Azole compounds for controlling and eradicating invertebrate pests - Patent Application 20070122999

Abstract

Disclosed are compounds of formula I, including all geometric and stereoisomers, N-oxides and salts thereof, wherein A, R 2 , R 4 , R 5 , L, and Q are as defined in this disclosure. Also disclosed are compositions containing the compounds of Formula 1, and methods for controlling and combating invertebrate pests comprising contacting the invertebrate pests or their environment with a biologically effective amount of a compound or composition of the present disclosure. [Formula 1] TIFF2025542212000089.tif22170

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of U.S. Provisional Patent Application No. 63 / 433,847, filed December 20, 2022.

[0002] The present disclosure relates to certain azole compounds, their N-oxides, salts, and compositions suitable for agricultural or non-agricultural use, and methods of using them to control and eradicate 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. Invertebrate pest damage to growing and stored crops can significantly reduce productivity, resulting in increased costs to consumers. Controlling invertebrate pests is also important in forestry, greenhouse crops, ornamentals, seedling crops, stored food and fiber products, livestock, households, turf, wood products, and public and animal 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 site of action. Summary of the Invention [Means for solving the problem]

[0004] The present disclosure relates to compounds of Formula 1 (including all geometric and stereoisomers), their N-oxides and salts, and compositions containing them, and their use for controlling and combating invertebrate pests: [ka] During the ceremony, L is [ka] and the bond projecting to the left in each of L1, L2, L3, L4, and L5 is the bond projecting to the right in each of L1, L2, L4, and L5 is bonded to Q, and the bond projecting downward in L3 is bonded to Q; T is CHR, O, S, CO, or CS; R is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 1a and R 1b are each individually H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyl, or C1-C6 haloalkoxyl; p is 1, 2, 3, or 4; A is N or CR 3 and; R 2 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 3 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 4 is a 5-6 membered heterocyclic ring, each ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N atoms, wherein up to 2 ring members are independently selected from C(=O), C(=S), S(=O), and S(=O)2, and each ring optionally contains R v and r is the number of substituents; Each R vare independently H, cyano, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 cyanoalkyl, C1-C6 hydroxyalkyl, C4-C6 10 Alkylcycloalkyl, C4-C 10 Cycloalkylalkyl, C3-C6 cycloalkenyl, C3-C6 halocycloalkenyl, C2-C6 alkoxyalkyl, C4-C 10 Cycloalkoxyalkyl, C3-C 10 Alkoxyalkoxyalkyl, C2-C6 alkylthioalkyl, C2-C6 alkylsulfinylalkyl, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C 10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkoxyalkoxy, C2-C6 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C6 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C6 cycloalkylsulfonyl, C1-C6 alkylamino, C2-C6 dialkylamino, C1-C6 haloalkylamino, C2-C6 halodialkylamino, or C3-C6 cycloalkylamino; r is 1, 2, 3, 4, or 5; R 5 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; Q is a 5- or 6-membered aromatic ring containing carbon atoms and ring members selected from up to one oxygen atom, one sulfur atom, and two nitrogen atoms, each ring optionally containing, on a carbon atom ring member, R wand is substituted with up to five substituents independently selected from: w together form a 5- or 6-membered ring, for example, -OCF2O-, -OCH2O-, -OCF2S-, -OCH2CH2-, OCF2CF2O-, -OCR 5 =N-, -SCR 5 =N-, -CH=CR 5 -CH=CH- or -CH=N-CR 5 =CH- can be formed; R w are independently H, cyano, halogen, SF5, SCl, SO2Cl, SO2F, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 cyanoalkyl, C1-C6 hydroxyalkyl, C4-C6 10 Alkylcycloalkyl, C4-C 10 Cycloalkylalkyl, C3-C6 cycloalkenyl, C3-C6 halocycloalkenyl, C2-C6 alkoxyalkyl, C4-C 10 Cycloalkoxyalkyl, C3-C 10 Alkoxyalkoxyalkyl, C2-C6 alkylthioalkyl, C2-C6 alkylsulfinylalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C 10cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkoxyalkoxy, C2-C6 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C6 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C6 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C6 cycloalkylsulfonyl, C1-C6 alkylamino, C2-C6 dialkylamino, C1-C6 haloalkylamino, C2-C6 halodialkylamino, or C3-C6 cycloalkylamino; s is 1, 2, 3, 4, or 5.

[0005] The present disclosure also provides a composition comprising a compound of Formula 1, an N-oxide or salt thereof, 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 disclosure also provides a composition for controlling and combating invertebrate pests comprising a compound of Formula 1, an N-oxide or salt thereof, and at least one additional ingredient 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.

[0006] The present disclosure also 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, its N-oxide or salt (e.g., as a composition described herein). The present disclosure also relates to such methods, wherein the invertebrate pest or its environment is contacted with a composition comprising a biologically effective amount of a compound of Formula 1, its N-oxide or salt, and at least one additional component 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 biologically active compound or agent.

[0007] The present disclosure also provides a method for controlling and eradicating invertebrate pests, comprising contacting the invertebrate pests or their environment with a biologically effective amount of any of the above compositions, wherein the environment is a plant.

[0008] The present disclosure also provides a method for controlling and eliminating invertebrate pests, comprising contacting the invertebrate pest or its environment with a biologically effective amount of any of the above compositions, wherein the environment is an animal.

[0009] The present disclosure also provides a method for controlling and eradicating invertebrate pests, comprising contacting the invertebrate pest or its environment with a biologically effective amount of any of the above compositions, wherein the environment is a seed.

[0010] The present disclosure 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, its N-oxide, or a salt (e.g., as a composition described herein). The present disclosure also relates to treated seeds (i.e., seeds contacted with a compound of Formula 1).

[0011] The present disclosure also provides a method for increasing the vigor of a crop plant, the method comprising contacting the crop plant, a seed from which the crop plant grows, or the location of the crop plant (e.g., growing medium) with a biologically effective amount of a compound of Formula 1 (e.g., as a composition described herein).

[0012] The present disclosure further provides a method for protecting an animal from an invertebrate parasitic pest, comprising administering to the animal a parasiticidally effective amount of a compound of Formula 1, its N-oxide, or salt (e.g., as a composition described herein). The present disclosure also provides the use of a compound of Formula 1, its N-oxide, or salt (e.g., as a composition described herein) in protecting an animal from an invertebrate pest. DETAILED DESCRIPTION OF THE INVENTION

[0013] As used herein, the terms "comprising," "including," "having," "containing," "characterized by," or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitations expressly stated. For example, a composition, mixture, process, or method that includes a list of elements is not necessarily limited to only those elements and may include other elements that are not expressly listed or that are inherent in such composition, mixture, process, or method.

[0014] The transitional phrase "consisting of" excludes any unspecified element, step, or ingredient. When in a claim, such a transitional phrase closes the claim to the inclusion of materials other than those recited, apart from impurities normally associated with the recited materials. When the phrase "consisting of" appears in a clause in the body of a claim rather than immediately before the preamble, it limits only the elements set forth in that clause and does not exclude other elements from the claim as a whole.

[0015] The transitional phrase "consisting essentially of" is used to define compositions or methods that include materials, steps, features, ingredients, or elements in addition to those literally disclosed, provided that these additional materials, steps, features, ingredients, or elements do not materially affect the basic and novel characteristics of the claimed disclosure. The term "consisting essentially of" occupies a middle ground between "comprising" and "consisting of."

[0016] It should be readily understood that where applicants define an embodiment or portion thereof by open-ended terms such as "comprising," the statement should be construed as also describing those embodiments using the terms "consisting essentially of" or "consisting of" (unless stated to the contrary).

[0017] Further, unless expressly stated to the contrary, "or" refers to an inclusive "or" and not an exclusive "or." For example, condition A or condition B can be 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 A and B are both true (or exist).

[0018] Also, the indefinite articles "a" and "an" preceding an element or component of the present disclosure 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 the singular form of that element or component also includes the plural, unless it is clear that the number is intended to be singular.

[0019] The term "invertebrate pests" referred to in this disclosure includes arthropods, gastropods, nematodes, and parasitic helminths that are economically important as pests. The term "arthropods" includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs, and the class Columbidae. The term "gastropods" includes snails, slugs, and other Stylommatophora. The term "nematodes" includes members of the phylum Nematoda, e.g., phytophagous nematodes and animal-parasitic helminths Nematoda. The term "parasitic helminths" includes all parasites, e.g., roundworms (Nematoda), heartworms (Nematoda, Dactylostoma), trematodes (Platyhelminthes, Trematoda), thorny headworms (Antoxycephala), and cestodes (Platyhelminthes, Cestoda).

[0020] 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.

[0021] The term "agronomic" 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 vegetable crops), fruit vegetables (e.g., tomatoes, peppers, eggplant, brassicas, 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).

[0022] The term "non-agricultural" refers to non-agricultural crops such as horticultural crops (e.g., greenhouse plants, nursery plants, or ornamental plants that are not grown in fields), 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, public health (i.e., humans) and animal health (e.g., domesticated animals, e.g., pets, livestock, and non-domesticated animals such as poultry, wildlife) uses.

[0023] The term "crop vigor" refers to the rate of growth or biomass accumulation of a crop plant. "Increased vigor" refers to increased growth or biomass accumulation in a crop plant compared to an untreated control crop plant. The term "crop yield" refers to the return of crop material, both in quantity and quality, obtained after harvesting a crop plant. "Increased crop yield" refers to an increase in crop yield compared to an untreated control crop plant.

[0024] 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 when applied to (i.e., contacted with) the invertebrate pest to be controlled or its environment, or to a plant, a seed from which the plant grows, or the locus of the plant (e.g., growing medium) to protect the plant from damage by the invertebrate pest or for other desired effect (e.g., increased plant vigor).

[0025] Nonagronomic uses include protecting animals from invertebrate parasitic pests by administering a parasiticidally effective (i.e., biologically effective) amount of a compound of the present disclosure to the animal to be protected, typically in the form of a composition formulated for veterinary use. The terms "parasiticidally" and "parasitically," as referred to in this disclosure and claims, refer to an observable effect on an invertebrate parasitic pest to achieve protection of the animal from the pest. A parasiticidal effect typically relates to reducing the occurrence or activity of the target invertebrate parasitic pest. Such effects on pests include necrosis, death, retarded development, reduced motility or ability to persist on or within the host animal, reduced feeding, and inhibited reproduction. These effects on invertebrate parasitic pests achieve control (including prevention, reduction, or elimination) of parasitic infestation or infection in the animal.

[0026] In the preceding description, the term "alkyl," whether used alone or in compound language such as "alkylthio" or "haloalkyl," includes straight-chain or branched alkyls, such as methyl, ethyl, n-propyl, i-propyl, or the various butyl, pentyl, or hexyl isomers. "Alkenyl" includes straight-chain or branched alkenes, such as ethenyl, 1-propenyl, 2-propenyl, and the various butenyl, pentenyl, and hexenyl isomers. "Alkenyl" also includes polyenes, such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes straight-chain or branched alkynes, such as ethynyl, 1-propynyl, 2-propynyl, and the various butynyl, pentynyl, and hexynyl isomers. "Alkynyl" can also include moieties composed of multiple triple bonds, such as 2,5-hexadiynyl. "Alkylene" refers to a straight-chain or branched alkanediyl. Examples of "alkylene" include CH2, CH2CH2, CH(CH3), CH2CH2CH2, CH2CH(CH3), and the various butylene isomers. "Alkenylene" refers to a straight-chain or branched alkenediyl containing one olefinic bond. Examples of "alkenylene" include CH=CH, CH2CH=CH, CH=C(CH3), and the various butenylene isomers. "Alkynylene" refers to a straight-chain or branched alkynediyl containing one triple bond. Examples of "alkynylene" include C≡C, CH2C≡C, C≡CCH2, and the various butynylene isomers.

[0027] "Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy, and the various butoxy, pentoxy, and hexyloxy isomers. "Alkoxyalkyl" indicates alkoxy substitution on alkyl. Examples of "alkoxyalkyl" include CHOCH, CHOCHCH, CHCHOCH, CHCHCHOCH, CHCHCHCHOCH, and CHCHOCHCH. "Alkoxyalkoxy" indicates alkoxy substitution on alkoxy. "Alkenyloxy" includes straight-chain or branched alkenyloxy moieties. Examples of "alkenyloxy" include HC=CHCHO, (CH)C=CHCHO, (CH)CH=CHCHO, (CH)CH=C(CH)CHO, and CH=CHCHCHO. "Alkynyloxy" includes straight-chain or branched alkynyloxy moieties. Examples of "alkynyloxy" include HC=CCHO, CHC≡CCHO, and CHC≡CCHCHO. "Alkylthio" includes branched or straight-chain alkylthio moieties, such as methylthio, ethylthio, and the various propylthio, butylthio, pentylthio, and hexylthio isomers. "Alkylsulfinyl" includes both enantiomers of alkylsulfinyl groups. Examples of "alkylsulfinyl" include CHS(O)-, CHCHS(O)-, CHCHCHS(O)-, (CH)CHS(O)-, and the various butylsulfinyl, pentylsulfinyl, and hexylsulfinyl isomers. Examples of "alkylsulfonyl" include CH3S(O)2-, CH3CH2S(O)2-, CH3CH2CH2S(O)2-, (CH3)2CHS(O)2-, and the various butylsulfonyl, pentylsulfonyl, and hexylsulfonyl isomers. "Alkylthioalkyl" denotes alkylthio substitution on alkyl. Examples of "alkylthioalkyl" include CH3SCH2, CH3SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2, and CH3CH2SCH2CH2. "Alkylthioalkoxy" denotes alkylthio substitution on alkoxy."Alkyldithio" refers to a branched or straight-chain alkyldithio moiety. Examples of "alkyldithio" include CH3SS-, CH3CH2SS-, CH3CH2CH2SS-, (CH3)2CHSS-, and the various butyldithio and pentyldithio isomers. "Cyanoalkyl" refers to an alkyl group substituted with one cyano group. Examples of "cyanoalkyl" include NCCH2, NCCH2CH2, and CH3CH(CN)CH2. "Alkylamino," "dialkylamino," "alkenylthio," "alkenylsulfinyl," "alkenylsulfonyl," "alkynylthio," "alkynylsulfinyl," and "alkynylsulfonyl," etc., are defined analogously to the previous examples.

[0028] Examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The term "alkylcycloalkyl" indicates alkyl substitution on a cycloalkyl moiety, and examples include ethylcyclopropyl, i-propylcyclobutyl, 3-methylcyclopentyl, and 4-methylcyclohexyl. The term "cycloalkylalkyl" indicates cycloalkyl substitution on an alkyl moiety. Examples of "cycloalkylalkyl" include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups. The term "cycloalkoxy" refers to a cycloalkyl linked through an oxygen atom, such as cyclopentyloxy and cyclohexyloxy. "Cycloalkylalkoxy" refers to a cycloalkylalkyl linked to an alkyl chain through an oxygen atom. Examples of "cycloalkylalkoxy" include cyclopropylmethoxy, cyclopentylethoxy, and other cycloalkyl moieties bonded to straight-chain or branched alkoxy groups. "Cyanocycloalkyl" refers to a cycloalkyl group substituted with a cyano group. Examples of "cyanocycloalkyl" include 4-cyanocyclohexyl and 3-cyanocyclopentyl. "Cycloalkenyl" includes, for example, cyclopentenyl and cyclohexenyl groups, as well as groups with multiple double bonds, such as 1,3- and 1,4-cyclohexadienyl.

[0029] 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," the 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-, CF3CH 2-and CF3CCl2-. The terms "halocycloalkyl," "haloalkoxy," "haloalkylthio," "haloalkenyl," and "haloalkynyl," etc., are defined analogously to the term "haloalkyl." Examples of "haloalkoxy" include CFO-, CC13CHO-, HCF2CH2CHO-, and CF3CHO-. Examples of "haloalkylthio" include CCl3S-, CF3S-, CC13CH2S-, and ClCH2CH2CH2S-. Examples of "haloalkylsulfinyl" include CF3S(O)-, CC13S(O)-, CF3CH2S(O)-, and CF3CF2S(O)-. Examples of "haloalkylsulfonyl" include CF3S(O)-, CC13S(O)-, CF3CH2S(O)-, and CF3CF2S(O)-. Examples of "haloalkenyl" include (Cl)C=CHCH-, and CFCHCH=CHCH-. Examples of "haloalkynyl" include HC≡CCHCl-, CFC≡C-, CClC≡C-, and FCHC≡CCH-. Examples of "haloalkoxyalkoxy" include CFOCHO-, ClCHCHOCHCHO-, ClCCHOCHO-, and branched alkyl derivatives.

[0030] "Alkylcarbonyl" refers to a straight-chain or branched alkyl moiety attached to a C(=O) moiety. Examples of "alkylcarbonyl" include CHC(=O)-, CHCHCHC(=O)-, and (CH)CHC(=O)-. Examples of "alkoxycarbonyl" include CHOC(=O)-, CHCHOC(=O)-, CHCHCHOC(=O)-, (CH)CHOC(=O)-, and the various butoxy- or pentoxycarbonyl isomers.

[0031] 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. "CHO" means formyl.

[0032] R 4 But R v When the heterocyclic ring is a 5- to 6-membered ring substituted with up to five substituents independently selected from v can be attached to the remainder of the compound of Formula 1 through any available ring member of the heterocycle.

[0033] Q is R w When the substituent R is a 6-membered aromatic ring substituted with up to five substituents independently selected from w may be attached to the remainder of the compound of Formula 1 through any available ring member of the six-membered aromatic ring.

[0034] The total number of carbon atoms in a substituent is indicated by the prefix "Ci-Cj," where i and j are numbers from 1 to 10. For example, C1-C4 alkylsulfonyl refers to methylsulfonyl through butylsulfonyl; C2 alkoxyalkyl refers to CHOCH-; C3 alkoxyalkyl refers to, for example, CHCH(OCH3)-, CHOCHCH-, or CHCHOCH-; and C4 alkoxyalkyl refers to the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples of which include CHCHCHOCH- and CHCHOCHCH-.

[0035] When a compound is substituted with a substituent having a subscript indicating that the number may be more than one, said substituent (if more than one) may be selected from a defined group of substituents, e.g., [(R v ) r] (r is 1, 2, 3, 4, or 5) and [(R w ) s ] (where s is 1, 2, 3, 4, or 5). A group may be a substituent that may be hydrogen, such as R v or R w and then this substituent is 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.

[0036] Unless otherwise specified, a "ring" (e.g., substituent R 4 ) is carbocyclic or heterocyclic. The term "ring member" refers to atoms or other moieties that form the backbone of the ring (e.g., C(=O), C(=S), S(O), or S(O)2).

[0037] The term "carbocyclic ring" or "carbocycle" refers to a ring in which the atoms forming the ring backbone are selected exclusively from carbon. The term "heterocyclic ring" or "heterocycle" refers to a ring in which at least one atom forming the ring backbone is not carbon, e.g., nitrogen, oxygen, or sulfur. Typically, a heterocyclic ring contains up to four nitrogens, up to two oxygens, and up to two sulfurs. Unless otherwise specified, a carbocyclic or heterocyclic ring may be saturated or unsaturated. "Saturated" refers to a ring having a backbone made up of atoms connected to each other by single bonds, and unless otherwise specified, the remaining valences are occupied by hydrogen atoms. Unless otherwise specified, an "unsaturated ring" may be partially unsaturated or fully unsaturated. The expression "fully unsaturated ring" means a ring of atoms in which the bonds between atoms in the ring are single or double bonds according to valence bond law, and further, the bonds between atoms in the ring include as many double bonds as possible without cumulative double bonds (i.e., no C=C=C or C=C=N). The term "partially unsaturated ring" refers to a ring that includes at least one ring member connected to an adjacent ring member via a double bond, and that conceptually potentially accommodates several non-cumulative double bonds between adjacent ring members (i.e., its fully unsaturated counterpart) beyond the number of double bonds present (i.e., its partially unsaturated form).

[0038] Unless otherwise specified, the heterocycle may be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

[0039] "Aromatic" indicates that each ring atom has a p-orbital that is essentially coplanar and perpendicular to the plane of the ring, where (4n+2) π electrons (n ​​is a positive integer) are associated with the ring according to Hückel's rule. When a fully unsaturated carbocyclic ring satisfies Hückel's rule, the ring is also called an "aromatic ring" or "aromatic carbocyclic ring." When a fully unsaturated heterocyclic ring satisfies Hückel's rule, the ring is also called an "aromatic heterocyclic ring" or "aromatic heterocyclic ring."

[0040] The term "optionally substituted" in reference to a heterocycle refers to a group that is unsubstituted or has at least one non-hydrogen substituent that does not abolish the biological activity retained by the unsubstituted analog. As used herein, the following definitions shall apply unless otherwise specified. The term "optionally substituted" is used synonymously with the phrase "substituted or unsubstituted" or the term "(un)substituted." Unless otherwise specified, an optionally substituted group may have a substituent at each substitutable position of the group, and each substitution is independent of the other.

[0041] R 4 When is a 5- or 6-membered nitrogen-containing heterocycle, it may be attached to the remainder of Formula 1 through any available carbon or nitrogen ring atom, unless otherwise specified.

[0042] As mentioned above, R 4 may be a 5- or 6-membered heterocyclic ring which may be saturated or unsaturated and optionally substituted with one or more substituents selected from the group of substituents defined in the Summary of the Invention. Examples of 5- or 6-membered unsaturated aromatic heterocyclic rings optionally substituted with one or more substituents include rings U-2 to U-61 in Appendix 1, where R v is any substituent defined in the Summary of the Invention, and r is an integer from 1 to 4 limited by the number of available positions on each U group. U-29, U-30, U-36, U-37, U-38, U-39, U-40, U-41, U-42, and U-43 have only one available position, so for these U groups, r is limited to the integer 1, and R v is H and r is 1 means that the U group is unsubstituted and the hydrogen is (R v ) r This means that the molecule is present at the position indicated by

[0043] Appendix 1 [ka] [ka] [ka]

[0044] R 4 It should be noted that when is a 5- or 6-membered saturated or unsaturated non-aromatic heterocycle optionally substituted with one or more substituents selected from the group of substituents defined in the Summary of the Invention, one or two carbon ring members of the heterocycle may optionally be in the oxidized form of a carbonyl moiety.

[0045] Examples of 5- or 6-membered saturated or non-aromatic unsaturated heterocyclic rings include rings G-1 to G-35 shown in Appendix 2. Note that when the point of attachment on the G group is shown as floating, the G group can be attached to the remainder of Formula 1 through any available carbon or nitrogen of the G group by substitution of a hydrogen atom. v may be attached to any available carbon or nitrogen by replacing a hydrogen atom. For these G rings, s is typically an integer from 1 to 5, limited by the number of available positions on each G group.

[0046] R 4 When G contains a ring selected from G-28 to G-35, G 2 Note that G is selected from O, S, or N. 2 is N, the nitrogen atom must have its valence adjusted to R as defined in the Summary of the Invention. w Note that this can be completed by substitution with a substituent corresponding to:

[0047] Appendix 2 [ka]

[0048] R v Note that although groups are shown in structures U-2 through U-61, they do not have to be present as they are optional substituents.v Note that if is H when attached to an atom, this is the same as if said atom were unsubstituted. Nitrogen atoms that require substitution to satisfy valence are H or R v (R v ) r If the connection point between and the U-ring is shown as floating, then (R v ) r Note that R may be attached to any available carbon or nitrogen atom of the U ring. Note that if the point of attachment on the U ring is shown as floating, the U group may be attached to the remainder of Formula 1 through any available carbon or nitrogen atom of the U group by replacement of a hydrogen atom. Some U rings may have fewer than four R v Note that only groups (e.g., U-2 to U-5, U-7 to U-49, and U-52 to U-61) can be substituted.

[0049] A wide variety of synthetic methods are known in the art that allow the preparation of aromatic and non-aromatic heterocycles and ring systems. For detailed reviews, see the 8-volume set of Comprehensive Heterocyclic Chemistry (A.R. Katrittzky and C.W. Rees, editors-in-chief, Pergamon Press, Oxford, 1984) and the 12-volume set of Comprehensive Heterocyclic Chemistry II (A.R. Katrittzky, C.W. Rees, and E.F.V. Scriven, editors-in-chief, Pergamon Press, Oxford, 1996).

[0050] The compounds of the present disclosure can exist as one or more stereoisomers. Stereoisomers are isomers with identical constitution but differing spatial arrangement of atoms, including enantiomers, diastereomers, cis-trans isomers (also known as geometric isomers), and atropisomers. Atropisomers result from restricted rotation around a single bond, and the rotational barrier is high enough to allow for the isolation of isomeric species. As will be appreciated by those skilled in the art, one stereoisomer may exhibit greater reactivity and / or beneficial effects when enriched or separated from other stereoisomers. Additionally, those skilled in the art will recognize methods for separating, enriching, and / or selectively preparing 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.

