1,4,2-oxathiazole-based pesticides and methods of making and using thereof

Abstract

Provided herein are 1,4,2-oxathiazoles that can exhibit antifungal activity, insecticidal activity, and / or herbicidal activity. Also provided are compositions comprising these 1,4,2-oxathiazoles and analogs thereof as well as methods of using these compounds and compositions as pesticides (i.e., herbicides, insecticides, fungicides, or a combination thereof).

Description

[0001] Attorney Docket No. 10620-164W02

[0002] NCSURef.: 2025-138-04

[0003] 1,4,2-Oxathiazole-Based Pesticides and Methods of Making and Using Thereof

[0004] STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT

[0005] This invention was made with government support under GM139583 awarded by the National Institutes of Health, and 1454845 awarded by the National Science Foundation. The government has certain rights in the invention.

[0006] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims benefit of priority of U. S. Provisional Application No.

[0007] 63 / 778,322, filed March 26, 2025, and U. S. Provisional Application No. 63 / 891,146, filed September 30, 2025, each of which is hereby incorporated by reference herein in its entirety.

[0008] BACKGROUND

[0009] Heterocycles are ubiquitous in agrochemical and therapeutic agents, and they are found in more than 90% of the current drugs being developed, with N, O, and 5 being the three most common heteroatoms present within. Five-membered / V- and O- containing heterocycles represent a significant population of recently FDA approved pharmaceuticals and crop protections agents, with thiazoles and isoxazoles each being among the top 25 most frequent N-containing heterocycles in U. S. FDA approved agents. Additionally, heterocyclic five-membered rings displaying denser population of heteroatoms (2+) such as 1,3,4- and 1,2,4-oxadiazoles have been commonly used to improve the pharmacokinetics and dynamics of the native compounds.

[0010] The 2-isoxazoline class of five-membered heterocycles exists as the core scaffold for numerous marketed fungicides and insecticides focused on crop protections and in veterinary medicine. By a similar fashion, 1,2,4-oxadiazoles have been widely used as nematocidal agents for crop protection. Fungicidal agents such as oxathiapiprolin, approved in 2015 by US EP A, fluoxapiprolin, approved in 2018 and pyrisoxazole, approved in the EU in 2019 have been widely used for crop protection. Other 2-isoxazoles have several applications, such as insecticides and insecticidal agents for veterinary use Additionally, other 1,2,4-oxadiazoles such as tioxazaphen has been used as nematicidal agents.Attorney Docket No. 10620-164W02

[0011] NCSURef.: 2025-138-04

[0012] Deep-seated modifications of these scaffolds could lead to newer molecular entities with broader antimicrobial spectrum, improved pharmacokinetic properties, or bioactivity enhancement. However, new methods to access heteroatom rings and bio-isosteres with single atom modifications to known, underrepresented heterocycles are scarce, yet would provide new avenues of exploration about SAR by providing new classes of chemical probes.

[0013] SUMMARY

[0014] 1,4,2-Oxathiazoles are a highly underreported class of N, O, S- containing heterocycles. When disregarding the 5- heteroatom within this motif, this scaffold represents an alternative to the heavily prevalent A- and O- containing five-membered heterocycles. Regarding crop protecting agents, the 3,5-biaryl substituted 2-isoxazolines exist as the core scaffold for numerous marketed fungicides, nematicides (e.g. fluxametamide, thioxazafen, etc.) and insecticides. To that end, a method to access similar molecules containing sulfur would represent a potentially valuable deep-seated modification to the core of numerous bioactive molecules.

[0015] Accordingly, provided herein are compounds defined by Formula IV below

[0016] R5

[0017] /

[0018]

[0019] (RA)„

[0020] Formula IV

[0021] wherein A represents an aryl or heteroaryl group; R5represents halogen or haloalkyl; R6represents hydrogen, halogen, or haloalkyl; R7represents halogen or haloalkyl; RAis chosen from hydroxy, halogen, -CN, -NO2, amino, alkylamino, dialkylamino, alkyl, haloalkyl; alkylthio; haloalkylthio; alkoxy, haloalkoxy, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxy carbonyl, haloalkoxy carbonyl, alkylaminocarbonyl, heteroalkylaminocarbonyl, dialkylaminocarbonyl, heterodialkylaminocarbonyl, nitrone, sulfonic acid, sulfonamido, thiol, phosphonate, phosphinyl, aldehyde, trimethylsilyl, hydrazino, azido, isocyanate, aryl, and heteroaryl; n is 0, 1, 2, or 3; and E represents an amido group. For example, in someAttorney Docket No. 10620-164W02

[0022] NCSURef.: 2025-138-04

[0023] embodiments, the compound can comprise one of the following:

[0024] Cl

[0025]

[0026] Also described herein are agrichemical compositions comprising a 1,4,2-oxathiazoles or analog thereof described herein, as well as methods of using these compounds and compositions as fungicides, herbicides, and insecticides.

[0027] BRIEF DESCRIPTION OF THE DRAWINGS

[0028] Figure 1. Summary of the insecticidal activity of example compounds described herein.

[0029] DETAILED DESCRIPTION

[0030] Definitions

[0031] Terms used herein will have their customary meaning in the art unless specified otherwise. The organic moieties mentioned when defining variable positions within the general formulae described herein (e.g., the term “halogen”) are collective terms for the individual substituents encompassed by the organic moiety. The prefix Cn-Cmindicates in each case the possible number of carbon atoms in the group.Attorney Docket No. 10620-164W02

[0032] NCSURef.: 2025-138-04

[0033] The term “alkyl,” as used herein, refers to saturated straight, branched, cyclic, primary, secondary or tertiary hydrocarbons, including those having 1 to 20 atoms. In some embodiments, alkyl groups will include C1-C12, C1-C10, Ci-Cs, Ci-C6, C1-C5, C1-C4, C1-C3, C1-C2, or Ci alkyl groups. Examples of C1-C10 alkyl groups include, but are not limited to, 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, l-ethyl-2 -methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl groups, as well as their isomers. Examples of Ci-C4-alkyl groups include, for example, methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl and 1,1 -dimethylethyl groups.

[0034] Cyclic alkyl groups or “cycloalkyl” groups, which are encompassed alkyl, include cycloalkyl groups having from 3 to 10 carbon atoms. Cycloalkyl groups can include a single ring, or multiple condensed rings. In some embodiments, cycloalkyl groups include C3-C4, C4-C7, C5-C7, C4-C6, or Cs-Ce cyclic alkyl groups. Non-limiting examples of cycloalkyl groups include adamantyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like.

[0035] Alkyl groups can be unsubstituted or substituted with one or more moieties selected from the group consisting of alkyl, halo, haloalkyl, hydroxyl, carboxyl, acyl, acyloxy, amino, alkyl- or dialkylamino, amido, arylamino, alkoxy, aryloxy, nitro, cyano, azido, thiol, imino, sulfonic acid, sulfate, sulfonyl, sulfanyl, sulfinyl, sulfamonyl, ester, phosphonyl, phosphinyl, phosphoryl, phosphine, thioester, thioether, acid halide, anhydride, oxime, hydrazine, carbamate, phosphoric acid, phosphate, phosphonate, or any other viable functional group that does not inhibit the biological activity of the compounds of the invention, either unprotected, or protected as necessary, as known to those skilled in the art, for example, as described in Greene, et al., Protective Groups in Organic Synthesis, John Wiley and Sons, Third Edition, 1999, hereby incorporated by reference.

[0036] Terms including the term “alkyl,” such as “alkylcycloalkyl,” “cycloalkylalkyl,” “alkylamino,” or “dialkylamino,” will be understood to comprise an alkyl group as defined above linked to another functional group, where the group is linked to the compound through the last group listed, as understood by those of skill in the art.

[0037] The term “alkenyl,” as used herein, refers to both straight and branched carbon chains which have at least one carbon-carbon double bond. In some embodiments, alkenyl groups canAttorney Docket No. 10620-164W02

[0038] NCSURef.: 2025-138-04

[0039] include C2-C20 alkenyl groups. In other embodiments, alkenyl can include C2-C12, C2-C10, C2-C8, C2-C6 or C2-C4 alkenyl groups. In one embodiment of alkenyl, the number of double bonds is 1 -3, in another embodiment of alkenyl, the number of double bonds is one or two. Other ranges of carbon-carbon double bonds and carbon numbers are also contemplated depending on the location of the alkenyl moiety on the molecule. “C2-Cio-alkenyl” groups may include more than one double bond in the chain. The one or more unsaturations within the alkenyl group may be located at any position(s) within the carbon chain as valence permits. In some embodiments, when the alkenyl group is covalently bound to one or more additional moieties, the carbon atom(s) in the alkenyl group that are covalently bound to the one or more additional moieties are not part of a carbon-carbon double bond within the alkenyl group. Examples of alkenyl groups include, but are not limited to, ethenyl, 1 -propenyl, 2-propenyl, 1 -methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1 -methyl- 1 -propenyl, 2-methyl-l -propenyl, 1 -methyl-2-propenyl, 2-methyl- 2-propenyl; 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl- 1-butenyl, 2-methyl-l-butenyl, 3-methyl- 1-butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, l,l-dimethyl-2-propenyl, 1,2-dimethyl-1 -propenyl, 1,2-dimethyl-2-propenyl, 1 -ethyl- 1 -propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1 -methyl- 1-pentenyl, 2-methyl-l -pentenyl, 3-methyl-l -pentenyl, 4-methyl-l -pentenyl, l-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2 -pentenyl, 1-methy 1-3 -pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3 -pentenyl, l-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, l,l-dimethyl-2-butenyl, l,l-dimethyl-3-butenyl, 1,2-dimethyl- 1-butenyl, 1.2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl- 1 -butenyl, 1,3-dimethyl-2-butenyl, 1.3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl- 1-butenyl, 2,3-dimethyl-2-butenyl, 2.3-dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-2-butenyl, 1 -ethyl- 1-butenyl, 1-ethyl-2-butenyl, l-ethyl-3 -butenyl, 2-ethyl- 1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, l,l,2-trimethyl-2-propenyl, 1 -ethyl- 1-methy 1-2-propenyl, l-ethyl-2 -methyl- 1 -propenyl and 1-ethyl-2-methyl-2-propenyl groups.

[0040] The term “alkynyl,” as used herein, refers to both straight and branched carbon chains which have at least one carbon-carbon triple bond. In one embodiment of alkynyl, the number of triple bonds is 1-3; in another embodiment of alkynyl, the number of triple bonds is one or two. In some embodiments, alkynyl groups include from C2-C20 alkynyl groups. In other embodiments, alkynyl groups may include C2-C12, C2-C10, C2-C8, C2-C6 or C2-C4 alkynyl groups. Other ranges of carbon-carbon triple bonds and carbon numbers are also contemplated depending on the location of the alkenyl moiety on the molecule. For example, the term ”C2-Cio-alkynyl” asAttorney Docket No. 10620-164W02

[0041] NCSURef.: 2025-138-04

[0042] used herein refers to a straight-chain or branched unsaturated hydrocarbon group having 2 to 10 carbon atoms and containing at least one triple bond, such as ethynyl, prop-l-yn-l-yl, prop-2 -yn-1-yl, n-but-l-yn-l-yl, n-but-l-yn-3-yl, n-but-l-yn-4-yl, n-but-2-yn-l-yl, n-pent-l-yn-l-yl, n-pent-l-yn-3-yl, n-pent-l-yn-4-yl, n-pent-l-yn-5-yl, n-pent-2-yn-l-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-l-yn-3-yl, 3-methylbut-l-yn-4-yl, n-hex-l-yn-l-yl, n-hex-l-yn-3-yl, n-hex-l-yn-4-yl, n-hex-l-yn-5-yl, n-hex-l-yn-6-yl, n-hex-2-yn-l-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-l-yl, n-hex-3-yn-2-yl, 3-methylpent-l-yn-l-yl, 3-methylpent-l-yn-3-yl, 3 -methylpent- l-yn-4-yl, 3 -methylpent- l-yn-5-yl, 4-methylpent-l-yn-l-yl, 4-methylpent-2-yn-4-yl, and 4-methylpent-2-yn-5-yl groups.

[0043] The term “haloalkyl,” as used herein refers to an alkyl group, as defined above, which is substituted by one or more halogen atoms. In some instances, the haloalkyl group can be an alkyl group substituted by one or more fluorine atoms. In certain instances, the haloalkyl group can be a perfluorinated alkyl group. For example, Ci-C4-haloalkyl includes, but is not limited to, chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, di chlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, and pentafluoroethyl.

[0044] The term “haloalkenyl,” as used herein, refers to an alkenyl group, as defined above, which is substituted by one or more halogen atoms.

[0045] The term “haloalkynyl,” as used herein, refers to an alkynyl group, as defined above, which is substituted by one or more halogen atoms.

[0046] The term “alkoxy,” as used herein, refers to alkyl-O-, wherein alkyl refers to an alkyl group, as defined above. Similarly, the terms “alkenyloxy,” “alkynyloxy,” “haloalkoxy,” “haloalkenyloxy,” “haloalkynyloxy,” “cycloalkoxy,” “cycloalkenyloxy,” “halocycloalkoxy,” and “halocycloalkenyloxy” refer to the groups alkenyl-O-, alkynyl-O-, haloalkyl-O-, haloalkenyl-O-, haloalkynyl-O-, cycloalkyl-O-, cycloalkenyl-O-, halocycloalkyl-O-, and halocycloalkenyl-O-, respectively, wherein alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkenyl, halocycloalkyl, and halocycloalkenyl are as defined above. Examples of Ci-Ce-alkoxy include, but are not limited to, methoxy, ethoxy, C2H5-CH2O-, (CHsECHO-. n-butoxy, C2HS-CH(CH3)O-, (CH3)2CH-CH2O-, (CH3)3CO-, n-pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1 -dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethyl-propoxy, 1-ethylpropoxy, n-hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1 -dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-Attorney Docket No. 10620-164W02

[0047] NCSURef.: 2025-138-04

[0048] dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1 -ethyl- 1 -methylpropoxy, and l-ethyl-2-methylpropoxy.

[0049] The term “alkylthio,” as used herein, refers to alkyl-S-, wherein alkyl refers to an alkyl group, as defined above. Similarly, the terms “haloalkylthio,” “cycloalkylthio,” and the like, refer to haloalkyl-S- and cycloalkyl-S- where haloalkyl and cycloalkyl are as defined above.

[0050] The term “alkylsulfinyl,” as used herein, refers to alkyl-S(O)-, wherein alkyl refers to an alkyl group, as defined above. Similarly, the term “haloalkylsulfinyl” refers to haloalkyl-S(O)-where haloalkyl is as defined above.

[0051] The term “alkylsulfonyl,” as used herein, refers to alkyl-S(O)2-, wherein alkyl is as defined above. Similarly, the term “haloalkylsulfonyl” refers to haloalkyl-S(O)2- where haloalkyl is as defined above.

[0052] The terms “alkylamino” and “dialkylamino,” as used herein, refer to alkyl-NH- and (alkyl)2N- groups, where alkyl is as defined above. Similarly, the terms “haloalkylamino” and “halodialkylamino” refer to haloalkyl-NH- and (haloalkyl)2-NH-, where haloalkyl is as defined above.

[0053] The terms “alkylcarbonyl,” “alkoxycarbonyl,” “alkylaminocarbonyl,” and “dialkylaminocarbonyl,” as used herein, refer to alkyl-C(O)-, alkoxy-C(O)-, alkylamino-C(O)-and dialkylamino-C(O)- respectively, where alkyl, alkoxy, alkylamino, and dialkylamino are as defined above. Similarly, the terms “haloalkylcarbonyl,” “haloalkoxy carbonyl,” “haloalkylaminocarbonyl,” and “dihaloalkylaminocarbonyl,” as used herein, refer to the groups haloalkyl-C(O)-, haloalkoxy-C(O)-, haloalkylamino-C(O)-, and dihaloalkylamino-C(O)-, where haloalkyl, haloalkoxy, haloalkylamino, and dihaloalkylamino are as defined above.

[0054] The term “aryl,” as used herein, refers to a monovalent aromatic carbocyclic group of from 6 to 14 carbon atoms. Aryl groups can include a single ring or multiple condensed rings. In some embodiments, aryl groups include Ce-Cio aryl groups. Aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, tetrahydronaphtyl, phenylcyclopropyl and indanyl. Aryl groups may be unsubstituted or substituted by one or more moieties selected from halogen, cyano, nitro, hydroxy, mercapto, amino, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, halocycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, haloalkenyloxy, haloalkynyloxy, cycloalkoxy, cycloalkenyloxy, halocycloalkoxy, halocycloalkenyloxy, alkylthio, haloalkylthio, cycloalkylthio, halocycloalkylthio, alkylsulfinyl, alkenylsulfinyl, alkynyl-sulfinyl, haloalkylsulfinyl, haloalkenylsulfinyl, haloalkynylsulfinyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl,Attorney Docket No. 10620-164W02

[0055] NCSURef.: 2025-138-04

[0056] haloalkyl-sulfonyl, haloalkenylsulfonyl, haloalkynylsulfonyl, alkylamino, alkenylamino, alkynylamino, di(alkyl)amino, di(alkenyl)-amino, di(alkynyl)amino, or trialkylsilyl.

[0057] The term “alkylaryl,” as used herein, refers to an aryl group that is bonded to a parent compound through a diradical alkylene bridge, (-CH2-)n, where n is 1-12 and where “aryl” is as defined above.

[0058] The term “alkylcycloalkyl,” as used herein, refers to a cycloalkyl group that is bonded to a parent compound through a diradical alkylene bridge, (-CH2-)n, where n is 1-12 and where “cycloalkyl” is as defined above. The term “cycloalkylalkyl,” as used herein, refers to a cycloalkyl group, as defined above, which is substituted by an alkyl group, as defined above.

[0059] The term “heteroalkyl,” as used herein, refers to an alkyl group, as described above, which includes one or more heteroatoms (e.g., from one to four heteroatoms) within the carbon backbone. In some cases, the heteroatom(s) incorporated into the carbon backbone are oxygen, nitrogen, sulfur, or combinations thereof. The terms “heteroalkenyl” and “heteroalkynyl,” as used herein, likewise refer to alkenyl and alkynyl groups respectively which include one or more heteroatoms (e.g., from one to four heteroatoms, such as oxygen, nitrogen, sulfur, or combinations thereof) within their carbon backbone.

[0060] The term “heteroaryl,” as used herein, refers to a monovalent aromatic group of from 1 to 15 carbon atoms (e.g., from 1 to 10 carbon atoms, from 2 to 8 carbon atoms, from 3 to 6 carbon atoms, or from 4 to 6 carbon atoms) having one or more heteroatoms within the ring. The heteroaryl group can include from 1 to 4 heteroatoms, from 1 to 3 heteroatoms, or from 1 to 2 heteroatoms. In some cases, the heteroatom(s) incorporated into the ring are oxygen, nitrogen, sulfur, or combinations thereof. When present, the nitrogen and sulfur heteroatoms may optionally be oxidized. Heteroaryl groups can have a single ring (e.g., pyridyl or furyl) or multiple condensed rings provided that the point of attachment is through a heteroaryl ring atom. Preferred heteroaryls include pyridyl, piridazinyl, pyrimidinyl, pyrazinyl, triazinyl, pyrrolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinnyl, furanyl, thiophenyl, furyl, pyrrolyl, imidazolyl, oxazolyl, isoxazolyl, isothiazolyl, pyrazolyl benzofuranyl, and benzothiophenyl. Heteroaryl rings may be unsubstituted or substituted by one or more moieties as described for aryl above.

[0061] The term “alkylheteroaryl,” as used herein, refers to a heteroaryl group that is bonded to a parent compound through a diradical alkylene bridge, (-CH2-)n, where n is 1-12 and where “heteroaryl” is as defined above.

[0062] The terms “cycloheteroalkyl,” “heterocyclyl,” “heterocyclic,” and “heterocyclo” are used herein interchangeably, and refer to fully saturated or unsaturated, cyclic groups, for example, 3Attorney Docket No. 10620-164W02

[0063] NCSURef.: 2025-138-04

[0064] to 7 membered monocyclic or 4 to 7 membered monocyclic; 7 to 11 membered bicyclic, or 10 to 15 membered tricyclic ring systems, having one or more heteroatoms within the ring. The heterocyclyl group can include from 1 to 4 heteroatoms, from 1 to 3 heteroatoms, or from 1 to 2 heteroatoms. In some cases, the heteroatom(s) incorporated into the ring are oxygen, nitrogen, sulfur, or combinations thereof. When present, the nitrogen and sulfur heteroatoms may optionally be oxidized, and the nitrogen heteroatoms may optionally be quatemized. The heterocyclyl group may be attached at any heteroatom or carbon atom of the ring or ring system and may be unsubstituted or substituted by one or more moieties as described for aryl groups above.

[0065] Exemplary monocyclic heterocyclic groups include, but are not limited to, pyrrolidinyl, pyrrolyl, pyrazolyl, oxetanyl, pyrazolinyl, imidazolyl, imidazolinyl, imidazolidinyl, oxazolyl, oxazolidinyl, isoxazolinyl, isoxazolyl, thiazolyl, thiadiazolyl, thiazolidinyl, isothiazolyl, isothiazolidinyl, furyl, tetrahydrofuryl, thienyl, oxadiazolyl, piperidinyl, piperazinyl, 2-oxopiperazinyl, 2-oxopiperidinyl, 2-oxopyrrolodinyl, 2-oxoazepinyl, azepinyl, 4-piperidonyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, tetrahydropyranyl, morpholinyl, thiamorpholinyl, thiamorpholinyl sulfoxide, thiamorpholinyl sulfone, 1,3-di oxolane and tetrahydro- 1,1-dioxothienyl, triazolyl, triazinyl, and the like.

[0066] Exemplary bicyclic heterocyclic groups include, but are not limited to, indolyl, benzothiazolyl, benzoxazolyl, benzodioxolyl, benzothienyl, quinuclidinyl, quinolinyl, tetra-hydroisoquinolinyl, isoquinolinyl, benzimidazolyl, benzopyranyl, indolizinyl, benzofuryl, chromonyl, coumarinyl, benzopyranyl, cinnolinyl, quinoxalinyl, indazolyl, pyrrolopyridyl, furopyridinyl (such as furo[2,3-c]pyridinyl, furo[3,2-b]pyridinyl]or furo[2,3-b]pyridinyl), dihydroisoindolyl, dihydroquinazolinyl (such as 3,4-dihydro-4-oxo-quinazolinyl), tetrahydroquinolinyl and the like.

[0067] Exemplary tricyclic heterocyclic groups include carbazolyl, benzidolyl, phenanthrolinyl, acridinyl, phenanthridinyl, xanthenyl, and the like.

[0068] The term “alkylheterocyclyl” and “alkylcycloheteroalkyl” are used herein interchangeably, and refer to a heterocyclyl group that is bonded to a parent compound through a diradical alkylene bridge, (-CH2-)n, where n is 1-12 and where “heterocyclyl” is as defined above. The term “heterocyclylalkyl,” as used herein, refers to a heterocyclyl group, as defined above, which is substituted by an alkyl group, as defined above.

[0069] The term “halogen,” as used herein, refers to the atoms fluorine, chlorine, bromine and iodine. The prefix halo- (e.g., as illustrated by the term haloalky 1) refers to all degrees ofAttorney Docket No. 10620-164W02

[0070] NCSURef.: 2025-138-04

[0071] halogen substitution, from a single substitution to a perhalo substitution (e.g., as illustrated with methyl as chloromethyl (-CH2CI), dichloromethyl (-CHCh), trichloromethyl (-CCI3)).

[0072] As used herein, the term “substituted” is contemplated to include all permissible substituents of organic compounds. In a broad aspect, the permissible substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, and aromatic and nonaromatic substituents of organic compounds. Illustrative substituents include, for example, those described below. The permissible substituents can be one or more and the same or different for appropriate organic compounds. For purposes of this disclosure, the heteroatoms, such as nitrogen, can have hydrogen substituents and / or any permissible substituents of organic compounds described herein which satisfy the valences of the heteroatoms. This disclosure is not intended to be limited in any manner by the permissible substituents of organic compounds. Also, the terms “substitution” or “substituted with” include the implicit proviso that such substitution is in accordance with permitted valence of the substituted atom and the substituent, and that the substitution results in a stable compound, e.g, a compound that does not spontaneously undergo transformation such as by rearrangement, cyclization, elimination, etc.

[0073] As used herein, herbicide and herbicidal active ingredient mean a compound that controls undesirable vegetation when applied in an appropriate amount.

[0074] As used herein, control of or controlling undesirable vegetation means killing or preventing the vegetation, or causing some other adversely modifying effect to the vegetation e.g., deviations from natural growth or development, regulation, desiccation, retardation, and the like.

[0075] As used herein, a herbicidally effective or vegetation controlling amount is an amount of herbicidal active ingredient the application of which controls the relevant undesirable vegetation.

[0076] As used herein, applying a herbicide or herbicidal composition means delivering it directly to the targeted vegetation or to the locus thereof or to the area where control of undesired vegetation is desired. Methods of application include, but are not limited to pre-emergently contacting soil or water, post-emergently contacting the undesirable vegetation or area adjacent to the undesirable vegetation.

[0077] As used herein, plants and vegetation include, but are not limited to, dormant seeds, germinant seeds, emerging seedlings, plants emerging from vegetative propagules, immature vegetation, and established vegetation.

[0078] As used herein, agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity, or that are or can be converted in plants, water, or soil to the referenced herbicide. Exemplary agriculturally acceptable esters are those that are or can byAttorney Docket No. 10620-164W02

[0079] NCSURef.: 2025-138-04

[0080] hydrolyzed, oxidized, metabolized, or otherwise converted, e.g., in plants, water, or soil, to the corresponding carboxylic acid which, depending on the pH, may be in the dissociated or undissociated form.

[0081] Suitable salts include those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Preferred cations include sodium, potassium, magnesium, and aminium cations of the formula:

[0082] R13R14R15R16N+

[0083] wherein R13, R14, R15and R16each, independently represents hydrogen or C1-C12 alkyl, C3-C12 alkenyl or C3-C12 alkynyl, each of which is optionally substituted by one or more hydroxy, C1-C4 alkoxy, C1-C4 alkylthio or phenyl groups, provided that R13, R14, R15and R16are sterically compatible. Additionally, any two R13, R14, R15and R16together may represent an aliphatic difunctional moiety containing one to twelve carbon atoms and up to two oxygen or sulfur atoms. Salts of the compounds of Formula I can be prepared by treatment of compounds of Formula I with a metal hydroxide, such as sodium hydroxide, with an amine, such as ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, bisallylamine, 2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine or with a tetraalkylammonium hydroxide, such as tetramethylammonium hydroxide or choline hydroxide. Amine salts are often preferred forms of the compounds of Formula I because they are water-soluble and lend themselves to the preparation of desirable aqueous based herbicidal compositions.

[0084] Compounds of the Formula I can include N-oxides. Pyridine N-oxides can be obtained by oxidation of the corresponding pyridines. Suitable oxidation methods are described, for example, in Houben-Weyl, Methoden der orgcmischen Chemie [Methods in organic chemistry], expanded and subsequent volumes to the 4th edition, volume E 7b, p. 565 f.

[0085] Compounds

[0086] Provided herein are 1,4,2-oxathiazoles that can exhibit activity as antifungal agents, herbicidal agents, and / or insecticidal agents.

[0087] For example, provided herein are compounds defined by Formula IV belowAttorney Docket No. 10620-164W02

[0088] NCSURef.: 2025-138-04

[0089]

[0090] Formula IV

[0091] wherein A represents an aryl or heteroaryl group; R5represents halogen or haloalkyl; R6represents hydrogen, halogen, or haloalkyl; R7represents halogen or haloalkyl; RAis chosen from hydroxy, halogen, -CN, -NO2, amino, alkylamino, dialkylamino, alkyl, haloalkyl; alkylthio; haloalkylthio; alkoxy, haloalkoxy, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxy carbonyl, haloalkoxy carbonyl, alkylaminocarbonyl, heteroalkylaminocarbonyl, dialkylaminocarbonyl, heterodialkylaminocarbonyl, nitrone, sulfonic acid, sulfonamido, thiol, phosphonate, phosphinyl, aldehyde, trimethylsilyl, hydrazino, azido, isocyanate, aryl, and heteroaryl; n is 0, 1, 2, or 3; and E represents an amido group. For example, in some embodiments, the compound can comprise one of the following:

[0092] Cl

[0093]

[0094] Attorney Docket No. 10620-164W02

[0095] NCSURef.: 2025-138-04

[0096]

[0097] 1.4.2-()xathiazole Analogs of Furalaner, Afoxolaner, and Lotilaner

[0098] In some examples, described herein are 1,4,2-oxathiazole analogs of furalaner, afoxolaner, and lotilaner. Furalaner, afoxolaner, and lotilaner and related compounds are described for example in International Publication No. WO 2014 / 090918, WO 2005 / 085216 (furalaner), WO 2010 / 079077 (afoxolaner), WO 2011 / 157748 (lotilaner) and U. S. Patent Nos.

[0099] 7,662,972 (furalaner), 8,022,089 (furalaner), 8,138,213 (furalaner), and 8,377,942 (afoxolaner), each of which is incorporated by reference in its entirety. Described herein are analogs of these compounds which include a 1,4,2-oxathiazole ring or an oxidized analog thereof.

[0100] For example, described herein are compounds of Formula VIII or a salt thereof:

[0101]

[0102] wherein

[0103] Y is chosen from S, S=O, and S(=O)2;

[0104] D-A1, D-A2and D-A3are carbon;

[0105] D-G is a benzene ring;

[0106] D-W is an oxygen atom or sulfur atom;Attorney Docket No. 10620-164W02

[0107] NCSURef.: 2025-138-04

[0108] D-X is halogen atom, cyano, nitro, azido, — SCN, — SFs, Ci-Ce alkyl, Ci-Ce alkyl arbitrarily substituted with D-R4, Cs-Cs cycloalkyl, Cs-Cs cycloalkyl arbitrarily substituted with D-R4, C2-C6 alkenyl, C2-C6 alkenyl arbitrarily substituted with D-R4, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C6 alkynyl, C2-C6 alkynyl arbitrarily substituted with D-R4, — OH, — O(D-R5), — OSO2(D-R5), — SH, — S(O)r(D-R5), — N=CHO(D-R8), — N=C(D-R9)O(D-R8), — CHO, — C(O) (D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(O)NH(D-R10), — C(O)N(D-R10) (D-R9), — C(S)O(D-R9), — C(S)S(D-R9), — C(S)NH(D-R10), — C(S)N(D-R10)(D-R9)— CH=NO(D-R11), — C(D-R9)=NO(D-R11), — S(O)2O(D-R9), — S(O)2NH(D-R10), — S(O)2N(D-R10) (D-R9), — Si(D-R13)(D-R14) (D-R12), phenyl, phenyl substituted with (Z)Pi, D-l to D-65, E-l to E-45, when m is 2, 3, 4 or 5, each D-X may be identical with or different from each other,

[0109] further, when two D-Xs are adjacent, the adjacent two D-Xs may form 5 -membered or 6-membered ring together with carbon atoms to which the two D-Xs are bonded by forming — CH2CH2CH2—, — CH2CH2O—, — CH2OCH2—, — OCH2O—, — CH2CH2S—, — CH2SCH2—, — CH2CH2N(D-R15)—, — CH2N(D-R15)CH2—, — CH2CH2CH2CH2—, — CH2CH2CH2O—, — CH2CH2OCH2—, — CH2OCH2O—, — OCH2CH2O—, — OCH2CH2S—, — CH2CH=CH—, — OCH=CH—, — SCH=CH—, — N(D-R15)CH=CH—, — OCH=N—, — SCH=N—, — N(D-R15)CH=N—, — N(D-R15)N=CH—, — CH=CHCH=CH— or — OCH2CH=CH—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with Z, further when the hydrogen atoms are substituted with two or more Zs at the same time, each Z may be identical with or different from each other;

[0110] D-Y is halogen atom, cyano, nitro, azido, — SCN, — SFs, Ci-Ce alkyl, Ci-Ce alkyl arbitrarily substituted with D-R4, C3-C8 cycloalkyl, C3-C8 cycloalkyl arbitrarily substituted with D-R4, C2-C6 alkynyl, C2-C6 alkynyl arbitrarily substituted with D-R4, — OH, — O(D-R5), — OSO2(D-R5), — SH, — S(O)r(D-R5), — NH(D-R7), — N(D-R7) (D-R6), — N=CHO(D-R8), — N=C(D-R9)O(D-R8), — C(O)NH(D-R10), — C(O)N(D-R10) (D-R9), — C(S)NH(D-R10), — C(S)N(D-R10) (D-R9), — Si(D-R13)(D-R14)(D-R12), phenyl, phenyl substituted with (Z)Pi, D-l to D-65, E-l to E-45, when n is 2, 3 or 4, each D-Y may be identical with or different from each other,

[0111] further, when two D-Ys are adjacent, the adjacent two D-Ys may form 5 -membered or 6-membered ring together with carbon atoms to which the two D-Ys are bonded by forming — CH2CH2CH2—, — CH2CH2O—, — CH2OCH2—, — OCH2O—, — CH2CH2S—, — CH2SCH2—, — SCH2S—, — CH2CH2CH2CH2—, — CH2CH2CH2O—, — CH2CH2OCH2—, — CH2OCH2O—, — OCH2CH2O—, — OCH2CH2S—, — SCH2CH2S—, — OCH=N— or — SCH=N—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substitutedAttorney Docket No. 10620-164W02

[0112] NCSURef.: 2025-138-04

[0113] with Z, further when the hydrogen atoms are substituted with two or more Zs at the same time, each Z may be identical with or different from each other;

[0114] D-R1and D-R2independently of each other are hydrogen atom, cyano, C1-C12 alkyl, Ci-C12 alkyl arbitrarily substituted with D-R16, C3-C12 cycloalkyl, C3-C12 cycloalkyl arbitrarily substituted with D-R16, C2-C 12 alkenyl, C2-C12 alkenyl arbitrarily substituted with D-R16, C3-C12 cycloalkenyl, C3-i2halocycloalkenyl, C3-Ci2alkynyl, C3-Ci2alkynyl arbitrarily substituted with D-R16, — S(D-R9), — S(O)2(D-R9), — SN(D-R18) (D-R17), — S(O)2N(D-R10)(D-R9), — O(D-R19), — N(D-R20)(D-R19), — N=CH(D-R19b), — N=C(D-R19b)(D-R19a), — CHO, — C(O)(D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(O)N(D-R10)(D-R9), — C(S)O(D-R9), — C(S)S(D-R9), — C(S)N(D-R10)(D-R9), — C(=N-D-R11)O(D-R9), — C(=N-D-R11)S(D-R9), — C(=N-D-R11)N(D-R10) (D-R9), phenyl, phenyl substituted with (Z)Pi, D-l to D-65, or E-l to E-49,

[0115] or D-R1and D-R2together form =C(D-R2a)(D-Rla), or D-R1and D-R2together may form 3- to 5-membered ring together with the nitrogen atom bonding them by forming C2-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, Ci-Ce alkyl, Ci-Cehaloalkyl, Ci-Ce alkoxy (Ce)alkyl, Ci-Ce alkoxy, formyl, Ci-Ce alkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci-Ce alkoxy carbonyl, Ci-Ce haloalkoxycarbonyl, Ci-Ce alkylaminocarbonyl, Ci-Ce haloalkylaminocarbonyl, phenyl or phenyl substituted with (Z)Pi, or in case where substituent D-Y is present at the adjacent position, D-R2together with D-Y may form a 5-membered ring together with the atom bonding them by forming — CH2 —, — CH2CH2 —, — CH2O —, — CH2S —, — CH2N(D-R6) —, — CH=CH — or — CH=N —, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, Ci-C ealkyl, Ci-Ce haloalky 1, Ci-Ce alkylidene, Ci-Cehaloalkylidene, oxo orthioxo,

[0116] D-Rlaand D-R2atogether may form a 5- or 6-membered ring together with the carbon atom bonding them by forming C4-C5 alkylene chain or C4-C5 alkenylene chain, in this case, the alkylene chain and the alkenylene chain may contain one to three oxygen atoms or sulfur atoms, or D-Rlaand D-R2atogether may form a 5-membered ring together with the carbon atom bonding them by forming C4 alkylene chain or C4 alkenylene chain, in this case, the alkylene chain and the alkenylene chain may contain one to three nitrogen atoms, and either ring may be arbitrarily substituted with halogen atom, Ci-Ce alkyl, Ci-Cehaloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio or Ci-Cehaloalkylthio;

[0117] D-R3is cyano, Ci-Ce alkyl arbitrarily substituted with D-R4, C3-C8 cycloalkyl, C3-C8 cycloalkyl arbitrarily substituted with D-R4, C3-C6 alkenyl, C2-C6 alkenyl arbitrarily substituted with D-R4, C3-C6 alkynyl, C2-C6 alkynyl arbitrarily substituted with D-R4, — O(D-R5), —Attorney Docket No. 10620-164W02

[0118] NCSURef.: 2025-138-04

[0119] S(O)r(D-R5), — N(D-R10)(D-R9), — CHO, — C(O)(D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(O)NH(D-R10), — C(O)N(D-R10)(D-R9), — C(S)O(D-R9), — C(S)S(D-R9), — C(S)NH(D-R10), — C(S)N(D-R10)(D-R9), — CH=NO(D-Rn), — C(D-R9)=NO(D-Rn), — Si(D-R13)(D-R14)(D-R12), — P(O)(O-D-R21)2, phenyl, phenyl substituted with (Z)Pi, D-l to D-65, or E-l to E-45;

[0120] D-l to D-65 are aromatic heterocyclic rings of the following formulae, respectively

[0121]

[0122] Attorney Docket No. 10620-164W02

[0123] NCSURef.: 2025-138-04

[0124]

[0125] Attorney Docket No. 10620-164W02

[0126] NCSURef.: 2025-138-04

[0127]

[0128] Attorney Docket No. 10620-164W02

[0129] NCSURef.: 2025-138-04

[0130]

[0131] Z is halogen atom, cyano, nitro, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4haloalkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Ci-C4haloalkylthio Ci-C4alkyl, Ci-C4alkylsulfinyl Ci-C4alkyl, Ci-C4haloalkylsulfinyl Ci-C4alkyl, Ci-C4alkylsulfonyl Ci-C4alkyl, Ci-C4haloalkylsulfonyl Ci-C4alkyl, Cs-Cecycloalkyl, Cs-Cehalocycloalkyl, — OH, Ci-Cealkoxy, Ci-Cehaloalkoxy, Ci-Cealkylsulfonyloxy, Ci-Cehaloalkylsulfonyloxy, Ci-Cealkylthio, Ci-Cehaloalkylthio, Ci-Cealkylsulfinyl, Ci-Cehaloalkylsulfinyl, Ci-Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl, — NH2, Ci-Cealkylamino, di(Ci-C6alkyl)amino, Ci-Cealkoxycarbonyl, Ci-Cehaloalkoxycarbonyl, — C(0)NH2, Ci-Cealkylaminocarbonyl, Ci-Cehaloalkylaminocarbonyl, di(Ci-C6alkyl)aminocarbonyl, — C(S)NH2, — S(O)2NH2, Ci-Cealkylaminosulfonyl, di(Ci- C6alkyl)aminosulfonyl, phenyl or phenyl arbitrarily substituted with halogen atom, when pl, p2, p3 or p4 is an integer of 2 or more, each Z may be identical with or different from each other, further, when two Zs are adjacent, the adjacent two Zs may form 5-membered or 6-membered ring together with carbon atoms to which the two Zs are bonded by forming — CH2CH2CH2 —,Attorney Docket No. 10620-164W02

[0132] NCSURef.: 2025-138-04

[0133] — CH2CH2O—, — CH2OCH2—, — OCH2O—, — CH2CH2S—, — CH2SCH2—, — CH2CH2CH2CH2—, — CH2CH2CH2O—, — CH2CH2OCH2—, — CH2OCH2O—, — OCH2CH2O—, — CH2CH2CH2S—, — OCH2CH2S— or — CH=CH— CH=CH—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, cyano, nitro, Ci-C4alkyl, C1-C4haloalkyl, Ci-C4alkoxy or Ci-C4alkylthio;

[0134] E-l to E-49 are saturated heterocyclic rings of the following formulae, respectively

[0135]

[0136] Attorney Docket No. 10620-164W02

[0137] NCSURef.: 2025-138-04

[0138]

[0139] Attorney Docket No. 10620-164W02

[0140] NCSURef.: 2025-138-04

[0141] D-R4is halogen atom, cyano, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, — OH, — O(D-R5), — SH, — S(O)r(D-R5), — N(D-R10)(D-R9), — N(D-R10)CHO, — N(D-R10)C(O)(D-R9), — N(D-R10)C(O)O(D-R9), — N(D-R10)C(O)S(D-R9), — N(D-R10)C(S)O(D-R9), — N(D-R10)C(S)S(D-R9), — N(D-R10)S(O)2(D-R9), — C(O)O(D-R9), — C(O)N(D-R10) (D-R9), — Si(D-R13)(D-R14) (D-R12), phenyl, phenyl substituted with (Z)PiD-l to D-65, or E-l to E-45;

[0142] D-R5is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R24, Cs-Cscycloalkyl, C3-Cscycloalkyl arbitrarily substituted with D-R24, C2-Cealkenyl, C2-Cealkenyl arbitrarily substituted with D-R24, Cs-Cscycloalkenyl, Cs-Cshalocycloalkenyl, Cs-Cealkynyl, Cs-Cealkynyl arbitrarily substituted with D-R24, Ci-Cealkylcarbonyl, Ci-Cealkoxy carbonyl, phenyl, phenyl substituted with (Z)Pi, D-l to D-65, or E-l to E-45;

[0143] D-R6is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R24, Cs-Cecycloalkyl, C3-Cshalocycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, — OH, Ci-Cealkylcarbonyloxy, Ci-Cealkylthio, Ci-Cehaloalkylthio, phenylthio, phenylthio substituted with (Z)Pi, — SN(D-R18) (D-R17), — S(O)2(D-R9), — S(O)2N(D-R10) (D-R9), — CHO, — C(O)(D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(O)NH(D-R10), — C(O)N(D-R10)(D-R9), — C(S)O(D-R9), — C(S)S(D-R9), — C(S)NH(D-R10), — C(S)N(D-R10) (D-R9), — C(O)C(O) (D-R9), — C(O)C(O)O(D-R9), — P(O)(O-D-R21)2or — P(S)(O-D-R21)2;

[0144] D-R7is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cscycloalkyl Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, C1-C4 alkylthio Ci-C4alkyl, Cs-Cscycloalkyl, Cs-Cealkenyl, CsCehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, — CHO, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl or Ci-Cealkoxy carbonyl, or D-R7together with D-R6may form 3- to 5-membered ring with the bonding nitrogen atom by forming C2-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, oxo or thioxo;

[0145] D-R8is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cealkenyl, phenyl or phenyl substituted with (z)Pi;

[0146] D-R9is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R24, Cs-Cscycloalkyl, C3-Cshalocycloalkyl, C2-Cealkenyl, C2-C6haloalkenyl, C2-Cealkynyl, C2-C6haloalkynyl, phenyl, phenyl substituted with (Z)PiD-l to D-65, or E-l to E-45;

[0147] D-R10is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-Cealkoxy Ci-C4alkyl, Ci-Cealkylthio Ci-C4alkyl, cyano Ci-Cealkyl, Cs-Cealkenyl or C3-Cealkynyl, D-R10together with D-R9may form a 3- to 7-membered ring with the atom bonding them by forming a C2-Cealkylene chain, in this case, the alkylene chain may contain one oxygenAttorney Docket No. 10620-164W02

[0148] NCSURef.: 2025-138-04

[0149] atom or sulfur atom, or D-R10together with D-R9may form a 3- to 5-membered ring with the atom bonding them by forming a C2-C4alkylene chain, in this case, the alkylene chain may contain one nitrogen atom, and either ring may be arbitrarily substituted with halogen atom, Ci-Cealkyl or Ci-Cehaloalkoxy, formyl, Ci-Cealkylcarbonyl or Ci-Cealkoxycarbonyl;

[0150] D-R11is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, phenyl or phenyl that may be substituted with (Z)Pi, D-R11together with D-R9may form 5- to 7-membered ring with the atom bonding them by forming C2-C4alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, or D-R11together with D-R9may form a 5-membered ring with the atom bonding them by forming C2-alkylene chain, in this case, the alkylene chain may contain one nitrogen, and either ring may be arbitrarily substituted with halogen atom, Ci-Cealkyl or Ci-Cehaloalkyl;

[0151] D-R12is Ci-Cealkyl, Ci-Cehaloalkyl, phenyl or phenyl substituted with (Z)Pi;

[0152] D-R13and D-R14independently of each other are Ci-Cealkyl or Ci-Cehaloalkyl;

[0153] R15is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-Cealkoxycarbonyl Ci-C4alkyl, Ci-Cehaloalkoxycarbonyl Ci-C4alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, Ci-Cealkoxy, Ci-Cealkoxycarbonyl, Ci-Cehaloalkoxy carbonyl, phenyl or phenyl substituted with (Z)Pi, further, in case where Z is present in an adjacent position of R15, the adjacent R15and Z may form 6-membered ring together with the atom bonding them by forming — CH2CH2CH2CH2 — or — CH=CH — CH=CH —, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, Ci-C4alkyl or Ci-C4haloalkyl;

[0154] D-R16is halogen atom, cyano, nitro, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, hydroxy C3-Cecycloalkyl, Ci-C4alkoxy Cs-Cecycloalkyl, Cs-Cecycloalkenyl, — O25, — N(D-R26) (D-R25), — SH, — S(O)r(D-R27), — SO2OH, — SO2NH(D-R29), — SO2N(D-R29) (D-R28), — CHO, — C(O) (D-R28), — C(O)OH, — C(O)O(D-R28), — C(O)S(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(O)N(D-R29)O(D-R28), — C(O)N(D-R29)N(D-R28a) (D-R28), — C(S)O(D-R28), — C(S)S(D-R28), — C(S)NH(D-R29), — C(S)N(D-R29) (D-R28), — C(O)C(O)O(D-R28), — C(D-R31)=NOH, — C(D-R31)=NO(D-R30), — C(=N-D-R31)O(D-R30), — C(=N-D-R31)S(D-R30), — C(=N-D-R31)N(D-R29) (D-R30), — C(=NO-D-R31)NH(D-R29), — C(=NO-D-R31)N(D-R29) (D-R30), — Si(D-R13)(D-R14) (D-R12), — P(O)(O-D-R21)2, — P(S)(O-D-R21)2, — P(phenyl)2, — P(O)(phenyl)2, phenyl, phenyl substituted with (Z)Pi, naphthyl D-l to D-65, E-l to E-45, or M-l to M-ll;Attomey Docket No. 10620-164W02

[0155] NCSU Ref.: 2025-138-04

[0156] M-l to M-ll are partially saturated heterocyclic rings of the following formulae, respectively

[0157]

[0158] D-R17is Ci- alkyl, Ci-C haloalkyl, Ci- alkoxy Ci- alkyl, cyano Ci-i2alkyl, Ci-nalkoxy carbonyl Ci- alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, C3-C alkenyl, C3-Ci2haloalkenyl, Cs-C alkynyl, Cs-C haloalkynyl, Ci-C alkylcarbonyl, Ci-Attorney Docket No. 10620-164W02

[0159] NCSURef.: 2025-138-04

[0160] Ci2alkoxy carbonyl, — C(O)ON=C(CH3)SCH3, — C(O)ON=C(SCH3)C(O)N(CH3)2, phenyl or phenyl substituted with (Z)Pi;

[0161] D-R18is Ci-C alkyl, Ci-Ci2haloalkyl, Ci- alkoxy Ci-i2alkyl, cyano Ci- alkyl, Ci-C alkoxy carbonyl Ci- alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, C3-C alkenyl, C3-i2haloalkenyl, C3-Ci2alkynyl, C3-Ci2haloalkynyl, phenyl or phenyl substituted with (Z)Pi, or D-R18together with D-R17may form a 5-membered ring with the nitrogen atom bonding them by forming C4alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, and may be arbitrarily substituted with Ci-C4alkyl or Ci-C4alkoxy;

[0162] D-R19is hydrogen atom, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R16, C3-Cscycloalkyl, -Cshalocycloalkyl, C3-Cealkenyl, -Cehaloalkenyl, C3-Cealkynyl, C3-Cehaloalkynyl, — CHO, — C(O)(D-R28), — C(O)O(D-R28), — C(O)S(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(S)O(D-R28), — C(S)S(D-R28), — C(S)NH(D-R29), — C(S)N(D-R29) (D-R28), — S(O)2(D-R28), — S(O)2NH(D-R29), — S(O)2N(D-R29) (D-R28), — P(O)(O-D-R21)2, — P(S)(O-D-R21)2, phenyl, phenyl substituted with (Z)Pi, D-1 to D-65, or E-1 to E-49;

[0163] D-R19ais hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Ci-C4alkylsulfonyl Ci-C4alkyl, Ci-C4alkoxycarbonyl Ci-C4alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, C3-Cecycloalkyl, phenyl C2-C4alkenyl, di(Ci-C6alkyl)amino, phenyl, or phenyl substituted with (Z)PiD-l to D-65, or E-l to E-45;

[0164] D-R19bis hydrogen atom, Ci-Cealkyl, Ci-Cealkoxy, Ci-Cealkylthio or di(Ci-C6alkyl)amino, or D-R19atogether with D-R19bmay form a 4- to 6-membered ring with the carbon atom bonding them by forming C3-Csalkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, or D-R19atogether with D-R19bmay form a 4- to 5-membered ring with the carbon atom bonding them by forming C3-C4alkylene chain, in this case, the alkylene chain may contain one nitrogen, and either ring may be arbitrarily substituted with halogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, formyl, Ci-Cealkylcarbonyl or Ci-Cealkoxycarbonyl;

[0165] D-R20is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4haloalkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Ci-C4haloalkylthio Ci-C4alkyl, Ci-C4alkylsulfonyl Ci-C4alkyl, Ci-C4haloalkylsulfonyl Ci-C4alkyl, cyano Ci-Cealkyl, Ci-C4alkoxycarbonyl Ci-C4alkyl, phenyl Ci-C4alkyl, C2-Cealkenyl, C2-Cehaloalkenyl, C3-Cealkynyl, -Cehaloalkynyl, —CHO, — C(O) (D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(S)O(D-R9), — C(S)S(D-R9), Ci-Cealkylsulfonyl or Ci-Cehaloalkylsulfonyl, or D-R20together with D-R19may form a 5-membered ring with the nitrogen atom bonding them by forming C4alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, andAttorney Docket No. 10620-164W02

[0166] NCSURef.: 2025-138-04

[0167] may be arbitrarily substituted with Ci-Cealkyl, Ci-Cealkoxy Ci-Cealkyl, — CHO, Ci-Cealkylcarbonyl or Ci-Cealkoxycarbonyl;

[0168] D-R21is Ci-Cealkyl or Ci-Cehaloalkyl;

[0169] D-R22is halogen atom, cyano, Ci-Cealkyl, Ci-Cehaloalkyl, hydroxy Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkoxy carbonyl Ci-C4alkyl, Ci-Cealkoxy, Ci-Cealkylthio, Ci-Cealkylamino, di(Ci-C4alkyl)amino, Ci-Cealkoxy carbonyl, phenyl or phenyl substituted with (Z)Pi, when ql, q2, q3 or q4 is an integer of 2 or more, each D-R22may be identical with or different from each other, further in case where two D-R22s are present on the same carbon atom, the two D-R22S together may form oxo, thioxo, imino, Ci-Cealkylimino, Ci-Cealkoxyimino or Ci-Cealkylidene;

[0170] R23is hydrogen atom, Ci-Cealkyl, Ci-Cealkyl substituted with D-R32, Cs-Cecycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, — OH, benzyloxy, — CHO, — C(O) (D-R33), — C(O)O(D-R33), — C(O)S(D-R33), — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), — C(S)NH(D-R34), — C(S)N(D-R34) (D-R33), — S(O)2(D-R33), — P(O)(O-D-R21)2, — P(S)(O-D-R21)2, phenyl, phenyl substituted with (Z)Pior D-5;

[0171] D-R24is halogen atom, cyano, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, Ci-Cealkoxy, Ci-Cehaloalkoxy, Ci-Cealkylthio, Ci-Cehaloalkylthio, Ci-Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl, Ci-Cealkylamino, di(Ci-C6alkyl)amino, — CHO, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci-Cealkoxycarbonyl, Ci-Cehaloalkoxycarbonyl, Ci-Cealkylaminocarbonyl, di(Ci-C6alkyl)aminocarbonyl, phenyl or phenyl substituted with (Z)PiD-l to D-65, or E-l to E-49;

