Linked bicyclic compounds for controlling and eradicating invertebrate pests

Abstract

Disclosed are all of its geometric isomers and stereoisomers, N-oxides and salts, including formula 1 [Formula 1] TIFF2026528778000138.tif35170 (wherein L, R1, m, R2, R3, and R4 are as defined herein) The compound is [formula]. Disclosed are compositions containing the compound of formula 1, and methods for controlling and eradicating invertebrate pests, which also include contacting the invertebrate pest or its environment with a biologically effective amount of the compound or composition of the Disclosure.

Description

[Technical Field]

[0001] Cross-reference of related applications This application claims priority to U.S. Provisional Patent Application No. 63 / 531,348, filed August 8, 2023, which is incorporated herein by reference.

[0002] This disclosure relates to specific azole compounds suitable for agricultural or non-agricultural use, their N-oxides, salts and compositions, 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 and eradicating invertebrate pests is crucial for achieving high crop efficiency. Damage caused by invertebrate pests to growing and stored crops can significantly reduce productivity, leading to increased costs for consumers. Controlling and eradicating invertebrate pests is also important in forests, greenhouse crops, ornamental plants, seedling crops, stored foods and textiles, livestock, household products, turf, wood products, and public health and animal health. While many products are commercially available for these purposes, there is a continuing need for novel compounds that are more effective, cheaper, less toxic, more environmentally safe, or have different sites of action.

[0004] International Publication No. 2022 / 003510A1 discloses certain triazolopyridine compounds that are useful as pesticides. [Overview of the project] [Means for solving the problem]

[0005] This disclosure is based on Formula 1: [ka] (In the formula, L is CR 5 R 6 CR 5 R6 CR 5 R 6 、OCR 5 R 6 、CR 5 R 6 O、CR 5 R 6 NR 7 、NR 7 CR 5 R 6 、C(=E)NR 7 、NR 7 C(=E)、C(=E)CR 5 R 6 、CR 5 R 6 C(=E)、C(=CR 5 R 6 )、CR 5 =CR 6 or C(=E), and E is O, S or NR 8 and m is 0, 1, 2, 3, 4, 5, and each R 1 is independently halogen, cyano, nitro, hydroxy, SF5, C(O)NH2, C(O)NR 10 R 11 、C(=NR 13 )NR 10 R 11 、C(=NR 13 )R 14 、OC(O)R 14 、NR 10 R 11 、NR 13 C(O)R 14 、C(O)R 14 、S(O) n R 14 、OS(O) n R 14 、Si(R 14 )3、OSi(R 14 )3 or MQ a or unsubstituted or substituted by at least one R x is C1 - C6 alkyl, C2 - C6 alkenyl, C2 - C6 alkynyl, C3 - C6 cycloalkyl, C1 - C6 alkoxy, C3 - C6 cycloalkoxy, or two Rs on adjacent ring atoms1 The substituents, together with the carbon atoms to which they are bonded, form a 4- to 7-membered ring comprising a carbon atom and ring members selected from up to 3 heteroatoms independently selected from up to 2 oxygen atoms, 1 sulfur atom, and up to 3 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O)2, and the ring is unsubstituted or has at least one R x It has been replaced with, Each R 2 , R 3 , R 4 These are independently hydrogen, halogen, cyano, nitro, hydroxy, SF5, C(O)H, C(O)NH2, and C(O)NR 10 R 11 , C(=NR 13 )NR 10 R 11 , C(=NR 13 )R 14 ,OC(O)R 14 , NR 10 R 11 , NR 13 C(O)R 14 , C(O)R 14 , S(O) n R 14 OS(O) n R 14 , Si(R 14 )3, OSi(R 14 )3 or MQ a or non-substituted or at least one R x A C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C3-C6 cycloalkoxy, C2-C6 alkenyl or C2-C6 alkynyl that is substituted with (R) or two substituents on adjacent ring atoms 2 and R 3 or R 3 and R 4forms, together with the carbon atoms to which they are attached, a 4- to 7-membered ring containing ring members selected from carbon atoms and up to three heteroatoms independently selected from up to two oxygen atoms, one sulfur atom, and up to three nitrogen atoms, with up to two carbon atom ring members being independently selected from C(=O) and C(=S), and sulfur atom ring members being selected from S, S(O) or S(O)₂, said ring being unsubstituted or substituted with at least one R x and is substituted with M is a direct bond, O, S, S(O), S(O)₂ or NR 9 and is R 5 and R 6 are independently hydrogen, hydroxy, halogen, cyano, C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₆ cycloalkoxy, C₁-C₆ alkylthio or C₁-C₆ haloalkylthio, or R 5 and R 6 which are each attached to the same carbon atom, together with the carbon atom to which they are attached, form a 3- to 7-membered ring containing ring members selected from carbon atoms and up to three heteroatoms independently selected from one oxygen atom, one sulfur atom, and up to three nitrogen atoms, with up to two carbon atom ring members being independently selected from C(=O) and C(=S), and sulfur atom ring members being selected from S, S(O) or S(O)₂, said ring being unsubstituted or substituted with at least one R x or is substituted with CR 5 R 6 CR 5 R 6 in which case each R 5 and R 6is bonded to each of the first and second adjacent carbons, and together with the carbon atoms to which they are bonded, forms a 3- to 7-membered ring containing ring members selected from carbon atoms and up to 3 heteroatoms independently selected from one oxygen atom, one sulfur atom, and up to 3 nitrogen atoms, up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O), or S(O)2, the ring is unsubstituted or substituted with at least one R x and each R 7 is independently H, C(O)R 15 , or S(O)2R 15 , or Q b or is unsubstituted or substituted with at least one R x and is C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C2-C6 alkenyl or C2-C6 alkynyl, each R 8 is independently NR 10 R 11 , OR 12 , C(=NR 13 )R 14 , C(O)NR 10 R 11 , C(O)R 14 or S(O) n R 14 or is phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl or C2-C6 alkynyl each of which is unsubstituted or substituted with at least one R x , each R 9 is independently H, NR 10 R 11 , OR 12 , C(=NR 13 )R 14 , C(O)NR 10 R 11 , C(O)R 14 or S(O) n R 14 or is unsubstituted or substituted with at least one R xThese are phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl molecules substituted with: Each R x These are independently halogen, cyano, nitro, hydroxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C(O)NH2, C(O)NR 10 R 11 , C(=NR 13 )R 14 ,OC(O)R 14 , NR 10 R 11 , NR 14 C(O)R 14 , C(O)R 14 , S(O) n R 14 OS(O) n R 14 , Si(R 14 )3, OSi(R 14 )3 or Q b And, Each R 10 These are independently C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C2-C6 alkenyl or C2-C6 alkynyl, C(O)R 15 Or S(O)2R 15 Alternatively, each is either unsubstituted or a phenyl or a 5- or 6-membered heterocyclic aromatic ring substituted with at least one substituent independently selected from the group consisting of halogens, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy. Each R 11 These are independently H, C1-C6 alkyl or C1-C4 haloalkyl, or R 10 and R 11Together with the nitrogen atoms to which they are bonded, they form a 3- to 7-membered ring comprising a carbon atom and ring members selected from one oxygen atom, one sulfur atom, and up to three heteroatoms independently selected from up to three nitrogen atoms, wherein up to two carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O)2, and the ring is either unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogens, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy. Each R 12 This is a phenyl that is independently H, C1-C4 alkyl, C3-C6 cycloalkyl or C1-C4 haloalkyl or unsubstituted, or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy. Each R 13 H, OR 16 , S(O) n R 17 , C(O)OR 17 , C(O)R 17 or NHR 18 And, Each R 14 These are independently H, or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl or C2-C6 alkynyl, C1-C6 alkoxy, C3-C6 cycloalkoxy, or C(O)OR, each unsubstituted or substituted with at least one halogen, cyano or nitro. 17 , C(O)NR 22 R 23 , NR 22 R 23 , NR 24 C(O)R 17 , C(O)R 17 Or Q b And, Each R 15These are independently C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or NR 22 R 23 Alternatively, each is either unsubstituted or a phenyl or a 5- or 6-membered heterocyclic aromatic ring substituted with at least one substituent independently selected from the group consisting of halogens, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy. Each R 16 These are independently C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, and C(O)R 19 , S(O) n R 20 Or Q b And, Each R 17 These are independently C1-C4 alkyl or C1-C4 haloalkyl, R 18 C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C(O)R 19 Or C(O)OR 21 Alternatively, a phenyl that is unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogens, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy, Each R 19 This is a phenyl that is independently C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkylalkyl or C3-C6 halocycloalkylalkyl or unsubstituted, or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy. Each R 20This is a phenyl that is independently C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkylalkyl or C3-C6 halocycloalkylalkyl or unsubstituted, or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy. Each R 21 This is a phenyl that is independently C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkylalkyl or C3-C6 halocycloalkylalkyl or unsubstituted, or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy. Each R 22 These are independently H, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C2-C6 alkenyl or C2-C6 alkynyl, C(O)R 25 Or S(O)2R 25 Alternatively, each is either unsubstituted or a phenyl or a 5- or 6-membered heterocyclic aromatic ring substituted with at least one substituent independently selected from the group consisting of halogens, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy. Each R 23 These are independently H, C1-C6 alkyl or C1-C4 haloalkyl, or R 22 and R 23Together with the nitrogen atoms to which they are bonded, they form a 3- to 7-membered ring comprising a carbon atom and ring members selected from one oxygen atom, one sulfur atom, and up to two heteroatoms independently selected from up to two nitrogen atoms, wherein up to two carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O)2, and the ring is either unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogens, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy. Each R 24 These are independently H or C1-C4 alkyl groups. Each R 25 This is a phenyl or 5- or 6-membered heterocyclic aromatic ring that is independently C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy or unsubstituted, or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy. Each Q a Each is independently a phenyl, a 5- or 6-membered heterocyclic aromatic ring, or a 3- to 6-membered heterocyclic non-aromatic ring, each ring comprising a carbon atom and ring members independently selected from one oxygen atom, one sulfur atom, and up to four heteroatoms independently selected from up to four nitrogen atoms, with up to two carbon atom ring members independently selected from C(=O) and C(=S), and the sulfur atom ring member selected from S, S(O), or S(O)2, and each ring being unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogens, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy. Each Q bEach is independently a phenyl, a 5- or 6-membered heterocyclic aromatic ring, or a 3- to 6-membered heterocyclic non-aromatic ring, each ring comprising a carbon atom and a ring member selected from one oxygen atom, one sulfur atom, and up to four heteroatoms independently selected from up to four nitrogen atoms, with up to two carbon atom ring members independently selected from C(=O) and C(=S), and the sulfur atom ring member selected from S, S(O), or S(O)2, and each ring being unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogens, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy, and Each n is independently 0, 1, or 2. However, R 2 , R 3 and R 4 If is H and L is CH(OH), then R 1 It is anything other than 3-trifluoromethyl, and L is C(=O)NR 7 And when nitrogen is linked to the phenyl ring, R 2 , R 3 or R 4 (At least one of them is not H) This invention relates to compounds (including all geometric and stereoisomers), their N-oxides and salts, and compositions containing them, and their use for controlling and eradicating invertebrate pests.

[0006] The Disclosure also provides compositions comprising a compound of Formula 1, its N-oxide or salt, and at least one further component selected from the group consisting of surfactants, solid diluents, and liquid diluents. In one embodiment, the Disclosure also provides a composition for controlling and eradicating invertebrate pests, comprising a compound of Formula 1, its N-oxide or salt, and at least one further component selected from the group consisting of surfactants, solid diluents, and liquid diluents, further optionally comprising at least one further bioactive compound or agent.

[0007] The 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 a compound of Formula 1, its N-oxide, or a salt thereof (for example, as a composition described herein). The Disclosure also relates to such a method, in which 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 a salt thereof, and at least one further component selected from the group consisting of surfactants, solid diluents, and liquid diluents, and optionally further comprising a biologically effective amount of at least one further bioactive compound or agent.

[0008] The 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 plant.

[0009] The 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 an animal.

[0010] The 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 seeds.

[0011] The 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 thereof (e.g., as a composition described herein). The disclosure also relates to treated seeds (i.e., seeds that have been contacted with a compound of formula 1).

[0012] The disclosure also provides a method for increasing the vitality of a crop plant, comprising contacting the crop plant, the seed on which the crop plant is growing, or the location of the crop plant (e.g., a growing medium) with a biologically effective amount of a compound of Formula 1 (e.g., as a composition described herein).

[0013] This disclosure further provides a method for protecting animals from invertebrate parasitic pests, comprising administering to the animal a parasitically effective amount of a compound of formula 1, its N-oxide, or a salt thereof (for example, as a composition described herein). This disclosure also provides the use of a compound of formula 1, its N-oxide, or a salt thereof (for example, as a composition described herein) in the protection of animals from invertebrate pests. [Modes for carrying out the invention]

[0014] The terms “includes,” “contains,” “encompasses,” “has,” “has,” “contains,” “contains,” “characterized by,” or any other variation thereof as used herein, are intended to correspond to non-exclusive inclusion, subject to the expressly stated limitations. For example, a composition, mixture, process, or method that includes a list of components is not necessarily limited to these components alone and may include other components not expressly enumerated or components specific to such composition, mixture, process, or method.

[0015] The transitional phrase "consisting of" excludes any components, processes, or ingredients not specified. When used in a claim, the claim typically excludes the inclusion of materials other than those described, except for any incidental impurities. If the phrase "consisting of" appears in the body of the claim rather than immediately following the preamble, only the components described in that body are limited, and other components are not excluded from the claim as a whole.

[0016] The transitional phrase “essentially from” is used to define a composition or method that includes substances, processes, features, components, or elements in addition to those literally disclosed, provided that these additional substances, processes, features, components, or elements do not substantially affect the fundamental and novel features of the claimed disclosure. The term “essentially from” lies between “includes” and “consists of.”

[0017] If the applicant defines an embodiment or part thereof using open-ended terms such as "includes," it should be readily understood that such description should also be interpreted as describing embodiments that use terms such as "essentially consist of" or "consist of" (unless otherwise contradictory).

[0018] Furthermore, unless explicitly stated otherwise, "or" means inclusive or not exclusive. For example, condition A or B is satisfied by any of the following: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), and both A and B are true (or exist).

[0019] The indefinite articles “a” and “an” preceding any element or component of this disclosure are also intended to be non-limiting with respect to the number of occurrences (i.e., occurrences) of that element or component. Thus, “a” and “an” should be read as including one or at least one, and the singular form of a component or component also includes plurals unless it means that the number is clearly singular.

[0020] The term “invertebrate pests” as used 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, pillbugs, and Dipteropods. The term “gastropods” includes snails, slugs, and other Stylommatophora. The term “nematodes” includes members of the phylum Nematoda, such as herbivorous nematodes and zooparasitic helminth nematodes. The term "parasitic worm" includes all parasites, such as roundworms (Nematoda), heartworms (Nematoda, Seernentea), trematodes (Platyhelminthes, Tematoda), acanthocephalans (Acanthocephala), and tapeworms (Platyhelminthes, Cestoda).

[0021] With respect to this disclosure, “control and eradication of invertebrate pests” means the suppression of invertebrate pest development (including death, reduced feeding, and / or disruption of mating), and related expressions are defined similarly.

[0022] The term "agricultural" refers to the production of agricultural products such as food and fiber, and includes the growth of maize or corn, 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, eggplants, cruciferous plants and cucurbitaceous plants), potatoes, sweet potatoes, grapes, cotton, fruit trees (e.g., pears, drupes and citrus fruits), small fruit trees (e.g., berries and cherries), and other specialty crops (e.g., canola, sunflowers and olives).

[0023] The term "non-agricultural" refers to anything other than agricultural crops, such as horticultural crops (e.g., greenhouse plants, nursery plants, or ornamental plants that do not grow in fields), residential, agricultural, commercial, and industrial structures, turf (e.g., turf farms, pastures, golf courses, lawns, sports fields, etc.), wood products, storage products, afforestation and vegetation management, and public health (i.e., human) and animal health (e.g., domesticated animals, such as pets, livestock, and poultry, and undomesticated animals such as wildlife).

[0024] The term "crop vitality" refers to the rate of growth or biomass accumulation of a crop plant. "Increased vitality" refers to the increase in growth or biomass accumulation in a crop plant compared to an untreated control crop plant. The term "crop yield" refers to the return on crop material, both in terms of quantity and quality, obtained after harvesting a crop plant. "Increased crop yield" refers to the increase in crop yield compared to an untreated control crop plant.

[0025] The term "biologically effective amount" refers to a sufficient amount of a bioactive compound (e.g., a compound of Formula 1) to produce a desired biological effect when applied (i.e., in contact) to the invertebrate pest being controlled or its environment or the plant, the seed on which the plant grows or the location of the plant (e.g., the growth medium) in order to protect the plant from damage caused by the invertebrate pest or for other desired effects (e.g., increased plant vitality).

[0026] Non-agricultural uses include protecting animals from invertebrate parasitic pests by administering to the protected animal a parasitically effective (i.e., biologically effective) amount of the compounds of this disclosure, typically in the form of compositions formulated for veterinary use. The terms “parasitically effective” and “in a parasitically effective” as used in this disclosure and claims refer to an observable effect on an invertebrate parasitic pest to achieve protection of an animal from the pest. Parasitically effective effects typically relate to reducing the occurrence or activity of the target invertebrate parasitic pest. Such effects on the pest include necrosis, death, stunted growth, reduced motility or reduced ability to remain on or within a host animal, reduced feeding, and inhibited reproduction. These effects on invertebrate parasitic pests achieve control and management (including prevention, reduction, or elimination) of the spread or infection of parasites in animals.

[0027] In the above description, the term "alkyl," used alone or in compound terms such as "alkylthio" or "haloalkyl," includes linear or branched alkyl groups, such as methyl, ethyl, n-propyl, i-propyl, or various butyl, pentyl, or hexyl isomers. "Alkenyl" includes linear or branched alkenes, such as ethenyl, 1-propenyl, 2-propenyl, and different butenyl, pentenyl, and hexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes linear or branched alkynes, such as ethynyl, 1-propynyl, 2-propynyl, and different butynyl, pentynyl, and hexynyl isomers. "Alkynyl" may also include moieties composed of multiple triple bonds, such as 2,5-hexadienyl. "Alkylene" refers to linear or branched alkanediyl compounds. Examples of "alkylenes" include CH2, CH2CH2, CH(CH3), CH2CH2CH2, CH2CH(CH3), and different butylene isomers. "Alkenylene" refers to linear or branched alkenediyl compounds containing one olefin bond. Examples of "alkenylenes" include CH=CH, CH2CH=CH, CH=C(CH3), and different butenylene isomers. "Alkynylene" refers to linear or branched alkynediyl compounds containing one triple bond. Examples of "alkynylenes" include C≡C, CH2C≡C, C≡CCH2, and different butynylene isomers.

[0028] Examples of "alkoxy" include methoxy, ethoxy, n-propyloxy, isopropyloxy, and various butoxy, pentoxy, and hexyloxy isomers. "Alkoxyalkyl" means that the alkyl group is substituted with an alkoxy group. Examples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2, and CH3CH2OCH2CH2. "Alkoxyalkoxy" means that the alkoxy group is substituted with an alkoxy group. "Alkenyloxy" includes linear or branched alkenyloxy moieties. Examples of "alkenyloxy" include H2C=CHCH2O, (CH3)2C=CHCH2O, (CH3)CH=CHCH2O, (CH3)CH=C(CH3)CH2O, and CH2=CHCH2CH2O. "Alkynyloxy" includes linear or branched alkynyloxy moieties. Examples of "alkynyloxy" include HC≡CCH2O, CH3C≡CCH2O, and CH3C≡CCH2CH2O. Examples of "alkylthio" include branched or linear alkylthio moieties, such as methylthio, ethylthio, and different propylthio, butylthio, pentylthio, and hexylthio isomers. Examples of "alkylsulfinyl" include both enantiomers of the alkylsulfinyl group. Examples of "alkylsulfinyl" include CH3S(O)-, CH3CH2S(O)-, CH3CH2CH2S(O)-, (CH3)2CHS(O)-, and different butylsulfinyl, pentylsulfinyl, and hexylsulfinyl isomers. Examples of "alkylsulfonyl" include CH3S(O)2-, CH3CH2S(O)2-, CH3CH2CH2S(O)2-, (CH3)2CHS(O)2-, and different butylsulfonyl, pentylsulfonyl, and hexylsulfonyl isomers. "Alkylthioalkyl" means that the alkyl group is substituted with alkylthio. Examples of "alkylthioalkyl" include CH3SCH2, CH3SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2, and CH3CH2SCH2CH2."Alkylthioalkoxy" refers to an alkylthio substitution on an alkoxy. "Alkyldithio" refers to a branched or linear alkyldithio moiety. Examples of "alkyldithio" include CH3SS-, CH3CH2SS-, CH3CH2CH2SS-, (CH3)2CHSS-, and different 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" are defined similarly to the above examples.

[0029] Examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The term "alkylcycloalkyl" means alkyl substitution on the cycloalkyl moiety and includes, for example, ethylcyclopropyl, i-propylcyclobutyl, 3-methylcyclopentyl, and 4-methylcyclohexyl. The term "cycloalkylalkyl" means that the alkyl moiety is substituted with a cycloalkyl group. Examples of "cycloalkylalkyl" include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to linear or branched alkyl groups. The term "cycloalkoxy" means a cycloalkyl group linked via an oxygen atom, such as cyclopentyloxy and cyclohexyloxy. "Cycloalkylalkoxy" represents a cycloalkylalkyl group linked to an alkyl chain via an oxygen atom. Examples of "cycloalkylalkoxy" include cyclopropylmethoxy, cyclopentylethoxy, and other cycloalkyl moieties bonded to linear or branched alkoxy groups. "Cyanocycloalkyl" means a cycloalkyl group substituted with one cyano group. Examples of "cyanocycloalkyl" groups include 4-cyanocyclohexyl and 3-cyanocyclopentyl. Examples of "cycloalkenyl" groups include cyclopentenyl and cyclohexenyl groups, as well as groups having multiple double bonds, such as 1,3- and 1,4-cyclohexadienyl.

[0030] The term "halogen," when used alone, in a compound term such as "haloalkyl," or in a description such as "halogen-substituted alkyl," includes fluorine, chlorine, bromine, or iodine. Furthermore, when used in a compound term such as "haloalkyl" or in a description such as "halogen-substituted alkyl," the alkyl may be partially or completely substituted with the same or different halogen atoms. Examples of "haloalkyl" or "halogen-substituted alkyl" include F3C-, ClCH2-, CF3CH2-, and CF3CCl2-. The terms "halocycloalkyl," "haloalkoxy," "haloalkylthio," "haloalkenyl," and "haloalkynyl" are defined similarly to the term "haloalkyl." Examples of "haloalkoxy" include CF3O-, CCl3CH2O-, HCF2CH2CH2O-, and CF3CH2O-. Examples of "haloalkylthio" include CCl3S-, CF3S-, CCl3CH2S-, and ClCH2CH2CH2S-. Examples of "haloalkylsulfinyl" include CF3S(O)-, CCl3S(O)-, CF3CH2S(O)-, and CF3CF2S(O)-. Examples of "haloalkylsulfonyl" include CF3S(O)2-, CCl3S(O)2-, CF3CH2S(O)2-, and CF3CF2S(O)2-. Examples of "haloalkenyl" include (Cl)2C=CHCH2- and CF3CH2CH=CHCH2-. Examples of "haloalkynyl" include HC≡CCHCl-, CF3C≡C-, CCl3C≡C-, and FCH2C≡CCH2-. Examples of "haloalkoxyalkoxy" include CF3OCH2O-, ClCH2CH2OCH2CH2O-, Cl3CCH2OCH2O-, and branched alkyl derivatives.

[0031] "Alkylcarbonyl" refers to a linear or branched alkyl moiety bonded to the C(=O) portion. Examples of alkylcarbonyls include CH3C(=O)-, CH3CH2CH2C(=O)-, and (CH3)2CHC(=O)-. Examples of alkoxycarbonyls include CH3OC(=O)-, CH3CH2OC(=O)-, CH3CH2CH2OC(=O)-, (CH3)2CHOC(=O)-, and different butoxy- or pentoxycarbonyl isomers.

[0032] As used herein, the chemical abbreviations S(O) and S(=O) represent the sulfinyl moiety. As used herein, the chemical abbreviations SO2, S(O)2, and S(=O)2 represent the sulfonyl moiety. As used herein, the chemical abbreviations C(O) and C(=O) represent the carbonyl moiety. As used herein, the chemical abbreviations CO2, C(O)O, and C(=O)O represent the oxycarbonyl moiety. "CHO" means formyl.

[0033] R 25 However, if it is a 5- to 6-membered heterocyclic aromatic ring substituted with at least one substituent selected from the group of substituents described in the summary, the substituent may be bonded to the remainder of the compound of formula 1 through any available ring member of the heterocycle.

[0034] Q a Or Q b However, if it is a five- or six-membered heterocyclic aromatic ring substituted with at least one substituent as described in the summary, the substituent may be attached to the remainder of the compound of formula 1 via any available ring member of the five- or six-membered ring.

[0035] When it is shown that a variable group is arbitrarily attached to a certain position, for example (R 1 In the formula m (where r can be 0), hydrogen can be present at a position even if it is not listed in the definition of a variable group. When one or more positions of a group are described as "unsubstituted" or "non-substituted," hydrogen atoms are bonded to occupy free valences.

[0036] 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 alkylsulfonyls specify methylsulfonyl to butylsulfonyl, C2 alkoxyalkyls specify CH3OCH2-, C3 alkoxyalkyls specify, for example, CH3CH(OCH3)-, CH3OCH2CH2-, or CH3CH2OCH2-, and C4 alkoxyalkyls specify various isomers of alkyl groups substituted with alkoxy groups containing a total of four carbon atoms, examples of which include CH3CH2CH2OCH2- and CH3CH2OCH2CH2-.

[0037] If a compound is substituted with substituents having a subscript indicating that the number of substituents may exceed one, then the substituents (if they exceed one) are independently part of a defined group of substituents, for example [(R 1 )m], where m is selected from 0, 1, 2, 3, 4, or 5. A substituent that can be hydrogen, for example R 2 , R 3 or R 4 If a group contains a substituent, and that substituent is hydrogen, this is considered equivalent to the group being unsubstituted. When one or more positions of a group are described as "unsubstituted" or "unsubstituted," the hydrogen atom is bonded to occupy a free valence.