[0051] The compounds of the present disclosure can exist as a mixture of stereoisomers or as individual stereoisomers. Formula 1 can contain one, two, or more than two chiral centers. For example, some possible isomers or enantiomers of Formula 1 are shown below as Formula 1a: 1a , Equation 1a 1b , Equation 1a 2a , Equation 1a 2b , Equation 1a 2c , Equation 1a 2d , Equation 1a 3a , Equation 1a 3b , Equation 1a 3c , and Formula 1a 3d Similarly, other chiral centers may be represented as, for example, R 4 It can be considered as follows. [ka] [ka]

[0052] The depictions of molecules drawn herein follow standard conventions for indicating stereochemistry. To indicate three-dimensional configuration, bonds that rise out of the plane of the drawing toward the viewer are represented by a solid wedge, with the wider end of the wedge attached to an atom that rises out of the plane of the drawing toward the viewer. Bonds that point down the plane of the drawing and away from the viewer are represented by a dashed wedge, with the wider end of the wedge attached to an atom that is further away from the viewer. A wavy bond indicates that the stereochemistry of the bond is unknown.

[0053] The compounds of the present disclosure can exist as stereoisomers due to the 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.

[0054] The compounds of Formula 1 may contain additional chiral centers. For example, substituents and other molecular components, such as R 4 may themselves contain chiral centers. The present disclosure also includes racemic mixtures enriched at these additional chiral centers and having a substantially pure stereoconfiguration.

[0055] The compounds of the present disclosure may exist as one or more conformers due to restricted rotation around any bond in Formula 1. The present disclosure includes mixtures of conformers. As one skilled in the art will recognize, not all nitrogen-containing heterocycles can form N-oxides because the nitrogen requires an available lone pair of electrons to be oxidized to the oxide. Those skilled in the art will be familiar with nitrogen-containing heterocycles capable of forming N-oxides. Those skilled in the art will also be familiar with the ability of tertiary amines to form N-oxides. Synthetic methods for preparing N-oxides of heterocycles and tertiary amines are well known to those skilled in the art, including oxidation of heterocycles and tertiary amines with peroxyacids such as peracetic acid and 3-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane.These methods for preparing N-oxides have been widely described and reviewed in the literature, for example: T. L. Gilchrist, Comprehensive Organic Synthesis, vol. 7, pp. 748-750 (S.V. Ley, Ed., Pergamon Press); M. Tisler and B. Stanovnik, Comprehensive Heterocyclic Chemistry, vol. 3, pp. 18-20, A.J. Boulton and A. McKillop, Eds., Pergamon Press; M.R. Grimmett and B.R.T. Keene, Advances in Heterocyclic Chemistry, vol. 43, pp. 149-161, A.R.Katrittzky, Ed., Academic Press; M. Tisler and B. Stanovnik, Advances in Heterocyclic Chemistry, vol. 9, pp. 285-291, A.R.Katrittzky and A.J.Boulton, Eds., Academic Press; and G.W.H. Cheeseman and See ESGWerstiuk, Advances in Heterocyclic Chemistry, vol. 22, pp. 390-392, ARKatritzky and AJ Boulton, Eds., Academic Press.

[0056] Those skilled in the art recognize that salts of compounds share the biological utility of their non-salt forms because, under environmental and physiological conditions, salts are in equilibrium with their corresponding non-salt forms. Thus, a wide variety of salts of compounds of Formula 1 are useful for controlling invertebrate pests. Salts of compounds of Formula 1 include acid addition salts with inorganic or organic acids such as hydrobromic acid, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, acetic acid, butyric acid, fumaric acid, lactic acid, maleic acid, malonic acid, oxalic acid, propionic acid, salicylic acid, tartaric acid, 4-toluenesulfonic acid, or valeric acid. When compounds of Formula 1 contain an acidic moiety, such as a carboxylic acid or a phenol, salts also include those formed with organic or inorganic bases, such as pyridine, triethylamine, or ammonia, or amides, hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium, or barium. Thus, the present disclosure includes compounds selected from Formula 1, their N-oxides, and suitable salts.

[0057] Because compounds selected from Formula 1, their stereoisomers, tautomers, N-oxides, and salts typically exist in multiple forms, Formula 1 encompasses all crystalline and amorphous forms of the compounds represented by Formula 1. Amorphous forms include solid embodiments, such as waxes and gums, and 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., various crystalline types). The term "polymorph" refers to a particular crystalline form of a compound that can crystallize in various crystalline forms, which vary in the arrangement and / or conformation of molecules in the crystal lattice. Polymorphs may have the same chemical composition as each other but may 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 may 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 understand that a polymorph of a compound represented by Formula 1 may exhibit beneficial effects (e.g., compatibility in preparing useful formulations, improved biological performance) compared to another polymorph or mixture of polymorphs of the same compound represented by Formula 1. The preparation and isolation of a particular polymorph of a compound represented by Formula 1 can be achieved by methods known to those skilled in the art, including, for example, crystallization using a selected solvent and temperature. Compounds of the present disclosure 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 another. For a comprehensive discussion of polymorphism, see R. Hilfiker, Ed., Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006.

[0058] Embodiments of the present disclosure described in the Summary of the Invention include those set forth below. In the following embodiments, Formula 1 includes its stereoisomers, N-oxides, and salts, and references to "compounds of Formula 1" include the definitions of the substituents defined in the Summary of the Invention, unless further defined in the embodiments.

[0059] Embodiment 1. A compound of Formula 1 wherein L is L1, L2, L3, L4, or L5.

[0060] Embodiment 1a. The compound of embodiment 1, wherein L is L1.

[0061] Embodiment 1b.R 1 a and R 1b Compounds according to embodiment 1a, wherein each is individually H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyl, or C1-C6 haloalkoxyl.

[0062] Embodiment 1c.R 1a and R 1b Compounds according to embodiment 1a, wherein each is individually H, C1-C4 alkyl, C1-C4 haloalkyl, or C1-C4 alkoxyl.

[0063] Embodiment 1d.R 1a and R 1b A compound according to embodiment 1a, wherein each is individually H, C1 alkyl, or C2 alkyl.

[0064] Embodiment 1e.R 1a and R 1b A compound according to embodiment 1a, wherein each is individually H.

[0065] Embodiment 1aa. The compound of embodiment 1, wherein L is L2.

[0066] Embodiment 1ab.R 1a and R 1b Compounds according to embodiment 1aa, wherein each is individually H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyl, or C1-C6 haloalkoxyl.

[0067] Embodiment 1ac.R 1a and R 1bCompounds according to embodiment 1aa, wherein each is individually H, C1-C4 alkyl, C1-C4 haloalkyl, or C1-C4 alkoxy.

[0068] Embodiment 1ad.R 1a and R 1b Compounds according to embodiment 1aa, wherein each is individually H, C1 alkyl, or C2 alkyl.

[0069] Embodiment 1ae.R 1a and R 1b The compound of embodiment 1aa, wherein each is independently H.

[0070] Embodiment 1aaa. The compound of embodiment 1, wherein L is L3.

[0071] Embodiment 1aab.R 1a and R 1b Compounds according to embodiment 1aaa, wherein each is individually H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyl, or C1-C6 haloalkoxyl; and p is 1, 2, 3, or 4.

[0072] Embodiment 1aac.R 1a and R 1b Compounds according to embodiment 1aaa, wherein each is individually H, C1-C4 alkyl, C1-C4 haloalkyl, or C1-C4 alkoxyl; and p is 1, 2, 3, or 4.

[0073] Embodiment 1aad.R 1a and R 1b Compounds according to embodiment 1aaa, wherein each is individually H, C1 alkyl, or C2 alkyl; and p is 1, 2, 3, or 4.

[0074] Embodiment 1aae.R 1a and R 1b Compounds according to embodiment 1aaa, wherein each represents independently H; and p is 1, 2, 3, or 4.

[0075] Embodiment 1aaf.R1a and R 1b A compound according to embodiment 1aaa, wherein each represents independently H; and p is 1.

[0076] Embodiment 1aaaa. The compound of embodiment 1, wherein L is L4.

[0077] Embodiment 1aaab. A compound according to embodiment 1aaaa, wherein T is CHR, O, S, CO, or CS, wherein R is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxyl, or C1-C4 haloalkoxyl.

[0078] Embodiment 1aaac. A compound according to embodiment 1aaaa, wherein T is CHR, O, S, CO, or CS, wherein R is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxyl, or C1-C4 haloalkoxyl.

[0079] Embodiment 1aaad. A compound according to embodiment 1aaaa, wherein T is CHR or CO, and R is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxyl, or C1-C4 haloalkoxyl.

[0080] Embodiment 1aaae. A compound according to embodiment 1aaaa, wherein T is CHR or CO, wherein R is H, halogen, CN, C1 alkyl, or C2 alkyl.

[0081] Embodiment 1aaaf. A compound according to embodiment 1aaaa, wherein T is CHR, wherein R is H, halogen, CN, C1 alkyl, or C2 alkyl.

[0082] Embodiment 1aaag. A compound according to embodiment 1aaaa, wherein T is CHR and R is H, C1 alkyl, or C2 alkyl.

[0083] Embodiment 1aaah. A compound according to embodiment 1aaaa, wherein T is CO, O, S, or CS.

[0084] Embodiment 1aaai. A compound according to embodiment 1aaaa, wherein T is CO or O.

[0085] Embodiment 1aaaj.R 1a and R 1b Compounds according to embodiment 1aaaa, wherein each is individually H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyl, or C1-C6 haloalkoxyl; and p is 1, 2, 3, or 4.

[0086] Embodiment 1aaak.R 1a and R 1b Compounds according to embodiment 1aaaa, wherein each is individually H, C1-C4 alkyl, C1-C4 haloalkyl, or C1-C4 alkoxyl; and p is 1, 2, 3, or 4.

[0087] Embodiment 1aaal.R 1 a and R 1b Compounds according to embodiment 1aaaa, wherein each is individually H, C1 alkyl, or C2 alkyl; and p is 1, 2, 3, or 4.

[0088] Embodiment 1aaam.R 1a and R 1b A compound according to embodiment 1aaaa, wherein each is independently H; and p is 1, 2, 3, or 4.

[0089] Embodiment 1aaan.R 1a and R 1b A compound according to embodiment 1aaaa, wherein each is independently H; and p is 1.

[0090] Embodiment 1aaaaa. The compound of embodiment 1, wherein L is L5.

[0091] Embodiment 1aaaab. A compound according to embodiment 1aaaa, wherein T is CHR, O, S, CO, or CS, wherein R is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxyl, or C1-C4 haloalkoxyl.

[0092] Embodiment 1aaaac. A compound according to embodiment 1aaaa, wherein T is CHR, O, S, CO, or CS, wherein R is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxyl, or C1-C4 haloalkoxyl.

[0093] Embodiment 1aaaad. A compound according to embodiment 1aaaa, wherein T is CHR or CO, and R is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxyl, or C1-C4 haloalkoxyl.

[0094] Embodiment 1aaaae. A compound according to embodiment 1aaaa, wherein T is CHR or CO, and R is H, halogen, CN, C1 alkyl, or C2 alkyl.

[0095] Embodiment 1aaaaf. A compound according to embodiment 1aaaa, wherein T is CHR and R is H, halogen, CN, C1 alkyl, or C2 alkyl.

[0096] Embodiment 1aaaag. A compound according to embodiment 1aaaa, wherein T is CHR and R is H, C1 alkyl, or C2 alkyl.

[0097] Embodiment 1aaaah. A compound according to embodiment 1aaaa, wherein T is CO, O, S, or CS.

[0098] Embodiment 1aaaai. A compound according to embodiment 1aaaa, wherein T is CO or O.

[0099] Embodiment 1aaaaj.R 1a and R 1bCompounds according to embodiment 1aaaa, wherein each is individually H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyl, or C1-C6 haloalkoxyl; and p is 1, 2, 3, or 4.

[0100] Embodiment 1aaaak.R 1a and R 1b Compounds according to embodiment 1aaaaa, wherein each is individually H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyl, or C1-C6 haloalkoxyl; and p is 1, 2, 3, or 4.

[0101] Embodiment 1aaaal.R 1a and R 1b Compounds according to embodiment 1aaaaa, wherein each is individually H, C1-C4 alkyl, C1-C4 haloalkyl, or C1-C4 alkoxyl; and p is 1, 2, 3, or 4.

[0102] Embodiment 1aaaam.R 1a and R 1b Compounds according to embodiment 1aaaaa, wherein each is individually H, C1 alkyl, or C2 alkyl; and p is 1, 2, 3, or 4.

[0103] Embodiment 1aaaan.R 1a and R 1b A compound according to embodiment 1aaaa, wherein each is independently H; and p is 1, 2, 3, or 4.

[0104] Embodiment 1aaaao.R 1a and R 1b A compound according to embodiment 1aaaa, wherein each is independently H; and p is 1.

[0105] Embodiment 2.A is N or CR 3 The compound of Formula 1 or any one of the preceding embodiments, wherein:

[0106] Embodiment 2a.A is CR 3 3. The compound of embodiment 2, wherein

[0107] Embodiment 3.R 2 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy.

[0108] Embodiment 3a.R 2 The compound of embodiment 3, wherein is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, or C1-C4 alkoxy.

[0109] Embodiment 3b.R 2 Compounds according to embodiment 3a, wherein is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, or C3-C4 halocycloalkyl.

[0110] Embodiment 3c.R 2 Compounds according to embodiment 3b, wherein is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, or C3-C4 cycloalkyl.

[0111] Embodiment 3d.R 2 Compounds according to embodiment 3c, wherein is H, halogen, CN, C1-C4 alkyl, or C1-C4 haloalkyl.

[0112] Embodiment 3e.R 2 Compounds according to embodiment 3d, wherein is H, halogen, CN, or C1-C4 alkyl.

[0113] Embodiment 3f.R 2 Compounds according to embodiment 3e, wherein is H, halogen, or C1-C4 alkyl.

[0114] Embodiment 3g.R 2 The compound of embodiment 3f, wherein

[0115] Embodiment 3h.R 2 The compound of embodiment 3e, wherein is halogen.

[0116] Embodiment 3i.R 2 The compound according to embodiment 3e, wherein is C1-C4 alkyl.

[0117] Embodiment 4.R 3 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy.

[0118] Embodiment 4a.R 3 The compound of embodiment 4, wherein is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, or C1-C3 alkoxy.

[0119] Embodiment 4b.R 3 Compounds according to embodiment 4a, wherein is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, or C3-C4 halocycloalkyl.

[0120] Embodiment 4c.R 3 Compounds according to embodiment 4b, wherein is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, or C3-C4 cycloalkyl.

[0121] Embodiment 4d.R 3 Compounds according to embodiment 4c, wherein is H, halogen, CN, C1-C4 alkyl, or C1-C4 haloalkyl.

[0122] Embodiment 4e.R 3 Compounds according to embodiment 4d, wherein is H, halogen, CN, or C1-C4 alkyl.

[0123] Embodiment 4f.R 3 Compounds according to embodiment 4e, wherein is H, halogen, or C1-C4 alkyl.

[0124] Embodiment 4g.R 3 The compound of embodiment 4f, wherein

[0125] Embodiment 4h.R 3 The compound according to embodiment 4g, wherein is C1-C4 alkyl.

[0126] Embodiment 4i.R 3 The compound of embodiment 4h, wherein is halogen.

[0127] Embodiment 4j.R 3 Compounds according to embodiment 4i, wherein is F, Br, or Cl.

[0128] Embodiment 4k.R 3 Compounds according to embodiment 4j, wherein is F or Cl.

[0129] Embodiment 4l.R 3 The compound of embodiment 4k, wherein

[0130] Embodiment 4m.R 3 The compound of embodiment 4k, wherein is Cl.

[0131] Embodiment 4n.R 3 The compound of embodiment 4j, wherein is Br.

[0132] Embodiment 5.R 4 is a 5-6 membered heterocyclic ring, each ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N atoms, wherein up to 2 ring members are independently selected from C(=O), C(=S), S(=O), and S(=O)2, and each ring is optionally substituted with up to 5 substituents independently selected from R, and r is the number of substituents.

[0133] Embodiment 5a.R 4 is selected from U-2 to U-49 or U52 to U61 shown in Appendix 1.

[0134] Appendix 1 [ka] [ka]

[0135] Embodiment 5b.R 4 The compound according to embodiment 5a, wherein is selected from U-2 to U-49.

[0136] Embodiment 5c.R 4 is selected from U-2, U-3, U-4, U-5, U-7, U-9, U-11, U-12, U-13, U-16, U-21, U-25, U-26, U-27, U-28, U-29, U-31, U-32, U-35, U-36, U-37, U-44, U-48, and U-49.

[0137] Embodiment 5d.R 4 is selected from U-9, U-11, U-32, U-36, U-44, U-48, and U-49.

[0138] Embodiment 5e.R 4 The compound according to embodiment 5d, wherein U-9, U-11, U-32, U-36, U-48, and U-44.

[0139] Embodiment 5f.R 4 The compound according to embodiment 5e, wherein is selected from U-9, U-32, U-44, and U-48.

[0140] Embodiment 5g.R 4 The compound according to embodiment 5f, wherein is U-9.

[0141] Embodiment 5h.R 4 The compound of embodiment 5g, wherein is U-11.

[0142] Embodiment 5i.R 4 The compound of embodiment 5h, wherein is U-32.

[0143] Embodiment 5j.R 4 The compound of embodiment 5i, wherein is U-36.

[0144] Embodiment 5k.R 4 The compound of embodiment 5j, wherein is U-44.

[0145] Embodiment 5l.R 4 The compound of embodiment 5k, wherein is U-48.

[0146] Embodiment 5l.R 4 is the compound according to embodiment 5, selected from G-1 to G-37 shown in Appendix 2.

[0147] Appendix 2 [ka] [ka]

[0148] Embodiment 51. A compound according to embodiment 5k, wherein G-2 is O, S, or N.

[0149] Embodiment 5m. The compound of embodiment 5l, wherein G-2 is O.

[0150] Embodiment 5n. The compound of embodiment 5l, wherein G-2 is S.

[0151] Embodiment 5o. The compound of embodiment 5l, wherein G-2 is N.

[0152] Embodiment 6. A compound according to Formula 1 or any one of the preceding embodiments, wherein Rv is H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy.

[0153] Embodiment 6a. The compound of embodiment 6, wherein Rv is H.

[0154] Embodiment 6b. The compound of embodiment 6, wherein Rv is halogen.

[0155] Embodiment 6c. A compound according to embodiment 6, wherein Rv is C1-C6 alkyl.

[0156] Embodiment 6d. A compound according to embodiment 6c, wherein Rv is Me.

[0157] Embodiment 7. A compound of Formula 1 or any one of Embodiments 5-6d, wherein r is 1, 2, 3, 4, or 5.

[0158] Embodiment 7a.r is a compound according to embodiment 7, wherein R is 1 or 2.

[0159] The compound of embodiment 7, wherein embodiment 7b.r is 1.

[0160] The compound of embodiment 7, wherein c.r is 2.

[0161] The compound of embodiment 7, wherein embodiment 7d.r is 3.

[0162] The compound of embodiment 7, wherein embodiment 7e.r is 4.

[0163] Embodiment 7The compound of embodiment 7, wherein f.r is 5.

[0164] Embodiment 8.R 5is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy.

[0165] Embodiment 8a.R 5 The compound of embodiment 8, wherein is H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy.

[0166] Embodiment 8b.R 5 Compounds according to embodiment 8a, wherein is H or halogen.

[0167] Embodiment 8c.R 5 The compound of embodiment 8b, wherein

[0168] Embodiment 8d.R 5 The compound of embodiment 8b, wherein is halogen.

[0169] Embodiment 8e.R 5 is F.

[0170] Embodiment 8e.R 5 The compound of embodiment 8d, wherein is Cl.

[0171] Embodiment 8e.R 5 The compound of embodiment 8d, wherein is Br.

[0172] Embodiment 8e.R 5 The compound according to embodiment 8a, wherein is C1-C4 alkyl.

[0173] Embodiment 9. A compound of Formula 1 or any one of the preceding embodiments, wherein p is 1, 2, 3, or 4.

[0174] Embodiment 9a.p is a compound of embodiment 9, which is 1, 2, or 3.

[0175] The compound of embodiment 9, wherein embodiment 9b.p is 1.

[0176] The compound of embodiment 9, wherein embodiment 9c.p is 2.

[0177] The compound of embodiment 9, wherein embodiment 9d.p is 3.

[0178] Embodiment 10. Q is a 6-membered aromatic ring with 0-2 N on the ring, each ring optionally containing R on a carbon atom ring member. w

[0023] The compound of Formula 1 or any one of the preceding embodiments, wherein the compound is substituted with up to five substituents independently selected from:

[0179] Embodiment 10a.Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each ring optionally containing R on a carbon atom ring member. w The compound of embodiment 10, wherein the compound is substituted with up to five substituents independently selected from:

[0180] Embodiment 10b. Q optionally comprises a carbon atom ring member on which R w Compounds according to embodiment 10a, wherein the phenyl ring is substituted with up to five substituents independently selected from:

[0181] Embodiment 10c. Q optionally comprises a carbon atom ring member on which R w Compounds according to embodiment 10a, wherein the pyridinyl ring is substituted with up to five substituents independently selected from:

[0182] Embodiment 10d. Q optionally comprises a carbon atom ring member on which R w Compounds according to embodiment 10a, wherein the pyrimidinyl ring is substituted with up to five substituents independently selected from:

[0183] Embodiment 10e.Q optionally comprises R on a carbon atom ring member. wCompounds according to embodiment 10a, wherein the pyrazinyl ring is substituted with up to five substituents independently selected from:

[0184] Embodiment 11.R w are independently H, cyano, halogen, SF, SCl, SOCl, SOF, C-C alkyl, C-C alkoxy, C-C haloalkoxy, C-C haloalkyl, C-C alkenyl, C-C haloalkenyl, C-C alkynyl, C-C haloalkynyl, C-C alkoxyalkoxy, C-C alkylthio, C-C haloalkylthio, C-C cycloalkylthio, C-C alkylsulfinyl, C-C haloalkylsulfinyl, C-C alkylsulfonyl, C-C haloalkylsulfonyl, or C-C cycloalkylsulfonyl.

[0185] Embodiment 11a.R w is cyano, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, or C1-C6 haloalkylsulfonyl.

[0186] Embodiment 11b.R w Compounds according to embodiment 11a, wherein is C1-C6 haloalkoxy, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl.

[0187] Embodiment 11c.Rw Compounds according to embodiment 11b, wherein is halogen, C1-C6 haloalkoxy, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl.

[0188] Embodiment 11d.R w Compounds according to embodiment 11c, wherein is Br, OCF3, SCF3, OCF2CFCF3, CF3, SOCF3, or SO2CF3.

[0189] Embodiment 11e.R w The compound of embodiment 11d, wherein is OCF3.

[0190] Embodiment 11f.R w The compound of embodiment 11d, wherein is SCF3.

[0191] Embodiment 11g.R w The compound of embodiment 11d, wherein is CF3.

[0192] Embodiment 11h.R w The compound of embodiment 11d, wherein is SOCF3 or SO2CF3.

[0193] Embodiment 11i.R w The compound of embodiment 11h, wherein is OCF2CFCF3.

[0194] Embodiment 11j.R w The compound of embodiment 11h, wherein is Br.

[0195] Embodiment 12. A compound of Formula 1 or any one of the preceding embodiments, wherein s is 1, 2, 3, 4, or 5.

[0196] Embodiment 12a.s is a compound of embodiment 12, wherein R is 1 or 2.

[0197] The compound of embodiment 12, wherein embodiment 12b.s is 1.

[0198] The compound of embodiment 12, wherein c.s is 2.

[0199] The compound of embodiment 12, wherein embodiment 12d.s is 3.

[0200] The compound of embodiment 12, wherein embodiment 12 e.s is 4.

[0201] Embodiment 12The compound of embodiment 12, wherein f.s is 5.

[0202] Embodiment X. A method of controlling and combating invertebrate pests comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula 1.

[0203] Embodiment X1. The method of embodiment X, wherein the invertebrate pest is a member of the order Hemiptera.

[0204] Embodiment X2. The method of embodiment X1, wherein the member of the order Hemiptera is a member of the suborder Homoptera.

[0205] Embodiment X2a. The method of embodiment X2, wherein the suborder Homoptera includes planthoppers from the families Cicadellidae and Delphacidae.

[0206] Embodiment X2b. The method of embodiment X2, wherein the Homoptera includes aphids from the family Aphididae.

[0207] Embodiment X2c. The method of embodiment X2, wherein the Homoptera includes whiteflies from the family Aleyrodidae.

[0208] Embodiment X3. The method of embodiment X2, wherein the Homoptera includes CPH, CMA, GPA, and WF.