[0172] D-R25is hydrogen atom, Ci-Csalkyl, Ci-Csalkyl arbitrarily substituted with D-R32, C3-Cscycloalkyl, Cs-Cscycloalkyl arbitrarily substituted with D-R32, Cs-Csalkenyl, Cs-Csalkenyl arbitrarily substituted with D-R32, Cs-Csalkynyl. Cs-Csalkynyl arbitrarily substituted with D-R32, —CHO, — C(O)(D-R33), — C(O)O(D-R33), — C(O)S(D-R33), — C(O)NH(D-R34), C(O)N(D-R34) (D-R33), — C(O)C(O) (D-R33), — C(O)C(O)O(D-R33), — C(S) (D-R33), — C(S)O(D-R33), — C(S)S(D-R33), — C(S)NH(D-R34), — C(S)N(D-R34) (D-R33), — S(O)2(D-R33), — S(O)2N(D-R34) (D-R33), — Si(D-R13)(D-R14) (D-R12), — P(O)(O-D-R21)2, — P(S)(O-D-R21)2, phenyl, phenyl substituted with (Z)Pi, D-l to D-65, or E-l to E-49;

[0173] D-R26is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Cs-Cecycloalkyl, Cs-Cealkenyl, Cs-Cealkynyl, Ci-Cealkoxy, phenyl or phenyl substituted with (Z)Pi, or D-R26together with D-R25may form 3- to 5-membered ring with the nitrogen atom bonding them by forming C2-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be substituted withAttorney Docket No. 10620-164W02

[0174] NCSURef.: 2025-138-04

[0175] halogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-Cealkoxy, phenyl, phenyl substituted with (Z)Pi, oxo or thioxo;

[0176] D-R27is Ci-Csalkyl, Ci-Csalkyl arbitrarily substituted with D-R32, Cs-Cscycloalkyl, Cs-scycloalkyl arbitrarily substituted with D-R32, Cs-Csalkenyl. Cs-Csalkenyl arbitrarily substituted with D-R32, Cs-Csalkynyl, Cs-Csalkynyl arbitrarily substituted with D-R32, — SH, Ci-Cealkylthio, Ci-Cehaloalkylthio, phenylthio, phenylthio substituted with (Z)Pi, — CHO, — C(O) (D-R33), — C(O)O(D-R33), — C(O)S(D-R33), — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), — C(O)C(O) (D-R33), — C(O)C(O)O(D-R33), — C(S) (D-R33), — C(S)O(D-R33), — C(S)S(D-R33), — C(S)NH(D-R34), — C(S)N(D-R34) (D-R33), — P(O)(O-D-R21)2, — P(S)(O-D-R21)2, phenyl, phenyl substituted with (Z)Pi, D-l to D-65, or E-l to E-49;

[0177] D-R28is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R32, Cs-Cscycloalkyl, Cs-Cscycloalkyl arbitrarily substituted with D-R32, C2-Cealkenyl Cs-Cscycloalkyl, C2-C6haloalkenyl C3-C8cycloalkyl, C2-Csalkenyl, C2-Csalkenyl arbitrarily substituted with D-R32, C2-Csalkynyl, C2-Csalkynyl arbitrarily substituted with D-R32, phenyl or phenyl substituted with (Z)PiD-l to D-65, or E-l to E-49;

[0178] D-R28ais hydrogen atom or Ci-Cealkyl;

[0179] D-R29is hydrogen atom, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R32, C3-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, phenyl or phenyl substituted with (Z)Pi, or D-R29together with D-R28may form 3- to 5-membered ring with the nitrogen atom bonding them by forming C2-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, Ci-Cealkyl, Ci-Cealkoxy, formyl, Ci-Cealkylcarbonyl, Ci-Cealkoxycarbonyl, phenyl or phenyl substituted with (Z)Pi;

[0180] D-R30is Ci-Csalkyl, Ci-Csalkyl arbitrarily substituted with D-R32, Cs-Cscycloalkyl, C3-Csalkenyl, Cs-Csalkenyl arbitrarily substituted with D-R32, Cs-Csalkynyl, Cs-Csalkynyl arbitrarily substituted with D-R32;

[0181] D-R31is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-Cealkoxy Ci-C4alkyl, Ci-Cehaloalkoxy Ci-C4alkyl, Ci-Cealkylthio Ci-C4alkyl, Ci-Cehaloalkylthio Ci-C4alkyl, Ci-Cealkylsulfonyl Ci-C4alkyl, Ci-Cehaloalkylsulfonyl Ci-C4alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Cecycloalkyl, phenyl or phenyl substituted with (Z)Pi, or D-R31together with D-R30may form 5- to 7-membered ring with the atom bonding them by forming C2-C4alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, or D-R31together with D-R30may form a 5-membered ring with the atom bonding them by forming C2alkylene chain, in this case, the alkylene chain may containAttorney Docket No. 10620-164W02

[0182] NCSURef.: 2025-138-04

[0183] one nitrogen, and either ring may be arbitrarily substituted with halogen atom, Ci-Cealkyl or Ci-Cehaloalkyl;

[0184] D-R32is halogen atom, cyano, nitro, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, — OH, — O(D-R33), — OC(O) (D-R33), — OC(O)O(D-R33), — OC(O)NH(D-R34), — OC(O)N(D-R34) (D-R33), — OC(S)NH(D-R34), — OC(S)N(D-R34) (D-R33), — SH, — S(O)r(D-R33), — SC(O) (D-R33), — SC(O)O(D-R33), — SC(O)NH(D-R34), — SC(O)N(D-R34) (D-R33), — SC(S)NH(D-R34), — SC(S)N(D-R34) (D-R33), — NH(D-R34), — N(D-R34) (D-R33), — N(D-R34)CHO, — N(D-R34)C(O) (D-R33), — N(D-R34)C(O)O(D-R33), — N(D-R34)C(O)NH(D-R34), — N(D-R34)C(O)N(D-R34) (D-R33), — N(D-R34)C(S)NH(D-R34), — N(D-R34)C(S)N(D-R34) (D-R33), — CHO, — C(O) (D-R33), — C(O)O(D-R33), — C(O)S(D-R33), — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), — C(O)C(O)O(D-R33), — Si(D-R13)(D-R14) (D-R12), — P(O)(O-D-R21)2, — P(S)(O-D-R21)2, — P(phenyl)2, — P(O)(phenyl)2, phenyl, phenyl substituted with (Z)Pi, D-l to D-65, or E-l to E49;

[0185] D-R33is Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkyl arbitrarily substituted with D-R35, Cs-Cecycloalkyl, Cs-Cehalocycloalkyl, C2-Cealkenyl Cs-Cscycloalkyl, C2-Cehaloalkenyl C3-Cscycloalkyl, C2-Csalkenyl, C2-Cshaloalkenyl, Cs-Cscycloalkenyl, Cs-Cshalocycloalkenyl, C2-Csalkynyl. C -Cshaloalkynyl, phenyl or phenyl substituted with (Z)Pi, D-l to D-65, or E-l to E-49;

[0186] D-R34is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cscycloalkyl, Cs-Cealkenyl, C3-Cealkynyl, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci-Cealkoxycarbonyl, Ci-Cehaloalkoxycarbonyl, phenoxycarbonyl, phenoxy carbonyl substituted with (Z)Pi, phenylcarbonyl, phenylcarbonyl substituted with (Z)Pi, Ci-Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl, phenyl, phenyl substituted with (Z)Pi, D-l to D-65, or D-R34together with D-R33may form 3- to 5 -membered ring with the nitrogen atom bonding them by forming C2-Csalkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, Ci-Cealkyl, Ci-Cealkoxy, formyl, Ci-Cealkylcarbonyl, Ci-Cealkoxycarbonyl, phenyl or phenyl substituted with (Z)Pi;

[0187] D-R35is cyano, Cs-Cecycloalkyl, Cs-Cehalocylcoalkyl, E-l to E-49, Ci-C4alkoxy, Ci-C4haloalkoxy, Ci-C4alkylthio, Ci-C4haloalkylthio, Ci-C4alkylsulfonyl, Ci-C4haloalkylsulfonyl, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci-Cealkoxycarbonyl, di(Ci-C6alkyl)aminocarbonyl, tri(Ci-C6alkyl)silyl, phenyl, phenyl substituted with (Z)Pi, or D-l to D-65;

[0188] m is an integer of 0 to 5;

[0189] n is an integer of 0 to 4;

[0190] pl is an integer of 1 to 5;Attorney Docket No. 10620-164W02

[0191] NCSURef.: 2025-138-04

[0192] p2 is an integer of 0 to 4;

[0193] p3 is an integer of 0 to 3;

[0194] p4 is an integer of 0 to 2;

[0195] p5 is an integer of 0 or 1;

[0196] ql is an integer of 0 to 3;

[0197] q2 is an integer of 0 to 5;

[0198] q3 is an integer of 0 to 7;

[0199] q4 is an integer of 0 to 9;

[0200] r is an integer of 0 to 2; and

[0201] t is an integer of 0 or 1.

[0202] In some embodiments, D-G is a benzene ring;

[0203] D-X is halogen atom, cyano, nitro, — SFs, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-(D-R4), Cs-Cscycloalkyl, Cs-Cscycloalkyl arbitrarily substituted with D-R4, C2-Cealkenyl, C2-Cealkenyl arbitrarily substituted with D-R4, C2-Cealkynyl, C2-Cealkynyl arbitrarily substituted with D-R4, —OH, — 0(D-R5), — OSO2(D-R5), — S(O)r(D-R5), — C(O)O(D-R9), — C(O)S(D-R9), — C(O)NH(D-R10), — C(O)N(D-R10) (D-R9), — C(S)O(D-R9), — C(S)S(D-R9), — C(S)NH(D-R10), — C(S)N(D-R10) (D-R9), — CH=N0(D-R11), — C(D-R9)=NO(D-R11), — S(O)2NH(D-R10), — S(O)2N(D-R10) (D-R9), — Si(D-R13)(D-R14) (D-R12), phenyl, phenyl substituted with (Z)Pi, D-l to D-46, E-l to E-28, E-32 to E-38 or E-43 to E-45, when m is an integer of 2 or more, each D-X may be identical with or different from each other, further, when two D-Xs are adjacent, the adjacent two D-Xs may form 5-membered or 6-membered ring together with carbon atoms to which the two D-Xs are bonded by forming — CH2CH2CH2 —, — CH2CH2O—, — CH2OCH2—, — OCH2O—, — CH2CH2S—, — CH2SCH2—, — CH2CH2CH2CH2—, — CH2CH2CH2O—, — CH2CH2OCH2—, — CH2OCH2O—, — OCH2CH2O —, — OCH2CH2S — or — CH=CHCH=CH —, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, Ci-C4alkyl or Ci-C4haloalkyl,

[0204] D-Y is halogen atom, cyano, nitro, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R4, — O(D-R5), — OSO2(D-R5), — S(O)r(D-R5), — NH(D-R7), — N(D-R7) (D-R6), — N=CHO(D-R8), — N=C(D-R9)O(D-R8), — C(O)NH(D-R10), — C(O)N(D-R10) (D-R9), — C(S)NH(D-R10), — C(S)N(D-R10) (D-R9), phenyl, phenyl substituted with (Z)Pi, D-l to D-24, D-30 to D-38 or D-43 to D-46, when n is an integer of 2 or more, each D-Y may be identical with or different from each other,Attorney Docket No. 10620-164W02

[0205] NCSURef.: 2025-138-04

[0206] further, when two D-Ys are adjacent, the adjacent two D-Ys may form 5 -membered or 6-membered ring together with carbon atoms to which the two D-Ys are bonded by forming — CH2CH2CH2—, — CH2CH2O—, — CH2OCH2—, — OCH2O—, — CH2CH2CH2CH2—, — CH2CH2CH2O—, — CH2CH2OCH2—, — CH2OCH2O—, — OCH2CH2O—, — OCH=N— or — SCH=N —, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, Ci-C4alkyl or C1-C4haloalkyl,

[0207] D-R1is Ci-Csalkyl, Ci-Csalkyl arbitrarily substituted with D-R16, Cs-Cscycloalkyl, C3-Cshalocycloalkyl, Cs-Csalkenyl, Cs-Cshaloalkenyl, phenyl Cs-Cealkenyl, phenyl Cs-Cealkenyl substituted with (Z)Pi, Cs-Csalkynyl, Cs-Cshaloalkynyl, phenyl Cs-Cealkynyl, phenyl C3-Cealkynyl substituted with (Z)Pi, Ci-Csalkoxy, — N(D-R20) (D-R19), — N=CH(D-R19b), — N=C(D-R19b) (D-R19a), — C(O)N(D-R10) (D-R9), — C(S)N(D-R10) (D-R9), — C(=N-D-R11)O(D-R9), — C(=N-D-R11)S(D-R9), — C(=N-D-R11)N(D-R10) (D-R9), phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-6 to D-18, D-21 to D-23, D-26 to D-40, D-42, D-45 to D-46, E-4 to E-9, E-23 to E-28, E-34 or E-45,

[0208] D-R2is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4haloalkoxy Ci-C4alkyl, benzyloxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Ci-C4haloalkylthio Ci-C4alkyl, Ci-C4alkylsulfonyl Ci-C4alkyl, Ci-C4haloalkylsulfonyl Ci-C4alkyl, phenylthio Ci-c 4alkyl, phenylthio Ci-C4alkyl substituted with (Z)Pi, cyano Ci-Cealkyl, nitro Ci-Cealkyl, Ci-C4alkylcarbonyl Ci-C4alkyl, Ci-C4alkoxy carbonyl Ci-C4alkyl, C3-Cecycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, — S(D-R9), — S(O)2(D-R9), — SN(D-R18) (D-R17), —OH, — O(D-R19), — NH(D-R20), — N(D-R20) (D-R19), — N=CH(D-R19b), — N=C(D-R19b) (D-R19a), — C(O) (D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(S)O(D-R9) or — C(S)S(D-R9);

[0209] or D-R1and D-R2together form =C(D-R2a) (D-Rla), and further D-R1and D-R2together may form 3- to 5-membered ring together with the nitrogen atom bonding them by forming C2to C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with Ci-Cealkyl, formyl, Ci-Cealkylcarbonyl or Ci-Cealkoxy carbonyl,

[0210] D-R1aand D-R2atogether may form 5- or 6-membered ring together with the carbon atom bonding them by forming C4or C5alkylene chain or C4or C5alkenylene chain, in this case, the alkylene chain and the alkenylene chain may contain one to three oxygen atoms or sulfur atoms, or D-Rlaand D-R2atogether may form a 5-membered ring together with the carbon atom bonding them by forming C4 alkylene chain or C4 alkenylene chain, in this case, the alkylene chain andAttorney Docket No. 10620-164W02

[0211] NCSURef.: 2025-138-04

[0212] the alkenylene chain may contain one to three nitrogen atoms, and either ring may be arbitrarily substituted with halogen atom or Ci-Cealkyl,

[0213] D-R3is cyano, Ci-Cealkyl arbitrarily substituted with D-R4, Cs-Cscycloalkyl, C3-Cshalocycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, — O(D-R5), — S(O)r(D-R5), — N(D-R10) (D-R9), — C(O)O(D-R9), C(O)S(D-R9), — C(O)NH(D-R10), — C(O)N(D-R10) (D-R9), — C(S)O(D-R9), — C(S)S(D-R9), — C(S)NH(D-R10), — C(S)N(D-R10) (D-R9), — CH=NO(D-R11), — C(D-R9)=NO(D-R11), — Si(D-R13)(D-R14) (D-R12), phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-8 to D-13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 to D-46 or E-4 to E-7, E-23 to E-27 or E-28;

[0214] D-R4is halogen atom, cyano, Cs-Cecycloalkyl, Cs-Cehalocycloalkyl, — OH, — O(D-R5), — S(O)r(D-R5), — N(D-R10) (D-R9), — N(D-R10)C(O) (D-R9), — N(D-R10)C(O)O(D-R9), — N(D-R10)C(O)S(D-R9), — N(D-R10)C(S)O(D-R9), — N(D-R10)C(S)S(D-R9), — N(D-R10)S(O)2(D-R9), — Si(D-R13)(D-R14) (D-R12), phenyl, phenyl substituted with (Z)Pi, D-l to D-5, D-8 to D-38, D-41, D-43 or D-44;

[0215] D-R5is Ci-Cealkyl, Ci-Cehaloalkyl, Ci-Cshaloalkoxy Ci-Cshaloalkyl, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, C2-Cealkenyl, C2-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-7, D-9, D-15 to D-23, D-30 to D-35, E-3 to E-9, E-23 to E-27 or E-28

[0216] D-R6is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, — S(O)2R9, — CHO, — C(O) (D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(S)O(D-R9), or — C(S)S(D-R9);

[0217] D-R7is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cealkenyl or Cs-Cealkynyl;

[0218] D-R8is Ci-Cealkyl;

[0219] D-R9is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-Cealkoxy Ci-C4alkyl, Ci-Cealkylthio Ci-C4alkyl, cyano Ci-Cealkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-6 to D-35 or D-38;

[0220] D-R10is hydrogen atom or Ci-Cealkyl, or D-R10together with D-R9may form a 5-membered ring with the nitrogen atom bonding them by forming C4alkylene chain, in this case, the alkylene chain may contain oxygen atom or sulfur atom;

[0221] D-R11is Ci-Cealkyl, Ci-Cehaloalkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, phenyl or phenyl substituted with (Z)Pi, or D-R11together with D-R9may form 5- orAttorney Docket No. 10620-164W02

[0222] NCSURef.: 2025-138-04

[0223] 6-membered ring with the atom bonding them by forming C2-C3alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with Ci-Cealkyl;

[0224] D-R12is Ci-Cealkyl, phenyl or phenyl substituted with (Z)Pi;

[0225] D-R13and D-R14independently of each other are Ci-Cealkyl;

[0226] D-R15is Ci-Cealkyl, Ci-Cehaloalkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, phenyl or phenyl substituted with (Z)Pi;

[0227] D-R16is halogen atom, cyano, Cs-Cecycloalkyl, Cs-Cehalocycloalkyl, — O(D-R25), — N(D-R26) (D-R25), — SH, — S(O)r(D-R27), — SO2NH(D-R29), — SO2N(D-R29) (D-R28), — CHO, — C(O) (D-R28), — C(C)O(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(O)N(D-R29)O(D-R28), — C(S)NH(D-R29), — C(S)N(D-R29) (D-R28), — C(D-R31)=NOH, — C(D-R31)=NO(D-R30), — C(=N-D-R31)O(D-R30), — C(=N-D-R31)S(D-R30), — C(=N-D-R31)N(D-R29) (D-R30), — C(=NO-D-R31)NH(D-R29), — C(=NO-D-R31)N(D-R29) (D-R30), — Si(D-R13)(D-R14) (D-R12) phenyl, phenyl substituted with (Z)Pi, D-l to D-46, E-l to E-28, E-32 to E-38, E-43 to E-45 or M-l to M-ll;

[0228] D-R17is Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-Cealkoxy carbonyl Ci-C4alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pior Ci-Cealkoxy carbonyl;

[0229] D-R18is Ci-Cealkyl, phenyl Ci-C4alkyl or phenyl Ci-C4alkyl substituted with (Z)Pi, or D-R18together with D-R17may form a 5-membered ring with the nitrogen atom bonding them by forming C4alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, and may be arbitrarily substituted with methyl or methoxy;

[0230] D-R19is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R16, Cs-Cecycloalkyl, C3-Cehalocycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, — CHO, — C(O) (D-R28), — C(O)O(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(S)NH(D-R29), — C(S)N(D-R29) (D-R28), — S(O)2(D-R28), — S(O)2NH(D-R29), — S(O)2N(D-R29) (D-R28), phenyl, phenyl substituted with (Z)Pi, D-l to D-13, D-15 to D-25, D-30 to D-37, D-39, D-40, D-42, D-45 to D-46, E-5, E-7, E-9, E-24, E-25, E-27 or E-28;

[0231] D-R19ais Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl, phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-8 to D-10, D-15 to D-23, E-4 to E-7, E-23 to E-27 or E-28;

[0232] D-R19bis hydrogen atom or Ci-Cealkyl, or D-R19atogether with D-R19bmay form 5- or 6-membered ring with the carbon atom bonding them by forming C4 or Csalkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom;

[0233] D-R20is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, cyano Ci-Cealkyl, Ci-C4alkoxycarbonyl Ci-C4alkyl, C2-Cealkenyl, C3-Attorney Docket No. 10620-164W02

[0234] NCSURef.: 2025-138-04

[0235] Cealkynyl, — CHO, — C(O) (D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(S)O(D-R9), — C(S)S(D-R9) or Ci-Cealkylsulfonyl;

[0236] D-R22is halogen atom, cyano, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-Cealkoxy, Ci-Cealkoxycarbonyl, — C(O)NH2 or — C(S)N2, when ql, q2, q3 or q4 is an integer of 2 or more, each D-R22may be identical with or different from each other, further in case where two D-R22s are present on the same carbon atom, the two D-R22s together may form oxo, thioxo, imino, Ci-Cealkylimino, Ci-Cealkoxyimino or Ci-Cealkylidene;

[0237] R23is hydrogen atom, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R32, C3-Cecycloalkyl, Cs-Cealkenyl, Cs-Cealkynyl, — OH, benzyloxy, — CHO, — C(O) (D-R33), — C(O)O(D-R33), — C(O)S(D-R33), — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), — S(O)2(D-R33), phenyl, phenyl substituted with (Z)Pior D-5;

[0238] D-R25is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, cyano Ci-Cealkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, C3-C6alkenyl, Cs-Cealkynyl, —CHO, — C(O) (D-R33), — C(O)O(D-R33), — C(O)S(D-R33), — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), — C(S) (D-R33), — C(S)O(D-R33), — C(S)S(D-R33), — C(S)NH(D-R34), — C(S)N(D-R34) (D-R33), — S(O)2(D-R33), — S(O)2N(D-R34) (D-R33), di(Ci-C6alkyl)phosphoryl, di(Ci-C6alkyl)thiophosphoryl, tri(Ci-C4alkyl)silyl, phenyl or phenyl substituted with (Z)Pi;

[0239] D-R26is hydrogen atom, Ci-Cealkyl, Cs-Cealkenyl, Cs-Cealkynyl or Ci-Cealkoxy, or D-R26together with D-R25may form 4- to 5 -membered ring with the nitrogen atom bonding them by forming C3-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may substituted with Ci-Cealkyl, oxo or thioxo;

[0240] D-R27is Ci-Cealkyl, Ci-Cehaloalkyl, hydroxy Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Ci-C4alkylcarbonyl Ci-C4alkyl, Ci-C4alkoxy carbonyl Ci-C4alkyl, di(Ci-C4alkyl)aminocarbonyl Ci-C4alkyl, tri(Ci-C4alkyl)silyl Ci-C4alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Cealkenyl, Cs-Cealkynyl, Ci-Cealkylcarbonyl, Ci-Cealkylthio, phenylthio, phenylthio substituted with (Z)Pi, — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), — C(S)NH(D-R34), — C(S)N(D-R34) (D-R33), phenyl, phenyl substituted with (Z)Pi, D-21 or D-35;

[0241] D-R28is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R32, Cs-Cecycloalkyl, C3-Cehalocycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, phenyl, phenyl substituted with (Z)Pi, D-l to D-46 or E-l to E-28, E-32 to E-38, or E-43 to E-45;

[0242] D-R29is hydrogen atom, Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, cyano Ci-Cealkyl, Cs-Cealkenyl or Cs-Cealkynyl, or D-R29together with D-R28may form 3- to 5-Attorney Docket No. 10620-164W02

[0243] NCSURef.: 2025-138-04

[0244] membered ring with the nitrogen atom bonding them by forming C2-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom;

[0245] D-R30is Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Cs-Cecycloalkyl Ci-C4alkyl, tri(Ci-C6alkyl)silyl Ci-C4alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Csalkenyl, Cs-Cshaloalkenyl, Cs-Csalkynyl or Cs-Cshaloalkynyl;

[0246] D-R31is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl or Cs-Cecycloalkyl, or D-R31together with D-R30may form 5- or 6-membered ring with the atom bonding them by forming C2-C3alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with Ci-Cealkyl;

[0247] D-R32is halogen atom, cyano, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, — O(D-R33), — OC(O) (D-R33), — OC(O)NH(D-R33), — OC(O)N(D-R34) (D-R33), — S(O)r(D-R33), — SC(O) (D-R33), — SC(O)NH(D-R33), — SC(O)N(D-R34) (D-R33), — N(D-R34)CHO, — N(D-R34)C(O) (D-R33), — N(D-R34)C(O)O(D-R33), — C(O)O(D-R33), — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), phenyl, phenyl substituted with (Z)Pi, D-l to D-46 or E-l to E-28, E-32 to E-38, or E-43 to E-45;

[0248] D-R33is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4haloalkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Ci-C4haloalkylthio Ci-C4alkyl, Ci-C4alkylsulfonyl Ci-C4alkyl, Ci-C4haloalkylsulfonyl Ci-C4alkyl, cyano Ci-Cealkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Cecycloalkyl, Cs-Cehalocycloalkyl, C3-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-8 to D-13, D-15 to D-18, D-21, D-29 to D-37, E-5, E-7, E-9, E-24, E-25, E-27, E-28 or E-34;

[0249] D-R34is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cealkenyl or Cs-Cealkynyl, or D-R34together with D-R33may form 3- to 5 -membered ring with the nitrogen atom bonding them by forming C2-Csalkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom.

[0250] In some embodiments, D-G is a benzene ring

[0251] D-X is halogen atom, cyano, nitro, — SFs, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R4, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, C2-Cealkenyl, C2-Cehaloalkenyl, C2-Cealkynyl, C2-Cehaloalkynyl, — O(D-R5), — OSO2(D-R5), — S(O)r(D-R5), — C(O)O(D-R9), — C(O)S(D-R9), — C(S)O(D-R9), — C(S)S(D-R9), — C(S)NH(D-R10), — C(S)N(D-R10) (D-R9), — CH=NO(D-R11), — C(D-R9)=NO(D-R11), — Si(D-R13)(D-R14) (D-R12), E-10, E-12, E-18, E-32, E-35 or E-43, when m is 2 or 3, each D-X may be identical with or different from each other,Attorney Docket No. 10620-164W02

[0252] NCSURef.: 2025-138-04

[0253] further, when two D-Xs are adjacent, the adjacent two D-Xs may form 5 -membered or 6-membered ring together with carbon atoms to which the two D-Xs are bonded by forming — CF2OCF2—, — OCF2O—, — CF2OCF2O— or — OCF2CF2O—;

[0254] D-Y is halogen atom, cyano, nitro, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R4, — O(D-R5), — OSO2(D-R5), — S(O)r(D-R5), — NH(D-R7), — N(D-R7) (D-R6), — N=C(D-R9)O(D-R8), — C(O)NH2 or — C(S)NH2, when n is 2 or 3, each D-Y may be identical with or different from each other;

[0255] D-R1is Ci-Csalkyl, Ci-Csalkyl arbitrarily substituted with D-R16, Cs-Cscycloalkyl, C3-Cshalocycloalkyl, Cs-Csalkenyl, Cs-Cshaloalkenyl, Cs-Csalkynyl, Cs-Cshaloalkynyl, — N(D-R20) (D-R19), — C(O)N(D-R10) (D-R9), — C(S)N(D-R10) (D-R9), phenyl substituted with (Z)Pi, D-8 to D-18, D-21 to D-24, D-26 to D-40, D-42, D-45 to D-46, E-4, E-5, E-7, E-8, E-9, E-23 to E-25, E-27, E- 28 or E-34;

[0256] D-R2is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, cyano Ci-Cealkyl, Cs-Cecycloalkyl, Cs-Cealkenyl, Cs-Cealkynyl, — OH, Ci-Cealkoxy, Ci-Cealkylcarbonyloxy, Ci-Cealkoxycarbonyloxy, Ci-Cealkylsulfonyloxy, Ci-Cehaloalkylthio, phenylthio, phenylthio substituted with (Z)Pi, Ci-Cealkylsulfonyl, — SN(D-R18) (D-R17), — NH(D-R20), — N=CH(D-R19b), — N=C(D-R19b) (D-R19a), — C(O) (D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(S)O(D-R9) or — C(S)S(D-R9), or D-R2together with D-R1may form 3- to 5-membered ring with the nitrogen atom bonding them by forming C2-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom;

[0257] D-R3is Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Cs-Cehalocycloalkyl Ci-C4alkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4haloalkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Ci-C4alkylsulfinyl Ci-C4alkyl, Ci-C4alkylsulfonyl Ci-C4alkyl, Ci-C4haloalkylthio Ci-C4alkyl, Ci-C4haloalkylsulfinyl Ci-C4alkyl, Ci-C4haloalkylsulfonyl Ci-C4alkyl, cyano Ci-Cealkyl, Ci-C4alkoxy Ci-C4haloalkyl, Ci-C4haloalkoxy Ci-C4haloalkyl, Ci-C4alkylthio Ci-C4haloalkyl, Ci-C4alkylsulfinyl Ci-C4haloalkyl, Ci-C4alkylsulfonyl Ci-C4haloalkyl, Ci-C4haloalkylthio Ci-C4haloalkyl, Ci-C4haloalkylsulfinyl Ci-C4haloalkyl, Ci-C4haloalkylsulfonyl Ci-C4haloalkyl, cyano Ci-Cehaloalkyl, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, E-4 to E-7, E-23 to E-27 or E-28;

[0258] D-R4is halogen atom, cyano, — OH, Ci-Cealkoxy, Ci-Cehaloalkoxy, Ci-Cealkylthio, Ci-Cehaloalkylthio, Ci-Cealkylsulfinyl, Ci-Cehaloalkylsulfinyl, Ci-Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl or tri(C i-Cealkyljsilyl;

[0259] D-R5is Ci-Cealkyl, Ci-Cehaloalkyl, Ci-Cshaloalkoxy Ci-Cshaloalkyl, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, C2-Cealkenyl, C2-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, E-4 to E-9, E-23 to E-27 or E-28;Attorney Docket No. 10620-164W02

[0260] NCSURef.: 2025-138-04

[0261] D-R6is Ci-Cealkyl, Ci-Cehaloalkyl, — S(O)2(D-R9), — CHO, — C(O) (D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(S)O(D-R9) or — C(S)S(D-R9);

[0262] D-R7is hydrogen atom, Ci-Cealkyl or Ci-Cehaloalkyl;

[0263] D-R9is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-Cealkoxy Ci-C4alkyl, Ci-Cealkylthio Ci-C4alkyl, cyano Ci-Cealkyl, phenyl Ci-C4alkyl, Cs-Cscycloalkyl, C3-Cshalocycloalkyl, Cs-Cealkenyl or Cs-Cealkynyl;

[0264] D-R10is hydrogen atom or Ci-Cealkyl, or D-R10together with D-R9may form a 5-membered ring with the nitrogen atom bonding them by forming C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom;

[0265] D-R11is Ci-Cealkyl or Ci-Cehaloalkyl, or D-R11together with D-R9may form 5- or 6-membered ring with the atom bonding them by forming C2 or Csalkylene chain, in this case, the alkylene chain may be arbitrarily substituted with Ci-Cealkyl;

[0266] R15is Ci-Cealkyl or Ci-Cehaloalkyl;

[0267] D-R16is halogen atom, cyano, Cs-Cecycloalkyl, Cs-Cehalocycloalkyl, — O(D-R25), — N(D-R26) (D-R25), — S(O)r(D-R27), — SO2NH(D-R29), — SO2N(D-R29) (D-R28), —CHO, — C(O) (D-R28), — C(O)O(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(O)N(D-R29)O(D-R28), — C(S)NH(D-R29), — C(S)N(D-R29) (D-R28), — C(D-R31)=NOH, — C(D-R31)=NO(D-R30), — C(=N-D-R31)O(D-R30), — C(=N-D-R31)S(D-R30), — C(=N-D-R31)N(D-R29) (D-R30), — C(=NO-D-R31)NH(D-R29)’ — C(=NO-D-R31)N(D-R29) (D-R30), phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-8 to D-42, E-4 to E-12, E-14, E-16 to E-19, E-21 to E-23, E-26 to E-28, E-43 to E-45, M-2, M-3, M-5 or M-8 to M-10;

[0268] D-R17is Ci-Cealkyl, Ci-Cealkoxy carbonyl Ci-C4alkyl or Ci-Cealkoxy carbonyl;

[0269] D-R18is Ci-Cealkyl or benzyl;

[0270] D-R19is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-Cealkyl, phenyl Ci-Cealkyl, phenyl Ci-Cealkyl substituted with (Z)Pi, Cs-Cecycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, C3-Cealkynyl, — C(O) (D-R28), — C(O)O(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(S)NH(D-R29), — C(S)N(D-R29) (D-R28), Ci-Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with (Z)Pi, phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-18, D-21, D-25 or D-30 to D-35;

[0271] D-R19ais Ci-Cealkyl;

[0272] D-R19bis hydrogen atom or Ci-Cealkyl;

[0273] D-R20is hydrogen atom, Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, cyano Ci-Cealkyl, Cs-Cealkenyl, Cs-Cealkynyl, — CHO, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci-Cealkoxy carbonyl, Ci-Cehaloalkoxy carbonyl or Ci-Cealkylsulfonyl;Attorney Docket No. 10620-164W02

[0274] NCSURef.: 2025-138-04

[0275] D-R22is Ci-C4alkyl or C1-C4haloalkyl, or two D-R22s present on the same carbon atom may together form oxo, or thioxo;

[0276] D-R23is hydrogen atom, Ci-Cealkyl, — CHO, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci-Cealkoxy carbonyl, Ci-Cealkylsulfonyl or Ci-Cehaloalkylsulfonyl, D-R25is hydrogen atom, Ci-Cealkyl, Ci-C6haloalkyl, — C(O) (D-R33), — C(O)O(D-R33), — C(O)S(D-R33), — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), — C(S) (D-R33), — C(S)O(D-R33), — C(S)S(D-R33), — C(S)NH(D-R34), — C(S)N(D-R34) (D-R33), — S(O)2(D-R33), — S(O)2N(D-R34) (D-R33), di(Ci-C6alkyl)thiophosphoryl, phenyl or phenyl substituted with (Z)Pi;

[0277] D-R26is hydrogen atom or Ci-Cealkyl, or D-R26together with D-R25may form 4- to 5-membered ring with the nitrogen atom bonding them by forming C3-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be substituted with Ci-Cealkyl, oxo or thioxo;

[0278] D-R27is Ci-Cealkyl, Ci-Cehaloalkyl, tri(Ci-C4alkyl)silyl Ci-C4alkyl, Ci-Cealkylthio, — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), — C(S)NH(D-R34), — C(S)N(D-R34) (D-R33), phenyl or phenyl substituted with (Z)Pi;

[0279] D-R28is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R32, Cs-Cecycloalkyl, C3-Cehalocycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, phenyl or phenyl substituted with (Z)Pi;

[0280] D-R29is hydrogen atom, Ci-Cealkyl, Cs-Cealkenyl or Cs-Cealkynyl, or D-R29together with R28may form 3- to 5-membered ring with the nitrogen atom bonding them by forming C2-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom;

[0281] D-R30is Ci-Cealkyl, Cs-Cecycloalkyl Ci-C4alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Csalkenyl or Cs-Csalkynyl;

[0282] D-R31is hydrogen atom or Ci-Cealkyl, or D-R31together with D-R30may form 5- or 6-membered ring with the atom bonding them by forming C2or Csalkylene chain, in this case, the alkylene chain may be arbitrarily substituted with Ci-Cealkyl;

[0283] D-R32is halogen atom, cyano, Cs-Cecycloalkyl, Cs-Cehalocycloalkyl, Ci-C4alkoxy, Ci-C4haloalkoxy, Ci-C4alkylthio, Ci-C4haloalkylthio, Ci-C4alkoxycarbonyl, — C(O)NH2, Ci-C4alkylaminocarbonyl, di(Ci-C4alkyl)aminocarbonyl, phenyl or phenyl substituted with (Z)Pi, D-R33is Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Ci-C4alkylsulfonyl Ci-C4alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, C3-Cecycloalkyl, Cs-Cehalocycloalkyl, Cs-Cealkenyl, Cs-Cealkynyl, phenyl or phenyl substituted with (Z)Pi;

[0284] D-R34is hydrogen atom or Ci-Cealkyl;Attorney Docket No. 10620-164W02

[0285] NCSURef.: 2025-138-04

[0286] m is an integer of 1 to 3;

[0287] n is an integer of 0 to 2;

[0288] ql is 0;

[0289] q2 is an integer of 0 to 3;

[0290] q3 is an integer of 0 to 2; and

[0291] q4 is an integer of 0 to 2.

[0292] In some embodiments, D-A1is carbon;

[0293] D-A2and D-A3are carbon atom;

[0294] D-G is a benzene ring;

[0295] D-X is halogen atom, cyano, nitro, — SFs, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R4, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, C2-Cealkenyl, C2-Cehaloalkenyl, C2-Cealkynyl, C2-C6haloalkynyl, — O(D-R5), — OSO2(D-R5), — S(O)r(D-R5) or tri(Ci-C6alkyl)silyl, when m is 2 or 3, each D-X may be identical with or different from each other,

[0296] further, when two D-Xs are adjacent, the adjacent two D-Xs may form 5 -membered or 6-membered ring together with carbon atoms to which the two D-Xs are bonded by forming — CF2OCF2—, — OCF2O—, — CF2OCF2O— or — OCF2CF2O—;

[0297] D-Y is halogen atom, cyano, nitro, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R4, — O(D-R5), — OSO2(D-R5), — S(O)r(D-R5), — NH(D-R7), — N(D-R7) (D-R6), — C(O)NH2or — C(S)NH2, when n is 2 or 3, each D-Y may be identical with or different from each other;

[0298] D-R1is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R16, Cs-Cscycloalkyl, Cs-Cehalocycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, — N(D-R20) (D-R19), — C(O)N(D-R10) (D-R9), — C(S)N(D-R10) (D-R9), phenyl substituted with (Z)Pi, D-8, D-10, D-ll, D-13 to D-15, D-17, D-18, D-21 to D-23, D-26 to D-37, D-39, D-40, D-42, D-45, E-4, E-5, E-7 or E-9;

[0299] D-R2is hydrogen atom, Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, cyano Ci-Cealkyl, Cs-Cecycloalkyl, Cs-Cealkenyl, Cs-Cealkynyl, — OH, Ci-Cealkylcarbonyloxy, Ci-Cealkylsulfonyloxy, — NH2, — C(O) (D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(S)O(D-R9) or— C(S)S(D-R9);

[0300] D-R3is Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4haloalkyl, Ci-C4haloalkoxy Ci-C4haloalkyl, Ci-C4alkylthio Ci-C4haloalkyl, Ci-C4haloalkylthio Ci-C4haloalkyl, cyano Ci-Cehaloalkyl or C3-Cshalocycloalkyl;

[0301] D-R4is halogen atom, cyano, — OH, Ci-Cealkoxy, Ci-Cehaloalkoxy, Ci-Cealkylthio, Ci-Cehaloalkylthio, Ci-Cealkylsulfinyl, Ci-Cehaloalkylsulfinyl, Ci-Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl or tri(Ci-Cealkyl)silyl;Attorney Docket No. 10620-164W02

[0302] NCSURef.: 2025-138-04

[0303] D-R5is Ci-Cealkyl, Ci-Cehaloalkyl, Ci-Cshaloalkoxy Ci-Cshaloalkyl, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, C2-Cealkenyl, C2-Cehaloalkenyl, Cs-Cealkynyl or Cs-Cehaloalkynyl;

[0304] D-R6is Ci-Cealkyl, Ci-Cehaloalkyl, — CHO, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl, Cs-Cecycloalkylcarbonyl, Cs-Cehalocycloalkylcarbonyl, Ci-Cealkoxycarbonyl, Ci-Cehaloalkoxy carbonyl, Ci-Cealkylthiocarbonyl, Ci-Cealkoxythiocarbonyl, Ci-Cealkyldithiocarbonyl, Ci-Cealkylsulfonyl or Ci-Cehaloalkylsulfonyl;

[0305] D-R7is hydrogen atom or Ci-Cealkyl;

[0306] D-R9is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-Cealkoxy Ci-C4alkyl, Ci-Cealkylthio Ci-C4alkyl, cyano Ci-Cealkyl, Cs-Cscycloalkyl, Cs-Cealkenyl or C3-Cealkynyl;

[0307] D-R16is halogen atom, cyano, Cs-Cecycloalkyl, Cs-Cehalocycloalkyl, — O(D-R25), — N(D-R26) (D-R25), — S(O)r(D-R27), — SO2NH(D-R29), — SO2N(D-R29) (D-R28), — C(O) (D-R28), — C(O)O(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(O)N(D-R29)O(D-R28), — C(S)NH(D-R29), — C(S)N(D-R29) (D-R28), — C(D-R31)=NOH, — C(D-R31)=NO(D-R30), — C(=N-D-R31)O(D-R30), — C(=N-D-R31)S(D-R30), phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-8 to D-38, E-4 to E-12, E-18, E-19, E-32, E-35, E-43, M-2, M-3, M-5, M-8, M-9 or M-10;

[0308] D-R19is Ci-Cehaloalkyl, Cs-Cecycloalkyl, — C(O) (D-R28), — C(O)O(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(S)NH(D-R29), — C(S)N(D-R29) (D-R28), phenyl, phenyl substituted with (Z)Pi, D-3, D-4, D-21;

[0309] D-R20is hydrogen atom, Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, cyano Ci-Cealkyl, Cs-Cealkenyl, Cs-Cealkynyl, — CHO, Ci-Cealkylcarbonyl, Ci-Cealkoxy carbonyl or Ci-Cealkylsulfonyl;

[0310] D-R25is Ci-Cealkyl, Ci-Cehaloalkyl, Ci-Cealkylcarbonyl, Ci-Cealkoxy carbonyl, Ci-Cealkylaminocarbonyl, di(Ci-C6alkyl)aminocarbonyl or Ci-Cealkylsulfonyl;

[0311] D-R26is hydrogen atom or Ci-Cealkyl;

[0312] D-R27is Ci-Cealkyl, Ci-Cehaloalkyl or tri(Ci-C4alkyl)silyl Ci-C4alkyl;

[0313] D-R28is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, cyano Ci-Cealkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Cecycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, phenyl or phenyl substituted with (Z)Pi;

[0314] D-R29is hydrogen atom, Ci-Cealkyl, Cs-Cealkenyl or Cs-Cealkynyl;

[0315] D-R30is Ci-Cealkyl or Cs-Cecycloalkyl Ci-C4alkyl;Attorney Docket No. 10620-164W02

[0316] NCSURef.: 2025-138-04

[0317] D-R31is hydrogen atom or Ci-Cealkyl, or D-R31together with D-R30may form 5- or 6-membered ring with the atom bonding them by forming C2 or Csalkylene chain.

[0318] In some embodiments, D-X is halogen atom, cyano, nitro, — SFs, Ci-Cealkyl, Ci-Cehaloalkyl, hydroxy Ci-Cehaloalkyl, Ci-Cealkoxy Ci-Cehaloalkyl, Ci-Cehaloalkoxy Ci-Cehaloalkyl, Cs-Cshalocycloalkyl, — O(D-R5), — OSO2(D-R5) or — S(O)r(D-R5), when m is 2 or 3, each D-X may be identical with or different from each other;

[0319] D-Y is halogen atom, cyano, nitro, Ci-C4alkyl, C1-C4haloalkyl, Ci-C4alkoxy, Ci-C4haloalkoxy, Ci-Cealkylthio, Ci-Cehaloalkylthio, Ci-Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl, — NH(D-R7) or — N(D-R7) (D-R6);

[0320] D-R1is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R16, Cs-Cecycloalkyl, C3-Cealkenyl, Cs-Cshaloalkenyl, Cs-Cealkynyl, — N(D-R20)(D-R19), D-8, D-10, D-13 to D-15, D-18, D-21, D-34, D-35;

[0321] D-R2is hydrogen atom, Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, cyano Ci-Cealkyl, C3-Cealkynyl, — C(O) (D-R9) or — C(O)O(D-R9);

[0322] D-R3is Ci-Cehaloalkyl or Cs-Cshalocycloalkyl;

[0323] D-R5is Ci-Cealkyl, Ci-Cehaloalkyl or Ci-Cshaloalkoxy Ci-Cshaloalkyl;

[0324] D-R6is Ci-Cealkyl, — CHO, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci- Cealkoxy carbonyl, Ci-Cealkylthiocarbonyl, Ci-Cealkoxythiocarbonyl, Ci-Cealkyldithiocarbonyl, Ci-Cealkylsulfonyl or Ci-Cehaloalkylsulfonyl;

[0325] D-R9is Ci-Cealkyl, Ci-Cealkoxy Ci-C4alkyl, Ci-Cealkylthio Ci-C4alkyl, Cs-Cscycloalkyl, Cs-Cealkenyl or Cs-Cealkynyl;

[0326] D-R16is halogen atom, cyano, Cs-Cecycloalkyl, Cs-Cehalocycloalkyl, Ci-Cealkoxy, Ci-Cehaloalkoxy, Ci-Cealkylthio, Ci-Cehaloalkylthio, Ci-Cealkylsulfinyl, Ci-Cehaloalkylsulfinyl, Ci-Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl, Ci-Cealkylcarbonyl, — C(O)O(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(S)NH2, — C(D-R31)=NOH, — C(D-R31)=NO(D-R30), phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-8 to D-38, E-4 to E-7, E-10, E- 11 or E-32;

[0327] D-R19is Ci-Cehaloalkyl, — C(O) (D-R29), — C(O)O(D-R28), phenyl, phenyl substituted with (Z)Pi, D-3, D-4, D-21;

[0328] D-R20is hydrogen atom or Ci-Cealkyl;

[0329] D-R28is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Cs-Cecycloalkyl, C3-Cealkenyl or Cs-Cealkynyl;

[0330] D-R29is hydrogen atom or Ci-Cealkyl;

[0331] D-R30is Ci-Cealkyl;Attorney Docket No. 10620-164W02

[0332] NCSURef.: 2025-138-04

[0333] D-R31is hydrogen atom or Ci-Cealkyl; and

[0334] n is an integer of 0 or 1.

[0335] In some embodiments, the compound can comprise a compound shown below where Y is chosen from S, S=O, and S(=O)2:

[0336]

[0337] Attorney Docket No. 10620-164W02

[0338] NCSURef.: 2025-138-04

[0339]

[0340] Also described herein are compounds of Formula IX

[0341]

[0342] (E-Q)

[0343] Formula IX

[0344] including geometric and stereoisomers, N-oxides, and salts thereof, whereinAttorney Docket No. 10620-164W02

[0345] NCSURef.: 2025-138-04

[0346] Y is chosen from S, S=O, and S(=O)2;

[0347] E-Ai, E-A2, E-A3, E-A4, E-As and E-Ae are each independently selected from the group consisting of C(E-R3') and N;

[0348] n is an integer from 0 to 4;

[0349] E-Bi, E-B2 and E-B3 are each independently selected from the group consisting of C(E-R2') andN;

[0350] each E-R2' is independently of the other H or E-R2;

[0351] each E-R3' is independently of the other H or E-R3;

[0352] E-R₁ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₄-C₇-alkylcycloalkyl or C₄-C₇-cycloalkylalkyl, each unsubstituted or substituted with one or more substituents independently selected from E-R₄;

[0353] each E-R2is independently halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, N-mono- or N, N-di-Ci-C6-alkylamino, C2-Ce alkoxy carbonyl, cyano ( — CN) or nitro ( — NO2);

[0354] each E-Rais independently halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, C3-Ce-halocycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce alkyl-sulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, amino, N-mono- or N, N-di-Ci-Ce-alkylamino, Ci-Ce-alkoxy carbonyl, — CN or — NO2;

[0355] E-R4is halogen, Ci-Ce-alkyl, Ci-Ce-alkoxy, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, — CN or — NO2;

[0356] E-Q is a 5- or 6-membered heterocyclic ring, a Ce-Cio-carbocyclic ring system, a 8-, 9- or 10-membered fused hetero-bicyclic ring system, or -C(=O)-N(E-TI)(E-T2), each of the ring systems being unsubstituted or substituted with one or more substituents independently selected from halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkoxy, Ci-Ce-haloalkoxy, C2-Ce-alkenyl, C2-Ce-haloalkenyl, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, — CN, — NO2, amino, N-mono- or N, N-di-Ci-Ce-alkylamino, CO2H, Ci-Ce-alkoxy carbonyl, sulfonamido, N-mono- or N, N,di-Ci-Ce-alkylsulfonamido, CONH2, N-mono- or N, N,di-Ci-Ce-alkylaminocarbonyl, N-mono- or N, N,di-Ci-Ce-haloalkylaminocarbonyl, N — Ci-C2-haloalkylaminocarbonyl-Ci-C2-alkylaminocarbonyl, Ci-Ce-alkylcarbonylamino, C2-Ce-alkanoyl, C2-Ce-haloalkanoyl, CH2(E-Rs), a group C(O)N=CHN(CH3)2, a group C(O)N=CHNHOCH3, pyrrolidonylcarbonyl, nitro- or cyano-substituted phenyl, benzyl, phenethyl, pyridyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl, benzoyl or phenoxy; andAttorney Docket No. 10620-164W02

[0357] NCSURef.: 2025-138-04

[0358] E-Ti is H, Ci-Ce-alkyl, which is unsubstituted or substituted by Ci-C4-alkoxy, cyano, phenyl, ethenyl or ethynyl, C2-C7alkylcarbonyl, C2-C7haloalkylcarbonyl, or C2-C7-alkoxy carbonyl;

[0359] E-T2 is Ci-Ce-alkyl, a group — C(O)-E-J, a group — C(S)-E-J or a group — S(O)t-E-J; t is 1 or 2;

[0360] E-J is C₁-C₆-alkoxy; C₁-C₆-haloalkoxy; C₁-C₆-alkylthio; C₁-C₆-haloalkylthio; N(E-R₇)(E-R₈); CO₂(E-R₇); CO(E-R₇); Ci-Ce-alkyl which is unsubstituted or substituted by C3-C6-cycloalkyl, halogen, cyano, nitro, hydroxy, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, NHCO(E-R₇), C₁-C₆-alkoxy carbonyl, sulfonamido, N-mono- or N, N, di-C₁-C₄-alkylsulfonamido, CON(E-R₇)(E-R₈), C2-Ce-alkanoyl, unsubstituted or Ci-C2-alkyl-, C1-C2-haloalkyl-, Ci-C2-alkoxy-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxy carbonylsubstituted Ce-Cio-aryl, or unsubstituted or Ci-C2-alkyl-, Ci-C2-haloalkyl-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxy carbonyl-substituted 4- to 6-membered heterocyclyl; C2-C6-alkenyl; C2-Ce-alkynyl; Cs-Ce-cycloalkyl which is unsubstituted or substituted by halogen, Ci-C2-alkyl or Ci-C2-haloalkyl; Ce-Cio-aryl unsubstituted or substituted by Ci-C2-alkyl, C1-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxy carbonyl; or 4- to 6-membered heterocyclyl unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl, C1-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxycarbonyl;

[0361] E-R₇ and E-R₈ are each independently of the other H, C₁-C₆-alkyl, C₁-C₆-haloalkyl or C₃-C₆-cycloalkyl, alkylcycloalkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl;

[0362] E-R₅ is CO₂H, C₁-C₆-alkoxycarbonyl, CONH₂, N-mono- or N, N,di-C₁-C₆-alkylaminocarbonyl, N-mono- or N, N,di-C₁-C₆-haloalkylaminocarbonyl, C₁-C₆-alkylcarbonylamino, pyridinylaminocarbonyl or tetrahydrofuranyl.