[0038] Unless otherwise specified, the “ring” or “ring system” as a component of Formula 1 is either a carbocyclic or heterocyclic system. The term “ring system” means a fused ring of two or more rings. The terms “bicyclic ring system” and “fused bicyclic ring system” refer to a ring system consisting of two fused rings, which may be “ortho-fused,” “bridged bicyclic,” or “spironicyclic.” An “ortho-fused bicyclic ring system” means a ring system in which the two constituent rings have two common adjacent atoms. A “bridged bicyclic ring system” is formed by bonding segments of one or more atoms to non-adjacent ring members of a ring. A “spironicyclic ring system” is formed by bonding segments of two or more atoms to the same ring member of a ring. The term “fused heterobicyclic ring system” means a fused bicyclic ring system in which at least one ring atom is not carbon. The term "ring member" refers to an atom or other part (e.g., C(=O), C(=S), S(O), or S(O)2) that forms the main chain of a ring or ring system.

[0039] The terms “carbocyclic ring,” “carbocyclic ring,” or “carbocyclic ring system” refer to a ring or ring system in which the atoms forming the ring's main chain are selected from carbon atoms only. The terms “heterocyclic ring,” “heterocyclic ring,” or “heterocyclic ring system” refer to a ring or ring system in which at least one atom forming the ring's main chain is not carbon, for example, nitrogen, oxygen, or sulfur. Typically, a heterocyclic ring contains four or fewer nitrogen atoms, two or fewer oxygen atoms, and two or fewer sulfur atoms. Unless otherwise specified, a carbocyclic ring or heterocyclic ring can be a saturated ring or an unsaturated ring. “Saturated” refers to a ring having a main chain of atoms linked to each other by single bonds, where, unless otherwise specified, the remaining valences are occupied by hydrogen atoms. Unless otherwise specified, an “unsaturated ring” can be partially unsaturated or completely 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 the valence bond method, and furthermore, the bonds between atoms in the ring contain as many double bonds as possible without accumulating double bonds (i.e., no C=C=C or C=C=N). The term “partially unsaturated ring” means a ring that contains at least one ring member bonded to an adjacent ring member via a double bond, and conceptually potentially accepts several non-overlapping double bonds between adjacent ring members (i.e., in its corresponding fully unsaturated form) more than the several double bonds present (i.e., in its partially unsaturated form).

[0040] Unless otherwise specified, heterocycles and cyclic systems may be bonded by either available carbon or nitrogen atoms through the substitution of hydrogen atoms on the carbon or nitrogen atoms.

[0041] "Aromatic" indicates that each ring atom is essentially coplanar, has a p orbital perpendicular to the ring plane, and is associated with the ring by (4n+2)π electrons (where n is a positive integer) according to Hückel's rule. The term "aromatic ring system" means a carbocyclic or heterocyclic ring system in which at least one ring of the ring system is aromatic. If a fully unsaturated carbocyclic ring satisfies Hückel's rule, the ring is also called an "aromatic ring" or "aromatic carbocyclic ring." The term "aromatic carbocyclic ring system" means a carbocyclic ring system in which at least one ring of the ring system is aromatic. If a fully unsaturated heterocyclic ring satisfies Hückel's rule, the ring is also called a "heteroaromatic ring" or "aromatic heterocyclic ring." The term "aromatic heterocyclic ring system" means a heterocyclic ring system in which at least one ring of the ring system is aromatic. The term "non-aromatic ring system" means a carbocyclic or heterocyclic ring system in which any of the rings of the ring system is aromatic, but which can be fully saturated, partially unsaturated, or fully unsaturated. The term "non-aromatic carbocyclic ring system" refers to a carbocyclic ring system in which none of the rings are aromatic. The term "non-aromatic heterocyclic ring system" refers to a heterocyclic ring system in which none of the rings are aromatic.

[0042] In relation to heterocycles, the term "optionally substituted" refers to a group having at least one non-hydrogen substituent that does not cause the loss of biological activity maintained by the unsubstituted or unsubstituted analogue. The following definitions used herein 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 substituents at each of its substituted positions, and each substitution is independent of the others.

[0043] As mentioned above, for example, Q a Or Q bSuch substituents may be 5- or 6-membered heterocyclic aromatic rings that are optionally substituted with one or more substituents selected from the group of substituents defined in the Outline. Examples of 5- or 6-membered unsaturated aromatic heterocycles optionally substituted with one or more substituents include rings U-2 to U-61 in Appendix 1, where Rv is any substituent defined in the Outline and r is an integer from 1 to 4, limited by the number of available positions on each U group. Since 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, for these U groups r is limited to an integer 1, and Rv being H and r being 1 means that the U group is unsubstituted and hydrogen is present at the position indicated by (Rv)r.

[0044] Appendix 1 [ka] [ka] [ka]

[0045] If a substituent is a 5- or 6-membered saturated or unsaturated non-aromatic heterocycle in which one or more substituents are optionally substituted with one or more substituents selected from the group of substituents defined in the outline, it should be noted that one or two carbon ring members of the heterocycle may optionally be oxidized forms of the carbonyl moiety.

[0046] Examples of 5- or 6-membered saturated or non-aromatic unsaturated heterocycles include rings G-1 to G-35 shown in Appendix 2. Note that where the bond on the G group is shown as floating, the G group can be bonded to the remainder of Formula 1 by hydrogen atom substitution via any available carbon or nitrogen on the G group. The optional substituents outlined below, denoted as Rv, can be bonded to any available carbon or nitrogen by hydrogen atom substitution. For these G rings, s is typically an integer between 1 and 5, limited by the number of available positions on each G group.

[0047] If a substituent includes a ring selected from G-28 to G-35, then G 2 Please note that this is selected from O, S, or N. 2 Note that if the atom is N, the nitrogen atom's valence can be completed by substitution with substituents corresponding to Rw as defined in the outline.

[0048] Appendix 2 [ka]

[0049] Note that while Rv groups are shown in structures U-2 to U-61, they are optional substituents and therefore do not need to be present. Note that when Rv is bonded to an atom, this is the same as when the atom is unsubstituted. Nitrogen atoms that require substitution to satisfy their valence are substituted with either H or Rv. Note that when the bond between (Rv)r and the U ring is shown as floating, (Rv)r can be bonded to any available carbon or nitrogen atom on the U ring. Note that when the bond on the U ring is shown as floating, the U group can be bonded to the remainder of formula 1 by substitution of hydrogen atoms via any available carbon or nitrogen on the U group. Note that some U rings can be substituted with fewer than four Rv groups (e.g., U-2 to U-5, U-7 to U-49, and U-52 to U-61).

[0050] A variety of synthetic methods are known in this art that enable the preparation of aromatic and non-aromatic heterocyclic rings and cyclic systems. For detailed reviews, please refer to the following literature: the 8-volume set of Comprehensive Heterocyclic Chemistry (ARKatritzky and CWRees editors-in-chief, Pergamon Press, Oxford, 1984) and the 12-volume set of Comprehensive Heterocyclic Chemistry II (ARKatritzky, CWRees, and EFVScriven editors-in-chief, Pergamon Press, Oxford, 1996).

[0051] The compounds of this disclosure can exist as one or more stereoisomers. Stereoiomers are isomers that have the same composition but differ in the spatial arrangement of atoms, and include enantiomers, diastereomers, cis-trans isomers (also known as geometric isomers), and atropisomers. Atropisomers arise from rotational binding around a single bond, and the rotational barrier is high enough to allow isolation of the isomeric species. Those skilled in the art will understand that if one stereoisomer is enriched with or separated from another stereoisomer, it may be more active and / or exhibit beneficial effects. Furthermore, those skilled in the art will know how to separate, enrich, and / or selectively prepare such stereoisomers. For a comprehensive description of all aspects of stereoisomerism, see the following literature: Ernest L. Eliel and Samuel H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, 1994.

[0052] To show the three-dimensional arrangement, bonds rising from the plane of the figure and pointing towards the observer are represented by solid wedge shapes, with the broader end of the wedge bonded to an atom rising from the plane of the figure and pointing towards the observer. Bonds pointing downwards from the plane of the figure and away from the observer are represented by dotted wedge shapes, with the broader end of the wedge bonded to an atom even further away from the observer. Wavy bonds indicate that the stereochemistry of the bond is unknown.

[0053] The compounds of Formula 1 may contain chiral centers. For example, the substituents of Formula 1 may contain chiral centers. The disclosure includes, in addition to racemic mixtures, compounds having configurations enriched with or substantially pure with these additional chiral centers.

[0054] The compounds of this disclosure may exist as one or more conformational isomers due to binding rotation around any bond in Formula 1. This disclosure includes mixtures of conformational isomers. Those skilled in the art will understand that not all nitrogen-containing heterocycles can form N-oxides because their nitrogen requires an available lone pair of electrons to be oxidized to an oxide. Those skilled in the art will recognize those nitrogen-containing heterocycles that can form N-oxides. Those skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for preparing N-oxides of heterocycles and tertiary amines are well known to those skilled in the art, including oxidizing heterocycles and tertiary amines with peroxy acids, e.g., peracetic acid and 3-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides, e.g., t-butyl hydroperoxide, sodium perborate, and dioxiranes, e.g., dimethyldioxiran.These methods for preparing N-oxides are widely described and reviewed in the literature; see, for example, the following: TLGilchrist, Comprehensive Organic Synthesis, vol.7, pp 748-750 (SVLey, Ed., Pergamon Press); M.Tisler and B.Stanovnik, Comprehensive Heterocyclic Chemistry, vol.3, pp.18-20, AJBoulton and A.McKillop, Eds., Pergamon Press; MRGrimmett and BRTKeene, Advances in Heterocyclic Chemistry, vol.43, pp.149-161, ARKatritzky, Ed., Academic Press; M.Tisler and B.Stanovnik, Advances in Heterocyclic Chemistry, vol.9, pp.285-291, ARKatritzky and AJBoulton, Eds., Academic Press and GWHCheeseman and ESGWerstiuk, Advances in Heterocyclic Chemistry, vol. 22, pp. 390-392, ARKatritzky and AJ Boulton, Eds., Academic Press.

[0055] Those skilled in the art recognize that, under environmental and physiological conditions, salts of compounds and their corresponding unsalted forms are in equilibrium, and therefore salts share the biological utility of the unsalted form. Accordingly, a variety of salts of the compounds of Formula 1 are useful for controlling and eradicating invertebrate pests. Examples of salts of the 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. If the compound of Formula 1 contains an acidic moiety such as a carboxylic acid or phenol, further examples of salts include those formed using organic or inorganic bases, such as pyridine, triethylamine, or ammonia, or amides, hydrides, sodium, potassium, lithium, calcium, magnesium, or barium amides, hydrides, hydroxides, or carbonates. Therefore, this disclosure includes compounds selected from Formula 1, their N-oxides, and suitable salts.

[0056] Compounds selected from Formula 1, their stereoisomers, tautomers, N-oxides, and salts typically exist in two or more forms; therefore, Formula 1 encompasses all crystalline and amorphous forms of the compounds represented by Formula 1. Amorphous forms include embodiments that are waxy and rubbery solids, as well as liquid embodiments such as solutions and melts. Crystalline forms include embodiments that are substantially a single crystalline form and embodiments that are mixtures of polymorphs (i.e., different crystalline forms). The term "polymorph" refers to a particular crystalline form of a compound that can crystallize into different crystalline forms, these forms differing in the arrangement and / or conformation of molecules within the crystal lattice. Polymorphs may have the same chemical composition, but their composition may differ due to the presence or absence of co-crystallized water or other molecules that may be weakly or strongly bonded within the lattice. Polymorphs may differ in chemical, physical, and biological properties such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspension, dissolution rate, and bioavailability. Those skilled in the art will understand that a particular polymorph of a compound represented by formula 1 may exhibit advantageous effects (e.g., suitability for preparing useful formulations, improved biological performance) compared to other polymorphs or mixtures 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, such as crystallization using a selected solvent and temperature. The compounds of this disclosure may exist as one or more crystalline polymorphs. This disclosure includes both individual polymorphs and mixtures of polymorphs (including mixtures in which one polymorph is enriched compared to the other polymorph). For a comprehensive discussion of polymorphism, see the following reference: R. Hilfiker, Ed., Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006.

[0057] The embodiments of this disclosure described in the summary include those described below. In the embodiments described below, Formula 1 includes its stereoisomers, N-oxides, and salts, and the phrase “compound of Formula 1” includes the definition of substituents as defined in the summary, unless otherwise defined in the embodiment.

[0058] Embodiment 1: L is CR 5 R 6 CR 5 R 6 CR 5 R 6 OCR 5 R 6 CR 5 R 6 O, CR 5 R 6 NR 7 , NR 7 CR 5 R 6 , C(=E)NR 7 , NR 7 C(=E), C(=E)CR 5 R 6 CR 5 R 6 C(=E), C(=CR) 5 R 6 ) or CR 5 =CR 6 The compound of formula 1.

[0059] Embodiment 1a:L is CR 5 R 6 CR 5 R 6 CR 5 R 6 OCR 5 R 6 CR 5 R 6 O, CR 5 R 6 NR 7 or NR 7 CR 5 R 6 The compound of formula 1.

[0060] Embodiment 1b:L is C(=E)NR 7 , NR 7 C(=E), C(=E)CR 5 R 6 CR 5 R 6 C(=E), C(=CR) 5 R 6 ) or CR 5 =CR 6 The compound described in Formula 1 or Embodiment 1.

[0061] Embodiment 1c:L is CR 5 R 6 A compound of formula 1 or embodiment 1.

[0062] Embodiment 1d:L is CR 5 R 6 CR 5 R 6 A compound of formula 1 or embodiment 1.

[0063] Embodiment 1e:L is an OCR 5 R 6 A compound of formula 1 or embodiment 1.

[0064] Embodiment f:L is CR 5 R 6 A compound of formula 1 or embodiment 1a, wherein the compound is O.

[0065] Embodiment 1g:L is CR 5 R 6 NR 7 A compound of formula 1 or embodiment 1a.

[0066] Embodiment 1h:L is NR 7 CR 5 R 6 A compound of formula 1 or embodiment 1a.

[0067] Embodiment 1i:L is C(=E)NR 7 A compound of formula 1 or embodiment 1a.

[0068] Embodiment 1j:L is NR 7 A compound of formula 1 or embodiment 1a, wherein C (=E).

[0069] Embodiment 1k:L is C(=E)CR 5 R 6 A compound of formula 1 or embodiment 1a.

[0070] Embodiment 1l:L is CR 5 R 6A compound of formula 1 or embodiment 1a, wherein C (=E).

[0071] Embodiment 1m:L is C(=CR 5 R 6 A compound of formula 1 or embodiment 1a, which is ( ).

[0072] Embodiment 1n:L is CR 5 =CR 6 A compound of formula 1 or embodiment 1a.

[0073] Embodiment 2: E is one of the compounds of formula 1 or Embodiments 1, 1b, 1i, 1j, 1k, or 1l, wherein E is O or S.

[0074] Embodiment 2a: A compound of formula 1 or Embodiment 2, wherein E is O.

[0075] Embodiment 2b: A compound of formula 1 or Embodiment 2, wherein E is S.

[0076] Embodiment 2c:E is NR 8 A compound of formula 1 or embodiment 2.

[0077] Embodiment 3: R 1 These are halogen, cyano, nitro, hydroxy, SF5, C(O)NH2, and C(O)NR 10 R 11 , C(=NR 13 )NR 10 R 11 , C(=NR 13 )R 14 ,OC(O)R 14 , NR 10 R 11 , NR 13 C(O)R 14 , C(O)R 14 , S(O) n R 14 OS(O) n R 14 , Si(R 14 )3, OSi(R 14 )3 or MQ a or non-substituted or at least one Rx A compound of formula 1 or a compound of the embodiment described above, which is a C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, or C3-C6 cycloalkoxy substituted with a C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkoxy.

[0078] Embodiment 3a:R 1 is S(O) n R 14 Or OS(O) n R 14 or non-substituted or at least one R x A compound of formula 1 or a compound of the embodiment described above, which is a C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, or C3-C6 cycloalkoxy substituted with a C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkoxy.

[0079] Embodiment 3b:R 1 is S(O) n R 14 or non-substituted or at least one R x A compound of formula 1 or a compound of the embodiment described above, which is a C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, or C3-C6 cycloalkoxy substituted with a C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkoxy.

[0080] Embodiment 3c:R 1 is S(O) n R 14 or non-substituted or at least one R x A compound of formula 1 or a compound of the embodiment described above, which is a C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C1-C6 alkoxy substituted with .

[0081] Embodiment 3d:R 1 is S(O) n R 14 or non-substituted or at least one R xA compound of formula 1 or a compound of the embodiment described above, which is a C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C1-C6 alkoxy substituted with .

[0082] Embodiment 3e:R 1 is S(O) n R 14 or non-substituted or at least one R x A compound of formula 1 or a compound of the embodiment described above, which is a C1-C6 alkyl, C2-C6 alkenyl, C1-C6 alkoxy or C1-C6 alkoxy substituted with .

[0083] Embodiment 3f:R 1 is S(O) n R 14 or non-substituted or at least one R x A compound of formula 1 or a compound of the embodiment described above, which is a C1-C6 alkyl or C1-C6 alkoxy substituted with .

[0084] Embodiment 3g:R 1 MQ a A compound that is either Formula 1 or one of Embodiments 1 to 2b.

[0085] Embodiment 3h:M is a direct bond of O, S, S(O), S(O)2, or NR 9 A compound of formula 1 or embodiment 3e.

[0086] Embodiment 3i:M is a compound of formula 1 or embodiment 3f, wherein the compound is directly bonded to O, S, S(O), S(O)2, or S(O)2.

[0087] Embodiment 3j:M is a compound of formula 1 or embodiment 3g, wherein M is directly bonded or is S, S(O), or S(O)2.

[0088] Embodiment 3k: M is a compound of formula 1 or embodiment 3j, wherein M is directly bonded or O.

[0089] Embodiment 3i: Each Q aThe compound is independently a phenyl, a 5- or 6-membered heterocyclic aromatic ring, or a 3- to 6-membered heterocyclic non-aromatic ring, each ring comprising a carbon atom and ring members independently selected from one oxygen atom, one sulfur atom, and up to four heteroatoms, up to two carbon atom ring members independently selected from C(=O) and C(=S), and the sulfur atom ring member selected from S, S(O), or S(O)2, and each ring is either unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogens, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy, any one of the compounds of Formula 1 or Embodiments 3g to 3k.

[0090] Embodiment 4: R 2 These are hydrogen, halogen, cyano, nitro, hydroxy, SF5, C(O)H, C(O)NH2, and C(O)NR 10 R 11 , C(=NR 13 )NR 10 R 11 , C(=NR 13 )R 14 ,OC(O)R 14 , NR 10 R 11 , NR 13 C(O)R 14 , C(O)R 14 , S(O) n R 14 OS(O) n R 14 , Si(R 14 )3, OSi(R 14 )3 or MQ a , non-substituted or at least one R x A compound of formula 1 or any one of the embodiments described above, which is a C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C3-C6 cycloalkoxy, C2-C6 alkenyl, or C2-C6 alkynyl substituted with .

[0091] Embodiment 4a:R 2These are hydrogen, halogen, cyano, nitro, hydroxy, SF5, C(O)NH2, and C(O)NR 10 R 11 , C(=NR 13 )NR 10 R 11 , C(=NR 13 )R 14 ,OC(O)R 14 , NR 10 R 11 , NR 13 C(O)R 14 , C(O)R 14 , S(O) n R 14 OS(O) n R 14 , Si(R 14 )3, OSi(R 14 )3 or MQ a Alternatively, a compound of formula 1 or any one of the compounds of the embodiments described above, which is a C1-C6 alkyl group.

[0092] Embodiment 4b:R 2 The compound of formula 1 or any one of the compounds of the embodiments described above, wherein is hydrogen, halogen, cyano, nitro, or hydroxy, or C1-C6 alkyl.

[0093] Embodiment 4c:R 2 The compound of formula 1 or any one of the compounds of the embodiments described above, wherein the compound is hydrogen, a halogen, or a C1-C6 alkyl group.

[0094] Embodiment 4d:R 2 The compound of formula 1 or any one of the compounds of the embodiments described above, wherein is hydrogen.

[0095] Embodiment 4e:R 2 This is a compound that is C1-C6 alkyl, and is one of the compounds of formula 1 or embodiments 1-4c.

[0096] Embodiment 5: R 3 These are hydrogen, halogen, cyano, nitro, hydroxy, SF5, C(O)H, C(O)NH2, and C(O)NR 10 R 11 , C(=NR13 )NR 10 R 11 , C(=NR 13 )R 14 ,OC(O)R 14 , NR 10 R 11 , NR 13 C(O)R 14 , C(O)R 14 , S(O) n R 14 OS(O) n R 14 , Si(R 14 )3, OSi(R 14 )3 or MQ a or non-substituted or at least one R x A compound of formula 1 or any one of the embodiments described above, which is a C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C3-C6 cycloalkoxy, C2-C6 alkenyl, or C2-C6 alkynyl substituted with .

[0097] Embodiment 5a:R 3 These are hydrogen, halogen, cyano, nitro, hydroxy, SF5, C(O)NH2, and C(O)NR 10 R 11 , C(=NR 13 )NR 10 R 11 , C(=NR 13 )R 14 ,OC(O)R 14 , NR 10 R 11 , NR 13 C(O)R 14 , C(O)R 14 , S(O) n R 14 OS(O) n R 14 , Si(R 14 )3, OSi(R 14 )3 or MQ a Alternatively, a compound of formula 1 or any one of the embodiments described above, which is a C1-C6 alkyl or C3-C6 cycloalkyl compound.

[0098] Embodiment 5b:R3 The compound of formula 1 or any one of the compounds of the embodiments described above is a compound of hydrogen, halogen, cyano, nitro or hydroxy or C1-C6 alkyl or C3-C6 cycloalkyl.

[0099] Embodiment 5c:R 3 The compound of formula 1 or any one of the compounds of the embodiments described above, wherein is hydrogen, a halogen, or a C1-C6 alkyl or C3-C6 cycloalkyl.

[0100] Embodiment 5d:R 3 The compound of formula 1 or any one of the compounds of the embodiments described above, wherein is H, C1-C6 alkyl or C3-C6 cycloalkyl.

[0101] Embodiment 5e:R 3 The compound of formula 1 or any one of the embodiments described above, wherein is H, Me, or c-Pr.

[0102] Embodiment 5f:R 3 is a compound of formula 1 or any one of the embodiments described above, wherein is Me or c-Pr.

[0103] Embodiment 5g:R 3 The compound is Me, and is either a compound of formula 1 or any one of the embodiments described above.

[0104] Embodiment 5f:R 3 is a compound of formula 1 or any one of the embodiments described above, wherein c-Pr is present.

[0105] Embodiment 6: R 4 These are hydrogen, halogen, cyano, nitro, hydroxy, SF5, C(O)H, C(O)NH2, and C(O)NR 10 R 11 , C(=NR 13 )NR 10 R 11 , C(=NR 13 )R 14 ,OC(O)R 14 , NR 10 R11 , NR 13 C(O)R 14 , C(O)R 14 , S(O) n R 14 OS(O) n R 14 , Si(R 14 )3, OSi(R 14 )3 or MQ a or non-substituted or at least one R x A compound of formula 1 or any one of the embodiments described above, which is a C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C3-C6 cycloalkoxy, C2-C6 alkenyl, or C2-C6 alkynyl substituted with .

[0106] Embodiment 6a:R 4 These are hydrogen, halogen, cyano, nitro, hydroxy, SF5, C(O)NH2, and C(O)NR 10 R 11 , C(=NR 13 )NR 10 R 11 , C(=NR 13 )R 14 ,OC(O)R 14 , NR 10 R 11 , NR 13 C(O)R 14 , C(O)R 14 , S(O) n R 14 OS(O) n R 14 , Si(R 14 )3, OSi(R 14 )3 or MQ a Alternatively, a compound of formula 1 or any one of the compounds of the embodiments described above, which is a C1-C6 alkyl group.

[0107] Embodiment 6b:R 4 The compound of formula 1 or any one of the compounds of the embodiments described above, wherein is hydrogen, halogen, cyano, nitro, or hydroxy, or C1-C6 alkyl.

[0108] Embodiment 6c:R4 The compound of formula 1 or any one of the compounds of the embodiments described above, wherein the compound is hydrogen, a halogen, or a C1-C6 alkyl group.

[0109] Embodiment 6d:R 4 The compound of formula 1 or any one of the compounds of the embodiments described above, wherein is hydrogen.

[0110] Embodiment 6e:R 4 The compound is Me, and is one of the compounds of formula 1 or embodiments 1 to 6c.

[0111] Embodiment 6f:R 4 F is a compound from formula 1 or any one of embodiments 1 to 6c.

[0112] Embodiment 7: R 5 and R 6 The compound is independently hydrogen, hydroxyl, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkoxy, C1-C6 alkylthio, or C1-C6 haloalkylthio, one of the compounds of Formula 1 or any one of Embodiments 1-1e and 3-6f.

[0113] Embodiment 7a:R 5 and R 6 The compound is independently hydrogen, hydroxyl, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkoxy, or C1-C6 alkylthio, and is one of the compounds of Formula 1 or any one of Embodiments 1-1e and 3-7.

[0114] Embodiment 7b:R 5 and R 6The compound is independently hydrogen, hydroxyl, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or C3-C6 cycloalkoxy, and is one of the compounds of Formula 1 or any one of Embodiments 1-1e and 3-7a.

[0115] Embodiment 7c:R 5 and R 6 The compound is independently hydrogen, hydroxyl, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy, and is one of the compounds of Formula 1 or any one of Embodiments 1-1e and 3-7b.

[0116] Embodiment 7d:R 5 and R 6 The compound is independently hydrogen, hydroxyl, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, or C1-C6 alkoxy, and is one of the compounds of Formula 1 or any one of Embodiments 1-1e and 3-7c.

[0117] Embodiment 7e:R 5 and R 6 The compound is independently hydrogen, hydroxyl, halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, or C3-C6 cycloalkyl, and is one of the compounds of Formula 1 or any one of Embodiments 1-1e and 3-7d.

[0118] Embodiment 7f:R 5 and R 6 The compound is independently hydrogen, hydroxyl, halogen, cyano, C1-C6 alkyl, or C1-C6 alkoxy, and is one of the compounds of Formula 1 or any one of Embodiments 1-1e and 3-7e.