[0209] Embodiment X4. The order Homoptera includes Aphis fabae Scopoli (the black bean aphid), Aphis gossypii Glover (the cotton aphid), Bemisia tabaci Gennadius (the tobacco whitefly), Bemisia argentifolii Bellows & Perring (the silverleaf whitefly), Dialeurodes citri Ashmead (the citrus whitefly), and Trialeurodes vaporariorum Westwood (the greenhouse whitefly); Empoasca fabae Harris (potato leafhopper), Laodelphax striatellus Fallen (small brown planthopper), Macrosteles quadrilineatus Forbes (two-legged striped leafhopper), Myzus persicae Sulzer (green peach aphid), Nephotettix cincticeps Uhler (green rice leafhopper), Nephotettix nigropictus Stol (black-striped rice leafhopper), Nilaparvata lugens Stol (brown planthopper), Peregrinus maidis Ashmead (corn planthopper), Sogatella furcifera Horvath (white-backed planthopper), Tagosodes orizicolus Muir (rice delphacid), Typhlocyba pomaria McAtee (white apple leafhopper), or Erythroneura spp. (grape leafhopper).

[0210] Embodiment X5. The method of embodiment X1, wherein the Hemiptera is a member of the suborder Heteroptera.

[0211] Embodiment X5a. The suborder Heteroptera includes Acrosternum hilare Say (green grass bug), Anasa tristis De Geer (helicopter bug), Blissus leucopterus leucopterus Say (American long-horned stink bug), Cimex lectularius Linnaeus (bed bug), Corythucha gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), Dichelops melacanthus Dallas (greenberry stink bug), Dysdercus suturellus Herrich-Schaeffer (Cotton Stainer), Euschistus heros Fabricius (Neotropical Brown Stink Bug), Euschistus servus Say (Brown Stink Bug), Euschistus variolarius Palisot de Beauvois (One-Spotted Stink Bug), Graptostethus spp. (Seed Bug Complex), Halyomorpha halys Stol (Marbled Marble Stink Bug), Leptoglossus corculus Say (Leaf-Footed Pine Seed Bug), Lygus lineolaris Palisot de Beauvois (Green Mirid Bug), Nezara viridula Linnaeus (Southern Green Stink Bug), Oebalus pugnax Fabricius (Rice Bug), Oncopeltus fasciatusDallas (large milkweed bug), Pseudatomoscelis seriatus Reuter (cotton flea beetle).

[0212] Embodiment X6. The method of embodiment X5, wherein the suborder of Pentatomida includes stink bugs from the family Pentatomidae.

[0213] Embodiment X7. The suborder Heteroptera includes Acrosternum hilare Say (green lace bug), Dichelops melacanthus Dallas (greenberry stink bug), Euschistus heros Fabricius (neotropical brown stink bug), Euschistus servus Say (brown stink bug), Euschistus variolarius Palisot de Beauvois (one-spotted stink bug), Halymorpha halys Stol (brown marmorated stink bug), Nezara viridula Linnaeus (southern green stink bug), Oebalus pugnax Fabricius (rice stink bug).

[0214] Embodiment X8. The suborder Heteroptera includes Anasa tristis De Geer (helicopter bug), Blissus leucopterus Say (American long-horned bug), Cimex lectularius Linnaeus (bed bug), Corythucha gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), Dysdercus suturellus Herrich-Schaffer (cotton stainer), Graptostethus spp. (seed bug complex), Leptoglossus corculus Say (leaf-footed pine seed bug), Lygus lineolaris Palisot de Beauvois (green mistletoe bug), Oncopeltus fasciatus Dallas (large milkweed bug), or Pseudatomoscelis seriatus Reuter (cotton flea beetle).

[0215] Embodiments of the present disclosure, including the above-described Embodiments 1-X8 and any other embodiments described herein, can be combined in any manner, and the descriptions of 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 the above-described Embodiments 1-X8 and any other embodiments described herein, and any combination thereof, relate to the compositions and methods of the present disclosure.

[0216] Combinations of embodiments 1 to 8 are exemplified by the following:

[0217] Embodiment A1. A compound of Formula 1 During the ceremony, A is CR 3 and; R 2 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 3 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 4 is a 5-6 membered heterocycle, each ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N atoms, wherein up to 2 ring members are independently selected from C(=O), C(=S), S(=O), and S(=O)2, and each ring or ring system is optionally substituted with up to 5 substituents independently selected from R, and r is the number of substituents; each R is independently H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy; r is 1, 2, 3, 4, or 5; R 5 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; Q is a 6-membered aromatic ring having 0-2 N on the ring, each ring optionally having R on a carbon atom ring member. w and is substituted with up to five substituents independently selected from: R ware independently cyano, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, or C1-C6 haloalkylsulfonyl; s is 1, 2, 3, 4, or 5; A compound of formula 1.

[0218] Embodiment B1. A compound according to embodiment A1, R 2 is H, halogen, or C1-C4 alkyl; R 3 is H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 4 is selected from U-2 to U-49 or U52 to U61 shown in Appendix 1; r is 1 or 2; R 5 is H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R w is C1-C6 haloalkoxy, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl; s is 1 or 2; A compound according to embodiment A1.

[0219] Embodiment C1. A compound according to embodiment B1, R 2 is H; R 3 is H or a halogen; R 4 is selected from U-2 to U-49 Rv is H; R 5 is H or a halogen; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which may optionally be joined on a carbon atom ring member by R w and is substituted with up to five substituents independently selected from: R w is OCF3, SCF3, OCF2CFCF3, CF3, SOCF3, or SO2CF3; A compound according to embodiment B1.

[0220] Embodiment D1. A compound according to embodiment B1, R 2 is H; R 3 is H or a halogen; R 4 is selected from U-2 to U-49; Rv is C1-C6 alkyl; R 5 is H; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which may optionally be joined on a carbon atom ring member by R w and is substituted by up to five substituents independently selected from A compound according to embodiment B1.

[0221] Embodiment E1. A compound according to embodiment C1, R 3 is a halogen; R 4 is selected from U-2, U-3, U-4, U-5, U-7, U-9, U-11, U-12, U-13, U-16, U-21, U-25, U-26, U-27, U-28, U-29, U-31, U-32, U-35, U-36, U-37, U-44, U-48, and U-49; R 5 is H; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which may optionally be joined on a carbon atom ring member by Rw and is substituted by up to five substituents independently selected from A compound according to embodiment C1.

[0222] Embodiment F1. A compound according to embodiment E1, R 3 is F; R 4 is selected from U-9, U-11, U-32, U-36, U-44, and U-48; Q optionally has a carbon atom ring member R w is a phenyl ring substituted with up to five substituents independently selected from A compound according to embodiment E1.

[0223] Embodiment G1.R 4 A compound according to embodiment F1, wherein is selected from U-44 and U-48.

[0224] Embodiment H1.R 4 The compound according to embodiment G1, wherein is selected from the group of U-44.

[0225] Embodiment I1.R 4 The compound according to embodiment G1, wherein is selected from the group of U-48.

[0226] Embodiment J1. A compound according to embodiment B1, R 2 is C1-C4 alkyl; R 3 is H or a halogen; R 4 is selected from U-2 to U-49 Rv is H; r is 2; R 5 is H; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which may optionally be joined on a carbon atom ring member by R w and is substituted with up to five substituents independently selected from: R w is OCF3, SCF3, OCF2CFCF3, CF3, SOCF3, or SO2CF3; A compound according to embodiment B1.

[0227] Embodiment A2. A compound of Formula 1, During the ceremony, A is CR 3 and; R 2 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 3 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 4 is a 5-6 membered heterocycle, each ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N atoms, wherein up to 2 ring members are independently selected from C(=O), C(=S), S(=O), and S(=O)2, and each ring or ring system is optionally substituted with up to 5 substituents independently selected from R, and r is the number of substituents; each R is independently H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy; r is 1, 2, 3, 4, or 5; R 5 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; Q is a 6-membered aromatic ring with 0-2 N on the ring, and each ring optionally has R w and is substituted with up to five substituents independently selected from: Rw are independently cyano, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, or C1-C6 haloalkylsulfonyl; s is 1, 2, 3, 4, or 5; A compound of formula 1.

[0228] Embodiment B2. A compound according to embodiment A2, R 2 is H, halogen, or C1-C4 alkyl; R 3 is H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 4 is selected from U-2 to U-49 or U52 to U61 shown in Appendix 1; r is 1 or 2; R 5 is H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R w is C1-C6 haloalkoxy, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl; s is 1 or 2; A compound according to embodiment A2.

[0229] Embodiment C2. A compound according to embodiment B2, R 2 is H; R 3 is H or a halogen; R 4is selected from U-2 to U-49; R v is H; r is 2; R 5 is H or a halogen; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which may optionally be joined on a carbon atom ring member by R w and is substituted with up to five substituents independently selected from: R w is OCF3, SCF3, OCF2CFCF3, CF3, SOCF3, or SO2CF3; A compound according to embodiment B2.

[0230] Embodiment D2. A compound according to embodiment B2, R 2 is H; R 3 is H or a halogen; R 4 is selected from U-2 to U-49 R v is C1-C6 alkyl; R 5 is H; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which may optionally be joined on a carbon atom ring member by R w and is substituted by up to five substituents independently selected from A compound according to embodiment B2.

[0231] Embodiment E2. A compound according to embodiment C2, R 3 is a halogen; R 4 is selected from U-2, U-3, U-4, U-5, U-7, U-9, U-11, U-12, U-13, U-16, U-21, U-25, U-26, U-27, U-28, U-29, U-31, U-32, U-35, U-36, U-37, U-44, U-48, and U-49; R 5 is H; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which may optionally be joined on a carbon atom ring member by R w and is substituted by up to five substituents independently selected from A compound according to embodiment C2.

[0232] Embodiment F2. A compound according to embodiment E2, R 3 is F; R 4 is selected from U-9 and U-44; Q optionally has a carbon atom ring member R w is a phenyl ring substituted with up to five substituents independently selected from A compound according to embodiment E2.

[0233] Embodiment G2.R 4 The compound according to embodiment F2, wherein is U-44.

[0234] Embodiment H2.R 4 The compound according to embodiment F2, wherein is U-48.

[0235] Embodiment A3. A compound of Formula 1, During the ceremony, A is CR 3 and; R 2 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 3 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 4is a 5-6 membered heterocycle, each ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N atoms, wherein up to 2 ring members are independently selected from C(=O), C(=S), S(=O), and S(=O)2, and each ring or ring system is optionally substituted with up to 5 substituents independently selected from R, and r is the number of substituents; Each R v are independently H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy; r is 1, 2, 3, 4, or 5; R 5 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; Q is a 6-membered aromatic ring with 0-2 N on the ring, and each ring optionally has R w and is substituted with up to five substituents independently selected from: R w are independently cyano, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, or C1-C6 haloalkylsulfonyl; s is 1, 2, 3, 4, or 5; A compound of formula 1.

[0236] Embodiment B3. A compound according to embodiment A3, R 2 is H, halogen, or C1-C4 alkyl; R 3is H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 4 is selected from U-2 to U-49 or U52 to U61 shown in Appendix 1; r is 1 or 2; R 5 is H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R w is C1-C6 haloalkoxy, C1-C6 haloalkyl, C1-C6 haloalkenyl, C2-C6 haloalkynyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl; s is 1 or 2; A compound according to embodiment A3.

[0237] Embodiment C3. A compound according to embodiment B3, R 2 is H; R 3 is H or a halogen; R 4 is selected from U-2 to U-49; R v is H; r is 2; R 5 is H; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which may optionally be joined on a carbon atom ring member by R w and is substituted with up to five substituents independently selected from: R w is OCF3, SCF3, OCF2CFCF3, CF3, SOCF3, or SO2CF3; A compound according to embodiment B3.

[0238] Embodiment D3. A compound according to embodiment B3, R 2 is H; R3 is H or a halogen; R 4 is selected from U-2 to U-49; R v is C1-C6 alkyl; R 5 is H; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which may optionally be joined on a carbon atom ring member by R w substituted with up to five substituents independently selected from: A compound according to embodiment B3.

[0239] Embodiment E3. A compound according to embodiment C3, R 3 is a halogen; R 4 is selected from U-2, U-3, U-4, U-5, U-7, U-9, U-11, U-12, U-13, U-16, U-21, U-25, U-26, U-27, U-28, U-29, U-31, U-32, U-35, U-36, U-37, U-44, U-48, and U-49; R 5 is H; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which may optionally be joined on a carbon atom ring member by R w substituted with up to five substituents independently selected from: A compound according to embodiment C3.

[0240] Embodiment F3. A compound according to embodiment E3, R 3 is F; R 4 is U-44 or U-48; Q optionally has a carbon atom ring member R w is a phenyl ring substituted with up to five substituents independently selected from A compound according to embodiment E3.

[0241] Embodiment G3.R4 A compound according to embodiment F3, wherein is selected from the group of U-44.

[0242] Embodiment H3.R 4 A compound according to embodiment F3, wherein is selected from the group of U-48.

[0243] Embodiment A4. A compound of Formula 1, During the ceremony, A is CR 3 and; R 2 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 3 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 4 is a 5-6 membered heterocycle, each ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N atoms, wherein up to 2 ring members are independently selected from C(=O), C(=S), S(=O), and S(=O)2, and each ring or ring system is optionally substituted with up to 5 substituents independently selected from R, and r is the number of substituents; each R is independently H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy; r is 1, 2, 3, 4, or 5; R 5 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; Q is a 6-membered aromatic ring with 0-2 N on the ring, and each ring optionally has R wand is substituted with up to five substituents independently selected from: R w are independently cyano, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, or C1-C6 haloalkylsulfonyl; s is 1, 2, 3, 4, or 5; A compound of formula 1.

[0244] Embodiment B4. A compound according to embodiment A4, R 2 is H, halogen, or C1-C4 alkyl; R 3 is H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 4 is selected from U-2 to U-49 or U52 to U61 shown in Appendix 1; r is 1 or 2; R 5 is H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R w is C1-C6 haloalkoxy, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl; s is 1 or 2; A compound according to embodiment A4.

[0245] Embodiment C4. A compound according to embodiment B4, R 2 is H; R 3is H or a halogen; R 4 is selected from U-2 to U-49; R v is H; R 5 is H or a halogen; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which may optionally be joined on a carbon atom ring member by R w and is substituted with up to five substituents independently selected from: R w is OCF3, SCF3, OCF2CFCF3, CF3, SOCF3, or SO2CF3; A compound according to embodiment B4.

[0246] Embodiment D4. A compound according to embodiment B4, R 2 is H; R 3 is H or a halogen; R 4 is selected from U-2 to U-49; R v is C1-C6 alkyl; R 5 is H; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which may optionally be joined on a carbon atom ring member by R w substituted with up to five substituents independently selected from: A compound according to embodiment B4.

[0247] Embodiment E4. A compound according to embodiment C4, R 3 is a halogen; R 4 is selected from U-2, U-3, U-4, U-5, U-7, U-9, U-11, U-12, U-13, U-16, U-21, U-25, U-26, U-27, U-28, U-29, U-31, U-32, U-35, U-36, U-37, U-44, U-48, and U-49; R5 is H; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which may optionally be joined on a carbon atom ring member by R w substituted with up to five substituents independently selected from: A compound according to embodiment C4.

[0248] Embodiment D4. A compound according to embodiment E4, R 3 is F; R 4 is selected from U-9, U-11, U-32, U-36, U-44, and U-48; Q optionally has a carbon atom ring member R w is a phenyl ring substituted with up to five substituents independently selected from A compound according to embodiment E4.

[0249] Embodiment E4.R 4 The compound according to embodiment D4, wherein is selected from U-44 to U-48.

[0250] Embodiment F4.R 4 A compound according to embodiment E4, wherein is selected from the group of U-44.

[0251] Embodiment G4.R 4 The compound according to embodiment F4, wherein is selected from the group of U-48.

[0252] Embodiment H4. A compound according to embodiment B4, R 2 is C1-C4 alkyl; R 3 is H or a halogen; R 4 is selected from U-2 to U-49; R v is H; r is 2; R 5 is H; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which may optionally be joined on a carbon atom ring member by R w and is substituted with up to five substituents independently selected from: R w is OCF3, SCF3, OCF2CFCF3, CF3, SOCF3, or SO2CF3; A compound according to embodiment B4.

[0253] Embodiment A5. A compound of Formula 1, During the ceremony, A is CR 3 and; R 2 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 3 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 4 is a 5-6 membered heterocycle, each ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N atoms, wherein up to 2 ring members are independently selected from C(=O), C(=S), S(=O), and S(=O)2, and each ring or ring system is optionally substituted with up to 5 substituents independently selected from R, and r is the number of substituents; each R is independently H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy; r is 1, 2, 3, 4, or 5; R 5 is H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; Q is a 6-membered aromatic ring with 0-2 N on the ring, and each ring optionally has R w and is substituted with up to five substituents independently selected from: R w are independently cyano, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, or C1-C6 haloalkylsulfonyl; s is 1, 2, 3, 4, or 5; A compound of formula 1.

[0254] Embodiment B5. A compound according to embodiment A5, R 2 is H, halogen, or CC1-C4 alkyl; R 3 is H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 4 is selected from U-2 to U-49 or U52 to U61 shown in Appendix 1; r is 1 or 2; R 5 is H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R w is C1-C6 haloalkoxy, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl; s is 1 or 2; A compound according to embodiment A5.

[0255] Embodiment C5. A compound according to embodiment B5, R 2 is H; R 3 is H or a halogen; R 4 is selected from U-2 to U-49; R v is H; R 5 is H or a halogen; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which may optionally be joined on a carbon atom ring member by R w and is substituted with up to five substituents independently selected from: R w is Br, OCF3, SCF3, OCF2CFCF3, CF3, SOCF3, or SO2CF3; A compound according to embodiment B5.

[0256] Embodiment D5. A compound according to embodiment B5, R 2 is H; R 3 is H or a halogen; R 4 is selected from U-2 to U-49; R v is C1-C6 alkyl; R 5 is H; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which may optionally be joined on a carbon atom ring member by R w and is substituted by up to five substituents independently selected from A compound according to embodiment B5.

[0257] Certain embodiments include one or more compounds of Formula 1 selected from the group consisting of: [ka] 3-fluoro-5-(2H-1,2,3-triazol-2-yl)-4-[(1E)-2-[4-(trifluoromethoxy)phenyl]ethenyl]pyridine, [ka] 3-fluoro-5-(2H-1,2,3-triazol-2-yl)-4-[(1E)-2-[4-[(trifluoromethyl)thio]phenyl]ethenyl]pyridine, [ka] 3-fluoro-5-(2H-1,2,3-triazol-2-yl)-4-[2-[4-(trifluoromethoxy)phenyl]ethyl]pyridine, [ka] 3-chloro-5-(2H-1,2,3-triazol-2-yl)-4-[2-[4-(trifluoromethoxy)phenyl]ethyl]pyridine, [ka] 3-fluoro-5-(1H-pyrazol-1-yl)-4-[2-[4-(trifluoromethoxy)phenyl]ethyl]pyridine, [ka] 3-chloro-5-(1H-pyrazol-1-yl)-4-[2-[4-(trifluoromethoxy)phenyl]ethyl]pyridine, [ka] 3-fluoro-5-(2H-1,2,3-triazol-2-yl)-4-[2-[4-(trifluoromethoxy)phenyl]cyclopropyl]pyridine, [ka] 3-chloro-5-(1H-1,2,3-triazol-1-yl)-4-[2-[4-(trifluoromethoxy)phenyl]cyclopropyl]pyridine, [ka] 3-fluoro-5-(2H-1,2,3-triazol-2-yl)-4-[2-[4-(trifluoromethyl)phenyl]cyclopropyl]pyridine, [ka] 3-chloro-5-(1H-1,2,3-triazol-1-yl)-4-[2-[4-(trifluoromethyl)phenyl]cyclopropyl]pyridine, and [ka] 3-Fluoro-5-(1H-pyrazol-1-yl)-4-[2-[4-(trifluoromethyl)phenyl]cyclopropyl]pyridine.

[0258] Embodiment Y1. A composition comprising a compound of Formula 1 or any one of the preceding embodiments 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.

[0259] Embodiment Y2. The at least one additional biologically active compound or agent is abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, afidopiropen, amidoflumet, amitraz, avermectin, azadirachtin, azinphos-methyl, benfuracarb, bensultap, bifenthrin, bifenazate, bistrifluron, borate, bromantraniliprole, buprofezin, carbaryl, carbofuran, cartap, carsol, chlorantraniliprole, chlorfena Pill, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezine, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin, cycloxapride, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalodiamide, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dichlorantraniliprole, geldrin, diflu Benzuron, dimefluthrin, dimehypo, dimethoate, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flometoquin, flonicamid, flubendiamide, flucythrinate, flufenerim, flufenoxuron, flufenoxystrobin, flufensulfone, flu Opiram, flupyradifurone, fluvalinate, tau-fluvalinate, fonofos, formetanate, fosthiazate, halofenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, indoxacarb, insecticidal soap, isofenphos, lufenuron, malathion, meperfluthrin, metaflumizone, metaldehyde, methamidophos, methidathion, methiodicarb, methomyl, methoprene, methoxychlor, methoxyfenozide, metofluthrin, monocrotophos, monofluorothrin, 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-(methylsulfonyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide Voxamide, 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, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicar Bu, profenofos, profluthrin, propargite, protrifenbut, piflubumid, pymetrozine, pyrafluprole, pyrethrins, pyridaben, pyridalyl, pyrifluquinazon, pyriminostrobin, pyriprole, pyriproxyfen, rotenone, ryanodine, silafluofen, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulprofos, sulfoxaflor, tebufeno The composition of embodiment Y1, wherein the insecticide is selected from the group consisting of tetrachlorolantraniliprole, tetrachlorvinphos, tetramethrin, tetramethylfluthrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, thioxazaphen, tolfenpyrad, tralomethrin, triazamate, trichlorfon, triflumezopyrim, triflumuron, Bacillus thuringiensis delta-endotoxin, entomopathogenic bacteria, entomopathogenic viruses, and entomopathogenic fungi.

[0260] Embodiment Y3. 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 antiviral agent is selected from the group consisting of benzodiazepines, 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 nuclear polyhedrosis virus.

[0261] Embodiment Y4. The composition of any one of embodiments Y1-Y3, further comprising a liquid fertilizer.

[0262] Embodiment Y5. The composition of embodiment Y4, wherein the liquid fertilizer is aqueous.

[0263] Embodiment Y6. A soil dip formulation comprising the composition of any one of embodiments Y1-Y3.

[0264] Embodiment Y7. A spray composition comprising the composition of any one of Embodiments Y1-Y3 and a propellant.

[0265] 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.

[0266] 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, the housing having at least one opening sized to allow passage of invertebrate pests, thereby allowing the invertebrate pests to access the bait composition from a location outside the housing; and the housing further configured to be placed at or near a location of suspected or known activity of invertebrate pests.

[0267] 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.

[0268] Embodiment Y11. The composition of embodiment Y10 which is water-dispersible or water-soluble.

[0269] Embodiment Y12. A liquid or dry formulation comprising the composition of any one of embodiments Y1-Y3 for use in a drip irrigation system, in furrow at planting, with a handheld sprayer, backpack sprayer, boom sprayer, ground sprayer, aerial application, unmanned aerial vehicle, or as a seed treatment.

[0270] Embodiment Y13. A liquid or dry formulation according to embodiment Y12, wherein the formulation is sprayed in minute amounts.

[0271] Notably, compounds of the present disclosure are characterized by favorable metabolism and / or soil persistence patterns and exhibit activity in controlling and combating a variety of agricultural and non-agricultural invertebrate pests.

[0272] Of particular note is that due to the invertebrate pest control spectrum and economic importance, the protection of agricultural crops from damage or injury caused by invertebrate pests by controlling and eliminating invertebrate pests is an embodiment of the present disclosure. Due to their favorable translocation or systemic properties in plants, the compounds of the present disclosure also protect leaves or other plant parts that do not come into direct contact with the compound of Formula 1 or a composition comprising the compound.

[0273] Also of note as an embodiment of the present disclosure is a composition comprising a compound of any of the preceding embodiments, and 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.

[0274] Also noteworthy as an embodiment of the present disclosure is a composition for controlling and combating invertebrate pests, comprising a compound of any of the preceding embodiments, and 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 disclosure further include a method of controlling and combating invertebrate pests, comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of any of the preceding embodiments (e.g., as a composition described herein).

[0275] Embodiments of the present disclosure also include compositions comprising a compound of any of the preceding embodiments in the form of a liquid soil dip formulation.Embodiments of the present disclosure further include a method of controlling and eradicating invertebrate pests, comprising contacting soil with a biologically effective amount of a liquid composition as a soil dip comprising a compound of any of the preceding embodiments.

