. A known number of third instar nymphs collected in a Petri dish were released into the cell containing the treated leaf, and the cell was covered with a perforated lid to allow for good aeration. The tray was placed in a plant growth chamber at 25°C and 70% relative humidity. Dead, moribund, and live nymphs were observed 72 h after release. Mortality was calculated by combining dead and moribund nymphs and comparing them to untreated controls. Compounds 1, 2, 3, 4, 11, 14, 15, 16, 17, 22, 23, 24, 26, 28, 29, 32, 53, 56, 58, 59, 64, 68, 73, 76, 79, 80, 81, 82, 83, 84, 87, 88, 89, 92, 94, 95, 96, 98, 101 , 102, 103, 104, 105, 106, 107, 108, 109, 111, 113, 114, 115, 116, 117, 1 18, 119, 120, 123, 124, 125, 126, 127, 135, 138, 139, 140, 141, 150, 151 , 154, 159, 160, 168, 169, 172, 174, 178, 179, 186, 187, 188, 189, 190, 191, 193, 195, 196, 197, 198, 199, 201, 203, 204, 205, 207, 208, 210, 211, 212, 213, 214, 216, 217, 218, 222, 223, 225, 226, 228, 231, 232, 233, 234, 235, 236, 238, 239, 240, 242, 243, 244, 246, and 247 recorded mortality rates of over 70%.

[0390] Example C: Brown planthopper The seedling immersion method was used for the test, where the required amount of compound was weighed and dissolved in a tube containing a solvent solution. The tube was vortexed at 2000 rpm for 90 min to mix properly, and then diluted with 0.01% Triton-X solution. Paddy seedlings were immersed in the compound solution for 10 s, dried in the shade for 20 min, and then placed in glass test tubes with the roots kept submerged. Fifteen third-instar larvae were released into each test tube and placed in a plant growth chamber at 25°C and 75% relative humidity. Dead, moribund, and live larvae were observed 72 h after release. Mortality was calculated based on dead and moribund larvae combined and compared with untreated controls. Compounds 2, 3, 4, 11, 15, 16, 22, 23, 28, 29, 32, 34, 35, 37, 41, 44, 53, 57, 58, 59, 62, 64 , 67, 72, 73, 74, 76, 79, 82, 87, 88, 92, 94, 95, 96, 101, 102, 103, 105, 106, 109, 11 1, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 123, 124, 125, 127, 128, 130, 135, 138, 139, 140, 141, 143, 147, 150, 151, 153, 154, 159, 160, 162, 164, 165, 1 68, 169, 171, 173, 174, 178, 179, 186, 187, 188, 189, 190, 191, 193, 195, 196, 197, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 221, 223, 224, 225, 226, 228, 231, 232, 233, 234, 235, 236, 237, 238, 242, 243, 244, 245, 246, 247, and 249 recorded mortality rates of over 70% at 300 PPM.

[0391] Although the invention has been described with reference to certain preferred embodiments, other embodiments will become apparent to those skilled in the art upon review of the specification. It will be apparent to those skilled in the art that many modifications, both to materials and methods, may be practiced without departing from the scope of the invention.