[0119] Embodiment 7g:R 5 and R 6 The compound is independently hydrogen, hydroxyl, halogen, C1-C6 alkyl, or C1-C6 alkoxy, and is one of the compounds of Formula 1 or any of Embodiments 1-1e and 3-7f.

[0120] Embodiment 7h:R 5 and R 6 The compound is independently hydrogen, a halogen, a C1-C6 alkyl, or a C1-C6 alkoxy, and is one of any one of the compounds of Formula 1 or Embodiments 1-1e and 3-7g.

[0121] Embodiment 7i:R 5 and R 6 The compound is independently hydrogen, a halogen, or a C1-C6 alkoxy, and is one of any one of the compounds of Formula 1 or Embodiments 1-1e and 3-7h.

[0122] Embodiment 7j:R 5 and R 6 The compound is independently hydrogen, F, or MeO, and is one of the compounds of Formula 1 or any one of Embodiments 1-1e and 3-7i.

[0123] Embodiment 7k: R bonded to the same carbon 5 and R 6 Together with the carbon atoms to which they are bonded, they form a 3- to 7-membered ring comprising a carbon atom and ring members selected from one oxygen atom, one sulfur atom, and up to three heteroatoms independently selected from up to three nitrogen atoms, wherein up to two carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O)2, and the ring is unsubstituted or has at least one R x It is replaced with, or CR 5 R 6 CR 5 R 6 In this case, each R 5 and R 6The first and second adjacent carbon atoms are bonded to each of them and together with the carbon atoms to which they are bonded, they can form a 3- to 7-membered ring comprising a carbon atom and ring members selected independently from one oxygen atom, one sulfur atom and up to three heteroatoms, up to two carbon atom ring members independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O)2, and the ring is unsubstituted or has at least one R x A compound of formula 1 or any one of embodiments 1-1e and 3-6f, which is substituted with [the specified compound].

[0124] Embodiment 7i: R bonded to the same carbon 5 and R 6 Together with the carbon atoms to which they are bonded, they form a 3- to 7-membered ring comprising a carbon atom and ring members selected from one oxygen atom, one sulfur atom, and up to three heteroatoms independently selected from up to three nitrogen atoms, wherein up to two carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O)2, and the ring is unsubstituted or has at least one R x A compound of formula 1 or any one of embodiments 1-1e and 3-6f, which is substituted with [the specified compound].

[0125] Embodiment 7j:CR 5 R 6 CR 5 R 6 In this case, each R 5 and R 6 The first and second adjacent carbon atoms are bonded to each of them and together with the carbon atoms to which they are bonded, they can form a 3- to 7-membered ring comprising a carbon atom and ring members selected independently from one oxygen atom, one sulfur atom and up to three heteroatoms, up to two carbon atom ring members independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O)2, and the ring is unsubstituted or has at least one R xA compound of formula 1 or any one of embodiments 1-1e and 3-6f, which is substituted with [the specified compound].

[0126] Embodiment 8: R 7 H, C(O)R 15 , or S(O)2R 15 , or Q b or non-substituted or at least one R x A compound of any one of the following forms: Formula 1 or Embodiment 1, 1f-1g, and 3-6f, which is a C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl substituted with .

[0127] Embodiment 8a:R 7 is either unsubstituted or has at least one R x A compound of any one of the following forms: Formula 1 or Embodiment 1, 1f to 1g, and 3 to 6f, and 8, which is a C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 cycloalkyl, C2 to C6 alkenyl, or C2 to C6 alkynyl substituted with .

[0128] Embodiment 8b:R 7 These are H, C1-C6 alkyl, and C(O)R 15 Alternatively, S(O)2R 15 Or Q b The compound is one of the compounds of formula 1 or embodiment 1, 1f to 1g, 3 to 6f, and 8.

[0129] Embodiment 8c:R 7 These are H, C1-C6 alkyl, and C(O)R 15 Or S(O)2R 15 A compound of formula 1 or embodiment 8b.

[0130] Embodiment 8d:R 7 is H or S(O)2R 15 A compound of formula 1 or embodiment 8c.

[0131] Embodiment 8e:R 7 H, C1-C6 alkyl or C(O)R 15A compound of formula 1 or embodiment 8b.

[0132] Embodiment 8f:R 7 The compound is a compound of formula 1 or embodiment 8e, wherein the compound is H, C1-C6 alkyl.

[0133] Embodiment 8g:R 7 A compound of formula 1 or embodiment 8f, wherein H is present.

[0134] Embodiment 8h:R 7 The compound is a C1-C6 alkyl compound of formula 1 or embodiment 8f.

[0135] Embodiment 9: R 8 , NR 10 R 11 , OR 12 , C(=NR 13 )R 14 , C(O)NR 10 R 11 , C(O)R 14 Or S(O) n R 14 Or each is unsubstituted or at least one R x A compound of formula 1 or any one of embodiments 2 to 8h, which is a phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl substituted with phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl.

[0136] Embodiment 9a:R 8 , NR 10 R 11 , OR 12 , C(=NR 13 )R 14 , C(O)NR 10 R 11 , C(O)R 14 or S(O) n R 14 The compound of formula 1 or any one of the compounds described in embodiments 2 to 9 above.

[0137] Embodiment 9b:R 8 Each is either unsubstituted or has at least one R xA compound of any one of the following embodiments: Formula 1 or Embodiments 2-9, which is a phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl substituted with phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl.

[0138] Embodiment 9c:R 8 The compound of formula 1 or embodiment 9b is a phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl.

[0139] Embodiment 9d:R 8 is OR 12 A compound of formula 1 or embodiment 9a.

[0140] Embodiment 9e:R 12 The compound is a C1-C4 alkyl compound of formula 1 or embodiment 9d.

[0141] Embodiment 10: A compound of formula 1 or any one of the embodiments described above, where n is 0, 1, or 2.

[0142] Embodiment 11: A compound of formula 1 or any one of the embodiments described above, where m is 0, 1, 2, or 3.

[0143] Embodiment 11a:m is a compound of formula 1 or any one of the embodiments described above, wherein m is 0, 1, or 2.

[0144] Embodiment 11b:m is a compound of formula 1 or any one of the embodiments described above, wherein m is 1 or 2.

[0145] Embodiment 11c:m is a compound of formula 1 or any one of the embodiments described above, wherein the compound is 1.

[0146] Embodiment X. 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 Formula 1.

[0147] Embodiment X1. The method according to Embodiment X, wherein the invertebrate pest is a member of the order Hemiptera.

[0148] Embodiment X2. The method according to Embodiment X1, wherein the member of Hemiptera is a member of the suborder Homoptera.

[0149] Embodiment X2a. The method according to Embodiment X2, wherein the suborder Homoptera includes planthoppers from the families Cicadellidae and Delphacidae.

[0150] Embodiment X2b. The method according to Embodiment X2, wherein the suborder Homoptera includes aphids from the family Aphididae.

[0151] Embodiment X2c. The method according to Embodiment X2, wherein the suborder Homoptera includes whiteflies from the family Aleyrodidae.

[0152] Embodiment X3. The method according to Embodiment X2, wherein the Homoptera suborder includes CPH, GPA, CMA, BPH, and WF.

[0153] Embodiment X4. The suborder Homoptera includes Aphis fabae Scopoli (bean aphid), Aphis gossypii Glover (cotton aphid), Bemisia tabaci Gennadius (tobacco whitefly), Bemisia argentifolii Bellows & Perring (silverleaf whitefly), Dialeurodes citri Ashmead (citrus whitefly), and Trialeurodes vaporariorum Westwood (greenhouse whitefly), and Empoasca fabae Harris (potato leafhopper), Laodelphax striatellus Fallen (small brown planthopper), Macrosteles quadrilineatus Forbes (two-spotted leafhopper), Myzus persicae Sulzer (peach aphid), Nephotettix cincticeps Uhler (black leafhopper), Nephotettix nigropictus Stol (cross-striped black leafhopper), Nilaparvata lugens Stol (brown planthopper), Peregrinus maidis Ashmead (corn planthopper), Sogatella furcifera The method according to Embodiment X2, comprising Horvath (white-backed planthopper), Tagosodes orizicolus Muir (rice delphacid), Typhlocyba pomaria McAtee (white apple leafhopper), or a species of the genus Erythroneura (grape leafhopper).

[0154] Embodiment X5. The method according to Embodiment X1, wherein Hemiptera is a member of the suborder Heteroptera.

[0155] Embodiment X5a. The suborder Heteroptera includes Acrosternum hilare Say (green stink bug), Anasa tristis De Geer (sleeve bug), Blissus leucopterus leucopterus Say (American long-winged stink bug), Cimex lectularius Linnaeus (bed bug), Corythucha gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), Dichelops melacanthus Dallas (greenberry stink bug), and Dysdercus sturelus. *Euschistus suturellus Herrich-Schaeffer* (Cotton Stainer), *Euschistus heros Fabricius* (Neotropical Brown Stinkbug), *Euschistus servus Say* (Brown Stinkbug), *Euschistus variolarius Palisot de Beauvois* (One-Spotted Stinkbug), *Graptostethus* species (Seedbug Complex), *Halyomorpha halys Stol* (Brown Stinkbug), *Leptoglossus corculus Say* (Leaf-Footed Pine Seedbug), *Lygus lineolaris Palisot de Beauvois (green blind turtle), Nezara viridula Linnaeus (southern green stink bug), Oebalus pugnax Fabricius (rice bug), Oncopeltus fasciatusThe method according to Embodiment X5, comprising the large milkweed bug (Dallas) and the cotton flea beetle (Pseudatomoscelis seriatus Reuter).

[0156] Embodiment X6. The method according to Embodiment X5, wherein the suborder Heteroptera includes stink bugs from the family Pentatomidae.

[0157] Embodiment X7. The suborder Heteroptera includes Acrosternum hilare Say (green stink 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 stink bug), and Nezara viridula. The method according to Embodiment X6, comprising Linnaeus (Southern Green Stink Bug) and Oebalus pugnax Fabricius (Rice Stink Bug).

[0158] Embodiment X8. The suborder Heteroptera includes Anasa tristis De Geer (sleeve bug), Blissus leucopterus Say (American long-winged bug), Cimex lectularius Linnaeus (bed bug), Corythuca gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), Dysdercus suturellus Herrich-Schaffer (cotton stainer), Graptosthetus species (a group of seed bugs), and Leptoglossus corculus. The method according to Embodiment X5, comprising Say) (Leaf-footed pine seed bug), Lygus lineolaris Palisot de Beauvois (Green blind turtle), Oncopeltus fasciatus Dallas (Large milkweed bug), or Pseudatomoscelis seriatus Reuter (Cotton-free hopper).

[0159] The embodiments of this disclosure, including the prior embodiments 1 to X8 and all other embodiments described herein, may be combined in any way, and the descriptions of variables in the embodiments relate not only to the compounds of Formula 1 but also to starting compounds and intermediate compounds useful for preparing the compounds of Formula 1. In addition, the embodiments of this disclosure, including the prior embodiments 1 to X8 and all other embodiments described herein, and all combinations thereof, relate to the compositions and methods of this disclosure.

[0160] The combinations of embodiments 1 to X8 are shown by the following embodiments.

[0161] Embodiment A1.L is CR5 R 6 CR 5 R 6 CR 5 R 6 OCR 5 R 6 or CR 5 R 6 O, CR 5 R 6 NR 7 , NR 7 CR 5 R 6 , C(=E)NR 7 , NR 7 C(=E), C(=E)CR 5 R 6 CR 5 R 6 C(=E), C(=CR) 5 R 6 ), CR 5 =CR 6 Or C (=E), E is either O or S, n is 0, 1, or 2. m is 1, 2, or 3. R 1 is either unsubstituted or has at least one R x C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C3-C6 cycloalkoxy or MQ substituted with a And, R 2 These are hydrogen, halogen, cyano, nitro or hydroxy or C1-C6 alkyl, R 3 These are hydrogen, halogen, cyano, nitro or hydroxy or C1-C6 alkyl, C3-C6 cycloalkyl, R 4 These are hydrogen, halogen, cyano, nitro, hydroxy, SF5, C(O)NH2, and C(O)NR 10 R 11 , C(=NR 13 )NR 10 R 11 , C(=NR 13 )R 14 ,OC(O)R14 , NR 10 R 11 , NR 13 C(O)R 14 , C(O)R 14 , S(O) n R 14 OS(O) n R 14 , Si(R 14 )3, OSi(R 14 )3 or MQ a or C1-C6 alkyl, R 5 and R 6 These are independently hydrogen, hydroxyl, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkoxy, C1-C6 alkylthio, or C1-C6 haloalkylthio. R 7 H, C(O)R 15 , or S(O)2R 15 , or Q b or non-substituted or at least one R x These are C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C2-C6 alkenyl or C2-C6 alkynyl molecules substituted with, and R 8 , NR 10 R 11 , OR 12 , C(=NR 13 )R 14 , C(O)NR 10 R 11 , C(O)R 14 Or S(O) n R 14 Or each is unsubstituted or at least one R x A compound of formula 1, which is a phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl substituted with a phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl.

[0162] Embodiment A2.L is CR 5 R 6 OCR5 R 6 or CR 5 R 6 O, C(=E)NR 7 , NR 7 C(=E) or C(=E), E is either O or S, n is 0, 1, or 2. m is 1, 2, or 3. R 1 is either unsubstituted or has at least one R x C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C3-C6 cycloalkoxy or MQ substituted with a And, R 2 These are hydrogen, halogen, cyano, nitro or hydroxy or C1-C6 alkyl, R 3 These are hydrogen, halogen, cyano, nitro or hydroxy or C1-C6 alkyl, C3-C6 cycloalkyl, R 4 These are hydrogen, halogen, cyano, nitro, hydroxy, SF5, C(O)NH2, and C(O)NR 10 R 11 , C(=NR 13 )NR 10 R 11 , C(=NR 13 )R 14 ,OC(O)R 14 , NR 10 R 11 , NR 13 C(O)R 14 , C(O)R 14 , S(O) n R 14 OS(O) n R 14 , Si(R 14 )3, OSi(R 14 )3 or MQ a or C1-C6 alkyl, R 5 and R 6These are independently hydrogen, hydroxyl, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkoxy, C1-C6 alkylthio, or C1-C6 haloalkylthio. R 7 H, C(O)R 15 , or S(O)2R 15 , or Q b or non-substituted or at least one R x These are C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C2-C6 alkenyl or C2-C6 alkynyl molecules substituted with, and R 8 , NR 10 R 11 , OR 12 , C(=NR 13 )R 14 , C(O)NR 10 R 11 , C(O)R 14 Or S(O) n R 14 Or each is unsubstituted or at least one R x A compound of formula 1, which is a phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl substituted with a phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl.

[0163] Embodiment A3.L is CR 5 R 6 OCR 5 R 6 or CR 5 R 6 O, C(=E)NR 7 , NR 7 C(=E) or C(=E), E is O, n is 0, 1, or 2. m is 1, 2, or 3. R 2 These are hydrogen, halogen, cyano, nitro or hydroxy or C1-C6 alkyl, R 3These are hydrogen, halogen, cyano, nitro or hydroxy or C1-C6 alkyl, C3-C6 cycloalkyl, R 4 These are hydrogen, halogens, or C1-C6 alkyl groups. R 5 and R 6 These are independently hydrogen, hydroxyl, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkoxy, C1-C6 alkylthio, or C1-C6 haloalkylthio. R 7 H, C(O)R 15 , or S(O)2R 15 , or Q b or non-substituted or at least one R x These are C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C2-C6 alkenyl or C2-C6 alkynyl molecules substituted with, and R 8 , NR 10 R 11 , OR 12 , C(=NR 13 )R 14 , C(O)NR 10 R 11 , C(O)R 14 Or S(O) n R 14 Or each is unsubstituted or at least one R x A compound of formula 1 or embodiment 1A, which is a phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl substituted with a phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl.

[0164] Embodiment A4.L is CR 5 R 6 OCR 5 R 6 or CR 5 R 6 O, n is 0, 1, or 2. m is 1, 2, or 3. R1 is either unsubstituted or has at least one R x These are C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, and C3-C6 cycloalkoxy molecules substituted with [the appropriate compound]. R 2 These are hydrogen, halogen, cyano, nitro or hydroxy or C1-C6 alkyl, R 3 These are hydrogen, halogen, cyano, nitro or hydroxy or C1-C6 alkyl, C3-C6 cycloalkyl, R 4 These are hydrogen, halogen, cyano, nitro, hydroxy, SF5, C(O)NH2, and C(O)NR 10 R 11 , C(=NR 13 )NR 10 R 11 , C(=NR 13 )R 14 ,OC(O)R 14 , NR 10 R 11 , NR 13 C(O)R 14 , C(O)R 14 , S(O) n R 14 OS(O) n R 14 , Si(R 14 )3, OSi(R 14 )3 or MQ a or C1-C6 alkyl, R 5 and R 6 These are independently hydrogen, hydroxyl, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkoxy, C1-C6 alkylthio or C1-C6 haloalkylthio, and R 8 , NR 10 R 11 , OR 12 , C(=NR 13 )R 14 , C(O)NR 10 R11 , C(O)R 14 Or S(O) n R 14 Or each is unsubstituted or at least one R x A compound of formula I or embodiment 1A, which is a phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl substituted with a phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl.

[0165] Embodiment A5.L is C(=E)NR 7 , NR 7 C(=E) or C(=E), E is either O or S, n is 0, 1, or 2. m is 1, 2, or 3. R 1 is either unsubstituted or has at least one R x These are C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, and C3-C6 cycloalkoxy molecules substituted with [the appropriate compound]. R 2 These are hydrogen, halogen, cyano, nitro or hydroxy or C1-C6 alkyl, R 3 These are hydrogen, halogen, cyano, nitro or hydroxy or C1-C6 alkyl, C3-C6 cycloalkyl, R 4 These are hydrogen, halogen, cyano, nitro, hydroxy, SF5, C(O)NH2, and C(O)NR 10 R 11 , C(=NR 13 )NR 10 R 11 , C(=NR 13 )R 14 ,OC(O)R 14 , NR 10 R 11 , NR 13 C(O)R 14 , C(O)R 14 , S(O) n R 14 OS(O) n R 14, Si(R 14 )3, OSi(R 14 )3 or MQ a or C1-C6 alkyl, R 7 H, C(O)R 15 , or S(O)2R 15 , or Q b or non-substituted or at least one R x These are C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C2-C6 alkenyl or C2-C6 alkynyl molecules substituted with, and R 8 , NR 10 R 11 , OR 12 , C(=NR 13 )R 14 , C(O)NR 10 R 11 , C(O)R 14 Or S(O) n R 14 Or each is unsubstituted or at least one R x A compound of formula I or embodiment A1, which is a phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl compound substituted with a phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl.

[0166] Embodiment A6.L is CR 5 R 6 OCR 5 R 6 or CR 5 R 6 O, n is 0, 1, or 2. m is 1, R 2 These are hydrogen, halogen, cyano, nitro or hydroxy or C1-C6 alkyl, R 3 These are hydrogen, halogen, cyano, nitro or hydroxy or C1-C6 alkyl, C3-C6 cycloalkyl, R 4 These are hydrogen, halogen, cyano, nitro, hydroxy, SF5, C(O)NH2, and C(O)NR10 R 11 , C(=NR 13 )NR 10 R 11 , C(=NR 13 )R 14 ,OC(O)R 14 , NR 10 R 11 , NR 13 C(O)R 14 , C(O)R 14 , S(O) n R 14 OS(O) n R 14 , Si(R 14 )3, OSi(R 14 )3 or MQ a or C1-C6 alkyl, R 5 and R 6 These are independently hydrogen, hydroxyl, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkoxy, C1-C6 alkylthio or C1-C6 haloalkylthio, and R 8 , NR 10 R 11 , OR 12 , C(=NR 13 )R 14 , C(O)NR 10 R 11 , C(O)R 14 Or S(O) n R 14 Or each is unsubstituted or at least one R x A compound of formula I or embodiment 1A, which is a phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl substituted with a phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl.

[0167] Embodiment A7.L is C(=E)NR 7 , NR 7 C(=E) or C(=E), E is O, n is 0, 1, or 2. m is 1, R 1 is either unsubstituted or has at least one R x These are C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, and C3-C6 cycloalkoxy molecules substituted with [the appropriate compound]. R 2 These are hydrogen, halogen, cyano, nitro or hydroxy or C1-C6 alkyl, R 3 These are hydrogen, halogen, cyano, nitro or hydroxy or C1-C6 alkyl, C3-C6 cycloalkyl, R 4 These are hydrogen, halogen, cyano, nitro, hydroxy, SF5, C(O)NH2, and C(O)NR 10 R 11 , C(=NR 13 )NR 10 R 11 , C(=NR 13 )R 14 ,OC(O)R 14 , NR 10 R 11 , NR 13 C(O)R 14 , C(O)R 14 , S(O) n R 14 OS(O) n R 14 , Si(R 14 )3, OSi(R 14 )3 or MQ a or C1-C6 alkyl, R 7 H, C(O)R 15 , or S(O)2R 15 , or Q b or non-substituted or at least one R x These are C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C2-C6 alkenyl or C2-C6 alkynyl molecules substituted with, and R 8 , NR 10 R 11 , OR 12 , C(=NR13 )R 14 、 C(O)NR 10 R 11 、 C(O)R 14 or S(O) n R 14 or each is unsubstituted or substituted with at least one R x is phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl or C2-C6 alkynyl, a compound of formula I or embodiment 1A.

[0168] In embodiment A8.L is CR 5 R 6 、 CR 5 R 6 CR 5 R 6 、 OCR 5 R 6 or CR 5 R 6 O, C(=E)NR 7 、 NR 7 C(=E) or C(=E), E is O, R 1 is S(O) n R 14 or is unsubstituted or substituted with at least one R x is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C3-C6 cycloalkoxy, R 2 is hydrogen, R 3 is C1-C6 alkyl, R 4 is hydrogen, R 5 and R 6 are independently hydrogen, hydroxy, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkoxy, C1-C6 alkylthio or C1-C6 haloalkylthio, R 7 is H, C(O)R15 , or S(O)2R 15 , or Q b or non-substituted or at least one R x These are C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl molecules substituted with: R 8 , NR 10 R 11 , OR 12 , C(=NR 13 )R 14 , C(O)NR 10 R 11 , C(O)R 14 Or S(O) n R 14 Or each is unsubstituted or at least one R x These are phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl molecules substituted with: n is 0, 1 or 2, and The compound of formula 1, where m is 1.

[0169] Embodiment A9.L is CR 5 R 6 CR 5 R 6 CR 5 R 6 OCR 5 R 6 or CR 5 R 6 O, C(=E)NR 7 , NR 7 C(=E) or C(=E), E is O, R 1 is S(O) n R 14 or non-substituted or at least one R x A C1-C6 alkyl or C1-C6 alkoxy that is substituted with R 2 It is hydrogen, R 3 These are C1-C6 alkyl groups, R 4 is hydrogen, R 5 and R 6 are independently hydrogen, hydroxy, halogen, cyano, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkoxy, C1-C6 alkylthio or C1-C6 haloalkylthio, R 7 is H, C(O)R 15 or S(O)2R 15 or Q b or unsubstituted or at least one R x substituted C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C2-C6 alkenyl or C2-C6 alkynyl, R 8 is NR 10 R 11 OR 12 C(=NR 13 )R 14 C(O)NR 10 R 11 C(O)R 14 or S(O) n R 14 or each unsubstituted or at least one R x substituted phenyl, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl or C2-C6 alkynyl, n is 0, 1 or 2, and m is 1, a compound of formula 1.

[0170] Specific embodiments include compounds of formula 1 selected from the group consisting of the compounds shown in Table 1 and any combination of those compounds.

[0171]

Table 1

[0172] [Table 2]

[0173] [Table 3]

[0174] [Table 4]

[0175] [Table 5]

[0176] [Table 6]

[0177] [Table 7]

[0178] [Table 8]

[0179] More specific embodiments include the following: Compounds selected from the following group: N-(7-methyl[1,2,4]triazolo[1,5-a]pyridine-5-yl)-4-(trifluoromethyl)benzamide, 7-methyl-5-[[4-(trifluoromethyl)phenyl]methoxy][1,2,4]triazolo[1,5-a]pyridine, (7-methyl[1,2,4]triazolo[1,5-a]pyridine-5-yl)[4-(trifluoromethoxy)phenyl]methanone, 5-[fluoro[4-(trifluoromethoxy)phenyl]methyl]-7-methyl[1,2,4]triazolo[1,5-a]pyridine, 5-[Methoxy[4-(trifluoromethoxy)phenyl]methyl]-7-methyl[1,2,4]triazolo[1,5-a]pyridine, 7-methyl-5-[[4-(trifluoromethoxy)phenyl]methyl][1,2,4]triazolo[1,5-a]pyridine, 7-methyl-5-[[4-(trifluoromethyl)phenyl]methyl][1,2,4]triazolo[1,5-a]pyridine, 5-[fluoro[4-(trifluoromethyl)phenyl]methyl]-7-methyl[1,2,4]triazolo[1,5-a]pyridine, (6-Cyclopropyl-3αH-Inden-4-yl)(4-(trifluoromethoxy)phenyl)methanone, 5-(fluoro(4-(trifluoromethyl)phenyl)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-(3-fluoro-4-(trifluoromethyl)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-(3-fluoro-4-(trifluoromethoxy)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-(fluoro(3-fluoro-4-(trifluoromethoxy)phenyl)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 1-(7-cyclopropyl-[1,2,4]triazolo[1,5-a]pyridine-5-yl)-1-(4-(trifluoromethoxy)phenyl)ethane-1-ol, 5-(fluoro(4-(trifluoromethoxy)phenyl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-a]pyridine, 5-(2-fluoro-4-(trifluoromethyl)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-((2-fluoro-4-(trifluoromethoxy)phenyl)(methoxy)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-(fluoro(2-fluoro-4-(trifluoromethoxy)phenyl)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 7-iodo-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-isopropyl-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-(difluoromethyl)-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-Cyclopropyl-5-(4-(trifluoromethyl)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 5-(2-fluoro-4-(trifluoromethoxy)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 7-Bromo-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-Cyclopropyl-6-(2-(3-(trifluoromethyl)phenyl)cyclopropyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-Cyclopropyl-5-((3-fluoro-4-(trifluoromethyl)phenyl)(methoxy)methyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-Cyclopropyl-5-(fluoro(3-fluoro-4-(trifluoromethoxy)phenyl)methyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-Cyclopropyl-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, and 7-Cyclopropyl-5-(fluoro(4-(trifluoromethoxy)phenyl)methyl)-[1,2,4]triazolo[1,5-a]pyridine, and Any combination of the above compounds.