[0276] Embodiments of the present invention also include a spray composition for controlling and eliminating invertebrate pests, the spray composition comprising a biologically effective amount of a compound of any of the preceding embodiments and a propellant. Embodiments of the present invention further include a bait composition for controlling and eliminating invertebrate pests, the bait composition comprising a biologically effective amount of a compound of any of the preceding embodiments, one or more food materials, optionally an attractant, and optionally a wetting agent. Embodiments of the present invention also include a device for controlling and eliminating invertebrate pests, the device comprising the bait composition and a housing configured to contain the bait composition, the housing having at least one opening sized to allow invertebrate pests to pass through, thereby allowing invertebrate pests to access the bait composition from a location outside the housing, the housing further configured to be placed at or near a location of potential or known invertebrate pest activity.

[0277] Embodiments of the present disclosure also include a method of protecting seeds from invertebrate pests, comprising contacting seeds with a biologically effective amount of a compound of any of the preceding embodiments.

[0278] Embodiments of the present disclosure also include a method of protecting an animal from invertebrate parasitic pests, comprising administering to the animal a parasiticidally effective amount of a compound of any of the preceding embodiments.

[0279] Embodiments of the present disclosure also include methods 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, an N-oxide or a salt thereof (e.g., as a composition described herein), but which are not methods of medical treatment of the human or animal body by therapy.

[0280] The present disclosure 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, an N-oxide or a salt thereof, and at least one additional ingredient selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, and optionally further comprising a biologically effective amount of at least one additional bioactive compound or agent, but which are not methods of medical treatment of the human or animal body by therapy.

[0281] To prepare compounds of formula 1, one or more of the following methods and variations as described in Schemes 1-8 can be used. R in compounds of the formula 1 a, R 1b , R 2 ,R 3 , R 4 , R 5 The definitions of A, L, and Q are as defined above in the Summary of the Invention of this disclosure unless otherwise specified. Ambient or room temperature is defined as about 20-25°C. As shown in Scheme 1, the compound of Formula 1 (R 4 Compounds of Formula 1, in which X is attached to the remainder of the molecule through a carbon atom, can be prepared by contacting compounds of Formula 2a (where X is Cl, Br, or I) with a boronic acid or an organotin compound of Formula 3 in the presence of a palladium catalyst. A wide variety of palladium-containing compounds and complexes are useful as catalysts in the present process. Examples of palladium-containing compounds and complexes useful as catalysts in the process of Scheme 1 include Pd(OAc) (palladium(II) acetate), PdCl (palladium(II) chloride), PdCl(PPh) bis(triphenylphosphine)palladium(II) dichloride, Pd(PPh) (tetrakis(triphenylphosphine)palladium(0), Pd(CHO) (palladium(II) acetylacetonate), and Pd(dba) tris(dibenzylideneacetone)dipalladium(0). Also, as shown in Scheme 1, compounds of Formula 1 (R 4Compounds of formula 1, in which X is attached to the rest of the molecule through a nitrogen atom, can be prepared by contacting compounds of formula 2a, in which X is Cl, Br, or I, with compounds of formula 4, in the presence of a copper or palladium catalyst, which are heterocyclic compounds having NH as a ring member, where H can be replaced by another functional group during a chemical reaction. For recent review articles and books on this type of functional group transformation, see, for example, F. Bellina et al., Synthesis 2004, 15, 2419-2440; P. Espinet and A M Echavarren, Angewandte Chemie, International Edition 2004, 43, 4704-4734; and J. J. Li, G. W. Gribble, editors, Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist, 2000. K. W. Anderson et al., Angewandte Chemie, International Edition 2006, 45, 6523-6527. [ka]

[0282] Alternatively, as shown in Scheme 2, a compound of Formula 1 can be prepared by contacting a compound of Formula 2b (wherein X is F or Cl) with a compound of Formula 4 in the presence of a base, such as K2CO3 or Cs2CO3. It is reasonably believed that a wide variety of known general procedures (see, for example, JD Culshaw et al., Synlett 2012, 23, 1816-1820) can be readily adapted by one skilled in the art to the method of Scheme 2. The method of Scheme 2 is illustrated by Synthesis Example 1, Step B, Synthesis Example 2, Step C, and Synthesis Example 3, Step B. [ka]

[0283] As shown in Scheme 3, compounds of Formula 2c (wherein L is L1) can be prepared by a Wittig reaction by coupling a carbonyl compound of Formula 10 with an ylide of Formula 4 or a phosphonate derivative of Formula 5 via a Wittig-Horner reaction to obtain both cis and trans olefin derivatives. Many compounds of Formula 10, Formula 4, and Formula 5 are known in the literature or commercially available (see, for example, M. Hatsuda, Chao-Tun Cao; et al., J. Phys. Org. Chem., 2021, 34, 4246; Q. Li; et al., J. Org. Chem., 2018, 83, 296-302). The method of Scheme 3 is illustrated by Synthesis Example 1, Step A. [ka]

[0284] As shown in Scheme 4, compounds of formula 2d (where L is L2) can be prepared by reduction of compounds of formula 2c. The hydrogenation of alkenes to alkanes is well known in the literature (see, for example, S. Efange et al., J. Med. Chem., 1990, 33, 3133-3138). [ka]

[0285] Also, as shown in Scheme 5, compounds of formula 2e (wherein L is L2) can be prepared by coupling of boronic acid esters of formula 6 with N-heteroaromatic compounds of formula 11. This method is known in the literature (see, for example, Llaveria et al., J. Am. Chem. Soc., 2015, 137, 10958-10961). The method of Scheme 5 is shown by Synthesis Example 2, Step B. [ka]

[0286] As shown in Scheme 6, cyclopropyl compounds of formula 2f (where L is L3 and p is 1) can be prepared by the Simmons-Smith reaction or other cyclopropyl-forming reactions available in the literature. For example, treatment of an olefin with CH2I2 and ZnEt2 gives the desired cyclopropyl derivative of formula 2c. This method is known in the literature (see, for example, Jiang Long et al., J. Am. Chem. Soc., 2003, 125, 13632-13633). [ka]

[0287] Also, as shown in Scheme 7, cyclopropyl compounds of formula 2f (wherein L is L3 and p is 1) can be prepared by treating alkenes of formula 7 with hydrazones of formula 12, which can be generated from carbonyl compounds of formula 10. Many examples of formulas 7 and 12 are known in the literature or commercially available. This method is known in the literature (see, for example, Xiaoxu Wang; et al., J. Am. Chem. Soc., 2021, 143, 11121-11129). The method of Scheme 7 is illustrated by Synthesis Example 3, Step A. [ka]

[0288] As shown in Scheme 8, cycloalkyl compounds of formula 2f (wherein L is L3 and p is 2, 3, or 4) can be prepared from carbonyl compounds of formula 13. The conversion of carbonyl compounds of formula 13 to trifluoromethanesulfonates of formula 14 is well known in the literature (e.g., Nowikow, Christina; et al., Bio. & Med. Chem., 2019, 27, 115032; Naijing Su; et al., Org. Lett., 2017, 19, 3990-3993). Palladium coupling of trifluoromethanesulfonates of formula 14 with boronic acids of formula 8 provides compounds of formula 15. This method is discussed in Scheme 1. Hydrogenolytic reduction of olefins of formula 10 provides cycloalkyl compounds of formula 2g. This method is known in the literature (see, for example, S. Boyer et al., WO 2012064631). Many examples of formula 13 and formula 8 are known in the literature or are commercially available. [ka]

[0289] As shown in Scheme 9, compounds of formula 2h (where L is L-4) can be prepared by reduction of compounds of formula 2i (where L is L-5). Hydrogenation of olefins near formula 2i is well known in the literature (see, for example, Richard John, Booth; et al., WO 2006061715). [ka]

[0290] As shown in Scheme 10, compounds of formula 2i (wherein L is L-5 and T is CO, CH, CHOMe, et al.) can be prepared by converting carbinol compounds of formula 2j via typical functional group transformation reactions, such as oxidation, reduction, and ether formation (see, for example, Jialiang, Wang; et al., J. Org. Chem. 2009, 74, 3299-3304). [ka]

[0291] As shown in Scheme 11, commercially available or known compounds of formula 11 are treated with a base such as lithium diisopropylamide, 2,2,6,6-tetramethylpiperidinyl magnesium chloride lithium chloride complex, etc., at temperatures between −100° C. and −10° C. in an ethereal solvent such as THF, diethyl ether, or dioxane to generate the desired anion in situ. Compounds of formula 2j can be prepared by quenching the anion with commercially available or known aldehydes of formula 16. This method has been described in the literature (see, for example, Ming, Xu, et al., International Publication No. 2022271901). [ka]

[0292] 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 intermediates. In this case, incorporating a protection / deprotection sequence into the synthesis or functional group interconversion will aid in obtaining the desired product. The use and selection of protecting groups will be apparent to those skilled in the art of 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, it may be necessary to perform additional routine synthetic steps not detailed after the introduction of a given reagent shown in any individual scheme to complete the synthesis of a compound 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 preceding schemes in an order other than the specific order presented to prepare a compound of Formula 1.

[0293] Those skilled in the art will further recognize that the compounds of Formula 1 and intermediates described herein can be subjected to a variety of electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

[0294] Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present disclosure to its fullest extent. Accordingly, the following synthetic examples are intended to be merely illustrative and are not intended to limit the present disclosure in any way. The steps in the following synthetic examples illustrate the step-by-step procedures in the overall synthetic transformation, and the starting materials for each step are not necessarily prepared by the specific preparative run whose procedure is described in another example or step. Ambient or room temperature is defined as approximately 20-25°C. Percentages are by weight, except in the case of chromatographic solvent mixtures, or unless otherwise specified. Parts and percentages for chromatographic solvent mixtures are by volume, unless otherwise specified. MPLC refers to medium pressure liquid chromatography on silica gel. 1 H NMR spectra are reported in ppm downfield from tetramethylsilane; "s" means singlet, "d" means doublet, "dd" means doublet of doublet, "ddd" means doublet of doublet of doublet, "t" means triplet, "m" means multiplet, and "br s" means broad singlet. For mass spectral data, the number reported is the molecular weight (M) of the parent molecular ion formed by adding H+ (molecular weight of 1) to the molecule to give the M+1 peak observed by mass spectrometry using atmospheric pressure chemical ionization (AP+).

[0295] Schemes 1-8 show methods for preparing compounds of Formula 1 having various substituents. Compounds of Formula 1 having substituents other than those specifically noted for Schemes 1-8 can be prepared by general methods known in the art of synthetic organic chemistry, including methods similar to those described for Schemes 1-8.

[0296] Synthesis Example 1 Preparation of (3-(1,2,3-triazol-2-yl)-4-[(1E)-2-[4-(trifluoromethoxy)phenyl]ethenyl]pyridine) Step A: Preparation of 3-fluoro-4-[(1E)-2-[4-(trifluoromethoxy)phenyl]ethenyl]pyridine To a stirred solution of 1-(bromomethyl)-4-(trifluoromethoxy)benzene (1.449 g, 0.909 mL, 1.594 g / mL, 5.682 mmol, 1 equiv) in toluene (10 mL, 0.568 M, 6.901 vol) was added triphenylphosphine (1.49 g, 5.682 mmol, 1 equiv). The mixture was heated to reflux for 3 h. The mixture became a thick white suspension (vigorous stirring was required). At room temperature, the mixture was concentrated, and the residue was dissolved in THF (20 mL) and EtOH (2 mL). Subsequently, 3-fluoropyridine-4-carbaldehyde (0.711 g, 0.566 mL, 1.256 g / mL, 5.682 mmol, 1 equiv.) and potassium t-butoxide (1.052 g, 1.166 mL, 0.902 g / mL, 9.375 mmol, 1.65 equiv.) were added at 0° C. The reaction was stirred at 0° C. for 30 minutes, then warmed to room temperature, and stirring was continued for 5 hours. The reaction was monitored by TLC. The mixture was concentrated, then water was added, and extracted with dichloromethane. The combined organic layers were washed with water and then brine, then dried over MgSO4, filtered, and concentrated. The crude residue was subjected to chromatography (MPLC) to provide 3-fluoro-4-[(1Z)-2-[4-(trifluoromethoxy)phenyl]ethenyl]pyridine (1.1 g, 68.35%). 1 H NMR (CDCl) δ 8.45 (s, 1H), 8.23 ​​(d, 1H), 7.22 (d, 2H), 7.10 (d, 2H), 7.07 (dd, 1H), 6.87 (d, 1H), 6.59 (d, 1H) and 3-fluoro-4-[(1E)-2-[4-(trifluoromethoxy)phenyl]ethenyl]pyridine (220 mg, 13.67%). 1 H NMR(CDCl3)δ 8.47(s,1H),8.40(d,1H),7.57(d,2H),7.45(dd,1H),7.35(d,1H),7.24(d,2H),7.15(d,1).

[0297] Step B: Preparation of 3-(1,2,3-triazol-2-yl)-4-[(1E)-2-[4-(trifluoromethoxy)phenyl]ethenyl]pyridine To a stirred solution of 3-fluoro-4-[(1E)-2-[4-(trifluoromethoxy)phenyl]ethenyl]pyridine (220 mg, 0.777 mmol, equiv.) in dimethylformamide (3 mL, 0.259 M, 13.636 vol.) in a 40 mL vial was added 1H-1,2,3-triazole (0.177 g, 1.192 g / mL, 2.564 mmol, 3.3 equiv.) and cesium carbonate (0.759 g, 2.33 mmol, 3 equiv.). The solution was stirred at 105° C. for 3 h. The reaction was partitioned between water and 50% EtOAc / hexanes. The aqueous phase was extracted twice with the organic mixture. The combined organic phase was washed once with water (20 mL), followed by brine (20 mL), dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (MPLC) to give 3-(1,2,3-triazol-2-yl)-4-[(1E)-2-[4-(trifluoromethoxy)phenyl]ethenyl]pyridine (40 mg; 15.4% yield). 1 H NMR(CDCl3)δ 8.95(s,1H),8.66(d,1H),7.96(s,1H),7.69(d,1H),7.49(d,2H),7.38(d,2H),7.24(d,1H),7.21(d,2)(Compound 1).

[0298] Synthesis Example 2 Preparation of 3-chloro-5-(triazol-2-yl)-4-[2-[4-(trifluoromethyl)phenyl]ethyl]pyridine and 3-chloro-5-(triazol-1-yl)-4-[2-[4-(trifluoromethyl)phenyl]ethyl]pyridine Step A: Preparation of 4,4,5,5-tetramethyl-2-[2-[4-(trifluoromethyl)phenyl]ethyl]-1,3,2-dioxaborolane A 250 mL sealed round-bottom flask was charged with FeCl (22 mg, 0.174 mmol, 0.01 equiv.) in THF (160 mL) and degassed with argon for 5 minutes before adding 1-(trifluoromethyl)-4-vinyl-benzene (3.0 g, 17.42 mmol, 1.0 equiv.), bis-(pinacolato)-diboron (6.6 g, 26.14 mmol, 1.5 equiv.), potassium tert-butoxide (2.34 g, 20.90 mmol, 1.2 equiv.), and tert-butyl alcohol (1.64 mL, 17.14 mmol, 1.0 equiv.). The reaction mixture was stirred at 65 °C for 12 hours. The mixture was diluted with EtOAc (150 mL), washed with water (100 mL), washed with brine, and the combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the crude compound. The crude compound was purified by normal phase silica gel column chromatography using EtOAc:hexane as the eluent to give the desired compound 4,4,5,5-tetramethyl-2-[2-[4-(trifluoromethyl)-phenyl]ethyl]-1,3,2-dioxaborolane (2.2 g, yield=42%) as a white viscous liquid. 1 H NMR(CDCl3)δ 7.50(d,2H),7.30(d,2H),2.79(m,2H),1.20(s,12H),1.15(m,2H).

[0299] Step B: Preparation of 3-chloro-5-fluoro-4-[2-[4-(trifluoromethyl)phenyl]ethyl]pyridine A 100 mL round-bottom flask was charged with 3-chloro-5-fluoropyridine (700 mg, 5.34 mmol, 1.0 equiv.) and dissolved in THF (20 mL, 0.38 M, 20 vol.). The flask was cooled to −78° C., and n-BuLi (3.3 mL, 1.2 equiv., 1.9 M) was added dropwise under nitrogen. The suspension was stirred at −78° C. for 2 hours, and then 4,4,5,5-tetramethyl-2-[2-[4-(trifluoromethyl)phenyl]ethyl]-1,3,2-dioxaborolane (1.76 g, 5.87 mmol, 1.1 equiv.) in THF (15 mL, 0.76 M, 10 vol.) was added at the same temperature. The reaction mixture was stirred and maintained at −78° C. for 1 hour, then trichloroethyl chloroformate (1.5 mL, 10.68 mmol, 2.0 equiv.) was added dropwise, and the resulting solution was stirred at room temperature (25° C.) overnight. The mixture was diluted with EtOAc (20 mL) and HO (20 mL), the layers were separated, and the aqueous phase was neutralized with saturated aqueous NaHCO solution. The aqueous phase was extracted with EtOAc (20 mL × 2), and the combined organic layers were dried over MgSO, filtered, and evaporated. The residue was taken up in THF (2 mL), cooled to 0° C., and excess 50% aqueous NaOH (854 mg, 15.24 mmol, 4.0 equiv.) diluted with 2.0 mL water was added, followed by the addition of HO (2.1 mL, 26.7 mmol, 30%, 5.0 equiv.), and the mixture was stirred at room temperature (25° C.) for 12 hours. EtOAc (20 ml) was added, the layers were separated, and the aqueous phase was acidified with aqueous HCl solution (1 M) and extracted with EtOAc (20 ml × 2). The aqueous layer was neutralized with a saturated solution of NaHCO3 and extracted with EtOAc (20 ml × 2). The combined organic layers were dried over MgSO4, filtered, and evaporated to give the crude compound. The crude compound was purified by flash chromatography on silica gel using hexane:EtOAc (9:1 to 8:2) as the eluent to give the desired compound 3-chloro-5-fluoro-4-[2-[4-(trifluoromethyl)phenyl]ethyl]-pyridine (500 mg, 31%) as a yellow viscous liquid.1H NMR(CDCl3)δ 8.40(s,1H),8.30(s,1H),7.54(d,2H),7.29(d,2H),3.10(m,2H),2.94(m,2H).

[0300] Step C: Preparation of 3-chloro-5-(triazol-2-yl)-4-[2-[4-(trifluoromethyl)phenyl]ethyl]pyridine and 3-chloro-5-(triazol-1-yl)-4-[2-[4-(trifluoromethyl)phenyl]ethyl]pyridine In a 25 mL sealed tube, 3-chloro-5-fluoro-4-[2-[4-(trifluoromethyl)phenyl]ethyl]pyridine (250 mg, 0.80 mmol) in DMF (2 mL) was added, and CsCO (781 mg, 2.4 mmol, 3.0 equiv.) was added, followed by 1,2,3-triazole (81.69 mg, 1.21 mmol, 1.5 equiv.). The reaction mixture was stirred overnight at 95 °C for 20 h. After complete consumption of the starting material, monitored by TLC, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous NaSO, concentrated, and purified by Combi-Flash column using 20–70% ethyl acetate in hexane as eluent to give the desired product, 3-chloro-5-(triazol-2-yl)-4-[2-[4-(trifluoromethyl)phenyl]ethyl]pyridine (60 mg), as a pale yellow solid. H NMR (CDCl) δ 8.76 (s, 1H), 8.66 (s, 1H), 7.92 (s, 2H), 7.51 (d, 2H), 7.26 (d, 2H), 3.16 (m, 2H), 2.98 (m, 2H) (compound 8). 3-Chloro-5-(triazol-1-yl)-4-[2-[4-(trifluoromethyl)phenyl]ethyl]pyridine (50 mg) was obtained as an off-white solid. H NMR (CDCl) δ 8.75 (s, 1H), 8.42 (s, 1H), 7.86 (s, 1H), 7.52 (s, 1H), 7.47 (d, 2H), 7.14 (d, 2H), 2.96 (s, br. 4H) (compound 9).

[0301] Synthesis Example 3 Preparation of 3-fluoro-5-(triazol-1-yl)-4-[2-[4-(trifluoromethyl)phenyl]cyclopropyl]pyridine and (3-fluoro-5-(triazol-2-yl)-4-[2-[4-(trifluoromethyl)phenyl]cyclopropyl]pyridine Step A: Preparation of 3,5-difluoro-4-[2-[4-(trifluoromethyl)phenyl]cyclopropyl]pyridine A 100 mL sealed round-bottom flask was charged with 3,5-difluoropyridine-4-carbaldehyde (1) (1.0 g, 6.99 mmol, 1.0 equiv.) and 4-methylbenzenesulfonohydrazide (2) (1.3 g, 6.99 mmol, 1.0 equiv.) in dioxane (10 mL) and heated to 70 °C for 1 h. After complete consumption of the starting material, as monitored by TLC, additional 1-(trifluoromethyl)-4-vinyl-benzene (B) (2.0 mL, 13.98 mmol, 2.0 equiv.) and KCO (1.5 g, 10.48 mmol, 1.5 equiv.) were added, and heating was continued at 110 °C for 6 h. After complete consumption of the starting material, as monitored by TLC, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated, and purified by Combi-Flash column chromatography using 20-70% ethyl acetate in hexane to give 3,5-difluoro-4-[2-[4-(trifluoromethyl)phenyl]cyclopropyl]pyridine as a brown viscous liquid (790 mg, 39%). 1H NMR (CDCl3) δ 8.25 (s, br. 1.38H), 8.08 (s, br. 0.62H), 7.56 (d, br. 1.42H), 7.36 (d, br. 0.58H), 7.28 (d, br. 1.42H), 7.06 (d, br. 0.58H), 1.57-2.76 (m, 4H).

[0302] Step B: Preparation of 3-fluoro-5-(triazol-1-yl)-4-[2-[4-(trifluoromethyl)phenyl]cyclopropyl]pyridine and (3-fluoro-5-(triazol-2-yl)-4-[2-[4-(trifluoromethyl)phenyl]cyclopropyl]pyridine In a 25 mL sealed tube, 3,5-difluoro-4-[2-[4-(trifluoromethyl)phenyl]cyclopropyl]pyridine (404 mg, 1.35 mmol) was placed. In DMF (2 mL), CsCO (440 mg, 1.35 mmol, 1.0 equiv.) was added, followed by 1,2,3-triazole (100 mg, 1.35 mmol, 1.0 equiv.), and the reaction mixture was stirred and placed in a microwave at 80 °C for 1 hour. After complete consumption of the starting material, monitored by TLC, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous NaSO, concentrated and purified by Combi-flash column using 20-70% ethyl acetate / hexane as eluent to give the desired compound 3-fluoro-5-(triazol-1-yl)-4-[2-[4-(trifluoromethyl)phenyl]cyclopropyl]pyridine (28.8 mg) as a white solid. 1H NMR (CDCl3) δ 8.59 (s, 1H), 8.50 (s, 1H), 7.82 (s, 1H), 7.78 (s, 1H), 7.50 (d, 2H), 7.07 (d, 2H), 2.33 (m, 1H), 1.99 (m, 1H), 1.45 (m, 2H) (compound 3); and 3-fluoro-5-(triazol-2-yl)-4-[2-[4-(trifluoromethyl)phenyl]cyclopropyl]pyridine (27.3 mg) as an off-white solid. 1H NMR (CDCl3) δ 8.66(s,1H),8.52(s,1H),7.77(s,2H),7.49(s,2H),7.07(d,2H),2.36(m,1H),2.17(m,1H),1.39(m,2H)(Compound 4).

[0303] By the procedures described herein together with methods known in the art, the following compounds in Tables 1-70N can be prepared. The following abbreviations are used in the tables below: t means tertiary, s means secondary, n means normal, i means iso, c means cyclo, Me means methyl, Et means ethyl, Pr means propyl, i-Pr means isopropyl, Bu means butyl, Ph means phenyl, OMe means methoxy, OEt means ethoxy, SMe means methylthio, SEt means ethylthio, -CN means cyano, Ph means phenyl, Py means pyridinyl, -NO means nitro, TMS means trimethylsilyl, S(O)Me means methylsulfinyl, and S(O)Me means methylsulfonyl.

[0304] Fragments Q-1 to Q-19 shown below are referred to in Table 1A. Appendix 3 shows the structures of fragments Q-1 to Q-19. The wavy line indicates the point of attachment of the fragment to the rest of the molecule.

[0305] Appendix 3 [ka] [ka]

[0306] Tables 1A-70. Pertaining to the structures shown below. [ka]

[0307] Table 1A L is -CH=CH-, A is CH, and R 2 is H and R 5 is H.

[0308] [Table 1]

[0309] [Table 2]

[0310] This disclosure also includes Tables 2A-70A, each of which is structured similarly to the preceding Table 1A, except that the row headings in Table 1A under the Markush structure (i.e., "A is CH and R 4 is H and R 5 is H") is replaced with the respective row heading shown below. For example, in Table 2A, the row heading is "L is -CH=CH-, A is CF, R 4 is H and R 5 is H and Q is as defined in Table 1A above." Thus, the first entry in Table 2A specifically discloses 4-[2-(4-chlorophenyl)vinyl]-3-fluoro-5-(triazol-2-yl)pyridine.

