Pyrazole amide insecticides

Abstract

A compound of formula 1 is disclosed: [Formula 1] TIFF2025532081000045.tif26170A,R 1 , R 2 , R 3 , R 4 , R 5 , Q, and X are as defined herein. Also disclosed are compositions containing a compound of Formula 1 and methods for controlling and combating invertebrate pests comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound or composition of the invention.

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of U.S. Provisional Patent Application No. 63 / 409,393, filed September 23, 2022.

[0002] The present invention relates to novel pyrazole compounds and compositions suitable for agricultural and non-agricultural use, and methods of their use to control and combat invertebrate pests, such as arthropods, in both agricultural and non-agricultural environments. [Background technology]

[0003] Controlling invertebrate pests is crucial to achieving high yield efficiency. Damage caused by invertebrate pests to growing and stored crops can significantly reduce productivity, thereby resulting in increased costs to consumers. Controlling invertebrate pests is also important in forestry, greenhouse crops, ornamentals, seedling crops, stored food and fiber products, household, turf, wood products, and public health. While many products are commercially available for these purposes, there remains a need for new compounds that are more effective, less costly, less toxic, environmentally safer, or have a different mechanism of action. Summary of the Invention [Means for solving the problem]

[0004] The present disclosure relates to compounds of Formula 1 (all geometric and stereoisomers), N-oxides, and salts thereof, compositions containing them, and their use for controlling and combating invertebrate pests: [ka] During the ceremony, X is O or S; Each A is independently CH, N, or CR 1 and; Each R 1are independently H, amino, cyano, halogen, nitro, C(S)NH; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 1 is independently phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, and each phenyl or heteroaromatic ring is selected from one or more R 6 optionally substituted with R 1 are independently C3-C9-trialkylsilyl, C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O) p R 9 , SF5, SO2NR 7 R 8 , OS(O)2R 9 , or S(=NR 11 )O p R 9 or R 1is optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, when a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , or SO2NR 7 R 8 a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 2 is one or more R 6 and substituted by phenyl, or a 4-6 membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and 1-3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 2 nitrogen atoms, or a 5 membered heteroaromatic ring containing ring members selected from carbon atoms and 1-3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6 membered heteroaromatic ring containing ring members selected from carbon atoms and 1-2 nitrogen atoms, wherein each phenyl or heterocyclic ring is optionally substituted with one or more R 6 optionally substituted with R 2 is C(O)R 7 , C(O)OR 7 , N.R. 7 R 8 , OR 7 , S(O)pR 9 or SO2NR 7 R8 and; R 3 is C1-C3 alkyl or C1-C3 haloalkyl; R 4 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 4 is C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , S(O)pR 9 , SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 and; R 5 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6-alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 5 is C(O)R 7 , C.R. 7 (=NO)R 8 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7, N.R. 8 C(O)OR 7 , N.R. 11 SO2NR 7 R 8 , OR 7 , S(O)pR 9 , or SO2NR 7 R 8 and; R 6 are independently halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 ,OC(O)OR 7 , S(O)pR 9 , SO2NR 7 R 8 , or S(=NR)O p R 7 and; R 7 are independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl or cycloalkylalkyl is selected from the group consisting of one or more R 12 optionally substituted with R 7is a phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from one oxygen, one sulfur, and up to three nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 12 optionally replaced by; R 8 are independently hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, and each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from the group consisting of one or more R 6 optionally replaced by; R 7 and R 8 If on N, then R 7 and R 8 is oxygen, S(O)p or NR 7 can form a 3 to 7 carbon ring optionally containing: R 9 are independently C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 9 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from one oxygen, one sulfur, and up to three nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; Each R 10 are independently H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl; Each R 11are independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C(O)OR 7 , or S(O)pR 7 and; R 12 is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C8 cycloalkylalkyl, each alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl optionally substituted with halogen or cyano; Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with 1 to 3 groups, and the thiazole is optionally substituted with 1 to 2 groups, selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R 6 , C(O)R 7 , C.R. 7 (=NOR 8 ), C(O)OR 7 , C(O)NR 7 R 8 , C(S)NR 7 R 8 , OR 7 , S(O) p R 9 , SO2NR 7 R 8 optionally substituted with NR 7 R 8 , N.R. 8 C(O)R 7 , N.R.8 C(O)OR 7 , S(O)pR 7 , SO2NR 7 R 8 or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, or optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, if a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , SO2NR 7 R 8 a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with n is 1, 2, or 3; p is 0, 1, or 2.

[0005] The present invention also provides a composition comprising a compound of Formula 1 and at least one additional ingredient selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent. In one embodiment, the present invention also provides a composition for controlling and combating invertebrate pests comprising a compound of Formula 1 and at least one additional ingredient selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, the composition optionally further comprising at least one additional biologically active compound or agent.

[0006] The present invention provides methods for controlling and eradicating invertebrate pests, comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula 1 (e.g., as a composition described herein). The present invention also relates to such methods in which the invertebrate pest or its environment is contacted with a composition comprising a biologically effective amount of a compound of Formula 1 and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, the composition optionally further comprising a biologically effective amount of at least one additional bioactive compound or drug.

[0007] The present invention also provides a method for protecting seeds from invertebrate pests, comprising contacting the seeds with a biologically effective amount of a compound of Formula 1 (e.g., as a composition described herein). The present invention also relates to the treated seeds.

[0008] The present invention also provides a method for increasing the vigor of a crop plant, the method comprising contacting the crop plant, a seed in which the crop plant grows, or the locus of the crop plant (e.g., growth medium) with a biologically effective amount of a compound of Formula 1 (e.g., as a composition described herein). DETAILED DESCRIPTION OF THE INVENTION

[0009] As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having," "contains," "containing," "characterized by," or any variation thereof, are intended to include a non-exclusive inclusion, subject to any limitations specified. For example, a composition, mixture, process, or method that includes a list of elements is not necessarily limited to only those elements and may include other elements not expressly listed or inherent to such composition, mixture, process, or method.

[0010] The transitional phrase "consisting of" excludes any unspecified element, step, or ingredient. In the case of a claim, such would close the claim to the inclusion of materials other than those recited, apart from impurities normally associated therewith. When the phrase "consisting of" appears within a clause in the body of a claim rather than immediately following a preamble, it limits only the elements set forth in that clause; other elements are not excluded from the claim as a whole.

[0011] The transitional phrase "consisting essentially of" is used to define a composition or method that includes materials, steps, features, components, or elements in addition to those literally disclosed, provided that these additional materials, steps, features, components, or elements materially affect the basic and novel characteristics of the claimed invention. The term "consisting essentially of" occupies a middle ground between "comprising" and "consisting of."

[0012] It should be readily understood that where an applicant defines an invention or part thereof with open-ended terms such as "comprising," the description should (unless otherwise expressly stated) be construed as also describing such inventions using the terms "consisting essentially of" or "consisting of."

[0013] Furthermore, unless expressly stated to the contrary, "or" refers to an inclusive "or" and not an exclusive "or." For example, a condition A or B is satisfied by any one of the following: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), and both A and B are true (or exist).

[0014] Furthermore, the indefinite articles "a" and "an" preceding an element or component of the invention are intended to be open-ended regarding the number of instances (i.e., occurrences) of that element or component. Thus, "a" or "an" should be read to include one or at least one, and singular forms of elements or components also include the plural, unless the number is clearly intended to be singular.

[0015] As referred to in this disclosure, the term "invertebrate pests" includes arthropods, gastropods, nematodes, and helminthic parasites that are economically important as pests. The term "arthropods" includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs, and symphylans. The term "gastropods" includes snails, slugs, and other Stylommatophora. The term "nematodes" includes members of the phylum Nematoda.

[0016] For purposes of this disclosure, "invertebrate pest control" means the suppression of invertebrate pest development (including mortality, reduced feeding, and / or mating disruption), and related phrases are similarly defined.

[0017] The term "agricultural" refers to the production of agricultural crops such as food and fiber, and includes the growing of corn or maize, soybeans and other legumes, rice, grains (e.g., wheat, oats, barley, rye, and rice), leafy vegetables (e.g., lettuce, cabbage, and other greens), fruit vegetables (e.g., tomatoes, peppers, eggplant, crucifers, and cucurbits), potatoes, sweet potatoes, grapes, cotton, fruit trees (e.g., pome fruits, stone fruits, and citrus fruits), small fruit trees (e.g., berries and cherries), and other specialty crops (e.g., canola, sunflowers, and olives).

[0018] The term "non-agricultural" refers to non-agricultural crops such as horticultural crops (e.g., greenhouse, nursery, or ornamental plants not grown in a field), residential, agricultural, commercial, and industrial structures, turf (e.g., turf farms, pastures, golf courses, lawns, athletic fields, etc.), wood products, storage products, silviculture and vegetation management, and public health uses.

[0019] The term "crop vigor" refers to the rate of growth or biomass deposition in a crop plant. "Increased vigor" refers to an increase in growth or biomass deposition in a crop plant compared to an untreated control crop plant. The term "crop yield" refers to the harvest of crop material, both in terms of quantity and quality, obtained after harvesting the crop plant. "Increased crop yield" refers to an increase in crop yield compared to an untreated control crop plant.

[0020] The term "biologically effective amount" refers to an amount of a biologically active compound (e.g., a compound of Formula 1) sufficient to produce a desired biological effect upon application to (i.e., contact with) the invertebrate pest to be controlled or its environment, or the plant, seed or locus of the plant in which the plant grows (e.g., growth medium), to protect the plant from damage by the invertebrate pest or for other desired effect (e.g., increased plant vigor).

[0021] In the above description, the term "alkyl," whether used alone or in compound terms such as "alkylthio" or "haloalkyl," includes straight-chain or branched alkyl, for example, methyl, ethyl, n-propyl, i-propyl, or the various butyl, pentyl, or hexyl isomers.

[0022] "Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy, and the different butoxy, pentoxy, and hexyloxy isomers. "Alkylthio" includes branched and straight-chain alkylthio residues, such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio, and hexylthio isomers.

[0023] The term "halogen," whether used alone or in compound words such as "haloalkyl," or in descriptions such as "alkyl substituted with halogen," includes fluorine, chlorine, bromine, or iodine. Furthermore, when used in compound words such as "haloalkyl" or in descriptions such as "alkyl substituted with halogen," said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples of "haloalkyl" or "alkyl substituted with halogen" include F3C-, ClCH2-, CF3CH2-, and CF3CCl2-.

[0024] As used herein, the chemical abbreviations S(O) and S(=O) represent a sulfinyl moiety. As used herein, the chemical abbreviations SO, S(O), and S(=O) represent a sulfonyl moiety. As used herein, the chemical abbreviations C(O) and C(=O) represent a carbonyl moiety. As used herein, the chemical abbreviations CO, C(O)O, and C(=O)O represent an oxycarbonyl moiety. A dotted line in a structural fragment indicates the point of attachment of the fragment to the rest of the molecule. For example, if the variable Q in Formula 1 is defined as Q-1, as shown below, the dotted line in the structure of Q-1 means that Q-1 is attached to the rest of the structure of Formula 1 at that position. Additionally, in compounds of Formula 1 where Q is selected from pyridine, pyridazine, pyrimidine, and pyrazine, the pyridine, pyridazine, pyrimidine, and pyrazine are attached to the pyrazole ring of Formula 1 such that the nitrogen ring atom of the pyridine, pyridazine, pyrimidine, or pyrazine is adjacent to the point of attachment. [ka]

[0025] As noted above, Q can be pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, where the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one or more substituents selected from the group of substituents as defined in the Summary of the Invention. Non-limiting examples of the variable Q are shown in Appendix 1. Appendix 1 [ka]

[0026] The total number of carbon atoms in a substituent is indicated by the prefix "C i ~C j For example, C1-C4 alkyl refers to methyl, ethyl, and the various propyl and butyl isomers.

[0027] When a compound is substituted with a substituent bearing a subscript indicating that the number of such substituents is more than one, the substituents (if there are more than one) are independently selected from the defined group of substituents. Additionally, when a subscript is used to denote a range, e.g., (R) i~j where the group "i" is a substituted or unsubstituted group, the number of substituents may be selected from the integers i to j, inclusive. If a group contains a substituent that may be hydrogen and the substituent is then designated as hydrogen, this is considered equivalent to saying that the group is unsubstituted. When one or more positions on a group are described as "unsubstituted" or "unsubstituted," hydrogen atoms are bonded to occupy any free valence.

[0028] When a substituent is a 5- or 6-membered nitrogen-containing heterocyclic ring, it may be attached to the remainder of Formula 1 through any available carbon or nitrogen ring atom, unless otherwise specified.

[0029] A wide variety of synthetic methods are known in the art that allow the preparation of aromatic and non-aromatic heterocyclic rings and ring systems. For detailed reviews, see the eight-volume set Comprehensive Heterocyclic Chemistry (A.R. Katrittzky and C.W. Rees, editors-in-chief, Pergamon Press, Oxford, 1984) and the twelve-volume set Comprehensive Heterocyclic Chemistry II (A.R. Katrittzky, C.W. Rees, and E.F.V. Scriven, editors-in-chief, Pergamon Press, Oxford, 1996).

[0030] The compounds of the present invention can exist as one or more stereoisomers. Stereoisomers are isomers that have identical constitution but differ in the spatial arrangement of their atoms, and include enantiomers, diastereomers, cis-trans isomers (also called geometric isomers), and atropisomers. Atropisomers result from restricted rotation around a single bond, and the high barrier to rotation allows for the isolation of these isomeric species. As will be appreciated by those skilled in the art, one stereoisomer may be more reactive and / or may exhibit advantageous effects when enriched or separated from other stereoisomers. Furthermore, those skilled in the art will recognize methods for the separation, enrichment, and / or selective preparation of such stereoisomers. For a comprehensive description of all aspects of stereoisomerism, see Ernest L. Eliel and Samuel H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, 1994.

[0031] The compounds of the present disclosure can exist as a mixture of stereoisomers or as individual stereoisomers. For example, the two possible enantiomers of Formula 1 are shown as Formula 1a and Formula 1a', with the chiral carbon center identified by an asterisk (*). [ka]

[0032] The depictions of molecules drawn herein follow standard conventions for indicating stereochemistry. To indicate three-dimensional configuration, bonds rising out of the plane of the drawing, toward the viewer, are represented by solid wedges, with the wider end of the wedge attached to an atom rising out of the plane of the drawing, toward the viewer. Bonds pointing below the plane, away from the viewer, are represented by dashed wedges, with the wider end of the wedge attached to an atom pointing further away from the viewer.

[0033] The compounds of the present disclosure may exist as stereoisomers due to possible chiral carbon atoms present in Formula 1. Thus, the present disclosure includes individual stereoisomers of the compounds of Formula 1 as well as mixtures of stereoisomers of the compounds of Formula 1.

[0034] Compounds of Formula 1 may contain additional chiral centers, and the present disclosure also includes racemic mixtures enriched and having substantially pure stereoconfigurations at these additional chiral centers.

[0035] Compounds of the present disclosure may exist as one or more conformers due to restricted rotation about any bond in Formula 1. The present disclosure includes mixtures of conformers. In addition, the present disclosure includes compounds enriched in one conformer relative to another.

[0036] The more biologically active enantiomer is believed to be the R enantiomer of Formula 1a (Formula 1).

[0037] The present disclosure includes a racemic mixture of equal amounts of the enantiomers of Formula 1a (the S enantiomer of Formula 1) and 1a' (the R enantiomer of Formula 1). Additionally, the present disclosure includes mixtures enriched in the enantiomer of Formula 1a compared to the racemic mixture of Formulas 1a and 1a'. The present disclosure also includes essentially pure enantiomers of Formula 1a.

[0038] An embodiment of the present disclosure includes a mixture of stereoisomers of compounds of formula 1a and 1a', in which the ratio of 1a to 1a' is at least 75:25 (50% enantiomeric excess).

[0039] An embodiment of the present disclosure includes a mixture of stereoisomers of compounds of formula 1a and 1a', in which the ratio of 1a to 1a' is at least 90:10 (80% enantiomeric excess of 1a).

[0040] An embodiment of the present disclosure includes a mixture of stereoisomers of compounds of formula 1a and 1a', in which the ratio of 1a to 1a' is at least 95:5 (90% enantiomeric excess of 1a).

[0041] An embodiment of the present disclosure includes a mixture of stereoisomers of compounds of formula 1a and 1a', in which the ratio of 1a to 1a' is at least 98:2 (96% enantiomeric excess of 1a).

[0042] An embodiment of the present disclosure includes a mixture of stereoisomers of compounds of formula 1a and 1a', in which the ratio of 1a to 1a' is at least 99:1 (98% enantiomeric excess of 1a).

[0043] An embodiment of the present disclosure includes a mixture of stereoisomers of compounds of formula 1a and 1a', in which the ratio of 1a to 1a' is essentially 100:0.

[0044] An embodiment of the present disclosure includes a compound of formula 1a:

[0045] Compounds selected from Formula 1 typically exist in more than one form, and thus Formula 1 encompasses all crystalline and amorphous forms of the compounds represented by Formula 1. Amorphous forms include solid embodiments, such as waxes and rubbers, as well as liquid embodiments, such as solutions and melts. Crystalline forms include embodiments that exhibit a substantially single crystal type and embodiments that exhibit a mixture of polymorphs (i.e., multiple crystalline types). The term "polymorph" refers to a particular crystalline form of a compound that can crystallize in various crystalline forms, which have different molecular arrangements and / or conformations in the crystal lattice. Polymorphs can have the same chemical composition, but they can also differ in composition due to the presence or absence of co-crystallized water or other molecules that may be weakly or strongly bound in the lattice. Polymorphs can differ in chemical, physical, and biological properties, such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspendability, dissolution rate, and bioavailability. Those skilled in the art will appreciate that a particular polymorph of the compound represented by Formula 1 may exhibit advantageous effects (e.g., suitability in preparing useful formulations, improved biological performance) compared to other polymorphs or mixtures of polymorphs of the same compound represented by Formula 1. Preparation and isolation of a particular polymorph of the compound represented by Formula 1 can be achieved by methods known to those skilled in the art, such as, for example, crystallization using selected solvents and temperatures. The compounds of the present invention may exist as one or more crystalline polymorphs. The present disclosure includes both individual polymorphs and mixtures of polymorphs, including mixtures enriched in one polymorph relative to other polymorphs. For a comprehensive discussion of polymorphism, see R. Hilfiker, Ed., Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006. Embodiments of the present invention described in the Summary include those described below. In the following embodiments, Formula 1 includes its stereoisomers, N-oxides, and salts.

[0046] Embodiment 1: A compound of Formula 1, wherein X is O.

[0047] Embodiment 1a: A compound of Formula 1 wherein X is S.

[0048] Embodiment 2: A is CR 1 A compound of Formula 1, embodiment 1 or embodiment 1a, wherein:

[0049] Embodiment 2a: A compound of Formula 1, Embodiment 1 or Embodiment 1a, wherein A is CH.

[0050] Embodiment 2b: A compound of Formula 1, embodiment 1 or embodiment 1a, wherein A is N.

[0051] Embodiment 3: R 1 are independently H, amino, cyano, halogen, nitro, C(S)NH; or R 1 are independently C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 1 is independently phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, and each phenyl or heteroaromatic ring is selected from one or more R 6 optionally substituted with R 1 are independently C3-C9-trialkylsilyl, C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , OS(O)2R 9 , or S(=NR 11 )O p R 9 or R 1 is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , or SO2NR 7 R 8 and 1-4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1-4 nitrogen atoms, substituted with

[0052] Embodiment 3a:R 1 are independently amino, cyano, halogen, nitro, C(S)NH; or R 1 are independently C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 1is independently phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, and each phenyl or heteroaromatic ring is selected from one or more R 6 optionally substituted with R 1 are independently C3-C9-trialkylsilyl, C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , OS(O)2R 9 , or S(=NR 11 )O p R 9 or R 1 is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , or SO2NR 7 R 8A compound according to Formula 1 or any of the preceding embodiments, wherein R is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with

[0053] Embodiment 3b: R 1 are independently cyano, halogen, nitro, or C(S)NH; or R 1 are independently C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, or C3-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally replaced by R 1 are independently C3-C9-trialkylsilyl, C(O)C1-C6, CR 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , OS(O)2R 9 , or S(=NR 11 )O p R 9 or R 1is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , or S(O)pR 7 and 1-4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1-4 nitrogen atoms, substituted with

[0054] Embodiment 3c: R 1 is a halogen, or R 1 is C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, or C3-C6 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 1 C3-C9-trialkylsilyl, C(O)C1-C6, CR 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , OS(O)2R9 , or S(=NR 11 )O p R 9 or R 1 is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, C(O)R 7 or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1-4 nitrogen atoms, substituted with C(O)OC1-C6.

[0055] Embodiment 3d: R 1 is a halogen, or R 1 is C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, or each alkyl, alkenyl, or alkynyl is selected from the group consisting of one or more R 6 optionally substituted with R 1 C(O)C1~C6, CR 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , or OS(O)2R 9A compound according to Formula 1 or any of the preceding embodiments, wherein:

[0056] Embodiment 3e:R 1 is a halogen, or R 1 is C1-C3 alkyl, C2-C4 alkenyl, or C2-C4 alkynyl, and each alkyl, alkenyl, or alkynyl is selected from one or more R 6 optionally substituted with R 1 But C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , or OS(O)2R 9 A compound according to Formula 1 or any of the preceding embodiments, wherein:

[0057] Embodiment 3f:R 1 is a halogen, or R 1 is C1-C3 alkyl or C2-C4 alkenyl, and each alkyl or alkenyl is selected from one or more R 6 optionally substituted with R 1 But, CR 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , or OS(O)2R 9 A compound according to Formula 1 or any of the preceding embodiments, wherein:

[0058] Embodiment 3g: R 1 is a halogen, or R 1 is a C1-C3 alkyl, and each alkyl is selected from one or more R 6 optionally substituted with R 1 But, OR 7 , SCF3 or OS(O)2R 9 A compound according to Formula 1 or any of the preceding embodiments, wherein:

[0059] Embodiment 3h:R 1 is Cl, F, or Br, or R 1 is a C1-C3 alkyl, and each alkyl is selected from one or more R 6 optionally substituted with R 1 But, OR 7 , SCC3 or OS(O)2R 9 A compound according to Formula 1 or any of the preceding embodiments, wherein:

[0060] Embodiment 3i:R 1 is Cl, F, or Br, or R 1 is a C1-C3 alkyl, and each alkyl is selected from one or more R 6 optionally substituted with R 1 is OMe, SCF3, or OS(O)2R 9 A compound according to Formula 1 or any of the preceding embodiments, wherein:

[0061] Embodiment 3j:R 1 is Cl, F, or Br, or R 1 but one or more R 6 Me optionally substituted with R 1 is OMe, SCF3, or OS(O)2R 9 A compound according to Formula 1 or any of the preceding embodiments, wherein:

[0062] Embodiment 3k:R 1 is Cl, F, or Br, or R 1 is a C1-C3 alkyl, and each alkyl is selected from one or more R 6 A compound according to formula 1 or any of the preceding embodiments, optionally substituted with:

[0063] Embodiment 3l:R 1 is Cl, or R 1 but one or more R 6 A compound of formula 1 or any of the preceding embodiments, wherein R is Me optionally substituted with

[0064] Embodiment 3: n is 2 and each R 1 is Cl, or each R 1 is CF3 or one R 1 is Cl and one R 1 is CF.

[0065] Embodiment 3n: n is 2 and each R 1 is located at the 3- and 5-positions of the phenyl ring.

[0066] Embodiment 4: R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6optionally substituted with R 2 but one or more R 6 and substituted with phenyl, or a 4-6 membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 2 nitrogen atoms, or a 5 membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6 membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or heterocyclic ring is optionally substituted with one or more R 6 optionally substituted with R 2 But C(O)R 7 , C(O)OR 7 , N.R. 7 R 8 , OR 7 , S(O)pR 9 or SO2NR 7 R 8 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0067] Embodiment 4a:R 2 is hydrogen, C1-C4 alkyl, or C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R 6 A compound according to formula 1 or any one of the preceding embodiments, optionally substituted with:

[0068] Embodiment 4b: R 2 is hydrogen or C1-C4 alkyl, and each alkyl is selected from one R 6 optionally substituted with R 2 But C(O)R 7 or C(O)OR 7 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0069] Embodiment 4c: R2 is hydrogen or C1-C4 alkyl, and each alkyl is selected from one R 6 optionally substituted with R 2 But C(O)R 7 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0070] Embodiment 4d: R 2 is H or C1-C4 alkyl, and each alkyl is selected from one R 6 A compound according to formula 1 or any one of the preceding embodiments, optionally substituted with:

[0071] Embodiment 4e:R 2 is H or C1-C3 alkyl, and each alkyl is selected from one R 6 A compound according to formula 1 or any one of the preceding embodiments, optionally substituted with:

[0072] Embodiment 4f:R 2 is H, C1-C3 alkyl, or CH2c-Pr.

[0073] Embodiment 4f:R 2 is H, or Me.

[0074] Embodiment 5: R 3 is C1-C3 alkyl or C1-C3 haloalkyl.

[0075] Embodiment 5a:R 3 is C1-C3 alkyl.

[0076] Embodiment 5b: R 3 is Me.

[0077] Embodiment 6: R4 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 4 But C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , S(O)pR 9 , SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0078] Embodiment 6a:R 4 is hydrogen, cyano, halogen, nitro, or C1-C3 alkyl, and alkyl is one or more R 6 or R 4 But NR 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , S(O)pR 9 , SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0079] Embodiment 6b: R4 is hydrogen, cyano, halogen, nitro, or C1-C3 alkyl, and alkyl is one or more R 6 or R 4 But NR 7 R 8 , N.R. 8 C(O)R 7 , OR 7 , S(O)pR 9 , or SO2NR 7 R 8 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0080] Embodiment 6b: R 4 is hydrogen, cyano, halogen, nitro, or C1-C3 alkyl, and alkyl is one or more R 6 or R 4 But NR 7 R 8 , N.R. 8 C(O)R 7 , OR 7 , or S(O)pR 9 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0081] Embodiment 6c: R 4 is hydrogen, cyano, nitro, Cl, or C1-C3 alkyl, and alkyl is selected from one or more R 6 or R 4 But NR 7 R 8 , N.R. 8 C(O)R 7 , OR 7 , or S(O)pR 9 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0082] Embodiment 6d: R 4 is cyano, nitro, or SO2Me.

[0083] Embodiment 7: R 5is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6-alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 5 But C(O)R 7 , C.R. 7 (=NO)R 8 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , N.R. 11 SO2NR 7 R 8 , OR 7 , S(O)pR 9 , or SO2NR 7 R 8 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0084] Embodiment 7a:R 5 is hydrogen, halogen, nitro, C1-C3-alkyl or C3-C6-cycloalkyl, and each alkyl or cycloalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 5 But, OR 7 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , or SO2NR 7 R 8 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0085] Embodiment 7b: R 5is hydrogen, cyano, halogen, nitro, or C-C-alkyl or C-C-cycloalkyl, and each alkyl is selected from one or more R 6 optionally substituted with R 5 But, OR 7 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , or SO2NR 7 R 8 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0086] Embodiment 7c: R 5 is hydrogen, cyano, halogen, nitro, or C1-C3-alkyl, and each alkyl or cycloalkyl is selected from one or more R 6 optionally substituted with R 5 But, OR 7 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , or SO2NR 7 R 8 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0087] Embodiment 7d:R 5 is hydrogen, cyano, halogen, nitro, or C1-C3-alkyl; or R 5 But, OR 7 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , or SO2NR 7 R 8 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0088] Embodiment 7e:R 5 is hydrogen, halogen, or R 5 But, OR 7 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , or NR 8 C(O)OR 7 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0089] Embodiment 7f:R 5 is hydrogen, cyano, Br, Cl, F, nitro, or C1-C3-alkyl; or R 5 But, OR 7 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , or SO2NR 7 R 8 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0090] Embodiment 7g:R 5 is hydrogen, cyano, Br, Cl, F, nitro, or C1-C3-alkyl; or R 5 But, OR 7 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , or NR 8 C(O)OR 7 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0091] Embodiment 7h:R 5 is hydrogen, cyano, Br, Cl, F, nitro, or Me; or R 5 But, OR 7 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , or NR8 C(O)OR 7 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0092] Embodiment 7i:R 5 is hydrogen, cyano, Br, Cl, F, nitro, or Me; or R 5 is OMe, NH2, NHMe, SMe, N(Me)2, or NHC(O)Me.