[0180] Embodiment Y1. A composition comprising a compound described in Formula 1 or any one of the previous embodiments, and at least one further component selected from the group consisting of surfactants, solid diluents, and liquid diluents, wherein the composition optionally further comprises at least one further bioactive compound or agent.

[0181] Embodiment Y1'. The following structure: [ka] A composition comprising α-[3-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyridine-5-methanol having and at least one further component selected from the group consisting of surfactants, solid diluents, and liquid diluents, wherein the composition optionally further comprises at least one further biologically active compound or agent.

[0182] Embodiment Y2. At least one further bioactive compound or agent is abamectin, acephate, acequinosyl, acetamiprid, acrinatrin, afidopiropene, amidoflumet, amitraz, avermectin, azadirachtin, azinphosmethyl, benziocarb, benfuracarb, bensultap, bifenthrin, bifenazate, bistriflurone, borate, bromantraniliprole, buprofezin, carbaryl, carbofuran, cartap, chlorantraniliprole, chlorfenapyr, chlorfluaz Chloropralethrin, Chlorpyrifos, Chlorpyrifos-methyl, Chromafenozide, Clofentezine, Clothianidin, Cyantraniliprole, Cyclaniliprole, Cyclobtrifluram, Cycloprotrin, Cycloxapride, Cietopyrafen, Cyflumetofen, Cyfluthrin, β-Cyfluthrin, Cyhalodiamid, Cyhalotrin, γ-Cyhalotrin, λ-Cyhalotrin, Cypermethrin, α-Cypermethrin, ζ-Cypermethrin, Cyprofuranilide, Cyromazine, Deltamethrin, Diafenthiurone, Diazino Dichlorantraniliprole, Dierdrin, Diflovidazine, Diflubenzuron, Dimefluthrin, Dimehypo, Dimethoate, Dinotefuran, Diophenolane, Emamectin, Endosulfan, Esfenvalerate, Ethiprole, Etofenprox, Ethoxazole, Phenazaquin, Fenbutatin oxide, Fenitrothion, Fenmesoditiaz, Phenothiocarb, Phenoxycarb, Fenpyroximate, Fenpropathrin, Fenvalerate, Fipronil, Flomethoquin, Flonicamide, Fluacryl Pyrim, fluazandinidine, flubendiamide, fluchlordiniliprole, flucitrinate, fluphenerim, flufenoxuron, fluphenoxystrobin, fluensulfone, fluhexaphon, flupentiophenox, fluopyram, flupyrimin, flupyradiflon, fluvalinate, taufluvalinate, fluxamethamide, phonophos, formetanate, fothiazate, halofenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, hydroprene, imidacloprid,Indazapiroxamet (N-(1-methylcyclopropyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide), indoxacarb, insecticide soap, isofenphos, isocycloceram, cappatefluthrin, quinoprene, lufenuron, malathion, meperfluthrin, metaflumizone, metaldehyde, methamidophos, methidathion, methiocarb, methomyl, methoprene, methoxychlor, methoxyphenozide, metofluthrin, monoclotophos, monofluorothrin, nicofluprole, nicotine, N-[1,1-dimethyl -2-(methylthio)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1,1-dimethyl-2-(methylsulfinyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1,1-dimethyl-2-(methylsulfonyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-(1-methylcyclopropyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1-(diflu Oromethyl)cyclopropyl]-2-(3-pyridinyl)-2H-indazole-4-carboxamide, nitenpyram, nithiazine, novaron, nobiflumulon, oxamyl, oxazosulfyl, parathion, parathion methyl, permethrin, phorate, fosalon, fosmet, phosphamidone, pyrimicarb, profenofos, profluthrin, propargit, protrefenbute, piflubamide, pymetrozine, pyrafluprole, pyrethrin (pyrethrum), pyridaben, pyridaryl, pyrifluquinazon, pyrimidifen, pyriminostrobi Pyriprole, pyriproxyfen, rotenone, ryanodine, silafluofen, spidoxamato, spinetoram, spinosad, spirobudiphen, spirodiclofen, spiromesifen, spirotetramato, sulprofos, sulfoxaflor, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, kappatefluthrin, terbufos, tetrachlorantraniliprole, tetrachlorvinfos, tetramethrin, tetramethylfluthrin, tetraniliprole, thiacloprid, thiamethoxam, thiodicarb, thiosultap,A composition according to Embodiment Y1 or Y1', selected from the group consisting of thiosultap-sodium, thiolantraniliprole, thioxazafen, tolfenpyrad, tralomethrin, trizamate, trichlorphon, trifluenfronate, triflumezopyrim, triflumulon, ticlopyrazoflor, Bacillus sphaericus, Bacillus thuringiensis δ-endotoxin, entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi, plant essences including synthetic extracts and unrefined oils, RNA interference-mediated target suppressors, thiolantraniliprole, and trifluenfronate.

[0183] Embodiment Y3. At least one further bioactive compound or agent is abamectin, acetamiprid, acrinatrin, afidopiropene, amitraz, avermectin, azadirachtin, benfuracarb, bensultap, bifenthrin, buprofezin, carbaryl, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin, cyfluthrin, β-cyfluthrin, cy Halotrin, γ-cyhalotrin, λ-cyhalotrin, cypermethrin, α-cypermethrin, ζ-cypermethrin, cyromazine, deltamethrin, dierdrin, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenitrothion, phenothiocarb, phenoxycarb, fenvalerate, fipronil, flometoquin, flonicamide, flubendiamide, flufenoxuron, Fluphenoxystrobin, fluensulfone, flupiprol, flupyradiflon, fluvalinate, formetanate, fostiazate, heptafluthrin, hexaflumurone, hydramethylnon, imidacloprid, indoxacarb, lufenuron, meperfluthrin, metaflumizone, methiocarb, methomyl, methoprene, methoxyfenozide, metofluthrin, monofluorothrin, nitenpyram, nithiazine, novaron, oxamyl, piflubamide, pymetrozine The composition according to Embodiment Y2, selected from the group consisting of pyrethrin, pyridaben, pyridaryl, pyriminostrobin, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramato, sulfoxaflor, tebufenozide, tetramethrin, tetramethylfluthrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, triflumesopyrim, triflumulon, Bacillus thuringiensis delta-endotoxin, all strains of Bacillus thuringiensis, and all strains of nuclear polyhedron disease virus.

[0184] Embodiment Y4. The composition according to any one of Embodiments Y1 to Y3, further comprising a liquid fertilizer.

[0185] Embodiment Y5. The composition according to Embodiment Y4, wherein the liquid fertilizer is aqueous.

[0186] Embodiment Y6. A soil immersion liquid formulation comprising the composition described in any one of Embodiments Y1 to Y3.

[0187] Embodiment Y7. A spray composition comprising the composition and propellant described in any one of Embodiments Y1 to Y3.

[0188] Embodiment Y8. A bait composition comprising the composition described in any one of Embodiments Y1 to Y3, one or more food materials, optionally an attractant, and optionally a wetting agent.

[0189] Embodiment Y9. A trap device for controlling invertebrate pests, comprising a bait composition as described in Embodiment Y8 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 enabling invertebrate pests to access the bait composition from a location outside the housing, and the housing being further configured to be positioned at or near a location of potential or known activity of invertebrate pests.

[0190] Embodiment Y10. A composition comprising the composition described in any of Embodiments Y1 to Y3, wherein the composition is a solid composition selected from dust, powder, granules, pellets, prill, pastyl, tablets, and filling film.

[0191] Embodiment Y11. The composition according to Embodiment Y10, which is water-dispersible or water-soluble.

[0192] Embodiment Y12. A liquid or dry formulation comprising the composition described in any one of Embodiments Y1 to Y3, used in drip irrigation systems, planting ridges, handheld sprayers, backpack sprayers, boom sprayers, ground sprayers, aerial spraying, unmanned aerial vehicles, or seed treatment.

[0193] Embodiment Y13. The formulation is the liquid or dry formulation described in Embodiment Y12, which is sprayed in a minute amount.

[0194] Of particular note is that the compounds of this disclosure exhibit activity to control and eradicate a variety of agricultural and non-agricultural invertebrate pests, characterized by favorable metabolic and / or soil persistence patterns.

[0195] Of particular note is that, due to the invertebrate pest control spectrum and economic importance, embodiments of this disclosure include the protection of crops from damage or injury caused by invertebrate pests by controlling and eradicating invertebrate pests. Due to their favorable translocation or osmotic properties in plants, the compounds of this disclosure also protect leaves or other plant parts that do not come into direct contact with the compound of Formula 1 or the composition containing this compound.

[0196] Of particular note as embodiments of the present disclosure are compositions comprising any of the compounds of the prior embodiments and any other embodiments described herein, as well as any combination thereof, and at least one further component selected from the group consisting of surfactants, solid diluents and liquid diluents, and optionally further comprising at least one further bioactive compound or agent.

[0197] Of particular note as embodiments of the present disclosure are compositions for controlling and eradicating invertebrate pests, comprising compounds of any of the prior embodiments and any other embodiments described herein, as well as any combination thereof, and at least one further component selected from the group consisting of surfactants, solid diluents and liquid diluents, wherein the composition optionally further comprises at least one further bioactive compound or agent. Embodiments of the present disclosure are methods for controlling and eradicating invertebrate pests, further comprising contacting the invertebrate pest or its environment with a biologically effective amount of any one of the compounds of the preceding embodiments (e.g., as a composition described herein).

[0198] Embodiments of the present disclosure also include compositions comprising any one of the compounds of the prior embodiments in the form of a soil immersion liquid formulation. Embodiments of the present disclosure further include a method for controlling and eradicating invertebrate pests, comprising contacting soil with a liquid composition as a soil immersion comprising a biologically effective amount of any one of the compounds of the prior embodiments.

[0199] Embodiments of the present disclosure also include a spray composition for controlling and eradicating invertebrate pests, comprising a biologically effective amount of any one compound of the prior embodiments and a propellant. Embodiments of the present disclosure also include a bait composition for controlling and eradicating invertebrate pests, further comprising a biologically effective amount of any one compound of the prior embodiments, one or more food materials, optionally an attractant and optionally a wetting agent. Embodiments of the present disclosure also include a device for controlling and eradicating invertebrate pests, comprising the bait composition and a housing configured to contain the bait composition, the housing having at least one opening sized to allow the invertebrate pest to pass through, thereby allowing the invertebrate pest to access the bait composition from a location outside the housing, and the housing further configured to be positioned at or near a location of potential or known activity of the invertebrate pest.

[0200] Embodiments of the present disclosure also include methods for protecting seeds from invertebrate pests, which include contacting seeds with a biologically effective amount of any one of the compounds of the preceding embodiments.

[0201] Embodiments of the present disclosure include methods for protecting animals from invertebrate parasitic pests, which also include administering to the animal an amount of any one of the compounds of the preceding embodiments that is parasitically effective.

[0202] Embodiments of the present disclosure are 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 (for example, as a composition described herein), but not methods of medical treatment of the human or animal body by therapeutic means.

[0203] This disclosure relates to a composition in which an invertebrate pest or its environment is brought into contact with a composition comprising a biologically effective amount of a compound of formula 1, its N-oxide or salt, and at least one further component selected from the group consisting of surfactants, solid diluents and liquid diluents, and optionally further comprising at least one further bioactive compound or agent in a biologically effective amount, provided that the method is not a method of medical treatment of the body of a human or animal by therapeutic means.

[0204] To prepare the compound of formula 1, one or more of the following methods and variations described in schemes 1 to 10 can be used. R in the compound of the following formula 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 The definitions of X, LG, and m are as defined above in the summary of this disclosure unless otherwise specified. Ambient temperature or room temperature is defined as approximately 20–25°C.

[0205] Triazole compound of formula 1a (wherein L is NR) 7 CO can be prepared by reacting a heterocyclic compound of formula 2a (wherein X is a halogen atom or a suitable leaving group) with an arylamide of formula 3a in the presence of a base and a catalyst such as copper(I) iodide, as shown in Scheme 1. Typical bases used include carbonates such as sodium carbonate or potassium carbonate, phosphates such as potassium triphosphate, and amines such as triethylamine. Typical solvents include THF, dioxane, toluene, DMF, DMSO, acetonitrile, or mixtures thereof. Typical reaction temperatures range from ambient temperature to the boiling point of the solvent. [ka]

[0206] Triazole compound of formula 1b (wherein L is OCR) 5 R 6 The alcohol can be prepared by reacting a heterocyclic compound of formula 2a (wherein X is a halogen atom or a suitable leaving group) with an alcohol of formula 3b in the presence of a base and in or without a catalyst such as copper(I) iodide, as shown in Scheme 2. Typical bases used include carbonates such as sodium carbonate or potassium carbonate, phosphates such as potassium triphosphate, and amines such as triethylamine. Typical solvents include THF, dioxane, toluene, DMF, DMSO, acetonitrile, or mixtures thereof. Typical reaction temperatures range from ambient temperature to the boiling point of the solvent. [ka]

[0207] Triazole compound of formula 1c (wherein L is CR) 5 R 6 And R 5(where hydroxyl is present) can be prepared by reacting the heterocyclic compound of formula 2b with the carbonyl compound of formula 3c in the presence of a strong base, as shown in Scheme 3. Typical bases used include BuLi, s-BuLi, t-BuLi, MeMgBr, MeMgCl, PhMgCl, LDA, LiHMDS, NaHMDS, and KHMDS. Typical solvents include THF, dioxane, toluene, diethyl ether, or mixtures thereof. Typical reaction temperatures range from -100°C to ambient temperature. General methods and procedures for regioselective metallization reactions are well known in the literature; see, for example, BLFinkelstein, J.Org.Chem. 1992, 57, 5538-5540. [ka]

[0208] The triazole compound of formula 1d (wherein formula 1 is C (=O)) is formula 1c (wherein formula R 6 Compounds of (where is a hydrogen atom) can be prepared as shown in Scheme 4 by reacting them with an oxidizing agent. Typical oxidizing agents used include air, oxygen, t-BuO2H, NaOCl, NBS, CrO3, KMnO4, DMSO / Ac2O, and Cl2 / pyridine. Typical solvents include water, THF, dioxane, toluene, DMF, DMSO, acetonitrile, or mixtures thereof.

[0209] The oxidation process can be carried out over a wide temperature range of approximately -70°C to 200°C, but it is noteworthy that rapid reaction times and high product yields are usually obtained at temperatures of approximately 20°C to 100°C. General methods and procedures for oxidizing alcohols to produce aketones are well known in the literature. For example, see RC Larock, Comprehensive Organic Transformations, VCH, 1989, New York, New York. [ka]

[0210] Equation 1e (wherein L is CR) 5 R 6 And R 5 Triazole compounds (not OH) can be prepared by reacting the compound of formula 1c with various agents, as shown in Scheme 5. Typical solvents include water, THF, dioxane, toluene, DMF, DMSO, acetonitrile, or mixtures thereof.

[0211] Such functional group transformations can be carried out over a wide temperature range of approximately -70°C to 200°C, but it is noteworthy that rapid reaction times and high product yields are usually obtained at temperatures of approximately 0°C to 100°C. General methods and procedures for converting alcohols to other functional groups are well known in the literature. For example, see RC Larock, Comprehensive Organic Transformations, VCH, 1989, New York, New York. [ka]

[0212] Triazole compound of formula 1f (wherein L is CR) 5 R 6 The compound of formula 2c (wherein LG is a halogen atom, a sulfonate group, or other leaving group) can be prepared by reacting the compound of formula 2c with the desired phenol in the presence of a base, as shown in Scheme 6. Typical bases used include carbonates such as sodium carbonate or potassium carbonate, phosphates such as potassium triphosphate, and amines such as triethylamine. Typical solvents include DCM, THF, dioxane, toluene, DMF, DMSO, acetonitrile, or mixtures thereof. Typical reaction temperatures range from ambient temperature to the boiling point of the solvent. [ka]

[0213] The triazole compound of formula 2c (wherein LG is a halogen atom, sulfonate group, or other detaching group) is obtained by reacting the compound of formula 2d (wherein R is usually an alkyl group) with SOCl2, as shown in Scheme 7, or by reacting (COCl)2,POCl3,PCl3,PCl5,PPh3 / BR 2 (For the introduction of halogen atoms, see Yingyong Huaxue, 1995, 12(3), 82-84) or it can be prepared by reacting it with MeSO2Cl, TolSO2Cl (for the introduction of sulfonate groups) in the presence of a base. Typical bases used include carbonates such as sodium carbonate or potassium carbonate, phosphates such as potassium triphosphate, and organic bases such as triethylamine and pyridine. Typical solvents include DCM, THF, dioxane, toluene, DMF, DMSO, acetonitrile, or mixtures thereof. Typical reaction temperatures range from ambient temperature to the boiling point of the solvent. [ka]

[0214] The triazole compound of formula 2d is a compound of formula 2e (wherein R is usually an alkyl group) and a metal hydride, such as LiAlH4, NaBH4, NaBH3(CN)(R 5 Or R 6 It can be prepared as shown in Scheme 8 by reaction with a Grignard reagent (or both are hydrogen atoms) or by reaction. Typical solvents include DCM, THF, dioxane, toluene, DMF, DMSO, acetonitrile, methanol, or mixtures thereof. Typical reaction temperatures range from -70°C to the boiling point of the solvent. [ka]

[0215] Formula 1: 1 g of triazole compound (wherein L is CONR) 7The compound can be prepared by the reaction of a heterocyclic compound of formula 2e (wherein R is usually a hydrogen atom or an alkyl group) with an amine of formula 3d, as shown in Scheme 9. Typical solvents include THF, dioxane, toluene, DMF, DMSO, acetonitrile, or mixtures thereof. Typical reaction temperatures range from -70°C to the boiling point of the solvent. [ka]

[0216] The triazole compounds of formula 2e can be prepared as shown in Scheme 10 by catalytic carbonylation of the compound of formula 2a (wherein X is a suitable leaving group such as a halogen) with carbon monoxide and the alcohol of formula 3e in the presence of a catalyst and a suitable ligand. The catalyst can be generated from a transition metal such as Pd (e.g., Pd(OAc)2 or Pd2(dba)3) and a monodentate or bidentate ligand such as PPh3, PCy3, Pt-Bu3, x-phos, xantphos, s-phos, or dppf. Typical bases used include carbonates such as sodium carbonate or cesium carbonate, phosphates such as potassium triphosphate, and amines such as ethyldiisopropylamine. Typical solvents include THF, dioxane, toluene, ethanol, DMF, or mixtures thereof. Typical reaction temperatures range from ambient temperature to the boiling point of the solvent. [ka]

[0217] It is recognized that some of the reagents and reaction conditions described above for preparing the compounds of Formula 1 may be incompatible with certain functional groups present in their intermediates. In such cases, incorporating a series of protection / deprotection or functional group interconversions into the synthesis facilitates obtaining the desired product. The use and selection of protecting groups will be obvious to those skilled in 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, standard synthetic steps not described in detail after introducing the given reagents shown in any of the individual schemes to complete the synthesis of the compounds of Formula 1. Those skilled in the art will also recognize that it may be necessary to combine the steps described in the above schemes in an order different from the specific order presented for preparing the compounds of Formula 1.

[0218] As those skilled in the art will further recognize, the compounds and intermediates of Formula 1 described herein can also be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

[0219] Without further detail, it is expected that those skilled in the art using the foregoing description will be able to make the most of this disclosure. Therefore, the following synthesis examples are to be interpreted merely as illustrations and do not limit the disclosure in any way. The steps in the following synthesis examples describe the steps in the overall synthetic transformation, and the starting materials for each step do not necessarily have to be prepared by a specific preparation run described in other examples or steps. Ambient temperature or room temperature is defined as approximately 20–25°C. Percentages are weight percentages, except for chromatographic solvent mixtures or unless otherwise specified. Parts and percentages for chromatographic solvent mixtures are volume-based unless otherwise indicated. MPLC refers to medium-pressure liquid chromatography using silica gel. 1 The 1H NMR spectrum is reported in ppm low field from tetramethylsilane, where 's' means singlet, 'd' means doublet, 'dd' means doublet-doublet, 'ddd' means doublet-doublet-doublet, 't' means triplet, 'm' means multiplet, and 'br s' means broad singlet. For mass spectral data, the reported value is the molecular weight (M) of the parent molecule ion formed by adding H+ (molecular weight 1) to the molecule, giving the M+1 peak observed by mass spectrometry using atmospheric pressure chemical ionization (AP+).

[0220] Schemes 1 to 10 show methods for preparing compounds of formula 1 having various substituents. Compounds of formula 1 having substituents other than those particularly noted in schemes 1 to 10 can be prepared by general methods known in the art of synthetic organic chemistry, including methods similar to those described in schemes 1 to 10. [Examples]

[0221] Synthesis Example 1 Preparation of (7-methyl-[1,2,4]triazolo[1,5-a]pyridine-5-yl)-[4(trifluoromethoxy)phenyl]methanol) (compound 15) To a solution of 7-methyl-[1,2,4]triazolo[1,5-a]pyridine (0.4 g, 3.004 mmol) in anhydrous tetrahydrofuran, n-butyllithium (2.441 mL, 3.905 mmol in 1.6 M hexane) was added dropwise at -78°C. The reaction was stirred at -78°C for 30 minutes. Then, 4-(trifluoromethoxy)benzaldehyde (0.742 g, 3.905 mmol) was added over 3 minutes as a solution in anhydrous tetrahydrofuran. The reaction mixture was stirred at -78°C for 15 minutes. After stirring the reaction mixture at 25°C for 45 minutes, it was quenched with saturated NH4Cl (30 mL), extracted with ethyl acetate (30 mL, 3 times), and dried over anhydrous sodium sulfate. The mixture was concentrated under vacuum and purified by conventional column chromatography (silica column, 35-70% ethyl acetate in hexane) to obtain (7-methyl-[1,2,4]triazolo[1,5-a]pyridine-5-yl)-[4-(trifluoromethoxy)phenyl]methanol (629 mg), which is the compound of the present invention, as a solid. 1 ¹H NMR (600MHz, CDCl3) δ ppm 8.31 (s, 1H), 7.55 (d, J=9Hz, 2H), 7.50 (s, 1H), 7.25 (m, 2H, overlapped with CDCl3), 6.58 (s, 1H), 6.32 (d, J=5Hz, 1H), 4.81 (s, J=5Hz, 1H), 2.45 (s, 3H).

[0222] Synthesis Example 2 Preparation of 5-[fluoro-[4-(trifluoromethoxy)phenyl]methyl]-7-methyl-[1,2,4]triazolo[1,5-a]pyridine (compound 8) 100 mg (0.309 mmol) of the compound prepared in Synthesis Example 1 and methylene chloride (3 mL) were added to a vial. Then, diethylaminosulfur trifluoride (0.1 g, 0.619 mmol) was added at 0°C, and the mixture was stirred overnight at 25°C. To ensure consumption of the substrate, half the amount of diethylaminosulfur trifluoride was added to the reaction vial. Once the reaction was complete as shown by TLC, the reaction was quenched with saturated NaHCO3 (20 mL) and diluted with dichloromethane (20 mL). The mixture was extracted with dichloromethane (3-fold, 20 mL), concentrated under vacuum, and purified by normal-phase column chromatography (silica column, ethyl acetate in hexane (15-50%)) to obtain 5-[fluoro-[4-(trifluoromethoxy)phenyl]methyl]-7-methyl-[1,2,4]triazolo[1,5-a]pyridine (56 mg), the compound of the present invention. 1 H NMR(600MHz,CDCl3)δ ppm 8.26(s,1H),7.59(d,J=8Hz,2H),7.55(s,1H),7.24(d,J=8Hz,2H),7.15(d,J=45Hz,1H),7.08(s,1H),2.54(s,3H)

[0223] Table 1-6. These relate to the structures shown below. [ka]

[0224] [Table 9]

[0225] [Table 10]

[0226] [Table 11]

[0227] [Table 12]

[0228] Table 13

[0229] Table 14

[0230] Table 15

[0231] Table 16

[0232] Table 17

[0233] Table 18

[0234] Table 19

[0235] Table 20

[0236] Table 21

[0237] Table 22

[0238] Table 23

[0239] Table 24

[0240] Table 25

[0241] Table 26

[0242] Table 27

[0243] Table 28

[0244] Table 29

[0245] Table 30

[0246] Table 31

[0247] Table 32

[0248] [Table 33]

[0249] [Table 34]

[0250] [Table 35]

[0251] [Table 36]

[0252] [Table 37]

[0253] [Table 38]

[0254] [ka] Table 2 Table 2 is identical to Table 1, except that the general structure has been changed to the structure described above.

[0255] [ka] Table 3 Table 3 is identical to Table 1, except that the general structure has been changed to the structure described above.

[0256] [ka] Table 4 Table 4 is identical to Table 1, except that the general structure has been changed to the structure described above.

[0257] [ka] Table 5 Table 5 is identical to Table 1, except that the general structure has been changed to the structure described above.

[0258] [ka] Table 6 Table 6 is identical to Table 1, except that the general structure has been changed to the structure described above.

[0259] [ka] Table 7 Table 7 is identical to Table 1, except that the general structure has been changed to the structure described above.

[0260] The compounds of this disclosure are generally used as active ingredients for controlling invertebrate pests in compositions, i.e., formulations, together with at least one further component selected from the group consisting of surfactants, solid diluents, and liquid diluents that function as carriers. The components of the formulation or composition are selected to be compatible with the physical properties of the active ingredient, the method of application, and environmental factors such as soil type, humidity, and temperature.

[0261] Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifying concentrates), suspensions, and emulsions (including microemulsions, oil-in-water emulsions, fluid concentrates, and / or suspendemulsions), which can be optionally thickened into gels. Common types of aqueous liquid compositions include soluble concentrates, suspension concentrates, capsule suspensions, concentrated emulsions, microemulsions, oil-in-water emulsions, fluid concentrates, and suspendemulsions. Common types of non-aqueous liquid compositions include emulsifying concentrates, microemulsifying concentrates, wettable powders, and oil dispersants.

[0262] Common types of solid compositions include powders, granules, pellets, granules, solid fumigants, tablets, and active ingredient-containing films (including seed coatings), which may be water-dispersible ("wettable") or water-soluble. Films and coatings formed from film-forming solutions or fluid suspensions are particularly useful for seed treatment. Active ingredients can be (micro)encapsulated and further formed into suspensions or solid formulations, or the entire active ingredient formulation can be encapsulated (or "overcoated"). Encapsulation can control or delay the release of the active ingredient. Emulsified granules combine the advantages of both emulsified concentrate formulations and dry granular formulations. High-concentration compositions are primarily used as intermediates for further formulations.