Claims

1. A compound of formula (I). [C40] Formula (I) Where: R is hydrogen, cyano, NO ２ , C １ ~C １０ -Alkyl, C １ ~C １０ -cyanoalkyl, C ２ ~C １０ -Alkenyl, C ２ ~C １０ -Alkynyl, C １ ~C １０ -Haloalkyl, C ２ ~C １０ -haloalkenyl, C ２ ~C １０ -haloalkynyl, -OR ５ , -C ２ ~C １０ -Alkyl-OR ５ , -C(=O)-R'', -C １ ~C １０ -Alkyl-C(=O)-R'', -C １ ~C ６ -Alkyl-NR'R'', -C(=O)-NR'R'', -C １ ~C １０ -Alkyl-C(=O)-NR'R'', -C ２ ~C ６ -alkenyl-C(=O)-N(R'R''), -C １ ~C １０ -Alkyl-S(O) ｎ R ６ , -S(O) ｎ R ６ , -S(O) ２ -phenyl, -S(O) ２ -C ３ ~C １０ -heterocyclyl, C ３ ~C １０ -Cycloalkyl, C ３ ~C １０ -Halocycloalkyl, C ３ ~C １０ -cyanocycloalkyl, (halo)C ３~C １０ -Cycloalkyl-C １ ~C １０ -Alkyl, C ３ ~C １０ -Cyanocycloalkyl-C １ ~C １０ -Alkyl, C ４ ~C １０ -cycloalkenyl, C ４ ~C １０ -Cycloalkynyl, bicyclic C ５ ~C １２ -Alkyl, bicyclic C ７ ~C １２ -Alkenyl, C ６ ~C １０ -Aryl, C ６ ~C １０ -Aryl-C １ ~C ６ -Alkyl, C ３ ~C １０ -heterocyclyl and C ３ ~C １０ -heterocyclyl-C １ ~C ６ -alkyl, where each group is one or more R ｂ and optionally substituted with R ｂ is halogen, CN, C １ ~C ６ -Alkyl, C １ ~C ６ -cyanoalkyl, C １ ~C ６ -haloalkyl, -OR ５ , -C(=O)-R'', -NR'R'', -S(O) ｎ R″ and C ３ ~C ６ -cycloalkyl; or R is phenyl, naphthyl and C ３ ~C １０ -heterocyclyl, each of which is optionally selected from the group consisting of one or more R ｘ (optionally substituted with R ｘ is halogen, hydrogen, cyano, NO ２ , C １~C １０ -Alkyl, C １ ~C １０ -cyanoalkyl, C ２ ~C １０ -Alkenyl, C ２ ~C １０ -Alkynyl, C １ ~C １０ -Haloalkyl, C ２ ~C １０ -haloalkenyl, C ２ ~C １０ -haloalkynyl, -OR ５ , -C １ ~C ６ -Alkyl-OR ５ , -C(=O)-R'', -NR'R'', -C １ ~C ６ -Alkyl-NR'R'', -NR'C(=O)-R'', -C(=O)-NR'R'', -C １ ~C １０ -Alkyl-C(=O)-NR'R'', -C １ ~C ６ -Alkyl-S(O) ｎ R ６ , -S(O) ｎ R ６ , C ３ ~C １０ -Cycloalkyl, C ３ ~C １０ -Halocycloalkyl, C ３ ~C １０ -cyanocycloalkyl, -SF ５ , -SCN, -S (=O) ０～１ (R ８ ) (=NR ７ ), -N=S(=O) ０～１ (R ９ ) (R １０ ), (Halo) C ３ ~C １０ -Cycloalkyl-C １ ~C ６ -Alkyl, C ３ ~C １０ -Cycloalkyl-C １ ~C ６ -Alkenyl, C ３ ~C １０ -Cycloalkyl-C １ ~C ６ -Alkynyl, C ３ ~C １０ -Cyanocycloalkyl-C １ ~C ６ -Alkyl, C ４ ~C １０ -Cycloalkenyl, bicyclic C ５ ~C １２ -Alkyl, bicyclic C ７ ~C １２ -Alkenyl, phenyl, benzyl, phenylethyl, C ３ ~C ６ -heterocyclyl and C ３ ~C ６ -heterocyclyl-C １ ~C ６ alkyl, wherein each group is selected from the group consisting of one or more R ｃ and optionally substituted with R ｃ is halogen, CN, C １ ~C ６ -Alkyl and C １ ~C ６ - alkoxy, A is CR ａ or N, R ａ is hydrogen, cyano, C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl, C １ ~C ４ -cycloalkyl and -(C=O)-R'', W １ and W ２ is independently selected from O or S; "n" is an integer ranging from 