[0093] Embodiment 7j:R 5 is hydrogen, cyano, Cl, nitro, or Me; or R 5 is OMe, NH2, NHMe, SMe, N(Me)2, or NHC(O)Me.

[0094] Embodiment 8: R 6 is halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 ,OC(O)OR 7 , S(O)pR 9 , SO2NR 7 R 8 , or S(=NR)O p R 7 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0095] Embodiment 8a:R 6 is halogen, cyano, nitro, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 ,OC(O)OR 7 , SF5, S(O)pR 9 , or SO2NR 7 R 8 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0096] Embodiment 8b: R 6 is halogen, cyano, nitro, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , or C(O)NR 7 R 8 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0097] Embodiment 8c:R 6 is halogen, cyano, nitro, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, or C3-C7 cycloalkyl.

[0098] Embodiment 8d:R 6The compound of Formula 1 or any one of the preceding embodiments, wherein is halogen, cyano, C1-C3 alkyl, or C1-C3 haloalkyl.

[0099] Embodiment 8e:R 6 A compound according to Formula 1 or any one of the preceding embodiments, wherein is F, cyano, C1-C3 alkyl, or C1-C3 haloalkyl.

[0100] Embodiment 9:R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 7 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 A compound according to formula 1 or any one of the preceding embodiments, optionally substituted with:

[0101] Embodiment 9a:R 7 is hydrogen, C1-C3 alkyl, C2-C3 alkenyl, C3-C4 alkynyl, C3-C6 cycloalkyl, or C5-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from the group consisting of one or more R 12 optionally substituted with R 7 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 12A compound according to formula 1 or any one of the preceding embodiments, optionally substituted with:

[0102] Embodiment 10:R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, and each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from the group consisting of one or more R 6 optionally substituted with R 7 and R 8 If on N, then R 7 and R 8 is oxygen, S(O)p or NR 7 A compound according to formula 1 or any one of the preceding embodiments, which can form a ring of 3 to 7 carbons optionally containing:

[0103] Embodiment 10a:R 8 is hydrogen, or C1-C3, C1-C3 alkoxy, C3-C4 alkenyl, C4-C5 alkenyloxy, C3-C5 alkynyl, or C4-C5 alkynyloxy, and each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from the group consisting of one or more R 6 A compound according to formula 1 or any one of the preceding embodiments, optionally substituted with:

[0104] Embodiment 11:R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more R 6 optionally substituted with R 9is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 A compound according to formula 1 or any one of the preceding embodiments, optionally substituted with:

[0105] Embodiment 11a:R 9 is C1-C3 alkyl, C3-C5 alkenyl, C3-C5 alkynyl, or C4-C6 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more R 6 optionally substituted with R 9 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 A compound according to formula 1 or any one of the preceding embodiments, optionally substituted with:

[0106] Embodiment 11b:R 9 is C1-C3 alkyl, C3-C5 alkenyl, C3-C5 alkynyl, or C4-C6 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more R 6 A compound according to formula 1 or any one of the preceding embodiments, optionally substituted with:

[0107] Embodiment 12:R 10 is H, C1-C6 alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C3-alkyl, or C1-C3-alkoxy-C1-C3-alkyl.

[0108] Embodiment 12a:R 10 is H, C1-C6 alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C3-alkyl.

[0109] Embodiment 12b:R 10 is H, C1-C6 alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl.

[0110] Embodiment 12c:R 10 is H, C1-C6 alkyl, C1-C6-haloalkyl.

[0111] Embodiment 13:R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C(O)OR 7 , or S(O)pR 7 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0112] Embodiment 13a:R 11 is hydrogen, C1-C3 alkyl, C3-C5 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C(O)OR 7 , or S(O)pR 7 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0113] Embodiment 14:R12 is halogen, hydroxy, cyano, nitro, SF, C(O)NH, C(S)NH, C-C alkyl, C-C alkoxy, C-C alkenyl, C-C alkynyl, C-C cycloalkyl, C-C cycloalkylalkyl, wherein each alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is optionally substituted with halogen or cyano.

[0114] Embodiment 14a:R 12 is halogen, hydroxy, cyano, nitro, SF, C(O)NH, C(S)NH, C-C alkyl, C-C alkoxy, C-C alkenyl, C-C alkynyl, each alkyl, alkoxy, alkenyl, alkynyl optionally substituted with halogen or cyano.

[0115] Embodiment 14b:R 12 is halogen, hydroxy, cyano, nitro, SF, C(O)NH, C(S)NH, C-C alkyl, each alkyl optionally substituted with halogen or cyano.

[0116] Embodiment 15: Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with 1-3 groups, and the thiazole is optionally substituted with 1-2 groups selected from amino, cyano, halogen, nitro, C-C alkyl, C-C alkenyl, C-C alkynyl, C-C cycloalkyl, or C-C cycloalkylalkyl, and wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R 6 , C(O)R 7 , C.R. 7 (=NOR 8 ), C(O)OR 7 , C(O)NR7 R 8 , C(S)NR 7 R 8 , OR 7 , S(O) p R 9 , SO2NR 7 R 8 optionally substituted with NR 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , SO2NR 7 R 8 or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, if a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , SO2NR 7 R 8 and 1 to 4 heteroatoms independently selected from one oxygen, one sulfur, and one to four nitrogen atoms, substituted by:

[0117] Embodiment 15a: Q is pyridine, pyridazine, pyrimidine, or pyrazine, and the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with 1 to 3 groups selected from amino, cyano, halogen, nitro, C-C alkyl, C-C cycloalkylalkyl, C-C alkenyl, C-C alkynyl, C-C cycloalkyl, or cycloalkylalkyl, and each alkyl, alkoxy, cycloalkyloxy, alkoxyalkoxy, alkoxyalkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R 6 , C(O)R 7 , C.R. 7 (=NOR 8 ), C(O)OR 7 , C(O)NR 7 R 8 , C(S)NR 7 R 8 , OR 7 , S(O) p R 9 , SO2NR 7 R 8 optionally substituted with NR 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , SO2NR 7 R 8 or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy, or optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy, or, if a nitrogen atom is present, C(O)R 7 , C(O)OR 7, C(O)NR 7 R 8 , S(O)pR 7 , SO2NR 7 R 8 and 1 to 4 heteroatoms independently selected from one oxygen, one sulfur, and one to four nitrogen atoms, substituted by:

[0118] Embodiment 15b: Q is pyridine, pyridazine, or pyrimidine, and the pyridine, pyridazine, or pyrimidine is optionally substituted with 1 to 3 groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R 6 , C(O)R 7 , C.R. 7 (=NOR 8 ), C(O)OR 7 , C(O)NR 7 R 8 , C(S)NR 7 R 8 , OR 7 , S(O) p R 9 , SO2NR 7 R 8 optionally substituted with NR 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , SO2NR 7 R 8or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, if a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , SO2NR 7 R 8 and 1 to 4 heteroatoms independently selected from one oxygen, one sulfur, and one to four nitrogen atoms, substituted by:

[0119] Embodiment 15c: A compound according to Formula 1 or any one of the preceding embodiments, wherein Q is selected from Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, Q-25, and Q-26.

[0120] Embodiment 15d: A compound according to Formula 1 or any one of the preceding embodiments, wherein Q is selected from Q-1, Q-2, Q-6, Q-7, Q-11, Q-13, Q-14, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, and Q-25.

[0121] Embodiment 15e: A compound according to Formula 1 or any one of the preceding embodiments, wherein Q is selected from Q-1, Q-2, Q-13, Q-14, Q-19, and Q-24.

[0122] Embodiment 15f: A compound according to Formula 1 or any one of the preceding embodiments, wherein Q is selected from Q-1, and Q-2.

[0123] Embodiment 15g: A compound according to Formula 1 or any one of the preceding embodiments, wherein Q is Q-2.

[0124] Embodiment 16: A compound according to Formula 1 or any one of the preceding embodiments, wherein n is 1 or 2.

[0125] Embodiment 16a: A compound according to Formula 1 or any one of the preceding embodiments, wherein n is 2.

[0126] Embodiment 17: A compound according to Formula 1 or any one of the preceding embodiments, wherein p is 0 or 1.

[0127] Embodiment 17a: A compound according to Formula 1 or any one of the preceding embodiments, wherein p is 0.

[0128] Embodiments of the present disclosure, including embodiments 1-17a above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of the variables in the embodiments relate not only to compounds of Formula 1, but also to starting compounds and intermediate compounds useful for preparing compounds of Formula 1. Additionally, embodiments of the present disclosure, including embodiments 1-17a above as well as any other embodiments described herein, and any combination thereof, relate to the compositions and methods of the present disclosure.

[0129] In some embodiments, R 1 is other than H, then R 1 is not located adjacent to C(X).

[0130] In some embodiments, R 4 and R5 are not both hydrogen.

[0131] In some embodiments, R 1 is other than H, then R 1 is not adjacent to C(X) and R 4 and R 5 are not both hydrogen.

[0132] Embodiment X. A method for controlling and combating invertebrate pests comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula 1.

[0133] Embodiment X1. The method of claim X, wherein the environment is soil or plant foliage.

[0134] Embodiments of the present disclosure, including Embodiments 1-X1 above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of the variables in the embodiments relate not only to compounds of Formula 1, but also to starting compounds and intermediate compounds useful for preparing compounds of Formula 1. In addition, embodiments of the present disclosure, including Embodiments 1-X1 above as well as any other embodiments described herein, and any combination thereof, relate to the compositions and methods of the present disclosure.

[0135] Combinations of embodiments 1 to 17a are shown below.

[0136] Embodiment A1. A compound of Formula 1, X is O; n is 1, 2, or 3; p is 0, 1, or 2; A is CH; R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 1 is a phenyl or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, and each phenyl or heteroaromatic ring is selected from one or more R 6 optionally substituted with R 1 C3-C9-trialkylsilyl, C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , OS(O)2R 9 , or S(=NR 11 )O p R 9 or R 1is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , or SO2NR 7 R 8 a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 2 but one or more R 6 and substituted with phenyl, or a 4-6 membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 2 nitrogen atoms, or a 5 membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6 membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or heterocyclic ring is optionally substituted with one or more R 6 optionally substituted with R 2 But C(O)R 7 , C(O)OR 7 , N.R. 7 R 8 , OR 7 , S(O)pR 9 or SO2NR 7 R8 and; R 3 is C1-C3 alkyl or C1-C3 haloalkyl; R 4 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , S(O)pR 9 , SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 and; R 5 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6-alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C.R. 7 (=NO)R 8 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , N.R.11 SO2NR 7 R 8 , OR 7 , S(O)pR 9 , or SO2NR 7 R 8 and; R 6 is halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , C(O)NR 7 R 8 , N.R. 7 R 8 , NR8C(O)R7, NR8C(O)OR7, OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 ,OC(O)OR 7 , S(O)pR 9 , SO2NR 7 R 8 , or S(=NR)O p R 7 and; R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl or cycloalkylalkyl is selected from the group consisting of one or more R 12 optionally substituted with R 7 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 12 optionally replaced by; R 8is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, and each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from the group consisting of one or more R 6 optionally replaced by; When R7 and R8 are on N, R7 and R8 are oxygen, S(O)p or NR 7 can form a 3 to 7 carbon ring optionally containing: R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more R 6 optionally substituted with R 9 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl; R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C(O)OR 7 , or S(O)pR 7 and; R 12is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C8 cycloalkylalkyl, each alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl optionally substituted with halogen or cyano; Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with 1 to 3 groups and the thiazole is optionally substituted with 1 to 2 groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R 6 , C(O)R 7 , C.R. 7 (=NOR 8 ), C(O)OR 7 , C(O)NR 7 R 8 , C(S)NR 7 R 8 , OR 7 , S(O) p R 9 , SO2NR 7 R 8 optionally substituted with NR 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , SO2NR 7 R 8or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, if a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , SO2NR 7 R 8 and a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with

[0137] Embodiment A2. X is O; n is 1, 2, or 3; p is 0, 1, or 2; A is CH; R 1 is a halogen or R 1 is C1-C3 alkyl or C2-C4 alkenyl, and each alkyl or alkenyl is selected from one or more R 6 optionally substituted with R 1 But, CR 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7, OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , or OS(O)2R 9 and; R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 2 but one or more R 6 and substituted with phenyl, or a 4-6 membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 2 nitrogen atoms, or a 5 membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6 membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or heterocyclic ring is optionally substituted with one or more R 6 optionally substituted with R 2 But C(O)R 7 , C(O)OR 7 , N.R. 7 R 8 , OR 7 , S(O)pR 9 or SO2NR 7 R 8 and; R 3 is C1-C3 alkyl; R 4is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , S(O)pR 9 , SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 and; R 5 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6-alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C.R. 7 (=NO)R 8 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , N.R. 11 SO2NR 7 R 8 , OR 7 , S(O)pR 9 , or SO2NR7 R 8 and; R 6 is halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , C(O)NR 7 R 8 , N.R. 7 R 8 , NR8C(O)R7, NR8C(O)OR7, OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 ,OC(O)OR 7 , S(O)pR 9 , SO2NR 7 R 8 , or S(=NR)O p R 7 and; R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl or cycloalkylalkyl is selected from the group consisting of one or more R 12 optionally substituted with R 7 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 12 optionally replaced by; R 8is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, and each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from the group consisting of one or more R 6 optionally replaced by; R 7 and R 8 If on N, then R 7 and R 8 is oxygen, S(O)p or NR 7 can form a 3 to 7 carbon ring optionally containing: R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 9 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl; R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C(O)OR 7 , or S(O)pR 7 and; R 12is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 alkoxy, C2-C6 alkenyl, C4-C8 cycloalkylalkyl, each alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl optionally substituted with halogen or cyano; Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with 1 to 3 groups and the thiazole is optionally substituted with 1 to 2 groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R 6 , C(O)R 7 , C.R. 7 (=NOR 8 ), C(O)OR 7 , C(O)NR 7 R 8 , C(S)NR 7 R 8 , OR 7 , S(O) p R 9 , SO2NR 7 R 8 optionally substituted with NR 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , SO2NR 7 R 8or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, if a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , SO2NR 7 R 8 A compound of Formula 1 or Embodiment A1, wherein the heterocyclic ring is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted by

[0138] Embodiment A3. X is O; n is 1, 2, or 3; p is 0, 1, or 2; A is CH; R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 1is a phenyl or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, and each phenyl or heteroaromatic ring is selected from one or more R 6 optionally substituted with R 1 C3-C9-trialkylsilyl, C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , OS(O)2R 9 , or S(=NR 11 )O p R 9 or R 1 is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , or SO2NR 7 R 8a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 2 but one or more R 6 and substituted with phenyl, or a 4-6 membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 2 nitrogen atoms, or a 5 membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6 membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or heterocyclic ring is optionally substituted with one or more R 6 optionally substituted with R 2 But C(O)R 7 , C(O)OR 7 , N.R. 7 R 8 , OR 7 , S(O)pR 9 or SO2NR 7 R 8 and; R 3 is C1-C3 alkyl; R 4 is hydrogen, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6optionally substituted with; C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , S(O)pR 9 , SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 and; R 5 is hydrogen, cyano, halogen, nitro, C1-C6-alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C.R. 7 (=NO)R 8 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , N.R. 11 SO2NR 7 R 8 , OR 7 , S(O)pR 9 , or SO2NR 7 R 8 and; R 6 is halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR10 , C(O)NR 7 R 8 , N.R. 7 R 8 , NR8C(O)R7, NR8C(O)OR7, OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 ,OC(O)OR 7 , S(O)pR 9 , SO2NR 7 R 8 and; R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl or cycloalkylalkyl is selected from the group consisting of one or more R 12 optionally substituted with R 7 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 12 optionally replaced by; R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, and each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from the group consisting of one or more R 6 optionally replaced by; R 7 and R 8 If on N, then R 7 and R 8 is oxygen, S(O)p or NR 7 can form a 3 to 7 carbon ring optionally containing: R 9is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 9 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl; R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C(O)OR 7 , or S(O)pR 7 and; R 12 is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, each alkyl optionally substituted with halogen or cyano; Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with 1 to 3 groups and the thiazole is optionally substituted with 1 to 2 groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R 6 , C(O)R 7 , C.R. 7 (=NOR 8 ), C(O)OR 7 , C(O)NR 7 R 8 , C(S)NR 7 R 8 , OR 7 , S(O) p R 9 , SO2NR 7 R 8 optionally substituted with NR 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , SO2NR 7 R 8 or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, if a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8, S(O)pR 7 , SO2NR 7 R 8 A compound of Formula 1 or Embodiment A1, wherein the heterocyclic ring is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted by

[0139] Embodiment A4. X is O; n is 1, 2, or 3; p is 0, 1, or 2; A is CH; R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 1 is a phenyl or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, and each phenyl or heteroaromatic ring is selected from one or more R 6 optionally substituted with R 1 C3-C9-trialkylsilyl, C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , OS(O)2R 9 , or S(=NR 11 )O p R 9 or R 1 is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , or SO2NR 7 R 8 a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 2 but one or more R 6and substituted with phenyl, or a 4-6 membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 2 nitrogen atoms, or a 5 membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6 membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or heterocyclic ring is optionally substituted with one or more R 6 optionally substituted with R 2 But C(O)R 7 , C(O)OR 7 , N.R. 7 R 8 , OR 7 , S(O)pR 9 or SO2NR 7 R 8 and; R 3 is C1-C3 alkyl; R 4 is hydrogen, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally replaced by; R 5 is hydrogen, cyano, halogen, nitro, C1-C6-alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 5 But C(O)R 7 , C.R. 7 (=NO)R 8 , C(O)OR 7 , C(O)NR 7 R8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , S(O)pR 9 , or SO2NR 7 R 8 and; R 6 is halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 ,OC(O)OR 7 , S(O)pR 9 , SO2NR 7 R 8 and; R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 7is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, and each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from the group consisting of one or more R 6 optionally replaced by; R 7 and R 8 If on N, then R 7 and R 8 is oxygen, S(O)p or NR 7 can form a 3 to 7 carbon ring optionally containing: R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 9 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl; R 11is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C(O)OR 7 , or S(O)pR 7 and; Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with 1 to 3 groups and the thiazole is optionally substituted with 1 to 2 groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R 6 , C(O)R 7 , C.R. 7 (=NOR 8 ), C(O)OR 7 , C(O)NR 7 R 8 , C(S)NR 7 R 8 , OR 7 , S(O) p R 9 , SO2NR 7 R 8 optionally substituted with NR 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , SO2NR 7 R 8or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, if a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , SO2NR 7 R 8 A compound of Formula 1 or Embodiment A1, wherein the heterocyclic ring is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted by

[0140] Embodiment A5. X is O; n is 1, 2, or 3; p is 0, 1, or 2; A is CH; R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 1is a phenyl or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, and each phenyl or heteroaromatic ring is selected from one or more R 6 optionally substituted with R 1 C3-C9-trialkylsilyl, C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , OS(O)2R 9 , or S(=NR 11 )O p R 9 or R 1 is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , or SO2NR 7 R 8a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 2 but one or more R 6 and substituted with phenyl, or a 4-6 membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 2 nitrogen atoms, or a 5 membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6 membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or heterocyclic ring is optionally substituted with one or more R 6 optionally substituted with R 2 But C(O)R 7 , C(O)OR 7 , N.R. 7 R 8 , OR 7 , S(O)pR 9 or SO2NR 7 R 8 and; R 3 is C1-C3 alkyl; R 4 is hydrogen, cyano, halogen, nitro, C1-C6 alkyl, and each alkyl is one or more R 6 optionally replaced by; R 5is hydrogen, cyano, halogen, nitro, C1-C6-alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 5 But NR 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , S(O)pR 9 , or SO2NR 7 R 8 and; R 6 is halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 ,OC(O)OR 7 , S(O)pR 9 , or SO2NR 7 R 8 and; R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 7 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, and each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from the group consisting of one or more R 6 optionally replaced by; R 7 and R 8 If on N, then R 7 and R 8 is oxygen, S(O)p or NR 7 can form a 3 to 7 carbon ring optionally containing: R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 9 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl; R 11is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C(O)OR 7 , or S(O)pR 7 and; Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with 1 to 3 groups and the thiazole is optionally substituted with 1 to 2 groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R 6 , C(O)R 7 , C.R. 7 (=NOR 8 ), C(O)OR 7 , C(O)NR 7 R 8 , C(S)NR 7 R 8 , OR 7 , S(O) p R 9 , SO2NR 7 R 8 optionally substituted with NR 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , SO2NR 7 R 8or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, if a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , SO2NR 7 R 8 A compound of Formula 1 or Embodiment A1, wherein the heterocyclic ring is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted by

[0141] Embodiment A6. X is O; n is 1, 2, or 3; p is 0, 1, or 2; A is CH; R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 1is a phenyl or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, and each phenyl or heteroaromatic ring is selected from one or more R 6 optionally substituted with R 1 C3-C9-trialkylsilyl, C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , OS(O)2R 9 , or S(=NR 11 )O p R 9 or R 1 is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , or SO2NR 7 R 8a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 2 but one or more R 6 C1-C6 alkyl optionally substituted with; R 3 is Me; R 4 is hydrogen, cyano, halogen, nitro, C1-C3 alkyl, and each alkyl is selected from one or more R 6 optionally replaced by; R 5 is hydrogen, cyano, halogen, or nitro; or R 5 But NR 7 R 8 , N.R. 8 C(O)R 7 , OR 7 , S(O)pR 9 , or SO2NR 7 R 8 and; R 6 is halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 ,OC(O)OR 7 , S(O)pR 9 , SO2NR 7 R 8 and; R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 7 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, and each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from the group consisting of one or more R 6 optionally replaced by; R 7 and R 8 If on N, then R 7 and R8 is oxygen, S(O)p or NR 7 can form a 3 to 7 carbon ring optionally containing: R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 9is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl; R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C(O)OR 7 , or S(O)pR 7 and; Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with 1 to 3 groups and the thiazole is optionally substituted with 1 to 2 groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R 6 , C(O)R 7 , C.R. 7 (=NOR 8 ), C(O)OR 7 , C(O)NR 7 R 8 , C(S)NR 7 R 8 , OR 7 , S(O) p R 9 , SO2NR 7 R 8optionally substituted with NR 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , SO2NR 7 R 8 or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, if a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , SO2NR 7 R 8 A compound of Formula 1 or Embodiment A1, wherein the heterocyclic ring is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted by

[0142] Embodiment A7. X is O; n is 1 or 2; p is 0, 1, or 2; A is CH; R 1 is a halogen; or R 1 is a C1-C6 alkyl, and each alkyl is selected from one or more R 6 optionally replaced by; R 2 is hydrogen or C1-C6 alkyl; R 3 is Me; R 4 is cyano or nitro; R 5 is hydrogen, cyano, halogen, or nitro; or R 5 But NR 7 R 8 , N.R. 8 C(O)R 7 , OR 7 , S(O)pR 9 , or SO2NR 7 R 8 and; R 6 is halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 ,OC(O)OR 7 , S(O)pR 9 , SO2NR 7 R 8 and; R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 7is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, and each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from the group consisting of one or more R 6 optionally replaced by; R 7 and R 8 If on N, then R 7 and R8 is oxygen, S(O)p or NR 7 can form a 3 to 7 carbon ring optionally containing: R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 9 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl; R 11is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C(O)OR 7 , or S(O)pR 7 and Q is A compound according to formula 1 or embodiment A1 selected from Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, Q-25, and Q-26.

[0143] Embodiment A8. A is CH; N is 1 or 2; R 1 is Cl or F, or R 1 but one or more R 6 Me optionally substituted with; R 2 is hydrogen, CH2c-Pr, or Me; R 3 is Me; R 4 is hydrogen, cyano, halogen, nitro, or C1-C3 alkyl, and alkyl is one or more R 6 optionally substituted with; or R 4 But NR 7 R 8 , N.R. 8 C(O)R 7 , OR 7 , or S(O)pR 9 and; R 5 is hydrogen, cyano, Br, Cl, F, nitro, or C1-C3-alkyl; or R 5 But, OR 7 , N.R. 7 R 8 , N.R.8 C(O)R 7 , or NR 8 C(O)OR 7 and A compound according to formula 1 or embodiment A1, wherein Q is Q-1, Q-2, Q-6, Q-7, Q-11, Q-13, Q-14, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, or Q-25.

[0144] Embodiment A9. X is O; A is CH; n is 2; R 1 is Cl or F, or R 1 but one or more R 6 Me optionally substituted with; R2 is hydrogen, CH2c-Pr, or Me; R 3 is Me; R 4 is hydrogen, cyano, halogen, nitro, or C1-C3 alkyl, and alkyl is one or more R 6 optionally substituted with; or R 4 But NR 7 R 8 , N.R. 8 C(O)R 7 , OR 7 , or S(O)pR 9 and; R 5 is hydrogen, cyano, Br, Cl, F, nitro, or C1-C3-alkyl; or R 5 But, OR 7 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , or NR 8 C(O)OR 7 and The compound of Formula 1 or Embodiment 1, wherein Q is Q-1, Q-2, Q, Q-13, Q-14, Q-19, or Q-24.

