1,2,3-triazolecarbonylsulfonylamide compounds and their uses

Abstract

1,2,3-triazolecarbonylsulfonylamide compounds and their uses The present invention provides novel 1,2,3-triazolecarbonylsulfonylamide compounds of formula (I). [62] JPEG2025503242000143.jpg2333 formula (I) Here, R 1 , R 2 and Z are as defined in the detailed description. The invention further relates to their preparation and their use for protecting crops from unwanted pests such as nematodes.

Description

[Technical field]

[0001] The present invention relates to novel nematicidal compounds of formula (I). More particularly, the present invention relates to novel 1,2,3-triazolecarbonylsulfonylamide compounds of formula (I) and methods for their preparation. The present invention further relates to compositions and combinations comprising such novel 1,2,3-triazolecarbonylsulfonylamide compounds and their use as crop protection agents for the control of pests such as plant parasitic nematodes. [Background technology]

[0002] The control of plant damage caused by phytopathogenic microorganisms and animal pests, especially plant parasitic nematodes, is crucial to achieve high crop efficiency.Nematodes cause substantial losses in agricultural food and industrial crops, and are therefore combated by compounds with nematocidal activity.Although many products are commercially available to control such damage, there is a continuing need for new compounds that are more effective, less toxic, less expensive, environmentally safe, and / or have a different mode of action.

[0003] The literature describes sulfonylamides and their suitability as pesticides, for example US Pat. No. 5,399,633 discloses condensed triazole acylsulfonamides as herbicides and / or plant growth regulators.

[0004] Further prior art documents, WO 02 / 06331, WO 02 / 06335, WO 02 / 06336, WO 02 / 06337, WO 02 / 06339 ... and WO 02 / 06339, describe condensed imidazole pyridine acylsulfonamide compounds which enable the control of harmful nematodes.

[0005] In addition to the above prior art documents, US Pat. Nos. 5,991,333 and 5,363,633 disclose disubstituted pyrazole / imidazole acylsulfonamides which can be used as nematicides. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] European Patent Application Publication No. 0244166 [Patent Document 2] International Publication No. 2010 / 129500 [Patent Document 3] International Publication No. 2012 / 054233 [Patent Document 4] International Publication No. 2015 / 169776 [Patent Document 5] International Publication No. 2017 / 157735 [Patent Document 6] International Publication No. 2018 / 083288 Summary of the Invention [Problem to be solved by the invention]

[0007] Under agricultural conditions, the effectiveness of the substituted sulfonylamides described in the prior art is not entirely satisfactory in various aspects, such as nematode-killing activity, application rate, treatment cost and toxicity.Therefore, there is always a high interest in finding new pesticide compounds for the control of pests such as nematodes, with better economic and environmental properties.The aim is to provide new compounds that are more active at lower application rates and environmentally safe, while maintaining efficacy, long-lasting activity and environmental and human health-related compatibility, at least in the same way or possibly in an improved way, compared to already known compounds. [Means for solving the problem]

[0008] The present invention describes compounds of formula (I) that exhibit the above-mentioned effects or advantages. The compounds of formula (I), i.e., novel 1,2,3-triazolecarbonylsulfonylamide compounds having substituted heterocycles, achieve this objective by exhibiting surprisingly significantly high activity levels against undesirable pests such as plant parasitic nematodes.

[0009] <Summary of the Invention> The present invention provides novel 1,2,3 triazole carbonylsulfonylamide compounds of formula (I). [ka] Formula (I) Here, R 1 , R 2 and Z is as defined in the detailed description.

[0010] In one embodiment, the present invention provides a method for preparing a compound of formula (I).

[0011] In another embodiment, the present invention provides a composition for controlling or preventing plant parasites, such as nematodes, comprising a biologically effective amount of a compound of formula (I) or a salt, stereoisomer, polymorph or N-oxide thereof, and at least one additional component selected from the group consisting of surfactants and adjuvants.

[0012] 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 biocide, a herbicide, a plant growth regulator, an antibiotic, a fertilizer, or a nutrient.

[0013] In yet another embodiment, the present invention provides the use of a compound of formula (I) or a salt, stereoisomer, polymorph or N-oxide thereof, composition or combination for the control of plant parasites such as nematodes.

[0014] In yet another embodiment, the present invention provides a method of combating plant parasites, such as nematodes, with a biologically effective amount of a compound of formula (I) or a salt, stereoisomer, polymorph or N-oxide thereof, as well as compositions or combinations thereof. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0015] <Definition> The terminology used in this disclosure is for purposes of illustration only and in no way limits the scope of the inventions disclosed in this disclosure.

[0016] 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 the limitations expressly stated. For example, a composition, mixture, formula, 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, formula, or process.

[0017] 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.

[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 "pesticide" in each case always also includes the term "crop protection agent".

[0021] 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.

[0022] The term "nematodes" refers to living organisms of the phylum Nematoda. The term "helminths" includes roundworms, filarial worms, phytophagous nematodes (Nematoda), trematoda, acanthocephalans, and cestoda.

[0023] In the context of this disclosure, "invertebrate pest control" means the stunting of invertebrate pests (including mortality, reduced feeding and / or disruption of mating), and related expressions are similarly defined.

[0024] The term "agronomic" refers to the production of field crops, such as for food 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).

[0025] The term "non-agronomic" refers to crops other than field crops, such as horticultural crops (e.g., greenhouse plants, nursery plants, ornamental plants that are 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.

[0026] 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 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 necrosis, 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.

[0027] The term "stereoisomer" refers to an isomer of the same arrangement of atoms in space that differs. Enantiomers and diastereomers are examples of stereoisomers. The term "enantiomer" refers to a pair of molecular species that are mirror images of each other and are not superimposable. The term "diastereomer" refers to a stereoisomer that is not a mirror image. The term "racemate" or "racemic mixture" refers to a composition consisting of equimolar amounts of two enantiomeric species that are not optically active.

[0028] The compounds of the present disclosure may exist in pure form or as a mixture of different possible isomeric forms, such as stereoisomers and structural isomers. 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.

[0029] Here, the meaning of various terms used in the specification will be explained.

[0030] In the above description, the term "alkyl" is used alone or in compound words such as "alkylthio" or "haloalkyl" or -N(alkyl) or alkylcarbonylalkyl or alkylsulfonylamino and refers to straight or branched C1-C 12It includes alkyl, preferably C1-C8 alkyl, more preferably C1-C6 alkyl. Non-limiting 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.

[0031] The term "alkenyl", used alone or in combination, refers to straight or branched C-C 12 -Alkenes, preferably C2-C 18-alkenes, more preferably C2-C6-alkenes. Non-limiting 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 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- Examples include 3-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.The term "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.

[0032] The term "alkynyl", used alone or in combination, refers to branched or straight chain C2-C 12 -Alkynes, preferably C2-C 18 -alkynes, more preferably C2-C6-alkynes. Non-limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl , 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl as well as different isomers. This definition also applies to alkynyl as part of a complex substituent, such as haloalkynyl, unless otherwise defined. The term "alkynyl" can also include moieties consisting of multiple triple bonds, such as 2,5-hexadiynyl.

[0033] The term "cyclic alkyl" or "cycloalkyl" refers to an alkyl closed to form a ring group. Non-limiting examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. This definition also applies to cycloalkyl as part of a compound substituent, such as cycloalkylalkyl, unless otherwise specifically defined.

[0034] The term "cycloalkylcycloalkyl" denotes a cycloalkyl substitution on another cycloalkyl ring, each cycloalkyl ring independently having from 3 to 7 carbon atom ring members. Examples of cycloalkylcycloalkyl include cyclopropylcyclopropyl (e.g., 1,1'-bicyclopropyl-1-yl, 1,1'-bicyclopropyl-2-yl), cyclohexylcyclopentyl (e.g., 4-cyclopentylcyclohexyl), and cyclohexylcyclohexyl (e.g., 1,1'-bicyclohexyl-1-yl), as well as the different cis- and trans-cycloalkylcycloalkyl isomers, such as (1R,2S)-1,1'-bicyclopropyl-2-yl and (1R,2R)-1,1'-bicyclopropyl-2-yl.

[0035] The term "alkoxy", used alone or in combination, means C1-C 12 Alkoxy, more preferably C1-C 18Alkoxy, most preferably C1 to C6 alkoxy. Examples of alkoxy include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpent ... pentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy as well as the different isomers. This definition also applies to alkoxy as part of a compound substituent, such as haloalkoxy, alkynylalkoxy, etc., unless otherwise specifically defined.

[0036] The term "cycloalkoxy" is 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 otherwise specifically defined elsewhere.

[0037] The term "alkylthio" refers to a branched or straight chain alkylthio moiety, such as, for example, 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- Examples include 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 different isomers.

[0038] 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.

[0039] Non-limiting examples of "alkylsulfonyl" include methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 1-methylpentylsulfonyl, 2- Examples include 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 and different isomers.

[0040] 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.

[0041] The term "halogen", either 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.

[0042] 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 otherwise defined elsewhere.

[0043] 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.

[0044] 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.

[0045] The term "haloalkylthio" or "haloalkylsulfanyl" 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.

[0046] Non-limiting examples of "haloalkylsulfinyl" include CF3S(O), CCl3S(O), CF3CH2S(O) and CF3CF2S(O). Non-limiting examples of "haloalkylsulfonyl" include CF3S(O), CCl3S(O), CF3CH2S(O) and CF3CF2S(O).

[0047] The term "ring" or "ring system" as a component of formula (I) is carbocyclyl or heterocyclyl.

[0048] The term "ring system" refers to one or more rings.

[0049] The term "bicyclic ring or ring system" denotes a ring system consisting of two or more common atoms.

[0050] The term "aromatic" indicates that the Huckel rule is met, and the term "non-aromatic" indicates that the Huckel rule is not met.

[0051] The terms "carbocycle" or "carbocyclic" or "carbocyclyl" include "aromatic carbocyclic ring systems" and "non-aromatic carbocyclic ring systems" or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds in which the rings may be aromatic or non-aromatic, where aromatic indicates that Huckel's rule is satisfied and non-aromatic indicates that Huckel's rule is not satisfied.

[0052] Non-limiting examples of non-aromatic carbocyclic ring systems are cyclopropyl, cyclobutyl, cyclopentyl, norbornyl, and the like.

[0053] Non-limiting examples of aromatic carbocyclic ring systems are phenyl, naphthyl, and the like.

[0054] The term "aryl" as used herein refers to any carbon-based aromatic group, including, but not limited to, phenyl, naphthalene, biphenyl, etc., preferably phenyl. Aryl groups may be substituted or unsubstituted. Furthermore, aryl groups may be a single ring structure, or may be fused ring structures or contain multiple ring structures linked via one or more bridging groups, such as carbon-carbon bonds.

[0055] The term "aralkyl" 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 "heterocycle" or "heterocyclic" includes "aromatic heterocycles" or "heteroaryl 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) 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.

[0058] 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 if the ring contains more than one oxygen atom, they are not directly adjacent. For example, oxiranyl, aziridinyl, oxetanyl, azetidinyl, thietanyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 5-isoxazolidinyl, 5-isothiazolidin ... Sothiazolidinyl, 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-oxadiazolidinyl 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,Examples of heterocyclyls include, but are not limited to, 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, and cycloserine. This definition also applies to heterocyclyls as part of a compound substituent, such as heterocyclylalkyl, unless otherwise defined elsewhere.

[0059] The term "heteroaryl" 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 triazole, 1-imidazolyl, 1,2,3 triazole and 1,3,4 triazole.

[0060] A 6-membered heteroaryl containing 1 to 4 nitrogen atoms includes, but is not limited to, a 6-membered heteroaryl group that can contain, in addition to carbon atoms, 1 to 3 and 1 to 4 nitrogen atoms as ring members, respectively, such as 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, and 1,2,4,5-tetrazin-3-yl.

[0061] This definition also applies to heteroaryl as part of a compound substituent, such as heteroarylalkyl, unless otherwise defined.

[0062] Those skilled in the art will understand that not all nitrogen-containing heterocycles form N-oxides because the nitrogen requires an available lone pair of electrons to be oxidized to the oxide. Those skilled in the art will recognize nitrogen-containing heterocycles that can form N-oxides. Those skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for preparing N-oxides of heterocycles and tertiary amines are very well known to those skilled in the art, including oxidation of heterocycles and tertiary amines with peracids such as peracetic acid and 3-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane. These methods for preparing N-oxides have been widely described and reviewed in the literature. See, for example, TL Gilchrist in Comprehensive Organic Synthesis, vol.7, pp748-750.

[0063] The term "amide" refers to A-R'C=ONR''-B, where R' and R'' represent substituents and A and B represent optional groups.

[0064] The term "thioamide" refers to A-R'C=SNR''-B, where R' and R'' represent substituents and A and B represent optional groups.

[0065] The term "leaving group (LG)" refers to any substituent that has sufficient nucleophilicity under the prevailing reaction conditions, or a group that can be nucleophilically displaced. Suitable leaving groups include, for example, halogens (chloro, iodo, bromo), triflates, nosylates, mesylates, tosylates, or SCh-Me.

[0066] "C i ~C j -Cycloalkyl-C i ~C j Examples of "-alkyl" include, but are not limited to, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, and cyclopentylethyl.

[0067] The total number of carbon atoms in the substituent is "C i ~C j」 The aryl groups are indicated by the prefixes i and j, where i and j are numbers from 1 to 21. For example, C1-C4 alkoxy means methoxy to butyloxy. 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.

[0068] 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. i~j When a range is indicated, the number of substituents may be selected from integers between i and j.

[0069] Substituents where the group may be hydrogen, e.g. R 1 or R 2 where the substituent is hydrogen, it is recognized that this is equivalent to the unsubstituted group.

[0070] Thus, the present invention provides a compound of formula (I): [ka] Formula (I) Where: R 1 teeth, [ka] (where: JPEG2025503242000005.jpg1415 represents the point of attachment to the triazole ring), or R 1 is selected from the group consisting of C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and C3-C8-cycloalkyl-C1-C6-alkyl, R 1 The C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and C3-C8-cycloalkyl-C1-C6-alkyl groups are not limited to halogen, CN, R 6a , OR 6a , S(O) n R 6a , N(R 6a )2 and COOR 6a and optionally substituted with one or more groups selected from the group consisting of R 1a is hydrogen, halogen, CN, OR 6a , C 1~ C6-Alkyl and C 1~ C-haloalkyl; R 1a Each group is a halogen, CN, R 6a , OR 6a , S(O) n R 6a , N(R 6a ) 2, COOR 6a and CONR 6a and optionally substituted with one or more groups selected from the group consisting of R 1b is halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, S(O) n R 6a and C-C-cycloalkyl-C-C-alkyl, where R 1b Each group is a halogen, R6a , OR 6a , S(O) n R 6a , N(R 6a ) 2, COOR 6a and CONR 6a and optionally substituted with one or more groups selected from the group consisting of R 2 is selected from the group consisting of hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C3-C6-cycloalkyl and phenyl, wherein the phenyl ring may be optionally substituted by one or more groups selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-alkoxy and C1-C4-haloalkyl, Z is Z-1 or Z-2; [ka] where * represents the point of attachment to the carbonyl group attached to the triazole ring; R 3 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C3-C6-cycloalkyl and C3-C8-cycloalkyl-C1-C6-alkyl, where R 3 Each group may be optionally substituted with halogen; A 1 , A 2 and A 3 represents C or N, where A 1 , A 2 and A 3 Two or less of these represent N, R 4 is hydrogen, halogen, CN, OR 6 , C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, and C2-C6-alkynyl; R 5 is hydrogen, halogen, CN, nitro, (C=O)-R 6 , O(C=O)-R 6 , OR 6 , N(R 6)2, CR 6 =NR 6 , COOR 6 , CON(R 6 )2, (C=S)-N(R 6 )2, S(O) n R 6 , OS(O) n R 6 , S(O) n N(R 6 )2, -S(=O) 0~1 R 7 (=NR 6 ), -N=S(=O) 0~1 (R 7 )2, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, phenyl, C3-C6-carbocyclyl and heterocyclic 3- to 6-membered rings, where R 5 Each group is a halogen, R 6a , OR 6a , S(O) n R 6a , N(R 6a ) 2, COOR 6a and CONR 6a and optionally substituted with one or more groups selected from the group consisting of R 6 is selected from the group consisting of hydrogen, hydroxy, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl and C3-C8-cycloalkyl-C1-C6-alkyl, R 6a is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl and C3-C8-cycloalkyl, R 7 and R 8 is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl and C3-C8-cycloalkyl and C3-C8-cycloalkyl-C1-C6-alkyl, n is an integer selected from 0 to 2; or a salt, stereoisomer, polymorph or N-oxide thereof, except that the following compounds are excluded from the definition of compounds of formula (I): 1H-1,2,3-triazole-4-carboxamide, 1-(2-cyclopropylethyl)-N-[(2,3-difluorophenyl)sulfonyl], 1H-1,2,3-triazole-4-carboxamide, N-[(4-bromo-2-chlorophenyl)sulfonyl]-1-(2-cyclopropylethyl), 1H-1,2,3-triazole-4-carboxamide, 1-(2-cyclopropylethyl)-N-[ [3-[(dimethylamino)carbonyl]phenyl]sulfonyl], 1H-1,2,3-triazole-4-carboxamide, 1-cyclohexyl-N-[[3-(4-methyl-2-thiazolyl)phenyl]sulfonyl] and 1H-1,2,3-triazole-4-carboxamide, 1-cyclopropyl-5-(difluoromethyl)-N-[[4-methyl-3-(trifluoromethyl)phenyl]sulfonyl].

[0071] In one embodiment, the invention provides a compound of formula (Ia): [ka] Formula (Ia) Here, R 1a , R 1b , R 2 , R 3 , R 4 , R 5 , A 1 , A 2 and A 3 is as stated above.