[0311] [Table 3]

[0312] [Table 4]

[0313] [Table 5]

[0314] Table 1B Table 1B is identical to Table 1A, except that the chemical structures in the Table 1B headings are replaced with the following structures: [ka]

[0315] For example, the first compound in Table 1B has the structure shown immediately above, where L is —CH═CH—, A is CH, and R2 is H and R 5 is H and Q is 4-chlorophenyl.

[0316] Tables 2B~70B Tables 2B-70B are constructed in the same manner as Tables 2A-70A.

[0317] Table 1C Table 1C is identical to Table 1A, except that the chemical structures in the Table 1B headings are replaced with the following structures: [ka]

[0318] For example, the first compound in Table 1C has the structure shown immediately above, where L is —CH═CH—, A is CH, and R 2 is H and R 5 is H and Q is 4-chlorophenyl.

[0319] Table 2C~70C Tables 2C-70C are constructed in the same manner as Tables 2A-70A.

[0320] Table 1D Table 1D is identical to Table 1A, except that the chemical structures in the Table 1D headings are replaced with the following structures: [ka]

[0321] For example, the first compound in Table 1D has the structure shown immediately above, where L is —CH═CH—, A is CH, and R 2 is H and R 5 is H and Q is 4-chlorophenyl.

[0322] Table 2D~70D Tables 2D-70D are constructed in the same manner as Tables 2A-70A.

[0323] Table 1E Table 1E is identical to Table 1A, except that the chemical structures in the Table 1E headings are replaced with the following structures: [ka]

[0324] For example, the first compound in Table 1D has the structure shown immediately above, where L is —CH═CH—, A is CH, and R 2 is H and R 5 is H and Q is 4-chlorophenyl.

[0325] Table 2E~70E Tables 2E-70E are constructed in a similar manner to Tables 2A-70A.

[0326] Table 1F Table 1F is identical to Table 1A, except that the chemical structures in the Table 1F headings are replaced with the following structures: [ka]

[0327] For example, the first compound in Table 1F has the structure shown immediately above, where L is —CH═CH—, A is CH, and R 2 is H and R 5 is H and Q is 4-chlorophenyl.

[0328] Table 2F~70F Tables 2F-70F are constructed in a similar manner to Tables 2A-70A.

[0329] Table 1G Table 1G is identical to Table 1A, except that the chemical structures in the Table 1G headings are replaced with the following structures: [ka]

[0330] For example, the first compound in Table 1G has the structure shown immediately above, where L is —CH═CH—, A is CH, R 2 is H and R 5 is H and Q is 4-chlorophenyl.

[0331] Table 2G~70G Tables 2G-70G are constructed in a similar manner to Tables 2A-70A.

[0332] Table 1H Table 1H is identical to Table 1A, except that the chemical structures in the Table 1H headings are replaced with the following structures: [ka]

[0333] For example, the first compound in Table 1H has the structure shown immediately above, where L is —CH═CH—, A is CH, and R 2 is H and R 5 is H and Q is 4-chlorophenyl.

[0334] Table 2H~70H Tables 2H-70H are constructed in the same manner as Tables 2A-70A.

[0335] Table 1I Table 1I is identical to Table 1A, except that the chemical structure under the Table 1H heading is replaced with the following structure: [ka]

[0336] For example, the first compound in Table 1I has the structure shown immediately above, where L is —CH═CH—, A is CH, and R 2 is H and R 5 is H and Q is 4-chlorophenyl.

[0337] Tables 2I~70I Tables 2I-70I are constructed in a similar manner to Tables 2A-70A.

[0338] Table 1J Table 1J is identical to Table 1A, except that the chemical structures in the Table 1J headings are replaced with the following structures: [ka]

[0339] For example, the first compound in Table 1H has the structure shown immediately above, where L is —CH═CH—, A is CH, and R 2 is H and R 5 is H and Q is 4-chlorophenyl.

[0340] Table 2J~70J Tables 2J-70J are constructed in a similar manner to Tables 2A-70A.

[0341] Table 1K Table 1K is identical to Table 1A, except that the chemical structures in the Table 1K headings are replaced with the following structures: [ka]

[0342] For example, the first compound in Table 1K has the structure shown immediately above, where L is —CH═CH—, A is CH, and R 2 is H and R 5 is H and Q is 4-chlorophenyl.

[0343] Table 2K~70K Tables 2K-70K are constructed in the same manner as Tables 2A-70A.

[0344] Table 1L Table 1L is identical to Table 1A, except that the chemical structures in the Table 1L headings are replaced with the following structures: [ka]

[0345] For example, the first compound in Table 1L has the structure shown immediately above, where L is —CH═CH—, A is CH, and R 2 is H and R 5 is H and Q is 4-chlorophenyl.

[0346] Table 2L~70L Tables 2L-70L are constructed in the same manner as Tables 2A-70A.

[0347] Table 1M Table 1M is identical to Table 1A, except that the chemical structures in the Table 1M headings are replaced with the following structures: [ka]

[0348] For example, the first compound in Table 1M has the structure shown immediately above, where L is —CH═CH—, A is CH, and R 2 is H and R 5 is H and Q is 4-chlorophenyl.

[0349] Table 2M~70M Tables 2M-70M are constructed in the same manner as Tables 2A-70A.

[0350] Table 1N Table 1N is identical to Table 1A, except that the chemical structures in the Table 1N headings are replaced with the following structures: [ka]

[0351] For example, the first compound in Table 1N has the structure shown immediately above, where L is —CH═CH—, A is CH, and R 2 is H, R5 is H, and Q is 4-chlorophenyl.

[0352] Table 2N~70N Tables 2N-70N are constructed in the same manner as Tables 2A-70A.

[0353] The compounds of the present disclosure will generally be used as the invertebrate pest control active ingredient in a composition, i.e., a formulation, with at least one additional ingredient selected from the group consisting of surfactants, solid diluents, and liquid diluents, which act as a carrier. The ingredients of the formulation or composition are selected to suit the physical properties of the active ingredient, the application form, and environmental factors such as soil type, moisture, and temperature.

[0354] Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, and emulsions (including microemulsions, oil-in-water emulsions, flowable concentrates, and / or suspoemulsions), which can optionally be thickened into 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.

[0355] Common types of solid compositions include dusts, powders, granules, pellets, prills, pastilles, tablets, and filler 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 formed into suspension 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.

[0356] 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 are more typically in the range of 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 metered directly into drip irrigation systems or into furrows during planting. Liquid and solid formulations can be applied to crop seeds and other desirable vegetation as seed treatments before planting to protect developing roots and other underground plant parts and / or foliage via systemic absorption.

[0357] The formulations will typically contain effective amounts of active ingredients, diluents, and surfactants within the following approximate ranges, which add up to 100 weight percent:

[0358] [Table 6]

[0359] Solid diluents include, for example, 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.

[0360] 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-pentanone, and Acetates such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate, and isobornyl acetate, other esters such as alkylated lactate esters, dibasic esters, alkyl and aryl benzoates, γ-butyrolactone, and alcohols that can be linear, branched, saturated, or unsaturated, such as methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, cresol, and benzyl alcohol. Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C6-C8). 22Liquid diluents 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, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated), which 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.

[0361] The solid and liquid compositions of the present disclosure 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.

[0362] Surfactants can be classified as nonionic, anionic, or cationic. Nonionic surfactants useful in 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 with 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 rivers in which the end blocks are prepared from propylene oxide. ethoxylated 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.

[0363] 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 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; sulfosuccinamates; and sulfosuccinates and their derivatives, such as dialkyl sulfosuccinate salts.

[0364] 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.

[0365] 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.

[0366] The compositions of the present disclosure may also 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 (buffers), foaming during processing (antifoaming agents such as polyorganosiloxanes), active ingredient settling (suspending agents), viscosity (thixotropic thickeners), microbial growth in the container (antibacterial 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 WO 03 / 024222.

[0367] The compound of Formula 1 and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredients in a solvent or by grinding them 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 water-immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Active ingredient slurries with 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 to produce an average particle size in the 2-10 μm range. Dusts and powders can be prepared by blending and usually milling (such as with a hammer mill or fluid energy mill). 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 et seq.; and 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 DE 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.

[0368] 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. Also see 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 See also Publications, Richmond, UK, 2000.

[0369] 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 those skilled in the art can use the preceding description to make the most of this disclosure. Therefore, the following examples are merely intended as illustrative and do not limit the present disclosure in any way. Percentages are by weight unless otherwise specified.

[0370] The compounds of the present disclosure exhibit activity 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, building structures, or animal skins. These pests include invertebrates that cause damage or harm to, for example, growing and stored agricultural crops, forests, greenhouse crops, ornamental plants, nursery crops, stored food or textile products, or homes or other structures or components thereof, or are harmful to animal or public health, by feeding on, for example, foliage (including leaves, stems, flowers, and fruit), seeds, wood, textiles, or animal blood or tissues. Those skilled in the art will understand that not all compounds are equally effective against all developmental stages of all pests.

[0371] Thus, these compounds and compositions are agronomically useful for protecting agricultural crops from herbivorous invertebrate pests, and also non-agronomically useful for protecting other horticultural crops and plants from herbivorous invertebrate pests. This utility includes protecting crops and other plants (i.e., both agronomic and non-agronomic) that contain genetic material introduced by genetic engineering (i.e., gene transfer) or modified by mutagenesis to confer advantageous traits. Examples of such traits include herbicide tolerance, 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 yields, 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 resistance to glyphosate herbicides or contain the HRA gene to provide resistance to herbicides that inhibit acetolactate synthase (ALS). The compounds and compositions may exhibit enhanced effects due to traits introduced by genetic engineering or modified by mutagenesis, thereby enhancing the phenotypic expression or efficacy of the trait or increasing the invertebrate pest control efficacy of the 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 the pests.

[0372] 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 disclosure 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, can be prepared by mixing the compounds or compositions of the present disclosure and the fertilizer composition together with the formulation ingredients, and then preparing the formulation by methods such as granulation or extrusion. Alternatively, solid formulations can be prepared by spraying a solution or suspension of the compounds or compositions of the present disclosure 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.

[0373] Non-agricultural uses refer to invertebrate pest control in areas other than crop plant fields. Non-agricultural uses of the present compounds and compositions include invertebrate pest control in stored grains, legumes, and other foods, and textiles such as clothing and carpets. Non-agricultural uses of the present compounds and compositions also include invertebrate pest control in ornamental plants, forests, gardens, roadsides, and railroad rights-of-way, as well as turf such as lawns, golf courses, and pastures. Non-agricultural uses of the present compounds and compositions also include invertebrate pest control 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.

[0374] Non-agricultural uses of the compounds and compositions also include protecting human and animal health by controlling and eliminating invertebrate pests that are parasitic or transmit infectious diseases. Control and elimination of animal parasites includes controlling and eliminating ectoparasites that infest the surface of the host animal's body (e.g., shoulders, armpits, abdomen, inner thighs) and endoparasites that infest the host animal's body (e.g., stomach, intestines, lungs, veins, subcutaneous tissue, lymphatic tissue). Externally parasitic pests or disease-transmitting pests include, for example, chiggers, ticks, lice, mosquitoes, flies, mites, and fleas. Endoparasites include heartworms, hookworms, and parasitic helminths. The compounds and compositions of the present disclosure are suitable for systemic and / or non-systemic control of parasitic infestations or infections in animals. The compounds and compositions of the present disclosure are particularly suitable for combating external parasites or disease-transmitting pests.The compounds and compositions of the present disclosure are suitable for eliminating the parasites that infest agricultural working animals, such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, hens, turkeys, ducks, geese, and bees; pet animals and livestock animals, such as dogs, cats, pet birds, and ornamental fish; and so-called laboratory animals, such as hamsters, guinea pigs, rats, and mice.By eliminating these parasites, mortality and performance loss (for meat, milk, wool, skin, eggs, honey, etc.) are reduced, so that the use of compositions containing the compounds of the present disclosure makes it possible to make animal husbandry more economical and simple.

[0375] Examples of agronomic and non-agronomic invertebrate pests include the order Lepidoptera, e.g., cutworms, cutworms, and heliothines in the family Noctuidae (e.g., Sesamia inferens Walker, Sesamia nonagrioides Lefebvre, Spodoptera eridania Cramer, Spodoptera frugiperda JESmith, Spodoptera exigua Huebner, Spodoptera littoralis Boisduval, Spodoptera ornithogalli Guenee, Agrotis ipsilon Hufnagel, Anticarsia gemataris, etc.). gemmatalis Huebner), Lithophane antennata Walker, Armyworm moth (Barathra brassicae Linnaeus), Soybean looper (Pseudoplusia includens Walker), Nettle looper moth (Trichoplusia ni Huebner), Tobacco budworm (Heliothis virescens Fabricius);Borers, case bearers, webworms, cornworms, cabbage worms, and skeletonizers from the Pyralidae family (e.g., European corn borer (Ostrinia nubilalis Huebner), navel orangeworm (Amyelois transitella Walker), Crambus caliginosellus Clemens), sod webworms (Pyralidae: Crambinae) such as Herpetogramma licarsisalis Walker, night cricket moth (Chilo infuscatellus Snellen), Neoleucinodes elegantalis Guenee, rice leaf borer (Cnaphalocrocis medinalis Guenee), Desmia funeralis Huebner, American cucumber borer (Diaphania nitidalis Stoll), Hellula hydralis (Hellula hydralis Guenee), Scirpophaga incertulas Walker, Scirpophaga innotata Walker, Scirpophaga nivella Fabricius, Chilo polychrysus Meyrick, Chilo suppressalis Walker, Crocidolomia binotalis Zeller);Leaf rollers, budworms, seedworms, and fruitworms in the Tortricidae family (e.g., codling moth (Cydia pomonella Linnaeus), Paralobesia viteana (Clemens), pear fruit moth (Grapholita molesta Busck), Cryptophlebia leucotreta (Meyrick), Gymnandrosoma aurantianum (Lima), red-banded moth (Argyrotaenia velutinana Walker), lotus-banded moth (Choristoneura rosaceana Harris), apple-brown moth (Epiphyas postvittana Walker), grape-leaf moth (Eupoecilia ambiguella Huebner), Pandemis pyrusana Kearfott), Platynota stultana (Walsingham), Pandemis cerasana (Huebner), Pandemis heparana (Denis & Schiffermueller);and many other economically important Lepidoptera (e.g., Plutella xylostella Linnaeus, Pectinophora gossypiella Saunders, Lymantria dispar Linnaeus, Carposina niponensis Walsingham, Anarsia lineatella Zeller, Phthorimaea operculella Zeller, Phyllonorycter blancardella Fabricius, Lithocolletis ringoniella Matsumura, Lerodea eufala Edwards, Leucoptera scitella Zeller) eggs, larvae, and adults; the order Blattodea, including cockroaches from the families Blattidae and Blattidae (e.g., Asian cockroach (Blatta orientalis Linnaeus), Okinawan German cockroach (Blatella asahinai Mizukubo), German cockroach (Blattella germanica Linnaeus), Brown-striped cockroach (Supella longipalpa Fabricius), American cockroach (Periplaneta americana Linnaeus), Brown brown cockroach (Periplaneta brunnea Burmeister), Madera cockroach (Leucophaea maderae Fabricius), Smoked cockroach (Periplaneta fuliginosa Serville), American cockroach (Periplaneta australasiae Fabr.), and Brown cockroach (Nauphoeta cinerea) Olivier), and dusky wood cockroach (Symploce pallens Stephens) eggs, nymphs, and adults;Coleoptera, including weevils from the families Pseudocercoides, Bruchidae, and Curculionidae (e.g., Anthonomus grandis Boheman, Lissorhoptrus oryzophilus Kuschel, Sitophilus granarius Linnaeus, Sitophilus oryzae Linnaeus), Listronotus maculicollis Dietz, Sphenophorus parvulus Gyllenhal, Sphenophorus venatus vestitus Chittenden, Denverville bug Sphenophorus cicatristriatus eggs, foliar-feeding, fruit-feeding, root-feeding, seed-feeding, and vesicular-feeding larvae and adults of the family Chrysomelidae; spring beetles, cucumber beetles, rootworms, potato beetles, and leaf miners (e.g., Colorado potato beetle (Leptinotarsa ​​decemlineata Say), Western corn rootworm (Diabrotica virgifera LeConte));Scarab beetles and other beetles from the family Scarabaeidae (e.g., Japanese beetle (Popillia japonica Newman), Japanese scarab beetle (Anomala orientalis Waterhouse), Cyclocephala borealis Arrow, Cyclocephala immaculata or C. lurida Bland), dung beetles and grubs (Aphodius spp.), Ataenius spretulus Haldeman, Green June beetle (Cotinis nitida Linnaeus), Red-billed scarab beetle (Maladera castanea Arrow), scarab beetles (Phyllophaga spp.), and European chafer (Rhizotrogus majalis Razoumowsky); Dermestidae beetles; wireworms; bark beetles; and flower beetles.

[0376] Additionally, as agronomic and non-agronomic pests: Dermoptera, including earwigs from the family Dermoptera (e.g., eggs, adults, and larvae of Forficula auricularia Linnaeus, Chelisoches morio Fabricius); Hemiptera, including earwigs from the family Miridae, cicadas from the family Cicadidae, leafhoppers from the family Cicadellidae (e.g., Empoasca spp.), bedbugs from the family Cimicidae (e.g., Cimex lectularius). Linnaeus), planthoppers from the families Delphacidae and Delphacidae, treehoppers from the family Ceroplastidae, psyllids from the families Psyllidae, Psyllidae, and Trichobrachidae, whiteflies from the family Aleyrodidae, aphids from the family Aphididae, root aphids from the family Phyllopidae, mealybugs from the family Pseudococcidae, scale insects from the families Coccidae, Diaspididae, and Pseudococcidae, scale bugs from the family Tingidae, stink bugs from the family Hemiptera, stink bugs from the family Lygaeidae (e.g., Blissus leucopterus hirtus Montandon and Blissus insularis Barber), and other seed bugs, egg, juvenile, adult, and nymph forms of spit bugs from the Spitidae family, corner bugs from the Coreidae family, and red bugs and spotted bugs from the Pyrrhocoridae family.

[0377] Also, as agronomic and non-agronomic pests: Acari (mites), for example spider mites and red mites in the Tetranychidae family (e.g., Panonychus ulmi Koch, Tetranychus urticae Koch, Tetranychus mcdanieli McGregor); flat mites in the Ornithine family (e.g., Brevipalpus lewisi McGregor); rust and badomite in the Eriophyidae family, as well as other foliar-feeding mites, and mites of importance in human and animal health, i.e., dust mites in the Pteromychidae family, follicul mites in the Demodex family, grain mites in the Sarcophagidae family, ticks (commonly known as hard ticks) in the Ixodidae family (e.g., deer ticks (Ixodes scapularis Say), Australian ixodid ticks (Ixodes holocyclus Neumann, Dermacentor variabilis Say, Amblyomma americanum Linnaeus), and mites in the Argiidae family (commonly known as soft ticks) (e.g., Ornithodoros turicata Duges, Argas radiatus Raillet); eggs, larvae, nymphs, and adults of scab and itch mites in the families Psammida, Acaridae, and Sarcoptidae;Orthoptera, including grasshoppers, locusts, and crickets (e.g., migrative grasshoppers (e.g., Melanoplus sanguinipes Fabricius, M. diferentialis Thomas), American grasshoppers (e.g., Schistocerca americana Drury), desert locusts (Schistocerca gregaria Forsskol), migratory locusts (Locusta migratoria Linnaeus), bush locusts (Zonocerus spp.), European house crickets (Acheta domesticus Linnaeus), mole crickets (e.g., Scapteriscus vicinus Scudder, and Scapteriscus borellii) Giglio-Tos)) eggs, adults, and nymphs;Leaf miners (e.g., Liriomyza spp., e.g., Liriomyza sativae Blanchard), midges, fruit flies (Tephritidae), frit flies (e.g., Oscinella frit Linnaeus), soil maggots, house flies (e.g., Musca domestica Linnaeus), lesser house flies (e.g., Fannia canicularis Linnaeus, Fannia 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.), bottom flies (e.g., Gasterophilus spp., Oestrus spp.), cuttle flies (e.g., Hypoderma spp.), deer flies (e.g., Chrysops spp.), keds (e.g., Melophagus ovinus), and other muscoid fly pests. eggs, adults, and nymphs of Diptera, including other Diptera, mosquitoes (e.g., Aedes spp., Anopheles spp., Culex spp.), blackflies (e.g., Prosimulium spp., Simulium spp.), biting midges, sand flies, susialids, and other Culicidae; eggs, adults, and nymphs of Thripida, including onion thrips (Thrips tabaci Lindeman), flower thrips (Frankliniella spp.), and other foliar-feeding thrips;Florida carpenter ant (Camponotus floridanus Buckley), red carpenter ant (Camponotus ferrugineus Fabricius), Japanese carpenter ant (Camponotus pennsylvanicus De Geer), white-legged flat-footed ant (Technomyrmex albipes F. Smith), shiny house ant (Pheidole spp.), brown sand ant (Tapinoma melanocephalum Fabricius); house ant (Monomorium pharaonis Linnaeus), little fire ant (Wasmannia auropunctata Roger), red fire ant (Solenopsis geminata Fabricius), Japanese fire ant (Solenopsis invicta Buren), Argentine ant (Iridomyrmex humilis Mayr), long-horned fire ant (Paratrechina longicornis Latreille), brown sand ant (Tetramorium Insect pests of the Hymenoptera, including ants of the Formicidae family, including Lasius caespitum Linnaeus, Lasius alienus Foerster, and Tapinoma sessile Say. Other Hymenoptera, including honeybees (including carpenter bees), hornets, yellow jackets, digger wasps, and sawflies (Neodiprion spp.; Cephus spp.);Termitidae (e.g., Macrotermes spp., Odontotermes obesus Rambur), Calotermitidae (e.g., Cryptotermes spp.), and Rhinotermitidae (e.g., Reticulitermes spp., Coptotermes spp., Heterotermes tenuis Hagen), Reticulitermes flavipes Kollar, Reticulitermes hesperus Banks, Coptotermes formosanus Shiraki, Incisitermes immigrans Snyder, Cryptotermes brevis Insect pests of the order Isoptera, including Incisitermes Walker, Incisitermes snyderi Light, Reticulitermes virginicus Banks, Incisitermes minor Hagen, arboreal termites, such as termites in the genus Nasutitermes, and other economically important termites; insect pests of the order Thymidera, such as the silverfish Lepisma saccharina Linnaeus and the spotted silverfish Thermobia domestica Packard;Insect pests of the orders Phthiraptera and Phthiraptera, including the head louse (Pediculus humanus capitis De Geer), human louse (Pediculus humanus Linnaeus), chicken body louse (Menacanthus stramineus Nitzsch), dog body louse (Trichodectes canis De Geer), Goniocotes gallinae De Geer, sheep body louse (Bovicola ovis Schrank), cattle louse (Haematopinus eurysternus Nitzsch), cattle lice (Linognathus vituli Linnaeus), and other sucking, chewing parasitic lice that attack humans and animals; Insect pests of the order Siphonaptera, including the dog flea (Ctenocephalides canis Curtis), the bird flea (Ceratophyllus gallinae Schrank), the chicken lift flea (Echidnophaga gallinacea Westwood), the human flea (Pulex irritans Linnaeus), and other fleas that infest mammals and birds. Additional arthropod pests included are spiders of the order Araneae, such as the brown recluse spider (Loxosceles reclusa Gertsch & Mulaik) and the black widow spider (Latrodectus mactans Fabricius), and centipedes of the order Scutigera, such as Scutigera coleoptrata Linnaeus;

[0378] Examples of invertebrate pests of stored grain include Prostephanus truncatus Horn, Rhyzopertha dominica Fabricius, Sitophilus oryzae Linnaeus, Sitophilus zeamais Motschulsky, Callosobruchus maculatus Fabricius, Tribolium castaneum Herbst, Sitophilus granarius Linnaeus, Plodia interpunctella Huebner, Ephestia kuehniella Zeller, and Cryptolestes ferrugineus Stephens.

[0379] The compounds of the present disclosure are effective against, but are not limited to, economically important agricultural pests (i.e., root-knot nematodes in the genus Meloidogyne, root-lesion nematodes in the genus Pratylenchus, and branch nematodes in the genus Trichodorus), as well as animal and human health pests (i.e., Strongylus vulgaris in horses, Toxocara canis in dogs, Haemonchus contortus in sheep, Dirofilaria immitis Leidy in dogs, Anoplocephala perfoliata in horses, Fasciola hepatica in ruminants, and the like). The compounds may have activity against members of the classes Nematoda, Cestoda, Trematoda, and Acanthocephala, including economically important members of the orders Strongyloides, Ascarida, Enterobiida, Rhabdochida, Spiruura, and Enobridae, all economically important trematodes, cestodes, and roundworms such as Echinococcus esculentus (Echinococcus esculentus), ...