[0145] Embodiment A10. X is O; n is 1, 2, or 3; p is 0, 1, or 2; A is CR 1 and; R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 1 is a phenyl or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, and each phenyl or heteroaromatic ring is selected from one or more R 6 optionally substituted with R 1 C3-C9-trialkylsilyl, C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , OS(O)2R 9, or S(=NR 11 )O p R 9 or R 1 is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , or SO2NR 7 R 8 a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 2 but one or more R 6 and substituted with phenyl, or a 4-6 membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 2 nitrogen atoms, or a 5 membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6 membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or heterocyclic ring is optionally substituted with one or more R 6 optionally substituted with R 2 But C(O)R 7 , C(O)OR 7 , N.R. 7 R8 , OR 7 , S(O)pR 9 or SO2NR 7 R 8 and; R 3 is C1-C3 alkyl or C1-C3 haloalkyl; R 4 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , S(O)pR 9 , SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 and; R 5 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6-alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C.R. 7 (=NO)R 8 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R.8 C(O)R 7 , N.R. 8 C(O)OR 7 , N.R. 11 SO2NR 7 R 8 , OR 7 , S(O)pR 9 , or SO2NR 7 R 8 and; R 6 is halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , C(O)NR 7 R 8 , N.R. 7 R 8 , NR8C(O)R7, NR8C(O)OR7, OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 ,OC(O)OR 7 , S(O)pR 9 , SO2NR 7 R 8 , or S(=NR)O p R 7 and; R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl or cycloalkylalkyl is selected from the group consisting of one or more R 12 optionally substituted with R 7 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R12 optionally replaced by; R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, and each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from the group consisting of one or more R 6 optionally replaced by; When R7 and R8 are on N, R7 and R8 are oxygen, S(O)p or NR 7 can form a 3 to 7 carbon ring optionally containing: R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 9 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl; R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C(O)OR 7 , or S(O)pR 7 and; R12 is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C8 cycloalkylalkyl, each alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl optionally substituted with halogen or cyano; Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with 1 to 3 groups and the thiazole is optionally substituted with 1 to 2 groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R 6 , C(O)R 7 , C.R. 7 (=NOR 8 ), C(O)OR 7 , C(O)NR 7 R 8 , C(S)NR 7 R 8 , OR 7 , S(O) p R 9 , SO2NR 7 R 8 optionally substituted with NR 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , SO2NR 7 R 8or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, if a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , SO2NR 7 R 8 and a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with

[0146] Embodiment A11. X is O; n is 1, 2, or 3; p is 0, 1, or 2; A is CR 1 and; R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 1is a phenyl or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, and each phenyl or heteroaromatic ring is selected from one or more R 6 optionally substituted with R 1 C3-C9-trialkylsilyl, C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , OS(O)2R 9 , or S(=NR 11 )O p R 9 or R 1 is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , or SO2NR 7 R 8a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 2 but one or more R 6 and substituted with phenyl, or a 4-6 membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 2 nitrogen atoms, or a 5 membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6 membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or heterocyclic ring is optionally substituted with one or more R 6 optionally substituted with R 2 But C(O)R 7 , C(O)OR 7 , N.R. 7 R 8 , OR 7 , S(O)pR 9 or SO2NR 7 R 8 and; R 3 is C1-C3 alkyl; R 4 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R6 optionally substituted with; C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , S(O)pR 9 , SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 and; R 5 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6-alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C.R. 7 (=NO)R 8 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , N.R. 11 SO2NR 7 R 8 , OR 7 , S(O)pR 9 , or SO2NR 7 R 8 and; R 6is halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , C(O)NR 7 R 8 , N.R. 7 R 8 , NR8C(O)R7, NR8C(O)OR7, OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 ,OC(O)OR 7 , S(O)pR 9 , SO2NR 7 R 8 , or S(=NR)O p R 7 and; R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl or cycloalkylalkyl is selected from the group consisting of one or more R 12 optionally substituted with R 7 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 12 optionally replaced by; R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, and each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from the group consisting of one or more R 6 optionally replaced by; R 7 and R 8 If on N, then R 7 and R 8 is oxygen, S(O)p or NR 7 can form a 3 to 7 carbon ring optionally containing: R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 9 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl; R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C(O)OR 7 , or S(O)pR 7 and; R 12 is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 alkoxy, C2-C6 alkenyl, C4-C8 cycloalkylalkyl, each alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl optionally substituted with halogen or cyano; Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with 1 to 3 groups and the thiazole is optionally substituted with 1 to 2 groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R 6 , C(O)R 7 , C.R. 7 (=NOR 8 ), C(O)OR 7 , C(O)NR 7 R 8 , C(S)NR 7 R 8 , OR 7 , S(O) p R 9 , SO2NR 7 R 8 optionally substituted with NR 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , SO2NR 7 R 8 or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, if a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R8 , S(O)pR 7 , SO2NR 7 R 8 A compound of Formula 1 or embodiment A10, wherein the heterocyclic ring is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted by:

[0147] Embodiment A12. X is O; n is 1, 2, or 3; p is 0, 1, or 2; A is CR 1 and; R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 1 is a phenyl or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, and each phenyl or heteroaromatic ring is selected from one or more R 6 optionally substituted with R 1 C3-C9-trialkylsilyl, C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , OS(O)2R 9 , or S(=NR 11 )O p R 9 or R 1 is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , or SO2NR 7 R 8 a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 2 but one or more R 6and substituted with phenyl, or a 4-6 membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 2 nitrogen atoms, or a 5 membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6 membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or heterocyclic ring is optionally substituted with one or more R 6 optionally substituted with R 2 But C(O)R 7 , C(O)OR 7 , N.R. 7 R 8 , OR 7 , S(O)pR 9 or SO2NR 7 R 8 and; R 3 is C1-C3 alkyl; R 4 is hydrogen, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , S(O)pR 9 , SO2NR 7 R 8 , or NR 11 SO2NR7 R 8 and; R 5 is hydrogen, cyano, halogen, nitro, C1-C6-alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C.R. 7 (=NO)R 8 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , N.R. 11 SO2NR 7 R 8 , OR 7 , S(O)pR 9 , or SO2NR 7 R 8 and; R 6 is halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , C(O)NR 7 R 8 , N.R. 7 R 8 , NR8C(O)R7, NR8C(O)OR7, OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 ,OC(O)OR 7 , S(O)pR 9 , SO2NR 7 R 8 and; R 7is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl or cycloalkylalkyl is selected from the group consisting of one or more R 12 optionally substituted with R 7 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 12 optionally replaced by; R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, and each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from the group consisting of one or more R 6 optionally replaced by; When R7 and R8 are on N, R7 and R8 are oxygen, S(O)p or NR 7 can form a 3 to 7 carbon ring optionally containing: R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 9 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 10is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl; R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C(O)OR 7 , or S(O)pR 7 and; R 12 is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, each alkyl optionally substituted with halogen or cyano; Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with 1 to 3 groups and the thiazole is optionally substituted with 1 to 2 groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R 6 , C(O)R 7 , C.R. 7 (=NOR 8 ), C(O)OR 7 , C(O)NR 7 R 8 , C(S)NR 7 R 8 , OR 7 , S(O) p R 9 , SO2NR 7 R 8 optionally substituted with NR 7 R 8 , N.R. 8 C(O)R 7, N.R. 8 C(O)OR 7 , S(O)pR 7 , SO2NR 7 R 8 or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, if a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , SO2NR 7 R 8 A compound of Formula 1 or embodiment A10, wherein the heterocyclic ring is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted by:

[0148] Embodiment A13. X is O; n is 1, 2, or 3; p is 0, 1, or 2; A is CR 1 and; R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R1 is a phenyl or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, and each phenyl or heteroaromatic ring is selected from one or more R 6 optionally substituted with R 1 C3-C9-trialkylsilyl, C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , OS(O)2R 9 , or S(=NR 11 )O p R 9 or R 1 is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , or SO2NR 7 R 8a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 2 but one or more R 6 and substituted with phenyl, or a 4-6 membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 2 nitrogen atoms, or a 5 membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6 membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or heterocyclic ring is optionally substituted with one or more R 6 optionally substituted with R 2 But C(O)R 7 , C(O)OR 7 , N.R. 7 R 8 , OR 7 , S(O)pR 9 or SO2NR 7 R 8 and; R 3 is C1-C3 alkyl; R 4 is hydrogen, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6optionally replaced by; R 5 is hydrogen, cyano, halogen, nitro, C1-C6-alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 5 But C(O)R 7 , C.R. 7 (=NO)R 8 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , S(O)pR 9 , or SO2NR 7 R 8 and; R 6 is halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 ,OC(O)OR 7 , S(O)pR 9 , SO2NR 7 R 8 and; R 7is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 7 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, and each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from the group consisting of one or more R 6 optionally replaced by; R 7 and R 8 If on N, then R 7 and R 8 is oxygen, S(O)p or NR 7 can form a 3 to 7 carbon ring optionally containing: R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 9 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl; R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C(O)OR 7 , or S(O)pR 7 and; Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with 1 to 3 groups and the thiazole is optionally substituted with 1 to 2 groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R 6 , C(O)R 7 , C.R. 7 (=NOR 8 ), C(O)OR 7 , C(O)NR 7 R 8 , C(S)NR 7 R 8 , OR 7 , S(O) p R 9 , SO2NR 7 R 8 optionally substituted with NR 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , SO2NR 7 R 8or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, if a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , SO2NR 7 R 8 A compound of Formula 1 or embodiment A10, wherein the heterocyclic ring is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted by:

[0149] Embodiment A14. X is O; n is 1, 2, or 3; p is 0, 1, or 2; A is CR 1 and; R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 1is a phenyl or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, and each phenyl or heteroaromatic ring is selected from one or more R 6 optionally substituted with R 1 C3-C9-trialkylsilyl, C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , OS(O)2R 9 , or S(=NR 11 )O p R 9 or R 1 is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , or SO2NR 7 R 8a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 2 but one or more R 6 and substituted with phenyl, or a 4-6 membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 2 nitrogen atoms, or a 5 membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6 membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or heterocyclic ring is optionally substituted with one or more R 6 optionally substituted with R 2 But C(O)R 7 , C(O)OR 7 , N.R. 7 R 8 , OR 7 , S(O)pR 9 or SO2NR 7 R 8 and; R 3 is C1-C3 alkyl; R 4 is hydrogen, cyano, halogen, nitro, C1-C6 alkyl, and each alkyl is selected from one or more R 6 optionally replaced by; R 5is hydrogen, cyano, halogen, nitro, C1-C6-alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 5 But NR 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , S(O)pR 9 , or SO2NR 7 R 8 and; R 6 is halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 ,OC(O)OR 7 , S(O)pR 9 , or SO2NR 7 R 8 and; R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 7 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, and each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from the group consisting of one or more R 6 optionally replaced by; R 7 and R 8 If on N, then R 7 and R 8 is oxygen, S(O)p or NR 7 can form a 3 to 7 carbon ring optionally containing: R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 9 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl; R 11is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C(O)OR 7 , or S(O)pR 7 and; Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with 1 to 3 groups and the thiazole is optionally substituted with 1 to 2 groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R 6 , C(O)R 7 , C.R. 7 (=NOR 8 ), C(O)OR 7 , C(O)NR 7 R 8 , C(S)NR 7 R 8 , OR 7 , S(O) p R 9 , SO2NR 7 R 8 optionally substituted with NR 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , SO2NR 7 R 8or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, if a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , SO2NR 7 R 8 A compound of Formula 1 or embodiment A10, wherein the heterocyclic ring is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted by:

[0150] Embodiment A15. X is O; n is 1, 2, or 3; p is 0, 1, or 2; A is CR 1 and; R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 1is a phenyl or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, and each phenyl or heteroaromatic ring is selected from one or more R 6 optionally substituted with R 1 C3-C9-trialkylsilyl, C(O)R 7 , C.R. 7 (=NO)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 , OC(O)NR 7 R 8 ,OC(O)OR 7 , S(O)pR 9 , SF5, SO2NR 7 R 8 , OS(O)2R 9 , or S(=NR 11 )O p R 9 or R 1 is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , or SO2NR 7 R 8a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 2 but one or more R 6 C1-C6 alkyl optionally substituted with; R 3 is Me; R 4 is hydrogen, cyano, halogen, nitro, C1-C3 alkyl, and each alkyl is selected from one or more R 6 optionally replaced by; R 5 is hydrogen, cyano, halogen, or nitro; or R 5 But NR 7 R 8 , N.R. 8 C(O)R 7 , OR 7 , S(O)pR 9 , or SO2NR 7 R 8 and; R 6 is halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 ,OC(O)OR 7 , S(O)pR 9 , SO2NR 7 R 8 and; R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 7 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, and each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from the group consisting of one or more R 6 optionally replaced by; R 7 and R 8 If on N, then R 7 and R8 is oxygen, S(O)p or NR 7 can form a 3 to 7 carbon ring optionally containing: R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 9is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl; R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C(O)OR 7 , or S(O)pR 7 and; Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with 1 to 3 groups and the thiazole is optionally substituted with 1 to 2 groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R 6 , C(O)R 7 , C.R. 7 (=NOR 8 ), C(O)OR 7 , C(O)NR 7 R 8 , C(S)NR 7 R 8 , OR 7 , S(O) p R 9 , SO2NR 7 R 8optionally substituted with NR 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , S(O)pR 7 , SO2NR 7 R 8 or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, if a nitrogen atom is present, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , S(O)pR 7 , SO2NR 7 R 8 A compound of Formula 1 or embodiment A10, wherein the heterocyclic ring is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted by:

[0151] Embodiment A16. X is O; n is 1 or 2; p is 0, 1, or 2; A is CR 1 and; R 1 is a halogen; or R 1 is a C1-C6 alkyl, and each alkyl is selected from one or more R 6 optionally replaced by; R 2is hydrogen or C1-C6 alkyl; R 3 is Me; R 4 is cyano or nitro; R 5 is hydrogen, cyano, halogen, or nitro; or R 5 But NR 7 R 8 , N.R. 8 C(O)R 7 , OR 7 , S(O)pR 9 , or SO2NR 7 R 8 and; R 6 is halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , C(O)NR 7 R 8 , N.R. 7 R 8 , N.R. 8 C(O)R 7 , N.R. 8 C(O)OR 7 , OR 7 , NHC(O)NR 7 R 8 , N.R. 7 S(O)pR 9 ,OC(O)R 7 ,OC(O)OR 7 , S(O)pR 9 , SO2NR 7 R 8 and; R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 7is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, and each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from the group consisting of one or more R 6 optionally replaced by; R 7 and R 8 If on N, then R 7 and R8 is oxygen, S(O)p or NR 7 can form a 3 to 7 carbon ring optionally containing: R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from the group consisting of one or more R 6 optionally substituted with R 9 is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R 6 optionally replaced by; R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl; R 11is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, and each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from the group consisting of one or more R 6 optionally substituted with; C(O)R 7 , C(O)OR 7 , or S(O)pR 7 A compound according to Formula 1 or embodiment A10, wherein:

[0152] Embodiment A17. X is O or S; A is N or CR 1 and; R 1 is Cl, F, or Br, or R 1 but one or more R 6 Me optionally substituted with R 1 However, OMe, SF3, or OS(O)2R 9 and; R 2 is hydrogen, C1-C4 alkyl, or C4-C6 cycloalkylalkyl, and each alkyl or cycloalkylalkyl is selected from one R 6 optionally substituted with R 2 But C(O)R 7 or C(O)OR 7 and; R 3 is Me; and R 4 is hydrogen, cyano, halogen, nitro, or C1-C3 alkyl, and alkyl is one or more R 6 A compound of Formula 1 or embodiment A10, optionally substituted with:

[0153] Embodiment A18. X is O or S; A is N or CR 1 and; R 1 is Cl, F, or Br, or R 1but one or more R 6 Me optionally substituted with R 1 However, OMe, SF3, or OS(O)2R 9 and; R 2 is hydrogen, C1-C4 alkyl, or C4-C6 cycloalkylalkyl, and each alkyl or cycloalkylalkyl is selected from one R 6 optionally substituted with R 2 But C(O)R 7 or C(O)OR 7 and; R 3 is Me; R 4 is hydrogen, cyano, halogen, nitro, or C1-C3 alkyl, and alkyl is one or more R 6 optionally substituted with; and A compound according to formula 1 or embodiment A10, wherein Q is Q-1, Q-2, Q-6, Q-7, Q-11, Q-13, Q-14, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, or Q-25.

[0154] Certain embodiments include compounds of Formula 1 selected from the group consisting of those as displayed in Table A.

[0155] [Table 1]

[0156] [Table 2]

[0157] [Table 3]

[0158] Embodiment Y1. A composition comprising a compound of Formula 1 or any one of the preceding embodiments and at least one additional ingredient selected from the group consisting of surfactants, solid diluents, and liquid diluents, the composition optionally further comprising at least one additional biologically active compound or agent.Embodiment Y2. The at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, afidopiropen, amidoflumet, amitraz, avermectin, azadirachtin, azinphos-methyl, bendiocarb, benfuracarb, bensultap, bifenthrin, bifenazate, bistrifluron, borate, bromantraniliprole, buprofezin, carbaryl, carbofuran, cartap, chloran Traniliprole, chlorfenapyr, chlorfluazuron, chlorprallethrin, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezine, clothianidin, cyantraniliprole, cyclaniliprole, cyclobutrifluram, cycloprothrin, cycloxapride, cyetopyrafen, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalodiamide, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, Alpha-cypermethrin, Zeta-cypermethrin, Cyprofuranilide, Cyromazine, Deltamethrin, Diafenthiuron, Diazinon, Dichlorantraniliprole, Dieldrin, Diflobidazine, Diflubenzuron, Dimefluthrin, Dimehypo, Dimethoate, Dinotefuran, Diofenolan, Emamectin, Endosulfan, Esfenvalerate, Ethiprole, Etofenprox, Etoxazole, Fenazaquin, Fenbutatin Oxide, Fenitrothion phenmezodithiaz, fenothiocarb, fenoxycarb, fenpyroximate, fenpropathrin, fenvalerate, fipronil, flometoquin, flonicamid, fluacrypyrim, fluazaindolizine, flubendiamide, fluchlordiniliprole, flucythrinate, flufenerim, flufenoxuron, flufenoxystrobin, fluensulfone, fluhexafon, flupentiofenox, fluopyram, flupirimine, flupyradifurone,Fluvalinate, tau-fluvalinate, fluxamethamide, fonofos, formetanate, fosthiazate, halofenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, hydroprene, imidacloprid, indazapiroxameth (N-(1-methylcyclopropyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide), indoxacarb, insecticidal soap, isofenphos, isocycloceram, kappa-tefluthrin, kinoprene, lufenuron, malathion, mepafluthrin, metaflumizone, me aldehyde, methamidophos, methidathion, methiocarb, methomyl, methoprene, methoxychlor, methoxyfenozide, metofluthrin, monocrotophos, monofluorothrin, nicofluprole, nicotine, N-[1,1-dimethyl-2-(methylthio)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1,1-dimethyl-2-(methylsulfinyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1,1-dimethyl-2-(methylsulfinyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1,1-dimethyl-2-(methyl sulfonyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-(1-methylcyclopropyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1-(difluoromethyl)cyclopropyl]-2-(3-pyridinyl)-2H-indazole-4-carboxamide, nitenpyram, nithiazine, novaluron, noviflumuron, oxamyl, oxazosulfil, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pyrimica Rub, profenofos, profluthrin, propargite, protrifenbut, piflubumid, pymetrozine, pyrafluprole, pyrethrins (pyrethrum), pyridaben, pyridalyl, pyrifluquinazone, pyrimidifen, pyriminostrobin, pyriprole, pyriproxyfen, rotenone, ryanodine, silafluofen, spidoxamat, spinetoram, spinosad, spirobudifen, spirodiclofen, spiromesifen, spirotetramat, sulprofos, sulfoxaflor, tebufenozide, tebufenpyrad,The composition of embodiment Y1, wherein the active ingredient is selected from the group consisting of teflubenzuron, tefluthrin, kappa-tefluthrin, terbufos, tetrachlorantraniliprole, tetrachlorvinphos, tetramethrin, tetramethylfluthrin, tetraniliprole, thiacloprid, thiamethoxam, thiodicarb, thiosultap, thiosultap sodium, thiolantraniliprole, thioxazaphen, tolfenpyrad, tralomethrin, triazamate, trichlorfon, trifluenfuronate, triflumezopyrim, triflumuron, cyclopyrazoflor, Bacillus sphaericus, Bacillus thuringiensis delta-endotoxin, entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi, plant essences including synthetic extracts and unrefined oils, RNA interference-mediated target inhibitors.

[0159] Embodiment Y3. The embodiment Y3 wherein the at least one additional biologically active compound or agent is abamectin, acetamiprid, acrinathrin, afidopiropen, amitraz, avermectin, azadirachtin, benfuracarb, bensultap, bifenthrin, buprofezin, carbaryl, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalo Torin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenitrothion, fenothiocarb, fenoxycarb, fenvalerate, fipronil, flometoquin, flonicamid, flubendiamide, flufenol Xuron, Flufenoxystrobin, Fluensulfone, Flupiprole, Flupyradifurone, Fluvalinate, Formetanate, Fosthiazate, Heptafluthrin, Hexaflumuron, Hydramethylnon, Imidacloprid, Indoxacarb, Lufenuron, Meperfluthrin, Metaflumizone, Methiocarb, Methomyl, Methoprene, Methoxyfenozide, Metofluthrin, Monofluorothrin, Nitenpyram, Nithiazine, Novaluron, Oxamyl, Piflubumid, Pymetro The composition of embodiment Y2, wherein the antibacterial agent is selected from the group consisting of: benzophenone-4, benzocaine, pyrethrins, pyridaben, pyridalyl, pyriminostrobin, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulfoxaflor, tebufenozide, tetramethrin, tetramethylfluthrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, triflumezopyrim, triflumuron, Bacillus thuringiensis deltaendotoxin, all strains of Bacillus thuringiensis, and all strains of nuclear polyhedrosis virus.

[0160] Embodiment Y4. The composition of any one of Embodiments Y1-Y3, further comprising a liquid fertilizer.

[0161] Embodiment Y5. The composition of embodiment Y4, wherein the liquid fertilizer is aqueous.

[0162] Embodiment Y6. A soil drench formulation comprising the composition of any one of embodiments Y1 to Y3.Embodiment Y7. A spray composition comprising the composition of any one of embodiments Y1 to Y3 and a propellant.

[0163] Embodiment Y8. A bait composition comprising the composition of any one of embodiments Y1-Y3, one or more food ingredients, optionally an attractant, and optionally a wetting agent.

[0164] Embodiment Y9. A trapping device for controlling and eliminating invertebrate pests, comprising: a bait composition according to embodiment Y8; and a housing configured to contain the bait composition, wherein the housing has at least one opening sized to allow passage of invertebrate pests, thereby allowing the invertebrate pests to access the bait composition from a location external to the housing; and wherein the housing is further configured to be placed at or near a location of possible or known activity for the invertebrate pests.

[0165] Embodiment Y10. A composition comprising the composition of any of embodiments Y1-Y3, wherein the composition is a solid composition selected from dusts, powders, granules, pellets, prills, pastilles, tablets, and filled films.

[0166] Embodiment Y11. The composition of embodiment Y10, wherein the composition is water-dispersible or water-soluble.

[0167] Embodiment Y12. A liquid or dry formulation comprising the composition of any one of embodiments Y1-Y3 for use in drip irrigation systems, in-furrow at planting, with a handheld sprayer, backpack sprayer, boom sprayer, ground sprayer, aerial application, unmanned aerial vehicle, or seed treatment.

[0168] Embodiment Y13. A liquid or dry formulation according to embodiment Y12, wherein the formulation is sprayed in minute amounts.

[0169] Of note, the compounds of the present invention are characterized by favorable metabolism and / or soil persistence patterns and exhibit activity in controlling and combating a variety of agronomic and non-agronomic invertebrate pests.

[0170] Of particular note is the protection of agricultural crops from damage or injury caused by invertebrate pests by controlling and eradicating them, due to their spectrum of invertebrate pest control and economic importance. The compounds of the invention also protect leaves or other plant parts that are not in direct contact with the compound of Formula 1 or a composition comprising this compound, due to their favorable translocation or systemic properties in plants.

[0171] Bioaccumulation of pesticides in non-target organisms is an important safety consideration, and it is often desirable to limit systemic exposure and / or accumulation of the pesticide and / or its metabolites in non-target organisms. For example, when a compound is applied to crop plants as an insecticide, it is desirable that the compound not accumulate in the plasma or fat of vertebrates.

[0172] The compound of formula 1 can exhibit favorable pharmacokinetic properties in vertebrates.In particular, it has been found that the compound of formula 1 has rapid clearance from the plasma / blood of vertebrates and low distribution in the fat of vertebrates, thus reducing the possibility of undesirable bioaccumulation.Notably, the fluorine atom at the 4-position of the phenyl ring is bonded to the 5-position of the isoxazoline ring.

[0173] The pharmacokinetic properties of the compound of Formula 1 can be measured using a variety of assay protocols known in the science of pharmacology. In one exemplary method involving a single oral dose, three male and three female rats each receive a single dose of the test substance via oral gavage. Blood is collected via the tail vein at 0.25, 0.5, 1, 2, 4, 8, 12, and 24 hours, and then every 24 hours until sacrifice. To process the sample into plasma, blood is collected into tubes containing ethylenediaminetetraacetic acid (EDTA) and centrifuged at approximately 3000 rpm to separate the plasma from red blood cells. Alternatively, blood is collected using microcapillary tubes and aliquoted into tubes containing HPLC water (1:1, v / v). Fat is also collected, homogenized, and extracted to determine the concentration of the compound of Formula 1 at the time of sacrifice. Plasma or blood and fat are analyzed for the compound of Formula 1 and / or metabolites, e.g., by high performance liquid chromatography (HPLC) with tandem mass spectrometry detection (LC / MS / MS), to determine the concentration of the test substance. Plasma or blood pharmacokinetic data are analyzed using nonlinear modeling software (e.g., Phoenix® WinNonlin®, Pharsight-A Certara™ Company, St. Louis, MO, USA) to determine the plasma / blood half-life of the compound of Formula 1, the time after administration to reach maximum plasma / blood concentration (T max ), maximum plasma / blood concentration (C max ), and the area under the plasma / blood concentration curve (AUC) are determined. Because fat analysis requires the sacrifice of the rats, fat data are obtained at a single time point (i.e., the time of rat sacrifice). The fat:plasma or fat:blood ratio of the compound of Formula 1 is then determined.

[0174] Also of note as an embodiment of the present invention is a composition comprising a compound according to any of the preceding embodiments, as well as any other embodiment described herein, and any combination thereof, and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, optionally further comprising at least one additional biologically active compound or agent.

[0175] Also noteworthy as an embodiment of the present invention is a composition for controlling and combating invertebrate pests, comprising a compound according to any of the preceding embodiments, as well as any other embodiment described herein, and any combination thereof, and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, optionally further comprising at least one additional biologically active compound or agent. Embodiments of the present invention further include methods for controlling and combating invertebrate pests, comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound according to any of the preceding embodiments (e.g., as a composition described herein).

[0176] Embodiments of the present invention also include compositions comprising a compound according to any of the preceding embodiments in the form of a liquid soil drench formulation.Embodiments of the present invention further include a method for controlling and eradicating invertebrate pests, comprising contacting soil with a biologically effective amount of a liquid composition as a soil drench comprising a compound according to any of the preceding embodiments.

[0177]

[0010] Embodiments of the present invention also include a spray composition for controlling and eradicating invertebrate pests, the spray composition comprising a biologically effective amount of a compound described in any of the preceding embodiments and a propellant.

[0011] Embodiments of the present invention further include a bait composition for controlling and eradicating invertebrate pests, the bait composition comprising a biologically effective amount of a compound described in any of the preceding embodiments, one or more food materials, optionally an attractant, and optionally a wetting agent.

[0012] Embodiments of the present invention also include a device for controlling and eradicating invertebrate pests, the device comprising the bait composition and a housing configured to contain the bait composition, wherein the housing has at least one opening sized to allow invertebrate pests to pass through, thereby allowing invertebrate pests to access the bait composition from a location external to the housing, and the housing is further configured to be placed at or near a location of possible or known invertebrate pest activity.

[0178] Embodiments of the present invention also include a method for protecting seeds from invertebrate pests, comprising contacting seeds with a biologically effective amount of a compound according to any of the preceding embodiments.

[0179] Embodiments of the present invention also include methods for controlling and eradicating invertebrate pests, comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula 1 (e.g., as a composition described herein), with the proviso that the method is not a method of medical treatment of the human body by therapy.

[0180] The present invention also relates to such methods, wherein an invertebrate pest or its environment is contacted with a composition comprising a biologically effective amount of a compound of Formula 1 and at least one additional ingredient selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, optionally further comprising a biologically effective amount of at least one additional bioactive compound or agent, with the proviso that the method is not a method of medical treatment of the human body by therapy.

[0181] Compounds of Formula 1 can be prepared by one or more of the following methods and variations described in Schemes 1-13. The definitions of the substituents in the compounds of Formulas 1-14 below are as defined above in the Summary of the Invention unless otherwise specified. The following abbreviations can be used: DMF is N,N-dimethylformamide, and DBU is 1,8-diazabicyclo[5.4.0]undec-7-ene. Compounds of Formula 1 where X is S can be prepared by treating compounds of Formula 1 where X is O with a sulfurizing agent such as phosphorus pentasulfide or Lawesson's reagent (2,4-di(p-methoxyphenyl)-1,3-dithiadiphosphetanesulfide) using conditions and procedures well known to those skilled in the art of organic synthesis.