[0072] In another embodiment, the present invention provides a compound of formula (Ib): [ka] Formula (Ib) Here, R 1is selected from C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and C3-C8-cycloalkyl-C1-C6-alkyl, R 1 Each group may be optionally substituted with halogen or C1-C6-haloalkyl, preferably R 1 is C1-C6-haloalkyl, C3-C8-cycloalkyl and C3-C8-cycloalkyl-C1-C6-alkyl, optionally substituted with halogen or C1-C6-haloalkyl, R 2 , R 3 , R 4 , R 5 , A 1 , A 2 and A 3 is as defined above.

[0073] In a preferred embodiment, A 1 , A 2 and A 3 is one or more R 5 represents a carbon atom which may be optionally substituted with

[0074] In a further preferred embodiment, the present invention provides compounds of formula (Ia-1): [ka] Formula (Ia-1) Here, R 1a , R 1b , R 2 , R 3 , R 4 and R 5 is as described above.

[0075] In another preferred embodiment, the present invention provides compounds of formula (Ia-2): [ka] Formula (Ia-2) Here, R 1b , R 2 , R 3, R 4 and R 5 is as described above.

[0076] In another preferred embodiment, the present invention provides compounds of formula (Ia-3): [ka] Formula (Ia-3) Here, R 1b , R 2 , R 3 , R 4 and R 5 is as defined above.

[0077] In another preferred embodiment, the present invention provides compounds of formula (Ib-1): [ka] Formula (Ib-1) Here, R 1 , R 2 , R 3 , R 4 and R 5 is as defined above.

[0078] In one embodiment, the present invention provides a compound of formula (Ic): [ka] Formula (Ic) Here, R 1a , R 1b , R 2 , R 4 , R 5 , R 8 , A 1 , A 2 and A 3 is as defined above.

[0079] In another embodiment, the present invention provides a compound of formula (Id): [ka] Formula (Id) Here, R 1 , R 2 , R 4 , R 5、 R 8 , A 1 , A 2 and A 3 is as defined above.

[0080] In one preferred embodiment, A 1 , A 2 and A 3 is one or more R 5 represents a carbon atom which may be optionally substituted with

[0081] In another preferred embodiment, the present invention provides compounds of formula (Ic-1): [ka] Formula (Ic-1) Here, R 1a , R 1b , R 2 , R 4 , R 5 and R 8 is as defined above.

[0082] In yet another preferred embodiment, the present invention provides compounds of formula (Ic-2): [ka] Formula (Ic-2) Here, R 1b , R 2 , R 4 , R 5 and R 8 is as defined above.

[0083] In yet another preferred embodiment, the present invention provides compounds of formula (Ic-3): [ka] Formula (Ic-3) Here, R 1b, R 2 , R 4 , R 5 and R 8 is as stated above.

[0084] In yet another preferred embodiment, the present invention provides compounds of formula (Id-1): [ka] Formula (Id-1) Here, R 1 , R 2 , R 4 , R 5 and R 8 is as stated above.

[0085] The following list refers to the compounds of formula (I) of the present invention and is intended to illustrate the substituent R 1 , R 1a , R 1b , R 2 , Z, A 1 , A 2 , A 3 , R 3 , R 4 , R 5 , R 6 , R 6a , R 7 and R 8 For any one of these substituents, any of the definitions given below may be combined with any of the other substituent definitions given below or elsewhere in this specification.

[0086] In one embodiment of the present invention, R 1 is selected from the group consisting of C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl, where R 1 Each group is a halogen, CN, R 6a , OR 6a , S(O) n R 6a, N(R 6a )2 and COOR 6a and optionally substituted with one or more groups selected from the group consisting of:

[0087] In yet another embodiment of the present invention, R 1 is selected from the group consisting of C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl, where R 1 Each group is a halogen, CN and R 6a and optionally substituted with one or more groups selected from the group consisting of:

[0088] In yet another embodiment of the present invention, R 1 is selected from the group consisting of C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl, where R 1 Each group is a halogen, CN and R 6a and optionally substituted with one or more groups selected from the group consisting of:

[0089] In yet another embodiment of the present invention, R 1 is selected from the group consisting of C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl.

[0090] In one embodiment of the present invention, R 1 is as follows. [ka]

[0091] In a preferred embodiment of the present invention, R 1 is as follows. [ka]

[0092] In a preferred embodiment of the present invention, R 1 is as follows. [ka]

[0093] In another preferred embodiment of the present invention, R 1 is as follows. [ka]

[0094] In one embodiment of the present invention, R 1a is hydrogen, halogen, CN, OR 6a , C1-C4-alkyl and C1-C4-haloalkyl, where R 1a Each group is a halogen, CN, R 6a , OR 6a , S(O) n R 6a , N(R 6a ) 2、 COOR 6a and CONR 6a and optionally substituted with one or more groups selected from the group consisting of:

[0095] In another embodiment of the present invention, R 1a is hydrogen, halogen, CN, OR 6a , C1-C4-alkyl and C1-C4-haloalkyl, where R 1a Each group is a halogen, CN and R 6a and optionally substituted with one or more groups selected from the group consisting of:

[0096] In a preferred embodiment of the present invention, R 1ais selected from the group consisting of hydrogen, halogen, CN, methoxy, ethoxy, propoxy, butyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, fluoromethoxy, difluoromethoxy, difluoroethoxy, fluoroethoxy, trifluoromethoxy, trifluoroethoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2-trifluoroethyl, 2,2-difluoroethyl, 1,1-difluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-fluoroethyl, 2-chloroethyl, and pentafluoroethyl.

[0097] In one embodiment of the present invention, R 1b is halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, S(O) n R 6a and C3-C6-cycloalkyl-C1-C4-alkyl, where R 1b Each group is a halogen, R 6a , OR 6a , S(O) n R 6a , N(R 6a ) 2、 COOR 6a and CONR 6a and optionally substituted with one or more groups selected from the group consisting of:

[0098] In a preferred embodiment of the present invention, R 1b is selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl, where R1b Each group is a halogen, R 6a , OR 6a and S(O) n R 6a and optionally substituted with one or more groups selected from the group consisting of:

[0099] In a more preferred embodiment of the present invention, R 1b is selected from the group consisting of halogen, CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 1,1-difluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, methoxy, ethoxy, propoxy, butyloxy, fluoromethoxy, difluoromethoxy, difluoroethoxy, fluoroethoxy, trifluoromethoxy, trifluoroethoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, and cyclopentylmethyl.

[0100] In one embodiment of the present invention, R 6a is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl and C3-C6-cycloalkyl.

[0101] In another embodiment of the present invention, R 6a is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2 trifluoroethyl, 2,2-difluoroethyl, 1,1-difluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, cyclopropyl, cyclobutyl, and cyclopentyl.

[0102] In one embodiment of the present invention, OR 6a is selected from the group consisting of hydroxy, C1-C4-alkoxy, C1-C4-haloalkoxy and C3-C6-cycloalkyloxy.

[0103] In one preferred embodiment of the present invention, OR 6a is selected from the group consisting of hydroxy, methoxy, ethoxy, propoxy, butyloxy, allyloxy, propargyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclopropylmethoxy, cyclopropylethoxy, cyclobutylmethoxy, fluoromethoxy, difluoromethoxy, fluoroethoxy, trifluoromethoxy, and trifluoroethoxy.

[0104] In one embodiment of the present invention, -S(O) n R 6a -SR 6a , -S(O)R 6a and -S(O)2R 6a is selected from the group consisting of:

[0105] In another embodiment of the present invention, -SR 6a is selected from the group consisting of methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio and tert-butylthio, preferably methylthio or ethylthio.

[0106] Yet another embodiment of the present invention is -S(O)R 6a is selected from the group consisting of methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl and tert-butylsulfinyl, preferably methylsulfinyl or ethylsulfinyl.

[0107] Yet another embodiment of the present invention is -S(O)R 6ais selected from the group consisting of methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl and tert-butylsulfonyl, preferably methylsulfonyl or ethylsulfonyl.

[0108] In one embodiment of the present invention, -N(R 6a )2 is selected from the group consisting of amino, dimethylamino, diethylamino, diisopropylamino and dipropylamino.

[0109] In one embodiment of the present invention, -COOR 6a is selected from the group consisting of -COOH, -COOMe, -COOEt, -COOPr and -COOiPr.

[0110] In one embodiment of the present invention, -CONR 6a -CONH 2、 -CONHMe, -CON(Me) 2、 -CONHEt and -CON(Et)2.

[0111] In one embodiment of the present invention, R 2 is selected from the group consisting of hydrogen, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C3-C6-cycloalkyl and phenyl, wherein the phenyl ring may be optionally substituted with one or more groups selected from the group consisting of halogen, CN, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, difluoromethyl and trifluoromethyl.

[0112] In another embodiment of the present invention, R 2is selected from the group consisting of hydrogen, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, cyclopropyl and phenyl, wherein the phenyl ring may be optionally substituted with one or more groups selected from the group consisting of halogen, CN, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, difluoromethyl and trifluoromethyl.

[0113] In a preferred embodiment of the present invention, R 2 is selected from the group consisting of hydrogen, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C3-C6-cycloalkyl and phenyl.

[0114] In another preferred embodiment of the present invention, R 2 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, cyclopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl and trichloromethyl.

[0115] In a more preferred embodiment of the present invention, R 2 is selected from the group consisting of hydrogen, methyl, ethyl, cyclopropyl, and trifluoromethyl.

[0116] In the most preferred embodiment of the present invention, R 2 is methyl.

[0117] In one embodiment of the present invention, Z is Z-1 or Z-2, where A 1 , A 2 and A 3 represents C. [ka]

[0118] In another embodiment of the present invention, Z is Z-1 or Z-2, where A 1 , A 2 and A3 represents C, R 3 represents H, R 8 represents methyl. [ka]

[0119] In a preferred embodiment of the invention, Z is Z-1.

[0120] In one embodiment of the present invention, R 3 is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C3-C6-cycloalkyl and C3-C8-cycloalkyl-C1-C4-alkyl, where R 3 Each of the groups may be optionally substituted with halogen.

[0121] In another embodiment of the present invention, R 3 is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl and C3-C8-cycloalkyl-C1-C4-alkyl.

[0122] In a preferred embodiment of the present invention, R 3 is selected from the group consisting of hydrogen, methyl, ethyl, cyclopropylmethyl, and cyclopropylethyl.

[0123] In a more preferred embodiment of the present invention, R 3 is hydrogen.

[0124] In one embodiment of the present invention, R 4 is hydrogen, halogen, CN, OR 6 , C1-C6-alkyl and C1-C6-haloalkyl.

[0125] In another embodiment of the present invention, R 4 is hydrogen, halogen, CN, OR 6 , C1-C4-alkyl and C1-C4-haloalkyl.

[0126] In a preferred embodiment of the present invention, R 4 is selected from the group consisting of hydrogen, halogen, CN, methoxy, ethoxy, propoxy, butyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, fluoromethoxy, difluoromethoxy, difluoroethoxy, fluoroethoxy, trifluoromethoxy, trifluoroethoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2-trifluoroethyl, 2,2-difluoroethyl, 1,1-difluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-fluoroethyl, 2-chloroethyl, and pentafluoroethyl.

[0127] In a more preferred embodiment of the present invention, R 4 is selected from the group consisting of hydrogen, halogen, CN, methoxy, ethoxy, propoxy, difluoromethoxy, difluoroethoxy, trifluoromethoxy, trifluoroethoxy, methyl, ethyl, n-propyl, isopropyl, difluoromethyl, trifluoromethyl, and chloromethyl.

[0128] In one embodiment of the present invention, R 5 is hydrogen, halogen, CN, nitro, (C=O)-R 6 , OR 6 , N(R 6 )2, CR 6 =NR 6 , COOR 6 , CON(R 6 )2, S(O) n R 6 , S(O) n N(R 6 )2, -S(=O) 0~1 R 7 (=NR 6 ), -N=S(=O) 0~1 (R 7)2, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, phenyl, C3-C6-carbocyclyl and heterocyclic 3- to 6-membered rings, where R 5 Each group is a halogen, R 6a , OR 6a , S(O) n R 6a , N(R 6a ) 2, COOR 6a and CONR 6a and optionally substituted with one or more groups selected from the group consisting of:

[0129] In another embodiment of the present invention, R 5 is hydrogen, halogen, CN, nitro, (C=O)-R 6 , OR 6 , N(R 6 )2, S(O) n R 6 , S(O) n N(R 6 )2, -S(=O) 0~1 R 7 (=NR 6 ), -N=S(=O) 0~1 (R 7 )2, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkylC3-C6-cycloalkyl-C1-C4-alkyl, phenyl, C3-C6-carbocyclyl and heterocyclic 3- to 6-membered rings, where R 5 Each group is a halogen and R 6a and optionally substituted with one or more groups selected from the group consisting of:

[0130] In yet another embodiment of the present invention, R 5 is hydrogen, halogen, CN, nitro, OR 6, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl and C3-C6-carbocyclyl, where R 5 Each group is a halogen and R 6a and optionally substituted with one or more groups selected from the group consisting of:

[0131] In a preferred embodiment of the present invention, R 5 is hydrogen, halogen, CN, OR 6 , C1-C4-alkyl and C1-C4-haloalkyl.

[0132] In a more preferred embodiment of the present invention, R 5 is selected from the group consisting of hydrogen, halogen, CN, methoxy, ethoxy, propoxy, difluoromethoxy, difluoroethoxy, trifluoromethoxy, trifluoroethoxy, methyl, ethyl, n-propyl, isopropyl, difluoromethyl, trifluoromethyl, and chloromethyl.

[0133] In one embodiment of the present invention, R 6 is selected from the group consisting of hydrogen, hydroxy, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl.

[0134] In another embodiment of the present invention, R 6is selected from the group consisting of hydrogen, hydroxy, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 1,1-difluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, and cyclobutylethyl.

[0135] In a preferred embodiment of the present invention, R 6 is selected from the group consisting of hydrogen, hydroxy, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 1,1-difluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, cyclopropyl, cyclobutyl, and cyclopentyl.

[0136] In one embodiment of the present invention, OR 6 is selected from hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-cycloalkyloxy or -O-C1-C4-alkyl-C3-C6-cycloalkyl.

[0137] In another embodiment of the present invention, OR 6 is selected from hydroxy, C1-C6-alkoxy or C1-C6-haloalkoxy.

[0138] In one embodiment of the present invention, R 7is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl and C3-C6-cycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl.

[0139] In another embodiment of the present invention, R 7 is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 1,1-difluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, and cyclobutylethyl.

[0140] In a preferred embodiment of the present invention, R 7 is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, and cyclobutylethyl.

[0141] In a preferred embodiment of the present invention, R 8 is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl and C3-C6-cycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl.

[0142] In another embodiment of the present invention, R 8is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 1,1-difluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, and cyclobutylethyl.

[0143] In a preferred embodiment of the present invention, R 8 is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, and cyclobutylethyl.

[0144] In a preferred embodiment of the present invention, n is an integer selected from 0 to 2.

[0145] In one preferred embodiment, the present invention provides a compound of formula (Ia): [ka] Formula (Ia) Here, R 1a is hydrogen, halogen, CN, OR 6a , C1-C4-alkyl and C1-C4-haloalkyl, where R 1a Each group is a halogen, CN and R 6a and optionally substituted with one or more groups selected from the group consisting of R 1bis selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl, where R 1b Each group is a halogen, R 6a , OR 6a and S(O) n R 6a and optionally substituted with one or more groups selected from the group consisting of R 2 is selected from the group consisting of hydrogen, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, cyclopropyl and phenyl, wherein the phenyl ring may be optionally substituted by one or more groups selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-alkoxy and C1-C4-haloalkyl, R 3 is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl and C3-C8-cycloalkyl-C1-C4-alkyl, A 1 , A 2 and A 3 represents C or N, A 1 , A 2 and A 3 Not more than two of represent N, R 4 is hydrogen, halogen, CN, OR 6 , C1-C4-alkyl and C1-C4-haloalkyl; R 5 is hydrogen, halogen, CN, nitro, (C=O)-R 6 , OR 6 , N(R 6 )2, S(O) n R 6, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, phenyl, C3-C6-carbocyclyl and heterocyclic 3- to 6-membered rings, where R 5 Each group is a halogen, R 6a and optionally substituted with one or more groups selected from the group consisting of R 6a is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl and C3-C6-cycloalkyl, R 6 is selected from the group consisting of hydrogen, hydroxy, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl and C3-C6-cycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl, n is an integer selected from 0 to 2, or a salt, stereoisomer, polymorph or N-oxide thereof.

[0146] In another preferred embodiment, the present invention provides a compound of formula (Ia-1): [ka] Formula (Ia-1) Here, R 1a is hydrogen, halogen, CN, OR 6a , C1-C4-alkyl and C1-C4-haloalkyl, where R 1a Each group is a halogen, CN and R 6a and optionally substituted with one or more groups selected from the group consisting of R 1bis selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl, where R 1b Each group is a halogen, R 6a , OR 6a and S(O) n R 6a may be substituted with one or more groups selected from the group consisting of R 2 is selected from the group consisting of hydrogen, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, cyclopropyl and phenyl, wherein the phenyl ring may optionally be substituted by one or more groups selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-alkoxy and C1-C4-haloalkyl, R 3 is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl and C3-C8-cycloalkyl-C1-C4-alkyl, R 4 is hydrogen, halogen, CN, OR 6 , C1-C4-alkyl and C1-C4-haloalkyl; R 5 is hydrogen, halogen, CN, nitro, (C=O)-R 6 , OR 6 , N(R 6 )2, S(O) n R 6 , C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, phenyl, C3-C6-carbocyclyl and heterocyclic 3- to 6-membered rings, where R 5 Each group is a halogen, R 6a and optionally substituted with one or more groups selected from the group consisting of R6a is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl and C3-C6-cycloalkyl, R 6 is selected from the group consisting of hydrogen, hydroxy, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl and C3-C6-cycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl, n is an integer selected from 0 to 2, or a salt, stereoisomer, polymorph or N-oxide thereof.