[0380] The compounds of the disclosure are effective against pests in the order Lepidoptera, such as 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), Cnaphalocrocis medinalis Guenee (rice leafroller), Crambus caliginosellus Clemens (corn root webworm), Crambus teterrellus Zincken (bluegrass webworm), Cydia pomonella Linnaeus (codling moth), Earias insulana Boisduval (missing cotton moth), Earias vittella Fabricius (weed banded moth), Helicoverpa armigera Huebner (cotton bollworm), Helicoverpa zea Boddie (tobacco moth), Heliothis virescens Fabricius (false cotton moth), Herpetogramma licarsisalis Walker (black-banded black moth), Lobesia botrana Denis & Schiffermueller (leaved tortrix moth), Pectinophora gossypiella Saunders (pink bollworm), Phyllocnistis citrella Stainton (citrus leafminer), Pieris brassicaeIt may have activity against the following insecticides: Pieris rapae Linnaeus (cabbage white butterfly), Plutella xylostella Linnaeus (diamond moth), Spodoptera exigua Huebner (beet armyworm), Spodoptera litura Fabricius (common cutworm), Spodoptera frugiperda J. E. Smith (stalk armyworm), Trichoplusia ni Huebner (nettle looper), and Tuta absoluta Meyrick (tomato tuber moth).

[0381] The compounds of the present disclosure are effective against: Acyrthosiphon pisum Harris (pea aphid), Aphis craccivora Koch (bean aphid), Aphis fabae Scopoli (black bean aphid), Aphis gossypii Glover (cotton aphid), Aphis pomi De Geer (apple aphid), Aphis spiraecola Patch (spiny willow aphid), Aulacorthum solani Kaltenbach (potato aphid), Chaetosiphon fragaefolii Cockerell (locust aphid), Diuraphis noxia Kurdjumov / Mordvilko (Russian wheat aphid), Dysaphis plantaginea Passerini (plantain aphid), Eriosoma lanigerum Hausmann (apple aphid), Hyalopterus pruni Geoffroy (peach buttercup aphid), Lipaphis pseudobrassicae Davis (false radish aphid), Metopolophium dirrhodum Walker (cereal aphid), Macrosiphum euphorbiae Thomas (tulip aphid), Myzus persicae Sulzer (peach aphid), Nasonovia ribisnigri Mosley (lettuce aphid), Pemphigus species (root and gall aphids), Rhopalosiphum maidisFitch (corn aphid), Rhopalosiphum padi Linnaeus (wheat neck aphid), Schizaphis graminum Rondani (wheat green aphid), Sitobion avenae Fabricius (wheat long-horn aphid), Therioaphis maculata Buckton (spotted alfalfa aphid), Toxoptera aurantii Boyer de Fonscolombe (cowcan aphid), and Toxoptera citricidus Kirkaldy (citrus black aphid); Adelges species (adeligids); Phylloxera devastatrix Pergande (pecan aphid); Bemisia tabaci Gennadius (tobacco whitefly), Bemisia argentifolii Bellows & Perring (silverleaf whitefly), Dialeurodes citri Ashmead (citrus whitefly), and Trialeurodes vaporariorum Westwood (greenhouse whitefly); Empoasca fabae Harris (potato leafhopper), Laodelphax striatellus Fallen (small brown planthopper), Macrosteles quadrilineatus Forbes (two-legged leafhopper), Nephotettix cincticeps Uhler (green rice leafhopper), Nephotettix nigropictus Stol (black-striped rice leafhopper), Nilaparvata lugensStol (brown planthopper), Peregrinus maidis Ashmead (corn planthopper), Sogatella furcifera Horvath (white-backed planthopper), Tagosodes orizicolus Muir (rice delphacid), Typhlocyba pomaria McAtee (white apple leafhopper), Erythroneura spp. (grape leafhopper); Magicidada septendecim Linnaeus (yearling cicada); Icerya purchasi Maskell (Icerya scale insect), Quadraspidiotus perniciosus It has great activity against members of the Hemiptera order, including Pseudococcus spp. (pear scale); Pseudococcus citri Risso (citrus mealybug); Pseudococcus species (other mealybug complex); Cacopsylla pyricola Foerster (two-spotted psylla), and Trioza diospyri Ashmead (oyster psylla).

[0382] The compounds of the present disclosure are also effective against: Acrosternum hilare Say (green grass bug), Anasa tristis De Geer (helicopter bug), Blissus leucopterus leucopterus Say (American long-horned stink bug), Cimex lectularius Linnaeus (bed bug), Corythucha gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), Dysdercus suturellus Herrich-Schaeffer (cotton stainer), Euschistus servus Say (Brown Stink Bug), Euschistus variolarius Palisot de Beauvois (One-Spotted Stink Bug), Graptostethus spp. (Seed Bug Complex), Halyomorpha halys Stol (Marbled Stink Bug), Leptoglossus corculus Say (Leaf-Footed Pine Seed Bug), Lygus lineolaris Palisot de Beauvois (Green Mirid Bug), Nezara viridula Linnaeus (Southern Green Stink Bug), Oebalus pugnax It has activity against members from the order Hemiptera, including Oncopeltus fasciatus Dallas (large milkweed bug), Pseudatomoscelis seriatus Reuter (cotton flea beetle), and Rhizopus nigricans (rice bug).Other insect orders controlled by the compounds of the present disclosure include Thysanoptera (e.g., Frankliniella occidentalis Pergande (Occidental flower thrips), Scirtothrips citri (Cigar thrips), Scirtothrips variabilis Beach (Soybean thrips), and Thrips tabaci Lindeman (Onion thrips)); and Coleoptera (e.g., Leptinotarsa ​​decemlineata Say (Colorado potato beetle), Epilachna varivestis (Leptinotarsa ​​decemlineata Say (Colorado potato beetle), Epilachna varivestis (Leptinotarsa ​​decemlineata Say (Colorado potato beetle)), and Coleoptera (e.g., Coleoptera spp.)). Mulsant (heart beetles), and wireworms of the genera Agriotes, Athous, or Limonius.

[0383] Of note is the use of a compound of the present invention to control and eliminate western flower thrips (Frankliniella occidentalis). Of note is the use of a compound of the present invention to control and eliminate potato leafhoppers (Empoasca fabae). Of note is the use of a compound of the present invention to control and eliminate cotton aphids (Aphis gossypii). Of note is the use of a compound of the present invention to control and eliminate green peach aphids (Myzus persicae). Of note is the use of a compound of the present invention to control and eliminate tobacco whiteflies (Bemisia tabaci).

[0384] The compounds of the present disclosure 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 as a formulated composition. The compound of Formula 1 is often applied directly to the crop plant or its seed, but it can also be applied to the locus of the crop plant, i.e., to a portion of the environment of the crop plant, particularly one sufficiently close to the environment for the compound of Formula 1 to be translocated to the crop plant. The locus relevant to the method most commonly includes the growing medium in which the plant is cultivated (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.

[0385] 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) enhanced 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 crop's vegetative propagation; (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) enhanced ability of the crop to resist or prevent plant disease infection and infestation by arthropod, nematode, or mollusk pests; and (e) increased ability of the crop to tolerate environmental stresses, such as extreme temperatures, suboptimal moisture, or exposure to phytotoxic chemicals.

[0386] The compounds of the present disclosure 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. Without such control of herbivorous invertebrate pests, 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 disclosure can increase plant vigor by altering the plant's metabolism. Generally, the vigor of crop plants will be most significantly increased by treating the plants with compounds of the present disclosure if the plants are grown in a non-ideal environment, i.e., an environment that contains one or more aspects that are unfavorable for the plants to achieve the full genetic potential that they would exhibit in an ideal environment.

[0387] 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 growing in an environment that does not include herbivorous invertebrate pests. Also of note is a method for increasing the vigor of crop plants growing in an environment that includes an amount of moisture that is not ideal for supporting the growth of the crop plants. Of note is a method for increasing the vigor of crop plants, wherein the crop is rice. Also of note is a method for increasing the vigor of crop plants, wherein the crop is maize (corn). Also of note is a method for increasing the vigor of crop plants, wherein the crop is soybean.

[0388] The compounds of the present disclosure can also be mixed with one or more other bioactive compounds or agents, including insecticides, fungicides, nematicides, bactericides, miticides, herbicides, herbicide safeners, growth regulators, such as insect molting inhibitors and root stimulators, chemical hemostats, 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. Thus, the present disclosure 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 bioactive compound or agent. For mixtures of the present disclosure, the other bioactive compounds or agents can be formulated together with the present compounds, including compounds of Formula 1, to form a premix, or the other bioactive compounds or agents can be formulated separately from the present compounds, including compounds of Formula 1, and the two formulations can be combined together (e.g., in a spray tank) prior to application, or alternatively applied sequentially.

[0389] Examples of such biologically active compounds or agents that can be combined with the compounds of the present disclosure include insecticides such as 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-dihydroxybenzoates], benzophenone-3, benzophenone-4, benzophenone-5, benzophenone-6, benzophenone-7, benzophenone-8, benzophenone-9, benzophenone-10, 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, benzophenone-29, benzophenone-30, benzophenone-31, benzophenone-32, benzophenone-33, benzophenone-34, benzophenone-35, benzophenone-36, benzophenone-37, benzophenone-38, benzophenone-39, benzophenone-40, benzophenone-41, benzophenone-42, benzophenone-43, benzophenone-44, benzophenone-45, benzophenone-46, benzophenone-47, benzophenone-48, -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, carbali 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), Craniliprole (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-α]azepine) cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, geldrin, diflubenzuron, dimefluthrin, dimehypo, dimethoate, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenbutatin oxide, fenbutatin Fenitrothion, 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), flufensul fluhexafon (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)-furan-3-yl) Lanone), fluvalinate, tau-fluvalinate, fonofos, 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, meperfluthrin ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl (1R,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate), metaflumizone, metaldehyde, methamidophos, methidathion, methiodicarb, methomyl, methoprene, methoxychlor, metofluthrin, methoxyfenozide, metofluthrin, monocrotophos, monofluorothrin ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl (1R,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate), -(Methoxymethyl)phenyl]methyl 3-(2-cyano-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-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]methyl 2,2,3,3-tetramethylcyclopropanecarboxylate), tetraniliprole, thiacloprid, thiamethoxam, thiodicarb, thiosultap sodium, thioxazaphen (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.

[0390] 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.

[0391] In one embodiment of the biological agents for mixing with the compounds of the present disclosure, there are 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, e.g., green muscardine fungus; and entomopathogenic viruses (both naturally occurring and genetically modified), such as baculoviruses, nucleopolyhedroviruses (NPV), e.g., Helicoverpa zea nucleopolyhedrovirus (HzNPV), Anagrapha falcifera (Anagrapha falcifera), and entomopathogenic fungi (e.g., entomopathogenic fungi). falcifera nucleopolyhedrovirus (AfNPV); and granulosis viruses (GV), such as codling moth (Cydia pomonella) granulosis virus (CpGV).

[0392] In one embodiment, biological agents for mixing with the compounds of the present disclosure include: (i) Actinomycetes, Agrobacterium spp., Arthrobacter spp., Alcaligenes spp., Aureobacterium spp., Azobacter spp., Bacillus spp., Beijerinckia spp., Bradyrhizobium spp., and the like. ), Brevibacillus, Burkholderia, Chromobacterium, Clostridium, Clavibacter, Comamonas, Corynebacterium, Curtobacterium, Enterobacter , Flavobacterium genus, Gluconobacter genus, Hydrogenophaga genus, Klebsiella genus, Methylobacterium genus, Paenibacillus genus, Pasteuria genus, Photorhabdus genus, Phyllobacterium Bacteria of the genus Bacillus, Pseudomonas, Rhizobium, Serratia, Sphingobacterium, Stenotrophomonas, Streptomyces, Variovorax, or Xenorhabdus, such as Bacillus amyloliquefaciens, Bacillus cereus, Bacillus firmus, Bacillus licheniformis,(ii) bacteria, such as Bacillus licheniformis, Bacillus pumilus, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Bradyrhizobium japonicum, Chromobacterium subtsugae, Pasteuria nishizawae, Pasteuria penetrans, Pasteuria usage, Pseudomonas fluorescens, and Streptomyces lydicus; (ii) fungi, such as green muscardine fungus); (iii) baculovirus, nuclear polyhedrosis virus, such as Helicoverpa zea nuclear polyhedrosis virus, Anagrapha falcifera nuclear polyhedrosis virus; granulosis virus, such as Cydia pomonella granulosis virus, or a combination of these viruses.

[0393] Of particular note are 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 that has a similar control spectrum but a different site of action are particularly advantageous for resistance management. Thus, the compositions of the present disclosure may further comprise a biologically effective amount of at least one additional invertebrate pest control active ingredient that has a similar control spectrum but belongs to a different chemical class or has a different site of action. These additional biologically active compounds or agents include, but are not limited to, acetylcholinesterase (AChE) inhibitors, such as the carbamates methomyl, oxamyl, thiodicarb, triazamate, and the organophosphate compound chlorpyrifos; GABA-gated chloride channel antagonists, such as the cyclodiene geldrin and endosulfan, and the phenylpyrazoles ethiprole and fipronil; sodium channel modulators, such as the pyrethroids bifenthrin, 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, the sulfoximine sulfoxaflor, the butenolide flupyradifurone, and the mesoion triflumezopyrim; 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; chordotonal organ modulators, such as pymetrozine, pyrifluquinazone, and flonicamid; mite growth inhibitors, such as etoxazole; inhibitors of mitochondrial ATP synthase, such as propargite; uncouplers of oxidative phosphorylation via disruption of the proton gradient, such as chlorfenapyr;Nicotinic acetylcholine receptor (nAChR) channel blockers, such as the nereistoxin analogue cartap; inhibitors of chitin biosynthesis, such as the benzoylureas flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron and triflumuron, and buprofezin; dipteran molting inhibitors, such as cyromazine; ecdysone receptor agonists, such as the diacylhydrazines methoxyfenozide and tebufenozide; octopamine receptor agonists, such as amitraz; mitochondrial complex III electron transport inhibitors, such as hydramethylnon and bifenazate; mitochondrial complex I electron transport inhibitors, such as pyridaben; voltage-dependent sodium channel blockers, such as indomethacin; These include xacarb; inhibitors of acetyl-CoA carboxylase, such as the tetronic and tetramic acid derivatives spirodiclofen, spiromesifen, and spirotetramat; mitochondrial complex II electron transport inhibitors, such as the β-ketonitriles cyenopyrafen and cyflumetofen; ryanodine receptor modulators, such as the anthranildiamides chlorantraniliprole and cyantraniliprole, diamides such as flubendiamide, and ryanodine receptor ligands, such as ryanodine; compounds with unknown or uncharacterized target sites for biological activity, such as azadirachtin and pyridalyl; microbial disruptors of the insect midgut membrane, such as Bacillus thuringiensis and the delta-endotoxin it produces, and Bacillus sphaericus; and biological agents, including nuclear polyhedrosis virus (NPV) and other naturally occurring or genetically modified insecticidal viruses.

[0394] Further examples of biologically active compounds or agents that can be combined with the compounds of the present disclosure include: fungicides such as acibenzolar-S-methyl, aldimorph, ametoctrazine, aminopyrifen, amisulbrom, anilazine, azaconazole, azoxystrobin, benalaxyl (including benalaxyl-M), benodanil, benomyl, benthiavalicarb (including benthiavalicarb-isopropyl), benzovindiflupyr, bethoxadin, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, boscalid, Bromuconazole, bupirimate, buthiobate, carboxin, carpropamid, captafol, captan, carbendazim, chloroneb, chlorothalonil, chlozolinate, copper hydroxide, copper oxychloride, copper sulfate, cumoxystrobin, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, diclobenthiazox, dichlofluanid, diclocymet, diclomedine, dicloran, diethofencarb, difenoconazole, diflumetrim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole ( Diniconazole-M), dinocap, dipimethitron, dithianon, dithiolane, dodemorph, dodine, econazole, etaconazole, edifenphos, enoxastrobin (also known as enestrobulin), epoxiconazole, ethaboxam, ethirimol, etridiazole, famoxadone, fenamidone, phenaminestrobin, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fenpicoxamid, fenpropidin, fenpropimorph, fenpi Razamin, triphenyltin acetate, triphenyltin hydroxide, Ferbam, ferimzone, flometoquin, florylpicoxamide, fluopimomide, fluazinam, fludioxonil, flufenoxystrobin, fluindapyr, flumorph, fluopicolide, fluopyram, fluoxapiprolin, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, fthalide (also known as phthalide), fuberidazole, furalaxyl,Furamethopyr, hexaconazole, hymexazole, guazatine, imazalil, imibenconazole, iminoctadine albesilate, iminoctadine triacetate, impilfluxam, iodicarb, ipconazole, ipfentrifluconazole, ipflufenoquin, isofetamide, iprobenfos, iprodione, iprovalicarb, isoflucipram, isoprothiolane, isopyrazam, isotianil, kasugamycin, kresoxim-methyl, lancotrione, mancozeb, mandipropamide, mandestrobin, ma Nneb, mapanipyrin, mefentrifluconazole, mepronil, meptyldinocap, metalaxyl (including metalaxyl-M / mefenoxam), metconazole, metasulfocarb, metiram, metominostrobin, methyltetraprole, metrafenone, myclobutanil, naftitine, neo-asozin (ferric methanearsonate), nuarimol, octhilinone, ofurace, orysastrobin, oxadixyl, oxathiapiprolin, oxolinic acid, oxpoconazole, oxycarbo oxalin, oxytetracycline, penconazole, pencycuron, penflufen, penthiopyrad, perfurazoate, phosphorous acid (including its salts, such as fosetyl-aluminm), picoxystrobin, piperalin, polyoxins, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, proquinazide, prothiocarb, prothioconazole, pydiflumetofen (Adepidine®), pyraclostrobin, pyrametostrobin, pyrapropoin, pyroxystrobin , pyraziflumide, pyrazophos, pyribencarb, pyributacarb, pyridaclomethyl, pyrifenox, pyriophenone, perisoxazole, pyrimethanil, pyrifenox, pyrrolnitrin, pyroquilon, quinconazole, quinmethionate, quinofumelin, quinoxyfen, quintozene, silthiofam, sedaxane, simeconazole, spiroxamine, streptomycin, sulfur, tebuconazole, tebufloquine, tecloftalam, tecloftalam,Tecnazene, terbinafine, tetraconazole, thiabendazole, thifluzamide, thiophanate, thiophanate-methyl, thyram, tiadinil, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triarimol, triazoxide, tribasic copper sulfate, triclopiricarb, tridemorph, trifloxystrobin, triflumizole, trimopreamide tricyclazole, trifloxystrobin, triforine, triticonazole, uniconazole, validamycin, valifenalate (also known as valifenal), vinclozolin, zineb, ziram, zoxamide, and 1-[4-[4-[5-(2, 6-Difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone; nematicides, such as fluopyram, spirotetramat, thiodicarb, fosthiazate, abamectin, iprodione, fluensulfone, dimethyl disulfide, thioxazafen, 1,3-dichloropropene (1,3-D), metam (sodium and potassium), dazomet, chloropicrin, fenamiphos, ethoprophos, cadusafos, terbufos, imicyafos, oxamyl, carbofuran, thioxazafen, Bacillus firmus (Bacillus firmus, and Pasteuria nishizawae; fungicides such as streptomycin; acaricides such as amitraz, quinomethionate, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben, and tebufenpyrad.

[0395] Invertebrate pests are controlled in agricultural and non-agricultural applications by applying one or more compounds of the present disclosure, typically in the form of a composition, in a biologically effective amount to the environment of the pest, including agricultural and / or non-agricultural infested loci, to the area to be protected, or directly onto the pest to be controlled.

[0396] Thus, the present disclosure includes methods for controlling and eradicating invertebrate pests in agricultural and / or non-agricultural applications, comprising contacting the invertebrate pests or their environment with a biologically effective amount of one or more of the compounds of the present disclosure, or a composition comprising at least one such compound, or a composition comprising at least one such compound and a biologically effective amount of at least one additional biologically active compound or agent. Examples of suitable compositions comprising a compound of the present disclosure and a biologically effective amount of at least one additional biologically active compound or agent include granular compositions in which the additional active compound is present on the same granules as the compound of the present disclosure or on separate granules from the compound of the present disclosure.

[0397] To achieve contact with the compounds or compositions of the present disclosure for the protection of agricultural crops from invertebrate pests, the compounds or compositions are typically applied to the seeds of the crop prior to planting, to the foliage (e.g., leaves, stems, flowers, fruits) of the crop plants, or to the soil or other growing medium before or after planting the crop.

[0398] One embodiment of the contact method is by spraying. Alternatively, a granular composition containing a compound of the present disclosure can be applied to the foliage or soil of a plant. The compound of the present disclosure can also be effectively delivered via plant ingestion by contacting a plant with a composition containing a compound of the present disclosure applied as a soil dip in a liquid formulation, a granular formulation to the soil, a nursery box treatment, or a transplant dipping. Of note is a composition of the present disclosure in the form of a liquid soil dip formulation. Also of note is a method for controlling and eradicating invertebrate pests, comprising contacting the invertebrate pests or their environment with a biologically effective amount of a compound of the present disclosure or a composition containing a biologically effective amount of a compound of the present invention. Of further note is this method in which the environment is soil and the composition is applied to the soil as a soil dip formulation. It is further noted that the compound of the present disclosure is also effective when applied locally to the infested locus. Other contact methods include application of the compounds or compositions of the present disclosure by direct and residual spraying, aerial spraying, gels, seed coating, microencapsulation, systemic ingestion, bait, ear tag, bolus, sprayer, fumigator, aerosol, dust, and many others. One embodiment of the contact method is a dimensionally stable fertilizer granule, stick, or tablet containing the compounds or compositions of the present disclosure. The compounds of the present disclosure can also be impregnated into the materials used to construct invertebrate control devices (e.g., insect nets).

[0399] The compounds of the present disclosure are useful for treating all plants, plant parts, and seeds. Plant and seed varieties and cultivars can be obtained by conventional breeding and propagation methods or genetic engineering methods. Genetically modified plants or seeds (transgenic plants or seeds) are those in which a heterologous gene (transgene) is stably integrated into the genome of the plant or seed. A transgene defined by its specific location in the plant genome is called a transformation or transgenic event.

[0400] Genetically modified plant and seed cultivars that can be treated according to the present disclosure include those that are resistant to one or more biotic stresses (pests such as nematodes, insects, mites, fungi, etc.) or abiotic stresses (drought, low temperature, soil salinity, etc.), or contain other desirable characteristics. Plants and seeds can be genetically modified to exhibit traits such as herbicide tolerance, insect resistance, altered oil profile, or drought tolerance. Useful genetically modified plants and seeds containing single gene transformation events or combinations of transformation events are listed in Table Z. Additional information about the genetic modifications listed in Table Z can be obtained from the following databases: OECD BioTrack Product Database [Database online]. Retrieved from the Organisation for Economic Co-operation and Development (OECD) via the internet.<https: / / biotrackproductdatabase.oecd.org / byidentifier.aspx> USDA Animal and Plant Health Inspection Service [Database Online]. Retrieved from the US Department of Agriculture via the Internet.<http: / / www.aphis.usda.gov> Deliberate Release and Placing on the EU Market of GMOs - GMO Register [database online]. Retrieved via internet from the European Commission Joint Research Centre<http: / / gmoinfo.jrc.ec.europa.eu>

[0401] In Table Z below, the following abbreviations are used: tol. is tolerant, res. is resistant, SU is sulfonylurea, ALS is acetolactate synthase, HPPD is 4-hydroxyphenylpyruvate dioxygenase, and NA is not applicable.

[0402] Table 7

[0403] Table 8

[0404] Table 9

[0405] Table 10

[0406] Table 11

[0407] Table 12

[0408] Table 13

[0409] Table 14

[0410] Table 15

[0411] Table 16

[0412] [Table 17]

[0413] Treating genetically modified plants and seeds with compounds of the present disclosure can provide enhanced effects, such as reduced application rates, broadened spectrum of activity, increased resistance to biotic / abiotic stresses, or enhanced storage stability, that are greater than would be expected from a simple additive effect of applying compounds of the present disclosure to genetically modified plants and seeds.