[0363] In some embodiments, E-Ai, E-A2, E-A3, E-A4, E-As and E-Ae are each independently selected from the group consisting of C(E-R3') and N;

[0364] n is an integer from 0 to 4;

[0365] E-Bi, E-B2 and E-B3 are each independently selected from the group consisting of C(E-R2') andN;

[0366] each E-R2' is independently of the other H or E-R2;

[0367] each E-R3' is independently of the other H or E-R3;

[0368] E-R₁ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₄-C₇-alkylcycloalkyl or C₄-C₇-cycloalkylalkyl, each unsubstituted or substituted with one or more substituents independently selected from E-R₄;Attorney Docket No. 10620-164W02

[0369] NCSURef.: 2025-138-04

[0370] each E-R₂ is independently halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, N-mono- or N, N-di-C₁-C₆-alkylamino, C₂-C₆-alkoxy carbonyl, cyano ( — CN) or nitro ( — NO₂);

[0371] each E-Rais independently halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, C3-Ce-halocycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce alkyl-sulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, amino, N-mono- or N, N-di-Ci-C6-alkylamino, C2-Ce-alkoxy carbonyl, — CN or — NO2;

[0372] E-R₄ is halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, — CN or — NO₂; and

[0373] E-Q is a 5- or 6-membered heterocyclic ring, or a Ce-Cio-carbocyclic ring system or a 8-, 9- or 10-membered fused hetero-bicyclic ring system, each of them being unsubstituted or substituted with one or more substituents independently selected from halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, — CN, — NO2, amino, N-mono- or N, N-di-Ci-Ce-alkylamino, C2-C6-alkoxy carbonyl, sulfonamido, N-mono- or N, N,di-Ci-C4-alkylsulfonamido, N-mono- orN, N-di-Ci-Ce-alkylcarbonylamino, C2-Ce-alkanoyl and unsubstituted or halogen-, Ci-Ce-alkyl-, Ci-Ce-haloalkyl-, Ci-Ce-alkoxy-, Ci-Ce-haloalkoxy-, nitro- or cyano-substituted phenyl, benzyl, benzoyl or phenoxy.

[0374] In some embodiments, E-B₁, E-B₂ and E-B₃ are each C(E-R₂').

[0375] In some embodiments, E-Ai, E-A2, E-A3, E-A4, E-As and E-Ae are each CH.

[0376] In some embodiments, E-R₁ is C₁-C₃-haloalkyl.

[0377] In some embodiments, the compound is defined by Formula IXA

[0378]

[0379] including geometric and stereoisomers, N-oxides, and salts thereof, whereinAttorney Docket No. 10620-164W02

[0380] NCSURef.: 2025-138-04

[0381] Y is chosen from S, S=O, and S(=O)2;

[0382] n is an integer from 0 to 4;

[0383] E-R₁ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₄-C₇-alkylcycloalkyl or C₄-C₇-cycloalkylalkyl, each unsubstituted or substituted with one or more substituents independently selected from E-R₄;

[0384] each E-R2is independently halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, N-mono- or N, N-di-Ci-C6-alkylamino, C2-Ce alkoxy carbonyl, cyano ( — CN) or nitro ( — NO2);

[0385] each E-Rais independently halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, C3-Ce-halocycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce alkyl-sulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, amino, N-mono- or N, N-di-Ci-Ce-alkylamino, Ci-Ce-alkoxy carbonyl, — CN or — NO2;

[0386] E-R4is halogen, Ci-Ce-alkyl, Ci-Ce-alkoxy, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, — CN or — NO2;

[0387] E-Q is a 5- or 6-membered heterocyclic ring, or a Ce-Cio-carbocyclic ring system or a 8-, 9- or 10-membered fused hetero-bicyclic ring system, each of them being unsubstituted or substituted with one or more substituents independently selected from halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkoxy, Ci-Ce-haloalkoxy, C2-Ce-alkenyl, C2-Ce-haloalkenyl, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, — CN, — NO2, amino, N-mono- or N, N-di-Ci-Ce-alkylamino, CO2H, Ci-Ce-alkoxycarbonyl, sulfonamido, N-mono- or N, N,di-Ci-Ce-alkylsulfonamido, CONH2, N-mono- or N, N,di-Ci-Ce-alkylaminocarbonyl, N-mono- or N, N,di-Ci-Ce-haloalkylaminocarbonyl, N — C1-C2-haloalkylaminocarbonyl-Ci-C2-alkylaminocarbonyl, Ci-Ce-alkylcarbonylamino, C2-Ce-alkanoyl, C2-Ce-haloalkanoyl, CH2(E-R5), a group C(O)N=CHN(CH3)2, a group C(O)N=CHNHOCH3, pyrrolidonylcarbonyl, and unsubstituted or halogen-, Ci-Ce-alkyl-, Ci-Ce-haloalkyl-, Ci-Ce-alkoxy-, Ci-Ce-haloalkoxy-, nitro- or cyano-substituted phenyl, benzyl, phenethyl, pyridyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl, benzoyl or phenoxy;

[0388] E-Rsis CO2H, Ci-Ce-alkoxycarbonyl, CONH2, N-mono- or N, N,di-Ci-Ce-alkylaminocarbonyl, N-mono- or N, N,di-Ci-Ce-haloalkylaminocarbonyl, Ci-Ce-alkylcarbonylamino, pyridinylaminocarbonyl or tetrahydrofuranyl;

[0389] and m is an integer from 0 to 4.Attorney Docket No. 10620-164W02

[0390] NCSURef.: 2025-138-04

[0391] In some embodiments, E-Q is a 5- or 6-membered heterocyclic ring having from 1 to 4 same or different heteroatoms selected from the group consisting of N, O and S, which is further unsubstituted or substituted by one or more substituents selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, — CN, — NO2, Ci-C4-alkoxycarbonyl, sulfonamido, N-mono- or N, N-di-Ci-C4-alkylcarbonylamino, C2-C3-alkanoyl and unsubstituted or halogen- or Ci-C4-alkyl-substituted phenyl, benzyl, benzoyl and phenoxy.

[0392] In some embodiments, E-Q is a radical shown belowAttorney Docket No. 10620-164 WO2

[0393] NCSURef.: 2025-138-04

[0394] E-Q-1 E-Q-2 E-Q-3 E-Q-4

[0395] E-Q-5 E-Q-6 E-Q-7 E-Q-8 E-Q-9

[0396] E-Q-10 E-Q-11 E-Q-12 E-Q-13 E-Q-14

[0397] (E-R)r(E-R)r(E-R)r,

[0398] H H

[0399] E-Q-15 E-Q-16 E-Q-17 E-Q-18 E-Q-19 (E-R)r(E-R)r(E-R), (,E-R)r J / E'R)rN

[0400] E-Q-20 E-Q-21 E-Q-22 E-Q-23 E-Q-24 (E-R)r(E-R)r(E-R)r1 / N'N il — < / — N' ’nN-NO"'\E-R)I^■^(E-R), E-Q-25 E-Q-26 " E-Q-27 E-Q-28 E-Q-29 (E-R)r H(E-R)r(E-R)r(E-R)r(E-R)r / Wi - — N I N- N'NHu E-Q-30 E-Q-31 E-Q-32 E-Q-33 E-Q-34 °- - N=N Y^(E-R), (E-R),N*^(E-R)rN^(E-R), N^E-R),

[0401] ' E-Q-39 E-Q-35 E-Q-36 E-Q-37 E-Q-38

[0402] (E-R)r N-0,N=”N'^S NHJ\A-(E-R), ’fSE-R)r^\E. R' E-Q-401E-Q-41 E-Q-42 E-Q-43 E-Q-44 (E-R)r (E-R)r(E-R)r(E-R)r(E-R),

[0403] 6 J? _N^ N'NHN-N %., N E-Q-45 ^-Q-46 E-Q-47 E-Q-48 5 (E-R)r(E-R)- (E-R), (E-R)r<E'R>'

[0404] 7N ^^2 " -N- 3 ” E-Q-50 E-Q-51 E-Q-52 E-Q-53 E-Q-54 M (E-R)r N(E-R)r M(E-R)r N(E-R)r(E-R) (E-R),

[0405] TKi

[0406]

[0407] E-Q-55 E-Q-56 E-Q-57 E-Q-58 E-Q-5948E-Q-60Attorney Docket No. 10620-164 WO2

[0408] NCSURef.: 2025-138-04

[0409] XCTJHE-R),. XTTr(E-R)r'Y~y(E’R)rsV E-Q-61 E-Q-62 E H-Q-63 E-Q-64 E-Q-65

[0410] E-Q-66 E-Q-67 E-Q-68 E-Q-69 E-Q-70

[0411] E-Q-71 E-Q-72

[0412] E-Q-76 E-Q-77

[0413] E-Q-81 E-Q-82 E-Q-83E-Q’84E-Q-85

[0414] H (E-R)r£ 'I V H E-Q-88 E-Q-89 E-Q-90 E-Q-86 E-Q-87

[0415]

[0416] E-Q-91 E-Q-92 E-Q-93 E-Q-94 E-Q-95Attorney Docket No. 10620-164W02

[0417] NCSURef.: 2025-138-04

[0418] E-Q-96 E-Q-97 E-Q-98 E-Q-99

[0419] E-Q-100 E-Q-101 E-Q-102 E-Q-103

[0420] E-Q-104 E-Q-105 E-Q-106 E-Q-107

[0421] E-Q-108 E-Q-109 E-Q-110 E-Q-111

[0422] E-Q-112 E-Q-113 E-Q-114 E-Q-115

[0423] E-Q-116 E-Q-117 E-Q-118 E-Q-119

[0424] E-Q-120 E-Q-121 E-Q-122 E-Q-123

[0425] H

[0426] E-Q-128 E-Q-131

[0427]

[0428] E-Q-132 E-Q-133

[0429] wherein r is an integer from 0 to 3 and E-R is independently selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, Ci-C2-haloalkylthio, — CN, — NO2, and Ci-C4-alkoxy carbonyl.

[0430] In some embodiments, Q is a radical shown belowAttorney Docket No. 10620-164W02

[0431] NCSURef.: 2025-138-04

[0432] E-Q-24a E-Q-26a E-Q-30a E-Q-32a

[0433]

[0434] E-Q-34a E-Q-44 E-Q-47

[0435] wherein E-R is independently selected from the group consisting of halogen, Ci-C2-alkyl, C1-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, Ci-C2-haloalkylthio, — CN, — NO2, and C1-C4-alkoxy carbonyl

[0436] In some embodiments, E-Q is the radical E-Q-34, E-Q-43 or E-Q-47, wherein r is in each case 0.

[0437] In some embodiments, n is an integer from 1 to 3, E-Ri is Ci-Cs-haloalkyl, each E-R2 and E-R3 is independently selected from the group consisting of halogen, Ci-C2-alkyl, C1-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, Ci-C2-haloalkylthio, — CN and — NO2, m is an integer from 0 to 2, and E-Q is either

[0438] (i) phenyl, which is unsubstituted or substituted by 1 to 3, same or different substituents selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, Ci-C2-haloalkylthio, — CN, — NO2, and unsubstituted or halogen-, Ci-C2-alkyl-, Ci-C2-haloalkyl-, Ci-C2-alkoxy-, Ci-C2-haloalkoxy-, — CN and — NCh-substituted phenyl or phenoxy, or is

[0439] (ii) a 5- or 6-membered heterocyclic ring having from 1 to 3 same or different heteroatoms selected from the group consisting of N, O and S, which is further unsubstituted or substituted by halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, C1-C2-haloalkylthio, — CN, — NO2 or Ci-C4-alkoxy carbonyl, or is

[0440] (iii) a fused hetero-bicyclic ring system comprising a 5- or 6-membered heterocyclic ring having from 1 to 3 same or different heteroatoms selected from the group consisting of N, O and S, to which is attached an annulated ring, and which is further unsubstituted or substituted by halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, Ci-C2-haloalkylthio, — CN, — NChor Ci-C4-alkoxy carbonyl.

[0441] In some embodiments, n is an integer from 1 to 3,

[0442] E-Riis CF3,

[0443] each E-I is independently selected from the group consisting of halogen, C1-C2-haloalkyl, Ci-C2-haloalkoxy and — CN,Attomey Docket No. 10620-164W02

[0444] NCSURef.: 2025-138-04

[0445] m is 0, and

[0446] E-Q is either

[0447] (i) a 5- or 6-membered heteroaromatic ring selected from

[0448] E-Q-5 E-Q-6 E-Q-7 ” E-Q- 15 E-Q-16 E-Q-17

[0449] E-Q-30 E-Q-31 E-Q-32 E-Q-33 E-W-04 E-Q-24

[0450]

[0451] E-Q-43 E-Q-47 E-Q-50 E-Q-52 E-Q- 54 wherein r is an integer from 0 to 3 and E-R is independently selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, Ci-C2-haloalkylthio, — CN, — NO2, and Ci-C4-alkoxycarbonyl, or

[0452] (ii) a fused hetero-bicyclic ring system selected from

[0453]

[0454] In some embodiments, n is an integer from 1 to 3,

[0455] E-Ri is CF3,

[0456] each E-R2is independently selected from the group consisting of halogen, C1-C2-haloalkyl, Ci-C2-haloalkoxy and — CN,

[0457] m is 0, and

[0458] Q is chosen from E-Q-5, E-Q-14, E-Q-24, E-Q-25, E-Q-26, E-Q-30, E-Q-32, E-Q-34, E- Q-43, E-Q-44, E-Q-47, E-Q-49, E-Q-50, and E-Q-75 wherein r is an integer of 0 or 1, and E-R is independently selected from the group consisting of Ci-C2-alkyl, halo-Ci-C2-alkyl, halo-Ci-C2-Attorney Docket No. 10620-164W02

[0459] NCSURef.: 2025-138-04

[0460] alkylcarbonyl, cyano, Ci-C4-alkoxycarbonyl, Ci-C4-alkoxycarbonylmethyl, carboxy-Ci-C2-alkyl, aminocarbonyl, N-mono- or N, N-di-Ci-C2-alkylaminocarbonyl, halo-Ci-C2-alkylaminocarbonylmethyl, halo-Ci-C2-alkylaminocarbonylmethylaminocarbonyl, halovinyl, — C(O)N=CHN(CH3)2, — C(O)N=CHNHOCH3, unsubstituted or halogen- or Ci-C2-alkoxy-substituted phenyl, benzyl and phenylethyl, unsubstituted and halogen-substituted 2-, 3- and 4-pyridyl and pyridylmethyl, pyridylcarbonylaminomethyl, pyrrolidinecarbonyl, and 2-tetrahydrofuranylmethyl.

[0461] In some embodiments, E-Riis CF3.

[0462] In some embodiments, E-Q is a 5- or 6-membered heterocyclic ring having from 1 to 3 same or different heteroatoms.

[0463] In some embodiments, m is 0.

[0464] In some embodiments, E-Q is phenyl, which is substituted by 1 or 2 same or different substituents.

[0465] In some embodiments, E-Q is E-Q-24, E-Q-26, E-Q-30, E-Q-32, E-Q-34, E-Q-44 or E-Q-47.

[0466] In some embodiments, the compound comprises one of the following

[0467] CF3Cl ci

[0468] Compound E-1.1 N I ^ / N

[0469]

[0470] wherein Y is chosen from S, S=O, and S(=O)2.

[0471] Also described herein are compounds of Formula XAttorney Docket No. 10620-164W02

[0472] NCSURef.: 2025-138-04

[0473]

[0474] including all geometric and stereoisomers, N-oxides, S-oxides and salts thereof, wherein

[0475] Y is chosen from S, S=O, and S(=O)2;

[0476] F-X is S(O)m, O or N(F-Rs') and F-Xl and F-X2 are each independently of the other C(F-R3') orN,

[0477] n is an integer from 0 to 4;

[0478] m is an integer from 0 to 2;

[0479] F-Rs' is H, =0, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkylcarbonyl or Ci-Ce-alkoxy carbonyl;

[0480] F-Bi, F-B2 and F-B3 are each independently selected from the group consisting of C(F-R2') andN;

[0481] each F-R2' is independently of the other H or F-R2;

[0482] each F-R3' is independently of the other H or F-R3;

[0483] F-Ri is Ci-Cealkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Cs-Ce-cycloalkyl, C4-C7-alkylcycloalkyl or C4-C?cycloalkylalkyl, each unsubstituted or substituted with one or more substituents independently selected from F-R4;

[0484] F-R4is halogen, Ci-Ce-alkyl, Ci-Ce-alkoxy, Ci-Ce-alkylthio, Ci-Cealkylsulfinyl, Ci-Ce-alkyl-sulfonyl, cyano or nitro;

[0485] each F-R2is independently halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Cealkylsulfonyl, Ci-Ce-haloalkylsulfonyl, N-mono- or N, N-di-Ci-C6-alkylamino, Ci-Ce-alkoxy carbonyl, cyano ( — CN) or nitro ( — NO2);

[0486] each F-R3 is independently H, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Cehaloalkylthio, Ci-Cealkyl-sulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Cealkylsulfonyl, Ci-Ce-haloalkylsulfonyl, amino,Attorney Docket No. 10620-164W02

[0487] NCSURef.: 2025-138-04

[0488] N-mono- or N, N-di-Ci-C6-alkylamino, Ci-Ce-alkoxy carbonyl, cyano, nitro or unsubstituted or halogen-, Ci-Ce-alkyl-, Ci-Ce-haloalkyl-, Ci-Ce-alkoxy-, Ci-Ce-haloalkoxy-, amino-, cyano- or nitro-substituted phenyl, pyridyl or pyrimidyl;

[0489] F-Rs is H, =0 (a carbonyl group), Ci-Ce-alkyl, Ci-Ce-haloalkyl, halogen or cyano; or F-Rs and F-X2 together with the intermediate C-atoms form a 5- or 6-membered carbocyclic ring;

[0490] F-R.6 is H; Ci-Ce-alkyl, which is unsubstituted or substituted by Ci-C4-alkoxy, cyano, phenyl, ethenyl or ethynyl; C2-C?alkylcarbonyl; C2-C?haloalkylcarbonyl; C2-C?-alkoxycarbonyl;

[0491] F-Z is Ci-Ce-alkyl, a group — C(O)-F-Q, a group — C(S)-F-Q or a group — S(O)t-F-Q; t is 1 or 2;

[0492] F-Q is Ci-Ce-alkoxy; Ci-Ce-haloalkoxy; Ci-Ce-alkylthio; Ci-Ce-haloalkylthio; N(F-R?)(F-Rs); CO2(F-R?); CO(F-R?); Ci-Ce-alkyl which is unsubstituted or substituted by C3-C6-cycloalkyl, halogen, cyano, nitro, hydroxy, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, NHCO(F-R?), Ci-Ce-alkoxycarbonyl, sulfonamido, N-mono- orN, N, di-Ci-C4-alkylsulfonamido, CON(F-R?)( F-Rs), C2-Ce-alkanoyl, unsubstituted or Ci-C2-alkyl-, C1-C2-haloalkyl-, Ci-C2-alkoxy-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxy carbonylsubstituted Ce-Cio-aryl, or unsubstituted or Ci-C2-alkyl-, Ci-C2-haloalkyl-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxy carbonyl-substituted 4- to 6-membered heterocyclyl; C2-C6-alkenyl; C2-Ce-alkynyl; Cs-Ce-cycloalkyl which is unsubstituted or substituted by halogen, Ci-C2-alkyl or Ci-C2-haloalkyl; Ce-Cio-aryl unsubstituted or substituted by Ci-C2-alkyl, C1-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxy carbonyl; or 4- to 6-membered heterocyclyl unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl, C1-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxycarbonyl; and

[0493] F-R7 and F-Rs are each independently of the other H, Ci-Ce-alkyl, Ci-Ce-haloalkyl or C3-Ce-cycloalkyl, alkylcycloalkyl, C2-Ce-alkenyl or C2-C6-alkynyl.

[0494] In some embodiments, F-Q is Ci-Ce-alkoxy; Ci-Ce-haloalkoxy; Ci-Ce-alkylthio; Ci-Ce-haloalkylthio; N(F-R?)(F-Rs); CCh(F-R7); CO(F-R?); Ci-Ce-alkyl which is unsubstituted or substituted by Cs-Ce-cycloalkyl, halogen, cyano, nitro, hydroxy, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, Ci-Ce-alkylcarbonylamino, Ci-Ce-haloalkylcarbonylamino, Ci-Ce-alkoxycarbonyl, sulfonamido, N-mono- or N, N, di-Ci-C4-alkylsulfonamido, N-mono- or N, N-di-Ci-Ce-alkylaminocarbonyl, N-mono- or N, N-di-Ci-Ce-haloalkylaminocarbonyl, C2-Ce-alkanoyl, unsubstituted or Ci-C2-alkyl-, Ci-C2-haloalkyl-, C1-C2-alkoxy-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxycarbonyl-substituted Ce-Cio-aryl,Attorney Docket No. 10620-164W02

[0495] NCSURef.: 2025-138-04

[0496] or unsubstituted or Ci-C2-alkyl-, Ci-C2-haloalkyl-, Ci-C2-alkoxy-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxy carbonyl-substituted 4- to 6-membered heterocyclyl; C2-Ce-alkenyl; C2-Ce-alkynyl; Cs-Ce-cycloalkyl which is unsubstituted or substituted by halogen, Ci-C2-alkyl or Ci-C2-haloalkyl; Ce-Cio-aryl unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl, C1-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4alkoxy carbonyl; or 4- to 6-membered heterocyclyl unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, C1-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxy carbonyl; and

[0497] F-R7 and F-Rs are each independently of the other H, Ci-Ce-alkyl, Ci-Ce-haloalkyl or C3-Ce-cycloalkyl.

[0498] In some embodiments, F-Bi, F-B2 and F-B3 are each C(F-R2').

[0499] In some embodiments, F-X is S(O)m, one of F-Xi and F-X2is C(F-R3') and the other one is N or independently C(F-R3'), wherein F-R3' is each independently H or Ci-C2-alkyl, and m is an integer from 0 to 2.

[0500] In some embodiments, F-X is O, one of F-Xi and F-X2is C(F-R3') and the other one is N or independently C(F-R3'), wherein F-R3' is each independently H or Ci-C2-alkyl.

[0501] In some embodiments, F-Ri is Ci-Cs-haloalkyl, in particular CF3.

[0502] In some embodiments, the compound is defined by Formula XA

[0503]

[0504] Formula XA

[0505] including all geometric and stereoisomers, N-oxides, S-oxides and salts thereof, wherein

[0506] Y is chosen from S, S=O, and S(=O)2;

[0507] F-X is S(O)m, O or N(F-Rs') and F-XI and F-X2 are each independently of the other C(F-R3') orN,

[0508] n is an integer from 0 to 4;

[0509] m is an integer from 0 to 2;

[0510] each F-R3' is independently of the other H or F-R3;Attorney Docket No. 10620-164W02

[0511] NCSURef.: 2025-138-04

[0512] each F-R3 is independently H, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Cehaloalkylthio, Ci-Cealkyl-sulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Cealkylsulfonyl, Ci-Ce-haloalkylsulfonyl, amino, N-mono- or N, N-di-Ci-C6-alkylamino, Ci-Ce-alkoxy carbonyl, cyano, nitro or unsubstituted or halogen-, Ci-Ce-alkyl-, Ci-Ce-haloalkyl-, Ci-Ce-alkoxy-, Ci-Ce-haloalkoxy-, amino-, cyano- or nitro-substituted phenyl, pyridyl or pyrimidyl;

[0513] F-Z is Ci-Ce-alkyl, a group — C(O)-F-Q, a group — C(S)-F-Q or a group — S(O)t-F-Q; t is 1 or 2;

[0514] F-Q is Ci-Ce-alkoxy; Ci-Ce-haloalkoxy; Ci-Ce-alkylthio; Ci-Ce-haloalkylthio; N(F-R?)(F-Rs); CO2(F-R?); CO(F-R?); Ci-Ce-alkyl which is unsubstituted or substituted by C3-C6-cycloalkyl, halogen, cyano, nitro, hydroxy, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, NHCO(F-R?), Ci-Ce-alkoxycarbonyl, sulfonamido, N-mono- orN, N, di-Ci-C4-alkylsulfonamido, CON(F-R?)( F-Rs), C2-Ce-alkanoyl, unsubstituted or Ci-C2-alkyl-, C1-C2-haloalkyl-, Ci-C2-alkoxy-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxy carbonylsubstituted Ce-Cio-aryl, or unsubstituted or Ci-C2-alkyl-, Ci-C2-haloalkyl-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxy carbonyl-substituted 4- to 6-membered heterocyclyl; C2-C6-alkenyl; C2-Ce-alkynyl; Cs-Ce-cycloalkyl which is unsubstituted or substituted by halogen, Ci-C2-alkyl or Ci-C2-haloalkyl; Ce-Cio-aryl unsubstituted or substituted by Ci-C2-alkyl, C1-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxy carbonyl; or 4- to 6-membered heterocyclyl unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl, C1-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxycarbonyl; and

[0515] F-R7 and F-Rs are each independently of the other H, Ci-Ce-alkyl, Ci-Ce-haloalkyl or C3-Ce-cycloalkyl, alkylcycloalkyl, C2-Ce-alkenyl or C2-C6-alkynyl.

[0516] In some embodiments, F-Z is a group — C(O)-F-Q.

[0517] In some embodiments, F-Q is straight-chain or branched Ci-C4-alkyl, which is each unsubstituted or substituted by Cs-Ce-cycloalkyl, halogen, cyano, hydroxy, Ci-C4alkoxy, C1-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4alkylsulfonyl, Ci-C2-alkylcarbonylamino or Ci-C2-haloalkylcarbonylamino; unsubstituted or methyl-substituted Cs-Ce-cycloalkyl; phenyl, which is unsubstituted or substituted by halogen, Ci-C2-alkyl, C1-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, cyano or Ci-C4alkoxy carbonyl; thienyl, furyl, oxazolyl, thiazolyl, pyridyl or pyrimidinyl, which are each unsubstituted or substituted by C1-C2-alkyl, Ci-C2-haloalkyl or Ci-C4-alkoxy carbonyl; or pyrrolidinyl, tetrahydrofuranyl,Attorney Docket No. 10620-164W02

[0518] NCSURef.: 2025-138-04

[0519] tetrahydrothiophenyl, piperidinyl, piperazinyl, morpholinyl, tetrahydropyranyl or thianyl which are each unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl or Ci-C4-alkoxy carbonyl.

[0520] In some embodiments, the compound is defined by Formula XB

[0521]

[0522] Formula XB

[0523] including all geometric and stereoisomers, N-oxides, S-oxides and salts thereof, wherein

[0524] Y is chosen from S, S=O, and S(=O)2;

[0525] F-X is S(O)m, O or N(F-Rs') and F-X1 and F-X2 are each independently of the other C(F-R3') or N,

[0526] n is an integer from 0 to 4;

[0527] m is an integer from 0 to 2;

[0528] each F-R3' is independently of the other H or F-R3;

[0529] each F-R3 is independently H, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Cehaloalkylthio, Ci-Cealkyl-sulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Cealkylsulfonyl, Ci-Ce-haloalkylsulfonyl, amino, N-mono- or N, N-di-Ci-C6-alkylamino, Ci-Ce-alkoxy carbonyl, cyano, nitro or unsubstituted or halogen-, Ci-Ce-alkyl-, Ci-Ce-haloalkyl-, Ci-Ce-alkoxy-, Ci-Ce-haloalkoxy-, amino-, cyano- or nitro-substituted phenyl, pyridyl or pyrimidyl;

[0530] F-Z is Ci-Ce-alkyl, a group — C(O)-F-Q, a group — C(S)-F-Q or a group — S(O)t-F-Q; t is 1 or 2;

[0531] F-Q is Ci-Ce-alkoxy; Ci-Ce-haloalkoxy; Ci-Ce-alkylthio; Ci-Ce-haloalkylthio; N(F-R?)(F-Rs); CO2(F-R?); CO(F-R?); Ci-Ce-alkyl which is unsubstituted or substituted by C3-C6-cycloalkyl, halogen, cyano, nitro, hydroxy, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, NHCO(F-R?), Ci-Ce-alkoxycarbonyl, sulfonamido, N-mono- orN, N, di-Ci-C4-alkylsulfonamido, CON(F-R?)( F-Rs), C2-Ce-alkanoyl, unsubstituted or Ci-C2-alkyl-, C1-C2-Attorney Docket No. 10620-164W02

[0532] NCSURef.: 2025-138-04

[0533] haloalkyl-, Ci-C2-alkoxy-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxy carbonylsubstituted Ce-Cio-aryl, or unsubstituted or Ci-C2-alkyl-, Ci-C2-haloalkyl-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxy carbonyl-substituted 4- to 6-membered heterocyclyl; C2-C6-alkenyl; C2-Ce-alkynyl; Cs-Ce-cycloalkyl which is unsubstituted or substituted by halogen, Ci-C2-alkyl or Ci-C2-haloalkyl; Ce-Cio-aryl unsubstituted or substituted by Ci-C2-alkyl, C1-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxy carbonyl; or 4- to 6-membered heterocyclyl unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl, C1-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxycarbonyl; and

[0534] F-R7 and F-Rs are each independently of the other H, Ci-Ce-alkyl, Ci-Ce-haloalkyl or C3-Ce-cycloalkyl, alkylcycloalkyl, C2-Ce-alkenyl or C2-C6-alkynyl.

[0535] In some embodiments, F-Z is a group — C(O)-F-Q.

[0536] In some embodiments, F-Q is straight-chain or branched Ci-C4-alkyl, which is each unsubstituted or substituted by Cs-Ce-cycloalkyl, halogen, cyano, hydroxy, Ci-C4alkoxy, C1-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4alkylsulfonyl, Ci-C2-alkylcarbonylamino or Ci-C2-haloalkylcarbonylamino; unsubstituted or methyl-substituted Cs-Ce-cycloalkyl; phenyl, which is unsubstituted or substituted by halogen, Ci-C2-alkyl, C1-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, cyano or Ci-C4alkoxy carbonyl; thienyl, furyl, oxazolyl, thiazolyl, pyridyl or pyrimidinyl, which are each unsubstituted or substituted by C1-C2-alkyl, Ci-C2-haloalkyl or Ci-C4-alkoxy carbonyl; or pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, piperidinyl, piperazinyl, morpholinyl, tetrahydropyranyl or thianyl which are each unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl or Ci-C4-alkoxy carbonyl.

[0537] In some embodiments, F-Q is straight-chain or branched Ci-C4-alkyl, Ci-Cs-haloalkyl, cyclopropylmethyl, cyano-Ci-C2-alkyl, Ci-C2-alkoxy-Ci-C2-alkyl, Ci-C2-alkylthio-Ci-C2-alkyl, Ci-C2-alkylsulfinyl-Ci-C2-alkyl or Ci-C2-alkylsulfonyl-Ci-C2-alkyl.

[0538] In some embodiments, n is an integer from 1 to 3; each F-R.2is independently selected from the group consisting of halogen, Ci-Ce-haloalkyl, Ci-Ce-haloalkoxy and cyano; X is S(O)m, O or N(F-Rs'); m is an integer from 0 to 2; F-Rs' is H or Ci-C2-alkyl; one of F-Xi and F-X2is C(F-R3') and the other one is N or independently C(F-R3'); F-R3' is H or Ci-C2-alkyl; F-Z is a group — S(O)2— Ci-C2-alkyl or a group — C(O)-Q; and F-Q is straight-chain or branched C1-C4-alkyl, which is each unsubstituted or substituted by Cs-Ce-cycloalkyl, halogen, cyano, C1-C4-alkoxy, Ci-C2-haloalkoxy, Ci-C4alkylthio, Ci-C2-haloalkylthio, Ci-C4alkylsulfinyl, C1-C4-alkylsulfonyl, Ci-C2-alkylcarbonylamino or Ci-C2-haloalkylcarbonylamino; unsubstituted or methyl-substituted Cs-Ce-cycloalkyl; phenyl, which is unsubstituted or substituted by halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, cyano or Ci-C4-alkoxycarbonyl;Attorney Docket No. 10620-164W02

[0539] NCSURef.: 2025-138-04

[0540] thienyl, furyl, oxazolyl, thiazolyl, pyridyl or pyrimidinyl, which are each unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl or Ci-C4-alkoxycarbonyl; or pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, piperidinyl, piperazinyl, morpholinyl, tetrahydropyranyl or thianyl which is each unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl or C1-C4-alkoxy carbonyl.

[0541] In some embodiments, the compound is defined by Formula XC

[0542]

[0543] including all geometric and stereoisomers, N-oxides, and salts thereof, wherein Y is chosen from S, S=O, and S(=O)2; the radicals F-R2 are each independently of the other H, halogen or trifluoromethyl; F-R3' is hydrogen or methyl; F-Z is a radical — C(O)-F-Q; and F-Q is straightchain or branched Ci-C4-alkyl, Ci-Cs-haloalkyl, cyclopropylmethyl, cyano-Ci-C2-alkyl, C1-C2-alkoxy-Ci-C2-alkyl, Ci-C2-alkylthio-Ci-C2-alkyl, Ci-C2-alkylsulfinyl-Ci-C2-alkyl or C1-C2-alkylsulfonyl-Ci-C2-alkyl.

[0544] In some embodiments, the compound is defined by Formula XD

[0545]

[0546] including all geometric and stereoisomers, N-oxides, and salts thereof, wherein Y is chosen from S, S=O, and S(=O)2; the radicals F-R2 are each independently of the other H, halogen or trifluoromethyl; F-R3' is hydrogen or methyl; F-Z is a radical — C(O)-F-Q; and F-Q is straightchain or branched Ci-C4-alkyl, Ci-Cs-haloalkyl, cyclopropylmethyl, cyano-Ci-C2-alkyl, C1-C2-Attorney Docket No. 10620-164W02

[0547] NCSURef.: 2025-138-04

[0548] alkoxy-Ci-C2-alkyl, Ci-C2-alkylthio-Ci-C2-alkyl, Ci-C2-alkylsulfinyl-Ci-C2-alkyl or C1-C2-alkylsulfonyl-Ci-C2-alkyl.

[0549] In some embodiments, the compound is defined by Formula XE

[0550]

[0551] Formula XE

[0552] including all geometric and stereoisomers, N-oxides, and salts thereof, wherein Y is chosen from S, S=O, and S(=O)2; the radicals F-R2 are each independently of the other H, halogen or trifluoromethyl; F-R3' is hydrogen or methyl; F-Z is a radical — C(O)-F-Q; and F-Q is straightchain or branched Ci-C4-alkyl, Ci-Cs-haloalkyl, cyclopropylmethyl, cyano-Ci-C2-alkyl, C1-C2-alkoxy-Ci-C2-alkyl, Ci-C2-alkylthio-Ci-C2-alkyl, Ci-C2-alkylsulfinyl-Ci-C2-alkyl or C1-C2-alkylsulfonyl-Ci-C2-alkyl.

[0553] In some embodiments, the compound is defined by Formula XF

[0554]

[0555] including all geometric and stereoisomers, N-oxides, and salts thereof, wherein Y is chosen from S, S=O, and S(=O)2; the radicals F-R2 are each independently of the other H, halogen or trifluoromethyl; F-R3' is hydrogen or methyl; F-Z is a radical — C(O)-F-Q; and F-Q is straightchain or branched Ci-C4-alkyl, Ci-Cs-haloalkyl, cyclopropylmethyl, cyano-Ci-C2-alkyl, C1-C2-alkoxy-Ci-C2-alkyl, Ci-C2-alkylthio-Ci-C2-alkyl, Ci-C2-alkylsulfinyl-Ci-C2-alkyl or C1-C2-alkylsulfonyl-Ci-C2-alkyl.

[0556] In some embodiments, the compound comprises one of the followingAttorney Docket No. 10620-164W02

[0557] NCSURef.: 2025-138-04

[0558]

[0559] wherein Y is chosen from S, S=O, and S(=O)2.

[0560] In some embodiments, the compound is defined by the formula below

[0561]

[0562] wherein Y is chosen from S, S=O, and S(=O)2, and F-A comprises one of the following:Attorney Docket No. 10620-164 WO2

[0563] NCSURef.: 2025-138-04

[0564] NH2F-1.1 F-1.5 F-1.6

[0565] Me O Me O Me O Me O Me O Me O

[0566] F-1.52 F F-1.54 F-1.49 F-1.50 F-1.51 -1.53 Me O Me O

[0567]

[0568] F-1.56 F-1.57

[0569] In some embodiments, the compound is defined by the formula belowAttorney Docket No. 10620-164W02

[0570] NCSURef.: 2025-138-04

[0571]

[0572] wherein Y is chosen from S, S=O, and S(=O)2, and F-A comprises one of the following:

[0573]

[0574] F-2.1 F-2.2

[0575] In some embodiments, the compound is defined by the formula below

[0576]

[0577] wherein Y is chosen from S, S=O, and S(=O)2, and F-A comprises one of the following:Attorney Docket No. 10620-164 WO2

[0578] NCSURef.: 2025-138-04

[0579] NH2F-3.1

[0580] O N CF2CF2CF3H

[0581] F-3.21 F-3.22 F-3.23

[0582] O

[0583] N ruNFf HCH3 HEtF-3.26 F-3.27 F-3.28 F-3.29 F-3.30

[0584] F-3.36 F-3.31 F-3.32

[0585] O

[0586] F-3.37 F-3.38

[0587] Me O Me O Me O Me O Me O Me O

[0588] F-3. F-3.54 F-3.49 52 F-3.53 Me O Me O

[0589]

[0590] F-3.57 In some examples, the 1,4,2-oxathiazole analogs of furalaner can be the compound shown belowAttorney Docket No. 10620-164W02

[0591] NCSURef.: 2025-138-04

[0592]

[0593] wherein Y is chosen from S, S=O, and S(=O)2.

[0594] In some examples, the 1,4,2-oxathiazole analogs of furalaner can be the compound shown below.

[0595]

[0596] In some examples, the 1,4,2-oxathiazole analogs of afoxolaner can be the compound shown belowAttorney Docket No. 10620-164W02

[0597] NCSURef.: 2025-138-04

[0598]

[0599] wherein Y is chosen from S, S=O, and S(=O)2.

[0600] In some examples, the 1,4,2-oxathiazole analogs of afoxolaner can be the compound shown below.

[0601]

[0602] In some examples, the 1,4,2-oxathiazole analogs of lotilaner can be the compound shown below

[0603]

[0604] CF3

[0605] wherein Y is chosen from S, S=O, and S(=O)2.Attorney Docket No. 10620-164W02

[0606] NCSURef.: 2025-138-04

[0607] In some examples, the 1,4,2-oxathiazole analogs of lotilaner can be the compound shown below.

[0608]

[0609] 1,4,2-Oxathiazole Analogs of Isocycloseram

[0610] In some examples, described herein are 1,4,2-oxathiazole analogs of isocycloseram. Isocycloseram and related compounds are described for example in International Publication Nos. WO2011 / 067272, W02021 / 000867, and W02021 / 000865, and U. S. Patent Nos. 8,735,362, 9,609,869, 10,206,400, 10,750,745, 11,357,231, 12,371,410, and 12,312,319, each of which is incorporated by reference in its entirety. Described herein are analogs of these compounds which include a 1,4,2-oxathiazole ring.

[0611] For example, described herein are compounds defined by Formula VII

[0612]

[0613] Formula VII

[0614] wherein

[0615] Y is chosen from S, S=O, and S(=O)2;

[0616] C-A1, C-A2, C-A3and C-A4are independently of one another C-H, C-(C-R5), or nitrogen; C-G1is oxygen or sulfur;

[0617] C-L is a single bond or Ci-Cs alkylene;Attorney Docket No. 10620-164W02

[0618] NCSURef.: 2025-138-04

[0619] C-R1is hydrogen, C1-C8 alkyl, C1-C8 alkylcarbonyl-, C1-C8 alkoxy, C1-C8 alkoxy-C1-C8 alkyl, or C1-C8 alkoxy carbonyl;

[0620] C-R2is hydrogen, C1-C8 haloalkyl or C1-C8 alkyl;

[0621] C-R3is C1-C8 haloalkyl;

[0622] C-R4is aryl or aryl substituted by one to three C-R6, or C-R4is heterocyclyl or heterocyclyl substituted by one to three C-R6;

[0623] each C-R5is independently halogen, cyano, nitro, Ci-Cs alkyl, Cs-Cs cycloalkyl, C1-C8 haloalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, Ci-Cs alkoxy, Ci-Cs haloalkoxy, Ci-Cs alkoxy carbonyl-, or two C-R5on adjacent carbon atoms together form a -CH=CH-CH=CH- bridge or a -N=CH-CH=CH- bridge;

[0624] each C-R6is independently halogen, cyano, nitro, Ci-Cs alkyl, C1-C8 haloalkyl, Ci-Cs alkoxy, or Ci-C 8 haloalkoxy;

[0625] C-Y1is C(C-R7)(C-R8) or C=O;

[0626] C-Y2, C-Y3and C-Y4are independently C(C-R7)(C-R8), C=O, N-(C-R9), O, S, SO, or SO2, wherein at least two adjacent ring atoms in the ring formed by C-Y1, C-Y2, C-Y3and C-Y4are heteroatoms;

[0627] each C-R7and C-R8is independently hydrogen, halogen, Ci-Cs alkyl, or C1-C8 haloalkyl; each C-R9is independently hydrogen, cyano, cyano-Ci-Cs alkyl, Ci-Cs alkyl, C1-C8 haloalkyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, or C3-C8 cycloalkyl-Ci-Cs alkyl, C3-C8 cycloalkyl-Ci-Cs alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, or Cs-Cscycloalkyl-Ci-Cshaloalkyl, Ci-Cs hydroxyalkyl, Ci-Csalkoxy-Ci-Cs alkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 alkynyl, C2-Cs haloalkynyl, phenyl, phenyl substituted by one to three C-R10, phenyl-Ci-C4 alkyl, phenyl-Ci-C4 alkyl wherein the phenyl moiety is substituted by one to three C-R10, 5-6 membered heteroaryl-Ci-C4 alkyl or 5-6 membered heteroaryl-Ci-C4 alkyl wherein the heteroaryl moiety is substituted by one to three C-R10, or Ci-C4alkyl-(Ci-C4alkyl-O-N=)C-CH2-;

[0628] each C-R10is independently halogen, cyano, nitro, Ci-Cs alkyl, C1-C8 haloalkyl, Ci-Cs alkoxy, or Ci-C 8 haloalkoxy;

[0629] or a salt or N-oxide thereof.

[0630] In some embodiments, the compound is defined by Formula VIIA or a salt thereofAttorney Docket No. 10620-164W02

[0631] NCSURef.: 2025-138-04

[0632]

[0633] Formula VII A

[0634] wherein

[0635] Y is chosen from S, S=O, and S(=O)2;

[0636] C-Y1is C(C-R7)(C-R8) or C=O;

[0637] C-Y2, C-Y3and C-Y4are independently C(C-R7)(C-R8), C=O, N-(C-R9), O, S, SO, or SO2, wherein at least two adjacent ring atoms in the ring formed by C-Y1, C-Y2, C-Y3and C-Y4are heteroatoms;

[0638] C-G1is oxygen or sulfur;

[0639] C-R1is hydrogen, C1-C8 alkyl, C1-C8 alkylcarbonyl-, C1-C8 alkoxy, C1-C8 alkoxy-C1-C8 alkyl, or C1-C8 alkoxy carbonyl;

[0640] C-R2is hydrogen or C1-C4 alkyl;

[0641] C-R3is C1-C4 haloalkyl;

[0642] C-R4is phenyl, or phenyl substituted by one to three C-R6;

[0643] C-R5is halogen, nitro, C1-C4 alkyl, C3-C4 cycloalkyl, C2-C4 alkenyl or C1-C4 haloalkyl; C-A3and C-A4are independently C-H orN;

[0644] C-L is a bond or methylene;

[0645] each C-R7and C-R8is independently hydrogen, halogen, Ci-Cs alkyl, or C1-C8 haloalkyl; each C-R9is independently hydrogen, cyano, cyano-Ci-Cs alkyl, Ci-Cs alkyl, C1-C8 haloalkyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, or C3-C8 cycloalkyl-Ci-Cs alkyl, C3-C8 cycloalkyl-Ci-Cs alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, or Cs-Cscycloalkyl-Ci-Cshaloalkyl, Ci-Cs hydroxyalkyl, Ci-Csalkoxy-Ci-Cs alkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 alkynyl, C2-Cs haloalkynyl, phenyl, phenyl substituted by one to three C-R10, phenyl-Ci-C4 alkyl, phenyl-Ci-C4 alkyl wherein the phenyl moiety is substituted by one to three C-R10, 5-6 membered heteroaryl-Ci-C4 alkyl or 5-6 membered heteroaryl-Ci-C4 alkyl wherein the heteroaryl moiety is substituted by one to three C-R10, or Ci-C4alkyl-(Ci-C4alkyl-O-N=)C-CH2-;Attorney Docket No. 10620-164W02

[0646] NCSURef.: 2025-138-04

[0647] each C-R10is independently halogen, cyano, nitro, C1-C8 alkyl, C1-C8 haloalkyl, C1-C8 alkoxy, or C1-C8 haloalkoxy;

[0648] or a salt or N-oxide thereof.

[0649] In some embodiments, C-Y1is C(C-R7)(C-R8).

[0650] In some embodiments, two of C-Y2, C-Y3and C-Y4in the grouping -C-Y2-C-Y3-C-Y4-together are -S-S-, -S-SO-, -SO-SO-, -SO-SO2-, -SO2-SO2-, -O-N(-C-R9)-, -O-S-, -O-SO-, -O-SO2-, -N(-C-R9)-N(-C-R9)-, -N(-C-R9)-S-, -N(-C-R9)-S(O)- or -N(-C-R9)-SO2-.

[0651] In some embodiments, the grouping -C-Y2-C-Y3-C-Y4- is selected from -C(C-R7)(C-R8)-N(-C-R9)-N(-C-R9)-, -C(C-R7)(C-R8)-N(-C-R9)-O-, -C(C-R7)(C-R8)-N(-C-R9)-S-, -C(C-R7)(C-R8)-N(-C-R9)-SO2-, -C(C-R7)(C-R8)-O-N(-C-R9)-, -C(C-R7)(C-R8)-O-SO-, -C(C-R7)(C-R8)-O-SO2-, -C(C-R7)(C-R8)-S-N(-C-R9)-, -C(C-R7)(C-R8)-S-S-, -C(C-R7)(C-R8)-SO-O-, -C(C-R7)(C-R8)-SO2-N(-C-R9)-, -C(C-R7)(C-R8)-SO2-O-, -C(=O)-N(-C-R9)-N(-C-R9)-, -C(=O)-N(-C-R9)-O-, -C(=O)-N(-C-R9)-S-, -C(=O)-O-N(-C-R9)-, -C(=O)-S-N(-C-R9)-, -N(-C-R9)-N(-C-R9)-C(C-R7)(C-R8)-, -N(-C-R9)-N(-C-R9)-C(=O)-, -N(-C-R9)-O-C(C-R7)(C-R8)-, -N(-C-R9)-O-C(=O)-, -N(-C-R9)-S-C(C-R7)(C-R8)-, -N(-C-R9)-SO-N(-C-R9)-, -N(-C-R9)-SO2-C(C-R7)(C-R8)-, -N(-C-R9)-SO2-N(-C-R9)-, -N(-C-R9)-SO2-O-, -O-N(-C-R9)-C(C-R7)(C-R8)-, -O-N(-C-R9)-C(=O)-, -O-N(-C-R9)-SO-, -O-N(-C-R9)-SO2-, -N(-C-R9)-S-C(C-R7)(C-R8)-, -N(-C-R9)-SO-C(C-R7)(C-R8)-, -N(-C-R9)-SO-N(-C-R9)-, -N(-C-R9)-SO-O-, -N(-C-R9)-SO2-C(C-R7)(C-R8)-, -N(-C-R9)-SO2-N(-C-R9)-, -N(-C-R9)-SO2-O-, -S-N(-C-R9)-C(C-R7)(C-R8)-, -S-N(-C-R9)-C(=O)-, -S-S-C(C-R7)(C-R8)-, -SO-N(-C-R9)-N(-C-R9)-, -SO-O-C(C-R7)(C-R8)-, -SO2-N(-C-R9)-C(C-R7)(C-R8)-, -SO2-N(-C-R9)-N(-C-R9)-, -SO2-N(-C-R9)-O- and -SO2-O-C(C-R7)(C-R8)-.

[0652] In some embodiments, C-Y2or C-Y4is C=O.

[0653] In some embodiments, C-Y2or C-Y4is C(C-R7)(C-R8).

[0654] In some embodiments, C-Y2and C-Y4are independently N(-C-R9), O, S, SO, or SO2. In some embodiments, C-Y4is C=O or C(C-R7)(C-R8) when C-L is a bond.

[0655] In some embodiments, the grouping -C-Y2-C-Y3-C-Y4- is selected from -O-N(-C-R9)-C(=O)-, -S-S-C(C-R7)(C-R8)-, -S-SO-C(C-R7)(C-R8)-, -O-N(-C-R9)-(C-R7)(C-R8)-, -N(-C-R9)-N(-C-R9)-C(=O)-, -SO2-N(-C-R9)-C(C-R7)(C-R8)-,

[0656] -C(C-R7)(C-R8)-N(-C-R9)-O-, -C(C-R7)(C-R8)-N(-C-R9)-O-, -C(=O)-N(-C-R9)-O-, -C(=O)-N(-C-R9)-O-, -O-SO-O-, -C(C-R7)(C-R8)-N(-C-R9)-SO2, -N(-C-R9)-SO2-O-, -SO-O-C(C-R7)(C-R8)-and -N(C-R9)-SO-O-.

[0657] In some embodiments, the grouping -C-Y2-C-Y3-C-Y4- is selected from -O-N(-C-R9)-C(=O)-, -S-S-C(C-R7)(C-R8)-, -SO2-N(-C-R9)-C(C-R7)(C-R8)-, -C(C-R7)(C-R8)-N(-C-R9)-O-, -C(=O)-N(-C-R9)-O-, -SO-O-C(C-R7)(C-R8)- and -C(=O)-N(-C-R9)-O-.

[0658]

[0659] Attorney Docket No. 10620-164W02

[0660] NCSURef.: 2025-138-04

[0661] In some embodiments, the grouping -C-Y2-C-Y3-C-Y4- is -O-N(-C-R9)-C(=O)- or -SO-O-C(C-R7)(C-R8)-.

[0662] In some embodiments, C-R9is hydrogen, cyano- Ci-Cs alkyl, Ci-Cs alkyl, Cs-Cs cycloalkyl, Cs-Cs cycloalkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, or Ci-Cshaloalkyl, Ci-Cshydroxyalkyl, C2-C8 alkenyl, C2-CS alkynyl, phenyl-Ci-C4 alkyl or phenyl-Ci-C4 alkyl wherein the phenyl moiety is substituted by one to three C-R10, 5-6 membered heteroaryl-Ci-C4 alkyl or 5-6 membered heteroaryl-Ci-C4 alkyl wherein the heteroaryl moiety is substituted by one to three C-R10, and wherein the heteroaryl is pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl or thiazolyl.

[0663] In some embodiments, the compound is one of the following:

[0664] o

[0665] MeO

[0666]

[0667] Attorney Docket No. 10620-164W02

[0668] NCSURef.: 2025-138-04

[0669]

[0670] where Y is chosen from S, S=O, and S(=O)2.

[0671] In some examples, the 1,4,2-oxathiazole analogs of isocy closeram can be the compound shown below

[0672]

[0673] wherein Y is chosen from S, S=O, and S(=O)2.

[0674] In some examples, the isocy closeram analog can be the compound shown below.

[0675]

[0676] Attorney Docket No. 10620-164W02

[0677] NCSURef.: 2025-138-04

[0678] 1.4.2-()xathiazole Analogs of Icafolin

[0679] In some examples, described herein are 1,4,2-oxathiazole analogs of icafolin. Icafolin and related compounds are described for example in U. S. Patent No. 11,597,724 and International Publication No. WO2018 / 228985, each of which is incorporated by reference in its entirety. Described herein are analogs of these compounds which include a 1,4,2-oxathiazole ring.