[0182] As shown in Scheme 1, compounds of formula 1 where X is O can be prepared by reaction of an amine intermediate of formula 2 with a carboxylic acid or acid derivative of formula 3 using an amide coupling agent and conditions well known to those skilled in the art. For example, 3 where Y is chloride or fluoride is combined with 2, optionally in the presence of sodium bicarbonate, potassium hydroxide, or an amine such as triethylamine, diisopropylethylamine, or pyridine, in a solvent or mixture of solvents, typically dichloromethane, ethyl acetate, tetrahydrofuran, or toluene, at a temperature from subambient to the boiling point of the reaction mixture. Intermediate 3, where Y is hydroxyl, can be reacted in the presence of an activating agent such as dicyclohexylcarbodiimide, 1,1′-carbonyldiimidazole, or (1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) under conditions well known in the art. Intermediate 3, where Y is alkoxy, typically methoxy or ethoxy, can be reacted in a solvent such as toluene or dichloromethane with promotion by a trialkylaluminum reagent, such as trimethylaluminum, to prepare compounds of formula 1. Compounds of formula 3 are commercially available or can be prepared by procedures well known to those skilled in the art. [ka]

[0183] As shown in Scheme 2, intermediate 2 can be prepared by reductive amination of a ketone of formula 4. Such a reaction is well known in the art and involves the reaction of ketone 4 with an amine R in a solvent such as methanol, ethanol, or water, often with the addition of an acid promoter such as acetic acid. 2 The reaction consists of a combination of NH2 and a reducing agent, such as sodium cyanoborohydride or sodium triacetoxyborohydride. The conversion of 4 to 2 can be improved by the addition of an optional dehydrating agent, such as titanium ethoxide or titanium isopropoxide, to form an intermediate imine that is reduced under conditions well known in the art by the subsequent addition of a reducing agent, such as sodium borohydride, or by exposure to hydrogen in the presence of a catalyst, such as palladium on carbon. The use of titanium tetraalkoxides and reducing agents allows the formation of R 2 is S(O)pR 7 or SO2NR 7 R 8 and triethylsilane in combination with the catalyst bismuth trichloride as described in Tetrahedron Letters 2014, 55(10), 1829-1834, or triethylsilane and the catalyst dirhenium heptoxide as described in Chemical Communications 2012, 48(66), 8276-8278, can be useful for preparing compounds of formula 1, where R 2 C(O)OR 7 may be useful for preparing compounds of formula 1, [ka]

[0184] R 2A variation of the approach of Scheme 2 to obtain compounds of Formula 2 where is hydrogen is shown in Scheme 3. Combination of ketone 4 with 2-methyl-2-propanesulfinamide, available as either the (R) or (S) enantiomer, under dehydrating conditions using a titanium tetraalkoxide such as titanium tetraethoxide, followed by reduction with a reagent such as sodium borohydride, followed by removal of the sulfinyl group by exposure to an acid such as hydrochloric acid, typically in aqueous methanol, 1,4-dioxane, or tetrahydrofuran, provides amine 2 in predominantly one enantiomer. A single enantiomer of a compound of Formula 1 may offer advantages in activity, safety, and / or physical or other properties. [ka]

[0185] As shown in Scheme 4, compounds of Formula 4 can be prepared by metallation of compounds of Formula 5 and contact with a carbonyl-containing partner. Such metallation can be facilitated by reaction with a strong lithium base, such as lithium diisopropylamide or lithium tetramethylpiperidide, or a magnesium base, such as isopropylmagnesium chloride, optionally in complex with lithium chloride and / or other metal salts. Suitable solvents are ethers, such as diethyl ether or tetrahydrofuran, optionally in the presence of a cosolvent, such as N,N'-dimethylpropyleneurea (DMPU). The reaction can be carried out at temperatures below -70°C to ambient or slightly elevated temperatures. A suitable carbonyl compound is, for example, the "Weinreb amide" R3C(O)N(Me)OMe, which directly affords ketone 4 upon hydrolytic workup. [ka]

[0186] Optionally, the carbonyl compound in combination with the metallated pyrazole 5 can be converted to an aldehyde R as shown in Scheme 5. 3CHO, resulting in intermediate alcohol 6. These alcohols can then be oxidized to provide ketones 4, such as by contact with chromium trioxide, manganese dioxide, or 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin periodinane, Martin's reagent) in solvents such as dichloromethane, acetonitrile, or acetone, or under many other reaction conditions and methods well known to those skilled in the art. [ka]

[0187] Alternatively, as shown in Scheme 6, alcohols of formula 6 can be converted to azides 7, such as by reaction of 6 with diphenylphosphoryl azide under Mitsunobu conditions by adding an azodicarboxylate ester, such as azodicarboxylic acid diethyl ester (DEAD), and triphenylphosphine, typically in tetrahydrofuran solvent at slightly below ambient temperature, to afford R 2 can be used to prepare amines of formula 2, where is hydrogen. Azide 7 can then be reduced to amine 2 using reagents such as triphenylphosphine in aqueous tetrahydrofuran, stannous chloride in methanol or ethanol, or by hydrogenation over a palladium catalyst in solvents such as methanol, ethanol, or ethyl acetate. [ka]

[0188] As shown in Scheme 7, R 2 Amines of formula 2 where R is hydrogen can be converted to R(O) by using reductive amination conditions similar to those in Scheme 2 and well known in the art. 7 , C(O)OR 7 , N.R. 7 R 8 , OR 7 , S(O)pR 7 or SO2NR 7 R8 Other than R 2 can be used to prepare other amines of formula 2 [ka]

[0189] As shown in Scheme 8, pyrazoles of formula 5 can be prepared by reacting a pyrazole of formula 8 with a group QL (where L is a halogen, an alkyl- or haloalkylsulfonate, a nitro group, or an alkylsulfonyl group), optionally in the presence of a base promoter, and optionally with a metal catalyst. Possible optional bases include triethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), potassium carbonate, cesium carbonate, sodium hydride, or potassium tert-butoxide. The optional metal catalyst is typically copper or palladium, generally with an attached ligand such as N,N'-dimethylethylenediamine, 1,2-cyclohexanediamine, or 2,2'-bipyridine for copper-promoted reactions, or an arylphosphine, alkylphosphine, or mixed alkyl / arylphosphine ligand for palladium-promoted reactions. Typical solvents for these reactions include water, methanol, tert-butanol, tetrahydrofuran, dimethylsulfoxide, dimethylformamide, 1,4-dioxane, and toluene. Such reactions are well known to those skilled in the art. [ka]

[0190] Pyrazoles of formula 8 and groups QL are either commercially available or readily prepared by methods known to those skilled in the art. Alternatively, as shown in Scheme 9, compounds of formula 1 can be prepared by combining a pyrazole of formula 9 with a compound of formula QL under conditions such as those described for Scheme 8 above. [ka]

[0191] Compounds of formula 9 can be prepared by methods similar to those in Schemes 1-8, either directly, as shown in Scheme 10 for pyrazoles of formula 10, or, in some cases advantageously, by use of a protecting group on the pyrazole. Some examples of suitable protecting groups are benzyl or para-methoxybenzyl. These protecting groups are removed by methods well known in the art, such as hydrogenation to remove the benzyl group, or treatment with a mild oxidizing agent, such as ceric ammonium nitrate, or an acid, such as trifluoroacetic acid, to remove the para-methoxybenzyl or related group. [ka]

[0192] As shown in Scheme 11, R 2 is hydrogen, the compound of formula 1 is 2 -L, where L is a suitable leaving group such as a halogen, methanesulfonate, or para-toluenesulfonate, can be converted to other compounds of formula 1. These reactions are generally carried out in solvents such as tetrahydrofuran, dimethylsulfoxide, or dimethylformamide in the presence of a base promoter such as sodium hydride, potassium tert-butoxide, or potassium bis(trimethylsilyl)amide. [ka]

[0193] Optionally, pyrazoles of formula 4 can be prepared as shown in Schemes 12 and 13. As shown in Scheme 12, hydrazones of formula 12 can be prepared by the reaction of glyoxal with a substituted hydrazine in water or acetic acid as a solvent, as described in Blake, James F.; et al., World Intellectual Property Organization, WO 2007103308. Typically, these reactions are carried out at room temperature to 125°C, and water can be removed by forming an azeotrope or by distillation to obtain hydrazones of formula 12. Hydrazines of formula 14 are commercially available or readily prepared by methods known to those skilled in the art. Hydrazones of formula 12 can be cyclized to pyrazoles of formula 4 through condensation with compounds of formula 11, where X is a halogen, under basic conditions, as described in Taniguchi, Takahiko; et al., World Intellectual Property Organization, WO 2012020780. Typically, these reactions are carried out in a solvent such as 1,4-dioxane at temperatures from room temperature to 150° C. Unsubstituted pyrazoles can be converted to R under numerous other reaction conditions and methods well known to those skilled in the art. 4 or R 5 can be further derivatized to a variety of compounds where is a substituent such as bromine or cyano. [ka] [ka]

[0194] Those skilled in the art of organic synthesis will recognize R 1 , R 2 , R 4 , R 5It will be recognized that many substituents such as and substituents on Q can be interconverted by known chemistry of functional group transformations by reaction with suitable reagents and therefore will not be described in detail herein due to their familiarity. However, as a general example, some such transformations can be the replacement of a hydrogen atom with a halogen using electrophilic halogenating reagents such as N-chlorosuccinimide, 1,3-dibromo-5,5-dimethylhydantoin, and N-fluorobenzenesulfonimide under neutral conditions, or after using a base such as lithium diisopropylamide to remove the hydrogen atom from the substrate. Halogens are highly competent functional groups for the introduction of many other substituents, or for the introduction of cyano-, carbonyl-, amine-, or sulfur-based groups, for example, by radical reactions or nucleophilic substitution, typically with palladium, nickel, or copper catalysis. Other groups can be interconverted by reduction with a variety of well-known reagents, such as lithium tetrahydroaluminate, or by palladium-catalyzed hydrogenation; oxidation with well-known reagents, such as manganese dioxide, chromium trioxide, or Dess-Martin periodinane; dealkylation of alkoxy groups by contact with boron tribromide or aluminum trichloride; alkylation of oxygen-, nitrogen-, and sulfur-based groups with a variety of reagents; nitration of aromatic and heteroaromatic rings; acylation of amines; sulfonylation of amine and hydroxy groups; or preparation of amides from carboxylic acids or esters. Many of these interconversions are illustrated by the steps in the examples below.

[0195] Examples of intermediates useful in the preparation of compounds of the invention are shown in Tables I-1 to I-53. The following abbreviations are used in the tables below: Me means methyl, Et means ethyl, Ph means phenyl, C(O) means carbonyl, and CHO means formyl. Table I-1 [ka] Q is Q-1

[0196] [Table 4]

[0197] [Table 5] Table I-2 is identical to Table I-1 except for Q-2. Table I-3 is identical to Table I-1 except for Q-3. Table I-4 is identical to Table I-1 except for Q-4. Table I-5 is identical to Table I-1 except that it is Q-5. Table I-6 is identical to Table I-1 except that it is Q-6. Table I-7 is identical to Table I-1 except for Q-7. Table I-8 is identical to Table I-1 except that it is Q-8. Table I-9 is identical to Table I-1 except that it is Q-9. Table I-10 is identical to Table I-1 except that it is Q-10. Table I-11 is identical to Table I-1 except that it is Q-11. Table I-12 is identical to Table I-1 except that it is Q-12. Table I-13 is identical to Table I-1 except that it is Q-13. Table I-14 is identical to Table I-1 except that it is Q-14. Table I-15 is identical to Table I-1 except that it is Q-15. Table I-16 is identical to Table I-1 except that it is Q-16. Table I-17 is identical to Table I-1 except that it is Q-17. Table I-18 is identical to Table I-1 except that it is Q-18. Table I-19 is identical to Table I-1 except that it is Q-19. Table I-20 is identical to Table I-1 except that it is Q-20. Table I-21 is identical to Table I-1 except that it is Q-21. Table I-22 is identical to Table I-1 except that it is Q-22. Table I-23 is identical to Table I-1 except that it is Q-23. Table I-24 is identical to Table I-1 except that it is Q-24. Table I-25 is identical to Table I-1 except that it is Q-25. Table I-26 is identical to Table I-1 except that it is Q-26.

[0198] Table I-27 [ka] Table I-27 is identical to Table I-1 except that the structure under the heading "Table I-1" is replaced by the structure shown above. Tables I-28 through I-53 are identical to Tables I-2 through I-26 except that the structure under the heading "Table I-1" is replaced by the structure shown under "Table I-27."

[0199] It is recognized that some of the reagents and reaction conditions described above for preparing compounds of Formula 1 may be incompatible with certain functional groups present in those intermediates. In these cases, incorporating a protection / deprotection sequence into the synthesis or functional group interconversion will aid in obtaining the desired reaction product. The use and selection of protecting groups will be apparent to those familiar with chemical synthesis (see, for example, Greene, TW; Wuts, PGM, Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). Those skilled in the art will recognize that in some cases, after the introduction of the reagents shown in the individual schemes, additional routine synthetic steps not described in detail may be required to complete the synthesis of compounds of Formula 1. Those skilled in the art will also recognize that it may be necessary to combine and perform the steps described in the above schemes in an order other than the specific order presented to prepare compounds of Formula 1.

[0200] Those skilled in the art will further recognize that the compounds of Formula 1 and intermediates described herein can also be subjected to a variety of electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

[0201] Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. Accordingly, the following synthetic examples are to be construed as merely illustrative and are not intended to limit the present disclosure in any way. The steps in the following synthetic examples describe the procedure for each step in the overall synthetic transformation, and the starting material for each step does not necessarily have to be prepared by the specific preparative procedure whose procedure is described in another example or step. Percentages are by weight, except in the case of chromatographic solvent mixtures or unless otherwise indicated. Parts and percentages relating to chromatographic solvent mixtures are by volume unless otherwise specified. 1 H NMR spectra are reported in ppm downfield from tetramethylsilane, where "s" means singlet, "d" means doublet, "t" means triplet, "q" means quartet, "m" means multiplet, "dd" means doublet of doublets, "dt" means doublet of triplets, and "brs" means broad singlet. DMF means N,N-dimethylformamide, and DMSO means dimethyl sulfoxide. Compound numbers refer to Index Table A. [Example]

[0202] Synthesis Example 1 Preparation of N-[1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (compound 9) Step A: Preparation of 5-bromo-2-(3-nitropyrazol-1-yl)pyridine In a microwave vial, 3-nitro-1H-pyrazole (2.00 g, 17.7 mmol, 1 equiv.) and 2,5-dibromopyridine (4.10 g, 17.7 mmol, 1 equiv.) were combined in N,N-dimethylformamide (15 mL), and cesium carbonate (5.7 g, 17.7 mmol, 1 equiv.) was added. The reaction mixture was irradiated in a microwave at 140 °C for 2 h and monitored by thin-layer chromatography. Once the starting material was consumed, the reaction mixture was poured into cold water (100 mL), and the resulting solid was collected on a frit and washed with water. Drying under reduced pressure afforded 5-bromo-2-(3-nitropyrazol-1-yl)pyridine (3.5 g, 74%) as an off-white solid melting at 215–218 °C. 1 H NMR(DMSO-d6)δ 8.84(d,1H),8.73(m,1H),8.35(m,1H),7.96(m,1H),7.35(d,1H). LCMS: m / z: 269 / 271 [M+H]+

[0203] Step B: Preparation of 1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl]ethanone A mixture of 5-bromo-2-(3-nitropyrazol-1-yl)pyridine (5.5 g, 20.522 mmol, 1 equiv.) prepared as in Step 1 in tetrahydrofuran (350 mL) was cooled to -30 °C, and lithium diisopropylamide (2 M solution in tetrahydrofuran, 15.4 mL, 30.8 mmol, 1.5 equiv.) was added dropwise, and the mixture was stirred at -30 °C. After 40 min, N-methoxy-N-methyl-acetamide (3.1 g, 30.8 mmol, 1.5 equiv.) was added, and the reaction mixture was allowed to warm slowly to ambient temperature over 2 h. Saturated aqueous ammonium chloride solution (100 mL) was added, and the mixture was extracted with two 200 mL portions of ethyl acetate. The combined organic phases were washed with two 100 mL portions of saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure to give a residue. The residue was subjected to Combiflash chromatography eluting with a 0–50% gradient of ethyl acetate in petroleum ether to give 1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl]ethanone (2.3 g, 36%) as a yellow solid melting at 117–120 °C. 1 H NMR(CDCl3)δ 8.52(m,1H),8.07(m,1H),7.70(m,1H),7.09(m,1H),2.57(s,3H).LCMS:m / z:311 / 313 [M+H]+

[0204] Step C: Preparation of 1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl]-N-methyl-ethanamine To a mixture of 1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl]ethanone (2.8 g, 9.0 mmol, 1 equiv.) prepared as in Step 2 and titanium tetraethoxide (2.6 g, 11.7 mmol, 1.3 equiv.) in methanol (77 mL) was added methylamine (30% solution in ethanol, 2.8 mL, 27 mmol, 3 equiv.). The reaction mixture was stirred at ambient temperature for 16 hours and then heated at 60°C for 2 hours. The reaction mixture was cooled to 0°C, and sodium borohydride (0.341 g, 9.03 mmol, 1.0 equiv.) was added. The reaction mixture was stirred at ambient temperature for 2 hours, then poured into ice-cold water (200 mL) and extracted with two 150 mL portions of ethyl acetate. The combined organic phases were washed twice with 100 mL portions of saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure to give crude 1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl]-N-methyl-ethanamine (1.8 g, 62%) as an impure brown semi-solid melting at 125-128 °C. LCMS: m / z: 326 / 328 [M+H] + as one component. Used directly in the following reaction in Step 4.

[0205] Step D: Preparation of N-[1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide To a mixture of 1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl]-N-methyl-ethanamine (1.8 g, 5.5 mmol, 1 equiv.) prepared as in Step 3 and 3,5-bis(trifluoromethyl)benzoic acid (1.70 g, 6.65 mmol, 1.2 equiv.) in N,N-dimethylformamide (18 mL) was added 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU, 3.15 g, 8.31 mmol, 1.5 equiv.) and diisopropylethylamine (2.0 mL, 11 mmol, 2 equiv.). The reaction mixture was stirred at ambient temperature for 16 hours, poured into cold water (80 mL), and extracted with two 150 mL portions of ethyl acetate. The combined organic phases were washed twice with 100 mL portions of saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated under reduced pressure to give a crude residue. This residue was purified by Combiflash chromatography eluting with a gradient of 0 to 50% ethyl acetate in petroleum ether to give the compound of the present invention, N-[1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (1.8 g, 58%), as an off-white solid melting at 174-177 °C. A portion of the product from Step B coeluted with this product. 1 H NMR(CDCl3)δ 8.45(m,1H),8.1(m,1H),7.9(m,2H),7.4-7.5(m,2H),7.2(m,1H),6.5(q,1H),2.60(s,3H),1.74(d,3H). LCMS: m / z: 566 / 568 [M+H]+

[0206] Synthesis Example 2 Preparation of N-[1-[5-amino-2-(5-bromo-2-pyridyl)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (Compound 11) To a mixture of N-[1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (1.10 g, 1.95 mmol, 1 equiv.) prepared as in Example 1 in ethanol (50 mL) and water (25 mL) was added ammonium chloride (415 mg, 7.79 mmol, 4 equiv.) and iron powder (217 mg, 3.89 mmol, 2 equiv.). The reaction mixture was stirred at reflux for 4 hours and then allowed to cool to ambient temperature. The reaction mixture was diluted with ethyl acetate (100 mL), filtered through a pad of Celite filter aid, and the filter cake was washed with ethyl acetate (100 mL). The combined organic layers were washed twice with 100 mL portions of saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure to provide a crude residue. The crude material was purified by Combiflash chromatography eluting with a gradient of 0-80% ethyl acetate / petroleum ether to give the product of this invention, N-[1-[5-amino-2-(5-bromo-2-pyridyl)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (800 mg, 80%) as a brown solid melting at 139-141 °C. 1 H NMR(DMSO-d6,90℃)δ 7.8-8.25(m,3H),7.4-7.85(m,3H),6.30(q,1H),5.97(s,1H),5.29(s,2H),3.32(s,3H),2.50(d,3H). LCMS: m / z: 536 / 538 [M+H]+

[0207] Synthesis Example 3 Preparation of N-[1-[5-acetamido-2-(5-bromo-2-pyridyl)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (Compound 15): In a 20 mL scintillation vial, a mixture of N-{1-[5-amino-2-(5-bromopyridin-2-yl)pyrazol-3-yl]ethyl}-N-methyl-3,5-bis(trifluoromethyl)benzamide (96.7 mg, 0.18 mmol, 1 equiv.) prepared as in Example 2 in tetrahydrofuran (0.60 mL) was stirred and cooled in an ice bath. Triethylamine (0.077 mL, 0.541 mmol, 3 equiv.) and acetyl chloride (0.016 mL, 0.22 mmol, 1.2 equiv.) were added dropwise. The mixture was stirred at ambient temperature for 16 hours, diluted with water, and extracted twice with two approximately 10 mL portions of ethyl acetate. The organic phase was washed with saturated aqueous sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure to a crude residue. The crude residue was subjected to automated flash chromatography eluting with a gradient of 0 to 50% ethyl acetate in hexane to isolate the compound of the present invention, N-[1-[5-acetamido-2-(5-bromo-2-pyridyl)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (84 mg), as a brown solid. 1 H NMR(CDCl3)δ 8.35(m,1H),8.20(m,1H),7.85-7.96(m,2H),7.63(m,1H),7.45(br s,2H),7.11(m,1H),6.50(br m,1H),2.53(s,3H),2.20(s,3H),1.67(d,3H). LCMS: m / z: 578 / 580 [M+H]+

[0208] Synthesis Example 4 Preparation of N-[1-[5-amino-2-(5-bromo-2-pyridyl)-4-iodo-pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (compound 10) To a mixture of N-{1-[5-amino-2-(5-bromopyridin-2-yl)pyrazol-3-yl]ethyl}-N-methyl-3,5-bis(trifluoromethyl)benzamide (800 mg, 1.5 mmol, 1 equiv.), prepared as in Example 2, in N,N-dimethylformamide (8 mL) was added N-iodosuccinimide (415 mg, 1.64 mmol, 1.1 equiv.). The reaction mixture was stirred at 40° C. for 3 hours and then poured into cold water (100 mL). The resulting solid was collected on a frit, washed with water, and dried under reduced pressure to give the compound of the present invention, N-[1-[5-amino-2-(5-bromo-2-pyridyl)-4-iodo-pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (780 mg, 78%) as an off-white solid melting at 159-162°C. 1 H NMR(DMSO-d6,91℃)δ 8.33(s,1H),8.05(m,1H),7.96(m,1H),7.69(s,2H),7.48(m,1H),6.17(q,1H),4.84(br,2H),2.96(s,3H),1.72(s,3H). LCMS: m / z: 662 / 664 [M+H]+

[0209] Synthesis Example 5 Preparation of N-[1-[3-amino-4-cyano-1-(5-cyano-2-pyridinyl)-1H-pyrazol-5-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (Compound 14) A mixture of N-[1-[5-amino-2-(5-bromo-2-pyridyl)-4-iodo-pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (400 mg, 0.605 mmol, 1 equiv.) prepared as in Example 4 and zinc cyanide (283 mg, 2.42 mmol, 4 equiv.) in N,N-dimethylformamide (4 mL) was degassed with argon in a microwave vial for 15 minutes, followed by the addition of 1,1′-bis(diphenylphosphino)ferrocene (67 mg, 0.12 mmol, 0.2 equiv.) and tris(dibenzylideneacetone)dipalladium(0) (55 mg, 0.060 mmol, 0.1 equiv.). The reaction mixture was irradiated in a microwave at 120°C for 1.5 hours, then poured into ice-cold water (20 mL) and extracted with two 50 mL portions of ethyl acetate. The combined organic layers were washed twice with 50 mL portions of saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated under reduced pressure to give a crude residue. The crude material was purified by Combiflash chromatography eluting with a gradient of 0-80% ethyl acetate / petroleum ether to give the compound of the present invention, N-[1-[5-amino-4-cyano-2-(5-cyano-2-pyridyl)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (220 mg, 71%) as an off-white solid melting at 191-194°C. IR 2222 cm -1 1 H NMR(DMSO-d6,89℃)δ 8.76(s,1H),8.38(m,1H),8.06(s,1H),7.8-7.9(m,3H),6.35(q,1H),5.84(s,2H),2.96(s,3H),2.48(d,3H). LCMS: m / z: 508 [M+H]+

[0210] Synthetic Examples 6 and 7 Preparation of N-[1-[4-cyano-1-(5-cyano-2-pyridinyl)-3-(methylamino)-1H-pyrazol-5-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (Compound 12) and N-[1-[4-cyano-2-(5-cyano-2-pyridyl)-5-(dimethylamino)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (Compound 13) To a mixture of N-[1-[5-amino-4-cyano-2-(5-cyano-2-pyridyl)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (80 mg, 0.16 mmol, 1 equiv.) prepared as in Example 5 and potassium carbonate (43 mg, 0.32 mmol, 2 equiv.) in N,N-dimethylformamide (2 mL) in a microwave vial, iodomethane (33 mg, 0.23 mmol, 1.5 equiv.) was added. The reaction mixture was irradiated in a microwave at 100° C. for 1 hour, poured into ice-cold water (20 mL), and extracted with two 50 mL portions of ethyl acetate. The combined organic layer was washed twice with 50 mL portions of saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure to give a crude residue. The crude material was purified by Combiflash chromatography eluting with a gradient of 0-80% ethyl acetate / petroleum ether to afford the compound of the present invention, N-[1-[4-cyano-2-(5-cyano-2-pyridyl)-5-(methylamino)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (Compound 12) (20 mg, 24%) as a light brown solid (Compound 12). 1 H NMR(CDCl3)δ 8.6(br,1H),8.07(br,2H),7.82-7.95(br m,3H),6.6(br,1H),4.22(q,1H),3.1(s,3H),3.02(d,3H),1.83(d,3H). LCMS: m / z: 522 [M+H]+ Also isolated from this reaction was the compound of the present invention, N-[1-[4-cyano-2-(5-cyano-2-pyridyl)-5-(dimethylamino)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (Compound 13) (15 mg, 17%), as an off-white solid (Compound 13). 1 H NMR(CDCl3)δ 8.62(br,1H),8.07(br,2H),7.85-7.95(br,3H),6.58(br,1H),3.16(s,3H),3.12(s,6H),1.85(d,3H).LCMS:m / z:536 [M+H]+

[0211] Synthesis Example 8 Preparation of methyl 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl]pyridine-3-carboxylate (Compound 30): In a steel bomb, a mixture of N-[1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (500 mg, 0.884 mmol, 1 equiv.) prepared as in Example 1 and triethylamine (0.255 mL, 1.76 mmol, 2 equiv.) in N,N-dimethylformamide (2 mL) and methanol (10 mL) was degassed with argon for 15 minutes. [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1:1 complex with dichloromethane) (72 mg, 0.088 mmol, 0.1 equiv.) was added. Carbon monoxide gas was admitted at 150 psi, and the mixture was heated at 100 °C for 16 h. The reaction mixture was poured into cold water (80 mL) and extracted with two 150 mL portions of ethyl acetate. The combined organic phases were washed with two 100 mL portions of saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure to give a residue. The crude residue was purified by Combiflash chromatography eluting with a gradient of 0-80% ethyl acetate in petroleum ether to give the compound of the present invention, methyl 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl]pyridine-3-carboxylate (300 mg, 65%) as a brown solid melting at 171-174 °C. 1 H NMR(DMSO-d6,90℃)δ 8.55(br,1H),8.29(d,1H),8.00(s,1H),7.75(d,1H),7.61(s,2H),6.3(b r,1H),6.05(s,1H),5.12(s,2H),3.83(s,3H),2.65(br,3H),1.57(d,3H). LCMS: m / z: 516 [M+H]+