0 to 2, R １ and R ２ is hydrogen, halogen, cyano, C １ ~C ４ -Alkyl and C １ ~C ４ -haloalkyl; Het is selected from 5- to 6-membered heterocyclyl rings, optionally with one or more R ３ may be substituted with R ３ is hydrogen, halogen, cyano, C １ ~C ６ -Alkyl and C １ ~C ６ -haloalkyl; R ４ is hydrogen, halogen, cyano, C １ ~C ６ -Alkyl, C ２ ~C ６ -Alkenyl, C ２ ~C ６ -Alkynyl, C ２ ~C ６ -haloalkenyl, C ２ ~C ６ -haloalkynyl, C １ ~C ６ -Haloalkyl, C １ ~C ６ -Alkoxy and C １ ~C ６ -haloalkoxy, R ５ is 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 ２ ~C ６ -haloalkynyl, C ２ ~C ６ -haloalkynyl-C １ ~C ４ -Alkyl, C ３ ~C １０ -Cycloalkyl, C ３ ~C １０ -Halocycloalkyl and (halo)C ３ ~C １０ -Cycloalkyl-C １ ~C ６ - alkyl, R ６ is hydrogen, -NR'R'', C １ ~C ６ -Alkyl, C １ ~C ６ -Haloalkyl, C ３ ~C １０ -Cycloalkyl, C ３ ~C １０ -Halocycloalkyl and (halo)C ３ ~C １０ -Cycloalkyl-C １ ~C ６ - alkyl, R ７ is hydrogen, cyano, C １ ~C ６ -Alkyl, C ２ ~C ６ -Alkenyl, C ２ ~C ６ -Alkynyl, C ３ ~C ６ -cycloalkyl, (halo)C ３ ~C ６ -Cycloalkyl-C １ ~C ４ -Alkyl, C １ ~C ６ -Alkylcarbonyl and C １ ~C ４ -haloalkylcarbonyl, R ８ is C １ ~C ６ -Alkyl, C ２ ~C ６ -Alkenyl, C ２ ~C ６ -Alkynyl, C ３ ~C ６ -cycloalkyl, (halo)C ３ ~C ６ -Cycloalkyl-C １ ~C ４ -Alkyl, C １ ~C ６ -Haloalkyl and C ３ ~C ６-halocycloalkyl, R ９ and R １０ is C １ ~C ６ -Alkyl, C ２ ~C ６ -Alkenyl, C ２ ~C ６ -Alkynyl, C ３ ~C ６ -cycloalkyl, (halo)C ３ ~C ６ -Cycloalkyl-C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl and C ３ ~C ６ -halocycloalkyl; or R ９ and R １０ can form, together with the S atom to which they are attached, a 4-6 membered heterocycle, in which the C atoms of the heterocycle can optionally be substituted with C(=O) or C(=S), and said ring can optionally be substituted with one or more R ｃ may be substituted with R′ is hydrogen and C １ ~C ６ -alkyl, wherein said alkyl optionally comprises one or more halogens or C ３ ~C ６ - optionally substituted with cycloalkyl, R″ is hydrogen, C １ ~C ６ -Alkyl, C １ ~C ６ -Haloalkyl, C ３ ~C １０ -cycloalkyl, -N(R') ２ and -OR', where each group is optionally substituted with one or more halogens; or R″ represents phenyl, which may optionally be selected from halogen, cyano, C １ ~C ４ -Alkyl, C １ ~C ４ -Alkoxy or C １ ~C ４ -haloalkyl, Or, R′ and R″ together with the N atom to which they are attached can form a 4-6 membered heterocycle, in which the C atoms of the heterocycle can optionally be substituted with C(═O) or C(═S), and said ring can optionally be substituted with one or more R ｃ may be substituted with and / or a salt, stereoisomer, metal complex, polymorph, or N-oxide thereof.