[0263] Sprayable formulations are typically diluted with a suitable medium before spraying. Such liquid and solid formulations are formulated to be easily dilutable in the spray medium, which is usually water, but may also be other suitable mediums such as aromatic or paraffinic hydrocarbons or vegetable oils. Spray volumes can range from approximately 1 to several thousand liters per hectare, but more typically from approximately 10 to several hundred liters per hectare. When sprayable formulations are applied to foliar treatment by aerial or ground application, or to plant growth media, they can be tank-mixed with water or other suitable mediums. Liquid and dry formulations can be directly metered and supplied to drip irrigation systems or metered and supplied to planting furrows at planting time. Liquid and solid formulations can be applied to crop seeds and other desired vegetation as a seed treatment before planting to protect growing roots and other underground plant parts and / or foliage via osmotic absorption.

[0264] The formulation typically contains an effective amount of the active ingredient, a diluent, and a surfactant, totaling 100 percent by weight within the approximate ranges shown below.

[0265] [Table 39]

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

[0267] Examples of liquid diluents include water, N,N-dimethylalkaneamide (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidone (e.g., N-methylpyrrolidinone), alkyl phosphate (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffin (e.g., white mineral oil, normal paraffin, isoparaffin), alkylbenzene, alkylnaphthalene, glycerin, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatic aliphatic hydrocarbons, alkylbenzenes, alkylnaphthalenes, ketones, such as cyclohexanone, 2-heptanone, isophorone, and 4-hydroxy-4-methyl-2-pentane. Non-acetates, such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isobornyl acetate, other esters such as alkylated lactic acid esters, dibasic esters, alkyl and aryl benzoates, γ-butyrolactones, and alcohols that may 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 include saturated and unsaturated fatty acids (typically C6-C6). 22Examples of liquid diluents include glycerol esters of plant and animal glycerol esters, such as plant seed oils and fruit oils (e.g., olive oil, castor oil, linseed oil, sesame oil, corn oil, peanut oil, sunflower oil, grape seed oil, safflower oil, cottonseed oil, soybean oil, rapeseed oil, coconut oil, palm kernel oil), animal fats (e.g., beef tallow, lard, cod liver oil, fish oil), and mixtures thereof. Alkylated fatty acids (e.g., methylated, ethylated, butylated) can also be used as liquid diluents, and these fatty acids can be obtained by hydrolysis of plant and animal glycerol esters and purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.

[0268] The solid and liquid compositions of this disclosure often contain one or more surfactants. When added to a liquid, surfactants (also known as “surfactants”) generally alter, and in most cases reduce, the surface tension of the liquid. Depending on the hydrophilic and lipophilic properties of the surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers, or defoamers.

[0269] Surfactants can be classified as nonionic, anionic, or cationic. Nonionic surfactants useful in this composition include, but are not limited to, alcohol alkoxylates, e.g., alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) prepared from this alcohol with ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides, e.g., ethoxylated soybean oil, castor oil, and rapeseed oil; alkylphenol alkoxylates, e.g., 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 reverse polymers where the terminal blocks are prepared from propylene oxide. Examples include block polymers, ethoxylated fatty acids, ethoxylated fatty acid esters and oils, ethoxylated methyl esters, ethoxylated tristyrylphenol (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-type polymers and star-type polymers, polyethylene glycol (PEG), polyethylene glycol fatty acid esters, silicone-based surfactants, and sugar derivatives, such as sucrose esters, alkyl polyglycosides, and alkyl polysaccharides.

[0270] Useful anionic surfactants include, but are not limited to, alkylaryl sulfonic acids and their salts, carboxylated alcohols or alkylphenol ethoxylates, diphenyl sulfonate derivatives, lignin and lignosulfonate derivatives, maleic acid or succinic acid or its anhydride, olefin sulfonates, phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and styrylphenol ethoxylates, protein-based surfactants, sarcosine derivatives, and styrylphenol ethersulfonates. Examples include phosphates, oils and fatty acid sulfates and sulfonates, ethoxylated alkylphenol sulfates and sulfonates, alcohol sulfates, ethoxylated alcohol sulfates, sulfonates of amines and amides such as N,N-alkyl taurates, sulfonates of benzene, cumene, toluene, xylene, and dodecyl and tridecylbenzene, sulfonates of condensed naphthalene, sulfonates of naphthalene and alkylnaphthalene, sulfonates of fractionally distilled petroleum, sulfosuccinates and sulfosuccinates and their derivatives, such as dialkyl sulfosuccinate salts.

[0271] Useful cationic surfactants include, but are not limited to, amides and ethoxylated amides, amines such as N-alkylpropanediamines, trippropyltriamines and dipropylenetetramines, amines such as 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 salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts, and amine oxides such as alkyldimethylamine oxide and bis-(2-hydroxyethyl)-alkylamine oxide.

[0272] Mixtures of nonionic and anionic surfactants, or mixtures of nonionic and cationic surfactants, are also useful in this composition. Nonionic, anionic, and cationic surfactants and their recommended uses are disclosed in various published literature, 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. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.

[0273] The compositions of this disclosure may also contain compounding aids and additives known to those skilled in the art as compounding aids (some of which are thought to function as solid diluents, liquid diluents or surfactants). Such compounding aids and additives can control pH (buffering agents), foaming during processing (antifoaming agents such as polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), growth of microorganisms in containers (antimicrobial agents), freezing of the product (antifreeze agents), color (dye / pigment dispersions), washability (film-forming agents or adhesives), evaporation (evaporation retarders), and other properties of the formulation. Examples of film-forming agents include polyvinyl acetate, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymers, polyvinyl alcohol, polyvinyl alcohol copolymers, and waxes. Examples of compounding aids and additives are listed in McCutcheon's Volume 2: Functional Materials, annual International and North American editions, published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co., and in PCT Public Publication No. 03 / 024222.

[0274] The compounds of Formula 1 and any other active ingredients are typically incorporated into the composition by dissolving the active ingredient in a solvent or by grinding it in a liquid or dry diluent. Solutions (including emulsifiable concentrates) can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is immiscible with water, an emulsifier is usually added to emulsify when the solvent containing the active substance is diluted with water. Slurries of active ingredients with a particle diameter of 2,000 μm or less can be wet-ground using a medium-agitated mill to an average particle diameter of less than 3 μm. Aqueous slurries can be made into a finished suspension concentrate (see, for example, U.S. Patent No. 3,060,084) or further processed by spray-drying to form granular wettable powders. Dry formulations typically require dry grinding to achieve an average particle diameter in the range of 2 to 10 μm. Powders and powders can be prepared by blending and usually by grinding (e.g., using a hammer mill or fluid energy mill). Granules and pellets can be prepared by spraying the active ingredient onto a pre-formed granular carrier or by using an agglomeration technique. See Browning, “Agglomeration”, Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and thereafter, and International Publication No. 91 / 13546. Pellets can be prepared as described in U.S. Patent No. 4,172,714. Wettable granules and water-soluble granules can be prepared as taught in U.S. Patent No. 4,144,050, U.S. Patent No. 3,920,442, and German Patent No. 3,246,493. The tablets may be prepared as taught in U.S. Patent No. 5,180,587, U.S. Patent No. 5,232,701, and U.S. Patent No. 5,208,030. The coatings may be prepared as taught in British Patent No. 2,095,558 and U.S. Patent No. 3,299,566.

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

[0276] In the following examples, all formulations are prepared by conventional methods. Compound numbers refer to the compounds in index tables A-C. Without further detail, it is expected that those skilled in the art using the preceding description can make the most of this disclosure. Therefore, the following examples should be interpreted as merely illustrative and not limiting this disclosure in any way. Unless otherwise specified, percentages are by weight.

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

[0278] Example B Wettable powder Compound 4 65.0% Dodecylphenol polyethylene glycol ether 2.0% Sodium lignosulfonate 4.0% Sodium aluminosilicate 6.0% Montmorillonite (calcined) 23.0%

[0279] Example C Granules Compound 8 10.0% Granular attapulgite (low volatility, 0.71 / 0.30 mm, USS No. 25-50 sieve) 90.0%

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

[0281] Example E emulsifiable concentrate Compound 15 10.0% Polyoxyethylene sorbitol hexoleate 20.0% C6~C 10 Fatty acid methyl ester 70.0%

[0282] Example F Microemulsion Compound 2 5.0% Polyvinylpyrrolidone-vinyl acetate copolymer 30.0% Alkyl polyglycoside 30.0% Glyceryl monooleate 15.0% Water 20.0%

[0283] Example G Seed treatment Compound 7 20.00% Polyvinylpyrrolidone-vinyl acetate copolymer 5.00% Montane wax 5.00% Calcium lignosulfonate 1.00% Polyoxyethylene / polyoxypropylene block copolymer 1.00% Stearyl alcohol (POE 20) 2.00% Polyorganosilane 0.20% Coloring agent: Red dye 0.05% Water 65.75%

[0284] Example H Fertilizer sticks Compound 9 2.5% Pyrrolidone-styrene copolymer 4.8% Tristyrylphenyl 16-ethoxylate 2.3% Talc 0.8% Corn starch 5.0% Time-release fertilizer 36.0% Kaolin 38.0% Water 10.6%

[0285] Example I Suspension concentrate Compound 13 35% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone-based defoaming agent 0.1% 1,2-Benzisothiazolin-3-one 0.1% Water 53.7%

[0286] Example J Underwater emulsion Compound 11 10.0% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone-based defoaming agent 0.1% 1,2-Benzisothiazolin-3-one 0.1% Aromatic petroleum hydrocarbons 20.0 Water 58.7%

[0287] Example K Oil dispersant Compound 12 25% Polyoxyethylene sorbitol hexaoleate 15% Organically modified bentonite clay 2.5% Fatty acid methyl ester 57.5%

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

[0289] The compounds of this disclosure exhibit activity against a wide range of invertebrate pests. These pests include invertebrates that live in various environments, such as plant stems and leaves, roots, soil, harvested crops or other foods, building structures, or animal hides. Examples of these pests include invertebrates that cause damage or harm to crops during growth and storage, forests, greenhouse crops, ornamental plants, seedlings, stored foods or textiles, or houses or other structures or their components, or are harmful to animal health or public health, by feeding on stems and leaves (including leaves, stems, flowers and fruits), seeds, wood, textiles, or animal blood or tissues. Those skilled in the art will understand that not all compounds are equally effective against all pests at all stages of growth.

[0290] Therefore, these compounds and compositions are agriculturally useful for protecting crops from herbivorous invertebrate pests, and non-agriculturally useful for protecting other horticultural crops and plants from herbivorous invertebrate pests. This practicality includes protecting crops and other plants (i.e., both agricultural and non-agricultural) that contain genetic material introduced by genetic engineering (i.e., gene transfer) or modified by mutagenesis to produce advantageous traits. Examples of such traits include resistance to herbicides, resistance to herbivorous pests (e.g., insects, mites, aphids, spiders, nematodes, snails, plant pathogenic fungi, bacteria, and viruses), improved plant growth, improved tolerance to poor 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 harvested products, or improved storage or processing properties of harvested products. Transgenic plants can be modified to express multiple traits. Examples of plants containing traits brought about by genetic engineering or mutation include YIELD GARD®, KNOCKOUT®, STARLINK®, BOLLGARD®, NuCOTN®, NEWLEAF®, and INVICTA RR. 2Examples include varieties of corn, cotton, soybeans, and potatoes that express insecticidal Bacillus thuringiensis toxins such as PRO®, as well as herbicide-resistant varieties of corn, cotton, soybeans, and rapeseed such as ROUNDUP READY®, LIBERTY LINK®, IMI®, STS®, and CLEARFIELD®, and crops that express N-acetyltransferase (GAT) to confer resistance to glyphosate herbicides or crops that contain the HRA gene to confer resistance to herbicides that inhibit acetolactate synthase (ALS). Because the compound and composition exhibit enhanced effects due to traits introduced by genetic engineering or modified by mutagenesis, they can enhance the phenotypic expression or efficacy of traits, or increase the effectiveness of the compound and composition in controlling invertebrate pests. In particular, this compound and composition exhibit enhanced effects through the phenotypic expression of proteins or other natural products toxic to invertebrate pests, enabling control of these pests beyond their additive effects.

[0291] The compositions of the present disclosure may optionally include fertilizer compositions comprising at least one phytonutrient selected from, for example, nitrogen, phosphorus, potassium, sulfur, calcium, magnesium, iron, copper, boron, manganese, zinc, and molybdenum. Of particular note are compositions comprising at least one fertilizer composition comprising at least one phytonutrient selected from nitrogen, phosphorus, potassium, sulfur, calcium, and magnesium. The compositions of the present disclosure further comprising at least one phytonutrient may be in liquid or solid form. Of particular note are solid formulations in the form of granules, small sticks, or tablets. Solid formulations comprising fertilizer compositions may be prepared by mixing the compounds or compositions of the present disclosure with the fertilizer composition together with the formulation components, and then preparing the formulation by methods such as granulation or extrusion. In addition, solid formulations may 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, for example, a pre-prepared fertilizer composition in the form of granules, small sticks, or tablets, and then evaporating the solvent.

[0292] Non-agricultural uses refer to the control of invertebrate pests in areas other than crop fields. Non-agricultural uses of this compound and composition include the control of invertebrate pests in stored grains, legumes and other foods, as well as in textiles such as clothing and carpets. Non-agricultural uses of this compound and composition also include the control of invertebrate pests in ornamental plants, forests, gardens, roadsides and railway construction sites, as well as in turf such as lawns, golf courses and pastures. Non-agricultural uses of this compound and composition also include the control of invertebrate pests in houses and other buildings that may be occupied by humans and / or companion animals, farm animals, pasture animals or other animals. Non-agricultural uses of this compound and composition also include the control of pests such as termites that may damage wood or other structural materials used in buildings.

[0293] Non-agricultural uses of the compounds and compositions of this disclosure also include protecting human and animal health by controlling and eradicating parasitic or disease-transmitting invertebrate pests. Control and eradication of animal parasites includes controlling and eradicating ectoparasites that infest the surface of the host animal's body (e.g., shoulders, armpits, abdomen, inner thighs) and endoparasites that infest the inside of the host animal's body (e.g., stomach, intestines, lungs, veins, subcutaneous tissue, lymphatic tissue). Examples of ectoparasites or disease-transmitting pests include chiggers, ticks, lice, mosquitoes, flies, mites, and fleas. Examples of endoparasites include heartworms, hookworms, and parasitic worms. The compounds and compositions of this disclosure are suitable for systemic and / or non-systemic control of parasitic outbreaks or infections in animals. The compounds and compositions of this disclosure are particularly suitable for eradicating ectoparasites or disease-transmitting pests. The compounds and compositions of this disclosure are suitable for controlling 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 controlling these parasites, mortality rates and performance degradation (with respect to meat, milk, wool, hides, eggs, honey, etc.) are reduced, and the application of compositions containing the compounds of this disclosure enables more economical and simpler livestock farming of animals.

[0294] Examples of agricultural and non-agricultural invertebrate pests include Lepidoptera, such as Noctuidae, including army worms, cutworms, loopers, heliothin (e.g., pink stem borer (Sesamia inferens Walker), cornstoke borer (Sesamia nonagrioides Lefebvre), southern army worm (Spodoptera eridania Cramer), fall armyworm (Spodoptera frugiperda JESmith), and white-striped fall armyworm (Spodoptera exigua hübner)). Huebner's worm, Egyptian armyworm (Spodoptera littoralis Boisduval), yellow-striped armyworm (Spodoptera ornithogalli Guenee), black cutworm (Agrotis ipsilon Hufnagel), velvet bean caterpillar (Anticarsia gemmatalis Huebner), green fruitworm (Lithophane antennata Walker), cabbage armyworm (Barathra brassicae Linnaeus), soybean looper (Pseudoplusia includens Walker), Cabbage Looper (Trichoplusia ni Huebner), False Tobacco Bud (Heliothis virescensFabricius), Pyralidae borers, Psychidae, webworms, cornworms, cabbage worms, skeletonizers (for example, European corn borer (Ostrinia nubilalis Huebner), navel orange worm (Amyelois transitella Walker), corn root webworm (Crambus caliginosellus Clemens), sodworm (Herpetogramma licarsisalis Walker), sugarcane stem borer (Chilo infuscatellus Snellen), tomato stem borer (Neoleucinodes elegantalis Green leaf roller (Cnaphalocrocis medinalis Guenee), grape leaf folder (Desmia funeralis Huebner), pickle worm (Diaphania nitidalis Stoll), cabbage center grab (Hellula hydralis Guenee), yellow stem borer (Scirpophaga incertulas Walker), white stem borer (Scirpophaga innotata Walker), top shoot borer (Scirpophaga nivella Walker) Fabricius), Darkhead Rice Baller (Chilo polychrysus Meyrick), Striped Rice Baller (Chilo suppressalis Walker)Sod webworms (Pyralidae: Crambinae subfamily), leaf rollers, budworms, seedworms, fruit worms (for example, codling moss (Cydia pomonella Linnaeus), grapeberry moss (Paralobesia viteana Clemens), oriental fruit moss (Grapholita molesta Busck), citrus force codling moss (Cryptophlebia leucotreta)) Meyrick), Citrus Baller (Gymnandrosoma aurantianum Lima), Red Banded Leaf Roller (Argyrotaenia velutinana Walker), Oblique Banded Leaf Roller (Choristoneura rosaceana Harris), Light Brown Apple Moss (Epiphyas postvittana Walker), European Grapeberry Moss (Eupoecilia ambiguella Huebner), Apple Bud Moss (Pandemis pyrusana Kearfott), Omnivorous Leaf Roller (Platynota stultana Walsingham) Walsingham)), Bird Flute Tree Tortoise (Pandemis cerasana Huebner), Brown Apple Tortoise (Pandemis heparana Dennis & Schiffermuller)Denis & Schiffermueller)) and many other economically important lepidoptera (e.g., diamondback moth (Plutella xylostella Linnaeus), pink ball worm (Pectinophora gossypiella Saunders)), Gypsy Moth (Lymantria dispar Linnaeus), Peach Fruit Baller (Carposina niponensis Walsingham), Peach Twig Baller (Anarsia lineatella Zeller), Potato Tuber Worm (Phthorimaea operculella Zeller), Spotted Teniform Leaf Miner (Phyllonorycter blancardella Fabricius), Asian Apple Leaf Miner (Lithocolletis ringoniella Matsumura), Rice Leaf Folder (Lerodea eufala Edwards) Eggs, larvae, and adults of the apple leaf miner (Leucoptera scitella Zeller), including cockroaches of the families Blattellidae and Blattidae, the order Blattodea (e.g., the oriental cockroach (Blatta orientalis Linnaeus), the Asian cockroach (Blatella asahinai Mizukubo), the German cockroach (Blatella germanica Linnaeus), the brown cockroach (Supella longipalpa Fabricius), and the American cockroach (Periplaneta americana). Linnaeus), brown cockroach (Periplaneta brunnea Burmeister), Madeira cockroach (Leucophaea maderae fabricius)Eggs, larvae, and adults of the cockroaches Fabricius, the American cockroach (Periplaneta fuliginosa Serville), the German cockroach (Periplaneta australasiae Fabr.), the gray cockroach (Nauphoeta cinerea Olivier), and the smooth cockroach (Symploce pallens Stephens), as well as weevils of the order Coleoptera (including Anthribidae, Bruchidae, and Curculionidae) (for example, the cotton weevil (Anthonomus grandis bohemian)). Boheman), rice water weevil (Lissorhoptrus oryzophilus Kuschel), granaria weevil (Sitophilus granarius Linnaeus), rice weevil (Sitophilus oryzae Linnaeus), annual bluegrass weevil (Listronotus maculicollis Dietz), bluegrass weevil (Sphenophorus parvulus Gyllenhal), grass weevil (Sphenophorus venatus vestitus Chittenden), Rocky Mountain weevil (Sphenophorus cicatristriatus Fahraeus), flea beetles of the Chrysomelidae family, cucumber beetles, root worms, leaf beetles, Colorado leaf beetles, leaf miners (for example, Colorado leaf beetle (Leptinotarsa ​​desemlineata seii)decemlineata Say)), Western corn rootworm (Diabrotica virgifera LeConte), scarab beetles of the Scarabaeidae family and other beetles (e.g., Japanese beetle (Popillia japonica Newman), spotted beetle (Anomala orientalis Waterhouse), northern masked chafer (Cyclocephala borealis Arrow), southern masked chafer (Cyclocephala immaculata Olivier or C. lurida Bland), dung beetle and white grub (species of the genus Aphodius) spp.), Black Turfgrass Athenius (Ataenius spretulus Haldeman), Green June Beetle (Cotinis nitida Linnaeus), Asiatic Garden Beetle (Maladera castanea Arrow), May / June Beetle (Phyllophaga spp.) and European Schaefer (Rhizotrogus majalis razumovskyi) Examples include eggs, leaf-feeding larvae, fruit-feeding larvae, root-feeding larvae, seed-feeding larvae, vesicular-feeding larvae, and adults of the Dermestidae family (carpet beetles), Elateridae family (click beetles), Scolytidae family (bark beetles), and Tenebrionidae family (confused flour beetles).

[0295] In addition, agricultural and non-agricultural pests include: eggs, adults, and larvae of Dermaptera, including earwigs of the family Forficulidae (e.g., European earwig (Forficula auricularia) Linnaeus, black earwig (Chelisoches morio) Fabricius)); Hemiptera, such as mirid bugs of the family Miridae; cicadas of the family Cicadidae; and leafhoppers of the family Cicadellidae (e.g., Empoasca spp.)), bed bugs of the family Cimicidae (e.g., Cimex lectularius Linnaeus), planthoppers of the families Fulgoridae and Delphacidae, treehoppers of the family Membracidae, psyllids of the families Liviidae, Psyllidae and Triozidae, whiteflies of the family Aleyrodidae, aphids of the family Aphididae, neap aphids of the family Phylloxeridae, and dwarf deer. Mealybugs of the family Pseudococcidae, scale insects of the families Coccidae, Diaspididae, and Margarodidae, lace bugs of the family Tingidae, stink bugs of the family Pentatomidae, and long-winged stink bugs of the family Lygaeidae (for example, the hairy long-winged stink bug (Blissus leucopterus hirtus)). Eggs, larvae, adults, and nymphs of *Leucopterus hirtus* (Montandon), *Blissus insularis* (Barber), and other seed bugs, spittlebugs of the family Cercopidae, stink bugs of the family Coreidae, and red-spotted stink bugs and cottonstainers of the family Pyrrhocoridae.

[0296] Examples of agricultural and non-agricultural pests include mites of the family Tetranychidae, such as spider mites and red mites (Acari, e.g., apple spider mite (Panonychus ulmi Koch), two-spotted spider mite (Tetranychus urticae Koch), and McDaniel's mite (Tetranychus mcdanieli McGregor)), and flat mites of the family Tenuipalpidae, such as greenhouse spider mite (Brevipalpus lewisi). McGregor))), Rust mites and bud mites of the family Eriophyidae, as well as leaf-feeding mites and mites important to human and animal health, namely house dust mites of the family Epidermoptidae, demodectic mange of the family Demodex mites, grain mites of the family Glycyphagidae, and mites of the family Ixodidae, commonly known as caterpillars (e.g., deer mites (Ixodes scapularis Say), Australian paralytic ticks (Ixodes holocyclus Neumann), American dog ticks (Dermacentor variabilis Say), and Lone star mites (Amblyomma americanum linneus). Ticks of the family Argasidae, commonly known as soft ticks (e.g., relapsing tick (Ornithodoros turicata Duges), common long-legged tick (Argas radiatus raiette)Raillet))), eggs, larvae, nymphs, and adults of scabies mites and Sarcoptidae, including grasshoppers, locusts, and crickets (Orthoptera, e.g., locusts and crickets (e.g., migratory locusts (e.g., Melanoplus sanguinipes Fabricius, M. differentialis Thomas), American grasshoppers (e.g., Schistocerca americana Drury), desert locusts (Schistocerca gregaria) Eggs, adults, and juveniles of Forsskal grasshoppers (Locusta migratoria Linnaeus), bush locusts (Zonocerus spp.), house crickets (Acheta domesticus Linnaeus), mole crickets (e.g., toni-mol cricket (Scapteriscus vicinus Scudder) and southern mole cricket (Scapteriscus borellii Giglio-Tos)), armyworms (e.g., serpentine vegetable leafminer (Liriomyza sativae) Blanchard))), fruit flies, gnats, fruit flies (Tephritidae), frit flies (e.g., Oscinella frit Linnaeus), soil maggots, houseflies (e.g., Musca domestica Linnaeus), dwarf houseflies (e.g., Fannia canicularis Linnaeus, F. femoralis stein)Stein), stable flies (e.g., Stomoxys calcitrans Linnaeus), faceflies, hornflies, black flies (e.g., species of the genus Chrysomya), Species of the genus Phormia and other musk flies, botflies (e.g., species of the genus Tabanus), botflies (e.g., species of the genus Gasterophilus, species of Oestrus, species of Hypoderma), blind flies (e.g., species of Chrysops), sheep flies (e.g. Melophagus ovinus Linnaeus) and other Brachella, mosquitoes (e.g., species of Aedes, species of Anopheles, species of Culex) This includes eggs, adults, and immature flies of the order Diptera, such as black flies (e.g., species of the genera Prosimulium, Simulium, Liriomyza, leafminers, sand flies, fungus gnats, and other species of Nematocera), onion thrips (Thrips tabaci Lindeman), flower thrips (Frankliniella, Frankliniella), and other leaf-feeding thrips, such as the order Thripsidae (e.g., eggs, adults, and immature ants of the order Thripsidae, such as the Florida ant (Camponotus floridanus buckley) Buckley), red carpenter ant (Camponotus ferrugineus Fabricius), black carpenter ant (Camponotus pennsylvanicus De Geer), white-legged flat ant (Technomyrmex albipes F.Smith), glossy large ant (Pheidole sp. species).)), including ants of the Formicidae family such as Tapinoma melanocephalum Fabricius, pests of the Hymenoptera order, pharaoh ants (Monomorium pharaonis Linnaeus), small imported fire ants (Wasmannia auropunctata Roger), red imported fire ants (Solenopsis geminata Fabricius), red imported fire ants (Solenopsis invicta Buren), and Argentine ants (Iridomyrmex humilis Other examples include the Mayr ant, the crazy ant (Paratrechina longicornis Latreille), the pavement ant (Tetramorium caespitum Linnaeus), the cornfield ant (Lasius alienus Foerster), and the Odras house ant (Tapinoma sessile Say). Bees (including the Asian giant hornet), Asian giant hornet, yellow hornet, wasp, sawtooth wasp (species of the genus Neodiprion, species of Cephus, etc.), other Hymenoptera, termites of the family Termitidae (e.g., species of Macrotermes sp., Odontotermes obesus Rambur), Kalotermitidae (e.g., species of Cryptotermes sp.), and Rhinotermitidae (e.g., species of Reticulitermes sp.).), species of the genus Coptotermes (Coptotermes sp., Heterotermes tenuis Hagen), Eastern subtarrenian termite (Reticulitermes flavipes Kollar), Western subtarrenian termite (Reticulitermes hesperus Banks), Formosan subtarrenian termite (Coptotermes formosanus Shiraki), West Indian drywood termite (Incisitermes immigrans Snyder), Powderpost termite (Cryptotermes brevis Walker's termite (Incisitermes snyderi Light), Southeastern subterranean termite (Reticulitermes virginicus Banks), West drywood termite (Incisitermes minor Hagen), for example, species of the genus Nasutitermes (Nasutitermes sp.Isopteran pests including arboritic termites, other economically important termites, silverfish (Lepisma saccharina Linnaeus) and spotted silverfish (Thermobia domestica Packard), Thysanura pests, head lice (Pediculus humanus capitis De Geer), human lice (Pediculus humanus Linnaeus), chicken lice (Menacanthus stramineus Nitzsch), dog biting louse (Trichodectes canis de Geer) This includes pests of the orders Mallophaga and Phthiraptera, such as the chicken louse (Goniocotes gallinae De Geer), sheep louse (Bovicola ovis Schrank), cattle louse (Haematopinus eurysternus Nitzsch), and cow louse (Linognathus vituli Linnaeus), as well as other blood-sucking and chewing parasitic lice that attack humans and animals. Other examples include the Oriental mouse flea (Xenopsylla cheopis Rothschild), the cat flea (Ctenocephalides felis Bouche), the dog flea (Ctenocephalides canis Curtis), the chicken flea (Ceratophyllus gallinae Schrank), the chicken flea (Echidnophaga gallinacea Westwood), the human flea (Pulex irritans Linnaeus), and other fleas (Siphonoptera) that plague mammals and birds. Additional arthropod pests that are included include 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 Scutigeromorpha, such as the house centipede Linnaeus (Scutigera coleoptrata Linnaeus).