[0147] In yet another preferred embodiment of the present invention, the present invention provides a compound of formula (Ia-2): [ka] Formula (Ia-2) Here, R 1b is selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl, where R 1b Each group is a halogen, R 6a , OR 6a and S(O) n R 6a and optionally substituted with one or more groups selected from the group consisting of R 2 is selected from the group consisting of hydrogen, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, cyclopropyl and phenyl, wherein the phenyl ring may be optionally substituted by one or more groups selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-alkoxy and C1-C4-haloalkyl, R 3is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl and C3-C8-cycloalkyl-C1-C4-alkyl, R 4 is hydrogen, halogen, CN, OR 6 , C1-C4-alkyl and C1-C4-haloalkyl; R 5 is hydrogen, halogen, CN, nitro, (C=O)-R 6 , OR 6 , N(R 6 )2, S(O) n R 6 , C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, phenyl, C3-C6-carbocyclyl and heterocyclic 3- to 6-membered rings, where R 5 Each group is a halogen, R 6a may be substituted with one or more groups selected from the group consisting of R 6a is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl and C3-C6-cycloalkyl, R 6 is selected from the group consisting of hydrogen, hydroxy, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl and C3-C6-cycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl, n is an integer selected from 0 to 2, or a salt, stereoisomer, polymorph or N-oxide thereof.

[0148] In yet another preferred embodiment of the present invention, the present invention provides a compound of formula (Ia-3): [ka] Formula (Ia-3) Here, R 1bis selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl, where R 1b Each group is a halogen, R 6a , OR 6a and S(O) n R 6a and optionally substituted with one or more groups selected from the group consisting of R 2 is selected from the group consisting of hydrogen, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, cyclopropyl and phenyl, wherein the phenyl ring is optionally substituted by one or more groups selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-alkoxy and C1-C4-haloalkyl, R 3 is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl and C3-C8-cycloalkyl-C1-C4-alkyl, R 4 is hydrogen, halogen, CN, OR 6 , C1-C4-alkyl and C1-C4-haloalkyl; R 5 is hydrogen, halogen, CN, nitro, (C=O)-R 6 , OR 6 , N(R 6 )2, S(O) n R 6 , C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, phenyl, C3-C6-carbocyclyl and heterocyclic 3- to 6-membered rings, where R 5 Each group is a halogen, R 6a may be substituted with one or more groups selected from the group consisting of R6a is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl and C3-C6-cycloalkyl, R 6 is selected from the group consisting of hydrogen, hydroxy, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl and C3-C6-cycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl, n is an integer selected from 0 to 2, or a salt, stereoisomer, polymorph or N-oxide thereof.

[0149] In one embodiment of the present invention, R 1a is hydrogen, halogen, CN, OR 6a , C1-C4-alkyl and C1-C4-haloalkyl, where R 1a Each group is a halogen, CN and R 6a and optionally substituted with one or more groups selected from the group consisting of:

[0150] R 1b is selected from the group consisting of halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl, where R 1b Each group is a halogen, R 6a , OR 6a and S(O) n R 6a and optionally substituted with one or more groups selected from the group consisting of:

[0151] R 4 is hydrogen, halogen, CN, OR 6 , C1-C4-alkyl and C1-C4-haloalkyl.

[0152] R 5is hydrogen, halogen, CN, nitro, OR 6 , C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl and C3-C6-carbocyclyl, where R 5 Each group is a halogen and R 6a and optionally substituted with one or more groups selected from the group consisting of:

[0153] R 6 is selected from the group consisting of hydrogen, hydroxy, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl and C3-C6-cycloalkyl-C1-C4-alkyl.

[0154] R 6a is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl and C3-C6-cycloalkyl.

[0155] In one preferred embodiment of the invention, the phenyl ring attached to the sulfonamide group is disubstituted.

[0156] In another preferred embodiment of the present invention, R 4 and R 5 is halogen, OR 6 , C1-C6-alkyl or C1-C6-haloalkyl, where OR 6 represents C1-C6-alkoxy or C1-C6-haloalkoxy.

[0157] In one embodiment of the present invention, the C3-C6-cycloalkyl group is preferably cyclopropyl.

[0158] The compounds of the present invention defined by Formula (I) listed in Tables 1-19 and / or Table (A) can be prepared as shown in the following Schemes, where, unless otherwise indicated, the definition of each variable is as defined above in the detailed description of the invention.

[0159] <General scheme of sulfonamides> [ka]

[0160] As shown in Scheme-1, the compound of formula Ia-a can be prepared from the compound of formula 3x-y by reacting with the compound of formula 2 in the presence of a suitable reagent such as a coupling reagent for 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, (1-[bis(dimethylamino)methylene]-1H-1,2,3 triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), in the presence of a suitable organic or inorganic base such as 4-dimethylaminopyridine, N,N-diisopropylethylamine, trimethylamine, sodium or potassium hydride, and in the presence of a suitable polar or non-polar solvent such as dichloromethane, tetrahydrofuran, N,N-dimethylformamide or tert-butyl alcohol or a mixture thereof.

[0161] [ka] As shown in Scheme-2, the compound of formula Ib-b can be prepared from the compound of formula 4x-y by reacting with the compound of formula 2 in the presence of a suitable coupling reagent such as 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide or (1-[bis(dimethylamino)methylene]-1H-1,2,3 triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), or by reacting the compound of formula 4x-y in the presence of a halogenating reagent such as phosphorus oxychloride, thionyl chloride, phosphorus pentachloride or oxalyl chloride in the presence of a suitable organic or inorganic base such as 4-dimethylaminopyridine, N,N-diisopropylethylamine, trimethylamine, sodium or potassium hydride, and in the presence of a suitable polar or non-polar solvent such as dichloromethane, tetrahydrofuran, N,N-dimethylformamide or tert-butyl alcohol or a mixture thereof.

[0162] The sulfonamide derivatives of formula 2 are commercially available or can be synthesised following analogous procedures as disclosed in WO 2007 / 023186 or WO 2007 / 144579.

[0163] [ka] As shown in Scheme-3, the compound of formula 5 can be converted to the compound of formula 6 by reaction with a suitable reagent such as trimethylsilyl azide, sodium azide in the presence of a suitable solvent such as methyl tert-butyl ether (MTBE) or acetonitrile, followed by a Sandmayer reaction using a suitable diazotizing agent (e.g., methyl nitrite, t-butyl nitrite, i-amyl nitrite, sodium nitrite, etc.) at 0°C to 25°C. In the next step, the compound of formula 6 can be converted to the compound of formula 8 by click reaction using a suitable reagent such as ethyl propiolate of formula 7, L-ascorbic acid and copper sulfate in the presence of a suitable solvent such as dimethyl sulfoxide. Furthermore, the compound of formula 8 can be converted to the triazole carboxylic acid of formula 3x using a suitable base such as lithium hydroxide or sodium hydroxide in the presence of a suitable solvent such as water, tetrahydrofuran, methanol or ethanol or a mixture thereof.

[0164] [ka] As shown in Scheme-4, the compound of formula 10 can be prepared by cyclocondensation of the compound of formula 6 with a 3-ketoester of formula 9, such as ethyl acetoacetate or ethyl trifluoroacetoacetate, in the presence of a suitable solvent, such as methyl tert-butyl ether (MTBE), dimethyl sulfoxide or water or a mixture thereof, in the presence of a suitable organic or inorganic base, such as piperidine, diethylamine or potassium carbonate. The resulting compound of formula 10 can then be converted to a triazole carboxylic acid of formula 3y using a suitable base, such as lithium hydroxide or sodium hydroxide, in the presence of a suitable solvent, such as water, tetrahydrofuran, methanol or ethanol or a mixture thereof.

[0165] [ka] As shown in Scheme-5, the compound of formula 12 can be prepared by reacting the compound of formula 11 with ethyl propiolate (formula 7) via (3+2) cycloaddition reaction in the presence of a suitable reagent such as L-ascorbic acid sodium salt and copper sulfate in the presence of a suitable solvent such as dimethylsulfoxide. The compound of formula 4x can then be prepared by hydrolysis of the compound of formula 12 using a suitable base such as lithium hydroxide or sodium hydroxide in the presence of a suitable solvent such as water, tetrahydrofuran, methanol or ethanol.

[0166] [ka] As shown in Scheme-6, compounds of formula 13 can also be prepared by reacting compounds of formula 11 with a 3-ketoester of formula 9, such as ethyl acetoacetate or ethyl trifluoroacetoacetate, in the presence of a suitable organic or inorganic base, such as piperidine, potassium carbonate or sodium carbonate, in the presence of a suitable solvent, such as dimethylsulfoxide or water. Compounds of formula 4y can then be prepared by hydrolyzing compounds of formula 13 using an ester hydrolysis reagent, such as lithium hydroxide, sodium hydroxide, in the presence of a suitable solvent, such as water, tetrahydrofuran, methanol or ethanol.

[0167] [ka] As shown in Scheme-7, compounds of formula Ia and Ib can be prepared by alkylation of compounds of formula Ia-a and Ib-b by reacting them with compounds of formula 14 in the presence of a suitable base such as sodium hydride, sodium tert-butoxide and potassium tert-butoxide in the presence of a suitable solvent such as N,N-dimethylformamide, dimethylsulfoxide or acetonitrile.

[0168] <General scheme of sulfoximines> [ka] As shown in Scheme-8, the compound of formula Ic can be prepared by coupling the compound of formula 3x-y with the compound of formula 15 in the presence of a suitable coupling reagent such as 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide or (1-[bis(dimethylamino)methylene]-1H-1,2,3 triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), in the presence of a suitable base such as 4-dimethylaminopyridine, N,N-diisopropylethylamine or trimethylamine, in the presence of a suitable solvent such as dichloromethane, N,N-dimethylformamide or tert-butyl alcohol or a mixture thereof.

[0169] [ka] As shown in Scheme 9, compounds of formula Id can be prepared by coupling compounds of formula 4x-y with compounds of formula 15 in the presence of a suitable coupling reagent such as 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide or (1-[bis(dimethylamino)methylene]-1H-1,2,3 triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), in the presence of a suitable base such as 4-dimethylaminopyridine, N,N-diisopropylethylamine, trimethylamine, and in the presence of a suitable solvent such as dichloromethane, N,N-dimethylformamide, or tert-butyl alcohol or a mixture thereof.

[0170] The sulfoximine derivatives of formula 15 can be synthesized according to similar procedures as disclosed in WO 2019 / 150219.

[0171] As shown above, the compounds of formula 3x-y include the compounds of formula 3x and 3y, and the compounds of formula 4x-y encompass the compounds of formula 4x and 4y.

[0172] Any of the compounds according to the invention can exist in the form of one or more optical isomers, geometric isomers or chiral isomers depending on the number of asymmetric centers in the compound.The invention therefore relates equally to all optical isomers and their racemic or scalemic mixtures (the term "scalemic" denotes a mixture of enantiomers in different ratios), as well as to mixtures of all possible stereoisomers, in all ratios.Diastereoisomers and / or optical isomers can be separated according to methods known per se to those skilled in the art.

[0173] Any compound according to the present invention can exist in one or more geometric isomeric forms depending on the number of double bonds in the compound.The present invention therefore relates equally to all geometric isomers and all possible mixtures in all ratios.Geometric isomers can be separated according to the general methods known per se to those skilled in the art.

[0174] Any of the compounds according to the invention may exist in one or more amorphous, isomorphic or polymorphic forms depending on its preparation, purification storage and various other influencing factors.The present invention therefore relates to all possible amorphous, isomorphic and polymorphic forms, in all proportions.Amorphous, isomorphic and polymorphic forms can be prepared and / or separated and / or purified according to general methods known per se to those skilled in the art.

[0175] A large number of suitable standard methods are known for carrying out chemical transformations, such as alkylation, halogenation, acylation, amidation, oximation, oxidation, reduction, etc. The choice of a suitable preparation method for a particular reaction step depends on the properties (e.g. reactivity) of the substituents of the intermediates involved. These reactions can be conveniently carried out mainly in a solvent. They can be conveniently carried out at various temperatures, usually under an inert atmosphere. The reactants can be reacted in the presence of a suitable base. Examples of suitable bases are, but are not limited to, alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal amides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal acetates, alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal dialkylamides or alkali metal or alkaline earth metal alkylsilylamides, alkylamines, alkylenediamines, free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocyclic compounds, ammonium hydroxide and carbocyclic amines. Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, N,N-diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

[0176] The reactants can be reacted with each other as such, i.e., without the addition of a solvent or diluent. The reactions according to Scheme-1 to Scheme-9 are advantageously carried out at a temperature range of about -20°C to about +50°C, preferably about 0°C to about 30°C.

[0177] Compounds of formula (I) can be converted into other compounds of formula (I) in a manner known per se by replacing one or more of the substituents of the starting compound of formula (I) with other substituents according to the invention in the usual manner. Depending on the reaction conditions and the choice of starting materials suitable in each case, it is possible, for example, to replace one substituent with other substituents according to the invention in only one reaction step, or to replace several substituents with other substituents according to the invention in the same reaction step. Salts of compounds of formula (I) can be prepared in a manner known per se. Thus, for example, acid addition salts of compounds of formula (I) are obtained by treatment with a suitable acid or a suitable ion exchange reagent, and salts with bases are obtained by treatment with a suitable base or a suitable ion exchange reagent. The salts are selected depending on the tolerance for use of the compounds, for example the agricultural or physiological tolerance. Salts of compounds of formula (I) can be converted into free compounds of formula (I), acid addition salts, and salts with bases, for example by treatment with a suitable acid or a suitable ion exchange reagent, in the usual manner, for example by treatment with a suitable basic compound or a suitable ion exchange reagent, into free compounds of formula (I), acid addition salts, and salts with bases, for example by treatment with a suitable acid or a suitable ion exchange reagent. The salts of the compounds of formula (I) can be converted in a manner known per se into other acid addition salts, for example by treating the salts of inorganic acids, such as the hydrochlorides, with suitable metal salts, such as the sodium, barium or silver salts, or by treating the acids with, for example, silver acetate, in which case the inorganic salts which form, for example, silver chloride, are insoluble and therefore precipitate from the reaction mixture.

[0178] In one embodiment, the present invention provides a method for synthesizing a compound of formula (I), comprising steps selected from a) to d).

[0179] The compound of formula (11) is reacted with a compound of formula (9) in the presence of a suitable base and a suitable solvent to give a compound of formula (13), which is further reacted with a hydrolysis reagent in the presence of a suitable solvent to give a compound of formula (4y). [ka]

[0180] The compound of formula (4y) is reacted with a compound of formula (2) in the presence of a suitable reagent, a suitable solvent and a suitable base to give a compound of formula (Ib-b). [ka]

[0181] The compound of formula (Ib) can be obtained by reacting a compound of formula (Ib-b) with a compound of formula (14) in the presence of a suitable solvent and a suitable base. [ka]

[0182] The compound of formula (Id) can be obtained by reacting a compound of formula (4y) with a compound of formula (15) in the presence of a suitable coupling reagent, a suitable solvent and a suitable base. [ka]

[0183] 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.

[0184] In yet another embodiment, the present invention provides compounds of formula (I) as set forth in Tables 1 to 19. These compounds can be prepared according to the methods described above for the compounds in Table A and the experimental procedures described below. 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-1). [ka] Formula (I-1)

[0185] Table Y shows the variables R of the compound of formula (I-1) 2 , R 3 , R 4 and R 5 The following is stated. [Table 1] TIFF2025503242000044.tif182116 TIFF2025503242000045.tif182116 TIFF2025503242000046.tif182116 TIFF2025503242000047.tif77120*CyPr=Cyclopropyl

[0186] Each of Tables 1 to 19 following Table Y above comprises 438 compounds of formula (I-1), where R 2 , R 3 , R 4 and R 5 has a given value for each row of table Y and R 1b are defined in the relevant Tables 1 to 19.

[0187] Thus, compound 1.1 corresponds to a compound of formula (I-1), where R 2 , R 3 , R 4 and R 5 is as defined in row 1 of table Y, and R 1b is as defined in Table 1. Compound 1.2 corresponds to the compound of formula (I-1), where R 2 , R 3 , R 4 and R 5 is as defined in row 2 of Table Y, Het is as defined in Table 1, etc.

[0188] Table 1: This table discloses 438 compounds of formula 1.1 to 1.438, where R 1b is 2-Cl, 4-OCF3. 2 , R 3 , R4 and R 5 are as defined in Table Y. For example, compound No. 1.1 has the following structure: [ka]

[0189] Table 2: This table discloses 438 compounds of formula 2.1 to 2.438, where R 1b is 2-Cl, 4-Cl, R 2 , R 3 , R 4 and R 5 is as defined in Table Y.

[0190] Table 3: This table discloses 438 compounds of formula 3.1 to 3.438, where R 1b is 2-CF3, 4-Cl, R 2 , R 3 , R 4 and R 5 is as defined in Table Y.

[0191] Table 4: This table discloses 438 compounds of formula 4.1 to 4.438, where R 1b is 2-Cl,4-CF3, R 2 , R 3 , R 4 and R 5 is as defined in Table Y.

[0192] Table 5: This table discloses 438 compounds of formula 5.1 to 5.438, where R 1b is 2-Cl,4-CN, and R 2 , R 3 , R 4 and R 5 is as defined in Table Y.

[0193] Table 6: This table discloses 438 compounds of formula 6.1 to 6.438, where R 1b is 2-Cl,4-F, R 2, R 3 , R 4 and R 5 is as defined in Table Y.

[0194] Table 7: This table discloses 438 compounds of formula 7.1 to 7.438, where R 1b is 2-Cl,4-OCH3, and R 2 , R 3 , R 4 and R 5 is as defined in Table Y.

[0195] Table 8: This table discloses 438 compounds of formula 8.1 to 8.438, where R 1b is 2-F,4-CN, R 2 , R 3 , R 4 and R 5 is as defined in Table Y.

[0196] Table 9: This table discloses 438 compounds of formula 9.1 to 9.438, where R 1b is 2-F,4-Cl, R 2 , R 3 , R 4 and R 5 is as defined in Table Y.