2. R is phenyl, naphthyl and C ３ ~C １０ -heterocyclyl, each of which is optionally selected from the group consisting of one or more R ｘ may be substituted with R ｘ is halogen, hydrogen, cyano, NO ２ , C １ ~C １０ -Alkyl, C １ ~C １０ -cyanoalkyl, C ２ ~C １０ -Alkenyl, C ２ ~C １０ -Alkynyl, C １ ~C １０ -Haloalkyl, C ２ ~C １０ -haloalkenyl, C ２ ~C １０ -haloalkynyl, -OR ５ , -C １ ~C ６ -Alkyl-OR ５ , -C(=O)-R'', -NR'R'', -C １ ~C ６ -Alkyl-NR'R'', -NR'C(=O)-R'', -C(=O)-NR'R'', -C １ ~C １０ -Alkyl-C(=O)-NR'R'', -C １ ~C ６ -Alkyl-S(O)nR ６ , -S(O) ｎ R ６ , C ３ ~C １０ -Cycloalkyl, C ３ ~C １０ -Halocycloalkyl, C ３ ~C １０ -cyanocycloalkyl, -SF ５ , -SCN, -S (=O) ０～１ (R ８ ) (=NR ７ ), -N=S(=O) ０～１ (R ９ ) (R １０ ), (Halo) C ３ ~C １０ -Cycloalkyl-C １ ~C ６ -Alkyl, C ３ ~C １０ -Cycloalkyl-C １ ~C ６ -Alkenyl, C ３ ~C １０ -Cycloalkyl-C １ ~C ６ -Alkynyl, C ３ ~C １０ -Cyanocycloalkyl-C １ ~C ６ -Alkyl, C ４ ~C １０ -Cycloalkenyl, bicyclic C ５ ~C １２ -Alkyl, bicyclic C ７ ~C １２ -Alkenyl, phenyl, benzyl, phenylethyl, C ３ ~C ６ -heterocyclyl and C ３ ~C ６ -heterocyclyl-C １ ~C ６ -alkyl, where each group is one or more R ｃ and optionally substituted with R ｃ is halogen, CN, C １ ~C ６ -Alkyl and C １ ~C ６- alkoxy, A is CR ａ or N, R ａ is hydrogen, cyano, C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl, C １ ~C ４ -cycloalkyl and -(C=O)-R'', W １ and W ２ is independently selected from O or S; "n" is an integer ranging from 0 to 2, R １ and R ２ is hydrogen, halogen, cyano, C １ ~C ４ -Alkyl and C １ ~C ４ -haloalkyl; Het is selected from 5- to 6-membered heterocyclyl rings, optionally with one or more R ３ may be substituted with R ３ is hydrogen, halogen, cyano, C １ ~C ４ -Alkyl and C １ ~C ４ -haloalkyl; R ４ is hydrogen, halogen, cyano, C １ ~C ４ -Alkyl, C ２ ~C ４ -Alkenyl, C ２ ~C ４ -Alkynyl, C ２ ~C ４ -haloalkenyl, C ２ ~C ４ -haloalkynyl, C １ ~C ４ -Haloalkyl, C １ ~C ４ -Alkoxy and C １ ~C ４-haloalkoxy, R ５ is hydrogen, C １ ~C ４ -Alkyl, C ２ ~C ４ -Alkenyl, C ２ ~C ４ -Alkynyl, C ２ ~C ４ -haloalkenyl, C ２ ~C ４ -haloalkynyl, C ２ ~C ４ -haloalkynyl-C １ ~C ２ -Alkyl, C １ ~C ４ -Haloalkyl, C ３ ~C ６ -Cycloalkyl, C ３ ~C ６ -Halocycloalkyl and (halo)C ３ ~C ６ -Cycloalkyl-C １ ~C ４ - alkyl, R ６ is hydrogen, -NR'R'', C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl, C ３ ~C １０ -Cycloalkyl, C ３ ~C １０ -halocycloalkyl, and (halo)C ３ ~C １０ -Cycloalkyl-C １ ~C ６ - alkyl, R ７ is hydrogen, cyano, C １ ~C ４ -Alkyl, C ２ ~C ４ -Alkenyl, C ２ ~C ４ -Alkynyl, C ３ ~C ６ -cycloalkyl, (halo)C ３ ~C ６ -Cycloalkyl-C １ ~C ３ -Alkyl, C １ ~C ３ -Alkylcarbonyl and C １ ~C ３ -haloalkylcarbonyl, R ８ is C １ ~C ４ -Alkyl, C ２ ~C ４ -Alkenyl, C ２ ~C ４ -Alkynyl, C ３ ~C ６ -cycloalkyl, (halo)C ３ ~C ６ -Cycloalkyl-C １ ~C ３ -Alkyl, C １ ~C ４ -Haloalkyl and C ３ ~C ６ -halocycloalkyl; R ９ and R １０ is C １ ~C ４ -Alkyl, C ２ ~C ４ -Alkenyl, C ２ ~C ４ -Alkynyl, C ３ ~C ６ -cycloalkyl, (halo)C ３ ~C ６ -Cycloalkyl-C １ ~C ３ -Alkyl, C １ ~C ４ -Haloalkyl and C ３ ~C ６ halocycloalkyl; or R ９ and R １０ can form, together with the S atom to which they are attached, a 4-6 membered heterocycle, in which the C atoms of the heterocycle can optionally be substituted with C(=O) or C(=S), and said ring can optionally be substituted with one or more R ｃ may be substituted with R′ is hydrogen and C １ ~C ６ -alkyl, wherein said alkyl is optionally selected from the group consisting of one or more halogens or C ３ ~C ６ optionally substituted with cycloalkyl; R″ is hydrogen, C １ ~C ６ -Alkyl, C １ ~C ６ -Haloalkyl, C ３ ~C １０ -cycloalkyl, -N(R') ２ and -OR', where each group is optionally substituted with one or more halogens; or R″ represents phenyl, said phenyl being selected from halogen, cyano, C １ ~C ４ -Alkyl, C １ ~C ４ -Alkoxy or C １ ~C ４ -haloalkyl, said alkyl being optionally substituted with one or more halogens; or R′ and R″ together with the N atom to which they are attached may form a 4-6 membered heterocycle, the C atoms of which may be optionally substituted with C(═O) or C(═S), said ring being optionally formed by one or more R ｃ and optionally substituted with and / or a salt, stereoisomer, metal complex, polymorph, or N-oxide thereof; A compound of formula (I) according to claim 1.