[0212] Synthesis Example 9 Preparation of methyl 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-iodo-pyrazol-1-yl]pyridine-3-carboxylate (Compound 23): To a mixture of methyl 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl]pyridine-3-carboxylate (1.5 g, 2.9 mmol, 1 equiv.) prepared as in Example 8 in N,N-dimethylformamide (20 mL) was added N-iodosuccinimide (0.72 g, 3.2 mmol, 1.1 equiv.), and the reaction mixture was stirred at 40° C. for 3 hours and then poured into cold water (200 mL). The resulting solid was collected on a frit, washed with water, and dried under reduced pressure to give the compound of the present invention, methyl 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-iodo-pyrazol-1-yl]pyridine-3-carboxylate (1.43 g, 72%) as a white solid melting at 163-169 °C. 1 H NMR (DMSO-d6,89℃)δ 8.71(s,1H),8.30(m,1H),7.94(s,1H),7.67(m 3H),6.35(q,1H),4.99(s,2H),3.87(s,3H),2.98(s,3H),1.75(d,3H). LCMS: m / z: 642 [M+H]+

[0213] Synthesis Example 10 Preparation of methyl 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-cyano-pyrazol-1-yl]pyridine-3-carboxylate (compound 24): Methyl 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-iodo-pyrazol-1-yl]pyridine-3-carboxylate (1.0 g, 1.56 mmol, 1 equiv.) prepared as in Example 9 and zinc cyanide (0.365 g, 3.12 mmol, 2 equiv.) in N,N-dimethylformamide (15 mL) were degassed with argon in a microwave vial for 15 minutes, followed by the addition of 1,1′-bis(diphenylphosphino)ferrocene (0.172 g, 0.312 mmol, 0.2 equiv.) and tris(dibenzylideneacetone)dipalladium(0) (0.142 g, 0.156 mmol, 0.1 equiv.). The reaction mixture was irradiated in a microwave at 120°C for 1.5 hours, then poured into ice-cold water (80 mL) and extracted with two 100 mL portions of ethyl acetate. The combined organic phases were washed with two 50 mL portions of saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure to give a residue. The crude residue was purified by Combiflash chromatography eluting with a gradient of 0-50% ethyl acetate / petroleum ether to give the compound of the present invention, methyl 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-cyano-pyrazol-1-yl]pyridine-3-carboxylate (700 mg, 82%), as an off-white solid melting at 229-233°C. 1 H NMR(DMSO-d6,89℃)δ 8.79(s,1H),8.42(d,1H),8.03(s,1H),7.77-7.85(m,3H),6.38(q,1H),5.74(s,2H),4.02(s,3H),2.92(s,3H),1.73(d,3H). LCMS: m / z: 541 [M+H]+

[0214] Synthesis Example 11 Preparation of 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-cyano-pyrazol-1-yl]pyridine-3-carboxylic acid (compound 25): To a mixture of methyl 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-cyano-pyrazol-1-yl]pyridine-3-carboxylate (800 mg, 1.48 mmol, 1 equiv.), prepared as in Example 4, in tetrahydrofuran (40 mL) and water (20 mL) was added lithium hydroxide monohydrate (124 mg, 2.96 mmol, 2 equiv.). The reaction mixture was stirred at ambient temperature for 16 hours, poured into cold water (20 mL), and extracted with two 50 mL portions of diethyl ether. The aqueous layer was acidified to pH 4 with 1 N aqueous hydrochloric acid and the resulting precipitate was collected on a frit, washed with water and dried under reduced pressure to give the compound of the present invention, 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-cyano-pyrazol-1-yl]pyridine-3-carboxylic acid (650 mg, 83%) as an off-white solid melting at 193-196 °C. 1 H NMR (DMSO-d6,90℃)δ 8.74(s,1H),8.34(m,1H),8.02(s,1H),7.83(s,2H),7.64(m,1H),6.31(q,1H),5.63(s.2H),2.91(s,3H),1.69(d,3H). LCMS: m / z: 527 [M+H]+

[0215] Synthesis Example 12 Preparation of N-[1-[3-amino-4-cyano-1-[5-(4-morpholinylcarbonyl)-2-pyridinyl]-1H-pyrazol-5-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (compound 26): To a mixture of 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-cyano-pyrazol-1-yl]pyridine-3-carboxylic acid (700 mg, 1.33 mmol, 1 equiv.) prepared as in Example 5, morpholine (115 mg, 1.73 mmol, 1.3 equiv.), and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU, 758 mg, 2.0 mmol, 1.5 equiv.) in N,N-dimethylformamide (15 mL) was added diisopropylethylamine (0.73 mL, 4.0 mmol, 3 equiv.). The reaction mixture was stirred at ambient temperature for 16 hours and poured into cold water (60 mL). The resulting solid was collected on a frit, washed with water, and dried under reduced pressure to give the compound of the present invention, N-[1-[5-amino-4-cyano-2-[5-(morpholine-4-carbonyl)-2-pyridyl]pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (500 mg, 63%), as a white solid melting at 211-214°C. 1 H NMR(DMSO-d6,89℃)δ 8.39(s,1H),8.06(m,1H),8.01(m,1H),7.89(s,2H),7.76(m,1H),6.35( q,1H),5.66(s.2H),3.58(m,4H),3.48(m,4H),2.93(s,3H),1.70(d,3H). LCMS: m / z: 596 [M+H]+

[0216] Synthesis Example 13 Preparation of methyl 6-[3-acetamido-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl]pyridine-3-carboxylate (compound 27): To a mixture of methyl 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl]pyridine-3-carboxylate (300 mg, 0.58 mmol, 1 equiv.) prepared as in Example 8 and triethylamine (0.167 mL, 1.17 mmol, 2 equiv.) in dichloromethane (10 mL), acetyl chloride (0.061 mL, 0.87 mmol, 1.5 equiv.) was added with ice-bath cooling. The reaction mixture was stirred at ambient temperature for 16 hours, then combined with ice-cold water (20 mL) and extracted with two 50 mL portions of dichloromethane. The combined organic layers were washed twice with 50 mL portions of saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure to give a crude residue. The crude material was purified by Combiflash chromatography eluting with a gradient of 0-70% ethyl acetate / petroleum ether to give the compound of the present invention, methyl 6-[3-acetamido-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl]pyridine-3-carboxylate (150 mg, 46%), as a white solid melting at 266-269 °C. 1 H NMR(DMSO-d6,89℃)δ 10.44(s,1H),8.64(br,1H),8.41(d,1H),7.99(m,1H),7.82(d,1H),7.57(s,2H),6.99(s,1H),6.35(br m,1H),3.86(s,3H),2.55-2.85(br,3H),2.06(s,3H),1.62(d,3H). LCMS: m / z: 558 [M+H]+

[0217] Synthesis Example 14 Preparation of 6-[3-acetamido-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl]pyridine-3-carboxylic acid (compound 28): To a mixture of methyl 6-[3-acetamido-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl]pyridine-3-carboxylate (120 mg, 0.215 mmol, 1 equiv.), prepared as in Example 13, in tetrahydrofuran (10 mL) and water (5 mL) was added lithium hydroxide monohydrate (27 mg, 0.65 mmol, 3 equiv.). The reaction mixture was stirred at ambient temperature for 16 hours, poured into cold water (15 mL), and extracted with two 20 mL portions of diethyl ether. The aqueous layer was acidified to pH 4 with 1 N aqueous hydrochloric acid, and the resulting solid was collected on a frit, washed with water, and dried under reduced pressure to give the compound of the present invention, 6-[3-acetamido-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl]pyridine-3-carboxylic acid (100 mg, 86%), as an off-white solid melting at 266-269 °C. 1 H NMR(DMSO-d6,28℃)δ 13.4(br,1H),10.83(s,1H),8.71(s,1H),8.48(d,1H),8.15(s,1H),7.84(d,1H) ,7.41(s,2H),7.05(s,1H),6.44(m,1H),2.39(s,3H),2.07(s,3H),1.60(d,3H). LCMS: m / z: 544 [M+H]+

[0218] Synthesis Example 15 Preparation of N-[1-[5-acetamido-2-[5-(morpholine-4-carbonyl)-2-pyridyl]pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (compound 21) To a mixture of 6-[3-acetamido-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl]pyridine-3-carboxylic acid (100 mg, 0.183 mmol, 1 equiv.) prepared as in Example 14, morpholine (20 mg, 0.24 mmol, 1.3 equiv.), and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU, 104 mg, 0.275 mmol, 1.5 equiv.) in N,N-dimethylformamide (3 mL) was added diisopropylethylamine (0.10 mL, 0.55 mmol, 3 equiv.). The reaction mixture was stirred at ambient temperature for 16 hours and poured into cold water (20 mL). The resulting solid was collected on a frit, washed with water, and dried under reduced pressure to give the compound of the present invention, N-[1-[5-acetamido-2-[5-(morpholine-4-carbonyl)-2-pyridyl]pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (103 mg, 46%) as a white solid melting at 276-279 °C. 1 H NMR(DMSO-d6,90℃)δ 10.36(s,1H),8.24(br s,1H),8.02(s,1H),8.00(d,1H),7.75(d,1H),7.69(s,2H),6.95(s,1H),6.32(b r,1H),3.55(br,4H),3.44(br,4H),2.6-2.8(br,3H),2.06(s,3H),1.60(d,3H). LCMS: m / z: 613 [M+H]+

[0219] Synthesis Example 16 Preparation of N-[1-[4-cyano-2-(2-pyridyl)pyrazol-3-yl]ethyl]-N-(cyclopropylmethyl)-3,5-bis(trifluoromethyl)benzamide (compound 7): Step A: Preparation of (2E)-2-(2-pyridylhydrazono)acetaldehyde A solution of 2-pyridylhydrazine (5.0 g, 45.45 mmol, 1.0 equiv.) in water (5 mL) was added with stirring to 40% glyoxal (6.5 mL, 181.8 mmol, 4.0 equiv.) at ambient temperature. The reaction mixture was heated at 100° C. for 4 hours and then cooled to ambient temperature. The precipitated solid was collected on a frit and dried under vacuum to give (2E)-2-(2-pyridylhydrazono)acetaldehyde (5.8 g, 85%) as a gray solid. 1 H NMR(DMSO)δ 12.058(bs,NH),9.509(d,1H),8.253(d,1H),7.804(m,1H),7.510(d,1H),7.357(d,1H),7.025(t,1H).

[0220] Step B: Preparation of 1-[2-(2-pyridyl)pyrazol-3-yl]ethanone To a mixture of (2E)-2-(2-pyridylhydrazono)acetaldehyde (5.8 g, 38.9 mmol, 1.0 equiv.) in 1,4-dioxane (50 mL) was added potassium carbonate (13.4 g, 97.3 mmol, 2.5 equiv.) and chloroacetone (4.88 mL, 58.3 mmol, 1.5 equiv.) at ambient temperature. The reaction mixture was heated at 80° C. for 5 hours, concentrated under reduced pressure, diluted with water (100 mL), and extracted twice with two 150 mL portions of ethyl acetate. The combined organic layer was washed with saturated aqueous sodium chloride (50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting crude solid was purified by column chromatography on silica gel (40 g) using Combiflash eluting with 40% ethyl acetate / petroleum ether to give 1-[2-(2-pyridyl)pyrazol-3-yl]ethanone (5.1 g, 70%) as an off-white solid. 1 H NMR(DMSO-d6)δ 8.46(d,1H),8.05(d,1H),7.84(s,1H),7.68(d,1H),7.48(d,1H),7.14(d,1H),2.49(s,3H)

[0221] Step C: Preparation of 1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]ethanone To a solution of 1-[2-(2-pyridyl)pyrazol-3-yl]ethanone (2.00 g, 10.6 mmol, 1.0 equiv.) in dry N,N-dimethylformamide (20 mL) was added N-bromosuccinimide (2.00 g, 11.7 mmol, 1.1 equiv.) at 0° C. The resulting reaction mixture was stirred from 0° C. to ambient temperature for 16 hours, quenched with water (50 mL), and extracted with two 100 mL portions of ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude residue. The crude material was purified by column chromatography on silica gel (24 g) eluting with 20% ethyl acetate / petroleum ether to give 1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]ethanone (1.8 g, 64%) as an off-white solid. 1 H NMR(DMSO-d6)δ 8.44(d,1H),8.08(m,2H),7.87(d,1H),7.46(t,1H),2.48(s,3H)

[0222] Step D: Preparation of N-[1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]ethyl]-1-cyclopropyl-methanimine To a solution of 1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]ethanone (1.0 g, 3.7 mmol, 1.0 equiv.) in dry tetrahydrofuran (20 mL) was added titanium tetraethoxide (3.4 g, 15.0 mmol, 4.0 equiv.) and cyclopropylmethylamine (236 mg, 4.15 mmol, 1.1 equiv.) at ambient temperature. The resulting reaction mixture was heated at 70° C. for 16 hours, water (50 mL) and ethyl acetate (200 mL) were added, and the mixture was filtered through a Celite® pad. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude residue. The crude material was purified by column chromatography on silica gel (24 g) eluting with 50% ethyl acetate / petroleum ether to give 1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]-N-(cyclopropylmethyl)ethanimine (0.6 g, 55%) as a brown solid. 1H NMR(DMSO-d6)δ 8.41(d,1H),8.03(m,2H),7.90(d,1H),7.40(t,1H),2.88(m,1H),2.67( m,1H),2.50(s,3H),1.18(m,1H),0.86(m,1H),0.29(m,2H),-0.14(m,1H)

[0223] Step E: Preparation of 1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]-N-(cyclopropylmethyl)ethanamine To a solution of 1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]-N-(cyclopropylmethyl)ethanimine (100 mg, 0.31 mmol, 1.0 equiv) in methanol (5 mL) was added cerium(III) chloride (115 mg, 0.466 mmol, 1.5 equiv) with stirring at 0° C. After 15 min, sodium borohydride (29 mg, 0.77 mmol, 2.5 equiv) was added in small portions at 0° C., and the mixture was stirred for 16 h. The reaction mixture was poured into ice-cold water (50 mL) and ethyl acetate (200 mL) and filtered through a pad of Celite®. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give crude 1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]-N-(cyclopropylmethyl)ethanamine (155 mg), which was used directly in the next step without further purification.

[0224] Step F: Preparation of N-[1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]ethyl]-N-(cyclopropylmethyl)-3,5-bis(trifluoromethyl)benzamide To a solution of 3,5-bis(trifluoromethyl)benzoic acid (600 mg, 2.3 mmol, 1.0 equiv.) in dry DMF (140 mL) was added 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU, 1.32 g, 3.4 mmol, 1.5 equiv.), crude 1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]-N-(cyclopropylmethyl)ethanamine (821 mg, 2.5 mmol, 1.1 equiv.) obtained in Step E, and diisopropylethylamine (1 mL, 5.8 mmol, 2.5 equiv.) at ambient temperature. The resulting reaction mixture was stirred at ambient temperature for 16 h, and 150 mL of water was added. The mixture was extracted twice with 200 mL portions of ethyl acetate, and the combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude residue. The crude material was purified by column chromatography on silica gel (40 g) using Combiflash eluting with 20% ethyl acetate / petroleum ether to give N-[1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]ethyl]-N-(cyclopropylmethyl)-3,5-bis(trifluoromethyl)benzamide (620 mg, 48%) as an off-white solid. NMR(DMSO-d6)δ8.39(s,1H),8.12(s,1H),8.03(s,1H),7.86(m,1H),7.60(s,2H) ,7.45(m,2H),6.28(m,1H),3.06(m,2H),1.86(d,3H),0.66(m,3H),0.35(m,2H).

[0225] Step G: Preparation of N-[1-[4-cyano-2-(2-pyridyl)pyrazol-3-yl]ethyl]-N-(cyclopropylmethyl)-3,5-bis(trifluoromethyl)benzamide To a solution of N-[1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]ethyl]-N-(cyclopropylmethyl)-3,5-bis(trifluoromethyl)benzamide (300 mg, 0.53 mmol, 1.0 equiv.) in dry N,N-dimethylformamide (3 mL) in a sealed tube at ambient temperature was added copper(I) cyanide (71 mg, 0.8 mmol, 1.5 equiv.). The resulting reaction mixture was stirred at 160° C. for 24 hours. Water (50 mL) was added, and the mixture was extracted with two 200 mL portions of ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to provide a crude residue. The crude material was purified by preparative high performance liquid chromatography to give N-[1-[4-cyano-2-(2-pyridyl)pyrazol-3-yl]ethyl]-N-(cyclopropylmethyl)-3,5-bis(trifluoromethyl)benzamide (113 mg, 41%) as an off-white solid. 1 H NMR(DMSO-d6)δ 8.49(s,1H),8.37(s,1H),8.18(m,1H),8.12(m,1H),7.82(s,1H),7.68(s,2H), 7.56(m,1H),6.26(m,1H),2.96(m,2H),1.90(d,3H),1.23(m,3H),0.34(m,2H).

[0226] Synthesis Example 17 Preparation of N-[1-(4-cyano-5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide (compound 82) Step A: Preparation of 2-(3-methoxypyrazol-1-yl)pyrimidine A mixture of cesium carbonate (30.2 g, 92.7 mmol, 1.2 equiv.), 3-methoxy-1H-pyrazole (7.58 g, 77.3 mmol, 1 equiv.), 2-chloropyrimidine (8.85 g, 77.3 mmol, 1 equiv.), and N,N-dimethylformamide (155 mL) was heated to 120 °C and stirred for 16 h. The reaction was cooled to room temperature and diluted with water (150 mL). Toluene (150 mL) was added, and the mixture was concentrated under reduced pressure on a rotary evaporator. This procedure was repeated, and the remaining aqueous phase was then extracted twice with ethyl acetate (2 × 150 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure onto Celite. The residue was purified by Combiflash chromatography eluting with a gradient of 50-70% ethyl acetate in hexane to give the desired product, 2-(3-methoxypyrazol-1-yl)pyrimidine (9.5 g, 70%). 1 H NMR(500MHz,chloroform-d)δ ppm 4.08(s,3H)5.97(d,J=2.90Hz,1H)7.08(t,J=4.81Hz,1H)8.42(d,J=2.90Hz,1H)8.68(d,J=4.88Hz,2H).LCMS:m / z:177 [M+H]+

[0227] Step B: Preparation of 2-(5-iodo-3-methoxy-pyrazol-1-yl)pyrimidine To a solution of 2-(3-methoxypyrazol-1-yl)pyrimidine (7.5 g, 42.6 mmol, 1 equiv.) in tetrahydrofuran (113 mL) (T<0°C), 2,2,6,6-tetramethylpiperidinylzinc chloride lithium chloride complex, a 17 w / v% solution in tetrahydrofuran (13.6 g, 79.9 mL, 17 w / v%, 47.9 mmol, 1.125 equiv.) was added dropwise by maintaining the temperature at T<5°C. The reaction mixture was allowed to warm to room temperature and stirred for 6 hours. Iodine (13.56 g, 53.43 mmol, 1.255 equiv.) was then added at room temperature, and the reaction was stirred at room temperature for 16 hours. Upon completion of the reaction, the reaction was cooled to 0°C, diluted with saturated aqueous ammonium chloride solution (200 mL), and extracted three times with ethyl acetate (3 x 200 mL). The combined organic layers were washed with saturated aqueous sodium bisulfite (200 mL) and saturated aqueous sodium chloride (100 mL). The organic layers were dried over magnesium sulfate, filtered, and concentrated onto Celite under reduced pressure. The residue was purified by Combiflash chromatography, eluting with a gradient of 60 to 100% ethyl acetate in hexanes, to give the desired product, 2-(5-iodo-3-methoxy-pyrazol-1-yl)pyrimidine (11.98 g, 93%). 1 H NMR(500MHz,chloroform-d)δ ppm 4.06(s,3H)6.28(s,1H)7.25(t,J=1.00Hz,1H)8.81(d,J=4.88Hz,2H).LCMS:m / z:303 [M+H] +

[0228] Step C: Preparation of 1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethanone A flask containing 2-(5-iodo-3-methoxypyrazol-1-yl)pyrimidine (7.3 g, 24.2 mmol, 1 equiv.) was evacuated and refilled with nitrogen twice, followed by the addition of anhydrous toluene (28 mL) via syringe. The solution was degassed with nitrogen for 8–10 minutes and then charged with tributyl(1-ethoxyvinyl)stannane (9.601 g, 8.981 mL, 1.069 g / mL, 26.6 mmol, 1.1 equiv.) and bis(triphenylphosphine)palladium(II) dichloride (1.696 g, 2.42 mmol, 0.1 equiv.). The reaction was refluxed at 92–95 °C for 16 hours. The reaction was cooled to room temperature and charged with 2 M aqueous hydrogen chloride (36 mL) and stirred for 2 hours. The reaction was diluted with ethyl acetate (200 mL) and water (200 mL). After separation of the layers, the organic layer was collected. The aqueous layer was extracted three times with ethyl acetate (3 × 100 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (100 mL), dried over magnesium sulfate, filtered, and concentrated onto Celite. The residue was purified by Combiflash chromatography eluting with a gradient of 40 to 70% ethyl acetate in hexane to give the desired product, 1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethanone (1.62 g, 31%). 1 H NMR(500MHz,chloroform-d)δ ppm 2.52(s,3H)4.07(s,3H)6.20(s,1H)7.21(t,J=4.88Hz,1H)8.73(d,J=4.88Hz,2H).LCMS:m / z:219 [M+H] +

[0229] Step D: Preparation of N-[1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethylidene]-2-methyl-propane-2-sulfinamide A mixture of 1-[5-methoxy-2-(pyrimidin-2-yl)pyrazol-3-yl]ethanone (1.88 g, 8.62 mmol, 1 equiv.) and tert-butanesulfinamide (1.149 g, 9.48 mmol, 1.1 equiv.) in anhydrous toluene (51 mL) was degassed with nitrogen for 5 minutes. To this solution was added titanium isopropoxide (4.897 g, 5.10 mL, 0.96 g / mL, 17.23 mmol, 2 equiv.) via syringe. The reaction mixture was refluxed at 105-110 °C for 16 hours, then cooled to room temperature and rapidly poured into stirring saturated aqueous sodium chloride solution (100 mL). The reaction mixture was diluted with ethyl acetate (100 mL) and stirred for 10 minutes. The mixture was then filtered through a pad of Celite, followed by washing the filter cake with ethyl acetate (50 mL). The layers were separated, the organic layer was collected, and the aqueous layer was extracted twice with ethyl acetate (2 x 50 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated onto Celite. The residue was purified by Combiflash chromatography, eluting with a gradient of 0 to 100% ethyl acetate in hexanes, to give the desired product, an E and Z mixture of N-[1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethylidene]-2-methyl-propane-2-sulfinamide (1.41 g, 51%). 1H NMR (500MHz, chloroform-d) δ ppm 1.19(s,27H)2.52(s,3H)2.63(s,6H)4.07(s,6H)4.08-4.09(m,3H)5.96- 6.04(m,1H)6.11(s,2H)7.08-7.14(m,1H)7.17(t,J=4.73Hz,2H)8.67(br d,J=4.12Hz,2H)8.72(d,J=4.73Hz,4H).LCMS:m / z:322 [M+H] +

[0230] Step E: Preparation of N-[1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-2-methyl-propane-2-sulfinamide To a solution of N-[1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethylidene]-2-methyl-propane-2-sulfinamide (1.21 g, 3.765 mmol, 1 equiv.) in methanol (75 mL) at 0° C. was added sodium borohydride (0.285 g, 7.53 mmol, 2 equiv.) in small portions. The reaction was allowed to warm to room temperature after gas evolution ceased and stirred for 2 h. The reaction was cooled to 0° C. and quenched with saturated ammonium chloride (100 mL). The solution was then concentrated under reduced pressure, and the residue was partitioned between water (100 mL) and ethyl acetate (100 mL). The organic layer was collected, and the aqueous layer was washed twice with ethyl acetate (2×100 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (50 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give the product, N-[1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-2-methyl-propane-2-sulfinamide (1.22 g). The product was used in the next step without further purification. LCMS: m / z: 324 [M+H] +

[0231] Step F: Preparation of 1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethylammonium chloride To a solution of N-[1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-2-methyl-propane-2-sulfinamide (128 mg, 0.396 mmol, 1 equiv.) prepared as in Step E in 1,4-dioxane (0.64 mL) at 0 °C, a solution of hydrogen chloride in dioxane (0.014 g, 0.099 mL, 4 M, 0.396 mmol, 1 equiv.) was added via syringe. The reaction mixture was stirred at room temperature for an additional 30 min. The solid was collected by filtration, washed with dioxane (2-3 mL), and dried under reduced pressure to give the product, 1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethylammonium chloride (0.07 g, 69%). 1H NMR(600MHz,DMSO-d6)δ ppm 1.60(d,J=6.90Hz,3H)3.90(s,3H)5.19(dt,J=12.03,6.06Hz,1H)6.39(s,1H)7.46(t,J=4.81Hz,1H)8.48(br s,3H)8.86(d,J=4.90Hz,2H).LCMS:m / z:220 [M+H] + (free amine).