[0197] Table 10: This table discloses 438 compounds of formula 10.1 to 10.438, where R 1b is 2-F, 4-F, and R 2 , R 3 , R 4 and R 5 is as defined in Table Y.

[0198] Table 11: This table discloses 438 compounds of formula 11.1 to 11.438, where R 1b is 2-Cl,4-CH3, R 2 , R 3 , R 4 and R 5 is as defined in Table Y.

[0199] Table 12: This table discloses 438 compounds of formula 12.1 to 12.438, where R 1b is 2-F,4-CH3, R 2 , R 3 , R 4 and R 5 is as defined in Table Y.

[0200] Table 13: This table discloses 438 compounds of formula 13.1 to 13.438, where R 1b is 2-CF3,4-Cl, R 2 , R 3 , R 4 and R 5 is as defined in Table Y.

[0201] Table 14: This table discloses 438 compounds of formula 14.1 to 14.438, where R 1b is 2-Cl,4-OCF2, R 2 , R 3 , R 4 and R 5 is as defined in Table Y.

[0202] Table 15: This table discloses 438 compounds of formula 15.1 to 15.438, where R 1b is 3-Cl, 5-Cl, R 2 , R 3 , R 4 and R 5 is as defined in Table Y.

[0203] Table 16: This table discloses 438 compounds of formula 16.1 to 16.438, where R 1b is 3-Cl,5-OCF3, R 2 , R 3 , R 4 and R 5 is as defined in Table Y.

[0204] Table 17: This table discloses 438 compounds of formula 17.1 to 17.438, where R 1b is 3-CF3,5-Cl, R 2 , R 3 , R 4 and R 5 is as defined in Table Y.

[0205] Table 18: This table discloses 438 compounds of formula 18.1 to 18.438, where R 1b is 3-CF3,5-CF3, and R 2 , R 3 , R 4 and R 5 is as defined in Table Y.

[0206] Table 19: This table discloses 438 compounds of formula 19.1 to 19.438, where R 1b is 3-Cl, 5-Cl, R 2 , R 3 , R 4 and R 5 is as defined in Table Y.

[0207] In one embodiment, the present invention provides the use of a compound of formula (I) (including its stereoisomers, salts, polymorphs or N-oxides or compositions thereof or combinations thereof) for the control or prevention of agricultural and / or horticultural crops against insects, nematodes or mites.

[0208] In a preferred embodiment, the present invention provides the use of a compound of formula (I), including a salt, stereoisomer, polymorph or N-oxide thereof or a composition thereof or a combination thereof, for the control or prevention of agricultural and / or horticultural crops against nematodes.

[0209] Each crop is selected from cereals, corn, rice, soybeans and other legumes, fruits and fruit trees, nuts and nut trees, citrus and citrus trees, any horticultural plant, cucurbits, oil plants, tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton, potato, tomato, onion, pepper, other vegetables or ornamentals.

[0210] The compounds of the invention can be used to control or destroy pests, such as nematodes, which occur in plants, especially useful plants and ornamentals in agriculture and horticulture, or in organs of such plants, such as fruits, flowers, leaves, stems, tubers, seeds or roots. In some cases, even plant organs formed at a later time point remain protected from these pests.

[0211] The compounds of formula (I) according to the present invention are preventively and / or therapeutically useful active ingredients that can be used in the field of pest control against insecticide-resistant nematodes, even at low application rates. The compounds of formula (I) according to the present invention have a very favorable biocidal spectrum and are well tolerated by warm-blooded animal species, fish and plants. Therefore, the present invention can also utilize insecticidal compositions comprising the compounds of the present invention, such as formula (I). The compounds of formula (I) according to the present invention have been found to have a very favorable activity spectrum for the protection of animals and useful plants from attack and damage by nematodes for practical purposes. Therefore, the present invention can also utilize nematicidal compositions comprising the compounds of the present invention, such as formula (I). The compounds of formula (I) can have a strong fungicidal activity and can be used for the control of undesirable nematodes in the protection of agricultural or horticultural crops.

[0212] The compounds of formula (I) may be used as nematicides for crop protection, for example for the control of Tylenchida, Rhabditida, Dorylaimida and Tryplonchida.

[0213] The compounds of formula (I) can be used to control or prevent infection of agricultural or horticultural crops by phytopathogenic nematodes.

[0214] The compounds of formula (I) may be used to protect crops, where the agricultural crops are cereals, corn, rice, soybeans and other legumes, fruit and fruit trees, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbits, oil plants, tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton, potato, tomato, onion, pepper and other vegetables and ornamentals.

[0215] The compounds of formula (I) are particularly useful for controlling nematodes.Accordingly, in a further embodiment, the present invention also relates to a method for controlling damage to plants and parts thereof caused by plant parasitic nematodes (endoparasitic nematodes, hemiendoparasitic nematodes, ectoparasitic nematodes), in particular plant parasitic nematodes such as root-knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other Meloidogyne species. Examples include the cyst forming nematodes, Globodera rostochiensis and other Globodera spp., Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii and other Heterodera spp., the nematodes, Anguina spp., the stem and leaf nematodes, Aphelenchoides spp., the nematodes, Eelonolaimus longicaudatus and other Belonolaimus spp., the pinewood nematode, Bursaphelenchus xylophilus and other Bursaphelenchus spp., the ring nematodes, Criconema spp., Criconemella spp., Criconemoides spp., Mesocriconema spp., the stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species, awl nematodes, Dolichodorus species, spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species, sheathed and sheathed nematodes, Hemicycliophora species and Hemicriconemoides species, Hirshmanniella species, Lance nematodes, Hoploaimus species, root-knot nematodes, Nacobbus species, Needle nematodes, Longidorus elongatus and other Longidorus species, Pin nematodes, Pratylenchus species, Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species, Burning nematodes, Radopholus similis and other Pratylenchus species, Reniform nematodes, Rotylenchus robustus, Rotylenchus reniformis, other Rotylenchus species, Scutellonema species, Stubby root nematodes, Trichodorusprimitivus, 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, such as Subanguina spp., Hypsoperine spp., Macropostonia spp., Melinius spp., Punctodera spp., and Quinisulcius spp.

[0216] In particular, the nematode species Meloidogyne spp., Heterodera spp., Rotylenchus spp., Pratylenchus spp. and Radopholus spp. may be controlled with the compounds of the invention.

[0217] In one embodiment, the present invention provides a composition for controlling or preventing plant pathogenic nematodes comprising a compound of formula (I), a stereoisomer, salt, polymorph, or N-oxide thereof, and one or more inert carriers.

[0218] In another embodiment, the composition may further comprise one or more active compatible compounds selected from fungicides, insecticides, nematicides, acaricides, biocides, herbicides, plant growth regulators, antibiotics, nutrients, or fertilizers.

[0219] The concentration of the compound of formula (I) is in the range of 1 to 90% by weight, preferably in the range of 5 to 50% by weight, based on the total weight of the composition.

[0220] The present invention further relates to a composition for controlling unwanted nematodes, comprising at least one compound of formula (I) and one or more inert carriers, which further comprise agriculturally suitable auxiliaries, solvents, diluents, surfactants and / or extenders.

[0221] The present invention further relates to compositions for controlling unwanted nematodes comprising at least one compound of formula (I) and / or one or more active compatible compounds selected from fungicides, bactericides, acaricides, insecticides, nematicides, herbicides, biocides, plant growth regulators, antibiotics, fertilizers and / or mixtures thereof.

[0222] In general, the compound of the present invention is used in the form of a composition (e.g., formulation) containing a carrier.The compound of the present invention and its composition can be used in various forms, such as aerosol dispenser, capsule suspension, low-temperature mist concentrate, sprayable powder, emulsifiable concentrate, emulsified oil in water, emulsified water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure), gas-generating product, granule, high-temperature mist concentrate, large granule, fine granule, oil-dispersible powder, oil-miscible flowable concentrate, oil-miscible liquid, paste, plant rodlet, dry seed treatment powder, pesticide-coated seed, soluble concentrate, soluble powder, seed treatment solution, suspension concentrate (flowable concentrate), ultra-low volume (ulv) liquid, ultra-low volume (ulv) suspension, water-dispersible granule or tablet, water-dispersible powder for slurry treatment, water-soluble granule or tablet, water-soluble powder for seed treatment and wettable powder.

[0223] The formulation typically comprises a liquid or solid carrier and, optionally, one or more conventional formulation adjuvants, which may be solid or liquid adjuvants, such as non-epoxidized or epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil, soybean oil, etc.), antifoaming agents, such as silicone oils, preservatives, clays, inorganic compounds, viscosity modifiers, surfactants, binders and / or tackifiers. The composition may further comprise fertilizers, micronutrient donors, or other formulations that affect plant growth, as well as combinations comprising the compounds of the present invention and one or more other biologically active agents, such as fungicides, bactericides, nematicides, plant activators, acaricides and insecticides.

[0224] Thus, the present invention also makes available a composition comprising a compound of the invention and an agricultural carrier, and, optionally, one or more conventional formulation adjuvants.

[0225] The compositions are prepared in a manner known per se, for example by grinding, screening and / or compressing the solid compounds of the invention, and also by intimately mixing and / or grinding the compounds of the invention with an auxiliary (auxiliary agent), for example in the presence of at least one auxiliary agent. In the case of the solid compounds of the invention, grinding / grinding the compounds is to ensure a specific particle size. The methods for preparing these compositions and the use of the compounds of the invention for preparing these compositions are also the subject of the present invention.

[0226] Examples of compositions for agricultural use are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersions, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or capsules in polymeric substances, which contain at least a compound of the invention, the type of composition being chosen to suit the intended purpose and the prevailing circumstances.

[0227] Examples of suitable liquid carriers are non-hydrogenated or partially hydrogenated aromatic hydrocarbons, preferably xylene mixtures, alkylbenzenes such as alkylated naphthalenes or tetrahydronaphthalenes, aliphatic or cycloaliphatic hydrocarbons such as paraffins or cyclohexanes, alcohols such as ethanol, propanol or butanol, glycols and their ethers and esters such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, ketones such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents such as N-methylpyrrolid-2-one, dimethylsulfoxide or N,N-dimethylformamide, water, fractions C8-C of non-epoxidized or epoxidized vegetable oils. 12Examples of suitable carriers include rapeseed oil, castor oil, palm oil, soybean oil, silicone oil, etc. Solid carriers used for dusts, dispersible powders, etc. include, in principle, ground natural minerals such as calcite, talc, kaolin, montmorillonite, attapulgite, etc. To improve the physical properties, highly disperse silica or highly disperse absorbent polymers can also be added. Suitable particulate adsorbent carriers for granules are of the porous type, such as pumice, brick grit, sepiolite or bentonite, and suitable non-adsorbent carrier materials are calcite or sand. In addition, a large number of granular materials of inorganic or organic nature can be used, in particular dolomite or crushed plant residues. Suitable surface-active compounds are nonionic, cationic and / or anionic surfactants or surfactant mixtures having good emulsifying, dispersing and wetting properties, depending on the type of active ingredient to be formulated. The surfactants mentioned below should be considered merely as examples. A large number of further surfactants conventionally used in the field of formulation and suitable according to the invention are described in the relevant literature. Suitable nonionic surfactants are in particular polyglycol ether derivatives of aliphatic or (cyclo)aliphatic alcohols, saturated or unsaturated fatty acids or alkylphenols, which may contain from about 3 to about 30 glycol ether groups and from about 8 to about 20 carbon atoms in the (cyclo)aliphatic hydrocarbon radical, or from about 6 to about 18 carbon atoms in the alkyl portion of the alkylphenol. Also suitable are water-soluble polyethylene oxide adducts with polypropylene glycol, ethylenediaminopolypropylene glycol or alkylpolypropylene glycol, having from 1 to about 10 carbon atoms in the alkyl chain and from about 20 to about 250 ethylene glycol ether groups and from about 10 to about 100 propylene glycol ether groups. Usually, the above compounds contain from 1 to about 5 ethylene glycol units per propylene glycol unit. Examples which may be mentioned are nonylphenoxypolyethoxyethanol, castor oil polyglycol ether, polypropylene glycol / polyethylene oxide adduct, tributylphenoxypolyethoxyethanol, polyethylene glycol or octylphenoxypolyethoxyethanol.Also suitable are fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate. The cationic surfactants are in particular quaternary ammonium salts, generally having as substituents and as further substituents (non-halogenated or halogenated) at least one alkyl radical, lower alkyl radical, hydroxyalkyl radical or benzyl radical of about 8 to about 22 carbon atoms. The salts are preferably in the form of halides, methyl sulfates or ethyl sulfates. Examples are stearyltrimethylammonium chloride and benzylbis(2-chloroethyl)ethylammonium bromide.

[0228] Examples of suitable anionic surfactants are water-soluble soaps or water-soluble synthetic surface-active compounds. Examples of suitable soaps are alkali, alkaline earth or (unsubstituted or substituted) ammonium salts of fatty acids having from about 10 to about 22 carbon atoms, for example the sodium or potassium salts of oleic acid or stearic acid or natural fatty acid mixtures obtained, for example, from coconut oil or tall oil. Fatty acid methyl taurates must also be mentioned. However, synthetic surfactants are more frequently used, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates. As a rule, fatty sulfonates and fatty sulfates exist as alkali, alkaline earth or (substituted or unsubstituted) ammonium salts, which generally have an alkyl radical of from about 8 to about 22 carbon atoms, alkyl also being understood as including the alkyl part of the acyl radical. Examples that may be mentioned are the sodium or calcium salts of lignosulfonic acid, dodecyl sulfate or fatty alcohol sulfate mixtures prepared from natural fatty acids. This group also includes the sulfates and sulfonates of fatty alcohol / ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain two sulfonyl groups and a fatty acid radical of about 8 to about 22 carbon atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethanolammonium salts of decylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or naphthalenesulfonic acid / formaldehyde condensates. Furthermore, suitable phosphates, such as salts of the phosphoric acid ester of p-nonylphenol / (4-14)ethylene oxide adduct, or phospholipids are also possible.

[0229] As a rule, the composition comprises 0.1-99%, in particular 0.1-95%, of the compound according to the invention and 1-99.9%, in particular 5-99.9%, of at least one solid or liquid carrier, and as a rule it is possible for 0-25%, in particular 0.1-20%, of the composition to be surfactants (meaning in each case percentages by weight). Concentrated compositions tend to be preferred for commercial products, but the end consumer as a rule uses dilute compositions in which the concentration of active ingredient is substantially lower.

[0230] Examples of types of foliar formulations for premix compositions are as follows: [Table 2]

[0231] Meanwhile, examples of types of seed treatment formulations for premix compositions are as follows: [Table 3]

[0232] Examples of formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions, or mixtures thereof, and dusts.

[0233] The nature of the formulation as well as the method of application, e.g. foliar, dipping, spraying, dusting, scattering, coating or pouring, are selected according to the intended purpose and the prevailing circumstances.

[0234] Tank-mix compositions are generally prepared by diluting one or more premix compositions containing different pesticides and, optionally, further auxiliaries, with a solvent (e.g., water). Suitable carriers and adjuvants can be solid or liquid and are substances commonly used in formulation technology, such as natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.

[0235] Typically, tank-mix formulations for foliar or soil application contain 0.1-20%, particularly 0.1-15%, of the desired components and 99.9-80%, particularly 99.9-85%, of a solid or liquid auxiliary (including, for example, a solvent such as water), where the auxiliary may be a surfactant in an amount of 0-20%, particularly 0.1-15%, based on the tank-mix formulation. Typically, premix formulations for foliar application contain 0.1-99.9%, particularly 1-95%, of the desired components and 99.9-0.1%, particularly 99-5%, of a solid or liquid auxiliary (including, for example, a solvent such as water), where the auxiliary may be a surfactant in an amount of 0-50%, particularly 0.5-40%, based on the premix formulation.

[0236] Typically, tank-mix formulations for seed treatment contain 0.25-80%, in particular 1-75%, of the desired components and 99.75-20%, in particular 99-25%, of a solid or liquid auxiliary (including, for example, a solvent such as water), where the auxiliary may be a surfactant in an amount of 0-40%, in particular 0.5-30%, based on the tank-mix formulation.

[0237] Typically, premix formulations for seed treatment applications comprise 0.5-99.9%, especially 1-95%, of the desired component and 99.5-0.1%, especially 99-5%, of a solid or liquid adjuvant (e.g. comprising a solvent such as water), which may be a surfactant in an amount of 0-50%, especially 0.5-40%, based on the premix formulation, although commercial products are preferably formulated as concentrates (e.g. premix compositions) and end users normally use dilute formulations (e.g. tank mix compositions).

[0238] The preferred seed treatment premix formulation is an aqueous suspension concentrate. This formulation can be applied to seeds using conventional treatment techniques and machines, such as fluidized bed technology, roller mill method, rotary static seed treatment machine, and drum coater. Other methods, such as spouted bed, can also be useful. Seeds can be presized before coating. After coating, seeds are typically dried and then transferred to a sizer for size adjustment. Such procedures are known in the art, and the compounds of the present invention are particularly suitable for use in soil and seed treatment applications.

[0239] Generally, the premix composition of the invention contains 0.5 to 99.9%, in particular 1 to 95%, advantageously 1 to 50% by weight of a solid or liquid adjuvant (including, for example, a solvent such as water) in an amount of 0 to 50%, in particular 0.5 to 40%, by weight based on the weight of the premix formulation; the auxiliary agent (or adjuvant) may be a surfactant in an amount of 0 to 50%, in particular 0.5 to 40%, by weight based on the weight of the premix formulation.

[0240] In a preferred embodiment, the compound of formula (I) is in the form of a plant propagation material treatment (or protection) composition, independent of any other embodiment, wherein said plant propagation material protection composition may further comprise a colorant. The plant propagation material protection composition or mixture may also comprise at least one polymer from water-soluble and water-dispersible film-forming polymers that improve adhesion of the active ingredient to the treated plant propagation material, the polymer generally having an average molecular weight of at least 10,000 to about 100,000.