3. Het is selected from one of Het-1 to Het-6; [C41] Where: # indicates the point of attachment to the rest of the molecule, m is 0, 1 or 2; R ３are independently hydrogen, halogen, cyano, C １ ~C ４ -Alkyl, and C １ ~C ４ - selected from the group consisting of haloalkyl, A compound of formula (I) according to claim 1 or claim 2.

4. Het is selected from Het-1-a to Het-6-b; [C42] In the formula, R ３ and m is as defined in claim 3; A compound of formula (I) according to claim 3.

5. W １ and W ２ A compound of formula (I) according to any one of claims 1 to 4, wherein is O.

6. A compound of formula (I) according to any one of claims 1 to 5, wherein A is nitrogen (N).

7. R is hydrogen, cyano, C １ ~C ６ -Alkyl, C １ ~C ６ -cyanoalkyl, C ２ ~C ６ -Alkenyl, C ２ ~C ６ -Alkynyl, C １ ~C ６ -haloalkyl, -C(=O)-R'', -OR ５ , -C １ ~C ６ -Alkyl-C(=O)-R'', -C １ ~C ６ -Alkyl-OR ５ , -S(O) ２ -phenyl, -S(O) ２ -C ３ ~C １０ -heterocyclyl, C ３ ~C ６ -Cycloalkyl, C ３ ~C ６-cyanocycloalkyl, (halo)C ３ ~C ６ -Cycloalkyl-C １ ~C ３ -alkyl, phenyl-C １ ~C ３ -Alkyl or C ３ ~C ６ -heterocyclyl-C １ ~C ３ -alkyl, where each group is optionally selected from one or more R ｂ or R is phenyl, naphthyl, oxetanyl, azetidinyl, thietanyl, thietanyl 1-oxide, thietanyl 1,1-dioxide, tetrahydro-2H-pyran-4-yl, thienyl, furanyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl. , 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,3,4-triazolyl, tetrazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiazolyl, benzoxazolyl, 2,2-difluorobenzo[d][1,3]dioxol-5-yl, quinolinyl, or isoquinolinyl, wherein each group is selected from one or more of R ｘ optionally substituted with A compound of formula (I) according to any one of claims 1 to 6.

8. R is phenyl, said phenyl being one or more R ｘ optionally substituted with A compound of formula (I) according to any one of claims 1 to 7.

9. R ｂ is halogen, CN, C １ ~C ６ -Alkyl, C １ ~C ６ -cyanoalkyl, C １ ~C ６ -haloalkyl, -OR ５ , -C(=O)-R'', -NR'R'', -S(O) ｎ R″ and C ３ ~C ６ -cycloalkyl; R ｘ is halogen, hydrogen, cyano, NO ２ , C １ ~C ６ -Alkyl, C １ ~C ６ -cyanoalkyl, C ２ ~C ６ -Alkenyl, C ２ ~C ６ -Alkynyl, C １ ~C ６ -Haloalkyl, C ２ ~C ６ -haloalkenyl, C ２ ~C ６ -haloalkynyl, C ３ ~C ６ -cycloalkyl, -OR ５ , -C(=O)-R'', -NR'R'', -C(=O)-NR'R'', -S(=O) ０～１ (R ８ ) (=NR ７ ), -N=S(=O) ０～１ (R ９ ) (R １０ ) or -S(O) ｎ R ６ wherein each group is independently selected from one or more R ｃ optionally substituted with A compound of formula (I) according to any one of claims 1 to 8.

10. R １ and R ２ A compound of formula (I) according to any one of claims 1 to 9, wherein is hydrogen.

11. R ３ are independently halogen or C １ ~C ４ A compound of formula (I) according to any one of claims 1 to 10, selected from haloalkyl.