[0297] Examples of invertebrate pests of stored grains include the long-eared grain borer (Prostephanus truncatus Horn), the small-eared grain borer (Rhyzopertha dominica Fabricius), the grain weevil (Sitophilus oryzae Linnaeus), the grain weevil (Sitophilus zeamais Motschulsky), the four-spotted bean weevil (Callosobruchus maculatus Fabricius), and the confused flour beetle (Tribolium castaneum). Examples include Herbst), the granaria weevil (Sitophilus granarius Linnaeus), the Indian meal moth (Plodia interpunctella Huebner), the striped rice meal moth (Ephestia kuehniella Zeller), and the rusty-breasted flat beetle (Cryptolestes ferrugineus Stephens).

[0298] The compounds disclosed herein include, but are not limited to, economically important agricultural pests (i.e., root-knot nematodes of the genus Meloidogyne, root-lesion nematodes of the genus Pratylenchus, and leucocephala of the genus Trichodorus), as well as animal and human health pests (i.e., common roundworm (Strongylus vulgaris) in horses, roundworm (Toxocara canis) in dogs, torsional gastric worm (Haemonchus contortus) in sheep, heartworm (Dirofilaria immitis Leidy) in dogs, tapeworm (Anoplocephala perfoliata) in horses, and liver fluke (Fasciola hepatica) in ruminants. It may be active against members of the classification Nematoda, Cestoda, Trematoda, and Acanthocephala, including economically important members of the orders Strongylida, Ascaridida, Oxyurida, Rhabditida, Spirurida, and Enopliida, such as all economically important trematodes, tapeworms, and roundworms (including Linnaeus).

[0299] The compounds disclosed herein are pests in the order Lepidoptera (e.g., Alabama argillacea Huebner (cotton leaf worm), Archips argyrospila Walker (fruit tree leaf roller), A. rosana Linnaeus (European leaf roller) and other species of the genus Archips, Chilo suppressalis Walker (rice stem borer), Cnaphalocrocis medinalis Guenee (rice leaf florer), Crambus caliginosellus Clemens (corn root web worm), Crambus teterrellus Zincken (bluegrass web worm), Cydia pomonella) Linnaeus (Codling Moth), Earias insulana Boisduval (Three-striped Codling Moth), Earias vittella Fabricius (Grass-banded Codling Moth), Helicoverpa armigera Huebner (Tobacco Bud Moth), Helicoverpa zea Boddie (American Tobacco Bud Moth), Heliothis virescens Fabricius (False American Tobacco Bud Moth), Herpetogramma licarsisalis Walker (Black-banded Black Moth), Lobesia botrana Denis & Schiffermueller (Narrow-winged Leafroller Moth), Pectinophora gossypiella Saunders (Cotton Earworm), Phyllocnistis citrella Stainton (Citrus Leafminer), Pieris brassicaeIt may be active against *Pieris linnaeus* (large white butterfly), *Pieris rapae Linnaeus* (cabbage white butterfly), *Plutella xylostella Linnaeus* (diamondback moth), *Spodoptera exigua Huebner* (white-spotted armyworm), *Spodoptera litura Fabricius* (beet armyworm), *Spodoptera frugiperda JESmith* (white-spotted armyworm), *Trichoplusia ni Huebner* (nettle moth), and *Tuta absoluta Meyrick* (tomato leafworm).

[0300] The compounds disclosed herein include Acyrthosiphon pisum Harris (pea aphid), Aphis craccivora Koch (bean aphid), Aphis fabae Scopoli (bean black aphid), Aphis gossypii Glover (cotton aphid, melon aphid), Aphis pomi De Geer (apple aphid), Aphis spiraecola Patch (spirea aphid), and Aulacorthum solani Kaltenbach (potato aphid), Chaetosiphon fragaefolii Cockerell (strawberry aphid), Diuraphis noxia Kurdjumov / Mordvilko (Russian strawberry aphid), Dysaphis plantaginea Passerini (pink apple aphid), Eriosoma lanigerum Hausmann (apple aphid), Hyalopterus pruni Geoffroy (peach aphid), Lipaphis pseudobrassicae Davis Davis (false radish aphid), Metopolophium dirrhodum Walker (wheat aphid), Macrosiphum euphorbiae Thomas (potato aphid), Myzus persicaeSulzer (peach aphid, green peach aphid), Nasonovia ribisnigri Mosley (lettuce aphid), species of Pemphigus (root aphid and gall aphid), Rhopalosiphum maidis Fitch (corn aphid), Rhopalosiphum padi Linnaeus (wheat aphid), Schizaphis graminum Rondani (wheat aphid), Sitobion avenae Fabricius (English grain aphid), Therioaphis maculata Buckton (alfalfa aphid), Toxoptera aurantii Boyer de Fonscolombe (citrus aphid) and Toxoptera citricidus Kirkaldy (brown citrus aphid), species of the genus Adelges (citrus aphid), Phylloxera devastatrix Pergande (pecan phylloxera), Bemisia tabaci Gennadius (tobacco whitefly, sweet potato whitefly), Bemisia argentifolii Bellows & Perring (silverleaf whitefly), Dialeurodes citri Ashmead (citrus whitefly), and Trialeurodes vaporariorum Westwood (greenhouse whitefly), Empoasca fabae HarrisHarris (potato leafhopper), Laodelphax striatellus Fallen (smaller brown plant hopper), Macrosteles quadrilineatus Forbes (aster leaf hopper), Nephotettix cincticeps Uhler (green rice leaf hopper), Nephotettix nigropictus Stal (rice leaf hopper), Nilaparvata lugens Stal (brown plant hopper), Peregrinus maidis Ashmead (corn plant hopper), Sogatella furcifera Horvath (white-backed planthopper), Tagosodes orizicolus Muir (rice delfaciid), Typhlocyba pomaria McAtee (white apple leaf hopper), species of Erythroneura (grape leaf hopper), Magicidada septendecim Linnaeus (periodical cicada), Icerya purchasi Maskell (Icerya scale insect), Quadraspidiotus perniciosus Comstock (Sanjos scale insect), Planococcus citri Risso (citrus mealybug), species of the genus Pseudococcus (a group of other mealybugs), Cacopsylla pyricolaIt exhibits remarkable activity against Hemiptera animals such as Foerster (psyllid) and Trioza diospyri Ashmead (persimmonpusilla).

[0301] The compounds disclosed herein include Acrosternum hilare Say (green stink bug), Anasa tristis De Geer (sea bug), Blissus leucopterus leucopterus Say (American stink bug), Cimex lectularius Linnaeus (bed bug), Corythucha gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), and Dysdercus suturellus Herrich-Schaeffer (cotton stink bug), Euschistus servus Say (brown stink bug), Euschistus variolarius Palisot de Beauvois (one-spotted stink bug), Graptostethus species (a group of seed bugs), Halyomorpha halys Stael (brown stink bug), Leptoglossus corculus Say (leaf-footed pine seed bug), Lygus lineolaris Palisot de Beauvois (green blind turtle), Nezara viridula linnae Viridula Linnaeus (Southern Green Stink Bug), Oebalus pugnax Fabricius (Rice Stink Bug), Oncopeltus fasciatus Dallas (Large Milkweed Bug), Pseudatomoscelis ceriatus lauterIt also exhibits activity against members derived from the order Hemiptera, such as *Seriatus Reuter* (Cotton Free Hopper). Other insect orders controlled by the compounds disclosed herein include Thysanoptera (e.g., Frankliniella occidentalis Pergande (citrus thrips), Scirtothrips citri (citrus thrips), Scirtothrips variabilis Beach (soybean thrips), and Thrips tabaci Lindeman (onion thrips)) and Coleoptera (e.g., Leptinotarsa ​​decemlineata Say (colored beetle), Epilachna varivestis Examples include the mulligan (Ladybug) and wireworms belonging to the genera Agriotes, Athous, or Limonius.

[0302] Of particular note is the use of the compounds of this disclosure for the control and eradication of the citrus thrips (Frankliniella occidentalis). Of particular note is the use of the compounds of this disclosure for the control and eradication of the potato leafhopper (Empoasca fabae). Of particular note is the use of the compounds of this disclosure for the control and eradication of the cotton aphid (Aphis gossypii). Of particular note is the use of the compounds of this disclosure for the control and eradication of the peach aphid (Myzus persicae). Of particular note is the use of the compounds of this disclosure for the control and eradication of the tobacco whitefly (Bemisia tabaci).

[0303] The compounds of this disclosure may also be useful for increasing the vitality of crop plants. The method involves contacting a crop plant (e.g., leaves, flowers, fruits, or roots) or a seed on which the crop plant is growing with a compound of Formula 1 in an amount sufficient to achieve the desired plant vitality effect (i.e., a biologically effective amount). Typically, the compound of Formula 1 is applied in a formulated composition. The compound of Formula 1 is often applied directly to the crop plant or its seeds, but it can also be applied to the location of the crop plant, i.e., the environment of the crop plant, in particular to a part of the environment that is close enough for the compound of Formula 1 to reach the crop plant. The location relevant to this method most commonly includes the growth medium in which the plant is cultivated (i.e., the medium that supplies nutrients to the plant), typically soil. Thus, treatment of crop plants to increase their vitality involves contacting the crop plant, the seed on which the crop plant is growing, or the location of the crop plant with a biologically effective amount of the compound of Formula 1.

[0304] Increased crop vitality 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 uprightness; (b) enhanced crop growth, as indicated by rapid and robust leaf growth (e.g., measured by leaf area index), plant height, number of tillers (e.g., in the case of rice), root mass and total dry weight of crop vegetative growth; (c) improved crop yield, as indicated by time to flowering, flowering period, number of flowers, total biomass accumulation (i.e., yield) and / or marketability of the fruit or grain grade of the produce (i.e., yield quality); (d) enhanced ability of crops to withstand or prevent infection by plant diseases and the spread of arthropod, nematode or mollusk pests; and (e) increased ability of crops to withstand environmental stresses such as exposure to extreme temperatures, suboptimal moisture or phytotoxic chemicals.

[0305] The compounds of this disclosure may increase the vitality of treated plants compared to untreated plants by killing or preventing the consumption of herbivorous invertebrate pests in the plant environment. In the absence of control of such herbivorous invertebrate pests, the pests reduce the vitality of plants by consuming plant tissue or sap, or by transmitting plant pathogens such as viruses. Even in the absence of herbivorous invertebrate pests, the compounds of this disclosure may increase the vitality of plants by altering their metabolism. In general, the vitality of crop plants will be most significantly increased by treating them with the compounds of this disclosure when the plants are grown in a non-ideal environment, i.e., an environment that includes one or more aspects that are unfavorable to the plants in achieving the full genetic potential that the plants would exhibit in an ideal environment.

[0306] Of particular note is the method for increasing the vitality of crop plants growing in environments containing herbivorous invertebrate pests. Also noteworthy is the method for increasing the vitality of crop plants growing in environments free from herbivorous invertebrate pests. Furthermore, it is noteworthy for increasing the vitality of crop plants growing in environments with less water than ideal for supporting their growth. Of particular note is the method for increasing the vitality of crop plants, specifically rice. Of particular note is the method for increasing the vitality of crop plants, specifically corn. Of particular note is the method for increasing the vitality of crop plants, specifically soybeans.

[0307] The compounds of this disclosure may also be mixed with one or more other bioactive compounds or agents, including insecticides, fungicides, nematicides, fungicides, acaricides, herbicides, herbicide toxicity reducers, growth regulators, such as insect molting inhibitors and rooting promoters, chemical hemostatic agents, semi-chemicals, repellents, attractants, pheromones, feeding stimulants, other bioactive compounds, or entomopathogenic bacteria, viruses, or fungi, to form multi-component insecticides that give an even broader spectrum of agrochemical and non-agrochemical applications. Accordingly, this disclosure also relates to compositions comprising a bioactive amount of the compound of Formula 1, at least one further component selected from the group consisting of surfactants, solid diluents, and liquid diluents, and at least one further bioactive compound or agent. With respect to the mixtures of this disclosure, other bioactive compounds or agents can be combined with the compounds of the present invention containing the compound of Formula 1 to form a premix, or other bioactive compounds or agents can be combined separately from the compounds of the present invention containing the compound of Formula 1, and the two formulations can be combined together before application (for example, in a spray tank) or applied sequentially instead.

[0308] Examples of such bioactive compounds or agents that can be formulated with the compounds of this disclosure include abamectin, acephate, acequinosyl, acetamiprid, acrinatrin, afidopiropene ([(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a ,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methylcyclopropanecarboxylate), amidoflumet, amitraz, avermectin, azadirachtin, azinphosmethyl, benfuracarb, bensultap, bifenthrin, bifenazate, bistriflurone, borate, buprofezin, kazusaphos, carbaryl, ca Lubofuran, Cartap, Calzol, Chlorantraniliprole, Chlorfenapyr, Chlorfluazuron, Chlorpyrifos, Chlorpyrifos Methyl, Chromafenozide, Clofentezin, Clothianidin, Cyantraniliprole (3-Bromo-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-1H-pyrazole-5-carboxamide), Cycla Niliprole (3-bromo-N-[2-bromo-4-chloro-6-[[(1-cyclopropylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide), cycloprothrin, cycloxapride ((5S,8R)-1-[(6-chloro-3-pyridinyl)methyl]-2,3,5,6,7,8-hexahydro-9-nitro-5,8-epoxy-1H-imidazo[1,2-a) Azepine), Cyflumetofen, Cyfluthrin, β-Cyfluthrin, Cyhalothrin, γ-Cyhalothrin, λ-Cyhalothrin, Cypermethrin, α-Cypermethrin, -Cypermethrin, Cyromazine, Deltamethrin, Diafenthiuron, Diazinon, Dierdrin, Diflubenzuron, Dimefluthrin, Dimehypo, Dimethoate, Dinotefuran, Diophenolane, Emamectin, Endosulfan, Esfenvalerate, Ethiprol, Etofenprox, Ethoxazole, Fenbutane oxide fenitrothion, Phenothioca Lube, phenoxycarb, fenpropathrin, fenvalerate, fipronil, flomethkin (2-ethyl-3,7-dimethyl-6-[4-(trifluoromethoxy)phenoxy]-4-quinolinylmethyl carbonate), flonicamide, flubendiamide, flucitrinate, flufenelim, flufenoxuron, flufenoxystrobin (methyl(αE)-2-[[2-chloro-4-(trifluoromethyl)phenoxy]methyl]-α-(methoxymethylene)benzeneacetate), flufensulfon (5-chloro-2-[(3,4, 4-Trifluoro-3-buten-1-yl)sulfonyl]thiazole), fluhexaphon, fluopyram, flupiprole (1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(2-methyl-2-propen-1-yl)amino]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitride), flupyradiflon (4-[[(6-chloro-3-pyridinyl)methyl](2,2-difluoroethyl)amino]-2(5H)-furanone), fluvalinate, tau-fluvalinate, phonophos, f Formethaneate, fothiazate, halophenozide, heptafluthrin ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl2,2-dimethyl-3-[(1Z)-3,3,3-trifluoro-1-propen-1-yl]cyclopropanecarboxylate), hexythiazox, hydramethylnon, imidacloprid, indoxacarb, insecticide 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, Methoxyphenozide, Metofluthrin, Monoclotophos, Monofluorothrin ([2,3,5,6-Tetrafluoro-4-(methoxymethyl)phenyl]methyl 3-(2-cyano-1-propen-1-yl)-2,2-dimethylcyclopropanecarboxylate), Nicotin, Nitenpyram, Nichiazine, Novalon, Noviflumuron, Oxamyl, Parathion, Parathion Methyl, Permethrin, Phorate, Fosalon, Fosmet, Phosphamidone, Pyrimicalb, Profenophos, Profluthrin, Propargit, Protrifenbut, Piflubumido(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, pyrethrin, pyridaben, pyridaryl, pyrifluquinazone, pyriminostrobin (methyl(αE)-2-[[[2-[(2,4-dichlorophenyl)amino]-6-( [Pyromidine (Pyromidine)-4-Oxymethyl]-α-(Methoxymethylene)benzeneacetate, Pyriprole, Pyriproxyfen, Rotenone, Ryanodine, Silafluofen, Spinetoram, Spinosad, Spirodiclofen, Spiromesifen, Spirotetramato, Sulprophos, Sulfoxaflor (N-[Methyloxide[1-[6-(Trifluoromethyl)-3-Pyrimidine]ethyl]-λ, 4[Sulfanylidene]cyanamide), tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, terbuphos, tetrachlorvinphos, tetramethrin, tetramethylfluthrin ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl 2,2,3,3-tetramethylcyclopropanecarboxylate), tetraniliprol, thiacloprid, thiamethoxam, thiodicarb, thiosultap Examples include sodium, thioxazafen (3-phenyl-5-(2-thienyl)-1,2,4-oxadiazole), tolfenpyrad, tralomethrin, triazamate, trichlorfone, triflumezopyrim (2,4-dioxo-1-(5-pyrimidinylmethyl)-3-[3-(trifluoromethyl)phenyl]-2H-pyrido[1,2-a]pyrimidinium internal salt), triflumulone, Bacillus thuringiensis delta-endotoxin, insecticides, entomopathogenic bacteria, entomopathogenic viruses, and entomopathogenic fungi.

[0309] Of particular note are abamectin, acetamiprid, acrinatrin, afidopiropene, amitraz, avermectin, azadirachtin, benfuracarb, bensultap, bifenthrin, buprofezin, kazusafos, carbaryl, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin, cyfluthrin, β-cyfluthrin, cyhalothrin, γ-cyhalothrin, λ-cyhalotrin, cypermethrin, α-cypermethrin, ζ-cypermethrin, cyromazine, deltamethrin, dierdrin, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenitrothion, phenothiocarb, phenoxycarb, fenvalerate, fipronil, flometoquin, flonicamide, flubendiamide, flufenoxuron, flufenoxystrobi Flufensulfon, Flupiprol, Flupyradiflon, Fluvalinate, Formetanate, Fostiazate, Heptafluthrin, Hexaflumurone, Hydramethylnon, Imidaclopride, Indoxacarb, Lufenulon, Meperfluthrin, Metaflumizone, Methiodicarb, Methomyl, Methoprene, Methoxyphenozide, Metofluthrin, Monofluorothrin, Nitenpyram, Nichiazine, Novalon, Oxamyl, Piflubumi, Pymetrozine, Pyreth These are insecticides containing phosphorus, pyridaben, pyridaryl, pyriminostrobin, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulfoxaflor, tebufenozide, tetramethrin, tetramethylfluthrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, triflumezopyrim, triflumulon, Bacillus thuringiensis delta-endotoxin, all strains of Bacillus thuringiensis, and all strains of nucleopolyhedrosis virus.

[0310] One embodiment of a biological agent for mixing with the compounds of this disclosure includes entomopathogenic bacteria, e.g., 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, and the United States), entomopathogenic fungi, e.g., green muscardine fungus, and entomopathogenic viruses (both naturally occurring and genetically modified), e.g., baclovirus, nucleopolyhedovirus (NPV), e.g., Helicoverpa zea nucleopolyhedovirus (HzNPV), Anagrapha falcifera Examples include falcifera nucleopolysludge virus (AfNPV) and granuloma virus (GV), such as codlinga (Cydia pomonella) granuloma virus (CpGV).

[0311] One embodiment of a biological agent for mixing with the compounds of the present disclosure is (i) Actinomycetes, Agrobacterium, Arthrobacter, Alcaligenes, Aureobacterium, Azobacter, Bacillus, Beijerinckia, and Bradyrhizobium Genus Bradyrhizobium, Brevibacillus, Burkholderia, Chromobacterium, Clostridium, Clavibacter, Comamonas, Corynebacterium, Curtobacterium, Enterobacter Flavobacterium, Gluconobacter, Hydrogenophaga, Klebsiella, Methylobacterium, Paenibacillus, Pasteuria, Photorhabdus, Phyllobacterium Bacteria of the genera Bacillus, Pseudomonas, Rhizobium, Serratia, Sphingobacterium, Stenotrophomonas, Streptomyces, Variovorax, or Xenorhabdus, such as Bacillus amyloliquefaciens, Bacillus cereus, Bacillus firmus, Bacillus licheniformis (Bacillus,Bacillus licheniformis, Bacillus pumilus, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Bradyrhizobium japonicum, Chromobacterium subtsugae, Pasteuria nishizawae, Pasteuria penetrans, Pasteuria usage, Pseudomonas fluorescens, and Streptomyces rigis (ii) bacteria of Lydicus, (ii) fungi, e.g., Green's Mascardine, (iii) baculoviruses, nuclear polyhedron disease viruses, e.g., tobacco budworm (Helicoverpa zea) nuclear polyhedron disease virus, Anagrapha falcifera nuclear polyhedron disease virus, granuloma viruses, e.g., codling moth (Cydia pomonella) granuloma virus, one or a combination of these viruses.

[0312] Of particular note are combinations in which other invertebrate pest control active ingredients belong to different chemical classifications or have different sites of action from the compound of Formula 1. In certain examples, combinations with at least one other invertebrate pest control active ingredient having a similar control spectrum but a different site of action are particularly advantageous for resistance management. Therefore, the compositions of the present disclosure may further contain a bioeffective amount of at least one further invertebrate pest control active ingredient having a similar control spectrum but belonging to a different chemical classification or having a different site of action. These additional bioactive compounds or agents include, but are not limited to, acetylcholinesterase (AChE) inhibitors such as the carbamates methomyl, oxamyl, thiodicarb, and triazamates, and the organophosphate chlorpyrifos; GABA-gate chloride channel antagonists such as the cyclodienes dierdrin and endosulfan, and the phenylpyrazoles ethiprole and fipronil; sodium channel modulators such as the pyrethroids bifenthrin, cyfluthrin, β-cyfluthrin, cyhalothrin, λ-cyhalothrin, cypermethrin, δ-methrin, dimefluthrin, esfenvalerate, metofluthrin, and profluthrin; and neonicotinoids such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, and nichiad. Nicotinic acetylcholine receptor (nAChR) agonists such as thiacloprid, thiamethoxam, sulfoximine sulfoxaflor, butenolide flupyradiflon, mesoionic triflumesopyrim, etc. Nicotinic acetylcholine receptor (nAChR) allosteric activators such as spinosin derivatives spinetram and spinosad, chloride channel activators such as abamectin and emamectin, juvenile hormone mimetic agents such as diofenolan, methoprene, phenoxycarb, pyriproxyfen, chord organ regulators such as pymetrozine, pyrifluquinazon, flonicamide, mite growth inhibitors such as etoxazole, mitochondrial ATP synthase inhibitors such as propargit, and inhibitors of oxidative phosphorylation by disruption of the proton gradient such as chlorfenapyr.For example, nicotinic acetylcholine receptor (nAChR) channel blockers such as the nereitoxin analog Cartap; chitin biosynthesis inhibitors such as the benzoylurea-based flufenoxurone, hexaflumurone, lufenuron, novaron, nobiflumulone, triflumulone, and buprofezin; diptera molting inhibitors such as cyromazine; ecdysone receptor agonists such as diacylhydrazine 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; and voltage-dependent inhibitors such as indoxacarb. Medicinal sodium channel blockers, such as acetyl-CoA carboxylase inhibitors like tetronic acid and tetramic acid spirodiclofen, spiromesifen and spirotetramato, mitochondrial complex II electron transport inhibitors such as β-ketonitrile cyenopyrafen and β-ketonitrile cyflumetofen, ryanodine receptor modulators such as anthranildiamide-based chlorantraniliprole and cyantraniliprole, diamides such as flubendiamide and ryanodine receptor ligands such as ryanodine, compounds whose biologically active target sites are unknown or undetermined, such as azadirachtin and pyridaryl, and biological agents including microorganisms that disrupt the midgut membrane of insects such as Bacillus thuringiensis and the δ-endotoxin they produce, and Bacillus sphaericus, as well as nuclear polyhedrosis (NPV) and other naturally occurring or genetically modified insecticidal viruses.