[0241] In one embodiment, the present invention provides a method for controlling or preventing the infestation of useful plants by phytopathogenic nematodes in agricultural and / or horticultural crops, characterized in that a compound of formula (I), a salt, stereoisomer, polymorph or N-oxide thereof, or a composition or combination thereof is applied to the plant, part thereof or a locus thereof.

[0242] In another embodiment, the present invention provides a method for controlling or preventing infestation of useful plants by phytopathogenic nematodes in agricultural and / or horticultural crops, comprising applying a compound of formula (I), a salt, stereoisomer, polymorph or N-oxide thereof, or a composition or combination thereof to the seeds of the plants.

[0243] In yet another embodiment, the present invention provides a method for controlling or preventing infection by phytopathogenic nematodes in agricultural and / or horticultural crops using a compound of formula (I), its salt, stereoisomer, polymorph or N-oxide or a composition or combination thereof, the method comprising the step of applying an effective dose of the compound or composition or combination in an amount ranging from 1 g to 5 kg per hectare of the agricultural and / or horticultural crop.

[0244] Examples of application methods of the compounds of the present invention and their compositions, i.e., methods for controlling pests in agriculture, are spraying, misting, dusting, brushing, dressing, spraying or injecting, which are selected to suit the intended purpose of the prevailing situation.

[0245] One of the application methods in agriculture is application to the leaves of plants (foliar application), and the frequency and rate of application can be selected according to the risk of infestation by the pest in question. Alternatively, the active ingredient can reach the plant through the root system, for example by applying the compound to the plant locus (systemic action), by applying a liquid composition of the compound into the soil (by immersion), or by applying a solid form of the compound in the form of granules to the soil (soil application). In the case of rice, such granules can be metered into flooded rice fields. Application of the compound of the present invention to the soil is the preferred application method.

[0246] Typical application rates per hectare are generally from 1 to 2000 g of active ingredient per hectare, especially from 10 to 1000 g / ha, preferably from 10 to 600 g / ha, for example from 50 to 300 g / ha.

[0247] In one embodiment, the present invention provides seeds comprising a compound of formula (I) or a salt, stereoisomer, polymorph or N-oxide thereof, or compositions or combinations thereof, wherein the amount of compound of formula (I) ranges from 0.1 g to 10 kg per 100 kg of seeds.

[0248] The compounds of the invention and their compositions are also suitable for the protection of plant propagation material, for example seeds such as fruits, tubers or grains, or seedling plants against the above-mentioned types of pests. The propagation material can be treated with the compounds before planting, for example seeds can be treated before sowing. Alternatively, the compounds can be applied to the seed kernels (coating) by immersing the seed kernels in a liquid composition or by applying a layer of a solid composition. The compositions can also be applied when the propagation material is planted at the application site, for example in a seed furrow during drilling. These methods of treatment of plant propagation material and the plant propagation material thus treated are further subjects of the invention. Typical treatment rates depend on the plants and pests to be controlled and are generally between 1 and 200 g per 100 kg of seeds, preferably between 5 and 150 g per 100 kg of seeds, for example between 10 and 100 g per 100 kg of seeds. Application of the compounds of the invention to the seeds is a preferred application method.

[0249] The term "seed" includes all types of seeds and plant propagation materials, including, but not limited to, true seeds, seed pieces, suckers, corn, bulbs, fruits, tubers, grains, rhizomes, cuttings, cut shoots, and the like, and in a preferred embodiment refers to true seeds.

[0250] The present invention also includes seeds coated or treated with or containing a compound of formula (I). The term "coated or treated and / or containing" generally means that the active ingredient is mostly present on the surface of the seed upon application, although depending on the application method, most or less of the ingredient may penetrate into the seed material. When the seed product is (re)planted, it is capable of absorbing the active ingredient. In one embodiment, the present invention provides a plant propagation material having attached thereto a composition comprising a compound of formula (I) or a plant propagation material treated with a compound of formula (I).

[0251] Seed treatment includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting. The seed treatment application of the compound of formula (I), which is the preferred application method, can be carried out by any known method, such as spraying or seed dusting before sowing or during sowing / planting of the seed.

[0252] Suitable target plants are in particular cereals such as wheat, barley, rye, oats, rice, corn or sorghum, beets such as sugar or fodder beets, fruits such as bananas, fruits of the ginger family, stone fruits or soft fruits such as apples, pears, plums, peaches, almonds, cherries or berries such as strawberries, raspberries or blackberries, legumes such as beans, lentils, peas or soybeans, oil plants such as rapeseed, mustard, poppy, olive, sunflower, coconut, castor, cocoa or ground nuts, and wheat plants such as pumpkin, cucumber, melon. Plants include cereals, fiber plants such as cotton, flax, hemp, jute, citrus fruits such as orange, lemon, grapefruit, tangerine, vegetables such as spinach, lettuce, asparagus, cabbage, carrot, onion, tomato, potato, pepper, Lauraceae such as avocado, cinnamon, camphor, tobacco, nuts, coffee, eggplant, sugarcane, tea, pepper, grape, hops, Plantago japonica, latex plants, and ornamental plants (such as flowers and grasses). In one embodiment, the plant is selected from cereals, corn, soybeans, rice, sugarcane, vegetables, and oil plants.

[0253] The term "plant" is understood to include plants that have been transformed by the use of recombinant DNA techniques to synthesize one or more selectively acting toxins, such as those known from toxin-producing bacteria, particularly those of the genus Bacillus, as well as plants that have been selected or hybridized to maintain and / or achieve desired traits, such as insect and / or nematode resistance. Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae. or 8-endotoxins, such as insecticidal proteins from Bacillus thuringiensis, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or proliferative insecticidal proteins (Vip), such as Vip1, Vip2, Vip3 or Vip3A, or insecticidal proteins of bacteria colonizing nematodes, such as Photorhabdus spp. or Xenorhabdus spp. (Photorhabdus luminescens, Xenorhabdus nematophilus, etc.), animal produced toxins such as scorpion venom, spider venom, wasp venom and other insect specific neurotoxins, fungal produced toxins such as actinomycete toxins, plant lectins such as pea, barley and snowdrop lectins, agglutinins, proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors, ribosome inactivating proteins (RIPs) such as ricin, maize-RIP, abrin, rufin, saporin, bryodin, ion channel blockers such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyltransferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.In the context of the present invention, 8-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), such as Vip1, Vip2, Vip3 or Vip3A, should be understood to expressly include hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by new combinations of different domains of these proteins (see, for example, WO 2002 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, preferably non-naturally occurring protease recognition sequences are inserted into the toxin. For example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see, for example, WO 2003 / 018810). Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP-A-0374753, WO-A-1993 / 07278, WO-A-1995 / 34656, EP-A-0427529, EP-A-451878 and WO-A-2003 / 052073. Methods for the preparation of such transgenic plants are generally known to those skilled in the art and are described, for example, in the above-mentioned publications. Cryl-type deoxyribonucleic acids and methods for their preparation are known, for example, from WO-A-1995 / 34656, EP-A-0367474, EP-A-0401979 and WO-A-1990 / 13651. The toxins contained in the transgenic plants confer resistance to the plant against harmful insects. Such insects can be found in any taxonomic group of insects, but are particularly common among beetles (Coleoptera), dipteran insects (Diptera), and butterflies (Lepidoptera). Transgenic plants that contain one or more genes encoding insecticide resistance and expressing one or more toxins are known, and some of them are commercially available.Examples of such plants are: YieldGard® (a corn variety expressing the Cry1Ab toxin), YieldGard Rootworm® (a corn variety expressing the Cry3Bb1 toxin), YieldGard Plus® (a corn variety expressing the Cry1Ab and Cry3Bb1 toxins), Starlink® (a corn variety expressing the Cry9C toxin), HerculexI® (a corn variety expressing the Cry1Fa2 toxin and phosphinothricin N-acetyltransferase (PAT) and conferring resistance to the herbicide glufosinate ammonium), NuCOTN 33B® (a cotton variety expressing the Cry1Ac toxin), Bollgard I® (a cotton variety expressing the Cry1Ac toxin), Bollgard II® (a cotton variety expressing Cry1Ac and Cry2Ab toxins), VipCot® (a cotton variety expressing Vip3A and Cry1Ab toxins), Newleaf® (a potato variety expressing Cry3A toxin), NatureGard®, 25 Aggrisure® GT Advantage (GA21 glyphosate tolerance trait), Aggrisure® CB Advantage (Bt11 corn borer (CB) trait), and Protecta®. Further examples of such transgenic plants are: i) Bt11 maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-3 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10, a genetically modified Zea mays rendered resistant to attack by European American dough (Ostrinia nubi / alis and Sesamia nonagrioides) by the transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also transgenic expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium. ii) Bt176 maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-3 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10, a genetically modified Zea mays rendered resistant to attack by European black dung (Ostrinia nubi / alis and Sesamia nonagrioides) by the transgenic expression of the Cry1Ab toxin. Bt176 maize also transgenic expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium. iii) MIR604 maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-3 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10, a maize made insect-resistant by transgenic expression of a modified Cry3A toxin, this toxin being Cry3A055 modified by the insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 2003 / 018810. iv) MON863 maize from Monsanto Europe SA, 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9; MON863 expresses the Cry3Bb1 toxin and is resistant to certain beetles. v) Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, IPC 531 Cotton, registration number C / ES / 96 / 02. vi) Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, 1507 Maize with registration number C / NL / 00 / 10, a genetically modified maize for the expression of the protein Cry1F to achieve resistance to certain lepidopteran insects and for the expression of the PAT protein to achieve resistance to the herbicide glufosinate ammonium. vii) NK603xMON810 maize, Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03, consisting of a conventionally bred hybrid maize variety crossing the transgenic varieties NK603 and MON810. NK603xMON810 maize transgenically expresses the protein CP4EPSPS obtained from Agrobacterium sp., the CP4 strain conferring resistance to the herbicide Roundup® (containing glyphosate), and the Cry1Ab toxin also obtained from Bacillus thuringiensis subsp. kurstaki, which confers resistance to certain lepidoptera, including the European corn borer.

[0254] In one embodiment, the invention provides a combination comprising a compound of formula (I) (including salts, stereoisomers, polymorphs or N-oxides thereof) and one or more active compatible compounds selected from a fungicide, an insecticide, an insecticide, a nematicide, acaricide, a biocide, a herbicide, a plant growth regulator, an antibiotic, a nutrient, or a fertilizer.

[0255] The compounds of the present invention, when used alone, are effective in controlling nematodes on growing and harvested agricultural plants. They can also be used in combination with other biologically active agents applied in agriculture, such as one or more chemical nematodes, biological nematodes, insecticides, acaricides, fungicides, biological preparations, bactericides, plant activators, molluscicides, and pheromones (chemical or biological). When the compounds of the present invention or compositions thereof are mixed with other insecticides in the form of their use as insecticides, a broader insecticidal spectrum of action can often be obtained. For example, the compounds of formula (I) of the present invention can be effectively used in combination with pyrethroids, neonicotinoids, macrolides, diamides, phosphates, carbamates, cyclodienes, formamidines, phenolic tin compounds, chlorinated hydrocarbons, benzoylphenylureas, pyrroles, and the like.

[0256] The activity of the composition of the present invention can be considerably expanded and adapted to the general situation, for example by adding one or more insecticides, acaricides, nematicides and / or fungicides.The combination of the compound of formula (I) with other insecticides, acaricides, nematicides and / or fungicides, including biological agents, can have further surprising advantages.For example, better resistance by plants, reduced phytotoxicity, pests can be controlled at their different developmental stages, or better behavior can be controlled during their production, for example during grinding or mixing, during their storage or during their use.

[0257] Known and reported active compounds such as fungicides, insecticides, nematicides, acaricides, biocides, herbicides, safety agents, plant growth regulators, antibiotics, fertilizers and nutrients can be combined with at least one compound of formula (I) of the present invention. For example, the fungicides, insecticides, nematicides, acaricides, biocides, herbicides, safety agents, plant growth regulators, antibiotics, fertilizers and nutrients disclosed and reported in WO 2017 / 076739 (A-O) can be combined with the compound of formula (I) of the present invention. The present invention also relates to such combinations comprising the compound of the present invention and the active compatible compounds reported in WO 2017 / 076739.

[0258] The abovementioned active substances, their preparation and their activity against, for example, harmful fungi / insects / nematodes are known (see http: / / www.alanwood.net / pesticides / ). Most of these substances are commercially available.

[0259] The weight ratio of any two components in each combination is selected to provide the desired effect, e.g., enhanced activity. Generally, the weight ratio will vary depending on the particular components and the number of components present in the combination.

[0260] According to further embodiments of the two-component combinations and compositions, the weight ratio of component 1) to component 2) is usually in the range of 1000:1 to 1:1, often in the range of 100:1 to 1:1, usually in the range of 50:1 to 1:1.

[0261] According to further embodiments of the two-component combinations and compositions, the weight ratio of component 1) to component 2) is usually in the range of 1:1 to 1:1000, often in the range of 1:1 to 1:100, usually in the range of 1:1 to 1:50.

[0262] Mixing ratios are understood to include, on the one hand, mass ratios and, on the other hand, molar ratios.

[0263] The combinations of the present invention (ie, those comprising a compound of the present invention and one or more other biologically active agents) may be applied simultaneously or sequentially.

[0264] In that case, the components of the combination are applied sequentially within a reasonable period of each other, for example within hours or days, to achieve a biological performance. The order in which the components of the combination are applied is not essential to practicing the invention.

[0265] When the components of a combination are applied simultaneously in the present invention, they may be applied as a composition comprising the combination, in which case (A) the compound of formula (I) and one or more other components of the combination may be obtained from separate formulation sources and mixed together (known as a tank mix, ready-to-use spray broth, or slurry), or (B) the compound of formula (I) and one or more other components may be obtained as a single formulation mixed source (known as a premix, ready mix, concentrate, formulation).

[0266] In one embodiment, and independently of other embodiments, the compound according to the present invention is applied as a combination.Therefore, the present invention also provides a composition comprising the compound according to the present invention as described herein and one or more other biologically active agents, and optionally one or more conventional formulation auxiliary agents, which may be in the form of tank mix or premix composition.

[0267] The compounds of formula (I) are particularly useful for controlling and preventing the infestation and infection of helminths and nematodes endo- and ectoparasites in warm-blooded animals, such as cattle, sheep, pigs, camels, deer, horses, poultry, fish, rabbits, goats, minks, foxes, chinchillas, dogs, and cats, as well as humans.In the context of controlling and preventing the infestation and infection in warm-blooded animals, the compounds of the present invention are particularly useful for controlling helminths and nematodes.Examples of helminths include members of the class Trematoda, commonly known as flukes or flatworms, in particular members of the genera Fasciola, Fasciola, Paramphistom, Dicrocoelium, Eurytrema, Ophisthorchis, Fasciola, Echinostoma, and Paragonimus. Nematodes that may be controlled by the compounds of formula (I) include the genera Haemonchus, Ostertagia, Cooperia, Oesphagastomu, Nematodirus, Dictyocaulus, Trichuris, Dirofilaria, Ancyclostoma, Ascaria, and the like. For oral administration to warm-blooded animals, the compounds of the present invention may 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 present invention may be administered to animals in their drinking water. For oral administration, the dosage form selected should provide the animal with about 0.01 mg / kg to 10 g / kg of animal body weight / day of the compound of the present invention. Alternatively, the compounds of the present invention may be administered to animals parenterally, for example, by intraluminal, intramuscular, intravenous, or subcutaneous injection. The compounds of the present invention may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds of the present invention may be formulated into an implant for subcutaneous administration. Additionally, the compounds of the invention can be administered transdermally to animals. For parenteral administration, the dosage form selected should provide the animal with about 0.01 mg / kg to 100 mg / kg of the compound of the invention per day.

[0268] The compounds of the present invention can also be applied topically to animals in the form of dips, dusts, powders, collars, medallions, sprays and pour-on formulations. For topical application, dips and sprays usually contain about 0.5 ppm to 5,000 ppm, preferably about 1 ppm 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.

[0269] In one embodiment, independent of other embodiments, the compound of formula (I) is an anti-helminthic compound.

[0270] In one embodiment, independent of other embodiments, the compound of formula (I) is an insecticidal compound, preferably a nematicidal compound.

[0271] The compounds of the present invention not only effectively control nematode pests, but also exhibit plant growth enhancing effects such as enhanced crop vigor, enhanced root growth, enhanced resistance to drought, high salt, high temperature, cold, frost or light exposure, improved flowering, efficient water and nutrient utilization (e.g. improved nitrogen assimilation), improved quality of plant products, increased number of productive tillers with high productivity, enhanced resistance to pests, and the like, resulting in increased yields. EXAMPLES

[0272] [Chemical Examples] The following examples describe, without limitation, methods and processes for making the compounds of this invention and include the best modes contemplated by the inventors for carrying out their invention.

[0273] <Example 1> 1-(3,5-dichlorophenyl)-N-((2,5-dichlorophenyl)sulfonyl)-1H-1,2,3-triazole-4-carboxamide [ka] Step-1: Preparation of 1-azido-3,5-dichlorobenzene Azidotrimethylsilane (9.87mL, 74.1mmol) and tert-butyl nitrite (8.81mL, 74.1mmol) were added successively to a stirred solution of 3,5-dichloroaniline (8g, 49.4mmol) in acetonitrile (80mL) at 0°C, and the resulting mixture was stirred at the same temperature for 3 hours. After completion of the reaction, the mixture was concentrated under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography to obtain 1-azido-3,5-dichlorobenzene (8g, 42.6mmol, yield 86%) as a light brown solid. LCMS(M-2):186.0.