12. A method for preparing a compound of formula (I) according to claim 1, comprising the steps selected from a) to e). a) Reacting a compound of formula (III) with a compound of formula (VI), optionally in the presence of a suitable catalyst, a suitable solvent and a suitable base, to obtain a compound of formula (II) or formula (IIB), which is further reacted with a carbonylating or thiocarbonylating reagent in the presence of a suitable solvent and a suitable base to obtain a compound of formula (I). [C43] Or, b) reacting a compound of formula (III) with a carbonylating or thiocarbonylating reagent in the presence of a suitable solvent and a suitable base to obtain a compound of formula (VIII), which is further reacted with a compound of formula (VI) optionally in the presence of a suitable catalyst, a suitable solvent and a suitable base to obtain a compound of formula (I). [C44] c) Further, the compound of formula (III) can be obtained by reacting the compound of formula (IV) with the compound of formula (V) in the presence of a suitable reagent, a suitable solvent and a suitable base to obtain the compound of formula (III). [C45] Or, d) The compound of formula (I) can be obtained by reacting a compound of formula (IIA) with a compound of formula (IIIA) or (IVB), optionally in the presence of a suitable catalyst, a suitable solvent and a suitable base. [C46] e) reacting the compound of formula (IIIB) with the compound of formula (IVA) in the presence of a suitable catalyst, a suitable solvent and a suitable base to obtain the compound of formula (VA), optionally in the presence of a base, by cyclocondensation reaction of the compound of formula (VA) with the compound of formula (VIA) to obtain the compound of formula (IIA). [C47] Where: X is a halogen; LG is a halogen, tosylate, nosylate, or mesylate; W １ , W ２ , R １ , R ２ , R ４ , R and Het are as defined in claim 1.

13. Compounds of formula (II) and (IIA). [C48] where LG is a halogen (preferably iodide, bromide or chloride), tosylate, nosylate, or mesylate. Het, R ４ , R １ , R ２ , R.W. １ and W ２ is as set forth in claim 1.

14. A compound of formula (IIB). [C49] In the formula, R is phenyl and C ３ ~C １０ -heterocyclyl, each group optionally containing one or more R ｘ LG is halogen (preferably iodide, bromide or chloride) or tosylate or nosylate, or mesylate; Het, R ４ , R １ , R ２ , R.W. １ and W ２ is as defined in claim 1.

15. A composition comprising a compound of formula (I) according to claim 1 or a salt, metal complex, stereoisomer, polymorph or N-oxide thereof, and at least one additional component selected from the group consisting of surfactants and adjuvants.

16. 16. The composition of claim 15, wherein the composition further comprises at least one biologically active compatible compound selected from a fungicide, an insecticide, a nematicide, an acaricide, a biopesticide, a herbicide, a plant growth regulator, an antibiotic, a fertilizer, or a nutrient.

17. 16. The composition according to claim 15, wherein said compound of formula (I) ranges from 0.1% to 99% by weight relative to the total weight of the composition.

18. A combination comprising a biologically effective amount of a compound of formula (I) as defined in claim 1 and at least one further biologically active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients.

19. 20. A method for combating insect and acarid pests comprising contacting the insect and acarid pests, their habitats, breeding grounds, food supply, plants, seeds, soil, areas, materials or environments in which the insect and acarid pests are growing or may grow, or materials, plants, seeds, soil, surfaces or spaces which are to be protected from pest attack or infestation, with a biologically effective amount of a compound of formula (I), salt, stereoisomer, polymorph, metal complex, N-oxide composition or combinations thereof as defined in claim 1 or 15 or 18.

20. Use of compounds of formula (I) or salts, metal complexes, N-oxides, stereoisomers, polymorphs, compositions or combinations thereof according to claims 1 or 15 or 18 for combating insect and acarine pests in agricultural and horticultural crops, in household and vector control and in animal parasitism.

21. 21. Use of a compound of formula (I) as claimed in claim 20, wherein the agricultural crops are cereals, maize, sorghum, bajra, rice, soybean, oilseeds and other legumes, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbits, olive plants, tobacco, coffee, tea, cocoa, sugar beet, sugarcane, cotton, potato, tomato, onion, pepper, ornamental plants, rapeseeds, fruiting vegetables, leafy vegetables, rapeseeds and other vegetables.

22. A seed comprising a compound of formula (I), or a salt, metal complex, N-oxide, stereoisomer, polymorph, composition or combination thereof according to claim 1 or 15 or 18, wherein the amount of the compound of formula (I) in said seed ranges from 0.0001% to 1% by weight.

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