[0414] The compounds of the present disclosure are also useful in seed treatments to protect seeds from invertebrate pests. For purposes of this disclosure and claims, treating seeds means contacting the seeds with a biologically effective amount of a compound of the present disclosure, typically formulated as a composition of the present disclosure. This seed treatment protects the seeds from invertebrate soil pests and generally also protects the roots and other plant parts that come into contact with the soil of seedlings that emerge from the germinated seeds. The seed treatment can also provide foliage protection by translocating the compound of the present disclosure or a second active ingredient within the developing plant. Seed treatments can be applied to all types of seeds, including those that will germinate plants genetically transformed to express specific traits. Representative examples include those that express proteins toxic to invertebrate pests, such as Bacillus thuringiensis toxins, or those that express herbicide resistance, such as glyphosate acetyltransferase, which confers resistance to glyphosate. Seed treatment with the compounds of the present disclosure can also increase the vigor of plants grown from the treated seeds.

[0415] One method of seed treatment involves spraying or dusting the seeds with a compound of the present disclosure (i.e., as a formulated composition) before sowing. Seed treatment compositions generally contain a film former or adhesive. Thus, a seed coating composition of the present disclosure typically contains a biologically effective amount of a compound of Formula 1, its N-oxide or salt, and a film former or adhesive. Seeds can be coated by spraying a flowable suspension concentrate directly onto a tumbling bed of seeds and then allowing the seeds to dry. Other formulation types, such as wettable powders, solutions, suspoemulsions, emulsifiable concentrates, and emulsions in water, can also be sprayed onto the seeds. This process is particularly useful for applying film coatings to seeds. Various coating machines and processes are available to those skilled in the art. Suitable processes include those described in P. Kosters et al., Seed Treatment: Progress and Prospects, 1994 BCPC Monograph No. 57 and the references cited therein.

[0416] The compounds of Formula 1 and compositions thereof, alone and in combination with other insecticides and fungicides, are particularly useful as seed treatments for crops including, but not limited to, corn or maize, soybeans, cotton, cereals (e.g., wheat, oats, barley, rye, and rice), potatoes, vegetables, and rapeseed.

[0417] Other insecticides that may be combined with the compounds of Formula 1 to provide mixtures useful for seed treatment include abamectin, acetamiprid, acrinathrin, amitraz, avermectin, azadirachtin, bensultap, bifenthrin, buprofezin, carbaryl, carbofuran, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenothiocarb, fenoxycarb, , fenvalerate, fipronil, flonicamid, flubendiamide, flufenoxuron, fluvalinate, formetanate, fosthiazate, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, lufenuron, metaflumizone, methiocarb, methomyl, methoprene, methoxyfenozide, nitenpyram, nithiazine, novaluron, oxamyl, pymetrozine, pyrethrins, pyridaben, pyridalyl, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulfoxaflor, tebufenozide, tetramethrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, triflumuron, Bacillus thuringiensis (Bacillus thuringiensis delta-endotoxin, all strains of Bacillus thuringiensis, and all strains of nuclear polyhedrosis virus.

[0418] Fungicides that may be combined with the compounds of Formula 1 to provide mixtures useful for seed treatment include amisulbrom, azoxystrobin, boscalid, carbendazim, carboxin, cymoxanil, cyproconazole, difenoconazole, dimethomorph, fluazinam, fludioxonil, fluquinconazole, fluopicolide, fluoxastrobin, flutriafol, fluxapyroxad, ipconazole, iprodione, metalaxyl, mefenoxam, metconazole, myclobutanil, paclobutrazol, penflufen, picoxystrobin, prothioconazole, pyraclostrobin, sedaxane, silthiofam, tebuconazole, thiabendazole, thiophanate-methyl, thiram, trifloxystrobin, and triticonazole.

[0419] Compositions containing a compound of Formula 1 useful for seed treatment may further include bacteria such as Bacillus pumilus (e.g., strain GB34) and Bacillus firmus (e.g., isolate 1582), rhizobia inoculants / extenders, isoflavonoids, and lipo-chitooligosaccharides.

[0420] Treated seeds typically contain a compound of the present disclosure in an amount of about 0.1 g to 1 kg per 100 kg of seed (i.e., about 0.0001 to 1% by weight of the seed before treatment). Flowable suspensions formulated for seed treatment typically contain about 0.5 to about 70% active ingredient, about 0.5 to about 30% film-forming adhesive, about 0.5 to about 20% dispersant, 0 to about 5% thickener, 0 to about 5% pigment and / or dye, 0 to about 2% antifoaming agent, 0 to about 1% preservative, and 0 to about 75% volatile liquid diluent.

[0421] The compounds of the present disclosure can be incorporated into bait compositions that are consumed by invertebrate pests or used in devices such as traps and bait stations. Such bait compositions can be in the form of granules containing (a) a biologically effective amount of the compound of Formula 1, its N-oxide, or salt; (b) one or more food materials; optionally (c) an attractant; and optionally (d) one or more humectants. Of note are granules or bait compositions containing about 0.001-5% of the active ingredient, about 40-99% of the food material and / or attractant; and optionally about 0.05-10% of the humectant, which are effective in controlling and eliminating soil invertebrate pests at very low application rates, particularly at doses of the active ingredient that are lethal via ingestion rather than direct contact. Some food materials can function as both a food source and an attractant. Food materials include carbohydrates, proteins, and lipids. Examples of food ingredients include vegetable flour, sugar, starch, animal fat, vegetable oil, yeast extract, and milk solids. Examples of attractants include flavorings and flavoring agents such as fruit or plant extracts, fragrances, or other animal or plant ingredients, pheromones, or other agents known to attract target invertebrate pests. Examples of humectants, i.e., moisture-retaining agents, include glycols and other polyols, glycerin, and sorbitol. Of note are bait compositions (and methods utilizing such bait compositions) used to control at least one invertebrate pest selected from the group consisting of ants, termites, and cockroaches. A device for controlling and eliminating invertebrate pests can include the bait composition 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 outside the housing, and wherein the housing is further configured to be placed at or near a location of potential or known invertebrate pest activity.

[0422] While the compounds of the present disclosure can be applied without other adjuvants, in most cases, application involves the application of a formulation containing one or more active ingredients along with suitable carriers, diluents, and surfactants, and optionally in combination with food products depending on the intended end use. One application method involves spraying an aqueous dispersion or refined oil solution of the compounds of the present disclosure. Combinations with spray oils, spray oil concentrates, spreader stickers, adjuvants, other solvents, and piperonyl butoxide often enhance compound efficacy. For non-agricultural uses, such sprays can be applied from a spray container, such as a can, bottle, or other container, by pump or by release from a pressurized container, e.g., a pressurized aerosol spray can. Such spray compositions can take various forms, such as sprays, mists, foams, fogs, or mist. Thus, such spray compositions can optionally further include propellants, foaming agents, etc. Of note are spray compositions comprising a biologically effective amount of a compound or composition of the present disclosure and a carrier. One embodiment of such a spray composition comprises a biologically effective amount of a compound or composition of the present disclosure and a propellant. Representative propellants include, but are not limited to, methane, ethane, propane, butane, isobutane, butene, pentane, isopentane, neopentane, pentene, hydrofluorocarbons, chlorofluorocarbons, dimethyl ether, and mixtures thereof. Of note are spray compositions (and methods utilizing such spray compositions dispensed from a misting container) used individually or in combination to control at least one invertebrate pest selected from the group consisting of mosquitoes, black flies, stable flies, deer flies, horseflies, wasps, yellow jackets, hornets, ticks, spiders, ants, black flies, and the like.

[0423] One embodiment of the present disclosure relates to a method for controlling and combating invertebrate pests, comprising diluting a pesticidal composition of the present disclosure (a compound of Formula 1 formulated with a surfactant, a solid diluent, and a liquid diluent, or a combined mixture of a compound of Formula 1 and at least one other pesticide) with water, and optionally adding an adjuvant to form a diluted composition, and contacting the invertebrate pest or its environment with an effective amount of the diluted composition.

[0424] Although spray compositions formed by diluting a sufficient concentration of the pesticidal composition with water can be fully effective in controlling and eliminating invertebrate pests, separately formulated adjuvant products can also be added to the spray tank mix. These additional adjuvants, commonly known as "spray adjuvants" or "tank-mix adjuvants," include any substance mixed in the spray tank that improves pesticide performance or alters the physical properties of the spray mixture. Adjuvants can be surfactants, emulsifiers, petroleum-based crop oils, crop-derived seed oils, acidifiers, buffers, thickeners, or antifoaming agents. Adjuvants are used to enhance efficacy (e.g., bioavailability, adhesion, penetration, uniformity of coverage, and durability of protection) or minimize or eliminate spray application problems associated with incompatibility, foaming, drift, evaporation, volatilization, and degradation. To achieve optimal performance, adjuvants are selected based on the characteristics of the active ingredient, formulation, and target (e.g., crop, insect pest).

[0425] Among spray adjuvants, oils including crop oils, crop oil concentrates, vegetable oil concentrates and methylated seed oil concentrates are most commonly used to improve the effectiveness of pesticides by promoting more uniform and homogeneous spray deposition in some cases.In situations where the plant toxicity potentially caused by oil or other water-immiscible liquids is a concern, the spray composition prepared from the composition of the present disclosure generally does not contain oil-based spray adjuvants.However, in situations where the plant toxicity caused by oil-based spray adjuvants is not commercially important, the spray composition prepared from the composition can also contain oil-based spray adjuvants, which can potentially further increase the control of invertebrate pests and rain resistance.

[0426] Products identified as "crop oil" typically contain 95-98% paraffin- or naphtha-based petroleum and 1-2% of one or more surfactants that function as emulsifiers. Products identified as "crop oil concentrates" typically consist of 80-85% emulsifiable petroleum-based oil and 15-20% nonionic surfactants. Products specifically identified as "vegetable oil concentrates" typically consist of 80-85% vegetable oil (i.e., seed or fruit oils, most commonly derived from cotton, linseed, soybean, or sunflower) and 15-20% nonionic surfactants. Adjuvant performance can be improved by replacing the vegetable oil with methyl esters of fatty acids, typically derived from the vegetable oil. Examples of methylated seed oil concentrates include MSO® Concentrate (UAP-Loveland Products, Inc.) and Premium MSO Methylated Spray Oil (Helena Chemical Company).

[0427] The amount of adjuvant added to the spray mixture generally does not exceed about 2.5% by volume, and more typically the amount is about 0.1 to about 1% by volume. The application rate of adjuvant added to the spray mixture is typically about 1 to 5 L per hectare. Representative examples of spray adjuvants include: Adigor® (Syngenta) 47% methylated rapeseed oil in liquid hydrocarbon, Silwet® (Helena Chemical Company) polyalkylene oxide-modified heptamethyltrisiloxane, and Assist® (BASF) 17% surfactant blend in 83% paraffin-based mineral oil.

[0428] Non-agricultural uses include protecting animals, particularly vertebrates, more particularly warm-blooded vertebrates (e.g., mammals or birds), most particularly mammals, from invertebrate parasitic pests by administering to the animal to be protected a parasiticidally effective (i.e., biologically effective) amount of a compound of the present disclosure, typically in the form of a composition formulated for animal use. Of note, therefore, is a method for protecting animals, comprising administering to the animal a parasiticidally effective amount of a compound of the present disclosure. The terms "parasiticidally" and "parasitically" referred to in this disclosure and claims refer to an observable effect on invertebrate parasitic pests to achieve protection of the animal from the pest. A parasiticidal effect typically relates to reducing the occurrence or activity of the target invertebrate parasitic pest. Such effects on pests include necrosis, death, retarded development, reduced motility or ability to persist on or within the host animal, reduced feeding, and inhibited reproduction. These effects on invertebrate parasitic pests provide for the control (including prevention, reduction, or elimination) of parasitic infestation or infection in animals. Examples of invertebrate parasitic pests that may be controlled by administering a parasiticidally effective amount of a compound of the present disclosure to an animal to be protected include ectoparasites (arthropods, acarines, etc.) and endoparasites (parasitic helminths, e.g., nematodes, trematodes, cestodes, thorny head worms, etc.). In particular, the compounds of the present disclosure are effective against ectoparasites, including flies such as Haematobia (Lyperosia) irritans (horn fly), Stomoxys calcitrans (stable fly), Simulium spp. (gnats), Glossina spp. (tsetse flies), Hydrotaea irritans (head fly), Musca autumnalis (face fly), Musca domestica (house fly), Morelia simplex,simplex (sweat fly), Tabanus spp. (bottle flies), Hypoderma bovis, Hypoderma lineatum, Lucilia sericata, Lucilia cuprina (sheep blowfly), Calliphora spp. (blowflies), Protophormia spp., Oestrus ovis (sheep fly), Culicoides spp. (midgets), Hippobosca equine, Gastrophilus instestinalis, Gastrophilus haemoroidalis haemorrhoidalis, and Gastrophilus naslis; lice, for example, Bovicola (Damalinia) bovis, Bovicola equi, Haematopinus asini, Felicola subrostratus, Heterodoxus spiniger, Lignonathus setosus, and Trichodectes canis; sheep lice, for example, Melophagus ovinus; mites, for example, Psoroptes spp., Sarcoptes scabiei scabei, Chorioptes bovis, Demodex equi, Cheyletiella spp., Notoedres cati, Trombicula spp., and Otodectes cyanotiscyanotis (ear mites); ticks, such as Ixodes spp., Boophilus spp., Rhipicephalus spp., Amblyomma spp., Dermacentor spp., Hyalomma spp., and Haemaphysalis spp.; and fleas, such as Ctenocephalides felis (cat flea) and Ctenocephalides canis (dog flea).

[0429] Non-agricultural applications in the veterinary field are by conventional means, for example, by enteral administration in the form of tablets, capsules, drinks, dip preparations, granules, pastes, boluses, feed-through procedures, or suppositories; parenteral administration, for example, by injection (including intramuscular, subcutaneous, intravenous, intraperitoneal) or implants; by nasal administration; and by topical administration, for example, in the form of a dip or immersion, spray, wash, coating with powder, or application to a small area of ​​an animal, and via an article comprising a compound or composition of the present disclosure, for example, a collar, ear tag, tail band, leg band, or halter.

[0430] Typically, parasiticidal compositions according to the present disclosure comprise a mixture of a compound of Formula 1, its N-oxide, or salt, and one or more pharmaceutically or veterinarily acceptable carriers, including excipients and adjuvants, selected with respect to the intended route of administration (e.g., oral, topical, or parenteral administration, e.g., injection), and in accordance with standard practice. In addition, suitable carriers are selected based on compatibility with one or more active ingredients in the composition, including considerations such as stability relative to pH and water content. Accordingly, of note are compositions for protecting animals from invertebrate parasitic pests, comprising a parasitically effective amount of a compound of the present disclosure and at least one carrier.

[0431] For parenteral administration, including intravenous, intramuscular, and subcutaneous injection, the compounds of the present disclosure can be formulated in suspension, solution, or emulsion in oily or aqueous vehicles, and may contain auxiliary agents, such as suspending, stabilizing, and / or dispersing agents. Pharmaceutical compositions for injection preferably comprise aqueous solutions of a water-soluble form of the active ingredient (e.g., a salt of the active compound) in a physiologically compatible buffer containing other excipients or auxiliary agents as known in the art of pharmaceutical formulation.

[0432] For oral administration in the form of solutions (the most readily available form for absorption), emulsions, suspensions, pastes, gels, capsules, tablets, boluses, powders, granules, rumen-retention, and feed / water / lick blocks, the compounds of the present disclosure can be formulated with binders / fillers known in the art to be suitable for oral administration compositions, such as sugars (e.g., lactose, sucrose, mannitol, sorbitol), starches (e.g., corn starch, wheat starch, rice starch, potato starch), cellulose and derivatives (e.g., methylcellulose, carboxymethylcellulose, ethylhydroxycellulose), protein derivatives (e.g., zein, gelatin), and synthetic polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone). Lubricants (e.g., magnesium stearate), disintegrants (e.g., cross-linked polyvinylpyrrolidinone, agar, alginic acid), and dyes or pigments can be added as needed. Pastes and gels also often contain adhesives (e.g., acacia, alginate, bentonite, cellulose, xanthan gum, colloidal magnesium aluminum silicate) that help the composition remain in contact with the oral cavity and prevent it from being easily expelled.

[0433] If the parasiticidal composition is in the form of a feed concentrate, the carrier is typically selected from high-performance feed, feed grain, or protein concentrate. In addition to the parasiticidal active ingredient, such feed concentrate-containing compositions may contain additives that promote animal health or growth, improve the quality of meat from slaughtered animals, or are otherwise useful to animal husbandry. These additives may include, for example, vitamins, antibiotics, chemotherapeutic agents, bacteriostatic agents, fungistatic agents, anticoccidial agents, and hormones.

[0434] The compounds of the present disclosure have been found to have favorable pharmacokinetic and pharmacodynamic properties that allow for systemic availability through oral administration and oral ingestion.Therefore, after ingestion by the animal to be protected, a parasiticidally effective concentration of the compounds of the present disclosure in the bloodstream protects the treated animal from blood-sucking pests, such as fleas, ticks, and lice.Therefore, of note is a composition for protecting animals from invertebrate parasitic pests, in a form for oral administration (i.e., comprising a parasiticidally effective amount of the compounds of the present disclosure, as well as one or more carriers selected from binders and fillers suitable for oral administration, and feed concentrate carriers).

[0435] Formulations for topical administration are typically in the form of powders, creams, suspensions, sprays, emulsions, foams, pastes, aerosols, ointments, salves, or gels. More typically, topical preparations are aqueous solutions, which may be in the form of concentrates that are diluted before use. Parasiticidal compositions suitable for topical administration typically contain a compound of the present disclosure and one or more topically suitable carriers. In applying a topical parasiticidal composition to the exterior of an animal as a line or spot (i.e., "spot-on" treatment), the active ingredient migrates across the surface of the animal, covering most or all of its exterior surface area. As a result, the treated animal is particularly protected from invertebrate pests that infest the animal's epidermis, such as ticks, fleas, and lice. Therefore, formulations for topical administration often contain at least one organic solvent to facilitate transport of the active ingredient across the skin and / or penetration into the animal's epidermis. Solvents commonly used as carriers in such formulations include propylene glycol, paraffins, aromatic compounds, esters such as isopropyl myristate, glycol ethers, and alcohols such as ethanol and n-propanol.

[0436] The application rate required for effective control (i.e., "biologically effective amount") will depend on factors such as the species of invertebrate to be controlled, the pest's life cycle, life stage, its size, location, timing, host crop or animal, feeding behavior, reproductive behavior, ambient humidity, and temperature. Under normal circumstances, an application rate of about 0.01 to 2 kg of active ingredient per hectare is sufficient to control pests in agricultural ecosystems, although as little as 0.0001 kg / hectare may be sufficient, or as much as 8 kg / hectare may be required. For non-agricultural applications, effective application rates range from about 1.0 to 50 mg / m², although as little as 0.1 mg / m² may be sufficient, or as much as 150 mg / m² may be required. Those skilled in the art can readily determine the biologically effective amount necessary for the desired level of invertebrate pest control.

[0437] Generally, for veterinary use, the compound of Formula 1, its N-oxide, or salt is administered in a parasiticidally effective amount to an animal to be protected from an invertebrate parasitic pest. A parasiticidally effective amount is the amount of active ingredient required to achieve an observable effect, reducing the occurrence or activity of the target invertebrate parasitic pest. Those skilled in the art will understand that the parasitically effective dose may vary for various compounds and compositions of the present disclosure, the desired parasitic effect and duration, the target invertebrate pest species, the animal to be protected, and the method of application, and the amount required to achieve a particular result may be determined by simple experimentation.

[0438] For oral administration to warm-blooded animals, the daily dosage of the compounds of the present disclosure typically ranges from about 0.01 mg / kg to about 100 mg / kg, more typically from about 0.5 mg / kg to about 100 mg / kg of animal body weight. For topical (e.g., dermal) administration, dips and sprays typically contain from about 0.5 ppm to about 5000 ppm, more typically from about 1 ppm to about 3000 ppm, of the compounds of the present disclosure.

[0439] Recent advances in computational processing power have afforded scientists unprecedented opportunities to employ in silico tools to predict and investigate the potential adverse outcomes associated with xenobiotic exposure, as well as the molecular basis for these events. While current computational models cannot simply be used to replace all in vivo or in vitro experimental approaches, they nevertheless provide valuable tools for generating hypotheses, flagging compounds of interest, and aiding in prioritizing and aligning chemicals for appropriate in vitro or in vivo studies.

[0440] Computational / predictive toxicology is a rapidly evolving field that integrates information and data from a variety of sources to develop mathematical and computer-based models to better understand and predict interactions between chemical agents and biological organisms across many scales (e.g., population, individual, cellular, and molecular) and can be thought of as encompassing two broad areas: (1) Development and application of two-dimensional (2D) models via first principles (e.g., structural motifs that drive facile chemical reactivity) (Wijeyesakere, SJ et al. Development of a Profiler for Facile Chemical Reactivity Using the Open-Source Konstanz Information Miner. Appl. Vitr. Toxicol., 4, 202-213, 2018). Additionally, quantitative structure-activity relationship (QSAR) techniques such as trend analysis can be undertaken to predict dosimetry for the biological outcome of interest if experimental data from similar molecules are available (e.g., predicting the cholinergic potential of a series of related organophosphorus compounds) (Makhaeva, GF et al. Esterase profiles of organophosphorus compounds in vitro predict their behavior in vivo. Chem. Biol. Interact., 259, 332-342, 2016. Makhaeva, GF et al. Kinetics and mechanism of inhibition of serine esterases by fluorinated carbethoxy 1-aminophosphonates. Dokl. Biochem. Biophys., 451, 203-206, 2013). (2) "Big data" approaches that manage all available information on a specific outcome / mechanism of action (e.g., the use of predictive models to identify mitochondrial inhibitors (Wijeyesakere, SJ et al. Hybrid Machine-Learning / SMARTS Profiling Model for Mitochondrial Inhibition. Appl. Vitr. Toxicol., 5, 196-204, 2019) or those that can interact with defined neuronal receptors (Wijeyesakere, SJ et al. Prediction of cholinergic compounds by machine-learning. Comput. Toxicol., 13, 100119, 2020); and the evolution of these 2D assessments to encompass 3D techniques such as docking and molecular dynamics (MD) simulations to further explore the molecular basis for interactions between toxicants and known / putative biological targets (Wang, Y. et al. Mixed inhibition of adenosine deaminase activity by 1,3-dinitrobenzene: A Model for understanding cell-selective neurotoxicity) in chemically-induced energy deprivation syndromes in brain.Toxicol.Sci.,125,509-521,2012;Gonzalez,TLet al.Metabolites of n-Butylparaben and iso-Butylparaben Exhibit Estrogenic Properties in MCF-7 and T47D Human Breast Cancer Cell Lines. Toxicol. Sci., 164, 50-59018, 2018).

[0441] Specific compounds of Formula 1 prepared by the methods and variations described above in Schemes 1-8 and Synthetic Examples 1-3 are shown in Index Table A below. For mass spectral data (MS), the reported value is the molecular weight (M+1) of the highest isotopically abundant parent ion formed by adding H+ (molecular weight of 1) to the molecule as observed by mass spectrometry using atmospheric pressure chemical ionization (AP+). Melting point data (MP) are reported as a temperature range. Alternate molecular ion peaks (e.g., M+2 or M+4) that occur in compounds containing multiple halogens are not reported.

[0442] The following abbreviations are used in the index table below: Cmpd stands for compound, t is tertiary, c is cyclo, Me is methyl, Et is ethyl, Pr is propyl, i-Pr is isopropyl, Bu is butyl, c-Pr is cyclopropyl, c-Pn is cyclopentyl, c-Hx is cyclohexyl, t-Bu is tertiary butyl, Ph is phenyl, OMe is methoxy, SMe is methylthio, and SO2Me stands for methylsulfonyl. A wavy line in a structural fragment indicates the point of attachment of the fragment to the rest of the molecule. The abbreviation "Ex." stands for "Example," followed by a number indicating the synthetic example in which the compound was prepared.

[0443] [Table 18]

[0444] [Table 19]

[0445] [Table 20]

[0446] [Table 21]

[0447] The following tests demonstrate the control efficacy of the compounds of the present disclosure against specific pests. "Control efficacy" refers to the inhibition of invertebrate pest development (including mortality) resulting in significantly reduced feeding. However, the pest control protection provided by the compounds is not limited to these species. See Index Table A for compound descriptions. [Example]

[0448] Biological Examples Mixture and spraying method for tests A to G Test compounds were formulated using a solution containing 10% acetone, 90% water, and 300 ppm Activator 90® nonionic surfactant (Loveland Products, Loveland, Colorado, USA). The formulated compounds were applied in 1 mL of liquid through an atomizing nozzle positioned 1.27 cm (0.5 inches) above the top of each test unit. Test compounds were sprayed at the indicated amount, and each test was performed in triplicate.

[0449] Test A Test units for evaluating control of the corn planthopper (Peregrinus maidis (Ashmead)) by contact and / or systemic means consisted of small open containers containing 3- to 4-day-old corn (maize) plants. White sand was added to the soil prior to application of the test compound.