[0232] Step G: Preparation of N-[1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide To a mixture of 1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethylammonium chloride (0.79 g, 3.089 mmol, 1 equiv.) and dichloromethane (25 mL) at 0 °C, 3,5-bis(trifluoromethyl)benzoyl chloride (1.28 g, 0.84 mL, 1.526 g / mL, 4.634 mmol, 1.5 equiv.) was added, followed by the dropwise addition of triethylamine (0.938 g, 1.292 mL, 0.726 g / mL, 9.2768 mmol, 3 equiv.). The reaction mixture was stirred at 0 °C for 10 minutes, then allowed to warm to room temperature and stirred for 16 hours. The reaction was quenched with saturated aqueous sodium bicarbonate (100 mL) and extracted three times with dichloromethane (3 × 100 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated onto Celite. The residue was purified by Combiflash chromatography eluting with a gradient of 20-60% ethyl acetate in hexane to give the desired product, N-[1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide (0.90 g, 63%), a compound of the present invention. 1H NMR(500MHz,chloroform-d)δ ppm 1.56(d,J=7.02Hz,3H)4.06(s,3H)5.98-6.06(m,1H)6.07(s,1H)7.24(t,J=1.00Hz,1H)8.01(s,1H)8.22(s,2H)8.46(br d,J=7.93Hz,1H)8.80(d,J=4.88Hz,2H).LCMS:m / z:460 [M+H] +

[0233] Step H: Preparation of N-[1-(4-iodo-5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide To a solution of N-[1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide (0.90 g, 1.96 mmol, 1 equiv.) in N,N-dimethylformamide (9 mL) was added N-iodosuccinimide (0.485 g, 2.16 mmol, 1.1 equiv.). The reaction mixture was heated to 80° C. and stirred for 3 hours. The reaction mixture was cooled to room temperature and partitioned between water (100 mL) and ethyl acetate (100 mL). The organic layer was collected, and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were washed with saturated aqueous sodium bisulfite (100 mL), dried over magnesium sulfate, filtered, and concentrated onto Celite. The residue was purified by Combiflash chromatography eluting with a gradient of 30-60% ethyl acetate in hexane to give the desired product, N-[1-(4-iodo-5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide (0.82 g, 72%), a compound of the present invention. 1 H NMR(500MHz,chloroform-d)δ ppm 1.51(d,J=7.32Hz,3H)4.11(s,3H)6.14-6.24(m,1H)7.34(t,J=1.00Hz,1H)8.01(s,1H)8.29(s,2H)8.86(d,J=4.73Hz,2H)9.26(br d,J=8.54Hz,1H).LCMS:m / z:586 [M+H] +

[0234] Step I: Preparation of N-[1-(4-cyano-5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide To a microwave vial equipped with a stir bar was added N-[1-(4-iodo-5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide (0.63 g, 1.08 mmol, 1 equiv.), zinc cyanide (0.506 g, 0.273 mL, 1.852 g / mL, 4.31 mmol, 4 equiv.), tris(dibenzylideneacetone)dipalladium(0) (0.099 g, 0.108 mmol, 0.1 equiv.), and 1,1′-ferrocenediyl-bis(diphenylphosphine) (0.119 g, 0.215 mmol, 0.2 equiv.) and anhydrous N,N-dimethylformamide (6.3 mL) under nitrogen. The reaction mixture was irradiated in a microwave at 120 °C for 30 min. The reaction mixture was cooled to room temperature and partitioned between water (25 mL) and ethyl acetate (25 mL). The organic layer was collected, and the aqueous layer was extracted with ethyl acetate (25 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated onto Celite. The residue was purified by Combiflash chromatography eluting with a gradient of 30 to 50% ethyl acetate in hexane to give the desired product, N-[1-(4-cyano-5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide (0.076 g, 15% yield), a compound of this invention. 1 H NMR(500MHz,chloroform-d)δ ppm 1.80(d,J=7.02Hz,3H)4.13(s,3H)6.41(quin,J=7.17Hz,1H)7.35-7.40(m,1H)7.43(br d,J=7.17Hz,1H)8.03(s,1H)8.32(s,2H)8.90(d,J=4.88Hz,2H).LCMS:m / z:485 [M+H] +

[0235] Synthesis Example 18 N-Methyl-N-[1-[4-methylsulfonyl-2-[6-(trifluoromethyl)pyrimidin-4-yl]pyrazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide (Compound 125) Step A: Preparation of methyl 2-(methylamino)propanoate hydrochloride To a stirred solution of 2-(methylamino)propanoic acid (N-methyl-DL-alanine) (21 g, 203.6 mmol) in methanol (300 mL) cooled to 0° C. under a nitrogen atmosphere was added thionyl chloride (21 mL, 305 mmol) slowly at 0° C. The mixture was stirred at 0° C. for 15 minutes and then heated to reflux for 5 hours. The reaction mixture was concentrated under reduced pressure to give crude methyl 2-(methylamino)propanoate hydrochloride (28 g, 90% yield) as an oil, which was used in the next step without purification. 1 H NMR(500MHz,DMSO)δ 9.63(bs,NH),9.29(bs,NH),4.11-4.08(m,1H),3.76(s,3H),2.56-2.51(m,3H),1.48(d,J=7.0Hz,3H)

[0236] Step B: Preparation of methyl 2-[[3,5-bis(trifluoromethyl)benzoyl]-methylamino]propanoate To a stirred solution of 3,5-bis(trifluoromethyl)benzoic acid (45 g, 0.174 mmol) in dichloromethane (250 mL) was added dimethylformamide (1 mL), and oxalyl chloride (32.6 mL, 0.383 mol) was added dropwise at 0° C. under a nitrogen atmosphere. The mixture was stirred at ambient temperature for 3 hours and then concentrated under reduced pressure to give the crude acid chloride. In a separate dry round-bottom flask, methyl 2-(methylamino)propanoate hydrochloride (obtained as described above, 26.6 g, 0.174 mol) was dissolved in tetrahydrofuran (100 mL), N,N-diisopropylethylamine (155 mL, 0.87 mol) was added, and the acid chloride prepared above was added dropwise as a solution in tetrahydrofuran (150 mL) at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 16 hours. The reaction mixture was poured into ice-cold water (300 mL) and extracted with ethyl acetate (200 mL × 3). The combined organic phase was washed with water (100 mL) and saturated aqueous sodium chloride solution (100 mL), dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to flash column chromatography (0-20% ethyl acetate in petroleum ether) to give methyl 2-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]propanoate (45 g, 62% yield) as a yellow liquid. LCMS(ESI)[M+H] + :358.17. 1 H NMR(500MHz,CDCl3)δ 7.94-7.91(m,3H),5.28-5.24(m,1H),3.79(s,3H),2.94(s,3H),1.56(d,3H)

[0237] Step C: Preparation of N-methyl-N-(1-methyl-3-methylsulfonyl-2-oxo-propyl)-3,5-bis(trifluoromethyl)benzamide To a stirred solution of dimethyl sulfone (9.85 g, 104.7 mmol) in tetrahydrofuran (220 mL) was added n-butyllithium (2.5 M in hexane, 38 mL, 95 mmol) under a nitrogen atmosphere at 0° C. and stirred at 0° C. for 20 minutes. The mixture was cooled to −78° C., and a solution of methyl 2-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]propanoate (17 g, 47.6 mmol) in dry tetrahydrofuran (50 mL) was added dropwise at −78° C. and allowed to warm slowly to 0° C. over 1 hour. The reaction mixture was poured into cold 1N aqueous hydrogen chloride solution (300 mL) and extracted with ethyl acetate (200 mL × 3). The combined organic layers were washed with water (100 mL), saturated aqueous sodium chloride solution (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to flash column chromatography (0-50% ethyl acetate in petroleum ether) to give N-methyl-N-(4-(methylsulfonyl)-3-oxobutan-2-yl)-3,5-bis(trifluoromethyl)benzamide (18.5 g, 92% yield) as a white solid. LCMS(ESI)[M+H] + :420.10 1 H NMR(400MHz,CDCl3)δ 7.98(bs,1H),7.92(bs,2H),4.71(q,J=6.8Hz,1H),4.28-4.19(m,2H),3.12(s,3H),3.06(s,3H),1.56(d,J=7.2Hz,3H)

[0238] Step a: Preparation of [6-(trifluoromethyl)pyrimidin-4-yl]hydrazine To a stirred solution of 4-chloro-6-(trifluoromethyl)pyrimidine (1 g, 5.4 mmol) in ethanol (10 mL) was added hydrazine monohydrate (0.52 mL, 10.8 mmol) and triethylamine (0.83 mL, 5.94 mmol) at 25° C. The reaction mixture was stirred at 100° C. for 5 hours and then concentrated under reduced pressure. The resulting crude residue was diluted with chloroform (20 mL), filtered through Celite, and concentrated to a solid. This solid was triturated with diethyl ether (5 mL) and n-pentane (10 mL). The resulting solid was dried under vacuum to give the title material (1 g, crude) as an off-white solid. LCMS(ESI)[M+H] + :178.91. 1 H NMR(400MHz,CDCl3)δ 8.64(s,1H),7.16(bs,1H),6.93(s,1H),3.94(bs,2H)

[0239] Steps D&E: Preparation of N-methyl-N-[1-[4-methylsulfonyl-2-[6-(trifluoromethyl)pyrimidin-4-yl]pyrazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide To a stirred solution of N-methyl-N-(4-(methylsulfonyl)-3-oxobutan-2-yl)-3,5-bis(trifluoromethyl)benzamide (500 mg, 1.19 mmol) in dichloromethane (10 mL) was added dimethylformamide dimethyl acetal (0.46 mL, 3.57 mmol) at ambient temperature under a nitrogen atmosphere. The reaction mixture was stirred at ambient temperature for 16 hours and then concentrated under reduced pressure to give a crude residue. This residue was dissolved in ethanol (5 mL), acetic acid (1.5 mL) and [6-(trifluoromethyl)pyrimidin-4-yl]hydrazine (1 g obtained above in Step 1a) were added, and the mixture was heated at 100° C. for 4 hours. The reaction mixture was concentrated under reduced pressure, and the resulting crude material was treated with saturated aqueous sodium bicarbonate solution (30 mL) to neutral pH, followed by extraction with dichloromethane (30 mL×3). The combined organic phase was washed with water (30 mL) and saturated aqueous sodium chloride solution (30 mL), and dried over sodium sulfate. The organic phase was concentrated under reduced pressure, and the residue was purified by column chromatography eluting with 50% ethyl acetate in petroleum ether to obtain the compound of the present invention, N-methyl-N-[1-[4-methylsulfonyl-2-[6-(trifluoromethyl)pyrimidin-4-yl]pyrazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide (300 mg, yield 42%) as a white solid. LCMS(ESI)[M+H] + :590.19 1 H NMR(400MHz,CDCl3)δ 9.30(s,1H),8.32(s,1H),8.06(s,1H),7.88(bs,1H),7.67(bs,2H),6.45(q,J=7.2Hz,1H),3.29(s,3H),3.20(s,3H),2.02(d,J=7.2Hz,3H)

[0240] The following compounds can be prepared by the procedures described herein and methods known in the art. The following abbreviations are used in the table below: Me means methyl, Et means ethyl, i-Pr means isopropyl, i-Bu means isobutyl, c-Pr means cyclopropyl, and OMe means methoxy.

[0241] Table 1 [ka] Q is Q-1 and R 4 is CN and R 5 is NH2.

[0242] [Table 6]

[0243] [Table 7] Table 2 shows the R 4 This is the same as Table 1 except that is NO2. Table 3 shows the R 4 This is the same as Table 1 except that is Me. Table 4 shows the R 5 Identical to Tables 1-3 except that is NHMe. Table 5 shows the R 5 Identical to Tables 1-3 except that is OMe. Table 6 shows the R 5 Identical to Tables 1-3 except that is SMe. Table 7 shows the R 5 This is the same as Tables 1 to 3, except that is Cl. Table 8 is identical to Tables 1-7 except that Q is Q-2. Table 9 is identical to Tables 1-7 except that Q is Q-3. Table 10 is identical to Tables 1-7 except that Q is Q-4. Table 11 is identical to Tables 1-7 except that Q is Q-5. Table 12 is identical to Tables 1-7 except that Q is Q-6. Table 13 is identical to Tables 1-7 except that Q is Q-7. Table 14 is identical to Tables 1-7 except that Q is Q-8. Table 15 is identical to Tables 1-7 except that Q is Q-9. Table 16 is identical to Tables 1-7 except that Q is Q-10. Table 17 is identical to Tables 1-7 except that Q is Q-11. Table 18 is identical to Tables 1-7 except that Q is Q-12. Table 19 is identical to Tables 1-7 except that Q is Q-13. Table 20 is identical to Tables 1-7 except that Q is Q-14. Table 21 is identical to Tables 1-7 except that Q is Q-15. Table 22 is identical to Tables 1-7 except that Q is Q-16. Table 23 is identical to Tables 1-7 except that Q is Q-17.

[0244] Table 24 [ka] Table 24 is identical to Tables 1-23 except that the structures shown under the heading "Table 1" replace the structures shown above.

[0245] Table 25 [ka] Table 25 is identical to Tables 1-23 except that the structures shown under the heading "Table 1" are replaced by the structures shown above.

[0246] Table 26 [ka] Q is Q-1 and R 4 is CN and R 5 is NH2

[0247] [Table 8]

[0248] [Table 9] Table 27 shows the R 4 This is the same as Table 26 except that is NO2. Table 28 shows the R 4 Identical to Table 26 except that is Me. Table 29 shows the R 5 Identical to Tables 26-28, except that is NHMe. Table 30 shows the R 5 Identical to Tables 26-28 except that is OMe. Table 31 shows the R 5 Identical to Tables 26-28 except that is SMe. Table 32 shows the R 5 Identical to Tables 26 to 28, except that is Cl. Table 33 is identical to Tables 26-32 except that Q is Q-2. Table 34 is identical to Tables 26-32 except that Q is Q-3. Table 35 is identical to Tables 26-32 except that Q is Q-4. Table 36 is identical to Tables 26-32 except that Q is Q-5. Table 37 is identical to Tables 26-32 except that Q is Q-6. Table 38 is identical to Tables 26-32 except that Q is Q-7. Table 39 is identical to Tables 26-32 except that Q is Q-8. Table 40 is identical to Tables 26-32 except that Q is Q-9. Table 41 is identical to Tables 26-32 except that Q is Q-10. Table 42 is identical to Tables 26-32 except that Q is Q-11. Table 43 is identical to Tables 26-32 except that Q is Q-12. Table 44 is identical to Tables 26-32 except that Q is Q-13. Table 45 is identical to Tables 26-32 except that Q is Q-14. Table 46 is identical to Tables 26-32 except that Q is Q-15. Table 47 is identical to Tables 26-32 except that Q is Q-16. Table 48 is identical to Tables 26-32 except that Q is Q-17.

[0249] Table 49 [ka] Table 49 is identical to Tables 26-48 except that the structures shown under the heading "Table 49" replace the structures shown above.

[0250] Table 50 [ka] Table 50 is identical to Tables 26-48 except that the structures shown under the heading "Table 50" replace the structures shown above.

[0251] Specific compounds of Formula 1 prepared by the methods and variations described above in Schemes 1-13 and Synthetic Examples 1-18 are set forth in the index table below. The following abbreviations may be used: Cmpd stands for compound, t is tertiary, c is cyclo, Me is methyl, Et is ethyl, and Ph is phenyl. The abbreviation "Ex." stands for "Example," followed by a number indicating the synthetic example in which the compound was prepared.

[0252] Melting point data (MP) are reported as a temperature range (e.g., 122-126). Mass spectral data (MS) are reported as a single number (e.g., 542). For mass spectral data (AP+(M+1)), the number reported is the molecular weight (M) of the parent molecular ion formed by adding H+ (molecular weight of 1) to the molecule, giving the M+1 peak observed by mass spectrometry using atmospheric pressure chemical ionization (AP+). Alternate molecular ion peaks (e.g., M+2 or M+4) that occur in compounds containing multiple halogens are not reported.

[0253] index table A [ka]

[0254] [Table 10]

[0255] [Table 11]

[0256] [Table 12]

[0257] [Table 13]

[0258] [Table 14]

[0259] [Table 15]

[0260] The compounds of the present invention will generally be used as the invertebrate pest control active ingredient in a composition, i.e., formulation, with at least one additional ingredient selected from the group consisting of surfactants, solid diluents, and liquid diluents, which acts as a carrier. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, the mode of application, and environmental factors such as soil type, moisture, and temperature.

[0261] Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions, oil-in-water emulsions, flowable concentrates, and / or suspoemulsions), which can optionally be thickened to gels. Common types of aqueous liquid compositions include soluble concentrates, suspension concentrates, capsule suspensions, concentrated emulsions, microemulsions, oil-in-water emulsions, flowable concentrates, and suspoemulsions. Common types of non-aqueous liquid compositions are emulsifiable concentrates, microemulsifiable concentrates, dispersible concentrates, and oil dispersions.

[0262] Common types of solid compositions include dusts, powders, granules, pellets, prills, pastilles, tablets, and fill films (including seed coatings), which can be water-dispersible ("wettable") or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly useful for seed treatments. Active ingredients can be (micro)encapsulated and further processed into suspensions or solid formulations; alternatively, entire formulations of active ingredients can be encapsulated (or "overcoated"). Encapsulation can control or delay the release of the active ingredient. Emulsifiable granules combine the advantages of both emulsifiable concentrate and dry granule formulations. High-strength compositions are primarily used as intermediates for further formulation.

[0263] Sprayable formulations are typically spread in a suitable medium before spraying. Such liquid and solid formulations are formulated to be easily diluted in the spray medium, usually water, but sometimes in another suitable medium, such as an aromatic or paraffinic hydrocarbon or vegetable oil. Spray volumes can range from about one to several thousand liters per hectare, but more typically range from about 10 to several hundred liters per hectare. Sprayable formulations can be tank-mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the plant's growing medium. Liquid and dry formulations can be injected directly into drip irrigation systems or metered into furrows at planting. Liquid and solid formulations can be applied to seeds of crops and other desirable vegetation as seed treatments before planting to protect developing roots and other underground plant parts and / or leaves by systemic absorption.

[0264] Formulations will typically contain active ingredients, diluents, and surfactants within the following approximate ranges, which add up to 100 weight percent:

[0265] [Table 16]

[0266] Examples of solid diluents include clays such as bentonite, montmorillonite, attapulgite, kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and sodium bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.

[0267] Examples of liquid diluents include water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), alkyl phosphates (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oil, normal paraffin, isoparaffin), alkylbenzenes, alkylnaphthalenes, glycerin, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatic hydrocarbons, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone, and 4-hydroxy-4-methyl-2-pentanoic acid. Liquid diluents include glycerol esters of saturated and unsaturated fatty acids (typically C6-C8), glycerol esters of saturated and unsaturated fatty acids (typically C6-C8). 22Liquid diluents also include glycerol esters of vegetable oils (e.g., olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut, and palm kernel oils), fats of animal origin (e.g., beef tallow, pork fat, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated), where the fatty acids can be obtained by hydrolysis of glycerol esters from vegetable and animal sources and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.

[0268] The solid and liquid compositions of the present invention often contain one or more surfactants. Surfactants (also known as "surface active agents"), when added to a liquid, generally modify, and in most cases reduce, the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in the surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers, or antifoaming agents.

[0269] Surfactants can be classified as nonionic, anionic, or cationic. Nonionic surfactants useful for the present compositions include, but are not limited to, alcohol alkoxylates, such as those based on natural and synthetic alcohols (which may be branched or linear) and prepared from alcohols and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof; amine ethoxylates, alkanolamides, and ethoxylated alkanolamides; alkoxylated triglycerides, such as ethoxylated soybean oil, castor oil, and rapeseed oil; alkylphenol alkoxylates, such as octylphenol ethoxylate, nonylphenol ethoxylate, dinonylphenol ethoxylate, and dodecylphenol ethoxylate (prepared from phenol and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide, and the end blocks of which are prepared from propylene oxide. , reverse block polymers; ethoxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenols (including those prepared from ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); fatty acid esters, glycerol esters, lanolin-based derivatives, polyethoxylate esters such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters, and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives such as sorbitan esters; polymeric surfactants such as random copolymers, block copolymers, alkyd PEG (polyethylene glycol) resins, graft or comb polymers, and star polymers; polyethylene glycol (PEG); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar derivatives such as sucrose esters, alkyl polyglycosides, and alkyl polysaccharides.

[0270] Useful anionic surfactants include, but are not limited to, alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonic acid derivatives; lignin and lignin derivatives such as lignosulfonates; maleic acid or succinic acid or anhydrides; olefin sulfonates, phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates, and phosphate esters of styrylphenol ethoxylates; protein-based surfactants; sarcosine derivatives; styrylphenol ether sulfonates; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides such as N,N-alkyl taurates; sulfonates of benzene, cumene, toluene, xylene, and dodecyl and tridecyl benzene; sulfonates of condensed naphthalenes; sulfonates of naphthalene and alkyl naphthalenes; sulfonates of fractionated petroleum oils; sulfosuccinamates; and sulfosuccinates and their derivatives, such as dialkyl sulfosuccinate salts.

[0271] Useful cationic surfactants include, but are not limited to, amides and ethoxylated amides; amines such as N-alkylpropanediamines, tripropylenetriamine, and dipropylenetetramine; and ethoxylated amines, ethoxylated diamines, and propoxylated amines (prepared from amines and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts, and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

[0272] Also useful in the compositions of the present invention are mixtures of nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants. Nonionic, anionic, and cationic surfactants and their recommended uses are disclosed in various published references, including McCutcheon's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A.S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.

[0273] The compositions of the present invention may further contain formulation aids and additives known to those skilled in the art as formulation aids, some of which may also function as solid diluents, liquid diluents, or surfactants. Such formulation aids and additives may control pH (buffering agents), foaming during processing (antifoaming agents such as polyorganosiloxanes), active ingredient settling (suspending agents), viscosity (thixotropic thickeners), microbial growth in the container (antimicrobial agents), product freezing (antifreeze agents), color (dye / pigment dispersions), wash-off (film formers or spreading agents), evaporation (evaporation retardants), and other formulation properties. Film formers include, for example, polyvinyl acetate, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymers, polyvinyl alcohol, polyvinyl alcohol copolymers, and waxes. Examples of formulation aids and additives include those described in McCutcheon's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03 / 024222.

[0274] The compound of Formula 1 and various other active ingredients are typically incorporated into the compositions of the present invention by dissolving the active ingredient in a solvent or by grinding it in a liquid or dry diluent. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is not miscible with water, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Active ingredient slurries having particle sizes up to 2,000 μm can be wet-milled using a media mill to obtain particles with an average particle size of less than 3 μm. Aqueous slurries can be made into finished suspension concentrates (see, e.g., U.S. Pat. No. 3,060,084) or can be further processed by spray drying to form water-dispersible granules. Dry formulations typically require a dry-milling process that results in an average particle size in the range of 2 to 10 μm. Dusts and powders can be prepared by blending and typically milling (e.g., hammer mills or fluid energy mills). Granules and pellets can be prepared by spraying the active material onto a preformed granular carrier or by agglomeration techniques. See Browning, "Agglomeration," Chemical Engineering, December 4, 1967, pp. 147-48; Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57; and International Publication No. WO 91 / 13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442, and German Patent No. 3,246,493. Tablets can be prepared as taught in U.S. Patent Nos. 5,180,587, 5,232,701, and 5,208,030. Films can be prepared as taught in British Patent No. 2,095,558 and U.S. Patent No. 3,299,566.

[0275] For further information on formulation techniques, see T. S. Woods, "The Formulator's Toolbox - Product Forms for Modern Agriculture," in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also the following references: U.S. Pat. No. 3,235,361, column 6, line 16 to column 7, line 19, and Examples 10-41; U.S. Pat. No. 3,309,192, column 5, line 43 to column 7, line 62, and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167, and 169-182; U.S. Pat. No. 2,891,855, column 3, line 66 to column 5, line 17, and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp. 81-96; Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, UK, 2000.

[0276] In the following examples, all formulations are prepared by conventional methods. Compound numbers refer to compounds in Index Table A. Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. Accordingly, the following examples are intended to be merely illustrative and not limiting of the present disclosure in any way. Percentages are by weight unless otherwise specified.

[0277] Example A high strength concentrate Compound 1 98.5% Silica aerogel 0.5% Synthetic amorphous fine silica 1.0%

[0278] Example B Wettable Powder Compound 3 65.0% Dodecylphenol polyethylene glycol ether 2.0% Sodium lignosulfonate 4.0% Sodium silicoaluminate 6.0% Montmorillonite (calcined) 23.0%

[0279] Example C Granules Compound 8 10.0% Attapulgite Granules (Low Volatile Content, 0.71 / 0.30 mm; USS No. 25-50 Sieve) 90.0%

[0280] Example D Extruded pellets Compound 10 25.0% Anhydrous sodium sulfate 10.0% Crude calcium lignosulfonate 5.0% Sodium alkylnaphthalene sulfonate 1.0% Calcium / Magnesium Bentonite 59.0%

[0281] Example E emulsifiable concentrate Compound 11 10.0% Polyoxyethylene sorbitol hexoleate 20.0% C6~C 10 Fatty acid methyl ester 70.0%

[0282] Example F Microemulsion Compound 19 5.0% Polyvinylpyrrolidone-vinyl acetate copolymer 30.0% Alkyl polyglucoside 30.0% Glyceryl monooleate 15.0% Water 20.0%

[0283] Example G Seed treatment Compound 20 20.00% Polyvinylpyrrolidone-vinyl acetate copolymer 5.00% Montan Acid Wax 5.00% Calcium lignosulfonate 1.00% Polyoxyethylene / Polyoxypropylene Block Copolymer 1.00% Stearyl alcohol (POE 20) 2.00% Polyorganosilane 0.20% Colorant: Red dye 0.05% Water 65.75%

[0284] Example H Fertilizer sticks Compound 33 2.5% Pyrrolidone-styrene copolymer 4.8% Tristyrylphenyl 16-ethoxylate 2.3% Talc 0.8% Cornstarch 5.0% Time-release fertilizer 36.0% Kaolin 38.0% Water 10.6%

[0285] Example I Suspension concentrate Compound 34 35% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone antifoaming agent 0.1% 1,2-benzisothiazolin-3-one 0.1% Water 53.7%

[0286] Example J Emulsion in water Compound 39 10.0% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone antifoaming agent 0.1% 1,2-benzisothiazolin-3-one 0.1% Aromatic petroleum hydrocarbons 20.0 Water 58.7%

[0287] Example K oil dispersion Compound 35 25% Polyoxyethylene sorbitol hexaoleate 15% Organically modified bentonite clay 2.5% Fatty acid methyl esters 57.5%

[0288] Example L Suspension emulsion Compound 38 10.0% Imidacloprid 5.0% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone antifoaming agent 0.1% 1,2-benzisothiazolin-3-one 0.1% Aromatic petroleum hydrocarbons 20.0% Water 53.7%

[0289] Example M Suspension concentrate Compound 2 35% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone antifoaming agent 0.1% 1,2-benzisothiazolin-3-one 0.1% Water 53.7%

[0290] Example N Emulsion in water Compound 7 10.0% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone antifoaming agent 0.1% 1,2-benzisothiazolin-3-one 0.1% Aromatic petroleum hydrocarbons 20.0 Water 58.7%

[0291] Example O oil dispersion Compound 30 25% Polyoxyethylene sorbitol hexaoleate 15% Organically modified bentonite clay 2.5% Fatty acid methyl esters 57.5%

[0292] Example P Suspension emulsion Compound 31 10.0% Imidacloprid 5.0% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone antifoaming agent 0.1% 1,2-benzisothiazolin-3-one 0.1% Aromatic petroleum hydrocarbons 20.0% Water 53.7%

[0293] The compounds of the present invention are active against a wide range of invertebrate pests. These pests include invertebrates that live in a variety of environments, such as plant foliage, roots, soil, harvested crops or other foods, or building structures. These pests include invertebrates that feed on foliage (including leaves, stems, flowers, and fruits), seeds, wood, or fiber, thereby causing damage or harm to, for example, growing and stored agricultural crops, forestry crops, greenhouse crops, ornamental plants, nursery crops, stored food or fiber products, or buildings or their structures or components. Those skilled in the art will understand that not all compounds are equally effective against all developmental stages of all pests.

[0294] Thus, these compounds and compositions are useful agriculturally to protect agricultural crops from herbivorous invertebrate pests, and non-agronomically to protect other horticultural crops and plants from herbivorous invertebrate pests. This utility includes protecting crops and other plants (i.e., both agricultural and non-agronomic) that contain genetic material introduced by genetic engineering (i.e., gene transfer) or modified by mutagenesis to provide advantageous traits. Examples of such traits include herbicide resistance, resistance to herbivorous pests (e.g., insects, mites, aphids, spiders, nematodes, snails, plant pathogenic fungi, bacteria, and viruses), improved plant growth, improved tolerance to adverse growing conditions such as high or low temperatures, low or high soil moisture, and high salinity, increased flowering or fruiting, higher yield, earlier maturation, higher quality and / or nutritional value of the harvested product, or improved storage or processing characteristics of the harvested product. Transgenic plants can be modified to express multiple traits. Examples of plants containing traits resulting from genetic engineering or mutagenesis include corn, cotton, soybean, and potato varieties that express insecticidal Bacillus thuringiensis toxins, such as YIELD GARD®, KNOCKOUT®, STARLINK®, BOLLGARD®, NuCOTN®, and NEWLEAF®, INVICTA RR2 PRO™, and herbicide-tolerant varieties of corn, cotton, soybean, and rapeseed, such as ROUNDUP READY®, LIBERTY LINK®, IMI®, STS®, and CLEARFIELD®, as well as crops that express N-acetyltransferase (GAT) to provide tolerance to glyphosate herbicides or contain the HRA gene to provide tolerance to herbicides that inhibit acetolactate synthase (ALS). The present compounds and compositions may exhibit improved efficacy due to traits introduced by genetic engineering or modified by mutagenesis, thereby improving the phenotypic expression or efficacy of the trait or increasing the invertebrate pest control efficacy of the present compounds and compositions.In particular, the compounds and compositions may exhibit enhanced efficacy through the phenotypic expression of proteins or other natural products that are toxic to invertebrate pests, resulting in more than additive control of these pests.

[0295] The compositions of the present disclosure may optionally also include a fertilizer composition containing at least one plant nutrient selected from nitrogen, phosphorus, potassium, sulfur, calcium, magnesium, iron, copper, boron, manganese, zinc, and molybdenum. Of note are compositions containing at least one fertilizer composition containing at least one plant nutrient selected from nitrogen, phosphorus, potassium, sulfur, calcium, and magnesium. The compositions of the present invention further containing at least one plant nutrient may be in liquid or solid form. Of note are solid formulations in the form of granules, small rods, or tablets. Solid formulations, including fertilizer compositions, may be prepared by mixing the compounds or compositions of the present invention and the fertilizer composition together with the formulation ingredients, and then preparing the formulation by a method such as granulation or extrusion. Alternatively, the solid formulation may be prepared by spraying a solution or suspension of the compounds or compositions of the present invention in a volatile solvent onto a dimensionally stable mixture, such as a pre-prepared fertilizer composition in the form of granules, small rods, or tablets, and then evaporating the solvent.