[0680] For example, described herein are compound defined by Formula XII

[0681]

[0682] Formula XII

[0683] and / or a salt thereof wherein

[0684] Y is chosen from S, S=O, and S(=O)2;

[0685] H-R3represents (Ci-C4)-alkyl, (C3-Cs)-cycloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or (Ci-C4)-alkoxy, each of which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, (Ci-C4)-alkoxy and hydroxy;

[0686] H-R4represents hydrogen, or represents (Ci-Ci2)-alkyl, (C3-C7)-cycloalkyl, (C3-C7)-cycloalkyl-(Ci-C8)-alkyl, (C2-Ce)-alkenyl, (Cs-C6)-cycloalkenyl or (C2-Cs)-alkynyl, each of which is substituted by m radicals from the group consisting of halogen, cyano, (Ci-Ce)-alkoxy, hydroxy and aryl;

[0687] H-Y represents oxygen or sulfur;

[0688] H-W represents oxygen or sulfur;

[0689] H-Z represents a fully saturated or partially saturated furan ring which is substituted by k radicals from R5,

[0690]

[0691] Attorney Docket No. 10620-164W02

[0692] NCSURef.: 2025-138-04

[0693] where the arrow denotes a bond to the group C=(H-W) of Formula XII and R5represents fluorine, chlorine, cyano or CCh(H-R7), or represents (Ci-C2)-alkyl or (Ci-C2)-alkoxy, each of which is substituted by m radicals from the group consisting of fluorine and chlorine;

[0694] H-X2, H-X4and H-X6independently of one another each represent hydrogen, fluorine, chlorine, bromine or cyano, or represent (Ci-C2)-alkyl, in each case substituted by m radicals from the group consisting of fluorine, chlorine, bromine and (Ci-C2)-alkoxy;

[0695] H-X3and H-X5independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, nitro, S(O)n(H-R6) or CO2(H-R7), or represent (Ci-C3)-alkyl, (Ci-C3)-alkoxy, (C3-C4)-cycloalkyl, (C2-C3)-alkenyl or (C2-C3)-alkynyl, each of which is substituted by m radicals from the group consisting of fluorine, chlorine and bromine;

[0696] H-R6represents (Ci-C2)-alkyl or (C3-C4)-cycloalkyl, each of which is substituted by m radicals from the group consisting of fluorine and chlorine;

[0697] H-R7represents hydrogen, or represents (Ci-C3)-alkyl or (C3-Cs)-cycloalkyl, each of which is substituted by m radicals from the group consisting of fluorine, chlorine and (C1-C2)-alkoxy;

[0698] k represents 0, 1 or 2;

[0699] m represents 0, 1, 2, 3, 4 or 5; and

[0700] n represents 0, 1 or 2.

[0701] In some embodiments, H-R3represents (Ci-C3)-alkyl, (C3-C4)-cycloalkyl, (C2-C3)-alkenyl, (C2-C3)-alkynyl or (Ci-Cs)-alkoxy, each of which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, (Ci-C2)-alkoxy and hydroxy.

[0702] In some embodiments, H-R4represents hydrogen, or represents (Ci-Ce)-alkyl, (Cs-Ce)-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-C6)-alkyl, (C2-Ce)-alkenyl, (Cs-C6)-cycloalkenyl or (C2-C6)-alkynyl, each of which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, (Ci-C4)-alkoxy, hydroxy and aryl.

[0703] In some embodiments, each of H-Y and H-W represents oxygen.

[0704] In some embodiments, H-Z represents a group chosen from H-Z-l to H-Z-33:Attorney Docket No. 10620-164W02

[0705] NCSURef.: 2025-138-04

[0706] H-Z-1 H-Z-2 H-Z-3 H-Z-4 H-Z-5 H-Z-6 H-Z-7 H-Z-8

[0707] H-Z-10 H-Z-11 H-Z-12 H-Z-13 H-Z-14 H-Z-15

[0708] W 'b CM H-Z-17 H-Z-18 H-Z-19 H-Z-20 H-Z-21 H-Z-22 H-Z-23 H-Z-24 H-Z-25

[0709]

[0710] H-Z-26 H-Z-27 H-Z-28 H-Z-29 H-Z-30 H-Z-31 H-Z-32 H-Z-33 where the bond line in each case denotes a bond to the group C=(H-W) of Formula XII.

[0711] In some embodiments, R5represents fluorine, chlorine, cyano, CO2H, CO2CH3 or CO2CH2CH3, or represents (Ci-C2)-alkyl or (Ci-C2)-alkoxy, each of which is substituted by m radicals from the group consisting of fluorine and chlorine.

[0712] In some embodiments, H-X2, H-X4and H-X6independently of one another each represent hydrogen, fluorine, chlorine, bromine or cyano, or represent methyl or methoxy, each of which is substituted by m radicals from the group consisting of fluorine and chlorine.

[0713] In some embodiments, H-X3and H-X5independently of one another each represent hydrogen, fluorine, chlorine, bromine, hydroxy or cyano, or represent (Ci-C3)-alkyl, (C1-C3)-alkoxy, (C3-C4)-cycloalkyl, (C2-C3)-alkenyl or (C2-C3)-alkynyl, each of which is substituted by m radicals from the group consisting of fluorine, chlorine and bromine.

[0714] In some embodiments, H-R7represents hydrogen, or represents (Ci-C3)-alkyl each substituted by m radicals from the group consisting of fluorine and chlorine.

[0715] In some embodiments, m is 0, 1, 2 or 3.

[0716] In some embodiments, Y is chosen from S, S=O, and S(=O)2;Attorney Docket No. 10620-164W02

[0717] NCSURef.: 2025-138-04

[0718] H-R3represents (Ci-C3)-alkyl, (C3-C4)-cycloalkyl, (C2-Cs)-alkenyl, (C2-C3)-alkynyl or (Ci-C3)-alkoxy, each of which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, (Ci-C2)-alkoxy and hydroxy;

[0719] H-R4represents hydrogen, or represents (Ci-Ce)-alkyl, (C3-Ce)-cycloalkyl, (Cs-Ce)-cycloalkyl-(Ci-C6)-alkyl, (C2-Ce)-alkenyl, (Cs-C6)-cycloalkenyl or (C2-Ce)-alkynyl, each of which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, (Ci-C4)-alkoxy, hydroxy and aryl;

[0720] H-Y represents oxygen;

[0721] H-W represents oxygen;

[0722] H-Z represents a group Z-l to Z-4:

[0723]

[0724] H-Z-1 H-Z-2 H-Z-3 H-Z-4

[0725] where the bond line in each case denotes a bond to the group C=W of the formula (I):

[0726] H-X2, H-X4and H-X6independently of one another represent hydrogen or fluorine;

[0727] H-X3and H-X5independently of one another represent hydrogen, fluorine, chlorine, bromine, hydroxy or cyano, or represent (Ci-C3)-alkyl, (Ci-C3)-alkoxy, (C3-C4)-cycloalkyl, (C2-C3)-alkenyl or (C2-C?)-alkyny I. each of which is substituted by m radicals from the group consisting of fluorine, chlorine and bromine; and

[0728] m represents 0, 1, 2 or 3

[0729] In some embodiments, the compound can comprise a compound defined by the formula below

[0730] o

[0731] N

[0732] (H-W)

[0733]

[0734] where

[0735] Y is chosen from S, S=O, and S(=O)2;

[0736] H-Ai and H-A2 are independently selected from hydrogen, methyl, fluoro, chloro, bromo, methoxy, trifluoromethyl; andAttorney Docket No. 10620-164W02

[0737] NCSU Ref.: 2025-138-04

[0738] (H-Z) O.

[0739]

[0740] (H-W) is chosen from one of the following:

[0741] •<H-ZY°'H y

[0742] IT

[0743] V

[0744] y ^ <H-Z=Y°'H(H-ZV'CH3 V

[0745] X / ^ fCH I3

[0746] y

[0747] y ^

[0748] V ^

[0749]

[0750] Attorney Docket No. 10620-164W02

[0751] NCSU Ref.: 2025-138-04

[0752] (H-Z5)

[0753] y y

[0754] V^ ^

[0755] ^ A

[0756] , Hy ^ Ar ^

[0757] VH-ZV'CH3

[0758] FL CH3V

[0759] y

[0760]

[0761] Attorney Docket No. 10620-164W02

[0762] NCSURef.: 2025-138-04 y V0'CH3

[0763] •CH3v o v

[0764] y

[0765] , H-Z«V'H V

[0766] V Sr°- *CH3

[0767] Sr0-

[0768] ^

[0769] V

[0770]

[0771] Attorney Docket No. 10620-164W02

[0772] NCSU Ref.: 2025-138-04

[0773] Y

[0774] ^

[0775] T

[0776] < H-Z13)^

[0777] y TT T-Me

[0778] V

[0779] ^ ^ o(H-Z-Y0%H y ^ y ^

[0780] I oT y V

[0781] ^ Y o°' y^cN o ^ y ^

[0782]

[0783] Attorney Docket No. 10620-164W02

[0784] NCSURef.: 2025-138-04

[0785] ^ VH-ZIV'CH3 o o ^ T

[0786] TT ° o and H-Z represents a group chosen from H-Z-1 to H-Z-17: Y 'V'V'W xW Y OMe

[0787] H-Z-1 H-Z-2 H-Z-3 H-Z-4 H-Z-5 H-Z-6 H-Z-7 H-Z-8

[0788] CH3“O' •CH3\ O

[0789] H-Z-9 H-Z-10 H-Z-11 H-Z-12 H-Z-13 H-Z-14 H-Z-15H‘Z-16

[0790]

[0791] H-Z-17

[0792] where the bond line in each case denotes a bond to the group C=(H-W).

[0793] Analogous compounds can also be prepared where H-Z-1 to H-Z-17 are instead H-Z-18 to H-Z-33, as shown below.

[0794] H-Z-18 H-Z-19 H-Z-20 H-Z-21 H-Z-22 H-Z-23 H-Z-24 H-Z-25

[0795]

[0796] H-Z-26 H-Z-27 H-Z-28 H-Z-29 H-Z-30 H-Z-31 H-Z-32 H-Z-33

[0797] In some embodiments, the compound can comprise a compound defined by the formula belowAttorney Docket No. 10620-164W02

[0798] NCSURef.: 2025-138-04

[0799] (H-R4)

[0800]

[0801] where

[0802] Y is chosen from S, S=O, and S(=O)2;

[0803] H-Ai and H-A2 are independently selected from hydrogen, methyl, fluoro, chloro, bromo, methoxy, trifluoromethyl; and

[0804]

[0805] V (H’Z)'|fO'K(H -R4)

[0806] (H-W) js chosen from one of the following:

[0807] o

[0808]

[0809] o and H-Z represents a group chosen from H-Z-l to H-Z-33:Attorney Docket No. 10620-164W02

[0810] NCSURef.: 2025-138-04

[0811] 'U 'V y H-Z-1 H-Z-2 H-Z-3 H-Z-4 H-Z-5 H-Z-6 H-Z-7 H-Z-8 V\X- V V^O^CH3 VC^

[0812] H-Z 16 H-Z-9 H-Z-10 H-Z-11 H-Z-12 H-Z-13 H-Z-14 H-Z-15

[0813] --^P VP" V^ '"^P '"^P" / 'V" H-Z-17 H-Z-18 H-Z-19 H-Z-20 H-Z-21 H-Z-22 H-Z-23 H-Z-24 H-Z-25

[0814]

[0815] H-Z-26 H-Z-27 H-Z-28 H-Z-29 H-Z-30 H-Z-31 H-Z-32 H-Z-33 where the bond line in each case denotes a bond to the group C=(H-W).

[0816] In some embodiments, the compound comprises one of the following where Y is chosen from S, S=O, and S(=O)2.

[0817] JL

[0818] 7?°^ V

[0819]

[0820] Attorney Docket No. 10620-164W02

[0821] NCSURef.: 2025-138-04

[0822] In some embodiments, the compound comprises one of the following

[0823]

[0824] where Y is chosen from S, S=O, and S(=O)2; W represents oxygen; Z represents one of the followingAttorney Docket No. 10620-164W02

[0825] NCSURef.: 2025-138-04

[0826]

[0827] In some examples, the 1,4,2-oxathiazole analogs of icafolin can be the compound shown below

[0828]

[0829] wherein Y is chosen from S, S=O, and S(=O)2.

[0830] In some examples, the icafolin analog can be the compound shown below.Attorney Docket No. 10620-164W02

[0831] NCSURef.: 2025-138-04

[0832]

[0833] 1.4.2-()xathiazole Analogs of Sarolaner

[0834] In some examples, described herein are 1,4,2-oxathiazole analogs of sarolaner. Sarolaner and related compounds are described for example in U. S. Patent No. 9,226,928, which is incorporated by reference in its entirety. Described herein are analogs of these compounds which include a 1,4,2-oxathiazole ring or an oxidized analog thereof.

[0835] For example, described herein are compounds defined by Formula XI

[0836]

[0837] Formula XI

[0838] wherein

[0839] Y is chosen from S, S=O, and S(=O)2

[0840] G-Rla, G-Rlb, and G-Rlcare each independently hydrogen, halo, hydroxyl, cyano, nitro, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-Cealkoxy, Co-CsalkylCs-Ce cycloalkyl, Ci-Cehaloalkoxy, — C(O)NH2, — SFS, or— S(O)p(G-R);

[0841] G-R2is fluoro, chloro, or Ci-Cealkyl;

[0842] G-R3is cyano, Ci-Cealkyl, Ci-Cehaloalkyl, — C(O)NRaRb, C2-Cealkenyl, C2-Cealkynyl, C2-Cehaloalkenyl, or C2-Cehaloalkynyl;

[0843] G-R4is hydrogen, Ci-Cealkyl, C2-Cealkenyl, Co-CealkylCs-Cecycloalkyl, Co-Cealkylphenyl, Co-Cealkylheteroaryl, or Co-Cealkylheterocycle;

[0844] R5is hydrogen, Ci-Cealkyl, hydroxyl, cyano, nitro, — S(O)PRC, or Ci-Cealkoxy;Attorney Docket No. 10620-164W02

[0845] NCSURef.: 2025-138-04

[0846] G-R is Ci-Cealkyl or Cs-Cecycloalkyl optionally substituted with at least one halo substituent;

[0847] Rais hydrogen, Ci-Cealkyl, or Co-CsalkylCs-Cecycloalkyl; wherein the alkyl and alkylcycloalkyl is optionally substituted by cyano or at least one halo substituent;

[0848] Rbis hydrogen, Ci-Cealkyl, Cs-Cecycloalkyl, Co-Csalkylphenyl, Co-Csalkylheteroaryl, or Co-Csalkylheterocycle, each optionally substituted, where chemically possible, with at least one substituent selected from hydroxyl, cyano, halo, or — S(O)P(G-R);

[0849] Rcis Ci-Cealkyl, Ci-Cehaloalkyl, Ci-CehaloalkylCs-Cecycloalkyl, Co-CsalkylCs-Cecycloalkyl, Co-Csalkylphenyl, Co-Csalkylheteroaryl, or Co-Csalkylheterocycle each optionally substituted with at least one substituent selected from cyano, halo, hydroxyl, oxo, Ci-Cealkoxy, Ci-Cehaloalkoxy, Ci-Cehaloalkyl, — S(O)P(G-R), — SH, — S(O)PNRaRb, — NRaRb, — NRaC(O)Rb, — SC(O)(G-R), — SCN, or — C(O)NRaRb;

[0850] when G-R4is Ci-Cealkyl or Co-CealkylCs-Cecycloalkyl, then each moiety can be optionally substituted by at least one substituent selected from cyano, halo, hydroxyl, oxo, Ci-Cealkoxy, Ci-Cehaloalkoxy, Ci-Cehaloalkyl, Ci-Cealkyl, hydroxylCi-Cealkyl-, — S(O)PRC, — SH, — S(O)PNRaRb, — NRaRb, — NRaC(O)Rb, — SC(O)(G-R), —SCN, or — C(O)NRaRb;

[0851] when G-R4is Co-Cealkylphenyl, Co-Cealkylheteroaryl, or Co-Cealkylheterocycle, then each moiety can be further optionally substituted with at least one substituent selected from cyano, halo, oxo, =S, =N(G-R5), hydroxylCi-Cealkyl-, hydroxyl, Ci-Cealkoxy, Ci-Cealkyl, Ci-Cehaloalkyl, — SH, — S(O)P(G-R), and Ci-Cehaloalkoxy;

[0852] n is the integer 0, 1, or 2, and when n is 2, each G-R2may be identical or different from each other; and

[0853] p is the integer 0, 1, or 2;

[0854] stereoisomers thereof, or a salt thereof.

[0855] In some embodiments, the comprises one of the following

[0856]

[0857] wherein Y is chosen from S, S=O, and S(=O)2Attorney Docket No. 10620-164W02

[0858] NCSURef.: 2025-138-04

[0859] In some embodiments, the compound comprises the S-isomer of a compound of Formula XI, such as the compound shown above.

[0860] In some embodiments, the compound comprises a compound shown below, wherein Y is

[0861]

[0862] Attorney Docket No. 10620-164W02

[0863] NCSURef.: 2025-138-04

[0864]

[0865] Attorney Docket No. 10620-164W02

[0866] NCSURef.: 2025-138-04

[0867]

[0868] In some examples, the 1,4,2-oxathiazole analogs of sarolaner can be the compound shown below

[0869] w

[0870]

[0871] o 6' Me

[0872] wherein Y is chosen from S, S=O, and S(=O)2.

[0873] In some examples, the sarolaner analog can be the compound shown below.

[0874] w o o' Me

[0875]

[0876] Attorney Docket No. 10620-164W02

[0877] NCSURef.: 2025-138-04 1.4.2-()xathiazole Analogs of Fluxametamide

[0878] In some examples, described herein are 1,4,2-oxathiazole analogs of fluxametamide. For example, described herein are analogs of fluxametamide which include a 1,4,2-oxathiazole ring or an oxidized analog thereof.

[0879] In some examples, the 1,4,2-oxathiazole analogs of fluxametamide can be the compound shown below

[0880]

[0881] wherein Y is chosen from S, S=O, and S(=O)2.

[0882] In some examples, described herein are 1,4,2-oxathiazole analogs of fluxametamide, such as the compound described below.

[0883] Cl

[0884]

[0885] Method of Making

[0886] The 1,4,2-oxathiazoles and oxidized analogs thereof can be prepared by methods that comprise contacting a thiohydroximic acid defined by Formula II below

[0887] HO N R3

[0888]

[0889] Formula II

[0890] or a salt or ester thereof, wherein R1is chosen from alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, hetercycloalkyl, alkylcycloalkyl, alkylhetercycloalkyl, aryl,Attorney Docket No. 10620-164W02

[0891] NCSURef.: 2025-138-04

[0892] heteroaryl, alkylaryl, alkylheteroaryl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylaminocarbonyl, heteroalkylaminocarbonyl, dialkylaminocarbonyl, and heterodialkylaminocarbonyl, each optionally substituted with one or more substituents individually chosen from RA; R2is chosen from alkenyl, alkynyl, cycloalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxy carbonyl, haloalkoxycarbonyl, thioalkylcarbonyl, alkylaminocarbonyl, heteroalkylaminocarbonyl, dialkylaminocarbonyl, heterodialkylaminocarbonyl, thioamido, aryl, and heteroaryl, each optionally substituted with one or more substituents individually chosen from RA; R3is chosen from hydrogen, alkyl, and haloalkyl, wherein the alkyl and haloalkyl groups are optionally substituted with one or more substituents individually chosen from RA; and RAis chosen from hydroxy, halogen, -CN, -NO2, amino, alkylamino, dialkylamino, alkyl, haloalkyl; alkylthio; haloalkylthio; alkoxy, haloalkoxy, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxy carbonyl, haloalkoxy carbonyl, alkylaminocarbonyl, heteroalkylaminocarbonyl, dialkylaminocarbonyl, heterodialkylaminocarbonyl, nitrone, sulfonic acid, sulfonamido, thiol, phosphonate, phosphinyl, aldehyde, trimethylsilyl, hydrazino, azido, isocyanate, aryl, and heteroaryl; with a heterogeneous catalyst under conditions effective to form a 1,4,2-oxathiazole defined by Formula I below

[0893]

[0894] Formula I

[0895] or a salt or ester thereof, wherein R1is chosen from alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, hetercycloalkyl, alkylcycloalkyl, alkylhetercycloalkyl, aryl, heteroaryl, alkylaryl, alkylheteroaryl, alkylcarbonyl, haloalkylcarbonyl, alkoxy carbonyl, haloalkoxycarbonyl, alkylaminocarbonyl, heteroalkylaminocarbonyl, dialkylaminocarbonyl, and heterodialkylaminocarbonyl, each optionally substituted with one or more substituents individually chosen from RA; R2is chosen from alkenyl, alkynyl, cycloalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxy carbonyl, haloalkoxycarbonyl, thioalkylcarbonyl, alkylaminocarbonyl, heteroalkylaminocarbonyl, dialkylaminocarbonyl, heterodialkylaminocarbonyl, thioamido, aryl, and heteroaryl, each optionally substituted with one or more substituents individually chosen from RA; R3is chosen from hydrogen, alkyl, and haloalkyl, wherein the alkyl and haloalkyl groups are optionally substituted with one or more substituents individually chosen from RA; and RAis chosen from hydroxy, halogen, -CN, -NO2, amino, alkylamino, dialkylamino, alkyl,Attorney Docket No. 10620-164W02

[0896] NCSURef.: 2025-138-04

[0897] haloalkyl; alkylthio; haloalkylthio; alkoxy, haloalkoxy, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxy carbonyl, haloalkoxy carbonyl, alkylaminocarbonyl, heteroalkylaminocarbonyl, dialkylaminocarbonyl, heterodialkylaminocarbonyl, nitrone, sulfonic acid, sulfonamido, thiol, phosphonate, phosphinyl, aldehyde, trimethylsilyl, hydrazino, azido, isocyanate, aryl, and heteroaryl and optionally oxidizing the 1,4,2-oxathiazole defined by Formula I to generate a sulfoxide or sulfone analog of the 1,4,2-oxathiazoles defined by Formula I defined by Formula I.

[0898] In some embodiments, contacting the thiohydroximic acid defined by Formula II with the heterogeneous catalyst comprises flowing the thiohydroximic acid defined by Formula II over or through a stationary phase comprising the heterogeneous catalyst. In some examples, the stationary phase can be composed solely of a heterogeneous catalyst (e.g., MnO2powder) for example packaged in a cartridge or disposed in a fixed bed or column. In other examples, the stationary phase can comprise an inert filler and the heterogeneous catalyst. The inert filler can be, for example, a non-porous or a porous solid or filtering aid agent, such as Celite®, bentonite, talc, sand, sodium sulfate, diatomaceous earth, CaO, CaCO3, chalk, MgSO4, clay, silica gel, or combinations thereof.

[0899] In certain embodiments, the cyclization of the starting material (SM) defined by Formula II can be performed under continuous flow conditions using a heterogeneous oxidant catalyst, wherein the catalyst is optionally combined with one or more inert filler materials. The incorporation of such fillers can improve flow characteristics within the packed column by reducing back pressure, enhancing permeability, and enabling more uniform distribution of the reaction mixture across the catalytic bed. In some embodiments, the presence of an inert filler further enables operation under simplified conditions, including manual pushing of the reaction mixture through the column (e.g., via syringe or gravity-assisted flow), thereby reducing or eliminating the need for automated pumping systems.

[0900] The inert filler may be selected from materials that are chemically compatible with the reaction conditions and do not substantially interfere with the oxidation or cyclization process. Suitable fillers include, but are not limited to, celite, sand, diatomaceous earth, silica gel, montmorillonite, alumina, and inorganic salts such as sodium sulfate, calcium carbonate, and sodium chloride, as well as desiccants such as molecular sieves. In certain embodiments, the filler material may also serve secondary roles, such as moisture control, dispersion of the oxidant, or stabilization of reactive intermediates.Attorney Docket No. 10620-164W02

[0901] NCSURef.: 2025-138-04

[0902] In some embodiments, the heterogeneous oxidant is physically mixed or co-packed with the inert filler within the stationary phase. The proportion of filler relative to the oxidant can vary depending on the desired flow properties and reactivity profile. For example, the filler may be present in an amount ranging from about 2% to about 90% by weight relative to the total packed material. In certain embodiments, the filler is present in an amount of from about 5% to about 50%, and in more preferred embodiments from about 5% to about 30%. Adjustment of the filler ratio can allow fine-tuning of parameters such as residence time, pressure drop across the column, and effective contact between the SM and the oxidant.

[0903] In particular implementations, lower filler loadings may favor higher catalytic density and shorter reaction times, whereas higher filler loadings may facilitate improved flow, reduced clogging, and scalability of the process. The optimal balance between oxidant and filler can be determined empirically based on the nature of the SM, the oxidant employed, solvent system, and desired throughput

[0904] In certain embodiments, flowing the thiohydroximic acid defined by Formula II over or through a stationary phase comprising the heterogeneous catalyst comprises flowing a solution of the thiohydroximic acid defined by Formula II over or through a stationary phase comprising the heterogeneous catalyst at a flow rate of from 0.1 mL / min to 1 L / min. In certain embodiments, the thiohydroximic acid defined by Formula II exhibits a residence time with the heterogeneous catalyst of from 5 minutes to 4 hours, such as from 5 minutes to 2 hours.

[0905] The flow rate can be varied from 10 mL / h to 90 mL / h when using a laboratory syringe pump. Further scaling of the reaction (e.g., larger pumps, larger volumes of stationary phase) will necessarily increase the flowrate). In some embodiments, the reaction can be performed with a flowrate / (column volume) ratio ranging from 1.5 to 25, and up to 50 when using a concentration of 0.014 M of the thiohydroximic acid defined by Formula II. The concentration can be increased from 14 mM to 3.0 M, yet optimal concentration could even be determined or limited by the starting material’s own solubility in the carrier solvent.

[0906] In some embodiments, the heterogeneous catalyst comprises an oxidant. Oxidants used for benzylic position oxidations are suitable for this cyclization, and the optimal catalyst for a particular cyclization is determined by the chemical compatibility or chemical stability of the starting material being used. Examples of suitable catalysts include, for example, potassium permanganate, chromium dichromate, chromium chromate, chromic acid, hydrogen peroxide, oxone, peracetic acid, and mCPBA. In certain embodiments, the heterogeneous catalyst comprises a metal oxide, such as manganese oxide.Attorney Docket No. 10620-164W02

[0907] NCSURef.: 2025-138-04

[0908] In some embodiments, the thiohydroximic acid defined by Formula II is contacted with the heterogeneous catalyst at a temperature of from 0 °C to 50 °C, such as from 15 °C to 50 °C or from 15 °C to 30 °C. However, the temperature can be as high as the boiling point of a carrier solvent in which the reaction is performed. In the examples below, reactions were performed in dichloromethane. However, other organic non-protic solvents such as THF, Methyl-THF, DCE, ethyl acetate, and ethyl acetate-heptanes are suitable.

[0909] In some embodiments, the method further comprises regenerating the heterogeneous catalyst.

[0910] Compositions and Methods of Use

[0911] In some embodiments, the 1,4,2-oxathiazoless provided herein are employed in mixtures containing an effective amount of the compound along with at least one agriculturally acceptable adjuvant or carrier. Exemplary adjuvants or carriers include those that are not phytotoxic or significantly phytotoxic to valuable crops, e.g., at the concentrations employed in applying the compositions for selective weed control in the presence of crops, and / or do not react or significantly react chemically with the compounds provided herein or other composition ingredients. Such mixtures can be designed for application directly to weeds or their locus or can be concentrates or formulations that are \diluted with additional carriers and adjuvants before application. They can be solids, such as, for example, dusts, granules, water dispersible granules, or wettable powders, or liquids, such as, and for example, emulsifiable concentrates, solutions, emulsions or suspensions. They can also be provided as a pre-mix or tank-mixed.

[0912] Suitable agricultural adjuvants and carriers that are useful in preparing the compositions described herein are well known to those skilled in the art. Some of these adjuvants include, but are not limited to, crop oil concentrate (mineral oil (85%) + emulsifiers (15%)); nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C9-C11 alkylpolyglycoside; phosphated alcohol ethoxylate; natural primary alcohol (C12-C16) ethoxylate; di -sec-butyl phenol EO-PO block copolymer; polysiloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate-99.

[0913] Liquid carriers that can be employed include water and organic solvents. The organic solvents typically used include, but are not limited to, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, com oil, cottonseed oil, linseedAttorney Docket No. 10620-164W02

[0914] NCSURef.: 2025-138-04

[0915] oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as 2-ethylhexyl stearate, n- butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono-, di- and poly-carboxylic acids and the like. Specific organic solvents include toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerine, A-methyl-2-pyrrolidinone, A. A-di meth l alkylamides, dimethyl sulfoxide, liquid fertilizers, and the like. In some embodiments, water is the carrier for the dilution of concentrates.

[0916] Suitable solid carriers include talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, and the like.

[0917] In some embodiments, one or more surface-active agents are utilized in the compositions of the present disclosure. Such surface-active agents are, in some embodiments, employed in both solid and liquid compositions, e.g., those designed to be diluted with carrier before application. The surface-active agents can be anionic, cationic or nonionic in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes. Surfactants conventionally used in the art of formulation and which may also be used in the present formulations are described, inter alia, in McCutcheon ’s Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood, New Jersey, 1998, and in Encyclopedia of Surfactants, Vol. I-III, Chemical Publishing Co., New York, 1980-81. Typical surface-active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-Cis ethoxylate; alcohol-alkylene oxide addition products, such as tri decyl alcohol-Ci6 ethoxylate; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; salts of mono- and dialkyl phosphate esters; vegetable or seed oils such as soybean oil, rapeseed / canola oil, olive oil, castor oil, sunflower seed oil, coconut oil, com oil,Attorney Docket No. 10620-164W02

[0918] NCSURef.: 2025-138-04

[0919] cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; and esters of the above vegetable oils, e.g., methyl esters.

[0920] Oftentimes, some of these materials, such as vegetable or seed oils and their esters, can be used interchangeably as an agricultural adjuvant, as a liquid carrier or as a surface active agent.

[0921] Other adjuvants commonly used in agricultural compositions include compatibilizing agents, antifoam agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, sticking agents, dispersing agents, thickening agents, freezing point depressants, antimicrobial agents, and the like. The compositions may also contain other compatible components, for example, other herbicides, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like.

[0922] The concentration of the active ingredients in the compositions of this disclosure is generally from about 0.001 to about 98 percent by weight. Concentrations from about 0.01 to about 90 percent by weight are often employed. In compositions designed to be employed as concentrates, the active ingredient is generally present in a concentration from about 5 to about 98 weight percent, preferably about 10 to about 90 weight percent. Such compositions are typically diluted with an inert carrier, such as water, before application. The diluted compositions usually applied to a crop, a fields, to weeds or the locus of weeds generally contain about 0.0001 to about 1 weight percent active ingredient and preferably contain about 0.001 to about 0.05 weight percent.

[0923] The present compositions can be applied to crops, a field, weeds or their locus by the use of conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation or flood water, and by other conventional means known to those skilled in the art.

[0924] In some embodiments, the compounds and compositions described herein are applied as a post-emergence application, pre-emergence application, in-water application to flooded paddy rice or water bodies (e.g., ponds, lakes and streams), or bum-down application.

[0925] In some embodiments, the compounds and compositions provided herein are utilized to control undesirable vegetation, insects, and / or fungus in crops, including but not limited to citrus, apple, rubber, oil, palm, forestry, direct-seeded, water-seeded and transplanted rice, wheat, barley, oats, rye, sorghum, com / maize, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, or row-crops, as well as non-crop settings, e.g., industrial vegetation management (IVM) or rights-of-way. In some embodiments, the compounds and compositions are used to control woody plants, broadleaf and grass weeds, or sedges.Attorney Docket No. 10620-164W02

[0926] NCSURef.: 2025-138-04

[0927] In some embodiments, the compounds and compositions provided herein are utilized to control undesirable vegetation, insects, and / or fungus in rice. In certain embodiments, the undesirable vegetation is Brachiaria platyphylla (Groseb.) Nash (broadleaf signalgrass, BRAPP), Digitaria sanguinalis (L.) Scop, (large crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (bamyardgrass, ECHCG), Echinochloa colonum (L.) LINK (junglerice, ECHCO), Echinochloa oryzoides (Ard.) Fritsch (early watergrass, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (late watergrass, ECHPH), Ischaemum rugosum Salisb. (saramollagrass, ISCRU), Leptochloa chinensis (L.) Nees (Chinese sprangletop, LEFCH), Leptochloa fascicularis (Lam.) Gray (bearded sprangletop, LEFFA), Leptochloa panicoides (Presl.) Hitchc. (Amazon sprangletop, LEFPA), Panicum dichotomiflorum (L.) Michx. (fall panicum, PANDI), Paspalum dilatatum Poir. (dallisgrass, PASDI), Cyperus difformis L. (smallflower flatsedge, CYPDI), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus iria L. (rice flatsedge, CYPIR), Cyperus rotundus L. (purple nutsedge, CYPRO), Eleocharis species (ELOSS), Fimbristylis miliacea (L.) Vahl (globe fringerush, FIMMI), Schoenoplectus juncoides Roxb. (Japanese bulrush, SPCJU), Schoenoplectus maritimus L. (sea clubrush, SCPMA), Schoenoplectus mucronatus L. (ricefield bulrush, SCPMU), Aeschynomene species, (jointvetch, AESSS), Alternanthera philoxeroides (Mart.) Griseb. (alligatorweed, ALRPH), Alisma plantago-aquatica L. (common waterplantain, ALSPA), Amaranthus species, (pigweeds and amaranths, AMASS), Ammannia coccinea Rottb. (redstem, AMMCO), Eclipta alba (L.) Hassk. (American false daisy, ECLAL), Heteranthera limosa (SW.) Willd. / V ahi (ducksalad, HETLI), Heteranthera reniformis R. & P. (roundleaf mudplantain, HETRE), Ipomoea hederacea (L.) Jacq. (ivyleaf morningglory, IPOHE), Lindernia dubia (L.) Pennell (low false pimpernel, LIDDU), Monochoria korsakowii Regel & Maack (monochoria, MOOKA), Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth, (monochoria, MOOVA), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Polygonum pensylvanicum L., (Pennsylvania smartweed, POLPY), Polygonum persicaria L. (ladysthumb, POLPE), Polygonum hydropiperoides Michx. (POLHP, mild smartweed), Rotala indica (Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species, (arrowhead, SAGSS), Sesbania exaltata (Raf.) Cory / Rydb. Ex Hill (hemp sesbania, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed, SPDZE).

[0928] In some embodiments, the compounds and compositions provided herein are utilized to control undesirable vegetation, insects, and / or fungus in cereals. In certain embodiments, the undesirable vegetation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Apera spica- venti (L.) Beauv. (windgrass, APESV), Avena fatua L. (wild oat, AVEFA), Bromus tectorum L. (downy brome, BROTE), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Phalaris minorAttorney Docket No. 10620-164W02

[0929] NCSURef.: 2025-138-04

[0930] Retz. (littleseed canarygrass, PHAMI), Poa annua L. (annual bluegrass, POANN), Setaria pumila (Poir.) Roemer & J. A. Schultes (yellow foxtail, SETLU), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR Galium aparine L. (catchweed bedstraw, GALAP), Kochia scoparia (L.) Schrad. (kochia, KCHSC), Lamium purpureum L. (purple deadnettle, LAMPU), Matricaria recutita L. (wild chamomile, MATCH), Matricaria matricarioides (Less.) Porter (pineappleweed, MATMT), Papaver rhoeas L.

[0931] (common poppy, PAPRH), Polygonum convolvulus L. (wild buckwheat, POLCO), Salsola tragus L. (Russian thistle, SASKR), Stellaria media (L.) Vill. (common chickweed, STEME), Veronica persica Poir. (Persian speedwell, VERPE), Viola arvensis Murr. (field violet, VIOAR), or Viola tricolor L. (wild violet, VIOTR).

[0932] In some embodiments, the compounds and compostions provided herein are utilized to control undesirable vegetation, insects, and / or fungus in range and pasture. In certain embodiments, the undesirable vegetation is Ambrosia artemisiifolia L. (common ragweed, AMBEL), Cassia obtusifolia (sickle pod, CASOB), Centaurea maculosa auct. non Lam.

[0933] (spotted knapweed, CENMA), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Convolvulus arvensis L. (field bindweed, CONAR), Euphorbia esula L. (leafy spurge, EPHES), Lactuca serriola L. / Tom. (prickly lettuce, LACSE), Plantago lanceolata L. (buckhom plantain, PLALA), Rumex obtusifolius L. (broadleaf dock, RUMOB), Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Sonchus arvensis L. (perennial sowthistle, SONAR), Solidago species (goldenrod, SOOSS), Taraxacum officinale G. H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Urtica dioica L. (common nettle, URTDI).

[0934] In some embodiments, the compounds and compositions provided herein are utilized to control undesirable vegetation, insects, and / or fungus found in row crops. In certain embodiments, the undesirable vegetation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Avena fatua L. (wild oat, AVEFA), Brachiaria platyphylla (Groseb.) Nash (broadleaf signalgrass, BRAPP), Digitaria sanguinalis (L.) Scop, (large crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (bamyardgrass, ECHCG), Echinochloa colonum (L.) Link (junglerice, ECHCO), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Panicum dichotomiflorum Michx. (fall panicum, PANDI), Panicum miliaceum L. (wild-proso millet, PANMI), Setaria faberi Herrm. (giant foxtail, SETFA), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sorghum halepense (L.) Pers. (Johnsongrass, SORHA), Sorghum bicolor (L.) Moench ssp. Arundinaceum (shattercane, SORVU), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus rotundus L. (purple nutsedge, CYPRO), Abutilon theophrasti Medik. (velvetleaf,Attorney Docket No. 10620-164W02

[0935] NCSURef.: 2025-138-04

[0936] ABUTH), Amaranthus species (pigweeds and amaranths, AMASS), Ambrosia artemisiifolia L. (common ragweed, AMBEL), Ambrosia psilostachya DC. (western ragweed, AMBPS), Ambrosia triflda L. (giant ragweed, AMBTR), Asclepias syriaca L. (common milkweed, ASCSY), Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Commelina benghalensis L. (tropical spiderwort, COMBE), Datura stramonium L. (jimsonweed, DATST), Daucus carota L. (wild carrot, DAUCA), Euphorbia heterophylla L. (wild poinsettia, EPHHL), Erigeron bonariensis L. (hairy fleabane, ERIBO), Erigeron canadensis L. (Canadian fleabane, ERICA), Helianthus annuus L. (common sunflower, HELAN), Jacquemontia tamnifolia (L.) Griseb. (smallflower momingglory, IAQTA), Ipomoea hederacea (L.) Jacq. (ivyleaf momingglory, IPOHE), Ipomoea lacunosa L. (white momingglory, IPOLA), Lactuca serriola L. / Tom. (prickly lettuce, LACSE), Portulaca oleracea L. (common purslane, POROL), Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Solanum ptychanthum Dunal (eastern black nightshade, SOLPT), o Xanthium strumarium L. (common cocklebur, XANST).

[0937] In some embodiments, application rates of about 1 to about 5,000 grams / hectare (g / ha) are employed in post-emergence operations. In some embodiments, rates of about 1 to about 5,000 g / ha are employed in pre-emergence operations.

[0938] In some embodiments, the compounds, compositions, and methods provided herein are used in conjunction with one or more other herbicides to control a wider variety of undesirable vegetation. When used in conjunction with other herbicides, the presently claimed compounds can be formulated with the other herbicide or herbicides, tank-mixed with the other herbicide or herbicides or applied sequentially with the other herbicide or herbicides. Some of the herbicides that can be employed in conjunction with the compounds of the present disclosure include: 4-CPA, 4-CPB, 4-CPP, 2,4-D, 2,4-D choline salt, 2,4-D esters and amines, 2,4-DB, 3,4-DA, 3,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DP, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprofos-methyl, amitrole, ammonium sulfamate, anilofos, anisuron, asulam, atraton, atrazine, azafenidin, azimsulfuron, aziprotryne, barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, benthiocarb, bentazon-sodium, benzadox, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, benzoylprop, benzthiazuron, bicyclopyrone, bifenox, bilanafos, bispyribac-sodium, borax, bromacil, bromobonil, bromobutide, bromofenoxim, bromoxynil, brompyrazon, butachlor, butafenacil, butamifos, butenachlor, buthidazole, buthiuron, butralin, butroxydim, buturon, butylate, cacodylic acid,Attorney Docket No. 10620-164W02

[0939] NCSURef.: 2025-138-04

[0940] cafenstrole, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole, chlorprocarb, carfentrazone-ethyl, CDEA, CEPC, chlomethoxyfen, chloramben, chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlomitrofen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, cisanilide, clethodim, cliodinate, clodinafop-propargyl, clofop, clomazone, clomeprop, cloprop, cloproxydim, clopyralid, cloransulam-methyl, CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumyluron, cyanatryn, cyanazine, cycloate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, cypromid, daimuron, dalapon, dazomet, delachlor, desmedipham, desmetryn, di-allate, dicamba, dichlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop-P, diclofop, diclosulam, diethamquat, diethatyl, difenopenten, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimexano, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, disul, dithiopyr, diuron, DMPA, DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon, esprocarb, ethalfluralin, ethbenzamide, ethametsulfuron, ethidimuron, ethiolate, ethobenzamid, etobenzamid, ethofumesate, ethoxyfen, ethoxy sulfuron, etinofen, etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop, fenoxaprop-P-ethyl, fenoxaprop-P-ethyl + isoxadifen-ethyl, fenoxasulfone, fenteracol, fenthiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenican, flufenpyr-ethyl, flumetsulam, flumezin, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fomesafen, foramsulfuron, fosamine, furyloxyfen, glufosinate, glufosinate-ammonium, glyphosate, halosafen, halosulfuron-methyl, haloxydine, haloxyfop-methyl, haloxyfop-P-methyl, halauxifen-methyl, hexachloroacetone, hexaflurate, hexazinone, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, indanofan, indaziflam, iodobonil, iodomethane, iodosulfuron, iofensulfuron, ioxynil, ipazine, ipfencarbazone, iprymidam, isocarbamid, isocil, isomethiozin, isonoruron, isopolinate, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, ketospiradox, lactofen, lenacil, linuron, MAA, MAMA, MCPA esters and amines, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifop, metamitron,Attorney Docket No. 10620-164W02

[0941] NCSURef.: 2025-138-04

[0942] metazachlor, metazosulfuron, metflurazon, methabenzthiazuron, methalpropalin, methazole, methiobencarb, methiozolin, methiuron, methometon, methoprotryne, methyl bromide, methyl isothiocyanate, methyldymron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide, napropamide-M, naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, ort / io-dichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraflufen-ethyl, parafluron, paraquat, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, phenobenzuron, phenylmercury acetate, picloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron-methyl, procyazine, prodiamine, profluazol, profluralin, profoxydim, proglinazine, prohexadione-calcium, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxy carbazone, propyrisulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron, proxan, prynachlor, pydanon, pyraclonil, pyraflufen, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor, pyridafol, pyridate, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac-methyl, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quinonamid, quizalofop, quizalofop-P-ethyl, rhodethanil, rimsulfuron, saflufenacil, S-metolachlor, sebuthylazine, secbumeton, sethoxydim, siduron, simazine, simeton, simetryn, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone, sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglycapin, swep, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn, tetrafluron, thenylchlor, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone-methyl, thifensulfuron, thiobencarb, tiocarbazil, tioclorim, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tricamba, triclopyr esters and amines, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac, tritosulfuron, vernolate and xylachlor.

[0943] The compounds and compositions of the present disclosure can generally be employed in combination with known herbicide safeners, such as benoxacor, benthiocarb, brassinolide, cloquintocet (e.g, mexyl), cyometrinil, daimuron, dichlormi d, dicyclonon, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, harpin proteins,Attorney Docket No. 10620-164W02

[0944] NCSURef.: 2025-138-04

[0945] isoxadifen-ethyl, mefenpyr-di ethyl, MG 191, MON 4660, naphthalic anhydride (NA), oxabetrinil, R29148 and / V-phenylsulfonylbenzoic acid amides, to enhance their selectivity.

[0946] The compounds, compositions, and methods described herein be used to control undesirable vegetation, insects, and / or fungus on glyphosate-tolerant-, glufosinate-tolerant-, dicamba-tolerant-, phenoxy auxin-tolerant-, pyridyloxy auxin-tolerant-, aryloxyphenoxypropionate-tolerant-, acetyl CoA carboxylase (ACCase) inhibitor-tolerant-, imidazolinone-tolerant-, acetolactate synthase (ALS) inhibitor-tolerant-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor -tolerant-, protoporphyrinogen oxidase (PPO) inhibitor -tolerant-, triazine-tolerant-, and bromoxynil-tolerant- crops (such as, but not limited to, soybean, cotton, canola / oilseed rape, rice, cereals, com, turf, etc), for example, in conjunction with glyphosate, glufosinate, dicamba, phenoxy auxins, pyridyloxy auxins, aryloxyphenoxypropionates, ACCase inhibitors, imidazolinones, ALS inhibitors, HPPD inhibitors, PPO inhibitors, triazines, and bromoxynil. The compositions and methods may be used in controlling undesirable vegetation in crops possessing multiple or stacked traits conferring tolerance to multiple chemistries and / or inhibitors of multiple modes-of-action. The compounds and compositions provided herein may also be employed to control herbicide resistant or tolerant weeds. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes resistant or tolerant to acetolactate synthase (ALS) inhibitors, photosystem II inhibitors, acetyl CoA carboxylase (ACCase) inhibitors, synthetic auxins, photosystem I inhibitors, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, microtubule assembly inhibitors, lipid synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid (VLCFA) inhibitors, phytoene desaturase (PDS) inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes-of-action such as quinclorac, and unclassified herbicides such as arylaminopropionic acids, difenzoquat, endothall, and organoarsenicals. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes with resistance or tolerance to multiple herbicides, multiple chemical classes, and multiple herbicide modes-of-action.

[0947] By way of non-limiting illustration, examples of certain embodiments of the present disclosure are given below.

[0948] EXAMPLESAttorney Docket No. 10620-164W02

[0949] NCSURef.: 2025-138-04

[0950] Example 1. Synthesis of 1,4,2-oxathiazole analogs of existing pesticides.

[0951] The methods described herein can be used to generate 1,4,2-oxathiazole analogs of existing pesticides, including analogs of insecticides in the isoxazoline class (e.g., 1,4,2-oxathiazole analogs of fluralaner, lotilaner, afoxolaner, sarolaner, fluxametamide, and isocycloseram).

[0952] Examples of 1,4,2-oxathiazole analogs of particular interest include the compounds shown below.

[0953]

[0954] Attorney Docket No. 10620-164W02

[0955] NCSURef.: 2025-138-04

[0956] Synthesis of Oxathiazole-Fluralaner Inspired Analogs

[0957] Isocyclosram and fluxametamide-inspired 1,4,2-oxathiazole examples

[0958]

[0959] Synthesis of methyl (E / Z)-4-((hydroxyimino)methyl)-2-methylbenzoate (AV-1195).

[0960] To a solution of aldehyde (3.0 g, 1 equiv.) in absolute EtOH (0.2 M) was added

[0961]

[0962] hydroxylamine HC1 (1.5 equiv.) and pyridine (3 equiv.) successively at R. T.

[0963] The reaction was allowed to stir overnight or until consumption of the SM, and monitored by TLC and / or LCMS. The reaction bulk of the EtOH was removed by rotovapAttorney Docket No. 10620-164W02

[0964] NCSURef.: 2025-138-04

[0965] and the residue was suspended in IN HC1. The aqueous layer was extracted with EtOAc (3X) and the combined organic layers were washed with brine (IX), dried over Na2SO4, filtered, and concentrated to yield the crude mixture of E / Z oximes as an off-white solid. Mixture was purified using flash chromatography. Desired product obtained as a white solid (3.12 g, quant.). m.p =137-138 C.1HNMR(700 MHz, DMSO) 8 11.51 (d, J = 0.7 Hz, 1H), 8.15 (s, 1H), 7.85 -7.81 (m, 1H), 7.54 - 7.51 (m, 2H), 3.82 (s, 3H), 2.52 (s, 3H).13C NMR (176 MHz, DMSO) 8 166.88, 147.29, 139.63, 136.43, 130.58, 129.60, 129.51, 123.67, 51.93, 20.99. LC-MS (ESI, APCI, m / z) 194 (M+H).

[0966] General Procedure A for the Synthesis of Thiohydroximic Acids.

[0967] To a 1 M solution of the benzaldehyde oxime derivative in dry dimethylformamide at 0 °C was added one-fifth of the total N-chlorosuccinimide, followed by portion-wise addition of the reagent over one hour. During this time, the reaction was allowed to warm slowly to room temperature and stir at this temperature for three hours. The reaction mixture was then diluted with diethyl ether to a concentration of 0.1 M and cooled back to 0 °C. Benzyl mercaptan was then added, followed by triethylamine, and the reaction was allowed to stir overnight while warming to room temperature. The reaction was quenched by the addition of saturated ammonium chloride and diluted with deionized water. The aqueous layer was extracted with ethyl acetate (3X). The combined organic fractions were washed with lithium chloride (5% w / v), water, brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude mixture was purified via flash chromatography to afford the desired product.

[0968] General Procedure B for the Synthesis of Thiohydroximic Acids.

[0969] To a 1 M solution of the benzaldehyde oxime derivative in dry dimethylformamide at 0 °C was added one-fifth of the total N-chlorosuccinimide, followed by portion-wise addition of the reagent over one hour. During this time, the reaction was allowed to warm slowly to room temperature and stir at this temperature for three hours. The mixture was poured on 10 volumes of ice and allowed to melt over time. Once all the ice has melted, the mixture was extracted with diethyl ether (3X). Combined organic layers were washed with lithium chloride (5% w / v), brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo and used crude for next reaction. The resulting chloroxime derivative was dissolved with diethyl ether (0.01-0.1 M) and cooled to 0 °C. Benzyl mercaptan was then added at this temperature, followed by triethylamine, and the reaction was allowed to stir overnight while warming to room temperature. The reaction was quenched by the addition of saturated ammonium chloride and diluted with deionized water. The aqueous layer was extracted with ethyl acetate (3X). The combined organic fractions wereAttorney Docket No. 10620-164W02

[0970] NCSURef.: 2025-138-04

[0971] washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude mixture was purified via flash chromatography to afford the desired product.

[0972] Synthesis of methyl (E / Z)-4-((hydroxyimino)((l-phenylethyl)thio)methyl)-2- 5 methylbenzoate (AV- 1233). The target compound was synthesized using N'UCH3

[0973] i dSO ^enera' Procedures A and / or B for the synthesis of thiohydroximic acids,

[0974]

[0975] o CH3Chloroxime of AV- 1221 (260 mg, 1 equiv), benzyl mercaptan (1 equiv.) and triethylamine (1 equiv.). Desired product was purified by flash chromatography, and obtained as a clear oil (190 mg, 56%). 'H-NMR (600 MHz, DMSO) 8 12.04 (s, 1H), 7.82 (d, J = 8.1 Hz, 1H), 7.37 (ddd, J = 8.1, 1.8, 0.7 Hz, 1H), 7.32 - 7.29 (m, 1H), 7.26 - 7.22 (m, 2H), 7.21 - 7.17 (m, 1H), 7.16 - 7.12 (m, 2H), 4.50 (q, J = 7.0 Hz, 1H), 3.84 (s, 3H), 2.50 (s, 3H), 1.45 (d, J = 7.0 Hz, 3H).13C-NMR(151 MHZ, DMSO) 8 166.89, 149.05, 142.68, 139.31, 138.04, 130.98, 130.19, 129.68, 128.30, 127.21, 127.02, 125.55, 52.00, 43.95, 22.78, 21.03. HRMS (ESI, m / z) calculated for C18H20NO3S, 330.11639 (M+H), found 330.11533.

[0976] General procedure for the preparation of 1,4,2-oxathiazoles: A 10-gram Biotage Sfar Silica silica column, all the silica was removed. 500 mg of celite was placed into the bottom of the container and compacted. In the same fashion, 12 grams of MnO2was placed on top of the celite and the system was closed using the same glass fiber frit the column contained originally. The Mn02 column was pressed using a Biotage dry load plunger until packed tightly. The vessel was conditioned by passing through 20 mL of dry di chloromethane. A 14 mM solution of the corresponding thiohydroximic derivative was then prepared in dry dichloromethane and loaded into a 20 mL syringe. A New Era Syringe Pump was fixed at 30 mL / hour, and the loaded syringe was passed through the column. After all the solution had been passed, an additional 45 mL was utilized to wash the container. The obtained solution was then concentrated in vacuo to afford the desired 1,4,2-oxathiazole derivative.