[0274] Step-2: Preparation of ethyl 1-(3,5-dichlorophenyl)-1H-1,2,3-triazole-4-carboxylate To a stirred solution of 1-azido-3,5-dichlorobenzene in 20 mL of dimethyl sulfoxide (2 g, 8.93 mmol), ethyl propiolate (6.47 μl, 63.8 mmol) was added at 25 °C. An aqueous solution of copper sulfate (1.1 g, 4.3 mmol) and L-ascorbic acid sodium salt (1.7 g, 8.5 mmol). The reaction mixture was stirred at 50 °C for 12 h. After completion of the reaction, the reaction mixture was cooled and poured into ice-cold water. The resulting solid was filtered, dried under reduced pressure, and purified by silica gel column chromatography to give ethyl 1-(3,5-dichlorophenyl)-1H-1,2,3-triazole-4-carboxylate (2.49 g, 8.7 mmol, 82% yield). (M-1): 285.45.

[0275] Step-3: Preparation of ethyl 1-(3,5-dichlorophenyl)-1H-1,2,3-triazole-4-carboxylate LiOH (2.26 g, 94 mmol) was dispensed into a stirred solution of ethyl 1-(3,5-dichlorophenyl)-1H-1,2,3-triazole-4-carboxylate (9 g, 31.5 mmol) in tetrahydrofuran (80 mL) / water (8 mL) at 25° C. and stirred at 25° C. for 16 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The resulting residue was neutralized with 10% aqueous HCl. The resulting solid was filtered and dried under reduced pressure to give 1-(3,5-dichlorophenyl)-1H-1,2,3-triazole-4-carboxylate (8 g, 31.0 mmol, 99% yield). (M-1): 257.45.

[0276] Step-4: Preparation of 1-(3,5-dichlorophenyl)-N-((2,5-dichlorophenyl)sulfonyl)-1H-1,2,3-triazole-4-carboxamide To a stirred solution of 1-(3,5-dichlorophenyl)-1H-1,2,3-triazole-4-carboxylic acid (400 mg, 1.56 mmol) in N,N-dimethylformamide (5 mL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (594 mg, 3.10 mmol) and 1-hydroxy-1-H-benzotriazole (419 mg, 3.10 mmol) were added at 25° C. To the resulting mixture, 4-dimethylaminopyridine (189 mg, 1.55 mmol) was added. The reaction mixture was stirred for 10 minutes, followed by the addition of 2,5-dichlorobenzenesulfonamide (421 mg, 1.90 mmol). The reaction mixture was then stirred at 25° C. for an additional 24 hours. After completion of the reaction, the reaction mixture was poured into ice water (40 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL) and the combined organic layers were washed with water (30 mL) and brine (30 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product, which was purified by silica gel column chromatography to give 1-(3,5-dichlorophenyl)-N-((2,5-dichlorophenyl)sulfonyl)-1H-1,2,3-triazole-4-carboxamide (70 mg, 0.15 mmol, 10% yield). LCMS(M+1):463.9. 1H-NMR (400 MHz, DMSO-d 6) :δ9.29(s, 1H), 8.11(d,J=1.6Hz,2H), 8.03(d,J=2.4Hz,1H), 7.77(t,J=1.6Hz,1H), 7.62(dd,J=2Hz, 1H), 7.55(d,J=8.4Hz,1H);LCMS(M+):466.8.

[0277] <Example 2> N-((2-chlorophenyl)sulfonyl)-1-(3,5-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide [ka] Step-1: Preparation of ethyl 1-(3,5-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate To a stirred solution of ethyl 3-oxobutanoate (0.415 g, 3.19 mmol) in dimethylsulfoxide (9 mL) / water (1 mL) mixture, piperidine (0.053 mL, 0.532 mmol) was added at 25° C., followed by 1-azido-3,5-dichlorobenzene (0.50 g, 2.66 mmol). The resulting mixture was stirred at 25° C. for 24 h. After completion of the reaction, the reaction mixture was poured into ice-cold water and the resulting solid was filtered and dried under reduced pressure to give ethyl 1-(3,5-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate (0.45 g, 1.50 mmol, 56% yield). (M+1): 301.8.

[0278] Step-3: Preparation of 1-(3,5-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid Lithium hydroxide monohydrate (0.052 g, 1.23 mmol) was added to a stirred solution of ethyl 1-(3,5-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate (0.123 g, 0.410 mmol) in tetrahydrofuran (9 mL) / water mixture (1 mL). The reaction mixture was stirred at 25° C. for an additional 16 h. After completion of the reaction, the solvent was evaporated. The resulting residue was diluted with water and neutralized by adding 10% aqueous HCl. The resulting solid was filtered and dried under reduced pressure to give 1-(3,5-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (0.08 g, 0.29 mmol, 72% yield). (M+1): 270.9.

[0279] Step-4: Preparation of N-(3,5-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide To a stirred solution of 1-(3,5-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (500 mg, 1.84 mmol) in a mixture of dichloromethane (5 mL) and tert-butanol (5 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (528 mg, 2.76 mmol) and 4-dimethylaminopyridine (674 mg, 5.51 mmol) were added and the resulting reaction mixture was stirred at 25° C. for 15 minutes. To this reaction mixture, 2-chlorobenzenesulfonamide (528 mg, 2.76 mmol) was added and stirred at the same temperature for another 24 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane (20 mL) and the organic layer was washed with water (10 mL) and 10% aqueous HCl (10 mL). Drying over anhydrous sodium sulfate and concentration under reduced pressure gave a crude product, which was purified by silica gel column chromatography to give N-(3,5-dichlorophenyl)-1-(280 mg, 0.63 mmol, yield 34%)-5-methyl-1H-1,2,3-triazole-4-carboxamide. 1 H-NMR (400 MHz, DMSO-d 6)δ8.16(dd,J=7.9,1.5Hz,1H), 7.93(t,J=1.8Hz,1H), 7.82(d,J=2.1Hz,2H), 7.71-7.57(m, 3H), 2.41(s, 3H); LCMS(M+1):446.9.

[0280] <Example 3> Preparation of N-((2-chloro-5-methoxyphenyl)sulfonyl)-1-(3,5-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide [ka] To a stirred solution of 1-(3,5-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (200 mg, 0.74 mmol) in N,N-dimethylformamide (5 mL), 4-dimethylaminopyridine (44.9 mg, 0.34 mmol), N,N-diisopropylethylamine (0.39 mL, 2.20 mmol) and HATU (363 mg, 1.0 mmol) was added. After 10 min, 2-chloro-5-methoxybenzenesulfonamide (163 mg, 0.74 mmol) was added. The reaction mixture was stirred for an additional 12 h at 25° C. After completion of the reaction, the reaction mixture was diluted with dichloromethane (15 mL) and neutralized by the addition of 10% aqueous HCl. The organic layer was separated, washed with water (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product, which was purified by silica gel column chromatography to give N-((2-chloro-5-methoxyphenyl)sulfonyl)-1-(3,5-dichlorophenyl)-5-methyl-1H-1,2,3 triazole-4-carboxamide (300 mg, 0.63 mmol, 86% yield). 1 HNMR (400 MHz, DMSO-d 6) :δ7.85(t,J=1.6Mz,1H), 7.78(d,J=1.6Mz,2H), 7.55(d,J=2.8Mz,1H), 7.29(d,J=8. 8Mz,1H), 6.97(dd,J=2.8,3.2Mz,1H), 3.78(s, 3H), 2.55(s, 3H);LCMS(M+1):476.9.

[0281] <Example 4> N-((2-chloro-5-methoxyphenyl)sulfonyl)-1-(3,3,3-trifluoropropyl)-1H-1,2,3-triazole-4-carboxamide [ka] Step-1: Preparation of ethyl 1-(3,3,3-trifluoropropyl)-1H-1,2,3-triazole-4-carboxylate To a stirred solution of 1,1,1-trifluoro-3-iodopropane (2 g, 8.93 mmol) in dimethyl sulfoxide (20 mL), sodium azide (0.581 g, 8.93 mmol) was added and stirring was continued for 12 hours at 25° C. Water (10 mL) was added to the reaction mass followed by ethyl propionate (0.91 mL, 8.93 mmol), L-ascorbic acid sodium salt (0.531 g, 2.68 mmol) and aqueous copper sulfate solution (0.33 g, 1.34 mmol) was added dropwise. The reaction mixture was stirred for another 12 hours at 25° C. After completion of the reaction, the reaction mixture was diluted with water (20 mL). The aqueous layer was extracted with ethyl acetate (2×20 mL) and the combined organic layers were washed with saturated aqueous brine solution (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give ethyl 1-(3,3,3-trifluoropropyl)-1H-1,2,3-triazole-4-carboxylate (1.8 g, 7.59 mmol, 85% yield) as a brown solid. (M+1): 238.0.

[0282] Step-2: Preparation of 1-(3,3,3-trifluoropropyl)-1H-1,2,3-triazole-4-carboxylic acid Lithium hydroxide (0.76 g, 31.6 mmol) was added to a stirred solution of ethyl 1-(3,3,3-trifluoropropyl)-1H-1,2,3-triazole-4-carboxylate (1.50 g, 6.32 mmol) in a tetrahydrofuran (10 mL) / water (2 mL) mixture and stirred at 25° C. for 12 h. After completion of the reaction, the solvent was evaporated. The resulting residue was diluted with water and acidified by adding 10% aqueous HCl. The resulting solid was filtered, washed with water, and dried under reduced pressure to give 1-(3,3,3-trifluoropropyl)-1H-1,2,3-triazole-4-carboxylic acid (1.1 g, 5.26 mmol, 83% yield) as a white solid. (M+1): 209.90.

[0283] Step-3: Preparation of N-(3,3,3-trifluoropropyl)-1-(2-chloro-5-methoxyphenyl)sulfonyl)-1H-1,2,3-triazole-4-carboxamide To a stirred solution of 4-dimethylaminopyridine (438 mg, 3.59 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (573 mg, 2.99 mmol) in tert-butanol (5 mL) / dichloromethane (5 mL), 1-(3,3,3-trifluoropropyl)-1H-1,2,3-triazole-4-carboxylic acid (250 mg, 1.12 mmol) was added and stirred at 25° C. for 15 minutes. Then, 2-chloro-5-methoxybenzenesulfonamide (244 mg, 1.10 mmol) was added and stirred at 25° C. for 12 hours. After completion of the reaction, the reaction mixture was diluted with water (10 mL). The aqueous layer was extracted with dichloromethane (2×10 mL), and the combined organic layers were washed with 10% aqueous HCl. Drying over anhydrous sodium sulfate and concentration under reduced pressure gave a crude product, which was purified by silica gel column chromatography to give N-((2-chloro-5-methoxyphenyl)sulfonyl)-1-(3,3,3-trifluoropropyl)-1H-1,2,3-triazole-4-carboxamide (270 mg, 0.65 mmol, yield 55%). 1 HNMR (400 MHz, DMSO-d 6):δ8.85(s, 1H), 7.60-7.55(m, 2H), 7.28(dd,J=2.8,3.2Mz,1H), 4.73-4.67(m, 2H), 3.84(s, 3H), 3.06-2.95(m, 2H);LCMS(M+1):412.9.

[0284] <Example 5> 1-(3,5-Dichlorobenzyl)-N-((2-fluorophenyl)sulfonyl)-1H-1,2,3-triazole-4-carboxamide [ka] Step-1: Preparation of ethyl 1-(3,5-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxylate To a stirred solution of 1-(bromomethyl)-3,5-dichlorobenzene in 10 mL of dimethyl sulfoxide (1 g, 4.17 mmol), sodium azide (0.27 g, 4.17 mmol) was added and the resulting mixture was stirred at 25° C. for 12 hours. Water (10 mL) was added to the reaction mixture followed by L-ascorbic acid sodium salt (0.25 g, 1.250 mmol), ethyl propiolate (0.42 mL, 4.17 mmol) and copper sulfate solution (0.156 g, 0.63 mmol). The reaction mixture was further stirred at 25° C. for 12 hours. After completion of the reaction, the reaction mixture was diluted with water (10 mL). The aqueous layer was extracted with ethyl acetate (2×15 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the crude product, which was purified by silica gel column chromatography to give ethyl 1-(3,5-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxylate (0.96 g, 3.20 mmol, 77% yield) as a greenish liquid. (M-1): 299.95.

[0285] Step-2: Preparation of 1-(3,5-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid Lithium hydroxide (0.399 g, 16.66 mmol) was added to a stirred solution of ethyl 1-(3,5-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxylate (1 g, 3.33 mmol) in a mixture of tetrahydrofuran (30 mL) and water (5 mL), and the mixture was stirred at 25° C. for 12 hours. After completion of the reaction, the solvent was removed under reduced pressure. The resulting residue was diluted with water and acidified by adding a 10% hydrochloric acid solution. The resulting solid was filtered, washed with water, and dried under reduced pressure to give 1-(3,5-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid (512 mg, 1.88 mmol, 56% yield) as a white solid. (M+1): 270.9.

[0286] Step-3: Preparation of 1-(3,5-dichlorobenzyl)-N-((2-fluorophenyl)sulfonyl)-1H-1,2,3-triazole-4-carboxamide To a stirred solution of 4-dimethylaminopyridine (337 mg, 2.76 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (440 mg, 2.297 mmol) in a mixture of tert-butanol (4 mL) and dichloromethane (4 mL), 1-(3,5-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid (250 mg, 0.92 mmol) was added, and the resulting reaction mixture was stirred at 25° C. for 15 minutes, followed by the addition of 2-fluorobenzenesulfonamide (148 mg, 0.86 mmol). The resulting reaction mixture was stirred at 25° C. for an additional 16 hours. After completion of the reaction, the reaction mixture was diluted with water (10 mL). The aqueous layer was extracted with dichloromethane (2×20 mL) and the combined organic layers were washed with 10% aqueous HCl. Drying over anhydrous sodium sulfate and concentration under reduced pressure gave a crude product, which was purified by silica gel column chromatography to give 1-(3,5-dichlorobenzyl)-N-((2-fluorophenyl)sulfonyl)-1H-1,2,3-triazole-4-carboxamide (110 mg, 0.256 mmol, 27.9% yield) as a white solid. 1 HNMR (400 MHz, DMSO-d 6):δ8.85(s, 1H), 8.0-7.96(m, 1H), 7.79-7.73(m, 1H), 7.63(t,J=4.0Mz,1H), 7.46-7.41(m, 4H), 5.68(s, 2H);LCMS(M+1):428.8.

[0287] <Example 6> N-(3,5-dichlorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide [ka] Step-1: Preparation of 1-(azidomethyl)-3,5-dichlorobenzene To a stirred solution of -3,5-dichlorobenzene (2.5 g, 10.42 mmol) in dimethyl sulfoxide (15 mL), sodium azide (0.813 g, 12.50 mmol) was added and stirred for 18 hours at 25° C. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (30 mL), washed with water (30 mL) and brine solution (30 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the crude product, which was purified by silica gel column chromatography to give -3,5-dichlorobenzene (1.80 g, 8.91 mmol, 86% yield). (M-1): 200.9.

[0288] Step-2: Preparation of ethyl 1-(3,5-dichlorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate To a stirred solution of ethyl 3-oxobutanoate (5.77 mL, 45.3 mmol) in dimethyl sulfoxide (50 mL), potassium carbonate (16.7 g, 121 mmol) was added followed by 1-(azidomethyl)-3,5-dichlorobenzene (6.10 g, 30.2 mmol). The resulting reaction mixture was stirred at 40° C. for 8 hours. After completion of the reaction, the reaction mixture was poured into ice-cold water. The resulting solid was filtered and dried under reduced pressure to obtain the crude product, which was purified by column chromatography on silica gel to obtain ethyl 1-(3,5-dichlorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate (7.8 g, 24.8 mmol, 82% yield). (M+1): 315.75.

[0289] Step-3: Preparation of 1-(3,5-dichlorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid To a stirred solution of ethyl 1-(3,5-dichlorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate (800 mg, 2.55 mmol) in a mixture of water (10 mL), tetrahydrofuran (30 mL) and ethanol (20 mL) was added lithium hydroxide (214 mg, 5.09 mmol). The resulting solution was stirred at 25° C. for 6 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was diluted with water and acidified by adding 10% aqueous HCl. The resulting solid was filtered and dried to give 1-(3,5-dichlorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (324 mg, 1.13 mmol, 44.5% yield) as a pale yellow solid. (M+1): 286.00.

[0290] Step-4: Preparation of N-(3,5-dichlorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide To a stirred solution of 4-dimethylaminopyridine (448 mg, 3.67 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (469 mg, 2.45 mmol) in a mixture of tert-butanol (5 mL) and dichloromethane (5 mL), 1-(3,5-dichlorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (350 mg, 1.22 mmol) was added and stirred for 15 minutes, followed by addition of 2-chlorobenzenesulfonamide (216 mg, 1.13 mmol). The resulting mixture was stirred at 25° C. for an additional 12 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane (10 mL) and washed with 10% aqueous HCl. Drying over anhydrous sodium sulfate and concentration under reduced pressure gave the crude product, which was purified by column chromatography on silica gel to give N-((2-chlorophenyl)sulfonyl)-1-(3,5-dichlorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide (386.7 mg, 0.84 mmol, 69% yield). 1 H-NMR (400 MHz, DMSO-d 6) δ12.97(s, NH), 8.14(dd,J=7.8,1.5Hz,1H), 7.71-7.57(m, 4H), 7.30(d,J=2.0Hz,2H), 5.63(s, 2H), 2.38(s, 3H); LCMS(M+1):460.80.

[0291] <Example 7> N-((4-chlorophenyl)sulfonyl)-1-(2,4-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxamide [ka] Step-1: Preparation of 1-(azidomethyl)-2,4-dichlorobenzene Sodium azide (2.17 g, 33.3 mmol) was added to a stirred solution of 1-(bromomethyl)-2,4-dichlorobenzene in 25 mL of dimethyl sulfoxide (5.0 g, 20.84 mmol) and stirred at 25 °C for 18 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate, washed with water, and then washed with brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the crude product. The resulting crude product was purified by column chromatography to obtain ethyl 1-(2,4-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxylate (4.8 g, 16.0 mmol, 77% yield). (M-1): 200.1.