[0296] Non-agricultural uses refer to invertebrate pest control in areas other than the field of crop plants. Non-agricultural uses of the present compounds and compositions include the control of invertebrate pests in stored grains, legumes, and other foods, and in fabrics such as clothing and carpets. Non-agricultural uses of the present compounds and compositions also include the control of invertebrate pests in ornamental plants, forests, gardens, roadsides, and railroad rights-of-way, as well as in turf such as lawns, golf courses, and pastures. Non-agricultural uses of the present compounds and compositions also include the control of invertebrate pests in homes and other buildings that may be occupied by humans and / or companion animals, farms, ranches, zoo animals, or other animals. Non-agricultural uses of the present compounds and compositions also include the control of pests such as termites that may damage wood or other structural materials used in buildings.

[0297] Examples of agronomic or non-agronomic invertebrate pests include Lepidoptera such as armyworms, rootworms, loopers, and tobacco budworm eggs, larvae, and adults in the Noctuidae family (e.g., pink stem borer (Sesamia inferens Walker)), Lepidoptera such as armyworms, rootworms, loopers, and tobacco budworm eggs in the Noctuidae family, corn stalk borer (Sesamia nonagrioides Lefebvre), southern armyworm (Spodoptera eridania Cramer), fall armyworm (Spodoptera fugiperda), and the like. J.S. Smith), beet armyworm (Spodoptera exigua Huebner), cotton leafworm (Spodoptera littoralis Boisduval), yellowstriped armyworm (Spodoptera ornithogalli Guenee), cutworm moth (Agrotis ipsilon Hufnagel), velvetbean caterpillar (Anticarsia gemmatalis Huebner), green fruitworm (Lithophane antennata Walker), cabbage armyworm armyworm (Barathra brassicae Linnaeus), soybean looper (Pseudoplusia includensWalker), nettle looper (Trichoplusia ni Huebner), cotton bollworm (Heliothis virescens Fabricius); borer pests from the Pyralidae family, cocooning pests, colonial pests that nest in the leaves, cornworms, caterpillars and leaf-feeding pests that leave the veins (e.g., European corn borer (Ostrinia nubilalis Huebner), navel orangeworm (Amyelois transitella Walker), corn beetle larvae (Crambus caliginosellus Clemens), black-banded corn moth (Herpetogramma licarsisalis Sod webworms (Crambinae) such as the sugarcane stem borer (Chilo infuscatellus Snellen), the tomato small borer (Neoleucinodes elegantalis Guenee), the green leafroller (Cnaphalocerus medinalis), the grape leaffolder (Desmia funeralis Huebner), the melon worm (Diaphania nitidalis Stoll), and the cabbage center grub (Helluala hydralis Guenee), yellow stem borer (Scirpophaga incertulas Walker), early shoot borer (Scirpophaga infuscatellusSnellen), white stem borer (Scirpophaga innotata Walker), top shoot borer (Scirpophaga nivella Fabricius), dark-headed rice borer (Chilo polychrysus Meyrick), rice stem borer (Chilo suppressalis Walker), cabbage cluster caterpillar (Crocidolomia binotalis English); leafrollers in the Tortricidae family, bud-feeding pests, seed-feeding pests, and fruit-feeding pests (e.g., codling moth (Cydia pomonella) pomonella Linnaeus), Japanese shrike moth (Endopiza viteana Clemens), Japanese pear fruit moth (Grapholita molesta Busck), citrus false codling moth (Cryptophlebia leucotreta Meyrick), citrus borer (Ecdytolopha aurantiana Lima), redbanded leafroller (Argyrotaenia velutinana Walker), obliquebanded leafroller (Choristoneura rosaceana Harris), light brown apple moth moth (Epiphyas postvittanaWalker), grape borer moth (Eupoecilia ambiguella Huebner), apple bud moth (Pandemis pyrusana Kearfott), omnivorous leafroller (Platynota stultana Walsingham), barred fruit-tree tortrix (Pandemis cerasana Huebner), apple brown tortrix (Pandemis heparana Denis & Schiffermueller); as well as many other economically important Lepidoptera (e.g., diamondback moth (Plutella xylostella Linnaeus), pink bollworm moth (Pectinophora gossypiella Saunders), gypsy moth (Lymantria dispar Linnaeus), peach fruit borer (Carposina niponensis Walsingham), peach twig borer (Anarsia lineatella Zeller), potato tuberworm (Phthorimaea operculella Zeller), spotted teniform leafminer (Siberian tiger moth), and the like. leafminer (Lithocolletis blancardella Fabricius), Asiatic apple leafminer (Lithocolletis ringoniella Matsumura), rice leaffolder (Lerodea eufala Edwards), apple leafminer (Leucoptera scitella Zeller);Eggs, nymphs, and adults of the order Blattodea, which includes cockroaches from the families Blattellidae and Blattidae (e.g., the Asian cockroach (Blatta orientalis Linnaeus), the Asian cockroach (Blatella asahinai Mizukubo), the German cockroach (Blattella germanica Linnaeus), the brown-striped cockroach (Supella longipalpa Fabricius), the American cockroach (Periplaneta americana Linnaeus), the brown brown cockroach (Periplaneta brunnea Burmeister), and the Madera cockroach (Leucophaea maderae) Fabricius), the American cockroach (Periplaneta fuliginosa Service), the American cockroach (Periplaneta australasiae Fabr.), the grey cockroach (Nauphoeta cinerea Olivier) and the smooth cockroach (Symploce pallens Stephens);Eggs, folivorous, frugivorous, root-feeding, seed-feeding, and vesicular-feeding larvae and adults of Coleoptera, including weevils from the families Anthribidae, Bruchidae, and Curculionidae (e.g., boll weevil (Anthonomus grandis Boheman), rice water weevil (Lissorhoptrus oryzophilus Kuschel), dry rice weevil (Sitophilus granarius Linnaeus), rice weevil (Sitophilus oryzae Linnaeus), annual bluegrass weevil (Listronotus maculicollis Dietz), bluegrass billbug (Sphenophorus parvulus Gyllenhal), hunting billbug (Sphenophorus venatus vestitus), Denver billbug (Sphenophorus cicatristriatus Fahraeus); flea beetles, cucumber beetles, root-eating nematodes, leaf beetles, potato beetles, and leaf miners in the Chrysomelidae family (e.g., Colorado potato beetle (Leptinotarsa ​​decemlineata Say)), western corn rootworm (Diabrotica virgifera virgifera LeConte));Scarab beetles and other beetles from the family Scarabaeidae (e.g., Japanese beetle (Popillia japonica Newman), oriental beetle (Anomala orientalis Waterhouse, Exomala orientalis (Waterhouse) Baraud)), northern masked chafer (Cyclocephala borealis Arrow), southern masked chafer (Cyclocephala immaculata Olivier or C. lurida Bland), dung beetle and white grub (Aphodius spp.), black turfgrass ataenius (Ataenius spretulus Haldeman), green June beetle (Cotinis nitida Linnaeus), Asiatic garden beetle (Maladera castanea Arrow), May / June beetles (Phyllophaga spp.), and European chafer (Rhizotrogus majalis Razoumowsky); dermestid beetles from the family Dermestidae; click beetles from the family Elateridae; bark beetles from the family Scolytidae and red flour beetles from the family Tenebrionidae;

[0298] Additionally, agricultural and non-agricultural pests include: eggs, adults and larvae of the order Dermaptera, including earwigs of the family Forficulidae (e.g., European earwig (Forficula auricularia Linnaeus), black earwig (Chelisoches morio Fabricius); eggs, adults and larvae of the orders Hemiptera and Homoptera, including mirid bugs of the family Miridae, cicadas of the family Cicadidae, leafhoppers of the family Cicadellidae (e.g., Empoasca spp.)), bed bugs of the family Cimicidae (e.g., Cimex lectularius Linnaeus), planthoppers of the families Fulgoroidae and Delphacidae, treehoppers of the family Membracidae, psyllids of the family Psyllidae, whiteflies of the family Aleyrodidae, aphids of the family Aphididae, root aphids of the family Phylloxeridae, mealybugs of the family Pseudococcidae Scale insects of the families Coccidae, Diaspididae and Margarodidae, Tingidae, Pentatomidae, Lygaeidae, and Lygaeidae (e.g., hairy stink bugs (Blissus leucopterus hirtus)). Eggs, larvae, adults, and nymphs of the following bugs: the southern American rice bug (Blissus insularis Barber) and other seed bugs, the spittlebug (Cercopidae), the corner bug (Coreidae), and the spotted stink bug and cotton stainer (Pyrrhocoridae).

[0299] Agronomic and non-agronomic pests also include: spider mites and red mites in the Tetranychidae family (e.g., Panonychus ulmi Koch), two-spotted spider mite Tetranychus urticae (Koch), McDaniel mite Tetranychus mcdanieli McGregor); small spider mites in the Tenuipalpidae family (e.g., citrus small spider mite Brevipalpus lewisi eggs, larvae, nymphs and adults of the order Acari (mites), such as Acarina gracilis (Acarina gracilis) and Acarina nigra (Acarina gracilis) (McGregor); rust and eriophyid mites and other leaf-feeding mites in the family Eriophyidae; house mites in the family Epidermoptidae; hair follicle mites in the family Demodicidae; grain mites in the family Glycyphagidae; ticks in the family Ixodidae, commonly known as hard mites (e.g., deer tick (Ixodes scapularis Say), Australian tick (Ixodes holocyclus Neumann), dermacentor variabilis Say), lone star tick (Amblyomma americanum) Linnaeus) and ticks in the Argasidae family, commonly known as ulcer mites (e.g., the relapsing fever vector tick (Ornithodoros turicata), the common poultry tick (Argas radiatus); scabies and eczema mites in the Psoroptidae, Pyemotidae, and Sarcoptidae families; grasshoppers, locusts, and crickets (e.g., the carrion grasshopper (e.g., Melanoplus sanguinipes Fabricius), M. differentialis (M.differentialis Thomas), American locusts (e.g., Schistocerca americana Drury), desert grasshoppers (Schistocerca gregaria Forskal), migratory locusts (Locusta migratoria Linnaeus), bush locusts (Zonocerus spp.), European house crickets (Acheta domesticus Linnaeus), mole crickets (e.g., Tawny mole crickets (Scapteriscus vicinus Scudder) and southern mole crickets (Scapteriscus borellii Eggs, adults and juveniles of Orthoptera, including E. gibba Giglio-Tos; leafminers (e.g., Liriomyza spp., such as the serpentine vegetable leafminer (Liriomyza sativae Blanchard)), midges, fruit flies (Tephritidae), woodminers (e.g., Oscinella frit Linnaeus), maggot flies, house flies (e.g., Musca domestica Linnaeus), little house flies (e.g., Fannia canicularis Linnaeus, F. femoralis Stein), stable flies (e.g., Stomoxys calcitrans Linnaeus), face flies, horn flies, blow flies (e.g., Chrysomya spp., Phormia spp.) and other muscoid fly pests, horse flies (e.g., Tabanus spp.), bot flies (e.g., Gastrophilus spp., Oestrus spp.), cow flies (e.g. Hypoderma spp.), deer flies (e.g. Chrysops spp.), sheep lice (e.g. Melophagus ovinus Linnaeus) and other Brachycera, mosquitoes (e.g. Aedes spp., Anopheles spp., Culex spp.), black flies (e.g. Prosimulium spp., Simulium spp.), eggs, adults, and juveniles of Diptera, including black midges, sand flies, sciarid gnats, and other Nematocera; eggs, adults, and juveniles of Thysanoptera, including onion thrips (Thrips tabaci Lindeman), flower thrips (Frankliniella spp.), and other leaf-feeding thrips; eggs, adults, and juveniles of Florida carpenter ant (Camponotus floridanus Buckley), red carpenter ant (Camponotus ferrugineus Fabricius), black carpenter ant (Camponotus pennsylvanicus De Geer), the white-legged ant (Technomyrmex albipes fr. Smith), the giant ant (Pheidole sp.), brown rice ant (Tapinoma melanocephalum Fabricius); house ant (Monomorium pharaonis Linnaeus), small fire ant (Wasmannia auropunctata Roger), red fire ant (solenopsis geminata Fabricius), red fire ant (solenopsis invicta Buren), Argentine ant (Iridomyrmex humilis Mayr), long-legged fire ant (Paratrechina longicornis Latreille), brown ant (Tetramorium caespitum Insect pests of the order Hymenoptera, including ants of the Formicidae family, including the small brown ant (Lasius alienus Foerster), the small brown ant (Lasius alienus Foerster), and the field ant (Tapinoma sessile Say). Other Hymenoptera include bees (including carpenter bees), hornets, yellow jacket hornets, large wasps, and sawflies (Neodiprion spp.; Cephus spp.); termites (e.g., Macrotermes sp., Odontotermes obesus), and other insect pests of the order Hymenoptera, including the family Formicidae, including the small brown ant (Lasius alienus Foerster), the small brown ant (Tapinoma sessile Say), and the field ant (Tapinoma sessile Say). Rambur), Kalotermitidae (e.g., Cryptotermes sp.), and Rhinotermitidae (e.g., Reticulitermes sp., Coptotermes sp.Termites in Heterotermes tenuis Hagen, Rhinotermites (Reticulitermes flavipes Kollar), European termites (Reticulitermes hesperus Banks), Formosan termites (Coptotermes formosanus Shiraki), Hawaiian termites (Incisitermes immigrans Snyder), powder post termite (Cryptotermes brevis Walker), drywood termite (Incisitermes snyderi Light), and southeastern subterranean termites. subterranean termite (Reticulitermes virginicus Banks), western drywood termite (Incisitermes minor Hagen), Nasutitermes sp.insect pests of the order Isoptera, which includes wood termites such as the silverfish (Lepisma saccharina Linnaeus) and other economically important termites; and insect pests of the order Tysanura, such as the silverfish (Thermobia domestica Packard) and the silverfish (Thermobia domestica Packard). Additional arthropod pests that are encompassed include spiders from the order Araneae, such as the brown recluse spider (Loxosceles reclusa Gertsch & Mulaik) and the black widow spider (Latrodectus mactans Fabricius), and centipedes from the order Scutigeromorpha, such as the house centipede (Scutigera coleoptrata Linnaeus).

[0300] Examples of invertebrate pests of stored grain include the boston bollworm (Prostephanus truncatus), bark beetle (Rhyzopertha dominica), rice weevil (Stiophilus oryzae), corn weevil (Stiophilus zeamais), cowpea weevil (Callosobruchus maculatus), red flour beetle (Tribolium castaneum), granary maize weevil (Stiophilus granarius), Indian meal moth (Plodia interpunctella), and the rice weevil (Stiophilus oryzae). interpunctella), the Mediterranean red flour beetle (Ephestia kuhniella) and the small or rust-breasted ring beetle (Cryptolestis ferrugineus).

[0301] The compounds of the invention are effective against pests of the order Lepidoptera (e.g., Alabama argillacea Huebner (cotton leafworm), Archips argyrospila Walker (fruit tree leafroller), A. rosana Linnaeus (European leafroller) and other Archips species, Chilo suppressalis Walker (rice stem borer), Cnaphalocrosis medinalis Guenee (rice leafroller), Crambus caliginosellus Clemens (corn root webworm), Crambus teterrellus Zincken (bluegrass webworm), codling moth, Cydia pomonella Linnaeus (Codling Moth), Earias insulana Boisduval (Spiny Bowlworm), Earias vittella Fabricius (Spotted Bowlworm), Helicoverpa armigera Huebner (Bowworm), Helicoverpa zea Boddie (Tobacco Moth Larva), Heliothis virescens Fabricius (False Tobacco Moth), Herpetogramma licarsisalis Walker (Sod Webworm), Lobesia botrana Denis & Schiffermueller (Grapeberry Moth), Pectinophora gossypiera gossypiella Saunders (larvae of the pink bollworm moth), Phyllocnistis citrella Stainton (orange leafminer), Pieris brassicaeIt is active against the following insecticides: Pieris rapae Linnaeus (large white butterfly), Pieris rapae Linnaeus (cabbage white butterfly), Plutella xylostella Linnaeus (diamond moth), Spodoptera exigua Huebner (beet armyworm), Spodoptera litura Fabricius (common cutworm, cluster caterpillar), Spodoptera frugiperda J. E. Smith (stalk armyworm), Trichoplusia ni Huebner (cabbage looper), and Tuta absoluta Meyrick (tomato leafminer).

[0302] The compounds of the present invention are effective against Acyrthosiphon pisum Harris (pea aphid), Aphiscraccivora Koch (cowpea aphid), Aphis fabae Scopoli (black bean aphid), Aphis gossypii Glover (cotton aphid, melon aphid), Aphis pomi De Geer (apple aphid), Aphis spiraecola Patch (Spirea aphid), Aulacorthum solani Kaltenbach (foxglove aphid), Chaetosiphon fragaefolii Cockerell (strawberry aphid), Diuraphis noxia Kurdjumov / Mordvilko (Russian wheat aphid), Dysaphis plantaginea Paaserini (rosy apple aphid), Eriosoma lanigerum Hausmann (apple aphid), Hyalopterus pruni Geoffroy (mealie plum aphid), Lipaphis erysimi Kaltenbach (false radish aphid), Metopolophium dirrhodum Walker (cereal aphid), Macrosiphum euphorbiae Thomas (potato aphid), Myzus persicae Sulzer (peach-potato aphid, green peach aphid), Nasonovia ribisnigri Mosley (lettuce aphid), Pemphigus spp.) (root aphids and leaf aphids), Rhopalosiphum maidis Fitch (corn aphid), Rhopalosiphum padi Linnaeus (bird cherry oat aphid), Schizaphis graminum Rondani (greengrass aphid), Sitobion avenae Fabricius (English grain aphid), Therioaphis maculata Buckton (spotted alfalfa aphid), Toxoptera aurantii Boyer de Fonscolombe (black citrus aphid), and Toxoptera citricida Kirkaldy (brown citrus aphid); Adelges (parasitic aphid);. Phylloxera devastatrix Pergande (pecan phylloxera); Bemisia tabaci Gennadius (cotton whitefly, cotton whitefly), Bemisia argentifolii Bellows & Perring (silverleaf whitefly), Dialeurodes citri Ashmead (citrus whitefly) and Trialeurodes vaporariorum Westwood (greenhouse whitefly); Empoasca fabae Harris (potato leafhopper), Laodelphaxstriatellus Fallen (smaller brown planthopper), Macrolestes quadrilineatus quadrilineatus Forbes (Aster Leafhopper), Nephotettix cinticeps Uhler (Green Leafhopper), Nephotettix nigropictus Stal (Rice Leafhopper), Nilaparvata lugens Stal (Brown Planthopper), Peregrinus maidis Ashmead (Corn Planthopper), Sogatella furcifera Horvath (White-backed Planthopper), Sogatodes orizicola Muir (Rice Delphacid), Typhlocyba pomaria McAtee (White Apple Leafhopper), Erythroneoura (Grape Leafhopper); Magicidada septendecim Linnaeus (Periodic Cicada);Active against Homoptera, including Icerya purchasi Maskell (cotton scale), Quadraspidiotus perniciosus Comstock (San Jose scale), Planococcus citri Risso (citrus mealybug), Pseudococcus (other mealybugs of the mealybug complex), Cacopsylla pyricola Foerster (sunflower psylla), and Trioza diospyri Ashmead (persimmon psylla);

[0303] The compounds of the present invention are effective against Acrosternum hilare Say (green stink bug), Anasa tristis De Geer (helicopter bug), Blissus leucopterus leucopterus Say (American long-horned stink bug), Cimex lectularius Linnaeus (bed bug), Corythuca gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), Dysdercus suturellus Herrich-Schaeffer (cotton stainer), Euchistus cervus (tomato bug), and the like. servus Say (Brown stink bug), Euchistus variolarius Palisot de Beauvois (One-spotted stink bug), Graptosthetus spp. (Seed bug complex), Halymorpha halys Stall (Brown marbled stink bug), Leptoglossus corculus Say (Leaf-footed pine seed bug), Lygus lineolaris Palisot de Beauvois (Green mistletoe), Nezara viridula Linnaeus (Southern green stink bug), Oebalus pugnax It has activity against Hemiptera, including Oncopeltus fasciatus Dallas (large milkweed bug), Pseudatomoscelis seriatus Reuter (cotton flea hopper), and Rhizopugnax Fabricius (rice stink bug).Other insect orders controlled by the compounds of the invention include Thysanoptera (e.g., Frankliniella occidentalis Pergande (Occidarium flower thrips), Scirthothrips citri Moulton (Cigar thrips), Sericothrips variabilis Beach (Soybean thrips), and Thrips tabaci Lindeman (Onion thrips); and Coleoptera (e.g., Leptinotarsa ​​decemlineata Say (Colorado potato beetle), Epilachna varivestis (L ... varivestis) Mulsant (the common ladybug) and the larvae of click beetles of the genera Agriotes, Athous or Limonius).

[0304] Of note is the use of a compound of the present invention to control and control diamondback moth (Plutella xylostella). Of note is the use of a compound of the present invention to control and control fall armyworm (Spodoptera frugiperda). Of note is the use of a compound of the present invention to control and control western flower thrips (Frankliniella occidentalis). Of note is the use of a compound of the present invention to control and control potato leafhopper (Empoasca fabae). Of note is the use of compounds of the present invention to control and eradicate the corn planthopper (Peregrinus maidis). Of note is the use of compounds of the present invention to control and eradicate the cotton melon aphid (Aphis gossypii). Of note is the use of compounds of the present invention to control and eradicate the green peach aphid (Myzus persicae). Of note is the use of compounds of the present invention to control and eradicate the sweet potato whitefly (Bemisia tabaci).

[0305] The compounds of the present invention may also be useful for increasing the vigor of crop plants. The method involves contacting a crop plant (e.g., leaves, flowers, fruits, or roots) or a seed from which the crop plant grows with a compound of Formula 1 in an amount sufficient to achieve the desired plant vigor effect (i.e., a biologically effective amount). Typically, the compound of Formula 1 is applied in a formulated composition. The compound of Formula 1 is often applied directly to the crop plant or its seeds, but it can also be applied to the locus of the crop plant, i.e., to a part of the environment of the crop plant, particularly one sufficiently close to the crop plant for the compound of Formula 1 to be translocated to the crop plant. The locus relevant to the method most commonly includes the growth medium in which the plant is grown (i.e., the medium that provides nutrients to the plant), typically soil. Thus, treating a crop plant to increase its vigor involves contacting the crop plant, the seed from which the crop plant grows, or the locus of the crop plant with a biologically effective amount of a compound of Formula 1.

[0306] Increased crop vigor can result in one or more of the following observed effects: (a) optimal crop growth as indicated by superior seed germination, crop emergence, and crop stand; (b) improved crop growth as indicated by rapid and robust leaf growth (e.g., as measured by leaf area index), plant height, number of tillers (e.g., in the case of rice), root mass, and total dry weight of the growing parts of the crop; (c) improved crop yield as indicated by time to flowering, flowering duration, number of flowers, total biomass accumulation (i.e., yield), and / or marketability of the fruit or grain grade of the product (i.e., yield quality); (d) improved ability of crops to resist or prevent infection by plant diseases and infestation by arthropod, nematode, or mollusk pests; and (e) improved ability of crops to tolerate environmental stresses, such as extreme temperatures, suboptimal moisture, or exposure to phytotoxic chemicals.

[0307] The compounds of the present invention can increase the vigor of treated plants compared to untreated plants by killing or otherwise preventing the feeding of herbivorous invertebrate pests in the plant's environment. In the absence of such herbivorous invertebrate pest control, the pests reduce plant vigor by consuming plant tissue or sap or transmitting plant pathogens such as viruses. Even in the absence of herbivorous invertebrate pests, the compounds of the present invention can increase plant vigor by modifying the plant's metabolism. In general, the vigor of crop plants will be most significantly increased by treating the plants with the compounds of the present invention when the plants are grown in a non-ideal environment, i.e., an environment that contains one or more unfavorable aspects for the plants to achieve the full genetic potential that they would exhibit in an ideal environment.

[0308] Of note is a method for increasing the vigor of crop plants growing in an environment that includes herbivorous invertebrate pests. Also of note is a method for increasing the vigor of crop plants, where the crop plants are grown in an environment that does not include herbivorous invertebrate pests. Also of note is a method for increasing the vigor of crop plants, where the crop plants are grown in an environment that does not include herbivorous invertebrate pests. Also of note is a method for increasing the vigor of crop plants, where the crop is rice. Also of note is a method for increasing the vigor of crop plants, where the crop is maize (corn). Also of note is a method for increasing the vigor of crop plants, where the crop is soybean.

[0309] The compounds of the present invention can be mixed with one or more other biologically active compounds or agents, including insecticides, fungicides, nematicides, bactericides, miticides, herbicides, herbicide safeners, growth regulators, such as insect molting inhibitors and root stimulators, chemosterilants, semi-chemicals, repellents, attractants, pheromones, feeding stimulants, other bioactive compounds, or insect pathogenic bacteria, viruses, or fungi, to form multi-component insecticides, which provide an even broader spectrum of agronomic and non-agronomic utility. Accordingly, the present invention also relates to compositions comprising a biologically effective amount of a compound of Formula 1, at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, and at least one additional biologically active compound or agent. With respect to the mixtures of the present invention, the other biologically active compound or agent can be formulated together with the compound of the present invention, including the compound of Formula 1, to form a premix, or the other biologically active compound or agent can be formulated separately from the compound of the present invention, including the compound of Formula 1, and the two formulations can be combined together (e.g., in a spray tank) prior to application, or alternatively, applied sequentially.