[0977] Synthesis of methyl 2-methyl-4-(5-methyl-5-phenyl-l,4,2-oxathiazol-3-yl)benzoate (AV-1257): The target compound was synthesized using General procedure for the preparation of 1,4,2-oxathiazoles. Thiohydroximic acid

[0978]

[0979] °CHsof AV-1233 (470 mg, 0.014 M). Desired product was obtained as a clear oil (285 mg, 61%). 'H NMR (600 MHz, CDC13) 87.92 (d, J = 8.0 Hz, 1H), 7.63 - 7.59 (m, 2H), 7.55 - 7.51 (m, 2H), 7.42 - 7.36 (m, 2H), 7.36 - 7.30 (m, 1H), 3.90 (s, 3H), 2.60 (s, 3H), 2.21 (s, 3H).13CNMR(151 MHZ, CDC13) 8 167.25, 156.14, 142.82, 140.77, 131.60, 131.45, 130.97, 130.91, 128.55, 128.43, 125.07, 124.87, 105.03, 52.05, 29.56, 21.63. HRMS (ESI, m / z) calculated for C18H18NO3S 328.10074 (M+H), found 328.09967.Attorney Docket No. 10620-164W02

[0980] NCSURef.: 2025-138-04

[0981] Synthesis of 2-methyl-4-(5-methyl-5-phenyl-l,4,2-oxathiazol-3-yl)benzoic acid (AV- 270): Hydrolysis of methyl ester was performed by dissolving theH°Y^T corresponding ester AV-1257 (246 mg, 1 equiv.) in THF (0.1 M) and O CH

[0982]

[0983] 35 mixture was cooled down to 0 °C. A solution of 1 M LiOH (10 equiv.) was added and the reaction was left stirring and followed by LCMS. Upon completion, reaction was acidified with IM HC1, and was extracted with DCM (3-5X) until the white precipitate disappeared from the aqueous layer. Organic phase was washed with brine, and dried over Na2SO4, concentrated in vacuo to afford the desired compounds (235 mg, quant.) and the crude was used for the next reaction. 'H NMR (600 MHz, DMSO) 513.12 (s, 1H), 7.90 - 7.85 (m, 1H), 7.62 (d, J= 7.8 Hz, 2H), 7.53 (d, J= 12.3 Hz, 4H), 7.42 (t, J= 7.7 Hz, 2H), 7.36 (t, J= 7.7 Hz, 1H), 2.55 -2.52 (m, 3H), 2.18 (d, J= 1.9 Hz, 3H).13CNMR(151 MHz, DMSO) 5 168.36, 156.15, 143.30, 140.45, 133.47, 131.41, 130.70, 130.68, 129.04, 128.92, 125.37, 125.13, 105.33, 40.54, 29.23, 21.42. LC-MS (ESI, APCI, m / z) 312 (M-H).

[0984] General procedure for the synthesis of 1,4,2-oxathiazole analogues:

[0985] In certain embodiments, amide bond formation is carried out by dissolving the carboxylic acid coupling partner in dry dimethylformamide (DMF, 0.01-0.05 M) and cooling the solution to 0 °C. A coupling reagent such as l-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI HC1, 1.1 equivalents) and a nucleophilic catalyst such as 4-dimethylaminopyridine (DMAP) (0.1 equivalents, optionally also supplemented to neutralize acidic counterions) are added, followed by addition of the amine component (1 equiv.). The reaction mixture is then allowed to warm to room temperature and stirred, for example overnight. Upon completion, the reaction mixture is diluted with water and brine, and extracted with an organic solvent such as ethyl acetate (3X). The combined organic layers may be washed with aqueous lithium chloride (5% w / v) and brine, dried over sodium sulfate, and concentrated under reduced pressure. The crude product may be purified, for example, by flash chromatography to afford the desired product.

[0986] Synthesis of 2-methyl-4-(5-methyl-5-phenyl- l,4,2-oxathiazol-3-yl)-N-(2-oxo-2-((2,2,2-trifhioroethyI)amino)ethyI)benzamide (AV-1262): The corresponding 1,4,2-m“" % 30 oxathaizole derivative was synthesized using the general procedure reported A

[0987] z=\Mcfor the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV- 1270 (20 mg, 1 equiv.) was dissolved in DMF (0.2 M), and EDCI HC1 (1.2 <cfequiv.), and DMAP (2 equiv.) were added, followed by the corresponding

[0988]

[0989] amine coupling partner. After purification, desired product was obtained as a white semisolidAttorney Docket No. 10620-164W02

[0990] NCSURef.: 2025-138-04

[0991] (9.5 mg, 33%).JH NMR (600 MHz, CDCh) 87.61, 7.60, 7.54, 7.51, 7.50, 7.43, 7.41, 7.41, 7.40, 7.39, 7.38, 7.35, 7.33, 7.32, 7.32, 7.04, 7.02, 6.74, 6.73, 6.72, 4.20, 4.19, 4.19, 4.18, 3.96, 3.95, 3.94, 3.92, 3.91, 3.91, 2.44, 2.44, 2.21, 2.20, 2.20, 1.26. HRMS (ESI, m / z) calculated for C21H21F3N3O3S, 452.12557 (M+H), found 452.124084.

[0992] Synthesis of 2-methyl-4-(5-methyl-5-phenyl- l,4,2-oxathiazol-3-yl)-N-(2,2,2-trifluoroethyl)benzamide (AV-1265): The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV-1270 (22 mg, 1 equiv.) was

[0993]

[0994] dissolved in DMF (0.2 M), and EDCI HC1 (1.2 equiv.), and DMAP (4 equiv.) were added, followed by the corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a white semisolid (16.9 mg, 61%). 'H NMR (600 MHz, CDCh) 8 7.61, 7.61, 7.61, 7.60, 7.60, 7.60, 7.54, 7.52, 7.52, 7.51, 7.50, 7.41, 7.40, 7.40, 7.39, 7.39, 7.38, 7.38, 7.38, 7.35, 7.35, 7.34, 7.34, 7.33, 7.33, 7.32, 7.32, 7.32, 6.05, 6.04, 6.03, 4.13, 4.11, 4.11, 4.10, 4.10, 4.09, 4.08, 4.07, 2.44, 2.21, 2.20, 2.20, 1.26. HRMS (ESI, m / z) calculated for C19H18F3N2O2S, 395.10411 (M+H), found 395.10294.

[0995] Synthesis of N,2-dimethyI-4-(5-methyI-5-phenyI-l,4,2-oxathiazol-3-yI)benzamide fUS (AV-1276): The corresponding 1,4,2-oxathaizole derivative was synthesized Z^-Me using the general procedure reported for the amide coupling. The

[0996]

[0997] ^-N, H^ corresponding 1,4,2-oxathiazole benzoate AV- 1270 (20 mg, 1 equiv.) was dissolved in DMF (0.2 M), and EDCI HC1 (1.2 equiv.), and DMAP (2 equiv.) were added, followed by the corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a clear wax (14.8 mg, 71%). 'H NMR (600 MHz, CDCh) 87.63 - 7.58 (m, 2H), 7.52 (d, J= 1.7 Hz, 1H), 7.48 (dd, J=7.9, 1.8 Hz, 1H), 7.41 - 7.31 (m, 4H), 5.75 (s, 1H), 3.00 (d, J= 4.9 Hz, 3H), 2.45 (s, 3H), 2.20 (s, 3H). HRMS (ESI, m / z) calculated for C18H19N2O2S, 327.11672 (M+H), found 327.11563.

[0998] Synthesis of methyl (2-methyl-4-(5-methyl-5-phenyl-l,4,2-oxathiazol-3-(f V+"> yl)benzoyl)glycinate (AV-1277). The corresponding 1,4,2-oxathaizole

[0999] { derivative was synthesized using the general procedure reported for the amide >•••£« C

[1000]

[1001] coupling. The corresponding 1,4,2-oxathiazole benzoate AV- 1270 (20 mg, 1 equiv.) was dissolved in DMF (0.2 M), and EDCI HC1 (1.2 equiv.), and DMAP (4 equiv.) were added, followed by the corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a light semisolid (15.3 mg, 62%). 'H NMR (600 MHz, CDCh) 8 7.62, 7.61, 7.61, 7.61, 7.60, 7.60, 7.54, 7.52, 7.52, 7.51, 7.50, 7.45, 7.44, 7.40, 7.40, 7.39, 7.39,Attorney Docket No. 10620-164W02

[1002] NCSURef.: 2025-138-04

[1003] 7.38, 7.38, 7.34, 7.34, 7.34, 7.33, 7.33, 7.32, 7.32, 7.32, 6.28, 6.27, 6.26, 4.23, 4.22, 3.80, 2.48, 2.20. HRMS (ESI, m / z) calculated for C20H21N2O4S, 385.12220 (M+H), found 385.11618.

[1004] Synthesis of 2-methyl-4-(5-methyl-5-phenyl-l,4,2-oxathiazol-3-yl)-N-(2-methylallyl) benzamide (AV-1278). The corresponding 1,4,2-oxathaizole derivative was synthesized using 5 the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV-1270 (20 mg, 1 equiv.) was dissolved in DMF (0.2 M), and EDCI HC1 (1.2 equiv.), and DMAP (4 equiv.) were

[1005]

[1006] added, followed by the corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a light semisolid (12.5 mg, 54%). 'H NMR (600 MHz, CDCh) 87.63 - 7.58 (m, 2H), 7.54 - 7.47 (m, 2H), 7.42 - 7.36 (m, 3H), 7.35 - 7.31 (m, 1H), 5.84 (d, J= 6.7 Hz, 1H), 4.90 (qd, J= 2.1, 1.0 Hz, 2H), 4.02 - 3.98 (m, 2H), 2.46 (s, 3H), 2.20 (s, 3H), 1.82- 1.79 (m, 3H). HRMS (ESI, m / z) calculated for C21H23N2O2S, 367.14802 (M+H), found 367.146881.

[1007] Synthesis of 2-methyl-4-(5-methyl-5-phenyl- l,4,2-oxathiazol-3-yl)-N-pentylbenzamide (AV- 1280). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The

[1008] AA corresponding 1,4,2-oxathiazole benzoate AV-1270 (20 mg, 1 equiv.) was dissolved in DMF (0.2 M), and EDCI HC1 (1.2 equiv.), and DMAP (2

[1009]

[1010] Meequiv.) were added, followed by the corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a wax (9.1 mg, 37%). 'H-NMR (600 MHz, CDC13) 87.63 - 7.58 (m, 2H), 7.52 (d, J = 1.7 Hz, 1H), 7.49 (dd, J = 8.0, 1.8 Hz, 1H), 7.41 - 7.31 (m, 4H), 5.70 (s, 1H), 3.43 (td, J = 7.3, 5.9 Hz, 2H), 2.45 (s, 3H), 2.20 (s, 3H), 1.60 (dd, J = 8.5, 5.7 Hz, 2H), 1.36 (dq, J = 7.1, 3.2 Hz, 4H), 0.93 - 0.90 (m, 3H).13C-NMR (151 MHz, CDC13) 8 169.19, 156.46, 142.98, 139.16, 136.89, 130.44, 129.72, 128.66, 128.56, 127.13, 125.45, 125.03, 104.97, 40.05, 29.70, 29.50, 29.25, 22.49, 19.81, 14.14. HRMS (ESI, m / z) calculated for C22H27N2O2S, 383.17932 (M+H), found 383.17810.

[1011] Synthesis of N-benzyl-2-methyl-4-(5-methyl-5-phenyl-l,4,2-oxathiazol-3-yl)benzamide (AV-1281). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV-1270 (20 mg, 1 equiv.) was dissolved in DMF (0.2 M), and EDCI HC1 (1.2 equiv.), and DMAP (2

[1012]

[1013] equiv.) were added, followed by the corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a light semisolid (7.0 mg, 27%). HRMS (ESI, m / z) calculated for C24H23N2O2S, 383.17932 (M+H), found 383.17645.

[1014] IllAttorney Docket No. 10620-164W02

[1015] NCSURef.: 2025-138-04

[1016] Synthesis of N-(2-(lH-indol-3-yl)ethyl)-2-methyl-4-(5-methyl-5-phenyl-l,4,2- oxathiazol-3-yl)benzamide (AV-1282). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV-1270 (20 mg, 1 equiv.) was dissolved in DMF (0.2 M), and EDCI HC1 (1.2 equiv.), and DMAP

[1017]

[1018] (4 equiv.) were added, followed by the corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a light semisolid (7.0 mg, 27%). 'H NMR (600 MHz, CDCh) 88.02, 7.64, 7.63, 7.60, 7.60, 7.59, 7.58, 7.58, 7.47, 7.47, 7.43, 7.41, 7.39, 7.39, 7.38, 7.38, 7.38, 7.37, 7.37, 7.37, 7.34, 7.34, 7.33, 7.32, 7.31, 7.23, 7.23, 7.22, 7.21, 7.20, 7.20, 7.14, 7.14, 7.13, 7.13, 7.13, 7.12, 7.12, 7.08, 7.07, 7.07, 5.77, 3.82, 3.81, 3.80, 3.79, 3.13, 3.11, 3.10, 3.09, 2.39, 2.19, 2.17, 1.27, 1.26, 1.26. HRMS (ESI, m / z) calculated for C27H26N3O2S, 456.17457 (M+H), found 456.17334.

[1019] Synthesis of 2-methyl-4-(5-methyl-5-phenyl-l,4,2-oxathiazol-3-yl)-N-(lH- pyrazolo[3,4-b]pyridin-3-yl)benzamide (AV- 1266). The corresponding 1,4,2-oxathaizole 4-^ o derivative was synthesized using the general procedure reported for thesamide coupling. The corresponding 1,4,2-oxathiazole benzoate AV- 1270 V-?~Me(22 mg, 1 equiv.) was dissolved in DMF (0.2 M), and EDCI HC1 (1.2 ^-NH

[1020] ° equiv.), and DMAP (2 equiv.) were added, followed by the

[1021]

[1022] H20 corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a light semisolid (9.5 mg, 32%). 'H NMR (600 MHz, CDCh) 8 8.72, 8.72, 8.71, 7.62, 7.61, 7.60, 7.58, 7.56, 7.48, 7.48, 7.47, 7.46, 7.41, 7.40, 7.39, 7.38, 7.37, 7.35, 7.34, 7.31, 7.31, 7.30, 4.52, 3.35, 3.35, 3.35, 2.39, 2.37, 2.22, 2.22, 2.21, 1.28, 1.26, 1.26. HRMS (ESI, m / z) calculated for C23H20N5O2S, 430.13377 (M+H), found 430.13265.

[1023] Synthesis of N-(2-ethyl-3-oxoisoxazolidin-4-yl)-2-methyl-4-(5-methyl-5-phenyl- 1,4,2- oxathiazol-3-yl)benzamide (AV-1271). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. / “VME The corresponding 1,4,2-oxathiazole benzoate AV- 1270 (100 mg, 1

[1024] equiv.) was dissolved in DMF (0.2 M), and EDCI HC1 (1.2 equiv.), and

[1025]

[1026] 30 DMAP (4 equiv.) were added, followed by the corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a light solid (94.6 mg, 70%). 'H NMR (600 MHz, CDCh) 87.60 (dd, J= 7.6, 2.4 Hz, 2H), 7.54 (s, 1H), 7.51 (d, J = 8.2 Hz, 1H), 7.47 - 7.43 (m, 1H), 7.39 (t, J= 7.7 Hz, 2H), 7.33 (t, J= 7.6 Hz, 1H), 6.44 (s, 1H), 5.00 -4.94 (m, 1H), 4.84 (td, J= 8.8, 4.9 Hz, 1H), 4.04 (dd, J= 11.2, 8.0 Hz, 1H), 3.68 (p,Attorney Docket No. 10620-164W02

[1027] NCSURef.: 2025-138-04

[1028] J= 6.9 Hz, 1H), 3.64 (s, OH), 2.48 - 2.45 (m, 3H), 2.22 - 2.18 (m, 3H), 1.25 (t, J= 7.0 Hz, 4H).

[1029] 13CNMR(151 MHZ, CDCh) 8 169.53, 164.96, 156.11, 142.78, 137.43, 136.54, 130.53, 130.37, 128.56, 128.43, 127.48, 125.33, 124.88, 105.00, 73.40, 53.07, 40.22, 29.56, 19.92, 12.17. HRMS (ESI, m / z) calculated for C22H24N3O4S, 426.14875 (M+H), found 426.14739.

[1030] Synthesis of N-(l-ethylpyrrolidin-3-yl)-2-methyl-4-(5-methyl-5-phenyl-l,4,2- oxathiazol-3-yl)benzamide (AV-1267). The corresponding 1,4,2-oxathaizole derivative wasMe 0synthesized using the general procedure reported for the amide coupling. x / V%hN

[1031] The corresponding 1,4,2-oxathiazole benzoate AV-1270 (22 mg, 1 equiv.) Me

[1032] X'==x_NHwas dissolved in DMF (0.2 M), and EDCI HC1 (1.2 equiv.), and DMAP (2

[1033]

[1034] ^? N4PMS equiv.) were added, followed by the corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a clear oil (16.6 mg, 60%). 'H NMR (600 MHz, MeOD) 87.64, 7.63, 7.63, 7.63, 7.63, 7.62, 7.62, 7.62, 7.61, 7.55, 7.55, 7.55, 7.55, 7.54, 7.54, 7.53, 7.53, 7.52, 7.43, 7.42, 7.42, 7.42, 7.41, 7.41, 7.40, 7.39, 7.39, 7.39, 7.38, 7.36, 7.36, 7.36, 7.35, 7.34, 7.34, 7.34, 7.33, 7.33, 7.33, 4.60, 4.57, 4.56, 4.56, 4.56, 4.56, 4.55, 4.55, 4.55, 4.54, 4.54, 4.54, 4.53, 3.68, 3.25, 3.24, 3.22, 3.21, 3.20, 3.20, 3.19, 3.18, 3.16, 3.16, 3.14, 3.13, 2.85, 2.83, 2.82, 2.81, 2.76, 2.75, 2.74, 2.41, 2.40, 2.40, 2.39, 2.38, 2.37, 2.36, 2.35, 2.19, 2.19, 1.92, 1.91, 1.91, 1.90, 1.89, 1.88, 1.88, 1.87, 1.86, 1.85, 1.84, 1.83, 1.81, 1.80, 1.79, 1.30, 1.22, 1.21, 1.20, 1.12, 1.11, 1.11, 1.10, 1.10, 1.09. HRMS (ESI, m / z) calculated for C23H28N3O2S, 410.19022 (M+H), found 410.18914.

[1035] Synthesis of N-cyclopropyl-2-methyl-4-(5-methyl-5-phenyl-l,4,2-oxathiazol-3- yl)benzamide (AV-1279). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The W H

[1036] corresponding 1,4,2-oxathiazole benzoate AV- 1270 (20 mg, 1 equiv.) was ( / V- Me

[1037] dissolved in DMF (0.2 M), and EDCI HC1 (1.2 equiv.), and DMAP (2 X— NH

[1038]

[1039] 02^> equiv.) were added, followed by the corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a light film (2.8 mg, 12.5%). 'H NMR (600 MHz, CDCh) 87.60 (d, J= 7.7 Hz, 2H), 7.51 (s, 1H), 7.48 (d, J= 8.1 Hz, 1H), 7.39 (t, J= 7.6 Hz, 2H), 7.33 (t, J= 7.7 Hz, 2H), 5.83 (s, 1H), 2.89 (td, J= 7.1, 3.6 Hz, 1H), 2.44 (s, 3H), 2.20 (s, 3H), 0.88 (t, J= GA Hz, 4H). HRMS (ESI, m / z) calculated for C20H21N2O2S, 353.13237 (M+H), found 353.13113.Attorney Docket No. 10620-164W02

[1040] NCSURef.: 2025-138-04

[1041] Synthesis of N-cyclobutyl-2-methyl-4-(5-methyl-5-phenyl-l,4,2-oxathiazol-3- yl)benzamide (AV-1284). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV- 1270 (20 mg,

[1042]

[1043] 1 equiv.) was dissolved in DMF (0.2 M), and EDCI HC1 (1.2 equiv.), and DMAP (2 equiv.) were added, followed by the corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a light film (18.4 mg, 80%). 'H NMR (600 MHz, CDCh) 87.63 - 7.58 (m, 2H), 7.51 (d, J= 1.6 Hz, 1H), 7.48 (dd, J=7.9, 1.7 Hz, 1H), 7.39 (t, J= 7.6 Hz, 2H), 7.34 (t, J= 7.6 Hz, 2H), 5.86 (d, J= 8.0 Hz, 1H), 4.57 (h, J= 8.1 Hz, 1H), 2.44 (s, 5H), 2.20 (s, 3H), 1.98 - 1.88 (m, 2H), 1.81 - 1.73 (m, 2H). HRMS (ESI, m / z) calculated for C21H23N2O2S, 367.14802 (M+H), found 367.14703.

[1044] Synthesis of N-cyclopentyl-2-methyl-4-(5-methyl-5-phenyl-l,4,2-oxathiazol-3- yl)benzamide (AV-1268). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV-1270 (22 mg, 1

[1045]

[1046] equiv.) was dissolved in DMF (0.2 M), and EDCI HC1 (1.2 equiv.), and DMAP (2 equiv.) were added, followed by the corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a clear oil (16.6 mg, 60%). 'H NMR (600 MHz, CDCh) 87.61, 7.60, 7.51, 7.48, 7.39, 7.37, 7.34, 7.33, 5.64, 2.44, 2.44, 2.44, 2.20, 2.20, 2.19, 2.09, 1.70, 1.26, 0.84. HRMS (ESI, m / z) calculated for C22H25N2O2S, 381.16367 (M+H), found 381.16235.

[1047] Synthesis of N-cyclohexyl-2-methyl-4-(5-methyl-5-phenyl- l,4,2-oxathiazol-3- yl)benzamide (AV- 1283). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV- 1270 (20 mg,

[1048]

[1049] 1 equiv.) was dissolved in DMF (0.2 M), and EDCI HC1 (1.2 equiv.), and DMAP (4 equiv.) were added, followed by the corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a film(3 mg, 12%). HRMS (ESI, m / z) calculated for C23H27N2O2S, 395.17932 (M+H), found 395.17831.

[1050] Synthesis of 2-methyl-4-(5-methyl-5-phenyl- l,4,2-oxathiazol-3-yl)-N- (tetrahydrofuran-3-yl)benzamide (AV-1272). The corresponding 1,4,2- oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV-

[1051]

[1052] 1270 (25 mg, 1 equiv.) was dissolved in DMF (0.2 M), and EDCI HC1 (1.2Attorney Docket No. 10620-164W02

[1053] NCSURef.: 2025-138-04

[1054] equiv.), and DMAP (2 equiv.) were added, followed by the corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a clear oil (18.8 mg, 62%). 'H NMR (600 MHz, CDCh) 87.61, 7.61, 7.61, 7.61, 7.60, 7.60, 7.60, 7.60, 7.59, 7.52, 7.52, 7.52, 7.50, 7.50, 7.49, 7.49, 7.40, 7.40, 7.40, 7.40, 7.39, 7.39, 7.39, 7.38, 7.38, 7.38, 7.38, 7.37, 7.36, 7.35, 7.34, 7.34, 7.33, 7.33, 7.33, 7.32, 7.32, 7.32, 5.94, 5.92, 4.73, 4.72, 4.72, 4.71, 4.71, 4.70, 4.70, 4.69, 4.69, 4.69, 4.68, 3.99, 3.97, 3.97, 3.96, 3.95, 3.91, 3.90, 3.89, 3.89, 3.85, 3.84, 3.83, 3.82, 3.82, 3.81, 3.79, 3.78, 3.77, 3.77, 2.45, 2.40, 2.38, 2.38, 2.37, 2.37, 2.37, 2.37, 2.37, 2.36, 2.36, 2.36, 2.36, 2.35, 2.35, 2.34, 2.34, 2.20, 1.92, 1.92, 1.92, 1.92, 1.91, 1.91, 1.91, 1.90, 1.90, 1.90, 1.90, 1.89, 1.89, 1.88, 1.87, 1.31, 1.30, 1.29, 1.27, 1.27, 1.26, 1.25, 1.25. HRMS (ESI, m / z) calculated for C21H23N2O3S, 383.14294 (M+H), found 383.14160.

[1055] Synthesis of N-(2-hydroxycyclopentyl)-2-methyl-4-(5-methyl-5-phenyl- 1,4,2- oxathiazol-3-yl)benzamide (AV-1273). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The W corresponding 1,4,2-oxathiazole benzoate AV-1270 (25 mg, 1 equiv.) was ’N\L y0H

[1056]

[1057] (jj dissolved in DMF (0.2 M), and EDCI HC1 (1.2 equiv.), and DMAP (2 equiv.) were added, followed by the corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a clear wax (8.2 mg, 26%). 'H NMR (600 MHz, CDCh) 87.63 - 7.58 (m, 2H), 7.53 (s, 1H), 7.50 (dd, J=7.8, 1.8 Hz, 1H), 7.41 - 7.37 (m, 3H), 7.35 - 7.31 (m, 1H), 5.89 (d, J= 4.3 Hz, 1H), 4.25 (s, 1H), 4.11 (q, J= 6.4 Hz, 1H), 4.02 (ddd, J= 13.7, 8.5, 5.1 Hz, 1H), 2.46 (s, 3H), 2.27 -2.21 (m, 1H), 2.20 (s, 3H), 2.07 (dt, J = 13.1, 6.9 Hz, 1H), 1.91 - 1.80 (m, 1H), 1.79 - 1.69 (m, 2H), 1.49 (dq, J= 12.9, 8.2 Hz, 1H). HRMS (ESI, m / z) calculated for C22H25N2O3S, 397.15859 (M+H), found 397.15744.

[1058] Synthesis of N-(l,l-dioxidothietan-3-yl)-2-methyl-4-(5-methyl-5-phenyl-l,4,2- oxathiazol-3-yl)benzamide (AV-1285). The corresponding 1,4,2- ^25 oxathaizole derivative was synthesized using the general procedure reported ^-NH for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV- °

[1059]

[1060] fco 1270 (20 mg, 1 equiv.) was dissolved in DMF (0.2 M), and EDCI HC1 (1.2 equiv.), and DMAP (2 equiv.) were added, followed by the corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a clear oil (15.7 mg, 59%). 'HNMR (600 MHz, CDCh) 87.63 - 7.58 (m, 2H), 7.52 (d, J= 1.7 Hz, 1H), 7.50 - 7.46 (m, 1H), 7.42 - 7.31 (m, 4H), 6.59 (d, J= 6.8 Hz, 1H), 4.86 (dddd, J= 11.9, 8.5, 6.9, 3.4 Hz, 1H), 4.65 - 4.57 (m, 2H), 4.07 - 4.00 (m, 2H), 2.44 (s, 3H), 2.21 (s, 3H). HRMS (ESI, m / z) calculated for C20H21N2O4S2, 417.09427 (M+H), found 417.09307.Attorney Docket No. 10620-164W02

[1061] NCSURef.: 2025-138-04

[1062] Synthesis of (Z)-N-((methoxyimino)methyl)-2-methyl-4-(5-methyl-5-phenyl-l,4,2- oxathiazol-3-yl)benzamide (AV-1264). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV- 1270 (22 mg, 1

[1063]

[1064] equiv.) was dissolved in DMF (0.2 M), and EDCI HC1 (1.2 equiv.), and DMAP (2 equiv.) were added, followed by the corresponding amine coupling partner (2 equiv.). After purification, desired product was obtained as a clear oil (7.3 mg, 25%). 'H NMR (600 MHz, CDCh) 87.62, 7.61, 7.61, 7.60, 7.60, 7.60, 7.60, 7.60, 7.60, 7.60, 7.59, 7.59, 7.59, 7.58, 7.58, 7.57, 7.57, 7.57, 7.56, 7.55, 7.54, 7.54, 7.54, 7.53, 7.53, 7.53, 7.52, 7.52, 7.49, 7.40, 7.40, 7.40, 7.39, 7.39, 7.38, 7.38, 7.37, 7.37, 7.35, 7.35, 7.35, 7.34, 7.34, 7.34, 7.34, 7.33, 7.33, 7.32, 7.32, 7.32, 7.32, 7.31, 3.79, 3.77, 3.76, 3.75, 3.70, 3.70, 3.67, 2.46, 2.39, 2.36, 2.25, 2.23, 2.22, 2.22, 2.22, 2.22, 2.22, 2.21, 2.21, 2.21, I 2.20, o o 2.20, 2.18, 2.17, 1.29, 1.27, 1.26, 1.26, 1.25, 1.25. HRMS (ESI, m / z) calculated for C19H20N3O3S, 370.12254 (M+H), found 370.12145.

[1065] Synthesis of CFa-containing 1.4.2-oxa thiazole analogs

[1066] o CH3

[1067] 3-chloro-5- H NA??) irSdT3Phenyl 3,5-dichloro- 3,5-dichloro-4- 3,4,5-trichloro(trifluoro- phenyl fluorophenyl phenyl methyl)phenyl EDC^HCI H 0 Vx NEt '-0 MeO JVFS NA. / *- O

[1068] H [pr s '©

[1069] H30 CH3

[1070]

[1071] Synthesis of methyl (Z)-4-((hydroxyimino)((2,2,2-trifluoro-l-phenylethyl)thio)methyl)-2-methylbenzoate (AV-1360). The target compound was synthesized using General procedures A and / or B for the synthesis of thiohydroximic acids. Chloroxime of AV- 1221 (500 mg, 1 equiv), benzyl mercaptan

[1072]

[1073] derivative (1 equiv.) and triethylamine (1 equiv.). Desired product was purified by flash chromatography, and obtained as a clear semisolid (287 mg, 53%).1H NMR (600 MHz, CDCh) 88.13, 8.12, 8.12, 8.11, 7.98, 7.98, 7.97, 7.96, 7.96, 7.95, 7.94, 7.93, 7.93, 7.92, 7.92, 7.46, 7.46, 7.45, 7.45, 7.45, 7.44, 7.44, 7.43, 7.43, 7.38, 7.38, 7.37, 7.37, 7.37, 7.36,Attorney Docket No. 10620-164W02

[1074] NCSURef.: 2025-138-04

[1075] 7.36, 7.36, 7.36, 7.35, 7.35, 7.35, 7.34, 7.34, 7.34, 7.33, 7.33, 7.31, 7.31, 7.30, 7.30, 7.27, 7.27, 7.26, 7.26, 7.25, 7.25, 7.25, 7.25, 7.25, 3.95, 3.95, 3.94, 3.94, 3.94, 3.93, 3.93, 3.93, 3.92, 3.92, 3.92, 3.91, 3.91, 3.91, 3.91, 3.90, 3.90, 3.89, 3.89, 3.89, 3.89, 3.88, 2.64, 2.63, 2.63, 2.62, 2.62, 2.61, 2.60, 2.59, 1.58, 1.57, 1.57, 1.56, 1.56, 1.56, 1.54, 1.53. LRMS (ESI + APCI), +384 (M+H), -382 (M-H).

[1076] Synthesis of methyl (Z)-4-(((l-(3,5-dichlorophenyl)-2,2,2-trifluoroethyl)thio) (hydroxyimino)methyl)-2-methylbenzoate (AV-1362). The target compound was synthesized using General procedures A and / or B for the synthesis of thiohydroximic acids. Chloroxime of AV-1221 (300 mg, 1 equiv), benzyl mercaptan

[1077]

[1078] derivative (1 equiv.) and triethylamine (1 equiv.). Desired product was purified by flash chromatography, and obtained as a light solid (213 mg, 56%). 'H NMR (600 MHz, CDCh) 88.01 (s, 1H), 7.98 (d, J= 8.1 Hz, 1H), 7.47 - 7.41 (m, 1H), 7.36 (dd, J= 3.9, 2.0 Hz, 2H), 7.13 (d, J= 1.8 Hz, 2H), 4.74 (q, J= 8.0 Hz, 1H), 3.93 (s, 3H), 2.62 (s, 3H). LRMS (ESI + APCI), 453 (M+H).

[1079] Synthesis of methyl 2-methyl-4-(5-phenyl-5-(trifluoromethyl)-l,4,2-oxathiazol-3- yl)benzoate (AV-1405). The target compound was synthesized using General procedure for the preparation of 1,4,2-oxathiazoles.

[1080]

[1081] Thiohydroximic acid of AV-1360 (100 mg, 0.014 M). Desired product was obtained as a clear oil. LRMS (ESI + APCI), 382 (M+H).

[1082] Synthesis of methyl 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-l,4,2-oxathiazol-3-yl)-2-methylbenzoate (AV-1406). The target compound was synthesized using General procedure for the preparation of 1,4,2-oxathiazoles. Thiohydroximic acid of AV-1362 (150 mg, 0.014 M). Desired product was obtained as a yellow oil. LRMS (ESI + APCI), 450 (M+H).

[1083] Synthesis of Lotilaner-Inspired 1,4,2-oxathiazolesAttorney Docket No. 10620-164W02

[1084] NCSURef.: 2025-138-04

[1085]

[1086] Synthesis of methyl 5-((hydroxyimino)methyl)thiophene-2-carboxylate (AV- 1286).

[1087] To a solution of the corresponding aldehyde (3.0 g, 1 equiv.) in absolute EtOH (0.2 M) was N'OHadded hydroxylamine HC1 (1.5 equiv.) and pyridine (3 equiv.) successively O c JI

[1088] > / >1 — at R. T. The reaction was stirred overnight. Upon completion, EtOH was

[1089]

[1090] MeO v—

[1091] removed and the residue was suspended in IN HC1. Extracted with EtOAc (3X) and the combined organic layers were washed with brine (IX), dried over Na2SO4, filtered, and concentrated to yield the crude mixture of E / Z oximes as an white solid Mixture was purified using flash chromatography. Desired product obtained as a white solid (3.26 g, quant.).XH NMR (600 MHz, DMSO) 5 12.52 (s, 1H), 7.99 (s, 1H), 7.78 (d, J= 4.0 Hz, 1H), 7.51 (d, J = 4.0 Hz, 1H), 3.83 (s, 3H). HRMS (ESI, m / z) calculated for C7H8NO3S, 186.02249 (M+H), found 186.02174.

[1092] Synthesis of methyl 5-((hydroxyimino)methyl)-3-methylthiophene-2-carboxylate (AV-1295). To a solution of the corresponding aldehyde (900 mg, 1 equiv.) in absolute EtOH, OH

[1093] Ns (0.5 M) was added hydroxylamine HC1 (1.5 equiv.) and pyridine (3 equiv.) Meo' y-J successively at R. T. The reaction was stirred overnight. Upon completion,

[1094]

[1095] Me

[1096] EtOH was removed and the residue was suspended in IN HC1. Extracted with EtOAc (3X) and the combined organic layers were washed with brine (IX), dried over Na2SO4, filtered, and concentrated to yield the crude mixture of E / Z oximes as an white solid Mixture was purified using flash chromatography. Desired product obtained as a white solid (695 mg, 71%).Attorney Docket No. 10620-164W02

[1097] NCSURef.: 2025-138-04

[1098] 'HNMR (600 MHz, CDCk) 88.18 (s, 1H), 7.56 (s, 1H), 7.01 (s, 1H), 3.87 (s, 3H), 2.52 (s, 3H).

[1099] 13CNMR(151 MHZ, CDCk) 8 163.10, 146.25, 144.68, 138.88, 133.23, 127.64, 52.10, 16.04. LRMS (ESI + APCI), 200 (M+H).

[1100] Synthesis of methyl (E)-5-((hydroxyimino)methyl)-3-methylfuran-2-carboxylate (AV-1307). To a solution of the corresponding aldehyde (600 mg, 1 equiv.) in absolute EtOH (0.1 M) was added hydroxylamine HC1 (1.5 equiv.) and pyridine (3 equiv.) successively at R. T. The reaction was stirred overnight. Upon completion,

[1101]

[1102] EtOH was removed and the residue was suspended in IN HC1. Extracted with EtOAc (3X) and the combined organic layers were washed with brine (IX), dried over Na2SO4, filtered, and concentrated to yield the crude mixture of E / Z oximes as an white solid Mixture was purified using flash chromatography. Desired product obtained as a white solid (620 mg, quant.).XH NMR (600 MHz, DMSO) 8 11.71 (s, 1H), 8.05 (s, 1H), 6.78 (s, 1H), 3.81 (s, 3H), 2.29 (s, 3H). HRMS (ESI, m / z) calculated for C8H10NO4, 184.06098 (M+H), found 184.06024.

[1103] Synthesis of methyl-5-((hydroxyimino)((l-phenylethyl)thio)methyl)thiophene-2- carboxylate (AV- 1292). The target compound was synthesized using General procedures A N'OHCH, and / or B for the synthesis of thiohydroximic acids. Chloroxime of AV-

[1104]

[1105] 1287 (1.29 mg, 1 equiv), benzyl mercaptan derivative (1 equiv.) and triethylamine (1 equiv.). Desired product was purified by flash chromatography, and obtained as a light semisolid (624 mg, 36%). 'H NMR (600 MHz, DMSO) 8 12.49 (s, 1H), 7.70 (d, J= 4.0 Hz, 1H), 7.42 (d, J= 4.0 Hz, 1H), 7.35 - 7.30 (m, 2H), 7.31 - 7.25 (m, 3H), 7.24 - 7.19 (m, 1H), 5.03 (q, J= 6.9Hz, 1H), 3.81 (s, 3H), 1.53 (d, J= 7.0 Hz, 3H). LRMS (ESI + APCI), 322 (M+H).

[1106] Synthesis of methyl-5-((hydroxyimino)((l-phenylethyl)thio)methyl)-3- methylthiophene-2-carboxylate (AV- 1345). The target compound was synthesized using N' CH25 General procedures A and / or B for the synthesis of thiohydroximic acids.

[1107] 0.

[1108] MeO ' Chloroxime of AV-1316 (200 mg, 1 equiv), benzyl mercaptan derivative

[1109]

[1110] Me

[1111] (1 equiv.) and triethylamine (1 equiv.). Desired product was purified by flash chromatography, and obtained as a yellow oil (206 mg, 89%).1H NMR (600 MHz, CDCk) 87.94 (s, 1H), 7.33 - 7.27 (m, 4H), 7.23 (ddt, J= 8.6, 6.3, 1.7 Hz, 1H), 7.16 (s, 1H), 4.88 (p, J= 6.9 Hz, 1H), 3.86 (s, 3H), 2.50 (s, 3H), 1.65 (d, J= 7.0 Hz, 3H). LRMS (ESI + APCI), 336 (M+H).Attorney Docket No. 10620-164W02

[1112] NCSURef.: 2025-138-04

[1113] Synthesis of methyl-5-((hydroxyimino)((l-phenylethyl)thio)methyl)-3-methylfuran- 2-carboxylate (AV-1346). The target compound was synthesized using General procedures A and / or B for the synthesis of thiohydroximic acids. Chloroxime of AV- 1317 (200 mg, 1 equiv), benzyl mercaptan derivative (1 equiv.) and 5 triethylamine (1 equiv.). Desired product was purified by flash chromatography, and obtained as a yellow oil (56 mg, 23%). 'H NMR (600 MHz, CDCh) 87.92 (s, 1H), 7.30 - 7.23 (m, 5H), 7.23 - 7.17 (m, 1H), 6.54 (d, J= 0.6 Hz, 1H), 3.90 (s, 3H), 2.32 (s, 3H), 1.63 (d, J= 7.0 Hz, 3H). LRMS (ESI + APCI), 320 (M+H).

[1114] Synthesis of methyl 5-(5-methyl-5-phenyl-l,4,2-oxathiazol-3-yl)thiophene-2- carboxylate (AV-1293). The target compound was synthesized using General procedure for theN,oCHpreparation of 1,4, 2-oxathiazoles. Thiohydroximic acid of AV-1292 (620 II XyAj, 2\ / s'rr ^sTl I mg, 0.014 M). Desired product was obtained as a clear oil (370 mg, z \JIMeO60%). 'H NMR (600 MHz, CDCh) 87.69 (d, J= 4.0 Hz, 1H), 7.62 - 7.55 (m, 2H), 7.42 - 7.36 (m, 2H), 7.36 - 7.31 (m, 1H), 7.21 (d, J= 4.0 Hz, 1H), 3.90 (s, 3H), 2.20 (s, 3H). LRMS (ESI + APCI), 320 (M+H).

[1115] Synthesis of methyl 3-methyl-5-(5-methyl-5-phenyl-l,4,2-oxathiazol-3-yl)thiophene- 2-carboxylate (AV-1357). The target compound was synthesized using General procedure foro s^e preparation of 1,4, 2-oxathiazoles. Thiohydroximic acid of AV- 1345Me0' yJI (206 mg, 0.014 M). Desired product was obtained as a clear oil (114 mg, Me 20 56%). 'H NMR (600 MHz, CDCh) 87.61 - 7.56 (m, 2H), 7.41 - 7.36 (m, 2H), 7.34 (ddt, J= 8.4, 6.3, 1.3 Hz, 1H), 7.06 (d, J= 0.5 Hz, 1H), 3.87 (s, 3H), 2.52 - 2.49 (m, 3H), 2.19 (s, 3H). LRMS (ESI + APCI), 334 (M+H).

[1116] Synthesis of methyl 3-methyl-5-(5-methyl-5-phenyl-l,4,2-oxathiazol-3-yl)furan-2- carboxylate (AV-1358). The target compound was synthesized using General procedure for the preparation of 1,4, 2-oxathiazoles. Thiohydroximic acid of AV-1346 (56 mg, 0.014 M). Desired product was obtained as a clear oil (14.8 mg, 27%). 'H NMR (600 MHz, CDCh) 87.59 - 7.55 (m, 2H), 7.38 (dd, J= 8.4, 6.7 Hz, 2H), 7.35 - 7.31 (m, 1H), 6.75 (s, 1H), 3.89 (s, 3H), 2.36 (s, 3H), 2.19 (s, 3H). LRMS (ESI + APCI), 318 (M+H).

[1117] Synthesis of 5-(5-methyl-5-phenyl-l,4,2-oxathiazol-3-yl)thiophene-2-carboxylic acid (AV-1294). Hydrolysis of methyl ester was performed by dissolving the corresponding ester AV-1293 (370 mg, 1 equiv.) in THF (0.1 M) and mixture was cooled down to 0 °C. A solution of 1 M LiOH (10 equiv.) was added and upon completion, reaction was acidified with IM HC1, and was extracted with

[1118]

[1119] Attorney Docket No. 10620-164W02

[1120] NCSURef.: 2025-138-04

[1121] DCM. Organic phase was washed with brine, concentrated in vacuo to afford the desired compounds (305 mg, quant.) and the crude was used for the next reaction.1H NMR (600 MHz, DMSO) 8 13.59 (s, 1H), 7.69 (d, J= 3.9 Hz, 1H), 7.63 - 7.58 (m, 2H), 7.45 - 7.40 (m, 3H), 7.39 - 7.35 (m, 1H), 2.19 (s, 3H). LRMS (ESI + APCI), 304 (M-H).

[1122] Synthesis of 3-methyl-5-(5-methyl-5-phenyl- l,4,2-oxathiazol-3-yl)thiophene-2- carboxylic acid (AV-1365). Hydrolysis of methyl ester was performed by dissolving the corresponding ester AV-1357 (114 mg, 1 equiv.) in THF (0.1 M) and mixture was cooled down to 0 °C. A solution of 1 M LiOH (10 equiv.) was

[1123]

[1124] added and upon completion, reaction was acidified with IM HC1, and was extracted with DCM. Organic phase was washed with brine, concentrated in vacuo to afford the desired compounds (98 mg, 90%) and the crude was used for the next reaction. LRMS (ESI + APCI), 318 (M-H).

[1125] Synthesis of 3-niethyl-5-(5-methyl-5-phenyl-l,4,2-oxathiazol-3-yl)furan-2-carboxylic acid (AV-1366). Hydrolysis of methyl ester was performed by dissolving the corresponding ester AV-1358 (14.8 mg, 1 equiv.) in THF (0.1 M) and mixture was cooled o.

[1126] down to 0 °C. A solution of 1 M LiOH (10 equiv.) was added and upon HO )

[1127]

[1128] Me completion, reaction was acidified with IM HC1, and was extracted with DCM. Organic phase was washed with brine, concentrated in vacuo to afford the desired compounds (11 mg, 79%) and the crude was used for the next reaction. LRMS (ESI + APCI), 302 (M-H).

[1129] Synthesis of 5-(5-methyl-5-phenyl-l,4,2-oxathiazol-3-yl)-N-(2-oxo-2-((2,2,2- trifluoroethyl)amino)ethyl)thiophene-2-carboxamide (AV- 1304). The corresponding 1,4,2- oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV-1294 (30 mg, 1 equiv.) was dissolved in DMF (0.025 M),

[1130]

[1131] and EDCI HC1 (1.1 equiv.), and DMAP (2 equiv.) were added, followed by the corresponding amine coupling partner (1.5 equiv.). After purification, desired product was obtained as a white solid (27.6 mg, 63%). 'H NMR (600 MHz, MeOD) 87.67 (d, J= 4.0 Hz, 1H), 7.64 - 7.59 (m, 2H), 7.44 - 7.38 (m, 2H), 7.37 - 7.34 (m, 1H), 7.31 (d, J= 4.0 Hz, 1H), 4.07 (s, 2H), 3.94 (q, J = 9.3 Hz, 2H), 2.19 (s, 3H). HRMS (ESI, m / z) calculated for C18H17F3N3O3S2, 444.06634 (M+H), found 444.06539.Attorney Docket No. 10620-164W02

[1132] NCSURef.: 2025-138-04

[1133] Synthesis of N-(2-ethyl-3-oxoisoxazolidin-4-yl)-5-(5-methyl-5-phenyl- 1,4,2- oxathiazol-3-yl)thiophene-2-carboxamide (AV-1305). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the / "sHo amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV-1294

[1134]

[1135] o (30 mg, 1 equiv.) was dissolved in DMF (0.025 M), and EDCI HC1 (1.1 equiv.), and DMAP (3 equiv.) were added, followed by the corresponding amine coupling partner (1.5 equiv.). After purification, desired product was obtained as a white solid (24.4 mg, 60%). 'H NMR (600 MHz, CDCh) 87.61 - 7.56 (m, 2H), 7.48 (dd, J= 4.0, 0.6 Hz, 1H), 7.39 (ddd, J= 7.8, 7.0, 1.3 Hz, 2H), 7.36- 7.31 (m, 1H), 7.18 (dd, J = 5.5, 4.0 Hz, 1H), 7.02 (t, J = 5.3 Hz, 1H), 4.95 - 4.85 (m, 2H), 4.12 (q, J= 7.1 Hz, 1H), 4.08 - 4.00 (m, 1H), 3.74 - 3.60 (m, 2H), 2.20 (d, J= 1.9 Hz, 3H), 2.04 (s, 1H), 1.26 (td, J= 7.2, 2.3 Hz, 4H). HRMS (ESI, m / z) calculated for C19H20N3O4S2, 418.08952 (M+H), found 418.08862.

[1136] Synthesis of (Z)-N-((methoxyimino)methyl)-5-(5-methyl-5-phenyl-l,4,2-oxathiazol- 3-yl)thiophene-2-carboxamide (AV- 1306). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV-1294 (30 mg, 1 equiv.) was dissolved in DMF (0.025 M), and EDCI HC1 (1.1

[1137]

[1138] equiv.), and DMAP (3 equiv.) were added, followed by the corresponding amine coupling partner (1.5 equiv.). After purification, desired product was obtained as a light yellow solid (8.6 mg, 24%). 'H NMR (600 MHz, CDCh) 57.73 (d, J= 9.6 Hz, 1H), 7.60 - 7.57 (m, 2H), 7.55 (d, J= 4.0 Hz, 1H), 7.43 - 7.37 (m, 2H), 7.37 - 7.32 (m, 1H), 7.25 (d, J= 4.0 Hz, 1H), 3.93 (s, 3H), 2.21 (s, 3H). HRMS (ESI, m / z) calculated for C16H16N3O3S2, 362.06331 (M+H), found 362.06198.

[1139] Synthesis of 5-(5-methyl-5-phenyl-l,4,2-oxathiazol-3-yl)-N-(2,2,2-trifluoroethyl) thiophene-2-carboxamide (AV-1308). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV-1294 (30 mg, 1 equiv.)

[1140]

[1141] was dissolved in DMF (0.025 M), and EDCI HC1 (1.1 equiv.), and DMAP (3 equiv.) were added, followed by the corresponding amine coupling partner (1.5 equiv.). After purification, desired product was obtained as a white solid (9.3 mg, 25%). 'H NMR (600 MHz, CDCh) 87.61 - 7.56 (m, 2H), 7.48 (d, J= 4.0 Hz, 1H), 7.42 - 7.36 (m, 2H), 7.36 - 7.31 (m, 1H), 7.21 (d, J= 4.0 Hz, 1H), 6.36 (t, J= 6.5 Hz, 1H), 4.15 - 4.03 (m, 2H), 2.20 (s, 3H). LRMS (ESI + APCI), 387 (M+H).Attorney Docket No. 10620-164W02

[1142] NCSURef.: 2025-138-04

[1143] Synthesis of N-(l,l-dioxidothietan-3-yl)-5-(5-methyl-5-phenyl-l,4,2-oxathiazol-3- yl)thiophene-2-carboxamide (AV-1310). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV-1294 (30 mg, 1 equiv.) Vs=° was dissolved in DMF (0.025 M), and EDCI HC1 (1.1 equiv.), and DMAP

[1144]

[1145] o

[1146] (2 equiv.) were added, followed by the corresponding amine coupling partner (1.5 equiv.). After purification, desired product was obtained as a white solid (21.7 mg, 54%).JH NMR (600 MHz, CDCh) 87.61 - 7.56 (m, 2H), 7.46 (d, J= 4.0 Hz, 1H), 7.42 - 7.37 (m, 2H), 7.37 - 7.32 (m, 1H), 7.21 (d, J= 3.9 Hz, 1H), 4.64 - 4.57 (m, 2H), 4.12 - 4.05 (m, 2H), 2.21 (s, 3H). HRMS (ESI, m / z) calculated for C17H17N2O4S3, 409.03505 (M+H), found 409.03295.

[1147] Synthesis of N-(2-ethyl-3-oxoisoxazolidin-4-yl)-3-methyl-5-(5-methyl-5-phenyl- 1,4,2- oxathiazol-3-yl)thiophene-2-carboxamide (AV-1374). The corresponding 1,4,2-oxathaizole mo, derivative was synthesized using the general procedure reported for the ( \f-sf ot amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV-1365

[1148]

[1149] w / o 'Td^IE‘ (30 mg, 1 equiv.) was dissolved in DMF (0.025 M), and EDCI HC1 (1.1 equiv.), and DMAP (3.5 equiv.) were added, followed by the corresponding amine coupling partner (1.5 equiv.). After purification, desired product was obtained as a clear wax (15.8 mg, 39%). 'H NMR (600 MHz, CDCh) 87.59, 7.57, 7.40, 7.39, 7.38, 7.35, 7.34, 7.32, 7.05, 5.30, 4.95, 4.94, 4.93, 3.73, 3.72, 3.71, 3.70, 3.66, 3.64, 3.63, 3.62, 2.48, 2.19, 2.17, 1.51, 1.51, 1.50, 1.28, 1.27, 1.26, 1.25, 1.25. LRMS (ESI + APCI), 432 (M+H).

[1150] Synthesis of 3-methyl-5-(5-methyl-5-phenyl- l,4,2-oxathiazol-3-yl)-N-(2-oxo-2- ((2,2,2-trifhioroethyl)amino)ethyl)thiophene-2-carboxamide (AV- 1375). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure \ / i i,N

[1151] y_s Ho reported for the amide coupling. The corresponding 1,4,2-oxathiazole

[1152]

[1153] Me o benzoate AV-1365 (30 mg, 1 equiv.) was dissolved in DMF (0.025 M), and EDCI HC1 (1.1 equiv.), and DMAP (3.5 equiv.) were added, followed by the corresponding amine coupling partner (1.5 equiv.). After purification, desired product was obtained as a clear wax (15.8 mg, 39%). 1H NMR (600 MHz, CDC13) 87.59, 7.59, 7.58, 7.57, 7.40, 7.39, 7.38, 7.35, 7.34, 7.33, 7.05, 4.14, 4.13, 4.12, 3.98, 3.96, 3.95, 3.95, 3.94, 3.92, 3.50, 3.49, 3.49, 3.48, 3.47, 3.46, 2.49, 2.47, 2.20, 2.17. LRMS (ESI + APCI), 458 (M+H).Attorney Docket No. 10620-164W02

[1154] NCSURef.: 2025-138-04

[1155] Synthesis of (Z)-N-((methoxyimino)methyl)-3-methyl-5-(5-methyl-5-phenyl- 1,4,2- oxathiazol-3-yl)thiophene-2-carboxamide (1376). The corresponding 1,4,2-oxathaizole mo, derivative was synthesized using the general procedure reported for the N

[1156] _ J /

[1157] ys o. Me amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV- 1365 (7 I H i

[1158] 5 (30 mg, 1 equiv.) was dissolved in DMF (0.025 M), and EDCI HC1 (1.1 equiv.), and DMAP (2 equiv.) were added, followed by the corresponding amine coupling partner (1.5 equiv.). After purification, desired product was obtained as a clear wax (6.0 mg, 17%). 'H NMR (600 MHz, CDCh) 87.74, 7.72, 7.58, 7.57, 7.41, 7.39, 7.38, 7.36, 7.34, 7.33, 7.08, 7.08, 3.92, 2.53, 2.51, 2.21, 2.20, 2.17. LRMS (ESI + APCI), 376 (M+H).