[0292] Step-2: Preparation of ethyl 1-(2,4-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxylate 1-(azidomethyl)-2,4-dichlorobenzene (2.70 g, 13.36 mmol) in dimethyl sulfoxide (15 mL), L-ascorbic acid sodium salt (0.32 g, 1.60 mmol), ethyl propiolate (1.36 mL, 13.36 mmol) and An aqueous solution of copper(II) sulfate pentahydrate (0.334 g, 1.336 mmol) was slowly added. The resulting reaction mixture was stirred at 25° C. for 18 hours. After the reaction was completed, the reaction mixture was poured into ice water. The resulting solid was filtered, dried under reduced pressure, and then purified by silica gel column chromatography to obtain ethyl 1-(2,4-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxylate (1.5 g, 5.0 mmol, yield 37%). (M+1): 299.90.

[0293] Step-3: Preparation of 1-(2,4-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid Lithium hydroxide hydrate (0.4 g, 9.33 mmol) was added to a stirred solution of ethyl 1-(2,4-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxylate (1.40 g, 4.66 mmol) in a mixture of water (5 mL) / tetrahydrofuran (15 mL) / ethanol (10 mL), and the mixture was stirred at 25° C. for 6 hours. After completion of the reaction, the mixture was concentrated under reduced pressure to obtain a crude product, which was diluted with water and acidified by adding 10% aqueous HCl. The resulting solid was filtered and dried to obtain 1-(2,4-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid (1.2 g, 4.41 mmol, 95% yield). (M+1): 272.08.

[0294] Step-4: Preparation of N-((4-chlorophenyl)sulfonyl)-1-(2,4-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxamide To a stirred solution of 4-dimethylaminopyridine (550 mg, 4.50 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (493 mg, 2.57 mmol) in a mixture of tert-butanol (5 mL) and dichloromethane (5 mL), 1-(2,4-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid (350 mg, 1.3 mmol) was added and the reaction mixture was stirred for 15 minutes, followed by the addition of 4-chlorobenzenesulfonamide (247 mg, 1.286 mmol). The reaction mixture was further stirred at 25° C. for 12 hours, and after completion of the reaction, the reaction mixture was diluted with dichloromethane (10 mL) and washed with 10% aqueous HCl. Drying over anhydrous sodium sulfate and concentration under reduced pressure gave the crude product, which was purified by silica gel column chromatography to give N-((4-chlorophenyl)sulfonyl)-1-(2,4-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxamide (333.4 mg, 0.75 mmol, yield 58.2%). 1 H-NMR (400 MHz, DMSO-d 6)δ8.77(s, 1H), 7.98-7.95(m, 2H), 7.73-7.69(m, 3H), 7.48(dd,J=8.3,2.2Hz,1H), 7.35(d,J=8.3Hz,1H), 5.74(s, 2H);LCMS(M+1):446.80.

[0295] <Example 8> 1-(2,4-dichlorophenyl)-N-((2,5-dimethylphenyl)(methyl)(oxo)-λ 6 -Sulfaneilidene)-5-methyl-1H-1,2,3-triazole-4-carboxamide [ka] Step-1: Preparation of (2,5-dimethylphenyl)(methyl)sulfane To a stirred solution of 2,5-dimethylbenzenethiol (500 mg, 3.62 mmol) in N,N-dimethylformamide (10 mL) was added potassium carbonate (1000 mg, 7.23 mmol) and cooled to 0° C. Iodomethane (3.49 ml, 55.8 mmol) was added and the resulting reaction mixture was stirred at 25° C. for 24 h. After completion of the reaction, the reaction mixture was quenched in ice-cold water (20 mL). The aqueous layer was extracted with ethyl acetate (2×25 mL) and the combined organic layers were washed with saturated brine (30 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product, which was purified by silica gel column chromatography to give the desired product (2,5-dimethylphenyl)(methyl)sulfane (400 mg, 2.63 mmol, 72.6% yield). (M+1): 152.2.

[0296] Step--2: (2,5-dimethylphenyl)(imino)(methyl)-λ 6 - Preparation of sulfanone To a stirred solution of (2,5-dimethylphenyl)(methyl)sulfane (200 mg, 1.314 mmol) in methanol (30 mL) was added ammonium carbamate (205 mg, 2.63 mmol) at 0° C. The reaction mixture was warmed to 25° C. and diacetoxyiodobenzene (846 mg, 2.63 mmol) was added in portions at 25° C. over 15 min. The resulting reaction mixture was stirred at 25° C. for 16 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure to give the crude product, which was diluted with dichloromethane (50 mL). The organic layer was washed with water (100 mL) and saturated brine (50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the crude compound, which was purified by silica gel column chromatography to give (2,5-dimethylphenyl)(imino)(methyl)-λ 6- Sulfanone (144 mg, 0.788 mmol, 60% yield) was obtained. (M+1): 183.2.

[0297] Step-3: 1-(2,4-dichlorophenyl)-N-((2,5-dimethylphenyl)(methyl)(oxo)-λ 6 Preparation of -sulfaneilidene)-5-methyl-1H-1,2,3-triazole-4-carboxamide A solution of 1-(2,4-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (223 mg, 0.818 mmol) in dichloroethane (6 mL) was stirred at 25°C for 15 minutes with azabenzotriazole tetramethyluronium hexafluorophosphate (HATU) (622 mg, 1.637 mmol) and 4-dimethylaminopyridine (200 mg, 1.637 mmol), and then the mixture was cooled to room temperature and cooled to room temperature. 6-sulfanone (150 mg, 0.818 mmol) was added. The resulting reaction mixture was stirred at 25 °C for an additional 16 h. After completion of the reaction, the reaction mixture was diluted with water (20 mL) and the aqueous layer was extracted with dichloromethane (2 x 30 mL). The combined organic layers were separated and washed with 10% aqueous HCl (15 L). It was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product, which was purified by silica gel column chromatography to give 1-(2,4-dichlorophenyl)-N-((2,5-dimethylphenyl)(methyl)(oxo)-λ 6 -sulfaneilidene)-5-methyl-1H-1,2,3-triazole-4-carboxamide (215 mg, 0.492 mmol, 60.1% yield). 1 H-NMR (400 MHz, DMSO-d 6) δ8.00(d,J=2.1Hz,1H), 7.91(d,J=8.9Hz,1H), 7.85(s, 1H), 7.69(dq,J=8.9,1.2Hz,1H), 7.46(d,J=7.9 Hz,1H), 7.37(d,J=7.9Hz,1H), 3.58(s, 3H), 2.59(s, 3H), 2.39(s, 3H), 2.35(s, 3H);LCMS(M+1):487.2.

[0298] <Example 9> [ka] Step-1: Preparation of 1-azido-2,4-dichlorobenzene To a stirred solution of 1.5NHCl (123 mL, 185 mmol) and 2,4-dichloroaniline (10 g, 61.7 mmol) in methyl tert-butyl ether (50 mL), sodium nitrite (4.90 g, 71.0 mmol) was added as a solution in water (25 mL) at 0-5°C over 30 min. After the addition was complete, the reaction mixture was stirred at the same temperature for 15 min, and then sodium azide (4.41 g, 67.9 mmol) was added as a solution in water (25 mL) over 30 min. After the addition was complete, the reaction mixture was stirred at the same temperature for another 30 min. After the reaction was complete, the organic layer was washed with water (60 mL) and allowed to stand. It was diluted with NaHCO3 solution (60 mL), followed by DMSO (30 mL) and water (3 mL). The resulting mixture was concentrated under reduced pressure to remove methyl tert-butyl ether and used as is in Step-2. (M-1): 187.01.

[0299] Step-2: Preparation of ethyl 1-(2,4-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate To the crude solution of 1-azido-2,4-dichlorobenzene (11.6 g, 61.7 mmol) from Step-1, ethyl-3-oxobutanoate (9.45 mL, 74.0 mmol) and piperidine (1.2 mL, 12.34 mmol) were added to the reaction mixture, and the resulting mixture was stirred at 25° C. for 16 hours. After completion of the reaction, the reaction mixture was poured into ice-cold water (60 mL). The resulting precipitate was filtered, and the filter cake was washed with water and then with hexane. The solid was dried under reduced pressure to give ethyl 1-(2,4-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate (16.62 g, 55.4 mmol, 90% yield) as an off-white solid. M+1:300.10.

[0300] Step-3: Preparation of 1-(2,4-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid Using 1-(2,4-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-ethyl carboxylate (14.2 g, 52.2 mmol, yield 94%), 1-(2,4-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-ethyl carboxylate (16.6 g, 55.3 mmol) was synthesized according to the same procedure as in Step-3 of Example 2. (M+1): 271.90.

[0301] Step-4: Preparation of 2,5-dimethylbenzenesulfonyl chloride To a stirred solution of p-xylene (11.03 mL, 89 mmol) in dichloromethane (50 mL), chlorosulfuric acid (17.87 ml, 268 mmol) as a solution in dichloromethane (50 mL) was added dropwise over 1 h to the reaction mixture at 0-5 °C, and the resulting mixture was further stirred at 25 °C for 4 h. After completion of the reaction, the reaction mixture was poured into ice water (150 mL). The aqueous layer was extracted with dichloromethane (3 x 150 mL) and the combined organic layers were washed with saturated sodium bicarbonate solution (100 mL), brine (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the crude product 2,5-dimethylbenzenesulfonyl chloride (17.8 g, 87 mmol, 97% yield), which was used in the next step without purification.

[0302] Step-5: Preparation of 2,5-dimethylbenzenesulfonylamide Ammonia (32 mL, 415 mmol) was added dropwise to a stirred solution of 2,5-dimethylbenzenesulfonyl chloride (17 g, 83 mmol) in tetrahydrofuran (50 mL) at 0-5° C. over 30 minutes, and the mixture was further stirred at 25° C. for 1 hour. After the reaction was completed, the reaction mixture was concentrated under reduced pressure to obtain a white solid, which was filtered, and the filter cake was washed with water, after which hexane (50 mL) was added and dried under reduced pressure to obtain 2,5-dimethylbenzenesulfonamide (14.5 g, 78 mmol, yield 94%) as a white solid. (M-1): 183.9.

[0303] Step-6: 1-(2,4-dichlorophenyl)-N-((2,5-dimethylphenyl)sulfonyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide Using 1-(2,4-dichlorophenyl)-N-((2,5-dimethylphenyl)sulfonyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid and 2,5-dimethylbenzenesulfonamide as starting materials, 1-(2,4-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide was synthesized according to the procedure described in Step-4 of Example 2. 1 H-NMR (400 MHz, DMSO-d 6) δ12.94(s, 1H), 8.05(d,J=1.8Hz,1H), 7.86(d,J=0.9Hz,1H), 7.78-7.72(m, 2H), 7.39(d,J=7 .6Hz,1H), 7.29(d,J=7.6Hz,1H), 2.59(s, 3H), 2.36(s, 3H), 2.25(s, 3H);LCMS(M+1):440.0.

[0304] Table A: Representative compounds of the present disclosure were prepared according to the appropriate methods described in the respective schemes and examples. [Table 4] TIFF2025503242000061.tif184128 TIFF2025503242000062.tif182128 TIFF2025503242000063.tif183128 TIFF2025503242000064.tif174128 TIFF2025503242000065.tif183128 TIFF2025503242000066.tif179128 TIFF2025503242000067.tif180128 TIFF2025503242000068.tif182128 TIFF2025503242000069.tif188128 TIFF2025503242000070.tif172128 TIFF2025503242000071.tif174128 TIFF2025503242000072.tif187128 TIFF2025503242000073.tif181128 TIFF2025503242000074.tif185128 TIFF2025503242000075.tif186128 TIFF2025503242000076.tif180128 TIFF2025503242000077.tif181128 TIFF2025503242000078.tif189128 TIFF2025503242000079.tif177128 TIFF2025503242000080.tif172128 TIFF2025503242000081.tif177128 TIFF2025503242000082.tif185128 TIFF2025503242000083.tif175128 TIFF2025503242000084.tif185128 TIFF2025503242000085.tif187128 TIFF2025503242000086.tif183128 TIFF2025503242000087.tif185128 TIFF2025503242000088.tif160128 TIFF2025503242000089.tif171128 TIFF2025503242000090.tif175128 TIFF2025503242000091.tif182128 TIFF2025503242000092.tif171128 TIFF2025503242000093.tif176128 TIFF2025503242000094.tif183128 TIFF2025503242000095.tif187128 TIFF2025503242000096.tif188128 TIFF2025503242000097.tif183128 TIFF2025503242000098.tif184128 TIFF2025503242000099.tif172128 TIFF2025503242000100.tif182128 TIFF2025503242000101.tif170128 TIFF2025503242000102.tif182128 TIFF2025503242000103.tif182128 TIFF2025503242000104.tif177128 TIFF2025503242000105.tif186128 TIFF2025503242000106.tif175128 TIFF2025503242000107.tif183128 TIFF2025503242000108.tif182128 TIFF2025503242000109.tif184128 TIFF2025503242000110.tif181128 TIFF2025503242000111.tif178128 TIFF2025503242000112.tif175128 TIFF2025503242000113.tif175128 TIFF2025503242000114.tif176128 TIFF2025503242000115.tif183128 TIFF2025503242000116.tif184128 TIFF2025503242000117.tif184128 TIFF2025503242000118.tif179128 TIFF2025503242000119.tif178128 TIFF2025503242000120.tif174128 TIFF2025503242000121.tif185128 TIFF2025503242000122.tif169128 TIFF2025503242000123.tif169128 TIFF2025503242000124.tif177128 TIFF2025503242000125.tif179128 TIFF2025503242000126.tif179128 TIFF2025503242000127.tif179128 TIFF2025503242000128.tif182128 TIFF2025503242000129.tif60128*Compound names generated using Chemdraw Professional 19.1

[0305] As described herein, the compounds of formula (I) exhibit high nematicidal activity against nematodes that attack important agricultural crops. The compounds of the present invention were evaluated for their activity against one or more of the following nematodes:

[0306] [Biological Examples] Biological test examples of plant parasitic nematodes Example 1: Meloidogyne incognita test Test pots were filled with a 1:1:1 mixture of sand:soil:coco peat. 5 mL of nematode suspension (Meloidogyne incognita, 5000 eggs mixed with J2) was added to the soil in each pot. One hour later, the prescribed concentration of each test compound was applied to each pot. Ten-day-old cucumber seedlings were transplanted into the pots the day after application. The seedlings were grown at 27°C under greenhouse conditions. Gall scores were recorded 30 days after application. The plants were carefully uprooted and the roots were thoroughly washed. Gall scores were scored on a 0 to 10 scale as described by Zeck (1971) as follows: 0=no galls 1 = Very few small galls 2=Many small galls 3 = Many small galls, some growing together 4 = Many small galls and some large galls 5 = 25% of the roots are severely damaged 6 = 50% of roots are severely damaged 7 = 75% of the roots are severely damaged 8=No healthy roots, but plant is still green 9=Roots are rotting and plants are dying 10=Plants and roots are dead Compounds 2, 7, 8, 17, 25, 33, 35, 52, 56, 57, 61, 76, 96, 97,108,132,133,134,135,140, 143,168,171,209,210,217,218,227,228,229,230,231,240,241,242,245,246 ,250,252,253,254,259,260,261,269,271,272,278,279,280,281,311,315,316,328,335,336,337,338,339,364,370,371,378,389,390,394,395,396,410,4 13,415,430,432,433,441,443,445,446,458,459,460,497,499,513,516,536,538,563,586,587,588,590,596,597,598,599,610,630,631,640,657,664,66 No. 5,666, 667, 668, 669, 670, 671, 672, 673, 674, 675, 676, 683, 687, 689, 690, 691, 709, 736, 774 and 776 recorded a gall rating scale of less than 4 at 1000 ppm, while untreated tests had severe galls (up to 8).