[0310] Examples of such biologically active compounds or agents that can be formulated with the compounds of the present invention include abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, afidopiropen ([(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a ,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methylcyclopropanecarboxylate), amidoflumet, amitraz, avermectin, azadirachtin, azinphos-methyl, benfuracarb, bensultap, bifenthrin, bifenazate, bistrifluron, borate, buprofezin, cadusafos, carbaryl, Carbofuran, Cartap, Carsol, Chlorantraniliprole, Chlorfenapyr, Chlorfluazuron, Chlorpyrifos, Chlorpyrifos-methyl, Chromafenozide, Clofentezine, Clothianidin, Cyantraniliprole (3-bromo-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-1H-pyrazole-5-carboxamide), Cyclohexyl Raniliprole (3-bromo-N-[2-bromo-4-chloro-6-[[(1-cyclopropylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide), cycloprothrin, cycloxapride ((5S,8R)-1-[(6-chloro-3-pyridinyl)methyl]-2,3,5,6,7,8-hexahydro-9-nitro-5,8-epoxy-1H-imidazo[1,2-a]azepine), cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron, dimefluthrin, dimehypo, dimethoate, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenbutatin oxide, phenytoin Lothion, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flometoquin (2-ethyl-3,7-dimethyl-6-[4-(trifluoromethoxy)phenoxy]-4-quinolinylmethyl carbonate), flonicamid, flubendiamide, flucythrinate, flufenerim, flufenoxuron, flufenoxystrobin (methyl(αE)-2-[[2-chloro-4-(trifluoromethyl)phenoxy]methyl]-α-(methoxymethylene)benzeneacetate), flufensulfon (5-chloro- 2-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]thiazole), fluhexafon, fluopyram, flupiprole (1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(2-methyl-2-propen-1-yl)amino]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile), flupyradifurone (4-[[(6-chloro-3-pyridinyl)methyl](2,2-difluoroethyl)amino]-2(5H)-furanone), fluvalinate, fluoxetine ... s, formetanate, fosthiazate, halofenozide, heptafluthrin ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl 2,2-dimethyl-3-[(1Z)-3,3,3-trifluoro-1-propen-1-yl]cyclopropanecarboxylate), hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, indoxacarb, insecticidal soap, isofenphos, lufenuron, malathion, mepafluthrin ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl (1R,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate), metaflumizone, metaldehyde, methamidophos, methidathion, methiocarb, methomyl, methoprene, methoxychlor, metofluthrin, methoxyfenozide, metofluthrin, monocrotophos, monofluorothrin ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl 3-(2-chloro- N-(2-methyl-1-propen-1-yl)-2,2-dimethylcyclopropanecarboxylate), nicotine, nitenpyram, nithiazine, novaluron, noviflumuron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, propargite, protrifenbut, piflubumid (1,3,5-trimethyl-N-(2-methyl-1-propen-1-yl)-2,2-dimethylcyclopropanecarboxylate), -methyl-1-oxopropyl)-N-[3-(2-methylpropyl)-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl]-1H-pyrazole-4-carboxamide), pymetrozine, pyrafluprole, pyrethrins, pyridaben, pyridalyl, pyrifluquinazone, pyriminostrobin (methyl(αE)-2-[[[2-[(2,4-dichlorophenyl)amino]-6- (trifluoromethyl)-4-pyrimidinyl]oxy]methyl]-α-(methoxymethylene)benzeneacetate), pyriprole, pyriproxyfen, rotenone, ryanodine, silafluofen, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulprofos, sulfoxaflor (N-[methyloxide[1-[6-(trifluoromethyl)-3-pyridinyl]ethyl]-λ, 4-sulfanylidene]cyanamide), tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, tetramethrin, tetramethylfluthrin ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl Insecticides such as methyl 2,2,3,3-tetramethylcyclopropanecarboxylate), tetraniliprole, thiacloprid, thiamethoxam, thiodicarb, thiosultap, thiosultap-sodium, thioxazafen (3-phenyl-5-(2-thienyl)-1,2,4-oxadiazole), tolfenpyrad, tralomethrin, triazamate, trichlorfon, triflumezopyrim (2,4-dioxo-1-(5-pyrimidinylmethyl)-3-[3-(trifluoromethyl)phenyl]-2H-pyrido[1,2-a]pyrimidinium inner salt), triflumuron, Bacillus thuringiensis delta-endotoxin, entomopathogenic bacteria, entomopathogenic viruses, and entomopathogenic fungi.

[0311] Of note are abamectin, acetamiprid, acrinathrin, afidopiropen, amitraz, avermectin, azadirachtin, benfuracarb, bensultap, bifenthrin, buprofezin, cadusafos, carbaryl, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, and gamma-cyhalothrin. lanthanide, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenitrothion, fenothiocarb, fenoxycarb, fenvalerate, fipronil, flometoquin, flonicamid, flubendiamide, flufenoxuron, flufen Noxystrobin, flufensulfone, flupiprole, flupyradifurone, fluvalinate, formetanate, fosthiazate, heptafluthrin, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, lufenuron, meperfluthrin, metaflumizone, methiodicarb, methomyl, methoprene, methoxyfenozide, metofluthrin, monofluorothrin, nitenpyram, nithiazine, novaluron, oxamyl, piflubumid, pymetrozine, Insecticides such as pyrethrins, pyridaben, pyridalyl, pyriminostrobin, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulfoxaflor, tebufenozide, tetramethrin, tetramethylfluthrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, triflumezopyrim, triflumuron, Bacillus thuringiensis delta-endotoxin, all strains of Bacillus thuringiensis, and all strains of nucleopolyhedrovirus.

[0312] In one embodiment, biological agents for admixture with the compounds of the present invention include entomopathogenic bacteria, such as Bacillus thuringiensis and encapsulated delta-endotoxin of Bacillus thuringiensis, e.g., MVP® and MVPII® bioinsecticides prepared by the CellCap® process (CellCap®, MVP®, and MVPII® are trademarks of Mycogen Corporation, Indianapolis, Indiana, USA); entomopathogenic fungi, such as green muscardine fungi; and entomopathogenic viruses (both naturally occurring and genetically modified), such as baculoviruses, nucleopolyhedroviruses (NPV), e.g., Helicoverpa zea nucleopolyhedrovirus (HzNPV), Anagrapha falcifera, and the like. falcifera nucleopolyhedrovirus (AfNPV); and granulosis viruses (GV), such as codling moth (Cydia pomonella) granulosis virus (CpGV).

[0313] Of particular note are such combinations in which the other invertebrate pest control active ingredient belongs to a different chemical class or has a different site of action than the compound of Formula 1. In certain instances, combinations with at least one other invertebrate pest control active ingredient having a similar control spectrum but a different site of action are particularly advantageous for resistance management. Thus, the compositions of the present invention can further comprise a biologically effective amount of at least one additional invertebrate pest control active ingredient having a similar control spectrum but belonging to a different chemical class or having a different site of action. These additional biologically active compounds or agents include acetylcholinesterase (AChE) inhibitors such as the carbamates methomyl, oxamyl, thiodicarb, triazamate, and the organophosphate chlorpyrifos; GABA-gated chloride channel antagonists such as the cyclodiene dieldrin and endosulfan, and the phenylpyrazoles ethiprole and fipronil; sodium channel modulators such as the pyrethroids bifluthrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, deltamethrin, dimefluthrin, esfenvalerate, metofluthrin, and profluthrin; nicotinic acetylcholine receptor (nAChR) agonists such as the neonicotinoids acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, and thiamethoxam, and sulfoxaflor; nicotinic acetylcholine receptor (nAChR) allosteric activators such as the spinosyns spinetoram and spinosad; chloride channel activators such as the avermectins abamectin and emamectin; juvenile hormone mimetics such as diofenolan, methoprene, fenoxycarb, and pyriproxyfen; selective homopteran feeding blockers such as pimetrizine and flonicamid; acarid growth inhibitors such as etoxazole; inhibitors of mitochondrial ATP synthase such as propargite; and uncouplers of oxidative phosphorylation via disruption of the proton gradient such as chlorfenapyr.Nicotinic acetylcholine receptor (nAChR) channel blockers such as the nereistoxin analog cartap; inhibitors of chitin biosynthesis such as the benzoylureas flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, and triflumuron, and buprofezin; dipteran molting disruptors such as cyromazine; ecdysone receptor agonists such as the diacylhydrazines methoxyfenozide and tebufenozide; octopamine receptor agonists such as amitraz; mitochondrial electron transport chain complex III inhibitors such as hydramethylnon; mitochondrial electron transport chain complex I inhibitors such as pyridaben; voltage-dependent sodium channel blockers such as indoxacarb; tetronic acid and tetramethylbenzylamine. inhibitors of acetyl-CoA carboxylase, such as the phosphates spirodiclofen, spiromesifen, and spirotetramat; mitochondrial electron transport chain complex II inhibitors, such as the β-ketonitriles cyenopyrafen and cyflumetofen; ryanodine receptor modulators, such as the anthranilic diamides chlorantraniliprole, cyantraniliprole, and cyantraniliprole, diamides, such as flubendiamide, and ryanodine; compounds with unknown or uncharacterized target sites involved in biological activity, such as azadirachtin, bifenazate, pyridalyl, pyrifluquinazone, and triflumezopyrim; microbial disruptors of insect midgut membranes, such as Bacillus thuringensis and the delta-endotoxins they produce, and Bacillus sphaericus; and biological agents, including nuclear polyhedrosis virus (NPV) and other naturally occurring or genetically modified insecticidal viruses. ;

[0314] Further examples of biologically active compounds or agents that may be combined with the compounds of the invention are acibenzolar-S-methyl, aldimorph, ametoctrazine, amisulbrom, anilazine, azaconazole, azoxystrobin, benalaxyl (including benalaxyl-M), benodanil, benomyl, benthiavalicarb (including benthiavalicarb-isopropyl), benzovindiflupyr, bethoxadine, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, boscalid, bromuconazole, bupirimate, buthiazol-1, benzophenone-1, benzophenone-2, benzophenone-3, benzophenone-4, benzophenone-5, benzophenone-6, benzophenone-7, benzophenone-8, benzophenone-9, benzophenone-11, benzophenone-12, benzophenone-13, benzophenone-14, benzophenone-15, benzophenone-16, benzophenone-17, benzophenone-18, benzophenone-19, benzophenone-20, benzophenone-21, benzophenone-22, benzophenone-23, benzophenone-24, benzophenone-25, benzophenone-26, benzophenone-27, benzophenone-28, ben...

Claims

1. Compounds of formula 1 (including all geometric and stereoisomers), N-oxides, and salts thereof, [Chemical 1] During the ceremony, X is O or S; Each A is independently CH, N, or CR １ and Each R １ are independently H, amino, cyano, halogen, nitro, C(S)NH ２ or R １ But C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ７ cycloalkyl, or C ４ ~C ８ cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R ６ optionally substituted with R １ is a phenyl or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, and each phenyl or heteroaromatic ring is selected from one or more R ６ optionally substituted with R １ But C ３ ~C ９ -trialkylsilyl, C(O)R ７ , C.R. ７ (=NO)R ７ , C(O)OR ７ , C(O)NR ７ R ８ , N.R. ７ R ８ , N.R. ８ C(O)R ７ , N.R. ８ C(O)OR ７ , OR ７ , NHC(O)NR ７ R ８ , N.R. ７ S(O)pR ９ , O.C.(O.)R ７ , OC(O)NR ７ R ８ , OC(O)OR ７ , S(O)pR ９ , SF ５ , S.O. ２ NR ７ R ８ , OS(O) ２ R ９ , or S (= NR １１ ) O ｐ R ９ or R １ are independently halogen, cyano, C １ ~C ３ Alkyl, C １ ~C ３ -haloalkyl, C １ ~C ３ -alkoxy, and C １ ~C ３ -haloalkoxy, or when a nitrogen atom is present, C(O)R ７ , C(O)OR ７ , C(O)NR ７ R ８ , S(O)pR ７ , or SO ２ NR ７ R ８ a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with R ２ But hydrogen, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ cycloalkyl, or C ４ ~C ７ cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R ６ optionally substituted with R ２ However, one or more R ６ C optionally substituted with and substituted by phenyl １ ~C ６ a 4- to 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from alkyl or carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 2 nitrogen atoms, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or heterocyclic ring contains one or more R ６ optionally substituted with R ２ But C(O)R ７ , C(O)OR ７ , N.R. ７ R ８ , OR ７ , S(O)pR ９ or SO ２ NR ７ R ８ and R ３ But C １ ~C ３ Alkyl or C １ ~C ３ haloalkyl; R ４ But hydrogen, cyano, halogen, nitro, C(S)NH ２ ,SCN,C. １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ７ cycloalkyl, or C4-C8 cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R ６ optionally substituted with R ４ But C(O)R ７ , C.R. ７ (=NO)R ７ , C(O)OR ７ , C(O)NR ７ R ８ , N.R. ７ R ８ , N.R. ８ C(O)R ７ , N.R. ８ C(O)OR ７ , OR ７ , S(O)pR ９ , S.O. ２ NR ７ R ８ , or NR １１ SO ２ NR ７ R ８ and R ５ But hydrogen, cyano, halogen, nitro, C(S)NH ２ ,SCN,C. １ ~C ６ -Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ７ cycloalkyl, or C ４ ~C ８ cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R ６ optionally substituted with R ５ But C(O)R ７ , C.R. ７ (=NO)R ８ , C(O)OR ７ , C(O)NR ７ R ８ , N.R. ７ R ８ , N.R. ８ C(O)R ７ , N.R. ８ C(O)OR ７ , N.R. １１ SO ２ NR ７ R ８ , OR ７ , S(O)pR ９ , or SO ２ NR ７ R ８ and Each R ６ are independently halogen, cyano, nitro, SF ５ , C(O)NH ２ , C(S)NH ２ , C １ ~C ３ Alkyl, C １ ~C ３ Haloalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ Haloalkoxy, C ３ ~C ７ Cycloalkyl, C ３ ~C ９ Trialkylsilyl, C(O)OR １０ , C(O)NR ７ R ８ , N.R. ７ R ８ , N.R. ８ C(O)R ７ , N.R. ８ C(O)OR ７ , OR ７ , NHC(O)NR ７ R ８ , N.R. ７ S(O)pR ９ , O.C.(O.)R ７ , OC(O)OR ７ , S(O)pR ９ , S.O. ２ NR ７ R ８ , or S(=NR)O ｐ R ７ and Each R ７ are independently hydrogen, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ３ ~C ６ Alkynyl, or C ３ ~C ７ cycloalkyl, or C ４ ~C ８ cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl, or cycloalkyl or cycloalkylalkyl is selected from one or more R １２ optionally substituted with R ７ is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R １２ optionally substituted with; Each R ８ are independently hydrogen, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyl, C ３ ~C ６ Alkenyloxy, C ２ ~C ６ Alkynyl, or C ３ ~C ６ alkynyloxy, wherein each alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy is selected from one or more R ６ optionally substituted with; R ７ and R ８ If is on N, then R ７ and R ８ is oxygen, S(O)p or NR ７ can form a 3 to 7 carbon ring optionally containing R ９ But independently, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, or C ３ ~C ７ cycloalkyl, and each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more R ６ optionally substituted with R ９ is phenyl or a 4-6 membered saturated, partially saturated, or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, and each phenyl or 4-6 membered heterocyclic ring is selected from one or more R ６ optionally substituted with; Each R １０ However, independently, H, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C ３ ~C ７ Cycloalkyl, C ３ ~C ７ Cycloalkyl-C １ ~C ３ -Alkyl, C １ ~C ３ Alkoxy-C １ ~C ３ - alkyl; Each R １１ are independently hydrogen, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ cycloalkyl, or C ４ ~C ７ cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R ６ optionally substituted with C(O)R ７ , C(O)OR ７ , or S(O)pR ７ and R １２ But halogen, hydroxy, cyano, nitro, SF ５ , C(O)NH ２ , C(S)NH ２ , C １ ~C ３ Alkyl, C １ ~C ３ Alkoxy, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ７ Cycloalkyl, C ４ ~C ８ cycloalkylalkyl, wherein each alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is optionally substituted with halogen or cyano; Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with 1 to 3 groups, and the thiazole is optionally substituted with 1 to 2 groups, which groups are selected from the group consisting of amino, cyano, halogen, nitro, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ７ cycloalkyl, or C ４ ~C ８ cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R ６ , C(O)R ７ , C.R. ７ (=NOR ８ ), C(O)OR ７ , C(O)NR ７ R ８ , C(S)NR ７ R ８ , OR ７ , S(O) ｐ R ９ , S.O. ２ NR ７ R ８ optionally substituted with NR ７ R ８ , N.R. ８ C(O)R ７ , N.R. ８ C(O)OR ７ , S(O)pR ７ , S.O. ２ NR ７ R ８ , or halogen, cyano, C １ ~C ３ Alkyl, C １ ~C ３ -haloalkyl, C １ ~C ３ -alkoxy, and C １ ~C ３ - a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms optionally substituted with 1 to 3 substituents independently selected from haloalkoxy and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, or halogen, cyano, C １ ~C ３ Alkyl, C １ ~C ３ -haloalkyl, C １ ~C ３ -alkoxy, and C １ ~C ３ -haloalkoxy, or when a nitrogen atom is present, C(O)R ７ , C(O)OR ７ , C(O)NR ７ R ８ , S(O)pR ７ , S.O. ２ NR ７ R ８ is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with n is 1, 2, or 3; A compound wherein p is 0, 1, or 2.

2. The compound of claim 1 , wherein X is O.

3. 2. The compound of claim 1, wherein X is S.

4. 2. The compound of claim 1, wherein A is CH.

5. A is N or CR １ The compound according to any one of claims 1 to 4,

6. X is O; A is CH; and R ３ The compound of claim 1 , wherein is Me.

7. R １ Amino, cyano, halogen, nitro, C(S)NH ２ or R １ But C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ７ cycloalkyl, or C ４ ~C ８ cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R ６ optionally substituted with R １ is a phenyl or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, and each phenyl or heteroaromatic ring is selected from one or more R ６ optionally substituted with R １ But C ３ ~C ９ -trialkylsilyl, C(O)R ７ , C.R. ７ (=NO)R ７ , C(O)OR ７ , C(O)NR ７ R ８ , N.R. ７ R ８ , NR8C(O)R7, NR8C(O)OR7, OR ７ , NHC(O)NR ７ R ８ , N.R. ７ S(O)pR ９ , O.C.(O.)R ７ , OC(O)NR ７ R ８ , OC(O)OR ７ , S(O)pR ９ , SF ５ , S.O. ２ NR ７ R ８ , OS(O) ２ R ９ , or S (= NR １１ ) O ｐ R ９ or R １ But halogen, cyano, C １ ~C ３ Alkyl, C １ ~C ３ -haloalkyl, C １ ~C ３ -alkoxy, and C １ ~C ３ -haloalkoxy, or when a nitrogen atom is present, C(O)R ７ , C(O)OR ７ , C(O)NR ７ R ８ , S(O)pR ７ , or SO ２ NR ７ R ８ 7. The compound of any one of claims 1 to 6, wherein R is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted with

8. R ２ But hydrogen, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ cycloalkyl, or C ４ ~C ７ cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R ６ optionally substituted with R ２ However, one or more R ６ C optionally substituted with and substituted with phenyl １ ~C ６ a 4- to 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from alkyl or carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 2 nitrogen atoms, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or heterocyclic ring contains one or more R ６ optionally replaced with R ２ But C(O)R ７ , C(O)OR ７ , N.R. ７ R ８ , OR ７ , S(O)pR ９ or SO ２ NR ７ R ８ The compound according to any one of claims 1 to 7,

9. R ２ But H, CH ２ The compound of claim 7, which is c-Pr or Me.

10. R ４ But hydrogen, cyano, halogen, nitro, C(S)NH ２ ,SCN,C. １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ７ cycloalkyl, or C4-C8 cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R ６ optionally substituted with R ４ But C(O)R ７ , C.R. ７ (=NO)R ７ , C(O)OR ７ , C(O)NR ７ R ８ , N.R. ７ R ８ , N.R. ８ C(O)R ７ , N.R. ８ C(O)OR ７ , OR ７ , S(O)pR ９ , S.O. ２ NR ７ R ８ , or NR １１ SO ２ NR ７ R ８ and R ５ But hydrogen, cyano, halogen, nitro, C(S)NH ２ ,SCN,C. １ ~C ６ -Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ７ cycloalkyl, or C ４ ~C ８ cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R ６ optionally substituted with R ５ But C(O)R ７ , C.R. ７ (=NO)R ８ , C(O)OR ７ , C(O)NR ７ R ８ , N.R. ７ R ８ , N.R. ８ C(O)R ７ , N.R. ８ C(O)OR ７ , N.R. １１ SO ２ NR ７ R ８ , OR ７ , S(O)pR ９ , or SO ２ NR ７ R ８ The compound according to any one of claims 1 to 9,

11. Q is pyridine or pyrimidine optionally substituted with 1 to 3 groups, and these groups are amino, cyano, halogen, nitro, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ７ cycloalkyl, or C ４ ~C ８ cycloalkylalkyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is selected from one or more R ６ , C(O)R ７ , C.R. ７ (=NOR ８ ), C(O)OR ７ , C(O)NR ７ R ８ , C(S)NR ７ R ８ , OR ７ , S(O) ｐ R ９ , S.O. ２ NR ７ R ８ optionally substituted with NR ７ R ８ , N.R. ８ C(O)R ７ , N.R. ８ C(O)OR ７ , S(O)pR ７ , S.O. ２ NR ７ R ８ , or halogen, cyano, C １ ~C ３ Alkyl, C １ ~C ３ -haloalkyl, C １ ~C ３ -alkoxy, and C １ ~C ３ - a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms optionally substituted with 1 to 3 substituents independently selected from haloalkoxy and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, or halogen, cyano, C １ ~C ３ Alkyl, C １ ~C ３ -haloalkyl, C １ ~C ３ -alkoxy, and C １ ~C ３ -haloalkoxy, or when a nitrogen atom is present, C(O)R ７ , C(O)OR ７ , C(O)NR ７ R ８ , S(O)pR ７ , S.O. ２ NR ７ R ８ 11. The compound of any one of claims 1 to 10, wherein the heterocyclic ring is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 4 nitrogen atoms, substituted by

12. 12. The compound of any one of claims 1 to 11, wherein Q is selected from Q-1, Q-2, Q-6, Q-7, Q-11, Q-13, Q-14, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, and Q-25.

13. X is O; A is CH; n is 2; Each R １ are independently Cl, F, or Br, or R １ However, one or more R ６ Me optionally substituted with R １ OMe, SF ３ , or OS(O) ２ R ９ and R ２ But hydrogen, C １ ~C ４ Alkyl, or C ４ ~C ６ cycloalkylalkyl, where each alkyl or cycloalkylalkyl is one R ６ optionally substituted with; R ４ is hydrogen, cyano, halogen, nitro, or C １ ~C ３ alkyl, wherein the alkyl is one or more R ６ optionally substituted with R ４ But NR ７ R ８ , N.R. ８ C(O)R ７ , OR ７ , or S(O)pR ９ and R ５ is hydrogen, cyano, halogen, nitro, or C １ ~C ３ -alkyl, each alkyl or cycloalkyl being selected from one or more R ６ optionally substituted with R ５ But OR ７ , N.R. ７ R ８ , N.R. ８ C(O)R ７ , N.R. ８ C(O)OR ７ , S(O)pR ７ , or SO ２ NR ７ R ８ 2. The compound of claim 1, wherein:

14. R ４ and R ５ and are not both hydrogen.

15. X is O; A is N or CR １ and R １ is Cl, F, or Br, or R １ However, one or more R ６ Me optionally substituted with １ But OMe, SF ３ , or OS(O) ２ R ９ and R ２ But hydrogen, C １ ~C ４ Alkyl, or C ４ ~C ６ cycloalkylalkyl, where each alkyl or cycloalkylalkyl is one R ６ optionally replaced with R ２ But C(O)R ７ or C(O)OR ７ and R ４ is hydrogen, cyano, halogen, nitro, or C １ ~C ３ alkyl, wherein the alkyl is one or more R ６ 2. The compound of claim 1, optionally substituted with:

16. The compound is N-[1-[3-amino-4-cyano-1-(5-cyano-2-pyridinyl)-1H-pyrazol-5-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide, N-[1-[4-cyano-1-(5-cyano-2-pyridinyl)-3-(methylamino)-1H-pyrazol-5-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide, N-methyl-N-(1-(4-nitro-1-(pyrimidin-2-yl)-1H-pyrazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide, N-(1-(4-cyano-1-(5-cyanopyridin-2-yl)-1H-pyrazol-5-yl)ethyl)-N-methyl-3,5-bis(trifluoromethyl)benzamide, 3-chloro-N-(1-(4-cyano-1-(5-cyanopyridin-2-yl)-1H-pyrazol-5-yl)ethyl)-N-methyl-5-(trifluoromethyl)benzamide, N-(1-(4-cyano-1-(pyrimidin-2-yl)-1H-pyrazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide, N-[1-[3-amino-4-cyano-1-[5-(4-morpholinylcarbonyl)-2-pyridinyl]-1H-pyrazol-5-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide, N,N-dimethyl-6-(5-(1-(N-methyl-3,5-bis(trifluoromethyl)benzamido)ethyl)-4-(methylsulfonyl)-1H-pyrazol-1-yl)pyrimidine-4-carboxamide N-(1-(4-cyano-3-methoxy-1-(pyrimidin-2-yl)-1H-pyrazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide, N-methyl-N-(1-(4-(methylsulfonyl)-1-(pyrazin-2-yl)-1H-pyrazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide, N-(1-(4-nitro-1-(pyrimidin-2-yl)-1H-pyrazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide, and N-methyl-N-(1-(4-(methylsulfonyl)-1-(6-(trifluoromethyl)pyrimidin-4-yl)-1H-pyrazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide 2. The compound of claim 1 selected from the group consisting of:

17. 17. A composition comprising a compound according to any one of claims 1 to 16 and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, said composition optionally further comprising at least one additional biologically active compound or drug.

18. The at least one additional biologically active compound or agent is abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, afidopiropen, amidoflumet, amitraz, avermectin, azadirachtin, azinphos-methyl, bendiocarb, benfuracarb, bensultap, bifenthrin, bifenazate, bistrifluron, borate, bromantraniliprole, buprofezin, carbaryl, carbofuran, cartap, chlorantraniliprole, chlorfenapyr, chlorfluazuron, chloramphenicol ... Prallethrin, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezine, clothianidin, cyantraniliprole, cyclaniliprole, cyclobutrifluram, cycloprothrin, cycloxapride, cetopyrafen, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalodiamide, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyprofuranilide, cyromazine, deltamethrin, diafenthiuron , diazinon, dichlorantraniliprole, dieldrin, diflobidazin, diflubenzuron, dimefluthrin, dimehypo, dimethoate, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenazaquin, fenbutatin oxide, fenitrothion, phenmezodithiaz, fenothiocarb, fenoxycarb, fenpyroximate, fenpropathrin, fenvalerate, fipronil, flometoquin, flonicamid, flu Acripyrim, fluazaindolizine, flubendiamide, fluchlordiniliprole, flucythrinate, flufenerim, flufenoxuron, flufenoxystrobin, fluensulfone, fluhexafon, flupentiofenox, fluopyram, flupirimine, flupyradifurone, fluvalinate, tau-fluvalinate, fluxametamide, fonofos, formetanate, fosthiazate, halofenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, hydroprene, imidacloprid,Indazapiroxameth (N-(1-methylcyclopropyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide), indoxacarb, insecticidal soap, isofenphos, isocycloceram, kappa-tefluthrin, kinoprene, lufenuron, malathion, mepafluthrin, metaflumizone, metaldehyde, methamidophos, methidathion, methiocarb, methomyl, methoprene, methoxychlor, methoxyfenozide, metofluthrin, monocrotophos, monofluorothrin, nicofluprole, nicotine, N-[1,1-dimethyl-2-(2-methyl-4-pyridinyl)-2H-indazole-4-carboxamide], -(methylthio)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1,1-dimethyl-2-(methylsulfinyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1,1-dimethyl-2-(methylsulfonyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1,1-dimethyl-2-(methylsulfonyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-(1-methylcyclopropyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1-(difluoromethyl)-2-(pyridinyl)ethyl]- [3-(3-methyl)cyclopropyl]-2-(3-pyridinyl)-2H-indazole-4-carboxamide, nitenpyram, nithiazine, novaluron, noviflumuron, oxamyl, oxazosulfil, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, propargite, protrifenbut, piflubumid, pymetrozine, pyrafluprole, pyrethrins (pyrethrum), pyridaben, pyridalyl, pyrifluquinazon, pyrimidifen, Riminostrobin, pyriprole, pyriproxyfen, rotenone, ryanodine, silafluofen, spidoxamat, spinetoram, spinosad, spirobudifen, spirodiclofen, spiromesifen, spirotetramat, sulprofos, sulfoxaflor, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, kappa-tefluthrin, terbufos, tetrachlorantraniliprole, tetrachlorvinphos, tetramethrin, tetramethylfluthrin, tetraniliprole, thiacloprid, thiamethoxam, thiodicarb,16. The composition of claim 15, wherein the active ingredient is selected from the group consisting of thiosultap, thiosultap sodium, thiolantraniliprole, thioxazaphen, tolfenpyrad, tralomethrin, triazamate, trichlorfon, trifluenfuronate, triflumezopyrim, triflumuron, cyclopyrazoflor, Bacillus sphaericus, Bacillus thuringiensis delta-endotoxin, entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi, plant essences including synthetic extracts and unrefined oils, and RNA interference-mediated target inhibitors.

19. 17. A method for controlling and combating invertebrate pests, comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of any one of claims 1 to 16.

20. 17. Treated seeds comprising a compound according to any one of claims 1 to 16 in an amount of about 0.0001 to 1% by weight of the seeds before treatment.

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