[1159] Synthesis of 3-methyl-5-(5-methyl-5-phenyl- l,4,2-oxathiazol-3-yl)-N-(2-oxo-2- ((2,2,2-trifhioroethyI)amino)ethyI)furan-2-carboxamide (AV-1377). The corresponding 1,4,2- / " Vy+Noxathaizole derivative o o was synthesized using the general procedure

[1160] n reported for the amide coupling. The corresponding 1,4, 2-oxathiazole

[1161]

[1162] Me o CCF3benzoate AV-1366 (11 mg, 1 equiv.) was dissolved in DMF (0.025 M), and EDCI HC1 (1.1 equiv.), and DMAP (2 equiv.) were added, followed by the corresponding amine coupling partner (1.5 equiv.). After purification, desired product was obtained as a clear wax (2.8 mg, 18%). 'H NMR (600 MHz, CDCh) 87.57, 7.56, 7.41, 7.39, 7.39, 7.38, 7.38, 7.36, 7.34, 7.32, 7.30, 6.71, 5.32, 5.31, 5.30, 3.87, 2.55, 2.39, 2.20, 2.17, 1.51, 1.51, 1.50. LRMS (ESI + APCI), 442 (M+H).

[1163] @ Phenyl (AV-1361) (ft) Phenyl (AV-1436) (RJ) Phenyl (AV-1441 ) 3,5-dichlorophenyl (AV-1363) 3,5-dichlorophenyl (AV-1437) 3,5-dichlorophenyl (AV-1442) 3,5-dichloro-4-fluorophenyl (AV-1329) 3,5-dichloro-4-fluorophenyl (AV-1438) 3,5-dichloro-4-fluorophenyl (AV-1443) 3,4,5-trichlorophenyl (AV-1435) 3,4,5-trichlorophenyl (AV-1439) 3,4,5-trichlorophenyl (AV-1444) 3-chloro-5-(trifluoromethyl)phenyl (AV-1328 ) 3-chloro-5-(trifluoromethyl)phenyl (AV-1440) 3-chloro-5-(trifluoromethyl)phenyl (AV-1445)

[1164] 3-chloro-5- z-s N-°.

[1165] H2NARJ)CFosH Phenyl 3,5-dichloro3,5-dichloro-4- 3,4,5-trichloro(trifluoro- phenyl fluorophenyl phenyl EDCI HCI 'j)T 'Smethyl)phenyl - ► (£)-NH yj DMAP r AV-1454 D AV- 1446 AV-1450 MF, 0 °C - R TMeAV-1458 AV- 1462

[1166] ^oNEtSelected examples of 1,4,2-oxathiazoles analogs AV-1459 AV-1455 MeO AV- 1463 AV-1451 AV- 1447

[1167] O AV-1456 AV-1448 AV- 1464 AV-1452 AV-1460 V^N^CF, H3Me' AV-1457 AV-1453 AV- 1461 AV- 1465 AV-1449

[1168]

[1169] Attorney Docket No. 10620-164W02

[1170] NCSURef.: 2025-138-04

[1171] Synthesis of methyl (Z)-5-((hydroxyimino)((2,2,2-trifluoro-l-phenylethyl)thio)methyl)-3-methylthiophene-2-carboxylate (AV- 1361). The target compound was synthesized using General procedures A and / or B for the synthesis of thiohydroximic acids. Chloroxime of AV-1317 (200 mg, 1 equiv), benzyl

[1172]

[1173] 5 mercaptan derivative (1 equiv.) and triethylamine (1 equiv.). Desired product was purified by flash chromatography, and obtained as a waxy solid (240 mg, 89%).1H NMR (600 MHz, CDCh) 87.96, 7.43, 7.42, 7.42, 7.39, 7.39, 7.38, 7.38, 7.38, 7.38, 7.37, 7.37, 7.36, 7.30, 5.37, 5.36, 5.34, 5.33, 3.87, 2.55, 2.54, 1.51, 1.51, 1.51. LRMS (ESI + APCI), 390 (M+H).

[1174] Synthesis of methyl (Z)-5-(((l-(3,5-dichlorophenyl)-2,2,2-trifluoroethyl)thio) (hydroxyimino)methyl)-3-methylthiophene-2-carboxylate (AV- 1363). The target compound was synthesized using General procedures A and / or B for the synthesis of thiohydroximic acids. Chloroxime of AV-1317 (116 mg, 1 equiv), benzyl mercaptan derivative (1 equiv.) and triethylamine (1 equiv.).

[1175]

[1176] Desired product was purified by flash chromatography, and obtained as a waxy solid (102 mg, 56%). 'H NMR (600 MHz, CDCh) 88.07 (s, 1H), 7.39 (t, J= 1.9 Hz, 1H), 7.34 - 7.30 (m, 3H), 7.30 (s, 1H), 3.88 (s, 3H), 2.55 (s, 3H). LRMS (ESI + APCI), 459 (M+H).

[1177] Synthesis of methyl (Z)-5-(((l-(3,5-dichloro-4-fluorophenyl)-2,2,2-trifluoroethyl) thio)(hydroxyimino)methyl)-3-methylthiophene-2-carboxylate (AV-1329). The target compound was synthesized using General procedures A and / or B for the synthesis of thiohydroximic acids. Chloroxime of AV-1317 (200 mg, 1 equiv.), benzyl mercaptan derivative (1 equiv.) and triethylamine

[1178]

[1179] (1 equiv.). Desired product was purified by flash chromatography, and obtained as a pale pink solid (271 mg, 78%). 'HNMR (600 MHz, CDCh) 88.22 (s, 1H), 7.40 (d, J= 6.1 Hz, 2H), 7.31 (d, J= 0.5 Hz, 1H), 3.88 (s, 3H), 2.55 (s, 3H). HRMS (ESI, m / z) calculated for C16H12C12F4NO3S2475.95718 (M+H), found 475.95507.

[1180] Synthesis of methyl (Z)-5-(((l-(3-chloro-5-(trifluoromethyl)phenyl)-2,2,2-trifluoroethyl)thio)(hydroxyimino)methyl)-3-methylthiophene-2-carboxylate (AV-1328).

[1181] The target compound was synthesized using General procedures A and / or B for the synthesis of thiohydroximic acids. Chloroxime of AV-1317 (200

[1182]

[1183] mg, 1 equiv.), benzyl mercaptan derivative (1 equiv.) and triethylamine (1 equiv.). Desired product was purified by flash chromatography, and obtained as a pale pink solid (314 mg, 87%). 'HNMR (600 MHz, CDCh) 88.32 (s, 1H), 7.65 - 7.60 (m, 2H), 7.57 (s, 1H),Attorney Docket No. 10620-164W02

[1184] NCSURef.: 2025-138-04

[1185] 7.30 (d, J= 0.6 Hz, 1H), 5.43 (q, J= 7.9 Hz, 1H), 3.88 (s, 3H), 2.54 (s, 3H). HRMS (ESI, m / z) calculated for C17H13C1F6NO3S2491.99296 (M+H), found 491.99093.

[1186] Synthesis of methyl 3-methyl-5-(5-phenyl-5-(trifluoromethyl)-l,4,2-oxathiazol-3- yl)thiophene-2-carboxylate (AV- 1436). The target compound was synthesized using General procedure for the preparation of 1,4,2- oxathiazoles. Thiohydroximic acid of AV-1361 (240 mg, 0.014 M).

[1187] LRMS (ESI + APCI), 388 (M+H).

[1188] Synthesis of methyl 5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-l,4,2-oxathiazol-3- yl)-3-methylthiophene-2-carboxylate (AV-1437). The target compound was synthesized using General procedure for the preparation of 1,4,2-

[1189]

[1190] oxathiazoles. Thiohydroximic acid of AV-1363 (116 mg, 0.014 M). LRMS (ESI + APCI), 456 (M+H).

[1191] Synthesis of methyl 5-(5-(3,5-dichloro-4-fhiorophenyl)-5-(trifluoromethyl)- 1,4,2- oxathiazol-3-yl)-3-methylthiophene-2-carboxylate (AV-1438). The target compound was synthesized using General procedure for the preparation of 1,4,2-oxathiazoles. Thiohydroximic acid of AV- 1329 (200 mg, 0.014 M). LRMS (ESI + APCI), 473 (M+H).

[1192] Synthesis of methyl 5-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)- l,4,2-oxathiazol-3-yl)-3-methylthiophene-2-carboxylate (AV-1440).

[1193] The target compound was synthesized using General procedure for the

[1194]

[1195] preparation of 1,4,2-oxathiazoles. Thiohydroximic acid of AV-1328 (314 mg, 0.014 M). LRMS (ESI + APCI), 490 (M+H).

[1196] Synthesis of Afoxolaner-Inspired 1,4,2-oxathiazolesAttorney Docket No. 10620-164W02

[1197] NCSURef.: 2025-138-04

[1198]

[1199] Synthesis of methyl-4-((hydroxyimino)methyl)-l-naphthoate (AV- 1296). To a solution of the corresponding aldehyde (900 mg, 1 equiv.) in absolute EtOH (0.1 M) was added hydroxylamine HC1 (1.5 equiv.) and pyridine (3 equiv.) successively at R. T.HThe reaction was stirred overnight. Upon completion, EtOH was removed and

[1200]

[1201] J the residue was suspended in IN HC1. Extracted with EtOAc and the combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to yield the crude mixture of E / Z oximes. Mixture was purified using flash chromatography. Desired product obtained as a white solid (901 mg, 94%.). 'H NMR (600 MHz, CDCk) 88.96 - 8.91 (m, 1H), 8.85 (s, 1H), 8.46 - 8.41 (m, 1H), 8.15 (d, J= 7.6 Hz, 1H), 7.82 (d, J= 7.7 Hz, 1H), 7.79 (s, 1H), 7.69 - 7.59 (m, 2H), 4.02 (s, 3H). HRMS (ESI, m / z) calculated for C13H12NO3, 230.08172 (M+H), found 231.08406.

[1202] Synthesis of methyl-4-((hydroxyimino)((l-phenylethyl)thio)methyl)- 1 -napht hoate (AV-1344). The target compound was synthesized using General procedures A and / or B for the f > synthesis of thiohydroximic acids. Chloroxime of AV-1315 (200 mg, 1 equiv), benzyl mercaptan derivative (1 equiv.) and triethylamine (1 equiv.). g T 1

[1203] Desired product was purified by flash chromatography, and obtained as a colorless oil (223 mg, quant.). 'HNMR (600 MHz, CDCk) 88.88 (dt, J= 8.8, 0.9 Hz, 1H), 8.05 (dt, J= 8.3, 1.1 Hz, 1H), 8.00 (d, J= 7.4Hz, 1H), 7.75 (s, 1H), 7.62 (ddd, J= 8.5, 6.8, 1.3 Hz, 1H), 7.50 (ddd, J= 8.2, 6.8, 1.2 Hz, 1H), 7.20 (d, J= 7.4 Hz, 1H), 7.06 - 6.97 (m, 3H), 6.70 - 6.65 (m, 2H), 4.04 (s, 3H), 1.39 (d, J= 7.2 Hz, 3H). LRMS (ESI + APCI), 366 (M+H).

[1204]

[1205] Attorney Docket No. 10620-164W02

[1206] NCSURef.: 2025-138-04

[1207] Synthesis of methyl 4-(5-methyl-5-phenyl-l,4,2-oxathiazol-3-yl)-l-naphthoate (AV- 1356). The target compound was synthesized using General procedure for the preparation ofN'VH3 1,4,2-oxathiazoles. Thiohydroximic acid of AV-1344 (223 mg, 0.014 M).

[1208] S' f’h

[1209] MeO Desired product was obtained as a yellow oil (164 mg, 71%). 'H NMR (600

[1210]

[1211] MHz, CDCh) 87.94 (s, 1H), 7.33 - 7.27 (m, 4H), 7.23 (ddt, J= 8.6, 6.3, 1.7 Hz, 1H), 7.16 (s, 1H), 4.88 (p, J = 6.9 Hz, 1H), 3.86 (s, 3H), 2.50 (s, 3H), 1.65 (d, J= 7.0 Hz, 3H). LRMS (ESI + APCI), 364 (M+H).

[1212] Synthesis of 4-(5-methy 1-5-pheny 1-1.4.2-oxatliiazol-3-yl)-l -naphthoic acid (AV- 1364). Hydrolysis of methyl ester was performed by dissolving the corresponding ester AV-1357

[1213] (164 mg, 1 equiv.) in THF (0.1 M) and mixture was cooled down to 0 °C. A HCk, solution of 1 M LiOH (10 equiv.) was added and upon completion, reaction

[1214]

[1215] o

[1216] was acidified with IM HC1, and was extracted with DCM. Organic phase was washed with brine, concentrated in vacuo to afford the desired compounds as a white foam (146 mg, 93%) and the crude was used for the next reaction. LRMS (ESI + APCI), 348 (M-H).

[1217] Synthesis of N-(2-ethyl-3-oxoisoxazolidin-4-yl)-4-(5-methyl-5-phenyl-l,4,2- oxathiazol-3-yl)-l-naphthamide (AV- 1368). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV-1364 (30 mg, 1 equiv.) was dissolved in DMF (0.025 M), and EDCI HC1 (1.1 equiv.),

[1218]

[1219] and DMAP (3.5 equiv.) were added, followed by the corresponding amine coupling partner (1.5 equiv.). After purification, desired product was obtained as a white solid (16.1 mg, 41%). ‘HNMR (600 MHz, CDCh) 88.57 - 8.52 (m, 1H), 8.34 - 8.29 (m, 1H), 7.71 - 7.66 (m, 2H), 7.65 - 7.59 (m, 3H), 7.46 - 7.41 (m, 2H), 7.37 (t, J= 7.4 Hz, 1H), 6.54 (d, J= 4.3 Hz, 1H), 2.29 (s, 3H), 1.51 (d, J= 1.0 Hz, 2H), 1.28 (t, J= 7.1 Hz, 3H). LRMS (ESI + APCI), 462 (M+H).

[1220] Synthesis of 4-(5-methyl-5-phenyl- l,4,2-oxathiazol-3-yl)-N-(2-oxo-2-((2,2,2- trifluoroethyl)amino)ethyl)-l-naphthamide (AV-1369). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV- 1364 (30 mg, 1 equiv.) was dissolved in DMF (0.025 M), and EDCI HC1 (1.1 equiv.),

[1221]

[1222] and DMAP (2 equiv.) were added, followed by the corresponding amine coupling partner (1.5 equiv.). After purification, desired product was obtained as a white solid (9.5 mg, 23%). LRMS (ESI + APCI), 488 (M+H).Attorney Docket No. 10620-164W02

[1223] NCSURef.: 2025-138-04

[1224] Synthesis of (Z)-N-((methoxyimino)methyl)-4-(5-methyl-5-phenyl-l,4,2-oxathiazol-3-yl)-l-naphthamide (AV-1370). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV-1364 (30 mg, 1 equiv.)

[1225]

[1226] was dissolved in DMF (0.025 M), and EDCI HC1 (1.1 equiv.), and DMAP (2 equiv.) were added, followed by the corresponding amine coupling partner (1.5 equiv.). After purification, desired product was obtained as a white solid (3.9 mg, 10%). LRMS (ESI + APCI), 406 (M+H).

[1227] £ ZR> * CR3-N.

[1228] ^

[1229] HPTs< S> I U

[1230]

[1231] Synthesis of methyl (Z)-4-((hydroxyimino)((2,2,2-trifluoro-l-phenylethyl)thio)methyl)-l-naphthoate (AV-1355). The target compound was synthesized using General procedures A and / or B for the synthesis of thiohydroximic acids. Chloroxime of AV-1315 (200 mg, 1 equiv), benzyl mercaptan

[1232]

[1233] derivative (1 equiv.) and triethylamine (1 equiv.). Desired product was purified by flash chromatography, and obtained as a white foam (256 mg, quant.).JH NMR (600 MHz, CDCk) 88.94 (dt, 7= 8.6, 1.0 Hz, 1H), 8.13 (d, 7= 7.4 Hz, 1H), 8.04 (s, 1H), 7.96 (dt, J = 8.4, 1.1 Hz, 1H), 7.65 (ddd, J= 8.6, 6.8, 1.3 Hz, 1H), 7.48 (ddd, J= 8.2, 6.8, 1.2 Hz, 1H), 7.38 (d, J= 7.4 Hz, 1H), 7.25 - 7.19 (m, 1H), 7.16 - 7.10 (m, 2H), 6.73 (d, J= 7.7 Hz, 2H), 4.06 (s, 3H). LRMS (ESI + APCI), 420 (M+H).Attorney Docket No. 10620-164W02

[1234] NCSURef.: 2025-138-04

[1235] Synthesis of methyl (Z)-4-(((l-(3-chloro-5-(trifluoromethyl)phenyl)-2,2,2-trifluoroethyl)thio)(hydroxyimino)methyl)-l-naphthoate (AV- 1323). The target compound was synthesized using General procedures A and / or B for the synthesis of thiohydroximic acids. Chloroxime of AV-1315 (200 mg, 1 equiv),

[1236]

[1237] benzyl mercaptan derivative (1 equiv.) and triethylamine (1 equiv.). Desired product was purified by flash chromatography, and obtained as a white foam (338 mg, quant.). 'H NMR (600 MHz, CDCh) 88.96 (dt, J= 8.7, 0.9 Hz, 1H), 8.25 (s, 1H), 8.15 (d, J = 7.4 Hz, 1H), 7.85 - 7.80 (m, 1H), 7.64 (ddd, J= 8.5, 6.9, 1.3 Hz, 1H), 7.46 (ddd, J= 8.2, 6.8, 1.2 Hz, 1H), 7.40 - 7.34 (m, 2H), 6.83 (d, J= 1.9 Hz, 1H), 6.73 (s, 1H), 4.06 (s, 3H). HRMS (ESI, m / z) calculated for C22H15C1F6NO3S, 522.03654 (M+H), found 522.03424.

[1238] Synthesis of methyl (Z)-4-(((l-(3,5-dichloro-4-fhiorophenyl)-2,2,2-trifluoroethyl)thio)(hydroxyimino)methyl)-l-naphthoate (AV- 1326). The target compound was synthesized using General procedures A and / or B for the synthesis of thiohydroximic acids. Chloroxime of AV-1315 (200 mg, 1 equiv),

[1239]

[1240] benzyl mercaptan derivative (1 equiv.) and triethylamine (1 equiv.). Desired product was purified by flash chromatography, and obtained as a white solid (309 mg, 94%). 'H NMR (600 MHz, CDCh) 88.96 (dt, J= 8.7, 1.0 Hz, 1H), 8.17 (d, J= 7.4 Hz, 1H), 8.15 (s, 1H), 7.81 (dt, J= 8.3, 1.0 Hz, 1H), 7.66 (ddd, J= 8.5, 6.8, 1.3 Hz, 1H), 7.49 (ddd, J = 8.3, 6.8, 1.2 Hz, 1H), 7.39 (d, J= 7.4 Hz, 1H), 6.54 (d, J= 6.0 Hz, 2H), 4.06 (s, 3H). HRMS (ESI, m / z) calculated for C21H14C12F4NO3S, 506.00076 (M+H), found 505.99856.

[1241] Synthesis of methyl 4-(5-phenyl-5-(trifluoromethyl)-l,4,2-oxathiazol-3-yl)-l-naphthoate (AV-1359). The target compound was synthesized using General procedure for the preparation of 1,4,2-oxathiazoles. Thiohydroximic acid of AV-1355 (256 mg, 0.014 M). Desired product was obtained as a yellow oil (173 mg, 56%).

[1242]

[1243] 'H NMR (600 MHz, CDCh) 88.92 - 8.86 (m, 1H), 8.52 - 8.48 (m, 1H), 8.12 (d, J= 7.6 Hz, 1H), 7.73 - 7.61 (m, 6H), 7.52 - 7.47 (m, 3H), 4.03 (s, 3H). LRMS (ESI + APCI), 418 (M+H).

[1244] Synthesis of methyl 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-l,4,2-oxathiazol-3-yl)-l-naphthoate (AV- 1334). The target compound was synthesized using General procedure for the preparation of 1,4,2-oxathiazoles.

[1245] Thiohydroximic acid of AV-1323 (338 mg, 0.014 M). Desired product was

[1246]

[1247] obtained as a yellow oil. LRMS (ESI + APCI), 520 (M+H).Attorney Docket No. 10620-164W02

[1248] NCSURef.: 2025-138-04

[1249] Synthesis of methyl 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)- 1,4,2-oxathiazol-3-yl)-l-naphthoate (AV-1469). The target compound was synthesized using General procedure for the preparation of 1,4,2-oxathiazoles. Thiohydroximic acid of AV-1326 (309 mg, 0.014 M). Desired product was obtained as a yellow

[1250]

[1251] oil. LRMS (ESI + APCI), 503 (M+H).

[1252] Synthesis of 4-(5-phenyl-5-(trifluoromethyl)-1,4,2-oxathiazol-3-yl)-1-naphthoic acid (AV-1367). Hydrolysis of methyl ester was performed by dissolving the corresponding ester AV-1357 (173 mg, 1 equiv.) in THF (0.1 M) and mixture was cooled down to 0 °C. A solution of 1 M LiOH (10 equiv.) was added and upon completion, reaction was acidified with IM HC1, and was extracted with DCM. Organic phase was washed with brine, concentrated in vacuo to afford the desired compounds as a white foam (166 mg, quant.) and the crude was used for the next reaction. LRMS (ESI + APCI), 402 (M-H).

[1253] Synthesis of N-(2-ethyl-3-oxoisoxazolidin-4-yl)-4-(5-phenyl-5-(trifluoromethyl)-1,4,2-oxathiazol-3-yl)-1-naphthamide (AV-1371). The corresponding 1,4,2-oxathaizole

[1254] 15 derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV-1364 (30 mg, 1

[1255]

[1256] equiv.) was dissolved in DMF (0.025 M), and EDCI HC1 (1.1 equiv.), and DMAP (3.5 equiv.) were added, followed by the corresponding amine coupling partner (1.5 equiv.). After purification, desired product was obtained as a white solid (9.0 mg, 24%). LRMS (ESI + APCI), 516 (M+H).

[1257] Synthesis of N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)-4-(5-phenyl-5-(trifluoromethyl)-1,4,2-oxathiazol-3-yl)-1-naphthamide (AV-1372). The corresponding 1,4,2- oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV- '= / JP-NH O

[1258] 01364 (30 mg, 1 equiv.) was dissolved in DMF (0.025 M), and EDCI HC1 (1.1

[1259]

[1260] <CF3equiv.), and DMAP (2 equiv.) were added, followed by the corresponding amine coupling partner (1.5 equiv.). After purification, desired product was obtained as a white solid (15.0 mg, 37%). LRMS (ESI + APCI), 542 (M+H).

[1261] Synthesis of (Z)-N-((methoxyimino)methyl)-4-(5-methyl-5-phenyl-l,4,2-oxathiazol-3-yl)-l-naphthamide (AV-1373). The corresponding 1,4,2-oxathaizole derivative was synthesized using the general procedure reported for the amide coupling. The corresponding 1,4,2-oxathiazole benzoate AV-1364 (30 mg, 1 equiv.) was

[1262]

[1263] N\LN°Medissolved in DMF (0.025 M), and EDCI HC1 (1.1 equiv.), and DMAP (2Attorney Docket No. 10620-164W02

[1264] NCSURef.: 2025-138-04

[1265] equiv.) were added, followed by the corresponding amine coupling partner (1.5 equiv.). LRMS (ESI + APCI), 460 (M+H).

[1266] Synthesis of Sarolaner-Inspired 1.4.2-oxathiazoles

[1267] Sarolaner-inspired 1, 4, 2-oxathiazole examples

[1268]

[1269] Synthesis of tert-butyl (E)-5'-((hydroxyimino)methyl)-3'H-spiro[azetidine-3,l'-isobenzofuran]-l-carboxylate (AV-1379). To a solution of the corresponding aldehyde (1.64 g, N'OH1 equiv., carried crude from previous step) in absolute EtOH (0.1 M) was added <\ 1I J hydroxylamine HCI (1.5 equiv.) and pyridine (3 equiv.) successively at R. T. The

[1270]

[1271] goc10 reaction was stirred overnight. Upon completion, EtOH was removed and the residue was suspended in IN HCI. Extracted with EtOAc and the combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to yield the crude mixture of E / Z oximes. Mixture was purified using flash chromatography. Desired product obtained as a white solid (1.21 g mg, 70% over two steps). 'H NMR (600 MHz, CDCh) 88.15 (d, J= 2.3 Hz, 1H), 7.57 (dd, J= 8.0, 1.3 Hz, 1H), 7.48 (d, J= 7.9 Hz, 1H), 7.45 (s, 1H), 7.38 (s, 1H), 5.12 (s, 2H), 4.32 (dd, J= 9.4, 1.1 Hz, 2H), 4.14 (d, J= 9.4 Hz, 2H), 1.48 (s, 9H). LRMS (ESI + APCI), 305 (M+H).

[1272] Synthesis of tert-butyl 5'-(chloro(hydroxyimino)methyl)-3'H-spiro[azetidine-3,l'-isobenzofuran]-l-carboxylate (AV-1380). To a 1 M solution of the benzaldehyde oxime derivative AV-1379 (1.21 g, 1 equiv.) in dry dimethylformamide (0.1 M) at 0 °CC! wasadded one-fifth of the total N-chlorosuccinimide, followed by portion- wise addition of the reagent over one hour (656 mg, 1.2 equiv.). Reaction was allowed

[1273]

[1274] to warm to room temperature and stir for three hours. The mixture was poured on 10 volumes of ice and allowed to melt over time. The mixture was extracted with diethyl ether. Combined organic layers were washed with lithium chloride (5% w / v), brine, dried over anhydrous sodiumAttorney Docket No. 10620-164W02

[1275] NCSURef.: 2025-138-04

[1276] sulfate, filtered, and concentrated in vacuo and used crude for next reaction. LRMS (ESI + APCI), 339 (M+H).

[1277] Synthesis of tert-butyl (Z)-5'-((hydroxyimino)((l-phenylethyl)thio)methyl)-3'H- spiro[azetidine-3,l'-isobenzofuran]-l-carboxylate (AV-1381). The target compound was N'DHCH35synthesized using General procedures A and / or B for the synthesis of thiohydroximic acids. Chloroxime of AV-1380 (200 mg, 1 equiv), benzyl mercaptan derivative (1 equiv.) and triethylamine (1 equiv.). Desired

[1278]

[1279] Boc

[1280] product was purified by flash chromatography, and obtained as a white solid. LRMS (ESI + APCI), 441 (M+H).

[1281] Synthesis of tert-butyl (Z)-5'-(((l-(3,5-dichloro-4-fhiorophenyl)-2,2,2- trifluoroethyl)thio)(hydroxyimino)methyl)-3'H-spiro[azetidine-3,l'-isobenzofuran]-l- carboxylate (AV-1382). The target compound was synthesized using General procedures A and / or B for the synthesis of thiohydroximic acids. Chloroxime of AV- 1380 (200 mg, 1 equiv), benzyl mercaptan derivative (1 equiv.) and

[1282]

[1283] NCi15 triethylamine (1 equiv.). Desired product was purified by flash chromatography, and obtained as a tanned solid. LRMS (ESI + APCI), 581 (M+H).

[1284] Following 1,4,2-oxathiazole cyclizations, carbamate (Boc) protection, and amide couplings of the final products are achieved through the same methods already described herein.

[1285] Following the same synthetic strategy, the following analogs are accessed (AV1521 - AV- 1644).Attorney Docket No. 10620-164W02

[1286] NCSURef.: 2025-138-04

[1287] MnO2 TFA CH2CI2CH2CI2

[1288] (Ej) Phenyl (AV-1507) (Ry Phenyl (AV-1511 ) (Ej) Phenyl (AV-1516) 3,5-dichlorophenyl (AV-1508) 3,5-dichlorophenyl (AV-1512) 3,5-dichlorophenyl (AV-1517) 3,5-dichloro-4-fluorophenyl (AV-1382) 3,5-dichloro-4-fluorophenyl (AV-1513) 3,5-dichloro-4-fluorophenyl (AV-1518) 3,4,5-trichlorophenyl (AV-1509) 3,4,5-trichlorophenyl (AV-1514) 3,4,5-trichlorophenyl (AV-1519) 3-chloro-5-(trifluoromethyl)phenyl (AV-1510) 3-chloro-5-(trifluoromethyl)phenyl (AV-1515) 3-chloro-5-(trifluoromethyl)phenyl (AV-1520)

[1289] R2A R2B R2C R2D R2E R2F R2G R2H R2I R2J R2K R2L (Ph) •! R2M R2N R2O R2P R2Q R2R R2S R2T R2U R2V R2W R2X * R2A R2B R2C R2D R2E R2F R2G R2H R2I R2J R2K R2L (diCIPh) I; R2M R2N R2O R2P R2Q R2R R2S R2T R2U R2V R2W R2X I

[1290] * R2A R2B R2C R2D R2E R2F R2G R2H R2I R2J R2K R2L * R2M R2N R2O R2P R2Q R2R R2S R2T R2U R2V R2W R2X * R2A R2B R2C R2D R2E R2F R2G R2H R2I R2J R2K R2L * R2M R2N R2O R2P R2Q R2R R2S R2T R2U R2V R2W R2X * R2A R2B R2C R2D R2E R2F R2G R2H R2I R2J R2K R2L <CICF3Ph>! R2M R2N R2O R2P R2Q R2R R2S R2T R2U R2V R2W R2X

[1291]

[1292] Synthesis of Icafolin-Inspired 1,4,2-oxathiazoles

[1293] Preparation of 2-mercaptobut-3-en-l-ol. Key intermediate 2-mercaptobut-3-en-l-ol can be prepared by the method described by D. Crich, et. al. J. Org. Chem. 2009, 74, 24, 9422-9427.Attorney Docket No. 10620-164W02

[1294] NCSURef.: 2025-138-04 CSCI2

[1295] Pyridine DMAP

[1296]

[1297] 2-mercaptobut-3-en-1-ol D. Crich, et. al. J. Org. Chem. 2009, 74, 24, 9422-9427

[1298] Preparation of thiohydroximic acids. Preparation of thiohydroximic intermediate can be achieved by the methods described herein this disclosure. Benzaldoximes derivatives can be prepared from corresponding benzaldehyde derivatives, which upon treatment with NCS, can directly afford the corresponding chloroxime intermediates. The chloroximescan be converted to the corresponding thiohydroximic acids upon treatment with 2-mercaptobut-3-en-l-ol, to afford desired product.

[1299] NH2OH Pyridine NCS thiohydroximic EtOH, R. T. DMF TEA, Et2O intermediate

[1300]

[1301] Preparation of icafolin-inspired 1.4.2-oxathiazoles: Thiohydroximic intermediates can be converted to the corresponding 1,4,2-oxathiazoles using an oxidative cycliation, like the one reported in this patent, using Mn02 as the oxidant in a suitable solvent carrier like DCM. Upon cyclization, primary alcohol oxidation can be achieved using a chemoselective method, compatible with presence of an alkene, following a procedure similar to the one reported by L. Huang et. al. (Chemistry 2006;12(20):5246-5252). Upon oxidation, amide bond formation can be achived by following a amide coupling chemistry protocol, for example, using EDCI as a coupling agent, DMAP, and the corresponding amine to yield the final desired compound.

[1302] N-O TEMPO ox. EDCI HCI DMAP DMF, 0 °C - R T L. Huang ef. al. Chemistry

[1303]

[1304] 2006;12(20):5246-5252 Evaluations of Insecticidal Activity (Antitick Immersion Tests)

[1305] The insecticidal activity of example compounds was evaluated using an immersion assay against the lone star tick (Amblyomma americanum). Test compounds were initially prepared as stock solutions (10,000 ppm) and subsequently diluted in DI water to obtain working solutions at desired concentrations, such as 100 ppm and 250 ppm. Aliquots (1 mL) of the diluted solutions were transferred into microcentrifuge tubes. Adult ticks were introduced into the test solutions and subjected to gentle agitation, at approximately 100 rpm, for 3 minutes to ensure uniform exposure. Following treatment, the ticks were removed from the solution, placed on an absorbentAttorney Docket No. 10620-164W02

[1306] NCSURef.: 2025-138-04

[1307] material to remove excess liquid, and allowed to dry. The treated ticks were then transferred to Petri dishes (60 mm diameter) containing a substrate such as fdter paper. Mortality was monitored over time, up to 96 hours post-treatment. Each experimental condition was conducted in multiple replicates of at least five repetitions.

[1308] The results for example compounds are summarized in Figure 1.

[1309] The compounds, compositions, and methods of the appended claims are not limited in scope by the specific compounds, compositions, and methods described herein, which are intended as illustrations of a few aspects of the claims. Any compounds, compositions, and methods that are functionally equivalent are intended to fall within the scope of the claims. Various modifications of the compounds, compositions, and methods in addition to those shown and described herein are intended to fall within the scope of the appended claims. Further, while only certain representative compounds, compositions, and method steps disclosed herein are specifically described, other combinations of the compounds, compositions, and method steps also are intended to fall within the scope of the appended claims, even if not specifically recited. Thus, a combination of steps, elements, components, or constituents may be explicitly mentioned herein or less, however, other combinations of steps, elements, components, and constituents are included, even though not explicitly stated.

[1310] The term “comprising” and variations thereof as used herein is used synonymously with the term “including” and variations thereof and are open, non-limiting terms. Although the terms “comprising” and “including” have been used herein to describe various embodiments, the terms “consisting essentially of’ and “consisting of’ can be used in place of “comprising” and “including” to provide for more specific embodiments of the invention and are also disclosed. Other than where noted, all numbers expressing geometries, dimensions, and so forth used in the specification and claims are to be understood at the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, to be construed in light of the number of significant digits and ordinary rounding approaches.

[1311] Unless defined otherwise, all technical and scientific terms used herein have the same meanings as commonly understood by one of skill in the art to which the disclosed invention belongs. Publications cited herein and the materials for which they are cited are specifically incorporated by reference.

Claims

Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04WHAT IS CLAIMED IS:

1. A compound defined by Formula IV belowFormula IVwhereinA represents an aryl or heteroaryl group;R5represents halogen or haloalkyl;R6represents hydrogen, halogen, or haloalkyl;R7represents halogen or haloalkyl;RAis chosen from hydroxy, halogen, -CN, -NO2, amino, alkylamino, dialkylamino, alkyl, haloalkyl; alkylthio; haloalkylthio; alkoxy, haloalkoxy, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxy carbonyl, haloalkoxy carbonyl, alkylaminocarbonyl, heteroalkylaminocarbonyl, dialkylaminocarbonyl, heterodialkylaminocarbonyl, nitrone, sulfonic acid, sulfonamido, thiol, phosphonate, phosphinyl, aldehyde, trimethylsilyl, hydrazino, azido, isocyanate, aryl, and heteroaryl;n is 0, 1, 2, or 3; andE represents an amido group.

2. The compound of claim 1, wherein the compound comprises one of the followingAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04Cl3. A compound of Formula VIIFormula VIIwhereinY is chosen from S, S=O, and S(=O)2;C-A1, C-A2, C-A3and C-A4are independently of one another C-H, C-(C-R5), or nitrogen;Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04C-G1is oxygen or sulfur;C-L is a single bond or Ci-Cs alkylene;C-R1is hydrogen, C1-C8 alkyl, C1-C8 alkylcarbonyl-, C1-C8 alkoxy, C1-C8 alkoxy-C1-C8 alkyl, or C1-C8 alkoxy carbonyl;C-R2is hydrogen, C1-C8 haloalkyl or C1-C8 alkyl;C-R3is C1-C8 haloalkyl;C-R4is aryl or aryl substituted by one to three C-R6, or C-R4is heterocyclyl or heterocyclyl substituted by one to three C-R6;each C-R5is independently halogen, cyano, nitro, Ci-Cs alkyl, Cs-Cs cycloalkyl, C1-C8 haloalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, Ci-Cs alkoxy, Ci-Cs haloalkoxy, Ci-Cs alkoxy carbonyl-, or two C-R5on adjacent carbon atoms together form a -CH=CH-CH=CH- bridge or a -N=CH-CH=CH- bridge;each C-R6is independently halogen, cyano, nitro, Ci-Cs alkyl, C1-C8 haloalkyl, Ci-Cs alkoxy, or Ci-C 8 haloalkoxy;C-Y1is C(C-R7)(C-R8) or C=O;C-Y2, C-Y3and C-Y4are independently C(C-R7)(C-R8), C=O, N-(C-R9), O, S, SO, or SO2, wherein at least two adjacent ring atoms in the ring formed by C-Y1, C-Y2, C-Y3and C-Y4are heteroatoms;each C-R7and C-R8is independently hydrogen, halogen, Ci-Cs alkyl, or C1-C8 haloalkyl; each C-R9is independently hydrogen, cyano, cyano-Ci-Cs alkyl, Ci-Cs alkyl, C1-C8 haloalkyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, or C3-C8 cycloalkyl-Ci-Cs alkyl, C3-C8 cycloalkyl-Ci-Cs alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, or Cs-Cscycloalkyl-Ci-Cshaloalkyl, Ci-Cs hydroxyalkyl, Ci-Csalkoxy-Ci-Cs alkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 alkynyl, C2-Cs haloalkynyl, phenyl, phenyl substituted by one to three C-R10, phenyl-Ci-C4 alkyl, phenyl-Ci-C4 alkyl wherein the phenyl moiety is substituted by one to three C-R10, 5-6 membered heteroaryl-Ci-C4 alkyl or 5-6 membered heteroaryl-Ci-C4 alkyl wherein the heteroaryl moiety is substituted by one to three C-R10, or Ci-C4alkyl-(Ci-C4alkyl-O-N=)C-CH2-;each C-R10is independently halogen, cyano, nitro, Ci-Cs alkyl, C1-C8 haloalkyl, Ci-Cs alkoxy, or Ci-C 8 haloalkoxy;or a salt or N-oxide thereof.Attorney Docket No. 10620-164W02NCSURef.: 2025-138-044. The compound according to claim 3, wherein the compound is defined by Formula VIIA or a salt thereofNNFormula VIIAwhereinY is chosen from S, S=O, and S(=O)2;C-Y1is C(C-R7)(C-R8) or C=O;C-Y2, C-Y3and C-Y4are independently C(C-R7)(C-R8), C=O, N-(C-R9), O, S, SO, or SO2, wherein at least two adjacent ring atoms in the ring formed by C-Y1, C-Y2, C-Y3and C-Y4are heteroatoms;C-G1is oxygen or sulfur;C-R1is hydrogen, C1-C8 alkyl, C1-C8 alkylcarbonyl-, C1-C8 alkoxy, C1-C8 alkoxy-C1-C8 alkyl, or C1-C8 alkoxy carbonyl;C-R2is hydrogen or C1-C4 alkyl;C-R3is C1-C4 haloalkyl;C-R4is phenyl, or phenyl substituted by one to three C-R6;C-R5is halogen, nitro, C1-C4 alkyl, C3-C4 cycloalkyl, C2-C4 alkenyl or C1-C4 haloalkyl; C-A3and C-A4are independently C-H orN;C-L is a bond or methylene;each C-R7and C-R8is independently hydrogen, halogen, Ci-Cs alkyl, or C1-C8 haloalkyl; each C-R9is independently hydrogen, cyano, cyano-Ci-Cs alkyl, Ci-Cs alkyl, C1-C8 haloalkyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, or C3-C8 cycloalkyl-Ci-Cs alkyl, C3-C8 cycloalkyl-Ci-Cs alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, or Cs-Cscycloalkyl-Ci-Cshaloalkyl, Ci-Cs hydroxyalkyl, Ci-Csalkoxy-Ci-Cs alkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 alkynyl, C2-Cs haloalkynyl, phenyl, phenyl substituted by one to three C-R10, phenyl-Ci-C4 alkyl, phenyl-Ci-C4 alkyl wherein the phenyl moiety is substituted by one to three C-R10, 5-6 memberedAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04heteroaryl-Ci-C4 alkyl or 5-6 membered heteroaryl-Ci-C4 alkyl wherein the heteroaryl moiety is substituted by one to three C-R10, or Ci-C4alkyl-(Ci-C4alkyl-O-N=)C-CH2-;each C-R10is independently halogen, cyano, nitro, C1-C8 alkyl, C1-C8 haloalkyl, C1-C8 alkoxy, or C1-C8 haloalkoxy;or a salt or N-oxide thereof.

5. The compound according to claim 3 or claim 4, wherein C-Y1is C(C-R7)(C-R8).

6. The compound according to any one of 3-5, wherein two of C-Y2, C-Y3and C-Y4in the grouping -C-Y2-C-Y3-C-Y4- together are -S-S-, -S-SO-, -SO-SO-, -SO-SO2-, -SO2-SO2-, -O-N(-C-R9)-, -O-S-, -O-SO-, -O-SO2-, -N(-C-R9)-N(-C-R9)-, -N(-C-R9)-S-, -N(-C-R9)-S(O)- or -N(-C-R9)-SO2-.

7. A compound according to any one of claims 3-6, wherein the grouping -C-Y2-C-Y3-C-Y4- is selected from -C(C-R7)(C-R8)-N(-C-R9)-N(-C-R9)-, -C(C-R7)(C-R8)-N(-C-R9)-O-, -C(C-R7)(C-R8)-N(-C-R9)-S-, -C(C-R7)(C-R8)-N(-C-R9)-SO2-, -C(C-R7)(C-R8)-O-N(-C-R9)-, -C(C-R7)(C-R8)-O-SO-, -C(C-R7)(C-R8)-O-SO2-, -C(C-R7)(C-R8)-S-N(-C-R9)-, -C(C-R7)(C-R8)-S-S-, -C(C-R7)(C-R8)-SO-O-, -C(C-R7)(C-R8)-SO2-N(-C-R9)-, -C(C-R7)(C-R8)-SO2-O-, -C(=O)-N(-C-R9)-N(-C-R9)-, -C(=O)-N(-C-R9)-O-, -C(=O)-N(-C-R9)-S-, -C(=O)-O-N(-C-R9)-, -C(=O)-S-N(-C-R9)-, -N(-C-R9)-N(-C-R9)-C(C-R7)(C-R8)-, -N(-C-R9)-N(-C-R9)-C(=O)-, -N(-C-R9)-O-C(C-R7)(C-R8)-, -N(-C-R9)-O-C(=O)-, -N(-C-R9)-S-C(C-R7)(C-R8)-, -N(-C-R9)-SO-N(-C-R9)-, -N(-C-R9)-SO2-C(C-R7)(C-R8)-, -N(-C-R9)-SO2-N(-C-R9)-, -N(-C-R9)-SO2-O-, -O-N(-C-R9)-C(C-R7)(C-R8)-, -O-N(-C-R9)-C(=O)-, -O-N(-C-R9)-SO-, -O-N(-C-R9)-SO2-, -N(-C-R9)-S-C(C-R7)(C-R8)-, -N(-C-R9)-SO-C(C-R7)(C-R8)-, -N(-C-R9)-SO-N(-C-R9)-, -N(-C-R9)-SO-O-, -N(-C-R9)-SO2-C(C-R7)(C-R8)-, -N(-C-R9)-SO2-N(-C-R9)-, -N(-C-R9)-SO2-O-, -S-N(-C-R9)-C(C-R7)(C-R8)-, -S-N(-C-R9)-C(=O)-, -S-S-C(C-R7)(C-R8)-, -SO-N(-C-R9)-N(-C-R9)-, -SO-O-C(C-R7)(C-R8)-, -SO2-N(-C-R9)-C(C-R7)(C-R8)-, -SO2-N(-C-R9)-N(-C-R9)-, -SO2-N(-C-R9)-O- and -SO2-O-C(C-R7)(C-R8)-.

8. The compound according to any one of claims 3 to 7, wherein C-Y2or C-Y4is C=O.

9. The compound according to any one of claims 3 to 7, wherein C-Y2or C-Y4is C(C-R7)(C-R8).Attorney Docket No. 10620-164W02NCSURef.: 2025-138-0410. The compound according to any one of claims 3 to 7, wherein C-Y2and C-Y4are independently N(-C-R9), O, S, SO, or SO2.

11. A compound according to any one of claims 3 to 7 and 10, wherein C-Y4is C=O or C(C-R7)(C-R8) when C-L is a bond.

12. A compound according to any one of claims 3 to 7 and 11, wherein the grouping -C-Y2-C-Y3-C-Y4- is selected from -O-N(-C-R9)-C(=O)-, -S-S-C(C-R7)(C-R8)-, -S-SO-C(C-R7)(C-R8)-, -O-N(-C-R9)-(C-R7)(C-R8)-, -N(-C-R9)-N(-C-R9)-C(=O)-, -SO2-N(-C-R9)-C(C-R7)(C-R8)-, -C(C-R7)(C-R8)-N(-C-R9)-O-, -C(C-R7)(C-R8)-N(-C-R9)-O-, -C(=O)-N(-C-R9)-O-, -C(=O)-N(-C-R9)-O-, -O-SO-O-, -C(C-R7)(C-R8)-N(-C-R9)-SO2, -N(-C-R9)-SO2-O-, -SO-O-C(C-R7)(C-R8)-and -N(C-R9)-SO-O-.

13. The compound according to any one of claims 3 to 7 and 11, wherein the grouping -C-Y2-C-Y3-C-Y4- is selected from -O-N(-C-R9)-C(=O)-, -S-S-C(C-R7)(C-R8)-, -SO2-N(-C-R9)-C(C-R7)(C-R8)-, -C(C-R7)(C-R8)-N(-C-R9)-O-, -C(=O)-N(-C-R9)-O-, -SO-O-C(C-R7)(C-R8)-and -C(=O)-N(-C-R9)-O-.

14. The compound according to any one of claims 3 to 7 and 11, wherein the grouping -C-Y2-C-Y3-C-Y4- is -O-N(-C-R9)-C(=O)- or -SO-O-C(C-R7)(C-R8)-.

15. The compound according to any one of claims 3-14, wherein C-R9is hydrogen, cyano-Ci-Cs alkyl, Ci-Cs alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, or Ci-Cshaloalkyl, Ci-Cs hydroxyalkyl, C2-C8 alkenyl, C2-CS alkynyl, phenyl-Ci-C4 alkyl or phenyl-Ci-C4 alkyl wherein the phenyl moiety is substituted by one to three C-R10, 5-6 membered heteroaryl-Ci-C4 alkyl or 5-6 membered heteroaryl-Ci-C4 alkyl wherein the heteroaryl moiety is substituted by one to three C-R10, and wherein the heteroaryl is pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl or thiazolyl.

16. The compound according to any one of claims 3-15, wherein the compound is one of the following:Attorney Docket No. 10620-164W02NCSURef.: 2025-138-040Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04where Y is chosen from S, S=O, and S(=O)2.