Claims

1. A compound of formula (I) 【Chemistry 1】 Formula (I) Here, R １ teeth, 【Chemistry 2】 and Where: 【change】 represents the point of attachment to the triazole ring, or R １ is C １ ~C ６ -Haloalkyl, C ２ ~C ６ -Alkenyl, C ２ ~C ６ -Alkynyl, C ３ ~C ８ -Cycloalkyl, C ３ ~C ８ -Halocycloalkyl and C ３ ~C ８ -Cycloalkyl-C １ ~C ６ - alkyl, R １ C １ ~C ６ -Haloalkyl, C ２ ~C ６ -Alkenyl, C ２ ~C ６ -Alkynyl, C ３ ~C ８ -Cycloalkyl, C ３ ~C ８ -Halocycloalkyl and C ３ ~C ８ -Cycloalkyl-C １ ~C ６ -Alkyl groups are halogen, CN, R ６ａ , OR ６ａ , S(O) ｎ R ６ａ , N(R ６ａ ) ２ and COOR ６ａ and optionally substituted with one or more groups selected from the group consisting of R １ａ is hydrogen, halogen, CN, OR ６ａ , C １～ C ６ -Alkyl and C １～ C ６ -haloalkyl; R １ａ Each group is a halogen, CN, R ６ａ , OR ６ａ , S(O) ｎ R ６ａ , N(R ６ａ ) ２ , COOR ６ａ and C.O.N.R. ６ａ and optionally substituted with one or more groups selected from the group consisting of R １ｂ is halogen, CN, C １ ~C ６ -Alkyl, C １ ~C ６ -Haloalkyl, C ２ ~C ６ -Alkenyl, C ２ ~C ６ -Alkynyl, C １ ~C ６ -Alkoxy, C １ ~C ６ -Haloalkoxy, C ３ ~C ８ -Cycloalkyl, C ３ ~C ８ -Halocycloalkyl, S(O) ｎ R ６ａ and C ３ ~C ８ -Cycloalkyl-C １ ~C ６ -alkyl, where R １ｂ Each group is a halogen, R ６ａ , OR ６ａ , S(O) ｎ R ６ａ , N(R ６ａ ) ２ , COOR ６ａ and C.O.N.R. ６ａ and optionally substituted with one or more groups selected from the group consisting of R ２ is hydrogen, halogen, CN, C １ ~C ６ -Alkyl, C １ ~C ６ -Haloalkyl, C １ ~C ６ -Alkoxy, C ３ ~C ６ - selected from the group consisting of cycloalkyl and phenyl, wherein the phenyl ring is not further selected from halogen, CN, C １ ~C ４ -Alkyl, C １ ~C ４ -Alkoxy and C １ ~C ４ -haloalkyl, Z is Z-1 or Z-2; 【Chemistry 3】 where * represents the point of attachment to the carbonyl group attached to the triazole ring; R ３ is hydrogen, C １ ~C ６ -Alkyl, C １ ~C ６ -Haloalkyl, C １ ~C ６ -Alkoxy, C ３ ~C ６ -Cycloalkyl and C ３ ~C ８ -Cycloalkyl-C １ ~C ６ -alkyl, where R ３ Each group may be optionally substituted with halogen; A １ , A ２ and A ３ represents C or N, where A １ , A ２ and A ３ Two or less of the above represent N, R ４ is hydrogen, halogen, CN, OR ６ , C １ ~C ６ -Alkyl, C １ ~C ６ -Haloalkyl, C ２ ~C ６ -alkenyl, and C ２ ~C ６ -alkynyl, R ５ is hydrogen, halogen, CN, nitro, (C=O)-R ６ , O(C=O)-R ６ , OR ６ , N(R ６ ) ２ , C.R. ６ =NR ６ , COOR ６ , CON(R ６ ) ２ , (C=S)-N(R ６ ) ２ , S(O) ｎ R ６ , OS(O) ｎ R ６ , S(O) ｎ N (R ６ ) ２ , -S(=O) ０～１ R ７ (=N-R ６ ), -N=S(=O) ０～１ (R ７ ) ２ , C １ ~C ６ -Alkyl, C １ ~C ６ -Haloalkyl, C ２ ~C ６ -Alkenyl, C ２ ~C ６ -Alkynyl, C ３ ~C ８ -Cycloalkyl, C ３ ~C ８ -Halocycloalkyl, C ３ ~C ８ -Cycloalkyl-C １ ~C ６ -Alkyl, phenyl, C ３ ~C ６ - selected from the group consisting of carbocyclyl and heterocyclic 3- to 6-membered ring, where R ５ Each group is a halogen, R ６ａ , OR ６ａ , S(O) ｎ R ６ａ , N(R ６ａ ) ２ , COOR ６ａ and C.O.N.R. ６ａ and optionally substituted with one or more groups selected from the group consisting of R ６ is hydrogen, hydroxy, C １ ~C ６ -Alkyl, C １ ~C ６ -Alkoxy, C １ ~C ６ -Haloalkyl, C ２ ~C ６ -Alkenyl, C ２ ~C ６ -Alkynyl, C ３ ~C ８ -Cycloalkyl and C ３ ~C ８ -Cycloalkyl-C １ ~C ６ - alkyl, R ６ａ is hydrogen, C １ ~C ６ -Alkyl, C １ ~C ６ -Haloalkyl and C ３ ~C ８ -cycloalkyl, R ７ and R ８ are independently hydrogen, C １ ~C ６ -Alkyl, C １ ~C ６ -Haloalkyl, C ２ ~C ６ -Alkenyl and C ３ ~C ８ -Cycloalkyl and C ３ ~C ８ -Cycloalkyl-C １ ~C ６ - alkyl, n is an integer selected from 0 to 2; or a salt, stereoisomer, polymorph or N-oxide thereof, provided that 1H-1,2,3-triazole-4-carboxamide, 1-(2-cyclopropylethyl)-N-[(2,3-difluorophenyl)sulfonyl], 1H-1,2,3-triazole-4-carboxamide, N-[(4-bromo-2-chlorophenyl)sulfonyl]-1-(2-cyclopropylethyl), 1H-1,2,3-triazole-4-carboxamide, 1-(2-cyclopropylethyl) )-N-[[3-[(dimethylamino)carbonyl]phenyl]sulfonyl], 1H-1,2,3-triazole-4-carboxamide, 1-cyclohexyl-N-[[3-(4-methyl-2-thiazolyl)phenyl]sulfonyl] and 1H-1,2,3-triazole-4-carboxamide, 1-cyclopropyl-5-(difluoromethyl)-N-[[4-methyl-3-(trifluoromethyl)phenyl]sulfonyl] are excluded from the definition of the compound of formula (I); compound.

2. R １ but 【Chemistry 4】 and Where: 【change】 represents the point of attachment to the triazole ring, A compound of formula (I) according to claim 1.

3. Z is Z-1; A compound of formula (I) according to claim 1 or 2.

4. Z is Z-2; A compound of formula (I) according to claim 1 or 2.

5. R ２ is hydrogen, halogen, CN, C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl, C １ ~C ４ - selected from the group consisting of alkoxy, cyclopropyl and phenyl, wherein said phenyl ring may be optionally substituted with one or more groups selected from the group consisting of halogen, CN, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, difluoromethyl and trifluoromethyl, A compound of formula (I) according to any one of claims 1 to 4.

6. The compound of formula (I) is represented by formula (Ia-1): 【Chemistry 5】 Formula (Ia-1) A compound of formula (I) according to claim 1, represented by Here, R １ａ is hydrogen, halogen, CN, OR ６ａ , C １ ~C ４ -Alkyl and C １ ~C ４ -haloalkyl, where R １ａ Each group is selected from halogen, CN and R ６ａ and optionally substituted with one or more groups selected from the group consisting of R １ｂ is halogen, CN, C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl, C ２ ~C ４ -Alkenyl, C ２ ~C ４ -Alkynyl, C １ ~C ４ -Alkoxy, C １ ~C ４ -Haloalkoxy, C ３ ~C ６ -Cycloalkyl, C ３ ~C ６ -Halocycloalkyl and C ３ ~C ６ -Cycloalkyl-C １ ~C ４ -alkyl, where R １ｂ Each group is a halogen, R ６ａ , OR ６ａ and S(O) ｎ R ６ａ and optionally substituted with one or more groups selected from the group consisting of R ２ is hydrogen, halogen, CN, C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl, C １ ~C ４ - selected from the group consisting of alkoxy, cyclopropyl and phenyl, wherein the phenyl ring is not further selected from the group consisting of halogen, CN, C １ ~C ４ -Alkyl, C １ ~C ４ -Alkoxy and C １ ~C ４ -haloalkyl, R ３ is hydrogen, C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl and C ３ ~C ８ -Cycloalkyl-C １ ~C ４ - alkyl, R ４ is hydrogen, halogen, CN, OR ６ , C １ ~C ４ -Alkyl and C １ ~C ４ -haloalkyl, R ５ is hydrogen, halogen, CN, nitro, (C=O)-R ６ , OR ６ , N(R ６ ) ２ , S(O) ｎ R ６ , C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl, C ３ ~C ６ -Cycloalkyl, C ３ ~C ６ -Halocycloalkyl, C ３ ~C ６ -Cycloalkyl-C １ ~C ４ -Alkyl, phenyl, C ３ ~C ６ - selected from the group consisting of carbocyclyl and heterocyclic 3- to 6-membered ring, where R ５ Each group is a halogen, R ６ａ and optionally substituted with one or more groups selected from the group consisting of R ６ａ is hydrogen, C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl and C ３ ~C ６ -cycloalkyl, R ６ is hydrogen, hydroxy, C １ ~C ４ -Alkyl, C １ ~C ４ -Alkoxy, C １ ~C ４ -Haloalkyl, C ２ ~C ４ -Alkenyl, C ２ ~C ４ -Alkynyl and C ３ ~C ６ -Cycloalkyl and C ３ ~C ６ -Cycloalkyl-C １ ~C ４ - alkyl, n is an integer selected from 0 to 2; or a salt, stereoisomer, polymorph or N-oxide thereof; compound.

7. The compound of formula (I) is represented by formula (Ia-2): 【Chemistry 6】 Formula (Ia-2) A compound of formula (I) according to claim 1, represented by Here, R １ｂ is halogen, CN, C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl, C ２ ~C ４ -Alkenyl, C ２ ~C ４ -Alkynyl, C １ ~C ４ -Alkoxy, C １ ~C ４ -Haloalkoxy, C ３ ~C ６ -Cycloalkyl, C ３ ~C ６ -Halocycloalkyl and C ３ ~C ６ -Cycloalkyl-C １ ~C ４ -alkyl, where R １ｂ Each group is a halogen, R ６ａ , OR ６ａ and S(O) ｎ R ６ａ and optionally substituted with one or more groups selected from the group consisting of R ２ is hydrogen, halogen, CN, C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl, C １ ~C ４ - selected from the group consisting of alkoxy, cyclopropyl and phenyl, wherein the phenyl ring is not further selected from the group consisting of halogen, CN, C １ ~C ４ -Alkyl, C １ ~C ４ -Alkoxy and C １ ~C ４ -haloalkyl, R ３ is hydrogen, C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl and C ３ ~C ８ -Cycloalkyl-C １ ~C ４ - alkyl, R ４ is hydrogen, halogen, CN, OR ６ , C １ ~C ４ -Alkyl and C １ ~C ４ -haloalkyl, R ５ is hydrogen, halogen, CN, nitro, (C=O)-R ６ , OR ６ , N(R ６ ) ２ , S(O) ｎ R ６ , C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl, C ３ ~C ６ -Cycloalkyl, C ３ ~C ６ -Halocycloalkyl, C ３ ~C ６ -Cycloalkyl-C １ ~C ４ -Alkyl, phenyl, C ３ ~C ６ - selected from the group consisting of carbocyclyl and heterocyclic 3- to 6-membered ring, where R ５ Each group is a halogen, R ６ａ may be substituted with one or more groups selected from the group consisting of R ６ａ is hydrogen, C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl and C ３ ~C ６ -cycloalkyl, R ６ is hydrogen, hydroxy, C １ ~C ４ -Alkyl, C １ ~C ４ -Alkoxy, C １ ~C ４ -Haloalkyl, C ２ ~C ４ -Alkenyl, C ２ ~C ４ -Alkynyl and C ３ ~C ６ -Cycloalkyl and C ３ ~C ６ -Cycloalkyl-C １ ~C ４ - alkyl, n is an integer selected from 0 to 2; or a salt, stereoisomer, polymorph or N-oxide thereof; compound.

8. The compound of formula (I) is represented by formula (Ia-3): 【Chemistry 7】 Formula (Ia-3) A compound of formula (I) according to claim 1, represented by Here, R １ｂ is halogen, CN, C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl, C ２ ~C ４ -Alkenyl, C ２ ~C ４ -Alkynyl, C １ ~C ４ -Alkoxy, C １ ~C ４ -Haloalkoxy, C ３ ~C ６ -Cycloalkyl, C ３ ~C ６ -Halocycloalkyl and C ３ ~C ６ -Cycloalkyl-C １ ~C ４ -alkyl, where R １ｂ Each group is a halogen, R ６ａ , OR ６ａ and S(O) ｎ R ６ａ and optionally substituted with one or more groups selected from the group consisting of R ２ is hydrogen, halogen, CN, C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl, C １ ~C ４ - selected from the group consisting of alkoxy, cyclopropyl and phenyl, wherein the phenyl ring is not further selected from the group consisting of halogen, CN, C １ ~C ４ -Alkyl, C １ ~C ４ -Alkoxy and C １ ~C ４ -haloalkyl, R ３ is hydrogen, C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl and C ３ ~C ８ -Cycloalkyl-C １ ~C ４ - alkyl, R ４ is hydrogen, halogen, CN, OR ６ , C １ ~C ４ -Alkyl and C １ ~C ４ -haloalkyl, R ５ is hydrogen, halogen, CN, nitro, (C=O)-R ６ , OR ６ , N(R ６ ) ２ , S(O) ｎ R ６ , C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl, C ３ ~C ６ -Cycloalkyl, C ３ ~C ６ -Halocycloalkyl, C ３ ~C ６ -Cycloalkyl-C １ ~C ４ -Alkyl, phenyl, C ３ ~C ６ - selected from the group consisting of carbocyclyl and heterocyclic 3- to 6-membered ring, where R ５ Each group is a halogen, R ６ａ may be substituted with one or more groups selected from the group consisting of R ６ａ is hydrogen, C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl and C ３ ~C ６ -cycloalkyl, R ６ is hydrogen, hydroxy, C １ ~C ４ -Alkyl, C １ ~C ４ -Alkoxy, C １ ~C ４ -Haloalkyl, C ２ ~C ４ -Alkenyl, C ２ ~C ４ -Alkynyl and C ３ ~C ６ -Cycloalkyl and C ３ ~C ６ -Cycloalkyl-C １ ~C ４ - alkyl, n is an integer selected from 0 to 2; or a salt, stereoisomer, polymorph or N-oxide thereof; compound.

9. A compound of formula (I) according to any one of claims 1 to 5, Here, R １ａ is hydrogen, halogen, CN, OR ６ａ , C １ ~C ４ -Alkyl and C １ ~C ４ -haloalkyl, where R １ａ Each group is selected from halogen, CN and R ６ａ and optionally substituted with one or more groups selected from the group consisting of R １ｂ is halogen, CN, C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl, C ２ ~C ４ -Alkenyl, C ２ ~C ４ -Alkynyl, C １ ~C ４ -Alkoxy, C １ ~C ４ -Haloalkoxy, C ３ ~C ６ -Cycloalkyl, C ３ ~C ６ -Halocycloalkyl and C ３ ~C ６ -Cycloalkyl-C １ ~C ４ -alkyl, where R １ｂ Each group is a halogen, R ６ａ , OR ６ａ and S(O) ｎ R ６ａ and optionally substituted with one or more groups selected from the group consisting of R ４ is hydrogen, halogen, CN, OR ６ , C １ ~C ４ -Alkyl and C １ ~C ４ -haloalkyl, R ５ is hydrogen, halogen, CN, nitro, OR ６ , C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl, C ３ ~C ６ -Cycloalkyl, C ３ ~C ６ -Cycloalkyl-C １ ~C ４ -Alkyl and C ３ ~C ６ -carbocyclyl, where R ５ Each group is a halogen and R ６ａ and optionally substituted with one or more groups selected from the group consisting of R ６ is hydrogen, hydroxy, C １ ~C ４ -Alkyl, C １ ~C ４ -Alkoxy, C １ ~C ４ -Haloalkyl, C ２ ~C ４ -Alkenyl, C ２ ~C ４ -Alkynyl, C ３ ~C ６ -Cycloalkyl and C ３ ~C ６ -Cycloalkyl-C １ ~C ４ - alkyl, R ６ａ is hydrogen, C １ ~C ４ -Alkyl, C １ ~C ４ -Haloalkyl and C ３ ~C ６ - selected from the group consisting of cycloalkyl, A compound of formula (I) according to any one of claims 1 to 5.

10. A process for the preparation of a compound of formula (I) according to claim 1, comprising steps selected from a) to d): a) reacting a compound of formula (11) with a compound of formula (9) in the presence of a suitable base and a suitable solvent to obtain a compound of formula (13), which is further reacted with a hydrolysis reagent in the presence of a suitable solvent to obtain a compound of formula (4y); 【Chemistry 8】 b) reacting the compound of formula (4y) with a compound of formula (2) in the presence of a suitable reagent, a suitable solvent and a suitable base to obtain a compound of formula (Ib-b); 【Chemistry 9】 c) the compound of formula (Ib) is obtained by reacting a compound of formula (Ib-b) with a compound of formula (14) in the presence of a suitable solvent and a suitable base, 【Chemistry 10】 d) Compounds of formula (Id) can be obtained by reacting compounds of formula (4y) with compounds of formula (15) in the presence of a suitable coupling reagent, a suitable solvent and a suitable base. 【Chemistry 11】 Methods for producing compounds.

11. A method for the preparation of a pharmaceutical composition comprising the compound of formula (I) according to claim 1 and one or more inert carriers. composition.

12. The composition may further comprise one or more active compatible compounds selected from fungicides, insecticides, nematicides, acaricides, biocides, herbicides, plant growth regulators or fertilizers. The composition of claim 11.

13. the concentration of the compound of formula (I) ranges from 1 to 90% by weight relative to the total weight of the composition, preferably from 5 to 50% by weight relative to the total weight of the composition; 13. The composition according to claim 11 or 12.

14. 13. A combination comprising a compound of formula (I) according to claim 1 and one or more active compatible compounds selected from fungicides, insecticides, nematicides, acaricides, biocides, herbicides, plant growth regulators or fertilizers.

15. A compound of formula (I) according to claim 1, or a composition according to claim 11, or a combination according to claim 14 for the control or prevention of agricultural and / or horticultural crops against nematodes. use.

16. The agricultural crops are selected from cereals, corn, rice, soybeans and other legumes, fruits and fruit trees, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbits, oil plants, tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton, potato, tomato, onion, pepper, other vegetables and ornamentals, Use of a compound of formula (I) according to claim 15.

17. The compound of formula (I) according to claim 1, or the composition according to claim 11, or the combination according to claim 14, wherein the amount of the compound of formula (I) ranges from 0.1 g to 10 kg per 100 kg of seeds. seed.

18. A method for controlling or preventing the infestation of useful plants by phytopathogenic nematodes in agricultural and / or horticultural crops, comprising: applying a compound of formula (I) as claimed in claim 1 or a composition as claimed in claim 11 or a combination as claimed in claim 14 to said plant, its part or locus; method.

19. A method for controlling or preventing the infestation of useful plants by phytopathogenic nematodes in agricultural and / or horticultural crops, comprising: A compound of formula (I) as claimed in claim 1 or a composition as claimed in claim 11 or a combination as claimed in claim 14 is applied to the seeds of the plant. method.

20. 1. A method for controlling or preventing phytopathogenic nematodes in agricultural and / or horticultural crops, comprising: with a compound of formula (I) according to claim 1, a composition according to claim 11 or a combination according to claim 14, comprising the step of applying an effective dose of said compound or said composition or said combination in an amount ranging from 1 g to 5 kg per hectare of agricultural and / or horticultural crops. method.

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