[0450] Test compounds were formulated and sprayed at 250 ppm and / or 50 ppm and / or 10 ppm. After spraying with the formulated test compounds, the test units were allowed to dry for one hour before being post-infested with approximately 15-20 nymphs (18-21 days old). A black obscuring cap was placed on top of each test unit, and the test units were maintained in a growth chamber at 22-24°C and 50-70% relative humidity for six days. Each test unit was then visually assessed for insect mortality.

[0451] Of the compounds of Formula 1 tested at 250 ppm, the following produced at least 80% mortality: 5, 6, 7.

[0452] Of the compounds of Formula 1 tested at 50 ppm, the following caused at least 80% mortality: 1, 5, 6, 7, 8, 10, 11, 12, 13, 14, 15, 16, 18, 21.

[0453] Of the compounds of Formula 1 tested at 10 ppm, the following produced at least 80% mortality: 12, 13, 14, 16, 21.

[0454] Test B Test units for evaluating control of the green peach aphid (Myzus persicae) (Sulzer) by contact and / or systemic means consisted of small, open containers containing 12- to 15-day-old radish plants. These were pre-infested by placing 30-40 aphids on a leaf strip excised from the culture plant onto the test plant leaf (cut leaf method). As the leaf strip dried, the aphids migrated onto the test plant. After pre-infestation, the soil in the test units was covered with a layer of sand.

[0455] Test compounds were formulated and sprayed at 250 and / or 50 ppm. After spraying with the formulated test compounds, each test unit was allowed to dry for one hour before a black obscuring cap was placed on top. The test units were held in a growth chamber at 19-21°C and 50-70% relative humidity for six days. Each test unit was then visually assessed for insect mortality.

[0456] Of the compounds of Formula 1 tested at 250 ppm, the following produced at least 80% mortality: 2, 4, 6.

[0457] Of the compounds of Formula 1 tested at 50 ppm, the following produced at least 80% mortality: 1, 4, 16.

[0458] Test C Test units for evaluating control of cotton aphid (Aphis gossypii (Glover)) by contact and / or systemic means consisted of small open containers containing 5-day-old okra plants pre-infested with 30-40 insects on a single leaf according to the cut-leaf method, and the soil in the test units was covered with a layer of sand.

[0459] Test compounds were formulated and sprayed at 250 and / or 50 ppm. After spraying, the test units were maintained in a growth chamber at 19°C and 70% relative humidity for 6 days. Each test unit was then visually assessed for insect mortality.

[0460] Of the compounds of Formula 1 tested at 250 ppm, the following produced at least 80% mortality: 2, 3, 4, 5, 6, 7.

[0461] Of the compounds of Formula 1 tested at 50 ppm, the following produced at least 80% mortality: 1, 4, 5, 10, 12, 14, 16, 18.

[0462] Test D Test units for evaluating control of Bemisia tabaci (Gennadius) by contact and / or systemic means consisted of small open containers with 12- to 14-day-old cotton plants inside. Prior to spray application, both cotyledons were removed from the plants, leaving one true leaf for the assay. Adult whiteflies were allowed to lay eggs on the plants and then removed from the test unit. Cotton plants infested with at least 15 eggs were tested for spraying.

[0463] Test compounds were formulated and sprayed at 50 and / or 10 ppm. After spraying, the test units were allowed to dry for 1 hour. The cylinders were then removed and the units were placed in a growth chamber and held at 28°C and 50-70% relative humidity for 13 days. Each test unit was then visually assessed for insect mortality.

[0464] Of the compounds of Formula 1 tested at 50 ppm, the following caused at least 70% mortality: 4, 5, 6, 7, 10, 12, 14, 16, 17, 18.

[0465] Test E Test units for evaluating control of the brown planthopper (Nilaparvata lugens (Stol)) by contact and / or systemic means consisted of small open containers containing 6-10 25-day-old rice stalks. White sand was added to the top of the soil prior to application of the test compound.

[0466] Test compounds were formulated and sprayed at 50 ppm and / or 10 ppm. After spraying with the formulated test compounds, the test units were allowed to dry for 1 hour before being post-infested with approximately 15-20 nymphs (15-17 days old). A black obscuring cap was placed on top of each test unit, and the test units were maintained in a growth chamber at 28°C and 65% relative humidity for 5 days. Each test unit was then visually assessed for insect mortality.

[0467] Of the compounds of Formula 1 tested at 10 ppm, the following produced at least 80% mortality: 6, 12.

[0468] Test F Test units for evaluating control of diamondback moth (Plutella xylostella (L.)) consisted of small open containers with 12- to 14-day-old mustard plants inside. These were pre-infested with approximately 50 neonate larvae that were distributed to the test units via corncob grits using an inoculum. After distribution to the test units, the larvae migrated onto the test plants.

[0469] The test compounds were formulated and sprayed at 250 and / or 50 ppm. After spraying the formulated test compounds, each test unit was allowed to dry for 1 hour before a black shielding cap was placed on top. The test units were kept in a growth chamber at 25°C and 70% relative humidity for 6 days. Plant feeding damage was then visually assessed based on ingested stems, and larvae were assessed for mortality.

[0470] Of the compounds of Formula 1 tested at 250 ppm, the following provided very good to excellent levels of control efficacy (less than 40% feeding damage and / or 100% mortality): 3, 4, 6, 7, 9, 20.

[0471] Of the compounds of Formula 1 tested at 50 ppm, the following provided very good to excellent levels of control efficacy (less than 40% feeding damage and / or 100% mortality): 9, 15.

Claims

1. Formula 1: 【Chemistry 1】 a compound, an N-oxide or a salt thereof selected from During the ceremony, L is 【Chemistry 2】 and the bond protruding to the left in each of L1, L2, L3, L4, and L5 is the bond projecting to the right in each of L1, L2, L4, and L5 is bonded to Q, and the bond projecting downward in L3 is bonded to Q; T is CHR, O, S, CO, or CS; R is H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; R １ a and R １ｂ are, respectively, H, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxyl or C １ ~C ６ haloalkoxyl; p is 1, 2, 3, or 4; A is N or CR ３ and R ２ is H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ４ Cycloalkyl, C ３ ~C ４ Halocycloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; R ３ is H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ４ Cycloalkyl, C ３ ~C ４ Halocycloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; R ４ is a 5-6 membered heterocyclic ring, each ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N atoms, wherein up to 2 ring members are C(=O), C(=S), S(=O), and S(=O) ２ wherein each ring is optionally substituted with up to five substituents independently selected from R, and r is the number of said substituents; Each R is independently H, cyano, halogen, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Haloalkenyl, C ２ ~C ６ Alkynyl, C ２ ~C ６ Haloalkynyl, C ３ ~C ６ Cycloalkyl, C ３ ~C ６ Halocycloalkyl, C ２ ~C ６ Cyanoalkyl, C １ ~C ６ Hydroxyalkyl, C ４ ~C １０ Alkylcycloalkyl, C ４ ~C １０ Cycloalkylalkyl, C ３ ~C ６ Cycloalkenyl, C ３ ~C ６ Halocycloalkenyl, C ２ ~C ６ Alkoxyalkyl, C ４ ~C １０ Cycloalkoxyalkyl, C ３ ~C １０ Alkoxyalkoxyalkyl, C ２ ~C ６ Alkylthioalkyl, C ２ ~C ６ Alkylsulfinylalkyl, C ３ ~C ６ Cycloalkoxy, C ３ ~C ６ Halocycloalkoxy, C ４ ~C １０ Cycloalkylalkoxy, C ２ ~C ６ Alkenyloxy, C ２ ~C ６ Haloalkenyloxy, C ２ ~C ６ Alkoxyalkoxy, C ２ ~C ６ Alkylcarbonyloxy, C １ ~C ６ Alkylthio, C １ ~C ６ Haloalkylthio, C ３ ~C ６ Cycloalkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Haloalkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Haloalkylsulfonyl, C ３ ~C ６ Cycloalkylsulfonyl, C １ ~C ６ Alkylamino, C ２ ~C ６ Dialkylamino, C １ ~C ６ Haloalkylamino, C ２ ~C ６ halodialkylamino, or C ３ ~C ６ cycloalkylamino; r is 1, 2, 3, 4, or 5; R ５ is H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ４ Cycloalkyl, C ３ ~C ４ Halocycloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; Q is a 5- or 6-membered aromatic ring containing carbon atoms and ring members selected from up to one oxygen atom, one sulfur atom, and two nitrogen atoms, each ring optionally having on a carbon atom ring member R ｗ and wherein s is the number of said substituents; and ｗ together form a 5- or 6-membered ring, for example, —OCF ２ O-, -OCH ２ O-, -OCF ２ S-, -OCH ２ CH ２ -, OCF ２ CF ２ O-, -OCR ５ =N-, -SCR ５ =N-, -CH=CR ５ -CH=CH-, or -CH=N-CR ５ can form =CH-; R ｗ are independently H, cyano, halogen, SF ５ , SC1, SO ２ Cl, SO ２ F, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C ２ ~C ６ Alkenyl, C ２ ~C ６ Haloalkenyl, C ２ ~C ６ Alkynyl, C ２ ~C ６ Haloalkynyl, C ３ ~C ６ Cycloalkyl, C ３ ~C ６ Halocycloalkyl, C ２ ~C ６ Cyanoalkyl, C １ ~C ６ Hydroxyalkyl, C ４ ~C １０ Alkylcycloalkyl, C ４ ~C １０ Cycloalkylalkyl, C ３ ~C ６ Cycloalkenyl, C ３ ~C ６ Halocycloalkenyl, C ２ ~C ６ Alkoxyalkyl, C ４ ~C １０ Cycloalkoxyalkyl, C ３ ~C １０ Alkoxyalkoxyalkyl, C ２ ~C ６ Alkylthioalkyl, C ２ ~C ６ Alkylsulfinylalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C ３ ~C ６ Cycloalkoxy, C ３ ~C ６ Halocycloalkoxy, C ４ ~C １０ Cycloalkylalkoxy, C ２ ~C ６ Alkenyloxy, C ２ ~C ６ Haloalkenyloxy, C ２ ~C ６ Alkoxyalkoxy, C ２ ~C ６ Alkylcarbonyloxy, C １ ~C ６ Alkylthio, C １ ~C ６ Haloalkylthio, C ３ ~C ６ Cycloalkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Haloalkylsulfinyl, C ３ ~C ６ Cycloalkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Haloalkylsulfonyl, C ３ ~C ６ Cycloalkylsulfonyl, C １ ~C ６ Alkylamino, C ２ ~C ６ Dialkylamino, C １ ~C ６ Haloalkylamino, C ２ ~C ６ halodialkylamino, or C ３ ~C ６ cycloalkylamino; A compound wherein s is 1, 2, 3, 4, or 5.

2. A is CR ３ and R ２ is H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ４ Cycloalkyl, C ３ ~C ４ Halocycloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; R ３ is H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ４ Cycloalkyl, C ３ ~C ４ Halocycloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; R ４ is a 5-6 membered heterocycle, each ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N atoms, wherein up to 2 ring members are independently selected from C(=O), C(=S), S(=O), and S(=O)2, and each ring or ring system is optionally substituted with up to 5 substituents independently selected from Rv, and r is the number of said substituents; Each R ｖ are independently H, halogen, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, or C １ ~C ６ haloalkoxy; r is 1, 2, 3, 4, or 5; R ５ is H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ４ Cycloalkyl, C ３ ~C ４ Halocycloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; Q is a 6-membered aromatic ring having 0-2 N on the ring, each ring optionally having R ｗ and is substituted with up to five substituents independently selected from: R ｗ are independently cyano, halogen, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Haloalkenyl, C ２ ~C ６ Alkynyl, C ２ ~C ６ Haloalkynyl, C １ ~C ６ Alkylthio, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Haloalkylsulfinyl, C １ ~C ６ Alkylsulfonyl, or C １ ~C ６ haloalkylsulfonyl; s is 1, 2, 3, 4, or 5; The compound of claim 1.

3. R ２ is H, halogen, or C １ ~C ４ is alkyl; R ３ is H, halogen, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; R ４ is selected from U-2 to U-49 or U52 to U61 shown in Appendix 1; r is 1 or 2; R ５ is H, halogen, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; R ｗ is C １ ~C ６ Haloalkoxy, C １ ~C ６ Haloalkyl, C ２ ~C ６ Haloalkenyl, C ２ ~C ６ Haloalkynyl, C １ ~C ６ Haloalkylthio, C １ ~C ６ Haloalkylsulfinyl, C １ ~C ６ haloalkylsulfonyl; s is 1 or 2; 3. The compound according to claim 1 or 2.

4. R ２ is H, halogen, or C １ ~C ４ is alkyl; R3 is H, halogen, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; R4 is selected from U-2 to U-49 or U52 to U61 shown in Appendix 1; r is 1 or 2; R ５ is H, halogen, or C １ ~C ４ is alkyl; R ｗ is C １ ~C ６ Haloalkoxy, C １ ~C ６ Haloalkyl, C ２ ~C ６ Haloalkenyl, C ２ ~C ６ Haloalkynyl, C １ ~C ６ Haloalkylthio, C １ ~C ６ Haloalkylsulfinyl, C １ ~C ６ haloalkylsulfonyl; s is 1 or 2; The compound according to any one of claims 1 to 3.

5. A is CR ３ and R ２ is H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ４ Cycloalkyl, C ３ ~C ４ Halocycloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; R ３ is H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ４ Cycloalkyl, C ３ ~C ４ Halocycloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; R ４ is a 5-6 membered heterocycle, each ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N atoms, wherein up to 2 ring members are independently selected from C(=O), C(=S), S(=O), and S(=O)2, and each ring or ring system is optionally substituted with up to 5 substituents independently selected from Rv, and r is the number of said substituents; Each R ｖ are independently H, halogen, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, or C １ ~C ６ haloalkoxy; r is 1, 2, 3, 4, or 5; R ５ is H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ４ Cycloalkyl, C ３ ~C ４ halocycloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; Q is a 6-membered aromatic ring with 0-2 N on the ring, and each ring optionally has R ｗ and is substituted with up to five substituents independently selected from: R ｗ are independently cyano, halogen, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Haloalkenyl, C ２ ~C ６ Alkynyl, C ２ ~C ６ Haloalkynyl, C １ ~C ６ Alkylthio, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Haloalkylsulfinyl, C １ ~C ６ Alkylsulfonyl, or C １ ~C ６ haloalkylsulfonyl; s is 1, 2, 3, 4, or 5; The compound of claim 1.

6. R ２ is H, halogen, or C １ ~C ４ is alkyl; R ３ is H, halogen, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; R ４ is selected from U-2 to U-49 or U52 to U61 shown in Appendix 1; r is 1 or 2; R ５ is H or halogen; R ｗ is C １ ~C ６ Haloalkoxy, C １ ~C ６ Haloalkyl, C ２ ~C ６ Haloalkenyl, C ２ ~C ６ Haloalkynyl, C １ ~C ６ Haloalkylthio, C １ ~C ６ Haloalkylsulfinyl, C １ ~C ６ haloalkylsulfonyl; s is 1 or 2; The compound according to any one of claims 1 to 5.

7. R ２ is H; R ３ is H or halogen; R ４ is selected from U-2 to U-49; Rv is H; r is 2; R ５ is H or halogen; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which optionally has R ｗ and is substituted with up to five substituents independently selected from: R ｗ Br, OCF ３ , SCF ３ , OCF ２ CFCF ３ , C.F. ３ , SOCF ３ , or SO ２ CF ３ That is, The compound according to any one of claims 1 to 6.

8. A is CR ３ and R ２ is H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ４ Cycloalkyl, C ３ ~C ４ Halocycloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; R ３ is H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ４ Cycloalkyl, C ３ ~C ４ Halocycloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; R ４ is a 5-6 membered heterocyclic ring, each ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N atoms, wherein up to 2 ring members are C(=O), C(=S), S(=O), and S(=O) ２ wherein each ring or ring system is optionally substituted with up to five substituents independently selected from R, and r is the number of said substituents; Each R is independently H, halogen, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, or C １ ~C ６ haloalkoxy; r is 1, 2, 3, 4, or 5; R ５ is H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ４ Cycloalkyl, C ３ ~C ４ Halocycloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; Q is a 6-membered aromatic ring with 0-2 N on the ring, and each ring optionally has R ｗ and is substituted with up to five substituents independently selected from: R ｗ are independently cyano, halogen, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Haloalkenyl, C ２ ~C ６ Alkynyl, C ２ ~C ６ Haloalkynyl, C １ ~C ６ Alkylthio, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Haloalkylsulfinyl, C １ ~C ６ Alkylsulfonyl, or C １ ~C ６ haloalkylsulfonyl; s is 1, 2, 3, 4, or 5; The compound of claim 1.

9. R ２ is H, halogen, or C １ ~C ４ is alkyl; R ３ is H, halogen, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; R ４ is selected from U-2 to U-49 or U52 to U61 shown in Appendix 1; r is 1 or 2; R ５ is H or halogen; R ｗ is C １ ~C ６ Haloalkoxy, C １ ~C ６ Haloalkyl, C ２ ~C ６ Haloalkenyl, C ２ ~C ６ Haloalkynyl, C １ ~C ６ Haloalkylthio, C １ ~C ６ Haloalkylsulfinyl, C １ ~C ６ haloalkylsulfonyl; s is 1 or 2; The compound according to any one of claims 1 to 8.

10. R ２ is H; R ３ is H or halogen; R ４ is selected from U-2 to U-49; R ｖ is H; r is 2; R ５ is H; Q is a phenyl, pyridinyl, pyrimidinyl, or pyrazinyl ring, each of which optionally has R ｗ and is substituted with up to five substituents independently selected from: R ｗ Br, OCF ３ , SCF ３ , OCF ２ CFCF ３ , C.F. ３ , SOCF ３ , or SO ２ CF ３ That is, The compound according to any one of claims 1 to 9.

11. A is CR ３ and R ２ is H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ４ Cycloalkyl, C ３ ~C ４ Halocycloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; R ３ is H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ４ Cycloalkyl, C ３ ~C ４ Halocycloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; R ４ is a 5-6 membered heterocyclic ring, each ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N atoms, wherein up to 2 ring members are C(=O), C(=S), S(=O), and S(=O) ２ wherein each ring or ring system is optionally substituted with up to five substituents independently selected from R, and r is the number of said substituents; Each R is independently H, halogen, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, or C １ ~C ６ haloalkoxy; r is 1, 2, 3, 4, or 5; R ５ is H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ４ Cycloalkyl, C ３ ~C ４ Halocycloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; Q is a 6-membered aromatic ring with 0-2 N on the ring, and each ring optionally has R ｗ and is substituted with up to five substituents independently selected from: R ｗ are independently cyano, halogen, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Haloalkenyl, C ２ ~C ６ Alkynyl, C ２ ~C ６ Haloalkynyl, C １ ~C ６ Alkylthio, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Haloalkylsulfinyl, C １ ~C ６ Alkylsulfonyl, or C １ ~C ６ haloalkylsulfonyl; s is 1, 2, 3, 4, or 5; The compound of claim 1.

12. R ２ is H, halogen, or C １ ~C ４ is alkyl; R ３ is H, halogen, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, or C １ ~C ４ haloalkoxy; R ４ is selected from U-2 to U-49 or U52 to U61 shown in Appendix 1; r is 1 or 2; R ５ is H, halogen, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ alkoxy, or C1-C4 haloalkoxy; R ｗ is C １ ~C ６ Haloalkoxy, C １ ~C ６ Haloalkyl, C ２ ~C ６ Haloalkenyl, C ２ ~C ６ Haloalkynyl, C １ ~C ６ Haloalkylthio, C １ ~C ６ Haloalkylsulfinyl, C １ ~C ６ haloalkylsulfonyl; s is 1 or 2; The compound according to any one of claims 1 to 12.

13. L is, 【Transformation 3】 、-CH ２ CH ２ - 【Chemistry 4】 、-CH ２ CH ２ CH ２ -COCH ２ CH ２ -CH ２ CH=CH-、-CH(OMe)CH=CH-、 【Transformation 5】 13. The compound of any one of claims 1, 11, and 12, wherein:

14. The compound is: 【Transformation 6】 3-fluoro-5-(2H-1,2,3-triazol-2-yl)-4-[(1E)-2-[4-(trifluoromethoxy)phenyl]ethenyl]pyridine, 【Transformation 7】 3-fluoro-5-(2H-1,2,3-triazol-2-yl)-4-[(1E)-2-[4-[(trifluoromethyl)thio]phenyl]ethenyl]pyridine, 【Transformation 8】 3-fluoro-5-(2H-1,2,3-triazol-2-yl)-4-[2-[4-(trifluoromethoxy)phenyl]ethyl]pyridine, 【Chemistry 9】 3-chloro-5-(2H-1,2,3-triazol-2-yl)-4-[2-[4-(trifluoromethoxy)phenyl]ethyl]pyridine, 【Chemistry 10】 3-fluoro-5-(1H-pyrazol-1-yl)-4-[2-[4-(trifluoromethoxy)phenyl]ethyl]pyridine, 【Chemistry 11】 3-chloro-5-(1H-pyrazol-1-yl)-4-[2-[4-(trifluoromethoxy)phenyl]ethyl]pyridine, 【Chemistry 12】 3-fluoro-5-(2H-1,2,3-triazol-2-yl)-4-[2-[4-(trifluoromethoxy)phenyl]cyclopropyl]pyridine, 【Chemistry 13】 3-chloro-5-(1H-1,2,3-triazol-1-yl)-4-[2-[4-(trifluoromethoxy)phenyl]cyclopropyl]pyridine, 【Chemistry 14】 3-fluoro-5-(2H-1,2,3-triazol-2-yl)-4-[2-[4-(trifluoromethyl)phenyl]cyclopropyl]pyridine, 【Chemistry 15】 3-chloro-5-(1H-1,2,3-triazol-1-yl)-4-[2-[4-(trifluoromethyl)phenyl]cyclopropyl]pyridine, and 【Chemistry 16】 3-fluoro-5-(1H-pyrazol-1-yl)-4-[2-[4-(trifluoromethyl)phenyl]cyclopropyl]pyridine 2. The compound of claim 1 selected from one or more compounds of the group consisting of:

15. 15. A composition comprising a compound of any one of claims 1 to 14 and at least one additional component selected from the group consisting of surfactants, solid diluents, and liquid diluents, optionally further comprising at least one additional biologically active compound or agent.

16. The at least one additional biologically active compound or agent may be abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, afidopiropen, amidoflumet, amitraz, avermectin, azadirachtin, azinphos-methyl, benfuracarb, bensultap, bifenthrin, bifenazate, bistrifluron, borate, bromantraniliprole, buprofezin, carbaryl, carbofuran, cartap, carsol, chlorantraniliprole, chlorfenapyr, chlorfluazuron, chlorpyrifos, or the like. chlorpyrifos-methyl, chromafenozide, clofentezine, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin, cycloxapride, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalodiamide, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dichlorantraniliprole, geldrin, diflubenzuron, dimefluthrin , dimehypo, dimethoate, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flometoquin, flonicamid, flubendiamide, flucythrinate, flufenerim, flufenoxuron, flufenoxystrobin, flufensulfon, fluopyram, flupyradifuron, fluvalinate, ta Fluvalinate, fonofos, formetanate, fosthiazate, halofenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, indazapiroxamet, indoxacarb, insecticidal soap, isofenphos, lufenuron, malathion, meperfluthrin, metaflumizone, metaldehyde, methamidophos, methidathion, methiodicarb, methomyl, methoprene, methoxychlor, methoxyfenozide, metofluthrin, monocrotophos, monofluorothrin, 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-(methylsulfonyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide amide, 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, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, Profenofos, profluthrin, propargite, protrifenbut, piflubumid, pymetrozine, pyrafluprole, pyrethrins, pyridaben, pyridalyl, pyrifluquinazon, pyriminostrobin, pyriprole, pyriproxyfen, rotenone, ryanodine, silafluofen, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulprofos, sulfoxaflor, tebufenozide 16. The composition of claim 15, wherein the insecticide is selected from the group consisting of tetrachlorolantraniliprole, tetrachlorvinphos, tetramethrin, tetramethylfluthrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, thioxazaphen, tolfenpyrad, tralomethrin, triazamate, trichlorfon, triflumezopyrim, triflumuron, Bacillus thuringiensis delta-endotoxin, entomopathogenic bacteria, entomopathogenic viruses, and entomopathogenic fungi.

17. A composition for protecting animals from invertebrate parasitic pests, comprising a parasitically effective amount of any one of claims 1 to 14 and at least one carrier.

18. 20. A method for controlling and combating invertebrate pests comprising contacting the invertebrate pests or their environment with a biologically effective amount of a compound, composition, or formulation according to any one of claims 1 to 17.

19. 20. The method of claim 18, wherein the invertebrate pest is a member of the order Hemiptera.

20. A treated seed comprising a compound of formula 1 or any one of claims 1 to 14 in an amount of about 0.0001 to 1% by weight of the seed before treatment.

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