17. A compound of Formula VIII or a salt thereof:whereinY is chosen from S, S=O, and S(=O)2;D-A1, D-A2and D-A3are carbon;D-G is a benzene ring;D-W is an oxygen atom or sulfur atom;D-X is halogen atom, cyano, nitro, azido, — SCN, — SFs, Ci-Ce alkyl, Ci-Ce alkyl arbitrarily substituted with D-R4, Cs-Cs cycloalkyl, Cs-Cs cycloalkyl arbitrarily substituted withAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04D-R4, C2-C6 alkenyl, C2-C6 alkenyl arbitrarily substituted with D-R4, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C6 alkynyl, C2-C6 alkynyl arbitrarily substituted with D-R4, — OH, — O(D-R5), — OSO2(D-R5), — SH, — S(O)r(D-R5), — N=CHO(D-R8), — N=C(D-R9)O(D-R8), — CHO, — C(O) (D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(O)NH(D-R10), — C(O)N(D-R10) (D-R9), — C(S)O(D-R9), — C(S)S(D-R9), — C(S)NH(D-R10), — C(S)N(D-R10)(D-R9)— CH=NO(D-R11), — C(D-R9)=NO(D-R11), — S(O)2O(D-R9), — S(O)2NH(D-R10), — S(O)2N(D-R10) (D-R9), — Si(D-R13)(D-R14) (D-R12), phenyl, phenyl substituted with (Z)Pi, D-l to D-65, E-l to E-45, when m is 2, 3, 4 or 5, each D-X may be identical with or different from each other,further, when two D-Xs are adjacent, the adjacent two D-Xs may form 5 -membered or 6-membered ring together with carbon atoms to which the two D-Xs are bonded by forming — CH2CH2CH2—, — CH2CH2O—, — CH2OCH2—, — OCH2O—, — CH2CH2S—, — CH2SCH2—, — CH2CH2N(D-R15)—, — CH2N(D-R15)CH2—, — CH2CH2CH2CH2—, — CH2CH2CH2O—, — CH2CH2OCH2—, — CH2OCH2O—, — OCH2CH2O—, — OCH2CH2S—, — CH2CH=CH—, — OCH=CH—, — SCH=CH—, — N(D-R15)CH=CH—, — OCH=N—, — SCH=N—, — N(D-R15)CH=N—, — N(D-R15)N=CH—, — CH=CHCH=CH— or — OCH2CH=CH—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with Z, further when the hydrogen atoms are substituted with two or more Zs at the same time, each Z may be identical with or different from each other;D-Y is halogen atom, cyano, nitro, azido, — SCN, — SFs, Ci-Ce alkyl, Ci-Ce alkyl arbitrarily substituted with D-R4, C3-C8 cycloalkyl, C3-C8 cycloalkyl arbitrarily substituted with D-R4, C2-C6 alkynyl, C2-C6 alkynyl arbitrarily substituted with D-R4, — OH, — O(D-R5), — OSO2(D-R5), — SH, — S(O)r(D-R5), — NH(D-R7), — N(D-R7) (D-R6), — N=CHO(D-R8), — N=C(D-R9)O(D-R8), — C(O)NH(D-R10), — C(O)N(D-R10) (D-R9), — C(S)NH(D-R10), — C(S)N(D-R10) (D-R9), — Si(D-R13)(D-R14)(D-R12), phenyl, phenyl substituted with (Z)Pi, D-l to D-65, E-l to E-45, when n is 2, 3 or 4, each D-Y may be identical with or different from each other,further, when two D-Ys are adjacent, the adjacent two D-Ys may form 5 -membered or 6-membered ring together with carbon atoms to which the two D-Ys are bonded by forming — CH2CH2CH2—, — CH2CH2O—, — CH2OCH2—, — OCH2O—, — CH2CH2S—, — CH2SCH2—, — SCH2S—, — CH2CH2CH2CH2—, — CH2CH2CH2O—, — CH2CH2OCH2—, — CH2OCH2O—, — OCH2CH2O—, — OCH2CH2S—, — SCH2CH2S—, — OCH=N— or — SCH=N—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substitutedAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04with Z, further when the hydrogen atoms are substituted with two or more Zs at the same time, each Z may be identical with or different from each other;D-R1and D-R2independently of each other are hydrogen atom, cyano, C1-C12 alkyl, Ci-C12 alkyl arbitrarily substituted with D-R16, C3-C12 cycloalkyl, C3-C12 cycloalkyl arbitrarily substituted with D-R16, C2-C 12 alkenyl, C2-C12 alkenyl arbitrarily substituted with D-R16, C3-C12 cycloalkenyl, C3-i2halocycloalkenyl, C3-Ci2alkynyl, C3-Ci2alkynyl arbitrarily substituted with D-R16, — S(D-R9), — S(O)2(D-R9), — SN(D-R18) (D-R17), — S(O)2N(D-R10)(D-R9), — O(D-R19), — N(D-R20)(D-R19), — N=CH(D-R19b), — N=C(D-R19b)(D-R19a), — CHO, — C(O)(D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(O)N(D-R10)(D-R9), — C(S)O(D-R9), — C(S)S(D-R9), — C(S)N(D-R10)(D-R9), — C(=N-D-R11)O(D-R9), — C(=N-D-R11)S(D-R9), — C(=N-D-R11)N(D-R10) (D-R9), phenyl, phenyl substituted with (Z)Pi, D-l to D-65, or E-l to E-49,or D-R1and D-R2together form =C(D-R2a)(D-Rla), or D-R1and D-R2together may form 3- to 5-membered ring together with the nitrogen atom bonding them by forming C2-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, Ci-Ce alkyl, Ci-Cehaloalkyl, Ci-Ce alkoxy (Ce)alkyl, Ci-Ce alkoxy, formyl, Ci-Ce alkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci-Ce alkoxy carbonyl, Ci-Ce haloalkoxycarbonyl, Ci-Ce alkylaminocarbonyl, Ci-Ce haloalkylaminocarbonyl, phenyl or phenyl substituted with (Z)Pi, or in case where substituent D-Y is present at the adjacent position, D-R2together with D-Y may form a 5-membered ring together with the atom bonding them by forming — CH2 —, — CH2CH2 —, — CH2O —, — CH2S —, — CH2N(D-R6) —, — CH=CH — or — CH=N —, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, Ci-C ealkyl, Ci-Ce haloalky 1, Ci-Ce alkylidene, Ci-Cehaloalkylidene, oxo orthioxo,D-Rlaand D-R2atogether may form a 5- or 6-membered ring together with the carbon atom bonding them by forming C4-C5 alkylene chain or C4-C5 alkenylene chain, in this case, the alkylene chain and the alkenylene chain may contain one to three oxygen atoms or sulfur atoms, or D-Rlaand D-R2atogether may form a 5-membered ring together with the carbon atom bonding them by forming C4 alkylene chain or C4 alkenylene chain, in this case, the alkylene chain and the alkenylene chain may contain one to three nitrogen atoms, and either ring may be arbitrarily substituted with halogen atom, Ci-Ce alkyl, Ci-Cehaloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Ci-Ce alkylthio or Ci-Cehaloalkylthio;D-R3is cyano, Ci-Ce alkyl arbitrarily substituted with D-R4, C3-C8 cycloalkyl, C3-C8 cycloalkyl arbitrarily substituted with D-R4, C3-C6 alkenyl, C2-C6 alkenyl arbitrarily substitutedAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04with D-R4, C3-C6 alkynyl, C2-C6 alkynyl arbitrarily substituted with D-R4, — O(D-R5), — S(O)r(D-R5), — N(D-R10)(D-R9), — CHO, — C(O)(D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(O)NH(D-R10), — C(O)N(D-R10)(D-R9), — C(S)O(D-R9), — C(S)S(D-R9), — C(S)NH(D-R10), — C(S)N(D-R10)(D-R9), — CH=NO(D-Rn), — C(D-R9)=NO(D-Rn), — Si(D-R13)(D-R14)(D-R12), — P(O)(O-D-R21)2, phenyl, phenyl substituted with (Z)Pi, D-l to D-65, or E-l to E-45;D-l to D-65 are aromatic heterocyclic rings of the following formulae, respectivelyAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04Z is halogen atom, cyano, nitro, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4haloalkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Ci-C4haloalkylthio Ci-C4alkyl, Ci-C4alkylsulfinyl Ci-C4alkyl, Ci-C4haloalkylsulfinyl Ci-C4alkyl, Ci-C4alkylsulfonyl Ci-C4alkyl, Ci-C4haloalkylsulfonyl Ci-C4alkyl, Cs-Cecycloalkyl, Cs-Cehalocycloalkyl, — OH, Ci-Cealkoxy, Ci-Cehaloalkoxy, Ci-Cealkylsulfonyloxy, Ci-Cehaloalkylsulfonyloxy, Ci-Cealkylthio, Ci-Cehaloalkylthio, Ci-Cealkylsulfinyl, Ci-Cehaloalkylsulfinyl, Ci-Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl, — NH2, Ci-Cealkylamino, di(Ci-C6alkyl)amino, Ci-Cealkoxycarbonyl, Ci-Cehaloalkoxycarbonyl, — C(O)NH2, Ci-Cealkylaminocarbonyl, Ci-Cehaloalkylaminocarbonyl, di(Ci-C6alkyl)aminocarbonyl, — C(S)NH2, — S(O)2NH2, Ci-Cealkylaminosulfonyl, di(Ci-C6alkyl)aminosulfonyl, phenyl or phenyl arbitrarily substituted with halogen atom, when pl, p2, p3 or p4 is an integer of 2 or more, each Z may be identical with or different from each other, further, when two Zs are adjacent, the adjacent two Zs may form 5-membered or 6-membered ring together with carbon atoms to which the two Zs are bonded by forming — CH2CH2CH2 —,Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04— CH2CH2O—, — CH2OCH2— — OCH2O—, — CH2CH2S—, — CH2SCH2—, — CH2CH2CH2CH2—, — CH2CH2CH2O—, — CH2CH2OCH2—, — CH2OCH2O—, — OCH2CH2O—, — CH2CH2CH2S—, — OCH2CH2S— or — CH=CH— CH=CH—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, cyano, nitro, Ci-C4alkyl, Ci-C-ihaloalkyl. Ci-C4alkoxy or Ci-C4alkylthio;E-l to E-49 are saturated heterocyclic rings of the following formulae, respectivelyE4 IMAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04D-R4is halogen atom, cyano, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, — OH, — O(D-R5), — SH, — S(O)r(D-R5), — N(D-R10)(D-R9), — N(D-R10)CHO, — N(D-R10)C(O)(D-R9), — N(D-R10)C(O)O(D-R9), — N(D-R10)C(O)S(D-R9), — N(D-R10)C(S)O(D-R9), — N(D-R10)C(S)S(D-R9), — N(D-R10)S(O)2(D-R9), — C(O)O(D-R9), — C(O)N(D-R10) (D-R9), — Si(D-R13)(D-R14) (D-R12), phenyl, phenyl substituted with (Z)PiD-l to D-65, or E-l to E-45;D-R5is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R24, Cs-Cscycloalkyl, C3-Cscycloalkyl arbitrarily substituted with D-R24, C2-Cealkenyl, C2-Cealkenyl arbitrarily substituted with D-R24, Cs-Cscycloalkenyl, Cs-Cshalocycloalkenyl, Cs-Cealkynyl, Cs-Cealkynyl arbitrarily substituted with D-R24, Ci-Cealkylcarbonyl, Ci-Cealkoxy carbonyl, phenyl, phenyl substituted with (Z)Pi, D-l to D-65, or E-l to E-45;D-R6is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R24, Cs-Cecycloalkyl, C3-Cshalocycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, — OH, Ci-Cealkylcarbonyloxy, Ci-Cealkylthio, Ci-Cehaloalkylthio, phenylthio, phenylthio substituted with (Z)Pi, — SN(D-R18) (D-R17), — S(O)2(D-R9), — S(O)2N(D-R10) (D-R9), — CHO, — C(O)(D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(O)NH(D-R10), — C(O)N(D-R10)(D-R9), — C(S)O(D-R9), — C(S)S(D-R9), — C(S)NH(D-R10), — C(S)N(D-R10) (D-R9), — C(O)C(O) (D-R9), — C(O)C(O)O(D-R9), — P(O)(O-D-R21)2or — P(S)(O-D-R21)2;D-R7is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cscycloalkyl Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, C1-C4 alkylthio Ci-C4alkyl, Cs-Cscycloalkyl, Cs-Cealkenyl, CsCehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, — CHO, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl or Ci-Cealkoxy carbonyl, or D-R7together with D-R6may form 3- to 5-membered ring with the bonding nitrogen atom by forming C2-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, oxo or thioxo;D-R8is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cealkenyl, phenyl or phenyl substituted with (z)Pi;D-R9is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R24, Cs-Cscycloalkyl, C3-Cshalocycloalkyl, C2-Cealkenyl, C2-C6haloalkenyl, C2-Cealkynyl, C2-C6haloalkynyl, phenyl, phenyl substituted with (Z)PiD-l to D-65, or E-l to E-45;D-R10is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-Cealkoxy Ci-C4alkyl, Ci-Cealkylthio Ci-C4alkyl, cyano Ci-Cealkyl, Cs-Cealkenyl or C3-Cealkynyl, D-R10together with D-R9may form a 3- to 7-membered ring with the atom bondingAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04them by forming a C2-Cealkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, or D-R10together with D-R9may form a 3- to 5-membered ring with the atom bonding them by forming a C2-C4alkylene chain, in this case, the alkylene chain may contain one nitrogen atom, and either ring may be arbitrarily substituted with halogen atom, Ci-Cealkyl or Ci-Cehaloalkoxy, formyl, Ci-Cealkylcarbonyl or Ci-Cealkoxycarbonyl;D-R11is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, phenyl or phenyl that may be substituted with (Z)Pi, D-R11together with D-R9may form 5- to 7-membered ring with the atom bonding them by forming C2-C4alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, or D-R11together with D-R9may form a 5-membered ring with the atom bonding them by forming C2-alkylene chain, in this case, the alkylene chain may contain one nitrogen, and either ring may be arbitrarily substituted with halogen atom, Ci-Cealkyl or Ci-Cehaloalkyl;D-R12is Ci-Cealkyl, Ci-Cehaloalkyl, phenyl or phenyl substituted with (Z)Pi;D-R13and D-R14independently of each other are Ci-Cealkyl or Ci-Cehaloalkyl;R15is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-Cealkoxycarbonyl Ci-C4alkyl, Ci-Cehaloalkoxycarbonyl Ci-C4alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, Ci-Cealkoxy, Ci-Cealkoxycarbonyl, Ci-Cehaloalkoxy carbonyl, phenyl or phenyl substituted with (Z)Pi, further, in case where Z is present in an adjacent position of R15, the adjacent R15and Z may form 6-membered ring together with the atom bonding them by forming — CH2CH2CH2CH2 — or — CH=CH — CH=CH —, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, Ci-C4alkyl or Ci-C4haloalkyl;D-R16is halogen atom, cyano, nitro, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, hydroxy C3-Cecycloalkyl, Ci-C4alkoxy Cs-Cecycloalkyl, Cs-Cecycloalkenyl, — O25, — N(D-R26) (D-R25), — SH, — S(O)r(D-R27), — SO2OH, — SO2NH(D-R29), — SO2N(D-R29) (D-R28), — CHO, — C(O) (D-R28), — C(O)OH, — C(O)O(D-R28), — C(O)S(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(O)N(D-R29)O(D-R28), — C(O)N(D-R29)N(D-R28a) (D-R28), — C(S)O(D-R28), — C(S)S(D-R28), — C(S)NH(D-R29), — C(S)N(D-R29) (D-R28), — C(O)C(O)O(D-R28), — C(D-R31)=NOH, — C(D-R31)=NO(D-R30), — C(=N-D-R31)O(D-R30), — C(=N-D-R31)S(D-R30), — C(=N-D-R31)N(D-R29) (D-R30), — C(=NO-D-R31)NH(D-R29), — C(=NO-D-R31)N(D-R29) (D-R30), — Si(D-R13)(D-R14) (D-R12), — P(O)(O-D-R21)2, — P(S)(O-D-R21)2, — P(phenyl)2, —Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04P(0)(phenyl)2, phenyl, phenyl substituted with (Z)Pi, naphthyl D-l to D-65, E-l to E-45, or M-l to M-ll;M-l to M-l 1 are partially saturated heterocyclic rings of the following formulae, respectivelyM-3 M-4 M-5M*8 meM41 M42M46 M47 M4S M49 M-20Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04D-R17is Ci- alkyl, Ci-C haloalkyl, Ci- alkoxy Ci- alkyl, cyano Ci-i2alkyl, Ci-nalkoxy carbonyl Ci-i2alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, C3-C alkenyl, C3-Ci2haloalkenyl, Cs-C alkynyl, Cs-C haloalkynyl, Ci-C alkylcarbonyl, Ci-C alkoxy carbonyl, — C(O)ON=C(CH3)SCH3, — C(O)ON=C(SCH3)C(O)N(CH3)2, phenyl or phenyl substituted with (Z)Pi;D-R18is Ci-C alkyl, Ci-Ci2haloalkyl, Ci- alkoxy Ci- alkyl, cyano Ci- alkyl, Ci-C alkoxy carbonyl Ci- alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, C3-C alkenyl, Cs- haloalkenyl, Cs-C alkynyl, Cs-C haloalkynyl, phenyl or phenyl substituted with (Z)Pi, or D-R18together with D-R17may form a 5-membered ring with the nitrogen atom bonding them by forming C4alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, and may be arbitrarily substituted with Ci-C4alkyl or Ci-C4alkoxy;D-R19is hydrogen atom, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R16, C3-Cscycloalkyl, Cs-Cshalocycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, C3-Cehaloalkynyl, — CHO, — C(O)(D-R28), — C(O)O(D-R28), — C(O)S(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(S)O(D-R28), — C(S)S(D-R28), — C(S)NH(D-R29), — C(S)N(D-R29) (D-R28), — S(O)2(D-R28), — S(O)2NH(D-R29), — S(O)2N(D-R29) (D-R28), — P(O)(O-D-R21)2, — P(S)(O-D-R21)2, phenyl, phenyl substituted with (Z)Pi, D-1 to D-65, or E-1 to E-49;D-R19ais hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Ci-C4alkylsulfonyl Ci-C4alkyl, Ci-C4alkoxycarbonyl Ci-C4alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Cecycloalkyl, phenyl C2-C4alkenyl, di(Ci-C6alkyl)amino, phenyl, or phenyl substituted with (Z)PiD-l to D-65, or E-l to E-45;D-R19bis hydrogen atom, Ci-Cealkyl, Ci-Cealkoxy, Ci-Cealkylthio or di(Ci-C6alkyl)amino, or D-R19atogether with D-R19bmay form a 4- to 6-membered ring with the carbon atom bonding them by forming Cs-Csalkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, or D-R19atogether with D-R19bmay form a 4- to 5-membered ring with the carbon atom bonding them by forming Cs-Ctialkylene chain, in this case, the alkylene chain may contain one nitrogen, and either ring may be arbitrarily substituted with halogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, formyl, Ci-Cealkylcarbonyl or Ci-Cealkoxycarbonyl;D-R20is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4haloalkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Ci-C4haloalkylthio Ci-C4alkyl, Ci-C4alkylsulfonyl Ci-C4alkyl, Ci-C4haloalkylsulfonyl Ci-C4alkyl, cyano Ci-Cealkyl, Ci-C4alkoxycarbonyl Ci-C4alkyl, phenyl Ci-C4alkyl, C2-Cealkenyl, C2-Cehaloalkenyl, Cs-Cealkynyl, C3-C6haloalkynyl, —CHO, — C(O) (D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(S)O(D-R9),Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04— C(S)S(D-R9), Ci-Cealkylsulfonyl or Ci-Cehaloalkylsulfonyl, or D-R20together with D-R19may form a 5-membered ring with the nitrogen atom bonding them by forming C4alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with Ci-Cealkyl, Ci-Cealkoxy Ci-Cealkyl, — CHO, Ci-Cealkylcarbonyl or Ci-Cealkoxycarbonyl;D-R21is Ci-Cealkyl or Ci-Cehaloalkyl;D-R22is halogen atom, cyano, Ci-Cealkyl, Ci-Cehaloalkyl, hydroxy Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkoxy carbonyl Ci-C4alkyl, Ci-Cealkoxy, Ci-Cealkylthio, Ci-Cealkylamino, di(Ci-C4alkyl)amino, Ci-Cealkoxy carbonyl, phenyl or phenyl substituted with (Z)Pi, when ql, q2, q3 or q4 is an integer of 2 or more, each D-R22may be identical with or different from each other, further in case where two D-R22s are present on the same carbon atom, the two D-R22S together may form oxo, thioxo, imino, Ci-Cealkylimino, Ci-Cealkoxyimino or Ci-Cealkylidene;R23is hydrogen atom, Ci-Cealkyl, Ci-Cealkyl substituted with D-R32, Cs-Cecycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, — OH, benzyloxy, — CHO, — C(O) (D-R33), — C(O)O(D-R33), — C(O)S(D-R33), — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), — C(S)NH(D-R34), — C(S)N(D-R34) (D-R33), — S(O)2(D-R33), — P(O)(O-D-R21)2, — P(S)(O-D-R21)2, phenyl, phenyl substituted with (Z)Pior D-5;D-R24is halogen atom, cyano, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, Ci-Cealkoxy, Ci-Cehaloalkoxy, Ci-Cealkylthio, Ci-Cehaloalkylthio, Ci-Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl, Ci-Cealkylamino, di(Ci-C6alkyl)amino, — CHO, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci-Cealkoxycarbonyl, Ci-Cehaloalkoxycarbonyl, Ci-Cealkylaminocarbonyl, di(Ci-C6alkyl)aminocarbonyl, phenyl or phenyl substituted with (Z)PiD-l to D-65, or E-l to E-49;D-R25is hydrogen atom, Ci-Csalkyl, Ci-Csalkyl arbitrarily substituted with D-R32, C3-Cscycloalkyl, Cs-Cscycloalkyl arbitrarily substituted with D-R32, Cs-Csalkenyl, Cs-Csalkenyl arbitrarily substituted with D-R32, Cs-Csalkynyl. Cs-Csalkynyl arbitrarily substituted with D-R32, —CHO, — C(O)(D-R33), — C(O)O(D-R33), — C(O)S(D-R33), — C(O)NH(D-R34), C(O)N(D-R34) (D-R33), — C(O)C(O) (D-R33), — C(O)C(O)O(D-R33), — C(S) (D-R33), — C(S)O(D-R33), — C(S)S(D-R33), — C(S)NH(D-R34), — C(S)N(D-R34) (D-R33), — S(O)2(D-R33), — S(O)2N(D-R34) (D-R33), — Si(D-R13)(D-R14) (D-R12), — P(O)(O-D-R21)2, — P(S)(O-D-R21)2, phenyl, phenyl substituted with (Z)Pi, D-l to D-65, or E-l to E-49;D-R26is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Cs-Cecycloalkyl, Cs-Cealkenyl, Cs-Cealkynyl, Ci-Cealkoxy, phenyl orAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04phenyl substituted with (Z)Pi, or D-R26together with D-R25may form 3- to 5-membered ring with the nitrogen atom bonding them by forming C2-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be substituted with halogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-Cealkoxy, phenyl, phenyl substituted with (Z)Pi, oxo or thioxo;D-R27is Ci-Csalkyl, Ci-Csalkyl arbitrarily substituted with D-R32, Cs-Cscycloalkyl, C3-scycloalkyl arbitrarily substituted with D-R32, Cs-Csalkenyl. Cs-Csalkenyl arbitrarily substituted with D-R32, Cs-Csalkynyl, Cs-Csalkynyl arbitrarily substituted with D-R32, — SH, Ci-Cealkylthio, Ci-Cehaloalkylthio, phenylthio, phenylthio substituted with (Z)Pi, — CHO, — C(O) (D-R33), — C(O)O(D-R33), — C(O)S(D-R33), — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), — C(O)C(O) (D-R33), — C(O)C(O)O(D-R33), — C(S) (D-R33), — C(S)O(D-R33), — C(S)S(D-R33), — C(S)NH(D-R34), — C(S)N(D-R34) (D-R33), — P(O)(O-D-R21)2, — P(S)(O-D-R21)2, phenyl, phenyl substituted with (Z)Pi, D-l to D-65, or E-l to E-49;D-R28is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R32, Cs-Cscycloalkyl, Cs-Cscycloalkyl arbitrarily substituted with D-R32, C2-Cealkenyl Cs-Cscycloalkyl, C2-Cehaloalkenyl Cs-Cscycloalkyl, C -Csalkenyl, C -Csalkenyl arbitrarily substituted with D-R32, C2-Csalkynyl, C2-C8alkynyl arbitrarily substituted with D-R32, phenyl or phenyl substituted with (Z)PiD-l to D-65, or E-l to E-49;D-R28ais hydrogen atom or Ci-Cealkyl;D-R29is hydrogen atom, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R32, C3-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, phenyl or phenyl substituted with (Z)Pi, or D-R29together with D-R28may form 3- to 5-membered ring with the nitrogen atom bonding them by forming C2-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, Ci-Cealkyl, Ci-Cealkoxy, formyl, Ci-Cealkylcarbonyl, Ci-Cealkoxycarbonyl, phenyl or phenyl substituted with (Z)Pi;D-R30is Ci-Csalkyl, Ci-Csalkyl arbitrarily substituted with D-R32, Cs-Cscycloalkyl, C3-Csalkenyl, Cs-Csalkenyl arbitrarily substituted with D-R32, Cs-Csalkynyl, Cs-Csalkynyl arbitrarily substituted with D-R32;D-R31is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-Cealkoxy Ci-C4alkyl, Ci-Cehaloalkoxy Ci-C4alkyl, Ci-Cealkylthio Ci-C4alkyl, Ci-Cehaloalkylthio Ci-C4alkyl, Ci-Cealkylsulfonyl Ci-C4alkyl, Ci-Cehaloalkylsulfonyl Ci-C4alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Cecycloalkyl, phenyl or phenylAttomey Docket No. 10620-164W02NCSURef.: 2025-138-04substituted with (Z)Pi, or D-R31together with D-R30may form 5- to 7-membered ring with the atom bonding them by forming C2-C4alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, or D-R31together with D-R30may form a 5-membered ring with the atom bonding them by forming C2alkylene chain, in this case, the alkylene chain may contain one nitrogen, and either ring may be arbitrarily substituted with halogen atom, Ci-Cealkyl or Ci-Cehaloalkyl;D-R32is halogen atom, cyano, nitro, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, — OH, — O(D-R33), — OC(O) (D-R33), — OC(O)O(D-R33), — OC(O)NH(D-R34), — OC(O)N(D-R34) (D-R33), — OC(S)NH(D-R34), — OC(S)N(D-R34) (D-R33), — SH, — S(O)r(D-R33), — SC(O) (D-R33), — SC(O)O(D-R33), — SC(O)NH(D-R34), — SC(O)N(D-R34) (D-R33), — SC(S)NH(D-R34), — SC(S)N(D-R34) (D-R33), — NH(D-R34), — N(D-R34) (D-R33), — N(D-R34)CHO, — N(D-R34)C(O) (D-R33), — N(D-R34)C(O)O(D-R33), — N(D-R34)C(O)NH(D-R34), — N(D-R34)C(O)N(D-R34) (D-R33), — N(D-R34)C(S)NH(D-R34), — N(D-R34)C(S)N(D-R34) (D-R33), — CHO, — C(O) (D-R33), — C(O)O(D-R33), — C(O)S(D-R33), — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), — C(O)C(O)O(D-R33), — Si(D-R13)(D-R14) (D-R12), — P(O)(O-D-R21)2, — P(S)(O-D-R21)2, — P(phenyl)₂, — P(O)(phenyl)₂, phenyl, phenyl substituted with (Z)Pi, D-l to D-65, or E-l to E49;D-R33is Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkyl arbitrarily substituted with D-R35, C3-Cecycloalkyl, Cs-Cehalocycloalkyl, C2-Cealkenyl Cs-Cscycloalkyl, C2-Cehaloalkenyl C3-Cscycloalkyl, C2-Csalkenyl, C2-Cshaloalkenyl, Cs-Cscycloalkenyl, Cs-Cshalocycloalkenyl, C2-Csalkynyl. C2-C8haloalkynyl, phenyl or phenyl substituted with (Z)Pi, D-l to D-65, or E-l to E-49;D-R34is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cscycloalkyl, Cs-Cealkenyl, C3-Cealkynyl, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci-Cealkoxycarbonyl, Ci-Cehaloalkoxycarbonyl, phenoxycarbonyl, phenoxy carbonyl substituted with (Z)Pi, phenylcarbonyl, phenylcarbonyl substituted with (Z)Pi, Ci-Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl, phenyl, phenyl substituted with (Z)Pi, D-l to D-65, or D-R34together with D-R33may form 3- to 5 -membered ring with the nitrogen atom bonding them by forming C2-Csalkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, Ci-Cealkyl, Ci-Cealkoxy, formyl, Ci-Cealkylcarbonyl, Ci-Cealkoxycarbonyl, phenyl or phenyl substituted with (Z)Pi;D-R35is cyano, Cs-Cecycloalkyl, Cs-Cehalocylcoalkyl, E-l to E-49, Ci-C4alkoxy, Ci-C4haloalkoxy, Ci-C4alkylthio, Ci-C4haloalkylthio, Ci-C4alkylsulfonyl, Ci-C4haloalkylsulfonyl, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci-Cealkoxycarbonyl, di(Ci-Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04C6alkyl)aminocarbonyl, tri(Ci-C6alkyl)silyl, phenyl, phenyl substituted with (Z)Pi, or D-l to D-65;m is an integer of 0 to 5;n is an integer of 0 to 4;pl is an integer of 1 to 5;p2 is an integer of 0 to 4;p3 is an integer of 0 to 3;p4 is an integer of 0 to 2;p5 is an integer of 0 or 1;ql is an integer of 0 to 3;q2 is an integer of 0 to 5;q3 is an integer of 0 to 7;q4 is an integer of 0 to 9;r is an integer of 0 to 2; andt is an integer of 0 or 1.

18. The compound of claim 17, whereinD-G is a benzene ring;D-X is halogen atom, cyano, nitro, — SFs, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-(D-R4), Cs-Cscycloalkyl, Cs-Cscycloalkyl arbitrarily substituted with D-R4, C2-Cealkenyl, C2-Cealkenyl arbitrarily substituted with D-R4, C2-Cealkynyl, C2-Cealkynyl arbitrarily substituted with D-R4, —OH, — O(D-R5), — OSO2(D-R5), — S(O)r(D-R5), — C(O)O(D-R9), — C(O)S(D-R9), — C(O)NH(D-R10), — C(O)N(D-R10) (D-R9), — C(S)O(D-R9), — C(S)S(D-R9), — C(S)NH(D-R10), — C(S)N(D-R10) (D-R9), — CH=NO(D-R11), — C(D-R9)=NO(D-R11), — S(O)2NH(D-R10), — S(O)2N(D-R10) (D-R9), — Si(D-R13)(D-R14) (D-R12), phenyl, phenyl substituted with (Z)Pi, D-l to D-46, E-l to E-28, E-32 to E-38 or E-43 to E-45, when m is an integer of 2 or more, each D-X may be identical with or different from each other, further, when two D-Xs are adjacent, the adjacent two D-Xs may form 5-membered or 6-membered ring together with carbon atoms to which the two D-Xs are bonded by forming — CH2CH2CH2 —, — CH2CH2O—, — CH2OCH2—, — OCH2O—, — CH2CH2S—, — CH2SCH2—, — CH2CH2CH2CH2—, — CH2CH2CH2O—, — CH2CH2OCH2—, — CH2OCH2O—, — OCH2CH2O —, — OCH2CH2S — or — CH=CHCH=CH —, in this case, hydrogen atoms bondedAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, Ci-C4alkyl or C1-C4haloalkyl,D-Y is halogen atom, cyano, nitro, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R4, — O(D-R5), — OSO2(D-R5), — S(O)r(D-R5), — NH(D-R7), — N(D-R7) (D-R6), — N=CHO(D-R8), — N=C(D-R9)O(D-R8), — C(O)NH(D-R10), — C(O)N(D-R10) (D-R9), — C(S)NH(D-R10), — C(S)N(D-R10) (D-R9), phenyl, phenyl substituted with (Z)Pi, D-l to D-24, D-30 to D-38 or D-43 to D-46, when n is an integer of 2 or more, each D-Y may be identical with or different from each other,further, when two D-Ys are adjacent, the adjacent two D-Ys may form 5 -membered or 6-membered ring together with carbon atoms to which the two D-Ys are bonded by forming — CH2CH2CH2—, — CH2CH2O—, — CH2OCH2—, — OCH2O—, — CH2CH2CH2CH2—, — CH2CH2CH2O—, — CH2CH2OCH2—, — CH2OCH2O—, — OCH2CH2O—, — OCH=N— or — SCH=N —, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, Ci-C4alkyl or Ci-C4haloalkyl,D-R1is Ci-Csalkyl, Ci-Csalkyl arbitrarily substituted with D-R16, Cs-Cscycloalkyl, C3-Cshalocycloalkyl, Cs-Csalkenyl, Cs-Cshaloalkenyl, phenyl Cs-Cealkenyl, phenyl Cs-Cealkenyl substituted with (Z)Pi, Cs-Csalkynyl, Cs-Cshaloalkynyl, phenyl Cs-Cealkynyl, phenyl C3-Cealkynyl substituted with (Z)Pi, Ci-Csalkoxy, — N(D-R20) (D-R19), — N=CH(D-R19b), — N=C(D-R19b) (D-R19a), — C(O)N(D-R10) (D-R9), — C(S)N(D-R10) (D-R9), — C(=N-D-R11)O(D-R9), — C(=N-D-R11)S(D-R9), — C(=N-D-R11)N(D-R10) (D-R9), phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-6 to D-l 8, D-21 to D-23, D-26 to D-40, D-42, D-45 to D-46, E-4 to E-9, E-23 to E-28, E-34 or E-45,D-R2is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4haloalkoxy Ci-C4alkyl, benzyloxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Ci-C4haloalkylthio Ci-C4alkyl, Ci-C4alkylsulfonyl Ci-C4alkyl, Ci-C4haloalkylsulfonyl Ci-C4alkyl, phenylthio Ci-c 4alkyl, phenylthio Ci-C4alkyl substituted with (Z)Pi, cyano Ci-Cealkyl, nitro Ci-Cealkyl, Ci-C4alkylcarbonyl Ci-C4alkyl, Ci-C4alkoxy carbonyl Ci-C4alkyl, C3-Cecycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, — S(D-R9), — S(O)2(D-R9), — SN(D-R18) (D-R17), —OH, — O(D-R19), — NH(D-R20), — N(D-R20) (D-R19), — N=CH(D-R19b), — N=C(D-R19b) (D-R19a), — C(O) (D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(S)O(D-R9) or — C(S)S(D-R9);or D-R1and D-R2together form =C(D-R2a) (D-Rla), and further D-R1and D-R2together may form 3- to 5-membered ring together with the nitrogen atom bonding them by forming C2 toAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with Ci-Cealkyl, formyl, Ci-Cealkylcarbonyl or Ci-Cealkoxy carbonyl,D-R1aand D-R2atogether may form 5- or 6-membered ring together with the carbon atom bonding them by forming C4or C5alkylene chain or C4or C5alkenylene chain, in this case, the alkylene chain and the alkenylene chain may contain one to three oxygen atoms or sulfur atoms, or D-Rlaand D-R2atogether may form a 5-membered ring together with the carbon atom bonding them by forming C4 alkylene chain or C4 alkenylene chain, in this case, the alkylene chain and the alkenylene chain may contain one to three nitrogen atoms, and either ring may be arbitrarily substituted with halogen atom or Ci-Cealkyl,D-R3is cyano, Ci-Cealkyl arbitrarily substituted with D-R4, Cs-Cscycloalkyl, C3-Cshalocycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, — O(D-R5), — S(O)r(D-R5), — N(D-R10) (D-R9), — C(O)O(D-R9), C(O)S(D-R9), — C(O)NH(D-R10), — C(O)N(D-R10) (D-R9), — C(S)O(D-R9), — C(S)S(D-R9), — C(S)NH(D-R10), — C(S)N(D-R10) (D-R9), — CH=NO(D-R11), — C(D-R9)=NO(D-R11), — Si(D-R13)(D-R14) (D-R12), phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-8 to D-13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 to D-46 or E-4 to E-7, E-23 to E-27 or E-28;D-R4is halogen atom, cyano, Cs-Cecycloalkyl, Cs-Cehalocycloalkyl, — OH, — O(D-R5), — S(O)r(D-R5), — N(D-R10) (D-R9), — N(D-R10)C(O) (D-R9), — N(D-R10)C(O)O(D-R9), — N(D-R10)C(O)S(D-R9), — N(D-R10)C(S)O(D-R9), — N(D-R10)C(S)S(D-R9), — N(D-R10)S(O)2(D-R9), — Si(D-R13)(D-R14) (D-R12), phenyl, phenyl substituted with (Z)Pi, D-l to D-5, D-8 to D-38, D-41, D-43 or D-44;D-R5is Ci-Cealkyl, Ci-Cehaloalkyl, Ci-Cshaloalkoxy Ci-Cshaloalkyl, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, C2-Cealkenyl, C2-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-7, D-9, D-15 to D-23, D-30 to D-35, E-3 to E-9, E-23 to E-27 or E-28D-R6is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, — S(O)2R9, — CHO, — C(O) (D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(S)O(D-R9), or — C(S)S(D-R9);D-R7is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cealkenyl or Cs-Cealkynyl;D-R8is Ci-Cealkyl;D-R9is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-Cealkoxy Ci-C4alkyl, Ci-Cealkylthio Ci-C4alkyl, cyano Ci-Cealkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkylAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04substituted with (Z)Pi, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-6 to D-35 or D-38;D-R10is hydrogen atom or Ci-Cealkyl, or D-R10together with D-R9may form a 5-membered ring with the nitrogen atom bonding them by forming C4alkylene chain, in this case, the alkylene chain may contain oxygen atom or sulfur atom;D-R11is Ci-Cealkyl, Ci-Cehaloalkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, phenyl or phenyl substituted with (Z)Pi, or D-R11together with D-R9may form 5- or 6-membered ring with the atom bonding them by forming C2-C3alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with Ci-Cealkyl;D-R12is Ci-Cealkyl, phenyl or phenyl substituted with (Z)Pi;D-R13and D-R14independently of each other are Ci-Cealkyl;D-R15is Ci-Cealkyl, Ci-Cehaloalkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, phenyl or phenyl substituted with (Z)Pi;D-R16is halogen atom, cyano, Cs-Cecycloalkyl, Cs-Cehalocycloalkyl, — O(D-R25), — N(D-R26) (D-R25), — SH, — S(O)r(D-R27), — SO2NH(D-R29), — SO2N(D-R29) (D-R28), — CHO, — C(O) (D-R28), — C(C)O(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(O)N(D-R29)O(D-R28), — C(S)NH(D-R29), — C(S)N(D-R29) (D-R28), — C(D-R31)=NOH, — C(D-R31)=NO(D-R30), — C(=N-D-R31)O(D-R30), — C(=N-D-R31)S(D-R30), — C(=N-D-R31)N(D-R29) (D-R30), — C(=NO-D-R31)NH(D-R29), — C(=NO-D-R31)N(D-R29) (D-R30), — Si(D-R13)(D-R14) (D-R12) phenyl, phenyl substituted with (Z)Pi, D-l to D-46, E-l to E-28, E-32 to E-38, E-43 to E-45 or M-l to M-ll;D-R17is Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-Cealkoxy carbonyl Ci-C4alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pior Ci-Cealkoxy carbonyl;D-R18is Ci-Cealkyl, phenyl Ci-C4alkyl or phenyl Ci-C4alkyl substituted with (Z)Pi, or D-R18together with D-R17may form a 5-membered ring with the nitrogen atom bonding them by forming C4alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, and may be arbitrarily substituted with methyl or methoxy;D-R19is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R16, Cs-Cecycloalkyl, C3-Cehalocycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, — CHO, — C(O) (D-R28), — C(O)O(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(S)NH(D-R29), — C(S)N(D-R29) (D-R28), — S(O)2(D-R28), — S(O)2NH(D-R29), — S(O)2N(D-R29) (D-R28), phenyl, phenylAttomey Docket No. 10620-164W02NCSURef.: 2025-138-04substituted with (Z)Pi, D-l to D-13, D-15 to D-25, D-30 to D-37, D-39, D-40, D-42, D-45 to D-46, E-5, E-7, E-9, E-24, E-25, E-27 or E-28;D-R19ais Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl, phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-8 to D-10, D-15 to D-23, E-4 to E-7, E-23 to E-27 or E-28;D-R19bis hydrogen atom or Ci-Cealkyl, or D-R19atogether with D-R19bmay form 5- or 6-membered ring with the carbon atom bonding them by forming C4 or Csalkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom;D-R20is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, cyano Ci-Cealkyl, Ci-C4alkoxycarbonyl Ci-C4alkyl, C2-Cealkenyl, C3-Cealkynyl, — CHO, — C(O) (D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(S)O(D-R9), — C(S)S(D-R9) or Ci-Cealkylsulfonyl;D-R22is halogen atom, cyano, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-Cealkoxy, Ci-Cealkoxycarbonyl, — C(0)NH2 or — C(S)N2, when ql, q2, q3 or q4 is an integer of 2 or more, each D-R22may be identical with or different from each other, further in case where two D-R22s are present on the same carbon atom, the two D-R22s together may form oxo, thioxo, imino, Ci-Cealkylimino, Ci-Cealkoxyimino or Ci-Cealkylidene;R23is hydrogen atom, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R32, C3-Cecycloalkyl, Cs-Cealkenyl, Cs-Cealkynyl, — OH, benzyloxy, — CHO, — C(O) (D-R33), — C(O)O(D-R33), — C(O)S(D-R33), — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), — S(O)2(D-R33), phenyl, phenyl substituted with (Z)Pior D-5;D-R25is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, cyano Ci-Cealkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, C3-C6alkenyl, Cs-Cealkynyl, —CHO, — C(O) (D-R33), — C(O)O(D-R33), — C(O)S(D-R33), — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), — C(S) (D-R33), — C(S)O(D-R33), — C(S)S(D-R33), — C(S)NH(D-R34), — C(S)N(D-R34) (D-R33), — S(O)2(D-R33), — S(O)2N(D-R34) (D-R33), di(Ci-C6alkyl)phosphoryl, di(Ci-C6alkyl)thiophosphoryl, tri(Ci-C4alkyl)silyl, phenyl or phenyl substituted with (Z)Pi;D-R26is hydrogen atom, Ci-Cealkyl, Cs-Cealkenyl, Cs-Cealkynyl or Ci-Cealkoxy, or D-R26together with D-R25may form 4- to 5 -membered ring with the nitrogen atom bonding them by forming C3-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may substituted with Ci-Cealkyl, oxo or thioxo;D-R27is Ci-Cealkyl, Ci-Cehaloalkyl, hydroxy Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Ci-C4alkylcarbonyl Ci-C4alkyl, Ci-C4alkoxy carbonyl Ci-C4alkyl, di(Ci-Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04C4alkyl)aminocarbonyl Ci-C4alkyl, tri(Ci-C4alkyl)silyl Ci-C4alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Cealkenyl, Cs-Cealkynyl, Ci-Cealkylcarbonyl, Ci-Cealkylthio, phenylthio, phenylthio substituted with (Z)Pi, — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), — C(S)NH(D-R34), — C(S)N(D-R34) (D-R33), phenyl, phenyl substituted with (Z)Pi, D-21 or D-35;D-R28is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R32, Cs-Cecycloalkyl, C3-Cehalocycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, phenyl, phenyl substituted with (Z)Pi, D-l to D-46 or E-l to E-28, E-32 to E-38, or E-43 to E-45;D-R29is hydrogen atom, Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, cyano Ci-Cealkyl, Cs-Cealkenyl or Cs-Cealkynyl, or D-R29together with D-R28may form 3- to 5-membered ring with the nitrogen atom bonding them by forming C2-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom;D-R30is Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Cs-Cecycloalkyl Ci-C4alkyl, tri(Ci-C6alkyl)silyl Ci-C4alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Csalkenyl, Cs-Cshaloalkenyl, Cs-Csalkynyl or Cs-Cshaloalkynyl;D-R31is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl or Cs-Cecycloalkyl, or D-R31together with D-R30may form 5- or 6-membered ring with the atom bonding them by forming C2-C3alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with Ci-Cealkyl;D-R32is halogen atom, cyano, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, — O(D-R33), — OC(O) (D-R33), — OC(O)NH(D-R33), — OC(O)N(D-R34) (D-R33), — S(O)r(D-R33), — SC(O) (D-R33), — SC(O)NH(D-R33), — SC(O)N(D-R34) (D-R33), — N(D-R34)CHO, — N(D-R34)C(O) (D-R33), — N(D-R34)C(O)O(D-R33), — C(O)O(D-R33), — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), phenyl, phenyl substituted with (Z)Pi, D-l to D-46 or E-l to E-28, E-32 to E-38, or E-43 to E-45;D-R33is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4haloalkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Ci-C4haloalkylthio Ci-C4alkyl, Ci-C4alkylsulfonyl Ci-C4alkyl, Ci-C4haloalkylsulfonyl Ci-C4alkyl, cyano Ci-Cealkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Cecycloalkyl, Cs-Cehalocycloalkyl, C3-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-8 to D-13, D-15 to D-18, D-21, D-29 to D-37, E-5, E-7, E-9, E-24, E-25, E-27, E-28 or E-34;D-R34is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cealkenyl or Cs-Cealkynyl, or D-R34together with D-R33may form 3- to 5 -membered ring with the nitrogen atom bonding themAttomey Docket No. 10620-164W02NCSURef.: 2025-138-04by forming C2-Csalkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom.

19. The compound of any one of claims 17-18, whereinD-G is a benzene ringD-X is halogen atom, cyano, nitro, — SFs, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R4, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, C2-Cealkenyl, C2-Cehaloalkenyl, C2-Cealkynyl, C2-C6haloalkynyl, — O(D-R5), — OSO2(D-R5), — S(O)r(D-R5), — C(O)O(D-R9), — C(O)S(D-R9), — C(S)O(D-R9), — C(S)S(D-R9), — C(S)NH(D-R10), — C(S)N(D-R10) (D-R9), — CH=NO(D-R11), — C(D-Ry)=NO(D-R"). — Si(D-R13)(D-R14) (D-R12), E-10, E-12, E-18, E-32, E-35 or E-43, when m is 2 or 3, each D-X may be identical with or different from each other, further, when two D-Xs are adjacent, the adjacent two D-Xs may form 5 -membered or 6-membered ring together with carbon atoms to which the two D-Xs are bonded by forming — CF2OCF2—, — OCF2O—, — CF2OCF2O— or — OCF2CF2O—;D-Y is halogen atom, cyano, nitro, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R4, — O(D-R5), — OSO2(D-R5), — S(O)r(D-R5), — NH(D-R7), — N(D-R7) (D-R6), — N=C(D-R9)O(D-R8), — C(0)NH2 or — C(S)NH2, when n is 2 or 3, each D-Y may be identical with or different from each other;D-R1is Ci-Csalkyl, Ci-Csalkyl arbitrarily substituted with D-R16, Cs-Cscycloalkyl, C3-Cshalocycloalkyl, Cs-Csalkenyl, Cs-Cshaloalkenyl, Cs-Csalkynyl, Cs-Cshaloalkynyl, — N(D-R20) (D-R19), — C(O)N(D-R10) (D-R9), — C(S)N(D-R10) (D-R9), phenyl substituted with (Z)Pi, D-8 to D-18, D-21 to D-24, D-26 to D-40, D-42, D-45 to D-46, E-4, E-5, E-7, E-8, E-9, E-23 to E-25, E-27, E- 28 or E-34;D-R2is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, cyano Ci-Cealkyl, Cs-Cecycloalkyl, Cs-Cealkenyl, Cs-Cealkynyl, — OH, Ci-Cealkoxy, Ci-Cealkylcarbonyloxy, Ci-Cealkoxycarbonyloxy, Ci-Cealkylsulfonyloxy, Ci-Cehaloalkylthio, phenylthio, phenylthio substituted with (Z)Pi, Ci-Cealkylsulfonyl, — SN(D-R18) (D-R17), — NH(D-R20), — N=CH(D-R19b), — N=C(D-R19b) (D-R19a), — C(O) (D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(S)O(D-R9) or — C(S)S(D-R9), or D-R2together with D-R1may form 3- to 5-membered ring with the nitrogen atom bonding them by forming C2-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom;D-R3is Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Cs-Cehalocycloalkyl Ci-C4alkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4haloalkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Ci-Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04C4alkylsulfinyl Ci-C4alkyl, Ci-C4alkylsulfonyl Ci-C4alkyl, Ci-C4haloalkylthio Ci-C4alkyl, Ci-C4haloalkylsulfinyl Ci-C4alkyl, Ci-C4haloalkylsulfonyl Ci-C4alkyl, cyano Ci-Cealkyl, Ci-C4alkoxy Ci-C4haloalkyl, Ci-C4haloalkoxy Ci-C4haloalkyl, Ci-C4alkylthio Ci-C4haloalkyl, Ci-C4alkylsulfinyl Ci-C4haloalkyl, Ci-C4alkylsulfonyl Ci-C4haloalkyl, Ci-C4haloalkylthio Ci-C4haloalkyl, Ci-C4haloalkylsulfinyl Ci-C4haloalkyl, Ci-C4haloalkylsulfonyl Ci-C4haloalkyl, cyano Ci-Cehaloalkyl, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, E-4 to E-7, E-23 to E-27 or E-28;D-R4is halogen atom, cyano, — OH, Ci-Cealkoxy, Ci-Cehaloalkoxy, Ci-Cealkylthio, Ci-Cehaloalkylthio, Ci-Cealkylsulfinyl, Ci-Cehaloalkylsulfinyl, Ci-Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl or tri(Ci-C6alkyl)silyl;D-R5is Ci-Cealkyl, Ci-Cehaloalkyl, Ci-Cshaloalkoxy Ci-Cshaloalkyl, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, C2-Cealkenyl, C2-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, E-4 to E-9, E-23 to E-27 or E-28;D-R6is Ci-Cealkyl, Ci-Cehaloalkyl, — S(O)2(D-R9), — CHO, — C(O) (D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(S)O(D-R9) or — C(S)S(D-R9);D-R7is hydrogen atom, Ci-Cealkyl or Ci-Cehaloalkyl;D-R9is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-Cealkoxy Ci-C4alkyl, Ci-Cealkylthio Ci-C4alkyl, cyano Ci-Cealkyl, phenyl Ci-C4alkyl, Cs-Cscycloalkyl, C3-Cshalocycloalkyl, Cs-Cealkenyl or Cs-Cealkynyl;D-R10is hydrogen atom or Ci-Cealkyl, or D-R10together with D-R9may form a 5-membered ring with the nitrogen atom bonding them by forming C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom;D-R11is Ci-Cealkyl or Ci-Cehaloalkyl, or D-R11together with D-R9may form 5- or 6-membered ring with the atom bonding them by forming C2 or Csalkylene chain, in this case, the alkylene chain may be arbitrarily substituted with Ci-Cealkyl;R15is Ci-Cealkyl or Ci-Cehaloalkyl;D-R16is halogen atom, cyano, Cs-Cecycloalkyl, Cs-Cehalocycloalkyl, — O(D-R25), — N(D-R26) (D-R25), — S(O)r(D-R27), — SO2NH(D-R29), — SO2N(D-R29) (D-R28), —CHO, — C(O) (D-R28), — C(O)O(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(O)N(D-R29)O(D-R28), — C(S)NH(D-R29), — C(S)N(D-R29) (D-R28), — C(D-R31)=NOH, — C(D-R31)=NO(D-R30), — C(=N-D-R31)O(D-R30), — C(=N-D-R31)S(D-R30), — C(=N-D-R31)N(D-R29) (D-R30), — C(=NO-D-R31)NH(D-R29)’ — C(=NO-D-R31)N(D-R29) (D-R30), phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-8 to D-42, E-4 to E-12, E-14, E-16 to E-19, E-21 to E-23, E-26 to E-28, E-43 to E-45, M-2, M-3, M-5 or M-8 to M-10;Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04D-R17is Ci-Cealkyl, Ci-Cealkoxy carbonyl Ci-C4alkyl or Ci-Cealkoxy carbonyl;D-R18is Ci-Cealkyl or benzyl;D-R19is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-Cealkyl, phenyl Ci-Cealkyl, phenyl Ci-Cealkyl substituted with (Z)Pi, Cs-Cecycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, C3-Cealkynyl, — C(O) (D-R28), — C(O)O(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(S)NH(D-R29), — C(S)N(D-R29) (D-R28), Ci-Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with (Z)Pi, phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-18, D-21, D-25 or D-30 to D-35;D-R19ais Ci-Cealkyl;D-R19bis hydrogen atom or Ci-Cealkyl;D-R20is hydrogen atom, Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, cyano Ci-Cealkyl, Cs-Cealkenyl, Cs-Cealkynyl, — CHO, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci-Cealkoxy carbonyl, Ci-Cehaloalkoxy carbonyl or Ci-Cealkylsulfonyl;D-R22is Ci-C4alkyl or Ci-C4haloalkyl, or two D-R22s present on the same carbon atom may together form oxo, or thioxo;D-R23is hydrogen atom, Ci-Cealkyl, — CHO, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci-Cealkoxy carbonyl, Ci-Cealkylsulfonyl or Ci-Cehaloalkylsulfonyl, D-R25is hydrogen atom, Ci-Cealkyl, Ci-Cehaloalkyl, — C(O) (D-R33), — C(O)O(D-R33), — C(O)S(D-R33), — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), — C(S) (D-R33), — C(S)O(D-R33), — C(S)S(D-R33), — C(S)NH(D-R34), — C(S)N(D-R34) (D-R33), — S(O)2(D-R33), — S(O)2N(D-R34) (D-R33), di(Ci-C6alkyl)thiophosphoryl, phenyl or phenyl substituted with (Z)Pi;D-R26is hydrogen atom or Ci-Cealkyl, or D-R26together with D-R25may form 4- to 5-membered ring with the nitrogen atom bonding them by forming C3-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be substituted with Ci-Cealkyl, oxo or thioxo;D-R27is Ci-Cealkyl, Ci-Cehaloalkyl, tri(Ci-C4alkyl)silyl Ci-C4alkyl, Ci-Cealkylthio, — C(O)NH(D-R34), — C(O)N(D-R34) (D-R33), — C(S)NH(D-R34), — C(S)N(D-R34) (D-R33), phenyl or phenyl substituted with (Z)Pi;D-R28is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R32, Cs-Cecycloalkyl, C3-Cehalocycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, phenyl or phenyl substituted with (Z)Pi;Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04D-R29is hydrogen atom, Ci-Cealkyl, Cs-Cealkenyl or Cs-Cealkynyl, or D-R29together with R28may form 3- to 5-membered ring with the nitrogen atom bonding them by forming C2-C4 alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom;D-R30is Ci-Cealkyl, Cs-Cecycloalkyl Ci-C4alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Csalkenyl or Cs-Csalkynyl;D-R31is hydrogen atom or Ci-Cealkyl, or D-R31together with D-R30may form 5- or 6-membered ring with the atom bonding them by forming C2 or Csalkylene chain, in this case, the alkylene chain may be arbitrarily substituted with Ci-Cealkyl;D-R32is halogen atom, cyano, Cs-Cecycloalkyl, Cs-Cehalocycloalkyl, Ci-C4alkoxy, Ci-C4haloalkoxy, Ci-C4alkylthio, Ci-C4haloalkylthio, Ci-C4alkoxycarbonyl, — C(0)NH2, Ci-C4alkylaminocarbonyl, di(Ci-C4alkyl)aminocarbonyl, phenyl or phenyl substituted with (Z)Pi, D-R33is Ci-Cealkyl, Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, Ci-C4alkylsulfonyl Ci-C4alkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, C3-Cecycloalkyl, Cs-Cehalocycloalkyl, Cs-Cealkenyl, Cs-Cealkynyl, phenyl or phenyl substituted with (Z)Pi;D-R34is hydrogen atom or Ci-Cealkyl;m is an integer of 1 to 3;n is an integer of 0 to 2;ql is 0;q2 is an integer of 0 to 3;q3 is an integer of 0 to 2; andq4 is an integer of 0 to 2.