[0313] Further examples of bioactive compounds or agents that can be formulated with the compounds of this disclosure include: acibenzoral-S-methyl, algimorph, amethotrazine, aminopyriphen, amisulbrom, anilazine, azaconazole, azoxystrobin, venalaxyl (including venalaxyl-M), benodanil, benomyl, bentheavalicarb (including bentheavalicarb-isopropyl), benzovindiflupyr, betoxazine, binapacril, biphenyl, bitertanol, bixafen, blasticidine-S, boscalid, bromuconazole Butyrimate, Butthiobate, Carboxyne, Carpropamide, Captafo, Captan, Carbendazim, Chloromb, Chlorthalonil, Clozolinate, Copper hydroxide, Copper oxychloride, Copper sulfate, Cuxistrobin, Cyazofamide, Cyflufenamid, Cymoxanil, Cyproconazole, Cyprodinil, Diclobentiazox, Diclofluanide, Diclosimet, Diclomazine, Dichloran, Dietofencarb, Difenoconazole, Diflumetrim, Dimethylimol, Dimethomorph, Dimoxystrobin, Diniconazole (Diniconor -M included), Dinocap, Dipimethitrone, Dithianone, Dithiolan, Dodemorph, Dozin, Econazole, Etaconazole, Edifenfos, Enoxastrobin (also known as Enestrogen), Epoxyconazole, Etaboxam, Ethilimol, Etridiazole, Famoxadone, Phenamidone, Phenamistrobin, Phenimarimol, Fenbuconazole, Fenflam, Fenhexamide, Phenoxanil, Fenpiclonil, Fenpicoxamide, Fenpropidine, Fenpropimorph, Fenpiraz Min, fentin acetate, fentin hydroxide, felbam, ferimzon, flomethkin, floryl picoxamide, fluopimamide, fluazinam, fludioxonil, fluphenoxystrobin, fluindapir, flumorph, fluopicolid, fluopyram, fluoxapiproline, fluoxastrobin, flukonocinazole, flusilazole, flusulfamide, fluthianil, flutolanil, flutriafole, fluxapiroxad, forpet, phthalide (also known as phthalide), fuberidazole, flamethaxyl, flamethaxyl,Flupiraxil, hexaconazole, himexazole, guazatine, imazalil, imibenconazole, iminoctadine albesilate, iminoctadine triacetate, impulfluxam, iodicarb, ipconazole, ipfentrifluconazole, ipflufenoquine, isofetamide, iprobenphos, iprodione, iprovalicarb, isoflucipram, isoprothiolane, isopyrazam, isothianil, kasugamycin, kresoximmethyl, lancotrione, mancozeb, mandipropamide, mandestolbine, maneb, mapani Pyrene, mefentrifluconazole, mepronil, meptildinocap, metalaxyl (including metalaxyl-M / mephenoxam), metconazole, metasulfocarb, methylam, metminostrobin, methyltetraprole, metraphenone, mycrobutanil, naphthitine, neo-asodine (ferric methanesulfonate), nualimol, octylinone, oflace, orysastrobin, oxadixyl, oxatiapiproline, oxolinic acid, oxoconazole, oxycarboxyne, oxytetracycline, penconazole, pencyclon Penflufen, penthiopyrad, perfurazoate, phosphite (including its salts, e.g., focetyl-aluminum), picoxystrobin, piperalin, polyoxin, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, proquinazide, prothiocarb, prothioconazole, prothioconazole, piriflumetofen (Adepidyn®), pyraclostrobin, pyrametostrobin, pyrapropoin, pyraoxystrobin, pyraziflumid, pyrazofos, pyribencarb, pyrib Tacarb, pyridaclomethyl, pyrifenox, pyrifenone, perisoxazole, pyrimethanil, pyrifenox, pyrrolnitrin, pyroquilon, quinconazole, quinmethionate, quinofumerine, quinoxyfen, quintozen, silthiofame, sedaxane, simeconazole, spiroxamine, streptomycin, sulfur, tebuconazole, tebufloxin, tecrophthalam, tecrophthalam, technazen, terbinafine, tetraconazole, thiabendazole, tifluzamide, thiophanate, thiophanate-methyl, thyram, thiadinyl,Fungicides such as tolclophosmethyl, tolprocarb, trifluanide, triadimefon, triadimenol, triarimol, triazoxide, tribasic copper sulfate, triclopyricarb, tridemorph, trifloxystrobin, triflumizole, trimopramide, tricyclazole, trifloxystrobin, triforine, triconazole, uniconazole, validamycin, valifenarate (also known as valifenal), vinclozoline, zineb, ziram, zoxamide, and fungicides such as 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]etanone, fluopyram, spirotetramate , thiodicarb, fostiazate, abamectin, iprodione, fluensulfone, dimethyl disulfide, thioxazafen, 1,3-dichloropropene (1,3-D), metam (sodium and potassium), dazomet, chloropicrin, phenamifos, etoprofos, kazusafos, terbufos, imisiafos, oxamyl, carbofuran, thioxazafen, nematicides such as Bacillus firmus and Pasturia nisizawae, fungicides such as streptomycin, acaricides such as amitraz, chinomethionate, chlorobenzylate, cyhexatine, dicol, dienochlor, etoxazole, phenazaquin, fenbutane oxide, fenpropathrin, fenpyroximate, hexithiazox, propargit, pyridaben, and tebufenpyrad.

[0314] Invertebrate pests are controlled in agricultural and non-agricultural uses by directly applying one or more of the compounds of this disclosure, typically in compositional form, in biologically effective amounts, to pest environments, protected areas, or pests to be controlled, including agricultural and / or non-agricultural infestation sites.

[0315] Therefore, the present disclosure includes methods for controlling and eradicating invertebrate pests in agricultural and / or non-agricultural uses, comprising contacting the invertebrate pest or its environment with a composition comprising one or more or at least one such compound of the present disclosure in a biologically effective amount, or a composition comprising at least one such compound and at least one further biologically active compound or agent in a biologically effective amount. Examples of suitable compositions comprising the compounds of the present disclosure and at least one further biologically active compound or agent in a biologically effective amount include granular compositions in which the additional active compound is present on the same granules as the compounds of the present disclosure or on granules separate from those of the compounds of the present disclosure.

[0316] To achieve contact with the compounds or compositions of this disclosure for the protection of crops from invertebrate pests, the compounds or compositions are typically applied to crop seeds before planting, to the stems and leaves of crop plants (e.g., leaves, stems, flowers, fruits), or to the soil or other growth medium before or after planting the crop.

[0317] One embodiment of the contact method is by spraying. In addition, granular compositions containing the compounds of the Disclosure may be applied to the stems and leaves of plants or to the soil. The compounds of the Disclosure can also be effectively delivered by plant ingestion by contacting plants with compositions containing the compounds of the Disclosure, which are applied as soil infusions of liquid formulations, granular formulations applied to soil, seedling box treatments, or immersion of transplants. Of particular note is the composition of the Disclosure in the form of a soil infusion liquid formulation. Also of note is a method for controlling and eradicating invertebrate pests, which involves contacting the invertebrate pests or their environment with a biologically effective amount of the compound of the Disclosure or a composition containing a biologically effective amount of the compound of the Disclosure. Further of note is this method in which the environment is soil and the composition is applied to the soil as a soil infusion formulation. Furthermore of note is that the compounds of the Disclosure are also effective by local application to the site of infestation. Other methods of contact include direct and residual spraying, aerial spraying, gel, seed coating, microencapsulation, infiltration, bait, ear tag, bolus, sprayer, fumigator, aerosol, dust, and many others. One embodiment of a contact method is a dimensionally stable fertilizer granule, stick, or tablet containing the compound or composition of the disclosure. The compounds of the disclosure can also be impregnated into materials for the components of invertebrate control devices (e.g., insect nets).

[0318] The compounds disclosed herein are useful for treating all plants, plant parts, and seeds. Plant and seed varieties and cultivars can be obtained by conventional propagation and breeding methods or by genetic engineering methods. A genetically modified plant or seed (genetically modified plant or seed) is one in which a different gene (transgene) is stably incorporated into the genome of the plant or seed. A transgene defined by its specific location within the plant genome is called a transformation or transgenic event.

[0319] Examples of genetically modified plant and seed cultivars that can be processed in accordance with this disclosure include those that are resistant to one or more biological stresses (such as nematodes, insects, mites, and fungi) or abiotic stresses (such as drought, low temperatures, and soil salinity), or that possess other desirable traits. Plants and seeds can be genetically modified to exhibit traits such as herbicide resistance, insect resistance, modified oil profiles, 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 on the genetic modifications listed in Table Z can be obtained from the following databases: OECD BioTrack Product Database [Database Online]. From the Organisation for Economic Co-operation and Development (OECD) via the Internet.<https: / / biotrackproductdatabase.oecd.org / byidentifier.aspx> It was obtained using [this method]. USDA Animal and Plant Health Inspection Service [Online Database]. Internet<http: / / www.aphis.usda.gov> Obtained from the US Department of Agriculture using [this method]. Deliberate Release and Placing on the EU Market of GMOs - GMO Register [Database Online]. Internet<http: / / gmoinfo.jrc.ec.europa.eu> Obtained from the European Commission Joint Research Centre using [source / method].

[0320] In Table Z below, the following abbreviations are used: tol. stands for resistance, res. stands for resistance, SU stands for sulfonylurea, ALS stands for acetolactate synthase, HPPD stands for 4-hydroxyphenylpyruvate dioxygenase, and NA stands for not applicable.

[0321] [Table 40]

[0322] [Table 41]

[0323] [Table 42]

[0324] [Table 43]

[0325] [Table 44]

[0326] [Table 45]

[0327] [Table 46]

[0328] [Table 47]

[0329] [Table 48]

[0330] [Table 49]

[0331] [Table 50]

[0332] [Table 51]

[0333] [Table 52]

[0334] [Table 53]

[0335] Enhanced effects can be obtained by treating genetically modified plants and seeds with the compounds of this disclosure. For example, reductions in application rates, expansion of the activity spectrum, increased resistance to biological / biological stress, or enhanced storage stability may be greater than those expected from the simple additive effects of applying the compounds of this disclosure to genetically modified plants and seeds.

[0336] The compounds of this disclosure are also useful for seed treatment to protect seeds from invertebrate pests. With respect to this disclosure and claims, seed treatment means contacting seeds with a bioeffective amount of the compounds of this disclosure, typically formulated as a composition of this disclosure. This seed treatment protects seeds from invertebrate soil pests and can also protect the roots and other plant parts that come into contact with the soil of seedlings that develop from germinated seeds. Seed treatment can also achieve foliage protection through the translocation of the compounds of this disclosure or a second active ingredient within developing plants. Seed treatment can be applied to all types of seeds, including seeds from which genetically transformed plants expressing specific traits will germinate. Typical examples include those expressing proteins toxic to invertebrate pests, such as Bacillus thuringiensis toxin, or those expressing herbicide resistance, such as glyphosate acetyltransferase, which confers resistance to glyphosate. Seed treatment with the compounds of this disclosure can also increase the vitality of plants growing from treated seeds.

[0337] One method of seed treatment involves spraying or dusting the seeds with the compounds of the present disclosure (i.e., as a formulated composition) before sowing. Formulated compositions for seed treatment generally include a film-forming agent or adhesive. Therefore, typically, the seed coating compositions of the present disclosure include a biologically effective amount of the compound of Formula 1, its N-oxide or salt, and a film-forming agent or adhesive. Seeds can be coated by spraying a fluid suspension concentrate directly onto a seed tumbling bed and then drying the seeds. Other formulation types, such as wet powders, solutions, suspension emulsions, emulsified concentrates, and aqueous emulsions, can also be sprayed onto the seeds. This process is particularly useful for applying a film coating to seeds. Various coating machines and processes are available to those skilled in the art. Preferred processes include those listed in P. Kosters et al., Seed Treatment: Progress and Prospects, 1994 BCPC Mongraph No. 57 and the references listed therein.

[0338] The compounds of Formula 1 and their compositions are particularly useful, both alone and in combination with other insecticides and fungicides, for seed treatment of crops including, but not limited to, corn or maize, soybeans, cotton, grains (e.g., wheat, oats, barley, rye, and rice), potatoes, vegetables, and rapeseed.

[0339] Other insecticides that can be combined with the compound of Formula 1 to provide a mixture useful for seed treatment include abamectin, acetamiprid, acrinatrin, amitraz, avermectin, azadirachtin, bensultap, bifenthrin, buprofezin, carbaryl, carbofuran, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyfluthrin, β-cyfluthrin, cyhalothrin, γ-cyhalothrin, λ-cyhalothrin, cypermethrin, α-cypermethrin, ζ-cypermethrin, cyromazine, deltamethrin, dierdrin, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, phenothiocarb, phenoxycarb, and fenba Lelate, fipronil, flonicamide, flubendiamide, flufenoxuron, fluvalinate, formetanate, fostiazate, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, lufenulon, metaflumizone, methiocarb, methomyl, methoprene, methoxyfenozide, nitenpyram, nithiazine, novaron, oxamyl, pymetrozine, pyrethrin, pyridaben, pyridaryl, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulfoxaflor, tebufenozide, tetramethrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazate, triflumulon, Bacillus thuringiensis This includes all strains of Bacillus thuringiensis (delta endotoxin) and all strains of nuclear polyhedrosis virus.

[0340] Examples of fungicides that, when combined with the compound of Formula 1, can provide a mixture useful for seed treatment include amisulbrom, azoxystrobin, boscalid, carbendazim, carboxyne, cymoxanil, cyproconazole, difenoconazole, dimethomorph, fluazinam, fludioxonil, fluquinconazole, fluopicolide, fluoxastrobin, flutriafoll, fluxapyroxad, ipconazole, iprodione, metalaxyl, mefenoxam, metconazole, mycrobutanil, paclobutrazol, penflufen, picoxystrobin, prothioconazole, pyraclostrobin, sedaxane, silthiofamm, tebuconazole, thiabendazole, thiophanate-methyl, thyram, trifloxystrobin, and triticonazole.

[0341] A composition 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 inoculum / extension, isoflavonoids, and lipo-chitooligosaccharides.

[0342] The treated seeds typically contain the compounds of this disclosure in an amount of about 0.1 g to 1 kg per 100 kg of seeds (i.e., about 0.0001 to 1 wt% of the untreated seeds). The fluid suspension formulated for seed treatment typically contains about 0.5 to about 70% active ingredients, about 0.5 to about 30% film-forming adhesives, about 0.5 to about 20% dispersants, 0 to about 5% thickeners, 0 to about 5% pigments and / or dyes, 0 to about 2% defoamers, 0 to about 1% preservatives, and 0 to about 75% volatile liquid diluents.

[0343] The compounds of this disclosure may be consumed by invertebrate pests or incorporated into bait compositions used in devices such as traps and bait stations. Such bait compositions may be in the form of granules comprising (a) an active ingredient, i.e., a biologically effective amount of a compound of formula 1, its N-oxide or salt, (b) one or more food materials, optionally (c) an attractant, optionally (d) one or more humectants. Of particular note are granules or bait compositions comprising 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 eradicating soil invertebrate pests at very low application doses, particularly at doses of the active ingredient that are lethal by ingestion rather than by direct contact. Some food materials can function as both food sources and attractants. 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 fruit or plant extracts, fragrances or flavorings such as other animal or plant components, pheromones, or other agents known to attract target invertebrate pests. Examples of humectants, i.e., water-retaining agents, include glycols and other polyols, glycerin, and sorbitol. Of particular note are bait compositions (and methods utilizing such bait compositions) used to control and exterminate at least one invertebrate pest selected from the group consisting of ants, termites, and cockroaches. A device for controlling and exterminating invertebrate pests may include the bait composition and a housing configured to contain the bait composition, the housing having at least one opening sized to allow the invertebrate pest to pass through, thereby allowing the invertebrate pest to access the bait composition from a location outside the housing, and the housing is further configured to be located at or near a location of potential or known activity of the invertebrate pest.

[0344] The compounds of this disclosure may be applied without other auxiliaries, but in most cases, application is the application of a formulation containing one or more active ingredients, together with a suitable carrier, diluent and surfactant, and optionally in combination with food depending on the intended end use. One method of application involves spraying an aqueous dispersion or refined oil solution of the compounds of this disclosure. Combinations with spray oils, spray oil concentrates, spreading agents, auxiliaries, other solvents and piperonyl butoxide often enhance the efficacy of the compounds. For non-agricultural use, such spraying may be applied from a spray container such as a can, bottle or other container by discharging from a pump or pressurized vessel, such as a pressurized aerosol spray can. Such spray compositions can take various forms, such as spray, mist, foam, fume or mist. Thus, such spray compositions may optionally further include propellants, foaming agents, etc. Of particular note are spray compositions comprising a bioavailable amount of the compounds or compositions and carriers of this disclosure. One embodiment of such a spray composition comprises a bioavailable amount of the compounds or compositions and propellants of this disclosure. Typical 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 particular note are spray compositions (and methods utilizing such spray compositions dispensed from a spray container) used individually or in combination to control and exterminate at least one invertebrate pest selected from the group consisting of mosquitoes, gnats, stable flies, horseflies, wasps, yellowjackets, hornets, ticks, spiders, ants, and black flies.

[0345] One embodiment of the present disclosure relates to a method for controlling and eradicating invertebrate pests, comprising: diluting a pest-killing composition of the present disclosure (a compound of Formula 1 formulated with a surfactant, a solid diluent, and a liquid diluent, or a mixture of a compound of Formula 1 and at least one other pest-killing agent) with water; optionally adding an auxiliary agent to form a diluted composition; and contacting an invertebrate pest or its environment with an effective amount of the diluted composition.

[0346] A spray composition formed by diluting a sufficiently concentrated biocide composition with water can be sufficiently effective in controlling and eradicating invertebrate pests, but separately formulated auxiliary products can also be added to the spray tank mixture. These additional auxiliary products are commonly known as "spray auxiliary products" or "tank mixing auxiliary products" and include any substances mixed in the spray tank that improve the performance of the biocide or alter the physical properties of the spray mixture. Auxiliaries may be surfactants, emulsifiers, petroleum-based crop oils, crop-derived seed oils, acidifiers, buffers, thickeners, or defoamers. Auxiliaries are used to enhance effectiveness (e.g., bioavailability, adhesion, penetration, uniformity of coverage, and durability of protection) or to minimize or eliminate spray application problems associated with incompatibility, foaming, drift, evaporation, volatilization, and decomposition. To obtain optimal performance, auxiliary products are selected with respect to the properties of the active ingredient, formulation, and target (e.g., crops, insect pests).

[0347] Among spraying aids, oils containing crop oils, crop oil concentrates, vegetable oil concentrates, and methylated seed oil concentrates are most commonly used to improve the effectiveness of pesticides by, in some cases, promoting a more uniform and homogeneous spray deposit. In situations where there is concern about plant toxicity potentially caused by oil or other water-immiscible liquids, spray compositions prepared from the compositions of this disclosure generally do not contain oily spraying aids. However, in situations where plant toxicity caused by oily spraying aids is not commercially important, spray compositions prepared from the compositions may also contain oily spraying aids, which may potentially further increase the control of invertebrate pests and rainfastness.

[0348] Products identified as “crop oil” typically contain 95–98% paraffin or naphtha-based petroleum and 1–2% one or more surfactants that function as emulsifiers. Products identified as “crop oil concentrate” typically consist of 80–85% emulsifying petroleum-based oil and 15–20% nonionic surfactants. Products precisely identified as “vegetable oil concentrate” typically consist of 80–85% vegetable oil (i.e., most commonly seed oil or fruit oil derived from cotton, linseed, soybean, or sunflower) and 15–20% nonionic surfactants. Auxiliary performance can be improved by replacing vegetable oil with methyl esters of fatty acids, typically derived from vegetable oil. Examples of methylated seed oil concentrates include MSO® Concentrate (UAP-Loveland Products, Inc.) and Premium MSO Methylated Spray Oil (Helena Chemical Company).

[0349] The amount of auxiliary agents added to the spray mixture is generally about 2.5% by volume or less, and more typically, it is about 0.1% to 1% by volume. The application rate of auxiliary agents added to the spray mixture is typically about 1 to 5 liters per hectare. Typical examples of spray auxiliary agents include Adigor® (Syngenta) 47% methylated rapeseed oil in liquid hydrocarbons, Silwet® (Helena Chemical Company) polyalkylene oxide-modified heptamethyltrisiloxane, and Assist® (BASF) 17% surfactant blend in 83% paraffin-based mineral oil.

[0350] Non-agricultural applications include protecting animals, particularly vertebrates, more specifically warm-blooded vertebrates (e.g., mammals or birds), most specifically mammals, from invertebrate parasitic pests by administering to the animal to be protected a parasitoidally effective (i.e., biologically effective) amount of the compounds of this disclosure, typically in the form of compositions formulated for animal use. Of particular note are methods for protecting animals, comprising administering to the animal a parasitoidally effective amount of the compounds of this disclosure. The terms “parasitoid” and “in a parasitoid manner” as used in this disclosure and claims refer to an observable effect on an invertebrate parasitic pest to achieve protection of an animal from the pest. Parasitoid effects typically relate to reducing the occurrence or activity of the target invertebrate parasitic pest. Such effects on pests include necrosis, death, stunted growth, reduced motility or reduced ability to remain on or within a host animal, reduced feeding, and inhibition of reproduction. These effects on invertebrate parasitic pests enable the control and eradication (including prevention, reduction, or elimination) of the spread or infection of animal parasites. Examples of invertebrate parasitic pests that can be controlled by administering a parasiticidal amount of the compounds disclosed to the protected animals include ectoparasites (arthropods, mites, etc.) and endoparasites (parasitic helminths, such as nematodes, trematodes, tapeworms, and acanthocephalus). In particular, the compounds of this disclosure are effective against ectoparasites including: flies, e.g., stable flies (Haematobia (Lyperosia) irritans), stable flies (Stomoxys calcitrans), Simulium spp. (black flies), tsetse flies (Glossina spp.), Hydrotaea irritans (head flies), Musca autumnalis (face flies), houseflies (Musca domestica), Morellia simplex (sweat flies), and horseflies (Tabanus spp.))(botfly), Hypoderma bovis, Hypoderma lineatum, Lucilia sericata, Lucilia cuprina (green blowfly), Calliphora spp. (blowfly), Protophormia spp., Oestrus ovis (sheep fly), Culicoides spp. (midge), Hippobosca equine, Gastrophilus instestinalis, Gastrophilus haemorrhoidalis and Gastrophilus naslius Louses, such as lice (e.g., Bovicola (Damalinia) bovis, Bovicola equi, Haematopinus asini, Felicola subrostratus, Heterodoxus spiniger, Lignonathus setosus, and dog lice (Trichodectes canis), sheep flies, such as Melophagus ovinus, mites, such as Psoroptes spp., Sarcoptes scabei, Chorioptes bovis, Demodex equi ( equi), the genera Cheyletiella, Notoedes cati, Trombicula, and Otodectes cyanotis (ear mites), ticks such as Ixodes and Boophilus.), and the genera Rhipicephalus, Amblyomma, Dermacentor, Hyalomma, and Haemaphysalis, as well as fleas, such as the cat flea (Ctenocephalides felis) and the dog flea (Ctenocephalides canis).

[0351] Non-agricultural uses in the field of veterinary medicine include, by conventional means, enteral administration in the form of tablets, capsules, drinks, drench formulations, granules, pastes, boluses, feedthrough procedures or suppositories; parenteral administration, such as by injection (including intramuscular, subcutaneous, intravenous or intraperitoneal) or implantation; and nasal administration, such as topical administration via articles containing the compounds or compositions of the Disclosure, such as by immersion or immersion, spraying, washing, powder coating or application to small areas of an animal, such as collars, ear tags, tailbands, limb bands or halters.

[0352] Typically, the parasitic 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 in accordance with standard practice and with respect to the intended route of administration (e.g., oral, topical, or parenteral administration, e.g., injection). In addition, suitable carriers are selected based on their compatibility with one or more active ingredients in the composition, including considerations such as stability to pH and moisture content. Of particular note are compositions for protecting animals from invertebrate parasitic pests, comprising a parasitically effective amount of the compound of the present disclosure and at least one carrier.

[0353] For parenteral administration, including intravenous, intramuscular, and subcutaneous injection, the compounds of this disclosure may be formulated in suspensions, solutions, or emulsions in oily or aqueous vehicles and may contain adjuvants, such as suspending agents, stabilizers, and / or dispersants. Pharmaceutical compositions for injection preferably comprise an aqueous solution of an aqueous form of the active ingredient (e.g., a salt of the active compound) in a physiologically compatible buffer containing other excipients or adjuvants known in the art for pharmaceutical formulations.

[0354] 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 retainers, and feed / water / lick blocks, the compounds of this disclosure may 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, ethyl hydroxycellulose), 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 may be added as needed. Pastes and gels often also contain adhesives (e.g., acacia, alginate, bentonite, cellulose, xanthan gum, colloidal aluminum magnesium silicate) that help the composition remain in contact with the oral cavity and not easily discharged.

[0355] When the parasitoid composition is in the form of a feed concentrate, the carrier is typically selected from high-performance feeds, feed grains, or protein concentrates. Such feed concentrate-containing compositions may contain, in addition to the parasitoid active ingredient, additives that promote animal hygiene or growth, improve the quality of meat derived from slaughtered animals, or otherwise be useful for livestock farming. Examples of these additives include vitamins, antibiotics, chemotherapeutic agents, bacteriostatic agents, fungiostatic agents, anticoccidial agents, and hormones.

[0356] The compounds of this disclosure have been found to possess desirable pharmacokinetic and pharmacodynamic properties that enable systemic availability from oral administration and ingestion. Therefore, after ingestion by the protected animal, a parasitoidally effective concentration of the compounds of this disclosure in the bloodstream protects the treated animal from blood-sucking pests, such as fleas, ticks, and lice. Of particular note, there is a composition for protecting animals from invertebrate parasitic pests in the form of oral administration (i.e., comprising a parasitoidally effective amount of the compounds of this disclosure, plus one or more carriers selected from binders and fillers suitable for oral administration and feed concentrate carriers).

[0357] Formulations for topical administration are typically in the form of powders, creams, suspensions, sprays, emulsions, foams, pastes, aerosols, ointments, ointments, or gels. More typically, topical formulations are water-soluble solutions, which may be in the form of concentrates that are diluted before use. Parasiticidal compositions suitable for topical administration typically comprise the compounds of this disclosure and one or more topically suitable carriers. In topical application of a parasiticidal composition to the external surface of an animal as a line or spot (i.e., “spot-on” treatment), the active ingredient migrates across the animal’s surface to cover most or all of its external 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 comprise at least one organic solvent to facilitate the transport of the active ingredient across the skin and / or its penetration into the animal’s epidermis. Commonly used solvents as carriers in such formulations include propylene glycol, paraffin, aromatic compounds, esters such as isopropyl myristate, glycol ethers, and alcohols such as ethanol and n-propanol.