20. The compound of any one of claims 17-19, whereinD-A1is carbon;D-A2and D-A3are carbon atom;D-G is a benzene ring;D-X is halogen atom, cyano, nitro, — SFs, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R4, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, C2-Cealkenyl, C2-C6haloalkenyl, C2-Cealkynyl, C2-Cehaloalkynyl, — O(D-R5), — OSO2(D-R5), — S(O)r(D-R5) or tri(Ci-C6alkyl)silyl, when m is 2 or 3, each D-X may be identical with or different from each other,Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04further, when two D-Xs are adjacent, the adjacent two D-Xs may form 5 -membered or 6-membered ring together with carbon atoms to which the two D-Xs are bonded by forming — CF2OCF2—, — OCF2O—, — CF2OCF2O— or — OCF2CF2O—;D-Y is halogen atom, cyano, nitro, Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R4, — O(D-R5), — OSO2(D-R5), — S(O)r(D-R5), — NH(D-R7), — N(D-R7) (D-R6), — C(O)NH2or — C(S)NH2, when n is 2 or 3, each D-Y may be identical with or different from each other;D-R1is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R16, Cs-Cscycloalkyl, C3-Cehalocycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, Cs-Cehaloalkynyl, — N(D-R20) (D-R19), — C(O)N(D-R10) (D-R9), — C(S)N(D-R10) (D-R9), phenyl substituted with (Z)Pi, D-8, D-10, D-ll, D-13 to D-15, D-17, D-18, D-21 to D-23, D-26 to D-37, D-39, D-40, D-42, D-45, E-4, E-5, E-7 or E-9;D-R2is hydrogen atom, Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, cyano Ci-Cealkyl, Cs-Cecycloalkyl, Cs-Cealkenyl, Cs-Cealkynyl, — OH, Ci-Cealkylcarbonyloxy, Ci-Cealkylsulfonyloxy, — NH2, — C(O) (D-R9), — C(O)O(D-R9), — C(O)S(D-R9), — C(S)O(D-R9) or— C(S)S(D-R9);D-R3is Ci-Cehaloalkyl, Ci-C4alkoxy Ci-C4haloalkyl, Ci-C4haloalkoxy Ci-C4haloalkyl, Ci-C4alkylthio Ci-C4haloalkyl, Ci-C4haloalkylthio Ci-C4haloalkyl, cyano Ci-Cehaloalkyl or C3-Cshalocycloalkyl;D-R4is halogen atom, cyano, — OH, Ci-Cealkoxy, Ci-Cehaloalkoxy, Ci-Cealkylthio, Ci-Cehaloalkylthio, Ci-Cealkylsulfinyl, Ci-Cehaloalkylsulfinyl, Ci-Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl or tri(C i-Cealkyljsilyl;D-R5is Ci-Cealkyl, Ci-Cehaloalkyl, Ci-Cshaloalkoxy Ci-Cshaloalkyl, Cs-Cscycloalkyl, Cs-Cshalocycloalkyl, C2-Cealkenyl, C2-Cehaloalkenyl, Cs-Cealkynyl or Cs-Cehaloalkynyl;D-R6is Ci-Cealkyl, Ci-Cehaloalkyl, — CHO, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl, Cs-Cecycloalkylcarbonyl, Cs-Cehalocycloalkylcarbonyl, Ci-Cealkoxycarbonyl, Ci-Cehaloalkoxy carbonyl, Ci-Cealkylthiocarbonyl, Ci-Cealkoxythiocarbonyl, Ci-Cealkyldithiocarbonyl, Ci-Cealkylsulfonyl or Ci-Cehaloalkylsulfonyl;D-R7is hydrogen atom or Ci-Cealkyl;D-R9is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-Cealkoxy Ci-C4alkyl, Ci-Cealkylthio Ci-C4alkyl, cyano Ci-Cealkyl, Cs-Cscycloalkyl, Cs-Cealkenyl or C3-Cealkynyl;D-R16is halogen atom, cyano, Cs-Cecycloalkyl, Cs-Cehalocycloalkyl, — O(D-R25), — N(D-R26) (D-R25), — S(O)r(D-R27), — SO2NH(D-R29), — SO2N(D-R29) (D-R28), — C(O) (D-R28),Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04— C(O)O(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(O)N(D-R29)O(D-R28), — C(S)NH(D-R29), — C(S)N(D-R29) (D-R28), — C(D-R31)=NOH, — C(D-R31)=NO(D-R30), — C(=N-D-R31)O(D-R30), — C(=N-D-R31)S(D-R30), phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-8 to D-38, E-4 to E-12, E-18, E-19, E-32, E-35, E-43, M-2, M-3, M-5, M-8, M-9 or M-10;D-R19is Ci-Cehaloalkyl, Cs-Cecycloalkyl, — C(O) (D-R28), — C(O)O(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(S)NH(D-R29), — C(S)N(D-R29) (D-R28), phenyl, phenyl substituted with (Z)Pi, D-3, D-4, D-21;D-R20is hydrogen atom, Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, cyano Ci-Cealkyl, Cs-Cealkenyl, Cs-Cealkynyl, — CHO, Ci-Cealkylcarbonyl, Ci-Cealkoxy carbonyl or Ci-Cealkylsulfonyl;D-R25is Ci-Cealkyl, Ci-Cehaloalkyl, Ci-Cealkylcarbonyl, Ci-Cealkoxy carbonyl, Ci-Cealkylaminocarbonyl, di(Ci-C6alkyl)aminocarbonyl or Ci-Cealkylsulfonyl;D-R26is hydrogen atom or Ci-Cealkyl;D-R27is Ci-Cealkyl, Ci-Cehaloalkyl or tri(Ci-C4alkyl)silyl Ci-C4alkyl;D-R28is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Ci-C4alkoxy Ci-C4alkyl, Ci-C4alkylthio Ci-C4alkyl, cyano Ci-Cealkyl, phenyl Ci-C4alkyl, phenyl Ci-C4alkyl substituted with (Z)Pi, Cs-Cecycloalkyl, Cs-Cealkenyl, Cs-Cehaloalkenyl, Cs-Cealkynyl, phenyl or phenyl substituted with (Z)Pi;D-R29is hydrogen atom, Ci-Cealkyl, Cs-Cealkenyl or Cs-Cealkynyl;D-R30is Ci-Cealkyl or Cs-Cecycloalkyl Ci-C4alkyl;D-R31is hydrogen atom or Ci-Cealkyl, or D-R31together with D-R30may form 5- or 6-membered ring with the atom bonding them by forming C2 or Csalkylene chain.

21. The compound of any one of claims 17-20, whereinD-X is halogen atom, cyano, nitro, — SFs, Ci-Cealkyl, Ci-Cehaloalkyl, hydroxy Ci-Cehaloalkyl, Ci-Cealkoxy Ci-Cehaloalkyl, Ci-Cehaloalkoxy Ci-Cehaloalkyl, C3-Cshalocycloalkyl, — O(D-R5), — OSO2(D-R5) or — S(O)r(D-R5), when m is 2 or 3, each D-X may be identical with or different from each other;D-Y is halogen atom, cyano, nitro, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4alkoxy, Ci-C4haloalkoxy, Ci-Cealkylthio, Ci-Cehaloalkylthio, Ci-Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl, — NH(D-R7) or — N(D-R7) (D-R6);Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04D-R1is Ci-Cealkyl, Ci-Cealkyl arbitrarily substituted with D-R16, Cs-Cecycloalkyl, C3-Cealkenyl, Cs-Cshaloalkenyl, Cs-Cealkynyl, — N(D-R20)(D-R19), D-8, D-10, D-13 to D-15, D-18, D-21, D-34, D-35;D-R2is hydrogen atom, Ci-Cealkyl, Ci-C4alkoxy Ci-C4alkyl, cyano Ci-Cealkyl, C3-Cealkynyl, — C(O) (D-R9) or — C(O)O(D-R9);D-R3is Ci-Cehaloalkyl or Cs-Cshalocycloalkyl;D-R5is Ci-Cealkyl, Ci-Cehaloalkyl or Ci-Cshaloalkoxy Ci-Cshaloalkyl;D-R6is Ci-Cealkyl, — CHO, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci- Cealkoxy carbonyl, Ci-Cealkylthiocarbonyl, Ci-Cealkoxythiocarbonyl, Ci-Cealkyldithiocarbonyl, Ci-Cealkylsulfonyl or Ci-Cehaloalkylsulfonyl;D-R9is Ci-Cealkyl, Ci-Cealkoxy Ci-C4alkyl, Ci-Cealkylthio Ci-C4alkyl, Cs-Cscycloalkyl, Cs-Cealkenyl or Cs-Cealkynyl;D-R16is halogen atom, cyano, Cs-Cecycloalkyl, Cs-Cehalocycloalkyl, Ci-Cealkoxy, Ci-Cehaloalkoxy, Ci-Cealkylthio, Ci-Cehaloalkylthio, Ci-Cealkylsulfinyl, Ci-Cehaloalkylsulfinyl, Ci-Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl, Ci-Cealkylcarbonyl, — C(O)O(D-R28), — C(O)NH(D-R29), — C(O)N(D-R29) (D-R28), — C(S)NH2, — C(D-R31)=NOH, — C(D-R31)=NO(D-R30), phenyl, phenyl substituted with (Z)Pi, D-l to D-4, D-8 to D-38, E-4 to E-7, E-10, E- 11 or E-32;D-R19is Ci-Cehaloalkyl, — C(O) (D-R29), — C(O)O(D-R28), phenyl, phenyl substituted with (Z)Pi, D-3, D-4, D-21;D-R20is hydrogen atom or Ci-Cealkyl;D-R28is Ci-Cealkyl, Ci-Cehaloalkyl, Cs-Cecycloalkyl Ci-C4alkyl, Cs-Cecycloalkyl, C3-Cealkenyl or Cs-Cealkynyl;D-R29is hydrogen atom or Ci-Cealkyl;D-R30is Ci-Cealkyl;D-R31is hydrogen atom or Ci-Cealkyl; andn is an integer of 0 or 1.

22. A compound of Formula IXAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04(E-Q)Formula IXincluding geometric and stereoisomers, N-oxides, and salts thereof, whereinY is chosen from S, S=O, and S(=O)2;E-Ai, E-A2, E-A3, E-A4, E-As and E-Ae are each independently selected from the group consisting of C(E-R3') and N;n is an integer from 0 to 4;E-Bi, E-B2 and E-B3 are each independently selected from the group consisting of C(E-R2') andN;each E-R2' is independently of the other H or E-R2;each E-R3' is independently of the other H or E-R3;E-R₁ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₄-C₇-alkylcycloalkyl or C₄-C₇-cycloalkylalkyl, each unsubstituted or substituted with one or more substituents independently selected from E-R₄;each E-R2is independently halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, N-mono- or N, N-di-Ci-C6-alkylamino, C2-Ce alkoxy carbonyl, cyano ( — CN) or nitro ( — NO2);each E-Rais independently halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, C3-Ce-halocycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce alkyl-sulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, amino, N-mono- or N, N-di-Ci-Ce-alkylamino, Ci-Ce-alkoxy carbonyl, — CN or — NO2;E-R4is halogen, Ci-Ce-alkyl, Ci-Ce-alkoxy, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, — CN or — NO2;E-Q is a 5- or 6-membered heterocyclic ring, a Ce-Cio-carbocyclic ring system, a 8-, 9- or 10-membered fused hetero-bicyclic ring system, or -C(=O)-N(E-TI)(E-T2), each of the ring systems being unsubstituted or substituted with one or more substituents independently selectedAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04from halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkoxy, Ci-Ce-haloalkoxy, C2-Ce-alkenyl, C2-Ce-haloalkenyl, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, — CN, — NO2, amino, N-mono- or N, N-di-Ci-C6-alkylamino, CO2H, Ci-Ce-alkoxy carbonyl, sulfonamido, N-mono- or N, N,di-Ci-C6-alkylsulfonamido, CONH2, N-mono- or N, N,di-Ci-C6-alkylaminocarbonyl, N-mono- or N, N,di-Ci-Ce-haloalkylaminocarbonyl, N — Ci-C2-haloalkylaminocarbonyl-Ci-C2-alkylaminocarbonyl, Ci-Ce-alkylcarbonylamino, C2-Ce-alkanoyl, C2-C6-haloalkanoyl, CH2(E-Rs), a group C(O)N=CHN(CH3)2, a group C(O)N=CHNHOCH3, pyrrolidonylcarbonyl, nitro- or cyano-substituted phenyl, benzyl, phenethyl, pyridyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl, benzoyl or phenoxy; and E-Ti is H, Ci-Ce-alkyl, which is unsubstituted or substituted by Ci-C4-alkoxy, cyano, phenyl, ethenyl or ethynyl, C2-C7alkylcarbonyl, C2-C7haloalkylcarbonyl, or C2-C7-alkoxy carbonyl;E-T2 is Ci-Ce-alkyl, a group — C(O)-E-J, a group — C(S)-E-J or a group — S(O)t-E-J; t is 1 or 2;E-J is C₁-C₆-alkoxy; C₁-C₆-haloalkoxy; C₁-C₆-alkylthio; C₁-C₆-haloalkylthio; N(E-R₇)(E-R₈); CO₂(E-R₇); CO(E-R₇); Ci-Ce-alkyl which is unsubstituted or substituted by C3-C6-cycloalkyl, halogen, cyano, nitro, hydroxy, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, NHCO(E-R₇), C₁-C₆-alkoxy carbonyl, sulfonamido, N-mono- or N, N, di-C₁-C₄-alkylsulfonamido, CON(E-R₇)(E-R₈), C2-Ce-alkanoyl, unsubstituted or Ci-C2-alkyl-, C1-C2-haloalkyl-, Ci-C2-alkoxy-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxy carbonylsubstituted Ce-Cio-aryl, or unsubstituted or Ci-C2-alkyl-, Ci-C2-haloalkyl-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxy carbonyl-substituted 4- to 6-membered heterocyclyl; C2-C6-alkenyl; C2-Ce-alkynyl; Cs-Ce-cycloalkyl which is unsubstituted or substituted by halogen, Ci-C2-alkyl or Ci-C2-haloalkyl; Ce-Cio-aryl unsubstituted or substituted by Ci-C2-alkyl, C1-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxy carbonyl; or 4- to 6-membered heterocyclyl unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl, C1-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxycarbonyl;E-R₇ and E-R₈ are each independently of the other H, C₁-C₆-alkyl, C₁-C₆-haloalkyl or C₃-C₆-cycloalkyl, alkylcycloalkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl; andAttomey Docket No. 10620-164W02NCSURef.: 2025-138-04E-R₅ is CO₂H, C₁-C₆-alkoxycarbonyl, CONH₂, N-mono- or N, N,di-C₁-C₆-alkylaminocarbonyl, N-mono- or N, N,di-C₁-C₆-haloalkylaminocarbonyl, C₁-C₆-alkylcarbonylamino, pyridinylaminocarbonyl or tetrahydrofuranyl.

23. The compound of claim 22, whereinE-Ai, E-A2, E-A3, E-A4, E-As and E-Ae are each independently selected from the group consisting of C(E-R3') and N;n is an integer from 0 to 4;E-Bi, E-B2 and E-B3 are each independently selected from the group consisting of C(E-R2') andN;each E-R2' is independently of the other H or E-R2;each E-R3' is independently of the other H or E-R3;E-R₁ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₄-C₇-alkylcycloalkyl or C₄-C₇-cycloalkylalkyl, each unsubstituted or substituted with one or more substituents independently selected from E-R₄;each E-R2is independently halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, N-mono- or N, N-di-Ci-C6-alkylamino, C2-C6-alkoxy carbonyl, cyano ( — CN) or nitro ( — NO2);each E-Rais independently halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, C3-Ce-halocycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce alkyl-sulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, amino, N-mono- or N, N-di-Ci-Ce-alkylamino, C2-Ce-alkoxy carbonyl, — CN or — NO2;E-R4is halogen, Ci-Ce-alkyl, Ci-Ce-alkoxy, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, — CN or — NO2; andE-Q is a 5- or 6-membered heterocyclic ring, or a Ce-Cio-carbocyclic ring system or a 8-, 9- or 10-membered fused hetero-bicyclic ring system, each of them being unsubstituted or substituted with one or more substituents independently selected from halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, — CN, — NO2, amino, N-mono- or N, N-di-Ci-Ce-alkylamino, C2-C6-alkoxy carbonyl, sulfonamido, N-mono- or N, N,di-Ci-C4-alkylsulfonamido, N-mono- orN, N-di-Ci-Ce-alkylcarbonylamino, C2-Ce-alkanoyl and unsubstituted or halogen-, Ci-Ce-alkyl-, Ci-Ce-Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04haloalkyl-, Ci-Ce-alkoxy-, Ci-Ce-haloalkoxy-, nitro- or cyano-substituted phenyl, benzyl, benzoyl or phenoxy.

24. The compound of any one of claims 22-23, wherein E-Bi, E-B2 and E-B3 are each C(E- R2').

25. The compound of any one of claims 22-24, wherein E-Ai, E-A2, E-A3, E-A4, E-As and E- Ae are each CH.

26. The compound of any one of claims 22-25, wherein E-Ri is Ci-Cs-haloalkyl.

27. The compound of any one of claims 22-26, wherein the compound is defined by Formula IXAincluding geometric and stereoisomers, N-oxides, and salts thereof, whereinY is chosen from S, S=O, and S(=O)2;n is an integer from 0 to 4;E-R₁ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₄-C₇-alkylcycloalkyl or C₄-C₇-cycloalkylalkyl, each unsubstituted or substituted with one or more substituents independently selected from E-R₄;each E-R2is independently halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, N-mono- or N, N-di-Ci-C6-alkylamino, C2-Ce alkoxy carbonyl, cyano ( — CN) or nitro ( — NO2);each E-Rais independently halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, C3-Ce-halocycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Attomey Docket No. 10620-164W02NCSURef.: 2025-138-04Ce alkyl-sulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, amino, N-mono- or N, N-di-Ci-C6-alkylamino, Ci-Ce-alkoxy carbonyl, — CN or — NO2;E-Rus halogen, Ci-Ce-alkyl, Ci-Ce-alkoxy, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, — CN or — NO2;E-Q is a 5- or 6-membered heterocyclic ring, a Ce-Cio-carbocyclic ring system, a 8-, 9- or 10-membered fused hetero-bicyclic ring system, or -C(=O)-N(E-TI)(E-T2), each of the ring systems being unsubstituted or substituted with one or more substituents independently selected from halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Ci-Ce-alkoxy, Cs-Ce-cycloalkoxy, Ci-Ce-haloalkoxy, C2-Ce-alkenyl, C2-Ce-haloalkenyl, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, — CN, — NO2, amino, N-mono- or N, N-di-Ci-Ce-alkylamino, CO2H, Ci-Ce-alkoxy carbonyl, sulfonamido, N-mono- or N, N,di-Ci-Ce-alkylsulfonamido, CONH2, N-mono- or N, N,di-Ci-Ce-alkylaminocarbonyl, N-mono- or N, N,di-Ci-Ce-haloalkylaminocarbonyl, N — Ci-C2-haloalkylaminocarbonyl-Ci-C2-alkylaminocarbonyl, Ci-Ce-alkylcarbonylamino, C2-Ce-alkanoyl, C2-Ce-haloalkanoyl, CH2(E-Rs), a group C(O)N=CHN(CH3)2, a group C(0)N=CHNH0CH3, pyrrolidonylcarbonyl, nitro- or cyano-substituted phenyl, benzyl, phenethyl, pyridyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl, benzoyl or phenoxy; and E-Ti is H, Ci-Ce-alkyl, which is unsubstituted or substituted by Ci-C4-alkoxy, cyano, phenyl, ethenyl or ethynyl, C2-C7alkylcarbonyl, C2-C7haloalkylcarbonyl, or C2-C7-alkoxy carbonyl;E-T2 is Ci-Ce-alkyl, a group — C(O)-E-J, a group — C(S)-E-J or a group — S(O)t-E-J; t is 1 or 2;E-J is C₁-C₆-alkoxy; C₁-C₆-haloalkoxy; C₁-C₆-alkylthio; C₁-C₆-haloalkylthio; N(E-R₇)(E-R₈); CO₂(E-R₇); CO(E-R₇); Ci-Ce-alkyl which is unsubstituted or substituted by C3-C6-cycloalkyl, halogen, cyano, nitro, hydroxy, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, NHCO(E-R₇), C₁-C₆-alkoxy carbonyl, sulfonamido, N-mono- or N, N, di-C₁-C₄-alkylsulfonamido, CON(E-R₇)(E-R₈), C2-Ce-alkanoyl, unsubstituted or Ci-C2-alkyl-, C1-C2-haloalkyl-, Ci-C2-alkoxy-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxy carbonylsubstituted Ce-Cio-aryl, or unsubstituted or Ci-C2-alkyl-, Ci-C2-haloalkyl-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxy carbonyl-substituted 4- to 6-membered heterocyclyl; C2-C6-alkenyl; C2-Ce-alkynyl; Cs-Ce-cycloalkyl which is unsubstituted or substituted by halogen, Ci-C2-alkyl or Ci-C2-haloalkyl; Ce-Cio-aryl unsubstituted or substituted by Ci-C2-alkyl, C1-C2-Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxy carbonyl; or 4- to 6-membered heterocyclyl unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl, C1-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxycarbonyl;E-R₇ and E-R₈ are each independently of the other H, C₁-C₆-alkyl, C₁-C₆-haloalkyl or C₃-C₆-cycloalkyl, alkylcycloalkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl;E-Rsis CO2H, Ci-Ce-alkoxycarbonyl, CONH2, N-mono- or N, N,di-Ci-Ce-alkylaminocarbonyl, N-mono- or N, N,di-Ci-C6-haloalkylaminocarbonyl, Ci-Ce-alkylcarbonylamino, pyridinylaminocarbonyl or tetrahydrofuranyl;and m is an integer from 0 to 4.

28. The compound of any one of claims 22-27, wherein E-Q is a 5- or 6-membered heterocyclic ring having from 1 to 4 same or different heteroatoms selected from the group consisting of N, O and S, which is further unsubstituted or substituted by one or more substituents selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4- alkylsulfonyl, Ci-C4-haloalkylsulfonyl, — CN, — NO2, C1-C4-alkoxy carbonyl, sulfonamido, N-mono- or N, N-di-Ci-C4-alkylcarbonylamino, C2-C3-alkanoyl and unsubstituted or halogen- or Ci-C4-alkyl-substituted phenyl, benzyl, benzoyl and phenoxy.

29. The compound of any one of claims 22-28, wherein E-Q is a radical shown belowAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04E-Q-1 E-Q-2 E-Q-3 E-Q-4E-Q-10 E-Q-11 E-Q-12 E-Q-13 E-Q-14E-Q-25 E-W-ZO E-Q-2 / t-u-za(E-R)r(E-R)rN-0 N=NN,^S _ N: / ZT / NH \A(E-R)rSxA(E-R)ry<(E R)r' E-Q-40 ’ E-Q-41 E-Q-42 E-Q-43 E-Q-44E-Q-55 E-Q-56 E-Q-57 E-Q-58 E-Q-59 E-Q-60Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04N 0‘ N S O H HE- E-Q-63 E-Q-64 E-Q-65 E-Q-61 Q-62(E-R), H (E-R), (E-R)rH (E-R), N. / N O HE-Q-66 E-Q-67 E-Q-68 E-Q-69 E-Q-70(E-R)rN S OE-Q-74 E-Q-75 ^0E E-Q-73 E-Q-71 -Q-72 (E-R), ^(E-R)ro N s H H E-Q- E-Q- 6 HE-Q-78 79E-Q-77 E-Q-80 7Q(E-R)r H (E-R) ( JE-R), (E-R)rrE-R), N'S'Z,E-Q- E-Q-84 E-Q-85 E-Q-81 E-Q-82 83O O (E-R), H (E-R), H (E-R), N'N% N-N'Z, O N H E-Q-9E-Q-88 E-Q-89 0 E-Q-86 E-Q-87O (E-R), (E R) (E-R), O.NZ^° hL E-Q- E-Q-93 E-Q-94 95E-Q-91 E-Q-92Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04E-Q-100 E-Q-101 E-Q-102 E-Q-103 E-Q-104 E-Q-105 E-Q-106 E-Q-107 E-Q-108 E-Q-109 E-Q-110 E-Q-111 E-Q-112 E-Q-113 E-Q-114 E-Q-115 E-Q-116 E-Q-117 E-Q-118 E-Q-119E-Q-12 E-Q-123 E-Q-120 2 H E E-Q-127 E-Q-124 -Q-126 E-Q-128 E-Q-130 E-Q-131E-Q-132 E-Q-133Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04wherein r is an integer from 0 to 3 and E-R is independently selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, Ci-C2-haloalkylthio, — CN, — NO2, and Ci-C4-alkoxy carbonyl.

30. A compound according to claim 29, wherein E-Q is a radical shown belowE-Q-24a E-Q-26a E-Q-30a E-Q-32aE-Q-44 E-Q-47wherein E-R is independently selected from the group consisting of halogen, Ci-C2-alkyl, C1-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, Ci-C2-haloalkylthio, — CN, — NO2, and C1-C4-alkoxy carbonyl31. The compound of claim 29, wherein E-Q is the radical E-Q-34, E-Q-43 or E-Q-47, wherein r is in each case 0.

32. The compound of any one of claims 22-31, whereinn is an integer from 1 to 3, E-Ri is Ci-Cs-haloalkyl, each E-R2 and E-R3 is independently selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, Ci-C2-haloalkylthio, — CN and — NO2, m is an integer from 0 to 2, and E-Q is either(i) phenyl, which is unsubstituted or substituted by 1 to 3, same or different substituents selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, Ci-C2-haloalkylthio, — CN, — NO2, and unsubstituted or halogen-, Ci-C2-alkyl-, Ci-C2-haloalkyl-, Ci-C2-alkoxy-, Ci-C2-haloalkoxy-, — CN and — NCh-substituted phenyl or phenoxy, or is(ii) a 5- or 6-membered heterocyclic ring having from 1 to 3 same or different heteroatoms selected from the group consisting of N, O and S, which is further unsubstituted or substituted by halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, C1-C2-haloalkylthio, — CN, — NO2 or Ci-C4-alkoxy carbonyl, or isAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04(iii) a fused hetero-bicyclic ring system comprising a 5- or 6-membered heterocyclic ring having from 1 to 3 same or different heteroatoms selected from the group consisting of N, O and S, to which is attached an annulated ring, and which is further unsubstituted or substituted by halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, Ci-C2-haloalkylthio, — CN, — NChor Ci-C4-alkoxy carbonyl.

33. The compound of any one of claims 22-32, whereinn is an integer from 1 to 3,E-Riis CF3,each E-f is independently selected from the group consisting of halogen, C1-C2-haloalkyl, Ci-C2-haloalkoxy and — CN,m is 0, andE-Q is either(i) a 5- or 6-membered heteroaromatic ring selected fromE-Q-5 E-Q-6 E-Q-7 E-Q-14< E-R)r(E-R)rH(E-R)r (E-R)r (E-R)r _ / N _^ / n _^| _ / / ii -NN / =IN\^N N'NHV uNE-Q-30 E-Q-31 E-Q-32 E-Q-33 E-Q-34 E-Q-24 E-Q-26E-RL <E-R)r (E-R)r213E-Q-43 E-Q-47 E-Q-49 E-Q-50 E-Q-52 E-Q-54 wherein r is an integer from 0 to 3 and E-R is independently selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, Ci-C2-haloalkylthio, — CN, — NO2, and Ci-C4-alkoxy carbonyl, or(ii) a fused hetero-bicyclic ring system selected fromAttorney Docket No. 10620-164W02NCSURef.: 2025-138-0434. The compound of any one of claims 22-33, whereinn is an integer from 1 to 3,E-Ri is CF3,each E-f is independently selected from the group consisting of halogen, C1-C2-haloalkyl, Ci-C2-haloalkoxy and — CN,m is 0, andQ is chosen from E-Q-5, E-Q-14, E-Q-24, E-Q-25, E-Q-26, E-Q-30, E-Q-32, E-Q-34, E-Q-43, E-Q-44, E-Q-47, E-Q-49, E-Q-50, and E-Q-75 wherein r is an integer of 0 or 1, and E-R is independently selected from the group consisting of Ci-C2-alkyl, halo-Ci-C2-alkyl, halo-Ci-C2-alkylcarbonyl, cyano, Ci-C4-alkoxycarbonyl, Ci-C4-alkoxycarbonylmethyl, carboxy-Ci-C2-alkyl, aminocarbonyl, N-mono- or N, N-di-Ci-C2-alkylaminocarbonyl, halo-Ci-C2-alkylaminocarbonylmethyl, halo-Ci-C2-alkylaminocarbonylmethylaminocarbonyl, halovinyl, — C(O)N=CHN(CH3)2, — C(O)N=CHNHOCH3, unsubstituted or halogen- or Ci-C2-alkoxy-substituted phenyl, benzyl and phenylethyl, unsubstituted and halogen-substituted 2-, 3- and 4-pyridyl and pyridylmethyl, pyridylcarbonylaminomethyl, pyrrolidinecarbonyl, and 2-tetrahy drofurany Imethy 1.

35. The compound of any one of claims 22-34, wherein E-Ri is CF3.

36. The compound of any one of claims 22-35, wherein E-Q is a 5- or 6-membered heterocyclic ring having from 1 to 3 same or different heteroatoms.

37. The compound of any one of claims 22-36, wherein m is 0.Attorney Docket No. 10620-164W02NCSURef.: 2025-138-0438. The compound of any one of claims 22-37, wherein E-Q is phenyl, which is substituted by 1 or 2 same or different substituents.

39. The compound of any one of claims 22-38, wherein E-Q is E-Q-24, E-Q-26, E-Q-30, E-Q-32, E-Q-34, E-Q-44 or E-Q-47.

40. A compound of F ormula Xincluding all geometric and stereoisomers, N-oxides, S-oxides and salts thereof, whereinY is chosen from S, S=O, and S(=O)2;F-X is S(O)m, O or N(F-Rs') and F-Xl and F-X2 are each independently of the other C(F-R3') orN,n is an integer from 0 to 4;m is an integer from 0 to 2;F-Rs' is H, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkylcarbonyl or Ci-Ce-alkoxy carbonyl; F-Bi, F-B2 and F-B3 are each independently selected from the group consisting of C(F-R2') andN;each F-R2' is independently of the other H or F-R2;each F-R3' is independently of the other H or F-R3;F-Ri is Ci-Cealkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Cs-Ce-cycloalkyl, C4-C7-alkylcycloalkyl or C4-C?cycloalkylalkyl, each unsubstituted or substituted with one or more substituents independently selected from F-R4;F-R4is halogen, Ci-Ce-alkyl, Ci-Ce-alkoxy, Ci-Ce-alkylthio, Ci-Cealkylsulfinyl, Ci-Ce-alkyl-sulfonyl, cyano or nitro;Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04each F-f is independently halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Cealkylsulfonyl, Ci-Ce-haloalkylsulfonyl, N-mono- or N, N-di-Ci-C6-alkylamino, Ci-Ce-alkoxy carbonyl, cyano ( — CN) or nitro ( — NO2);each F-R3 is independently H, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Cehaloalkylthio, Ci-Cealkyl-sulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Cealkylsulfonyl, Ci-Ce-haloalkylsulfonyl, amino, N-mono- or N, N-di-Ci-Ce-alkylamino, Ci-Ce-alkoxy carbonyl, cyano, nitro or unsubstituted or halogen-, Ci-Ce-alkyl-, Ci-Ce-haloalkyl-, Ci-Ce-alkoxy-, Ci-Ce-haloalkoxy-, amino-, cyano- or nitro-substituted phenyl, pyridyl or pyrimidyl;F-Rs is H, =0 (a carbonyl group), Ci-Ce-alkyl, Ci-Ce-haloalkyl, halogen or cyano; or F-R5 and F-X2 together with the intermediate C-atoms form a 5- or 6-membered carbocyclic ring;F-Re is H; Ci-Ce-alkyl, which is unsubstituted or substituted by Ci-C4-alkoxy, cyano, phenyl, ethenyl or ethynyl; C2-C?alkylcarbonyl; C2-C7haloalkylcarbonyl; C2-C?-alkoxycarbonyl;F-Z is Ci-Ce-alkyl, a group — C(O)-F-Q, a group — C(S)-F-Q or a group — S(O)t-F-Q; t is 1 or 2;F-Q is Ci-Ce-alkoxy; Ci-Ce-haloalkoxy; Ci-Ce-alkylthio; Ci-Ce-haloalkylthio; N(F-R?)(F-Rs); CO2(F-R?); CO(F-R?); Ci-Ce-alkyl which is unsubstituted or substituted by C3-C6-cycloalkyl, halogen, cyano, nitro, hydroxy, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, NHCO(F-R?), Ci-Ce-alkoxycarbonyl, sulfonamido, N-mono- orN, N, di-Ci-C4-alkylsulfonamido, CON(F-R?)( F-Rs), C2-Ce-alkanoyl, unsubstituted or Ci-C2-alkyl-, C1-C2-haloalkyl-, Ci-C2-alkoxy-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxy carbonylsubstituted Ce-Cio-aryl, or unsubstituted or Ci-C2-alkyl-, Ci-C2-haloalkyl-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxy carbonyl-substituted 4- to 6-membered heterocyclyl; C2-C6-alkenyl; C2-Ce-alkynyl; Cs-Ce-cycloalkyl which is unsubstituted or substituted by halogen, Ci-C2-alkyl or Ci-C2-haloalkyl; Ce-Cio-aryl unsubstituted or substituted by Ci-C2-alkyl, C1-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxy carbonyl; or 4- to 6-membered heterocyclyl unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl, C1-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxycarbonyl; andF-R7 and F-Rs are each independently of the other H, Ci-Ce-alkyl, Ci-Ce-haloalkyl or C3-Ce-cycloalkyl, alkylcycloalkyl, C2-Ce-alkenyl or C2-C6-alkynyl.Attorney Docket No. 10620-164W02NCSURef.: 2025-138-0441. The compound of claim 40, wherein F-Q is Ci-Ce-alkoxy; Ci-Ce-haloalkoxy; Ci-Ce-alkylthio; Ci-Ce-haloalkylthio; N(F-R?)(F-Rs); CCh F-R?); CO(F-R?); Ci-Ce-alkyl which is unsubstituted or substituted by Cs-Ce-cycloalkyl. halogen, cyano, nitro, hydroxy, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, Ci-Ce-alkylcarbonylamino, Ci-Ce-haloalkylcarbonylamino, Ci-Ce-alkoxy carbonyl, sulfonamido, N-mono- or N, N, di-Ci-C4-alkylsulfonamido, N-mono- or N, N-di-Ci-C6-alkylaminocarbonyl, N-mono- or N, N-di-Ci-Ce-haloalkylaminocarbonyl, C2-Ce-alkanoyl, unsubstituted or Ci-C2-alkyl-, Ci-C2-haloalkyl-, C1-C2-alkoxy-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxycarbonyl-substituted Ce-Cio-aryl, or unsubstituted or Ci-C2-alkyl-, Ci-C2-haloalkyl-, Ci-C2-alkoxy-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxy carbonyl-substituted 4- to 6-membered heterocyclyl; C2-Ce-alkenyl; C2-Ce-alkynyl; Cs-Ce-cycloalkyl which is unsubstituted or substituted by halogen, Ci-C2-alkyl or Ci-C2-haloalkyl; Ce-Cio-aryl unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl, C1-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4alkoxy carbonyl; or 4- to 6-membered heterocyclyl unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, C1-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxy carbonyl; andF-R7 and F-Rs are each independently of the other H, Ci-Ce-alkyl, Ci-Ce-haloalkyl or C3-Ce-cycloalkyl.

42. The compound of any one of claims 40-41, wherein F-Bi, F-B2 and F-B3 are each C(F-R2').

43. The compound of any one of claims 40-42, wherein F-X is S(O)m, one of F-Xi and F-X2is C(F-Rs') and the other one is N or independently C(F-Rs'), wherein F-R3' is each independently H or Ci-C2-alkyl, and m is an integer from 0 to 2.

44. The compound of any one of claims 40-43, wherein F-X is O, one of F-Xi and F-X2is C(F-R3') and the other one is N or independently C(F-R3'), wherein F-R3' is each independently H or Ci-C2-alkyl.

45. The compound of any one of claims 40-44, wherein F-Ri is Ci-Cs-haloalkyl, in particular CF3.Attomey Docket No. 10620-164W02NCSURef.: 2025-138-0446. The compound of any one of claims 40-45, wherein the compound is defined by Formula XA(F-R2)nFormula XBincluding all geometric and stereoisomers, N-oxides, S-oxides and salts thereof, whereinY is chosen from S, S=O, and S(=O)2;F-X is S(O)m, O or N(F-Rs') and F-Xl and F-X2 are each independently of the other C(F-R3') orN,n is an integer from 0 to 4;m is an integer from 0 to 2;each F-R3' is independently of the other H or F-R3;each F-R3 is independently H, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Cehaloalkylthio, Ci-Cealkyl-sulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Cealkylsulfonyl, Ci-Ce-haloalkylsulfonyl, amino, N-mono- or N, N-di-Ci-C6-alkylamino, Ci-Ce-alkoxy carbonyl, cyano, nitro or unsubstituted or halogen-, Ci-Ce-alkyl-, Ci-Ce-haloalkyl-, Ci-Ce-alkoxy-, Ci-Ce-haloalkoxy-, amino-, cyano- or nitro-substituted phenyl, pyridyl or pyrimidyl;F-Z is Ci-Ce-alkyl, a group — C(O)-F-Q, a group — C(S)-F-Q or a group — S(O)t-F-Q; t is 1 or 2;F-Q is Ci-Ce-alkoxy; Ci-Ce-haloalkoxy; Ci-Ce-alkylthio; Ci-Ce-haloalkylthio; N(F-R?)(F-Rs); CO2(F-R?); CO(F-R?); Ci-Ce-alkyl which is unsubstituted or substituted by C3-C6-cycloalkyl, halogen, cyano, nitro, hydroxy, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, NHCO(F-R?), Ci-Ce-alkoxycarbonyl, sulfonamido, N-mono- orN, N, di-Ci-C4-alkylsulfonamido, CON(F-R?)( F-Rs), C2-Ce-alkanoyl, unsubstituted or Ci-C2-alkyl-, C1-C2-haloalkyl-, Ci-C2-alkoxy-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxycarbonyl-Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04substituted Ce-Cio-aryl, or unsubstituted or Ci-C2-alkyl-, Ci-C2-haloalkyl-, Ci-C2-haloalkoxy-, halogen-, cyano- or Ci-C4-alkoxy carbonyl-substituted 4- to 6-membered heterocyclyl; C2-C6-alkenyl; C2-Ce-alkynyl; Cs-Ce-cycloalkyl which is unsubstituted or substituted by halogen, Ci-C2-alkyl or Ci-C2-haloalkyl; Ce-Cio-aryl unsubstituted or substituted by Ci-C2-alkyl, C1-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxy carbonyl; or 4- to 6-membered heterocyclyl unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl, C1-C2-alkoxy, Ci-C2-haloalkoxy, halogen, cyano or Ci-C4-alkoxycarbonyl; andF-R7 and F-Rs are each independently of the other H, Ci-Ce-alkyl, Ci-Ce-haloalkyl or C3-Ce-cycloalkyl, alkylcycloalkyl, C2-Ce-alkenyl or C2-C6-alkynyl.

47. The compound of claim 46, wherein F-Z is a group — C(O)-F-Q.

48. The compound of claim 47, wherein F-Q is straight-chain or branched Ci-C4-alkyl, which is each unsubstituted or substituted by Cs-Ce-cycloalkyl, halogen, cyano, hydroxy, Ci-C4alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4alkylsulfonyl, Ci-C2-alkylcarbonylamino or Ci-C2-haloalkylcarbonylamino; unsubstituted or methylsubstituted Cs-Ce-cycloalkyl; phenyl, which is unsubstituted or substituted by halogen, C1-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, cyano or Ci-C4alkoxycarbonyl; thienyl, furyl, oxazolyl, thiazolyl, pyridyl or pyrimidinyl, which are each unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl or Ci-C4-alkoxy carbonyl; or pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, piperidinyl, piperazinyl, morpholinyl, tetrahydropyranyl or thianyl which are each unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl or Ci-C4-alkoxy carbonyl.

49. The compound of claim 47, wherein F-Q is straight-chain or branched Ci-C4-alkyl, Ci-Cs-haloalkyl, cyclopropylmethyl, cyano-Ci-C2-alkyl, Ci-C2-alkoxy-Ci-C2-alkyl, Ci-C2-alkylthio-Ci-C2-alkyl, Ci-C2-alkylsulfinyl-Ci-C2-alkyl or Ci-C2-alkylsulfonyl-Ci-C2-alkyl.

50. The compound of claim 46, wherein n is an integer from 1 to 3; each F-R.2is independently selected from the group consisting of halogen, Ci-Ce-haloalkyl, Ci-Ce-haloalkoxy and cyano; X is S(O)m, O or N(F-Rs'); m is an integer from 0 to 2; F-Rs' is H or Ci-C2-alkyl; one of F-Xi and F-X2is C(F-Rs') and the other one is N or independently C(F-R3'); F-R3' is H or Ci-C2-alkyl; F-Z is a group — S(O)2 — Ci-C2-alkyl or a group — C(O)-Q; and F-Q is straight-chain or branched Ci-C4-alkyl, which is each unsubstituted or substituted by Cs-Ce-cycloalkyl,Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04halogen, cyano, Ci-C4-alkoxy, Ci-C2-haloalkoxy, Ci-C4alkylthio, Ci-C2-haloalkylthio, Ci-C4alkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C2-alkylcarbonylamino or C1-C2-haloalkylcarbonylamino; unsubstituted or methyl-substituted Cs-Ce-cycloalkyl; phenyl, which is unsubstituted or substituted by halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, C1-C2-haloalkoxy, cyano or Ci-C4-alkoxycarbonyl; thienyl, furyl, oxazolyl, thiazolyl, pyridyl or pyrimidinyl, which are each unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl or Ci-C4-alkoxycarbonyl; or pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, piperidinyl, piperazinyl, morpholinyl, tetrahydropyranyl or thianyl which is each unsubstituted or substituted by Ci-C2-alkyl, Ci-C2-haloalkyl or Ci-C4-alkoxy carbonyl.

51. The compound of any one of claims 40-45, wherein the compound is defined by Formula XBincluding all geometric and stereoisomers, N-oxides, and salts thereof, wherein Y is chosen from S, S=O, and S(=O)2; the radicals F-R2 are each independently of the other H, halogen or trifluoromethyl; F-R3' is hydrogen or methyl; F-Z is a radical — C(O)-F-Q; and F-Q is straightchain or branched Ci-C4-alkyl, Ci-Cs-haloalkyl, cyclopropylmethyl, cyano-Ci-C2-alkyl, C1-C2-alkoxy-Ci-C2-alkyl, Ci-C2-alkylthio-Ci-C2-alkyl, Ci-C2-alkylsulfinyl-Ci-C2-alkyl or C1-C2-alkylsulfonyl-Ci-C2-alkyl.

52. The compound of any one of claims 40-45, wherein the compound is defined by Formula XCAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04Formula XFincluding all geometric and stereoisomers, N-oxides, and salts thereof, wherein Y is chosen from S, S=O, and S(=O)2; the radicals F-R2 are each independently of the other H, halogen or trifluoromethyl; F-R3' is hydrogen or methyl; F-Z is a radical — C(O)-F-Q; and F-Q is straightchain or branched Ci-C4-alkyl, Ci-Cs-haloalkyl, cyclopropylmethyl, cyano-Ci-C2-alkyl, C1-C2-alkoxy-Ci-C2-alkyl, Ci-C2-alkylthio-Ci-C2-alkyl, Ci-C2-alkylsulfinyl-Ci-C2-alkyl or C1-C2-alkylsulfonyl-Ci-C2-alkyl.

53. A compound defined by Formula XIFormula XIwhereinY is chosen from S, S=O, and S(=O)2G-Rla, G-Rlb, and G-Rlcare each independently hydrogen, halo, hydroxyl, cyano, nitro, Ci-Cealkyl, Ci-Cehaloalkyl, Ci-Cealkoxy, Co-CsalkylCs-Ce cycloalkyl, Ci-Cehaloalkoxy, — C(O)NH2, — SFS, or— S(O)p(G-R);G-R2is fluoro, chloro, or Ci-Cealkyl;G-R3is cyano, Ci-Cealkyl, Ci-Cehaloalkyl, — C(O)NRaRb, C2-Cealkenyl, C2-Cealkynyl, C2-Cehaloalkenyl, or C2-Cehaloalkynyl;Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04G-R4is hydrogen, Ci-Cealkyl, C2-Cealkenyl, Co-CealkylCs-Cecycloalkyl, Co-Cealkylphenyl, Co-Cealkylheteroaryl, or Co-Cealkylheterocycle;R5is hydrogen, Ci-Cealkyl, hydroxyl, cyano, nitro, — S(O)PRC, or Ci-Cealkoxy;G-R is Ci-Cealkyl or Cs-Cecycloalkyl optionally substituted with at least one halo substituent;Rais hydrogen, Ci-Cealkyl, or Co-CsalkylCs-Cecycloalkyl; wherein the alkyl and alkylcycloalkyl is optionally substituted by cyano or at least one halo substituent;Rbis hydrogen, Ci-Cealkyl, Cs-Cecycloalkyl, Co-Csalkylphenyl, Co-Csalkylheteroaryl, or Co-Csalkylheterocycle, each optionally substituted, where chemically possible, with at least one substituent selected from hydroxyl, cyano, halo, or — S(O)P(G-R);Rcis Ci-Cealkyl, Ci-Cehaloalkyl, Ci-CehaloalkylCs-Cecycloalkyl, Co-CsalkylCs-Cecycloalkyl, Co-Csalkylphenyl, Co-Csalkylheteroaryl, or Co-Csalkylheterocycle each optionally substituted with at least one substituent selected from cyano, halo, hydroxyl, oxo, Ci-Cealkoxy, Ci-Cehaloalkoxy, Ci-Cehaloalkyl, — S(O)P(G-R), — SH, — S(O)PNRaRb, — NRaRb, — NRaC(O)Rb, — SC(O)(G-R), — SCN, or — C(O)NRaRb;when G-R4is Ci-Cealkyl or Co-CealkylCs-Cecycloalkyl, then each moiety can be optionally substituted by at least one substituent selected from cyano, halo, hydroxyl, oxo, Ci-Cealkoxy, Ci-Cehaloalkoxy, Ci-Cehaloalkyl, Ci-Cealkyl, hydroxylCi-Cealkyl-, — S(O)PRC, — SH, — S(O)PNRaRb, — NRaRb, — NRaC(O)Rb, — SC(O)(G-R), —SCN, or — C(O)NRaRb;when G-R4is Co-Cealkylphenyl, Co-Cealkylheteroaryl, or Co-Cealkylheterocycle, then each moiety can be further optionally substituted with at least one substituent selected from cyano, halo, oxo, =S, =N(G-R5), hydroxylCi-Cealkyl-, hydroxyl, Ci-Cealkoxy, Ci-Cealkyl, Ci-Cehaloalkyl, — SH, — S(O)P(G-R), and Ci-Cehaloalkoxy;n is the integer 0, 1, or 2, and when n is 2, each G-R2may be identical or different from each other; andp is the integer 0, 1, or 2;stereoisomers thereof, or a salt thereof.

54. The compound of claim 53, wherein the compound is chosen from the followingAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04wherein Y is chosen from S, S=O, and S(=O)255. The compound of claim 54, wherein the compound comprises the S-isomer of the compound.Formula XIIand / or a salt thereof whereinY is chosen from S, S=O, and S(=O)2;H-R3represents (Ci-C4)-alkyl, (C3-Cs)-cycloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or (Ci-C4)-alkoxy, each of which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, (Ci-C4)-alkoxy and hydroxy;H-R4represents hydrogen, or represents (Ci-Ci2)-alkyl, (C3-C7)-cycloalkyl, (C3-C7)-cycloalkyl-(Ci-C8)-alkyl, (C2-Ce)-alkenyl, (Cs-C6)-cycloalkenyl or (C2-Cs)-alkynyl, each of which is substituted by m radicals from the group consisting of halogen, cyano, (Ci-Ce)-alkoxy, hydroxy and aryl;H-Y represents oxygen or sulfur;H-W represents oxygen or sulfur;Attorney Docket No. 10620-164W02NCSURef.: 2025-138-04H-Z represents a fully saturated or partially saturated furan ring which is substituted by k radicals from R5,where the arrow denotes a bond to the group C=(H-W) of Formula XII and R5represents fluorine, chlorine, cyano or CCh(H-R7), or represents (Ci-C2)-alkyl or (Ci-C2)-alkoxy, each of which is substituted by m radicals from the group consisting of fluorine and chlorine;H-X2, H-X4and H-X6independently of one another each represent hydrogen, fluorine, chlorine, bromine or cyano, or represent (Ci-C2)-alkyl, in each case substituted by m radicals from the group consisting of fluorine, chlorine, bromine and (Ci-C2)-alkoxy;H-X3and H-X5independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, nitro, S(O)n(H-R6) or CO2(H-R7), or represent (Ci-C3)-alkyl, (Ci-C3)-alkoxy, (C3-C4)-cycloalkyl, (C2-C3)-alkenyl or (C2-C3)-alkynyl, each of which is substituted by m radicals from the group consisting of fluorine, chlorine and bromine;H-R6represents (Ci-C2)-alkyl or (C3-C4)-cycloalkyl, each of which is substituted by m radicals from the group consisting of fluorine and chlorine;H-R7represents hydrogen, or represents (Ci-C3)-alkyl or (C3-Cs)-cycloalkyl, each of which is substituted by m radicals from the group consisting of fluorine, chlorine and (C1-C2)-alkoxy;k represents 0, 1 or 2;m represents 0, 1, 2, 3, 4 or 5; andn represents 0, 1 or 2.

57. The compound of claim 56, where H-R3represents (Ci-C3)-alkyl, (C3-C4)-cycloalkyl, (C2-C3)-alkenyl, (C2-Cs)-alkynyl or (Ci-C3)-alkoxy, each of which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, (Ci-C2)-alkoxy and hydroxy.

58. The compound of any one of claims 56-57, where H-R4represents hydrogen, or represents (Ci-Ce)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-C6)-alkyl, (C2-Ce)-alkenyl, (Cs-C6)-cycloalkenyl or (C2-Ce)-alkynyl, each of which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, (Ci-C4)-alkoxy, hydroxy and aryl.Attorney Docket No. 10620-164W02NCSURef.: 2025-138-0459. The compound of any one of claims 56-58, wherein each of H-Y and H-W represents oxygen.

60. The compound of any one of claims 56-59, where H-Z represents a group chosen from H-Z-1 to H-Z-33:‘O' H-Z-1 H-Z-2 H-Z-3 H-Z-4 H-Z-5 H-Z-6•CH3X ft 0‘ ■CH3V O'H-Z-9 H-Z-10‘O' H-Z-17 H-Z-18 H-Z-19 H-Z-20 H-Z-21 H-Z-22 H-Z-23 H-Z-24 H-Z-25H-Z-26 H-Z-27 H-Z-28 H-Z-29 H-Z-30 H-Z-31 H-Z-32 H-Z-33 where the bond line in each case denotes a bond to the group C=(H-W) of Formula XII.

61. The compound of any one of claims 56-60, where R5represents fluorine, chlorine, cyano, CO2H, CO2CH3 or CO2CH2CH3, or represents (Ci-C2)-alkyl or (Ci-C2)-alkoxy, each of which is substituted by m radicals from the group consisting of fluorine and chlorine.

62. The compound of any one of claims 56-61, where H-X2, H-X4and H-X6independently of one another each represent hydrogen, fluorine, chlorine, bromine or cyano, or represent methyl or methoxy, each of which is substituted by m radicals from the group consisting of fluorine and chlorine.Attorney Docket No. 10620-164W02NCSURef.: 2025-138-0463. The compound of any one of claims 56-62, where H-X3and H-X5independently of one another each represent hydrogen, fluorine, chlorine, bromine, hydroxy or cyano, or represent (Ci-C3)-alkyl, (Ci-C3)-alkoxy, (C3-C4)-cycloalkyl, (C2-C3)-alkenyl or (C2-C3)-alkynyl, each of which is substituted by m radicals from the group consisting of fluorine, chlorine and bromine.

64. The compound of any one of claims 56-63, where H-R7represents hydrogen,Or represents (Ci-C3)-alkyl each substituted by m radicals from the group consisting of fluorine and chlorine.

65. The compound of any one of claims 56-64, where m is 0, 1, 2 or 3.

66. The compound of any one of claims 56-65, whereinY is chosen from S, S=O, and S(=O)2;H-R3represents (Ci-C3)-alkyl, (C3-C4)-cycloalkyl, (C2-C3)-alkenyl, (C2-C3)-alkynyl or (Ci-C3)-alkoxy, each of which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, (Ci-C2)-alkoxy and hydroxy;H-R4represents hydrogen, or represents (Ci-C6)-alkyl, (C3-Ce)-cycloalkyl, (Cs-Ce)-cycloalkyl-(Ci-C6)-alkyl, (C2-Ce)-alkenyl, (Cs-C6)-cycloalkenyl or (C2-Ce)-alkynyl, each of which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, (Ci-C4)-alkoxy, hydroxy and aryl;H-Y represents oxygen;H-W represents oxygen;H-Z represents a group Z-l to Z-4:“O'H-Z-1 H-Z-2 H-Z-3 H-Z-4where the bond line in each case denotes a bond to the group C=W of the formula (I):H-X2, H-X4and H-X6independently of one another represent hydrogen or fluorine; H-X3and H-X5independently of one another represent hydrogen, fluorine, chlorine, bromine, hydroxy or cyano, or represent (Ci-C3)-alkyl, (Ci-C3)-alkoxy, (C3-C4)-cycloalkyl, (C2-C3)-alkenyl or (Cb-Oj-alkyny 1, each of which is substituted by m radicals from the group consisting of fluorine, chlorine and bromine; andAttorney Docket No. 10620-164W02NCSURef.: 2025-138-04m represents 0, 1, 2 or 3.

Images