[0358] The application rate required for effective control (i.e., the "biologically effective amount") depends on factors such as the species of invertebrate being controlled, the life cycle, life stage, size, location, timing, host crop or animal, foraging behavior, reproductive behavior, ambient humidity, and temperature. Under normal circumstances, an application rate of approximately 0.01 to 2 kg of active ingredient per hectare is sufficient to control and eradicate pests in agricultural ecosystems, although sometimes 0.0001 kg / hectare may suffice, or 8 kg / hectare may be required. For non-agricultural uses, the effective application rate ranges from approximately 1.0 to 50 mg / square meter, although sometimes 0.1 mg / square meter may suffice, or 150 mg / square meter may be required. Those skilled in the art can easily determine the biologically effective amount necessary for the desired level of invertebrate pest control.

[0359] Generally, for veterinary use, the compound of Formula 1, its N-oxide, or salt is administered in a parasiticidal amount to an animal to be protected from invertebrate parasitic pests. The parasiticidal amount is the amount of active ingredient required to achieve an observable effect and reduce the appearance or activity of the target invertebrate parasitic pest. Those skilled in the art will understand that the effective dose for parasitization may vary depending on the various compounds and compositions of this disclosure, the desired parasitic effect and duration, the target invertebrate pest species, the animal to be protected, and the method of application, and that the amount required to achieve a particular result can be determined by simple experimentation.

[0360] For oral administration to homeothermic animals, the daily dose of the compound disclosed herein is typically in the range of about 0.01 mg / kg to about 100 mg / kg, more typically about 0.5 mg / kg to about 100 mg / kg (animal body weight). For topical (e.g., skin) administration, immersion and spray typically contain the compound disclosed in a concentration of about 0.5 ppm to about 5000 ppm, more typically about 1 ppm to about 3000 ppm.

[0361] Recent advances in computer processing power have given scientists an unprecedented opportunity to introduce in silico tools to predict and investigate the molecular basis of xenobiotic exposure, along with the potential adverse outcomes associated with these events. While current computational models cannot simply replace all in vivo or in vitro experimental approaches, they still provide valuable tools for generating hypotheses, flagging compounds of interest, and assisting in prioritizing and aligning chemicals for appropriate in vitro or in vivo studies.

[0362] Computational / predictive toxicology is a rapidly evolving field that integrates information and data from various sources to develop mathematical and computer-based models for better understanding and predicting the interactions between chemical agents and bioorganisms across many scales (e.g., populations, individuals, cells, and molecules). It can be considered to encompass two broad areas: (1) Development and application of two-dimensional (2D) models via a first principle (e.g., structural motifs that drive easy chemical reactivity) (Wijeyesakere, SJet al.c Development of a Profiler for Facile Chemical Reactivity Using the Open-Source Konstanz Information Miner.Appl.Vitr.Toxicol.,4,202-213,2018). Furthermore, if experimental data of similar molecules are available, quantitative structure-activity relationship (QSAR) techniques such as trend analysis can be performed to predict dosimetry for biological outcomes of interest (e.g., prediction of 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) Using a “big data” approach to collect all available information on specific outcomes / modes of action (e.g., mitochondrial inhibitors (Wijeyesakere, S.Jet et al. Hybrid Machine-Learning / SMARTS Profiling Model for Mitochondrial Inhibition. Appl. Vitr. Toxicol., 5, 196-204, 2019) or predictive models to identify those that can interact with defined neuronal receptors (Wijeyesakere, S.Jet et al. Prediction of cholinergic compounds by machine-learning. Comput. Toxicol., 13, 100119, 2020) and extending such two-dimensional assessments to three-dimensional methods such as docking and molecular dynamics (MD) simulations to further investigate the molecular basis of interactions between toxic substances and known / propositional 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).

[0363] Specific compounds of formula 1 prepared by the methods and modifications described in schemes 1-10 and synthesis examples 1-2 are shown in the following index table A. For mass spectral data (MS), the reported value is the molecular weight (M+1) of the highest isotopic parent ion formed by adding H+ (molecular weight 1) to the molecule, as observed by mass spectrometry using atmospheric pressure chemical ionization (AP+). Melting point data (MP) is reported as a temperature range. Alternative molecular ion peaks (e.g., M+2 or M+4) that occur in compounds containing multiple halogens are not reported.

[0364] The following abbreviations are used in the index table below. Cmpd means compound, t means tertiary, c means cyclo, Me means methyl, Et means ethyl, Pr means propyl, i-Pr means isopropyl, Bu means butyl, c-Pr means cyclopropyl, c-Pn means cyclopentyl, c-Hx means cyclohexyl, t-Bu means tertiary butyl, Ph means phenyl, OMe means methoxy, SMe means methylthio, and SO2Me means methylsulfonyl. The dashed lines in the structural fragments indicate the binding points of the fragment to the remainder of the molecule. The abbreviation "Ex." means "example," followed by a number indicating a synthetic example in which the compound was prepared.

[0365] [Table 54]

[0366] [Table 55]

[0367] [Table 56]

[0368] [Table 57]

[0369] Table 58

[0370] Table 59

[0371] Table 60

[0372] Table 61

[0373] Table 62

[0374] Table 63

[0375] Table 64

[0376] Table 65

[0377] Table 66

[0378] Table 67

[0379] Table 68

[0380] Table 69

[0381] Table 70

[0382] Table 71

[0383] Table 72

[0384] Table 73

[0385] Table 74

[0386] Table 75

[0387] Table 76

[0388] Table 77

[0389] Table 78

[0390] Table 79

[0391] Table 80

[0392] Table 81

[0393] Table 82

[0394] Table 83

[0395] Table 84

[0396] Table 85

[0397] Table 86

[0398] Table 87

[0399] Table 88

[0400] Table 89

[0401] Table 90

[0402] Table 91

[0403] Table 92

[0404] Table 93

[0405] Table 94

[0406] Table 95

[0407] Table 96

[0408] Table 97

[0409] Table 98

[0410] Table 99

[0411] Table 100

[0412] Table 101

[0413] Table 102

[0414] Table 103

[0415] Table 104

[0416] Table 105

[0417] Table 106

[0418] Table 107

[0419] Table 108

[0420] Table 109

[0421] [Table 110]

[0422] [Table 111]

[0423] The following tests demonstrate the control efficacy of the compounds disclosed herein against specific pests. “Control efficacy” refers to the suppression 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 a description of the compounds.

[0424] Biological examples The following tests demonstrate the control efficacy of the compounds disclosed herein against specific pests. “Control efficacy” refers to the suppression 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 a description of the compounds.

[0425] Formulation and spraying method for tests A to E The test compound was formulated using a solution containing 10% acetone, 90% water, and 300 ppm of Activator 90® nonionic surfactant (Loveland Products, Loveland, Colorado, USA). The formulated compound was sprayed / applied at a volume of 1 mL using an atomizing nozzle positioned 1.27 cm (0.5 inches) above the top of each test unit. Each test was repeated three times, spraying the indicated volume of the test compound.

[0426] Test A To evaluate the control of corn plant hoppers (Peregrinus maidis (Ashmead)) by contact and / or systemic means, the test unit consisted of a small open container containing 3-4 day old corn plants. White sand was added to the soil before application of the test compound.

[0427] The test compound was prepared and sprayed in three replicates as described above at concentrations of 250, 50, 10, and 2 ppm. After spraying the prepared test compound, the test units were allowed to dry for one hour, and then approximately 15-20 nymphs (18-21 days old) were post-infested. A black mesh cap was placed on top of each test unit, and the units were kept in a cultivation box at 22-24°C and 50-70% relative humidity for six days. Next, each test unit was visually evaluated for insect mortality.

[0428] Of the compounds of Formula 1 tested at 250 ppm, the following resulted in at least 80% mortality: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 12, 14, 18, 19, 20, 21, 29, 32, 33, 48, 49, 50, 52, 53, 54, 58, 60, 61, 62, 63, 64, 65, 66, 67, 71, 7 2, 79, 80, 82, 83, 84, 86, 94, 95, 111, 116, 117, 128, 129, 130, 141, 151, 152, 159, 160, 162, 163, 164, 183, 186, 207, 208, 213, 219, 221, 225, 226, 228, 229, 231, 233, 234, 235.

[0429] Of the compounds of Formula 1 tested at 50 ppm, the following resulted in at least 80% mortality: 2, 7, 8, 9, 10, 12, 14, 18, 19, 20, 21, 29, 32, 33, 48, 49, 52, 53, 60, 61, 62, 63, 64, 65, 66, 67, 71, 72, 79, 80, 82, 83, 84, 86, 94, 95, 111, 116, 117, 128, 129, 130, 141, 151, 152, 159, 160, 162, 163, 164, 183, 186, 207, 208, 213, 219, 221, 225, 226, 228, 229, 231, 233, 234, 235.

[0430] Test C To evaluate the control of the green peach aphid (Myzus persicae (Sulzer)) by contact and / or systemic means, the test units consisted of small open containers containing 12-15 day old radish plants. Before application of the compound, each test unit was pre-infested by placing 30-40 aphids on leaf fragments cut from cultured plants onto the leaves of the test plants (cut leaf method). As the leaf fragments dried, the aphids migrated onto the test plants. After pre-infestation, the soil in the test units was covered with a layer of sand.

[0431] The test compound was prepared and sprayed in three replicates at concentrations of 250, 50, and 10 ppm as described above. After spraying the prepared test compound, each test unit was allowed to dry for one hour before a black mesh cap was placed on top. The test units were kept in a growth chamber at 19–21°C and 50–70% relative humidity for six days. Next, each test unit was visually evaluated for insect mortality.

[0432] Of the compounds of Formula 1 tested at 250 ppm, the following resulted in at least 80% mortality: 8, 10, 18, 21, 32, 33, 52, 53, 63, 67, 72, 79, 80, 82, 83, 84, 86, 94, 95, 103, 116, 117, 128, 129, 130, 141, 151, 159, 160, 164, 219, 221, 226, 228, 231, 233, 234, and 235.

[0433] Of the compounds of Formula 1 tested at 50 ppm, the following resulted in at least an 80% mortality rate: 18, 21, 83, 94, 117, 128, 129, 130, 141, 219, 228, and 234.

[0434] Test D To evaluate the control of cotton aphids (Aphis gossypii (Glover)) by contact and / or systemic means, the test unit consisted of a small open container containing a 5-day-old okra plant. The soil of the test unit was covered with a layer of sand, and 30-40 insects were pre-infested on a single leaf according to the cut-leaf method.

[0435] The test compound was formulated and sprayed in three replicates at concentrations of 250, 50, and 10 ppm as described above. After spraying, the test units were maintained in a growth chamber at 19°C and 70% relative humidity for 6 days. Next, each test unit was visually evaluated for insect mortality.

[0436] Of the compounds of Formula 1 tested at 250 ppm, the following resulted in at least 80% mortality: 2, 3, 7, 8, 9, 10, 12, 13, 14, 16, 18, 19, 20, 21, 27, 32, 33, 48, 49, 50, 52, 53, 54, 57, 58, 59, 60, 61, 62, 63, 64, 66, 67, 68, 71, 72, 79, 80, 82, 83, 84, 86, 94, 95, 103, 116, 117, 128, 130, 132, 137, 141, 151, 159, 162, 219, 221, 222, 224, 226, 228, 229, 231, 233, 234, 235.

[0437] Of the compounds of Formula 1 tested at 50 ppm, the following resulted in at least 80% mortality: 7, 8, 9, 10, 12, 14, 18, 21, 27, 32, 33, 48, 52, 53, 57, 60, 61, 62, 63, 64, 72, 79, 80, 82, 83, 84, 86, 94, 95, 103, 116, 117, 128, 130, 132, 137, 141, 151, 159, 219, 221, 222, 228, 229, 231, 233, 234, 235.

[0438] Test F Test units for evaluating the control of tobacco whiteflies (Bemisia tabaci (Gennadius)) by contact and / or systemic means consisted of small, open containers containing 8-9 day-old soybean plants. Prior to spraying, both cotyledons and simple leaves were removed, leaving one true leaf for the assay. Adult whiteflies were allowed to lay eggs on the plants before removing them from the test units. Soybean plants with at least 15 eggs attached were used in the spraying tests.

[0439] The test compound was prepared and sprayed at 50 ppm. After spraying, the test units were allowed to dry for 1 hour. The cylinder was then removed, and the units were placed in a growth chamber and kept at 28°C and 50-70% relative humidity for 13 days. Next, each test unit was visually evaluated for insect mortality.

[0440] Of the compounds of Formula 1 tested at 250 ppm, the following resulted in at least 70% mortality: 2, 7, 8, 9, 10, 11, 12, 14, 18, 19, 21, 27, 32, 33, 48, 49, 53, 60, 61, 62, 63, 64, 66, 67, 68, 72, 80, 82, 83, 84, 86, 94, 95, 101, 102, 103, 116, 128, 129, 132, 141, 151, 159, 219, 221, 224, 225, 226, 228, 229, 231, 232, 233, 234, 235.

[0441] Of the compounds of Formula 1 tested at 50 ppm, the following showed a mortality rate of at least 70%: 2, 8, 9, 10, 11, 18, 21, 27, 32, 33, 53, 60, 64, 66, 72, 80, 83, 84, 94, 101, 102, 103, 116, 128, 129, 132, 141, 151, 159, 219, 221, 226, 228, 231, 233, 234, 235.

[0442] Test G To evaluate the control of diamondback moth (Plutella xylostella L.) by contact and / or systemic means, each test unit consisted of a small open container containing 10-12 day old mustard plants.

[0443] The test compound was prepared and sprayed at 250 ppm in three replicates as described above. After spraying, the test units were allowed to dry for one hour, and then 30-50 first-instar larvae were released into them. A black mesh cap was placed on top of each container. The test units were kept in a cultivation box at 24-25°C and 70% relative humidity for six days. Next, plant feeding damage was visually assessed based on the leaves and stems consumed, and the larval mortality rate was evaluated.

[0444] Of the compounds of Formula 1 tested at 250 ppm, the following yielded very good or excellent levels of control efficacy (less than 20% feeding damage): 3, 46, 58, 67, 75, 77, 78, 82, 83, 93, 97, 98, 99, 100, 112, 121, 142, 145, 148, 158, and 160.

Claims

1. Formula 1 【Chemistry 1】 (In the formula, L is CR ５ R ６ 、CR ５ R ６ CR ５ R ６ 、OCR ５ R ６ 、CR ５ R ６ O、CR ５ R ６ NR ７ 、NR ７ CR ５ R ６ 、C(=E)NR ７ 、NR ７ C(=E)、C(=E)CR ５ R ６ 、CR ５ R ６ C(=E)、C(=CR ５ R ６ )、CR ５ =CR ６ or C(=E), and E is O, S, or NR ８ And, m is 0, 1, 2, 3, 4, 5, Each R １ These are, independently, halogen, cyano, nitro, hydroxy, and SF ５ C(O)NH ２ , C(O)NR １０ R １１ , C(=NR １３ ) NR １０ R １１ , C(=NR １３ ) R １４ OC(O)R １４ NR １０ R １１ NR １３ C(O)R １４ , C(O)R １４ , S(O) ｎ R １４ OS(O) ｎ R １４ , Si(R １４ ) ３ OSi(R) １４ ) ３ Or MQ ａ or non-substituted or at least one R ｘ C is replaced by １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, C ３ ~C ６ It is either a cycloalkoxy or has two R atoms on adjacent ring atoms. １ The substituents, together with the carbon atom to which they are bonded, form a 4- to 7-membered ring comprising a carbon atom and up to three heteroatoms independently selected from up to two oxygen atoms, one sulfur atom, and up to three nitrogen atoms, wherein up to two carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is S, S(O) or S(O) ２ Selected from, the ring is either unsubstituted or has at least one R ｘ It has been replaced with, Each R ２ 、R ３ 、R ４ is independently hydrogen, halogen, cyano, nitro, hydroxy, SF ５ 、C(O)H、C(O)NH ２ 、C(O)NR １０ R １１ 、C(=NR １３ [[ID=十六]])NR １０ R １１ 、C(=NR １３ )R １４ 、OC(O)R １４ 、NR １０ R １１ 、NR １３ C(O)R １４ 、C(O)R １４ 、S(O) ｎ R １４ 、OS(O) ｎ R １４ 、Si(R １４ ) ３ 、OSi(R １４ ) ３ or MQ ａ or is unsubstituted or substituted with at least one R ｘ is C １ ~C ６ alkyl, C ３ ~C ６ cycloalkyl, C １ ~C ６ alkoxy, C ３ [[ID=七十]]~C ６ cycloalkoxy, C ２ ~C ６ alkenyl or C ２ ~C ６ alkynyl, or two substituents (R ２ and R ３ or R ３ and R ４ )together with the carbon atom to which they are attached form a 4- to 7-membered ring containing ring members selected from carbon atoms and up to two oxygen atoms, one sulfur atom, and up to three nitrogen atoms, up to two of the carbon atom ring members being independently selected from C(=O) and C(=S), and the sulfur atom ring member being S, S(O) or S(O) ２ Selected from, the ring is either unsubstituted or has at least one R ｘ It has been replaced with, M is a direct bond, O, S, S(O), S(O) ２ Or NR ９ And, R ５ and R ６ These are independently hydrogen, hydroxyl, halogen, cyano, and C. １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C ３ ~C ６ Cycloalkoxy, C １ ~C ６ Alkylthio or C １ ~C ６ It is a haloalkylthio, or R bonded to the same carbon atom ５ and R ６ Together with the carbon atoms to which they are bonded, they form a 3- to 7-membered ring comprising a carbon atom and ring members selected independently from one oxygen atom, one sulfur atom, and up to three heteroatoms, the maximum two carbon atom ring members being independently selected from C(=O) and C(=S), and the sulfur atom ring member being S, S(O) or S(O) ２ Selected from, the ring is either unsubstituted or has at least one R ｘ It is replaced with, or CR ５ R ６ CR ５ R ６ In this case, each R ５ and R ６ It is bonded to each of the first and second adjacent carbon atoms, and together with the carbon atoms to which they are bonded, can form a 3 to 7-membered ring comprising a carbon atom and ring members selected independently from one oxygen atom, one sulfur atom and up to three heteroatoms, up to two carbon atom ring members independently selected from C(=O) and C(=S), and the sulfur atom ring member is S, S(O) or S(O) ２ Selected from, the ring is either unsubstituted or has at least one R ｘ It has been replaced with, Each R ７ These are independently H, C(O)R １５ , or S(O) ２ R １５ , or Q ｂ or non-substituted or at least one R ｘ C is replaced by １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ３ ~C ６ Cycloalkyl, C ２ ~C ６ Alkenil or C ２ ~C ６ It is alkinyl, Each R ８ NR is independent. １０ R １１ , OR １２ , C(=NR １３ ) R １４ , C(O)NR １０ R １１ , C(O)R １４ Or S(O) ｎ R １４ Or each is unsubstituted or at least one R ｘ Phenyl, C substituted with １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, C ２ ~C ６ Alkenil or C ２ ~C ６ It is alkinyl, Each R ９ H, NR １０ R １１ , OR １２ , C(=NR １３ ) R １４ , C(O)NR １０ R １１ , C(O)R １４ Or S(O) ｎ R １４ Or each is unsubstituted or at least one R ｘ Phenyl, C substituted with １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, C ２ ~C ６ Alkenil or C ２ ~C ６ It is alkinyl, Each R ｘ These are independently halogen, cyano, nitro, hydroxy, and C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C １ ~C ６ Haloalkyl, C ３ ~C ６ Cycloalkyl, C ３ ~C ６ Halocycloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C ３ ~C ６ Cycloalkoxy, C ３ ~C ６ Halocycloalkoxy, C(O)NH ２ , C(O)NR １０ R １１ , C(=NR １３ ) R １４ OC(O)R １４ NR １０ R １１ NR １４ C(O)R １４ , C(O)R １４ , S(O) ｎ R １４ OS(O) ｎ R １４ , Si(R １４ ) ３ OSi(R) １４ ) ３ Or Q ｂ And, Each R １０ Independently, C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl or C ２ ~C ６ Alkinyl, C(O)R １５ or S(O) ２ R １５ Alternatively, they may be unsubstituted, or halogens, cyano, nitro, or C. １ ~C ４ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy and C １ ~C ４ A phenyl or a 5- or 6-membered heterocyclic aromatic ring substituted with at least one substituent independently selected from the group consisting of haloalkoxys, Each R １１ These are H and C, independently. １ ~C ６ Alkyl or C １ ~C ４ It is a haloalkyl, or R １０ and R １１ Together with the nitrogen atoms to which they are bonded, they form a 3- to 7-membered ring comprising a carbon atom and ring members selected independently from one oxygen atom, one sulfur atom, and up to three heteroatoms, the maximum two carbon atom ring members being independently selected from C(=O) and C(=S), and the sulfur atom ring member being S, S(O) or S(O) ２ Selected from the above, the ring is either unsubstituted or contains halogen, cyano, nitro, or C １ ~C ４ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy and C １ ~C ４ It is substituted with at least one substituent independently selected from the group consisting of haloalkoxys, Each R １２ These are H and C, independently. １ ~C ４ Alkyl, C ３ ~C ６ Cycloalkyl or C １ ~C ４ Haloalkyl or unsubstituted, or halogen, cyano, nitro, C １ ~C ４ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy and C １ ~C ４ A phenyl compound substituted with at least one substituent independently selected from the group consisting of haloalkoxys, Each R １３ H, OR １６ , S(O) ｎ R １７ , C(O)OR １７ , C(O)R １７ or NHR １８ And, Each R １４ These are independently H, or C which is either unsubstituted or substituted with at least one halogen, cyano, or nitro. １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, C ２ ~C ６ Alkenyl or C ２ ~C ６ Alkinyl, C １ ~C ６ Alkoxy, C ３ ~C ６ Cycloalkoxy, or C(O)OR １７ , C(O)NR ２２ R ２３ NR ２２ R ２３ NR ２４ C(O)R １７ , C(O)R １７ Or Q ｂ And, Each R １５ Independently, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy or NR ２２ R ２３ Alternatively, they may be unsubstituted, or halogens, cyano, nitro, or C. １ ~C ４ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy and C １ ~C ４ A phenyl or a 5- or 6-membered heterocyclic aromatic ring substituted with at least one substituent independently selected from the group consisting of haloalkoxys, Each R １６ Independently, C １ ~C ４ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ４ Haloalkyl, C(O)R １９ , S(O) ｎ R ２０ Or Q ｂ And, Each R １７ Independently, C １ ~C ４ Alkyl or C １ ~C ４ It is a haloalkyl, R １８ C １ ~C ４ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ４ Haloalkyl, C(O)R １９ Or C(O)OR ２１ Or they are unsubstituted, or they are halogens, cyano, nitro, or C １ ~C ４ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy and C １ ~C ４ A phenyl compound substituted with at least one substituent independently selected from the group consisting of haloalkoxys, Each R １９ Independently, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ６ Cycloalkyl, C ３ ~C ６ Halocycloalkyl, C ３ ~C ６ Cycloalkylalkyl or C ３ ~C ６ Halocycloalkylalkyl or unsubstituted, or halogen, cyano, nitro, C １ ~C ４ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy and C １ ~C ４ A phenyl compound substituted with at least one substituent independently selected from the group consisting of haloalkoxys, Each R ２０ Independently, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ６ Cycloalkyl, C ３ ~C ６ Halocycloalkyl, C ３ ~C ６ Cycloalkylalkyl or C ３ ~C ６ Halocycloalkylalkyl or unsubstituted, or halogen, cyano, nitro, C １ ~C ４ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy and C １ ~C ４ A phenyl compound substituted with at least one substituent independently selected from the group consisting of haloalkoxys, Each R ２１ Independently, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ６ Cycloalkyl, C ３ ~C ６ Halocycloalkyl, C ３ ~C ６ Cycloalkylalkyl or C ３ ~C ６ Halocycloalkylalkyl or unsubstituted, or halogen, cyano, nitro, C １ ~C ４ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy and C １ ~C ４ A phenyl compound substituted with at least one substituent independently selected from the group consisting of haloalkoxys, Each R ２２ These are H and C, independently. １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl or C ２ ~C ６ Alkinyl, C(O)R ２５ or S(O) ２ R ２５ Alternatively, they may be unsubstituted, or halogens, cyano, nitro, or C. １ ~C ４ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy and C １ ~C ４ A phenyl or a 5- or 6-membered heterocyclic aromatic ring substituted with at least one substituent independently selected from the group consisting of haloalkoxys, Each R ２３ These are H and C, independently. １ ~C ６ Alkyl or C １ ~C ４ It is a haloalkyl, or R ２２ and R ２３ Together with the nitrogen atoms to which they are bonded, they form a 3- to 7-membered ring comprising a carbon atom and ring members selected from one oxygen atom, one sulfur atom, and up to two heteroatoms independently selected from up to two nitrogen atoms, wherein the up to two carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is S, S(O) or S(O) ２ Selected from the above, the ring is either unsubstituted or contains halogen, cyano, nitro, or C １ ~C ４ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy and C １ ~C ４ It is substituted with at least one substituent independently selected from the group consisting of haloalkoxys, Each R ２４ H or C １ ~C ４ It is alkyl, Each R ２５ Independently, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy or C １ ~C ６ Haloalkoxys, or each is unsubstituted, or contains halogens, cyano, nitro, or C. １ ~C ４ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy and C １ ~C ４ A phenyl or a 5- or 6-membered heterocyclic aromatic ring substituted with at least one substituent independently selected from the group consisting of haloalkoxys, Each Q ａ Each is independently a phenyl, a 5 or 6-membered heterocyclic aromatic ring, or a 3- to 6-membered heterocyclic non-aromatic ring, each ring comprising a carbon atom and a ring member selected independently from one oxygen atom, one sulfur atom, and up to four heteroatoms selected independently from up to four nitrogen atoms, up to two carbon atom ring members being independently selected from C(=O) and C(=S), and the sulfur atom ring member being S, S(O), or S(O) ２ Selected from, each ring is either unsubstituted or contains halogen, cyano, nitro, or C １ ~C ４ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy and C １ ~C ４ It is substituted with at least one substituent independently selected from the group consisting of haloalkoxys, Each Q ｂ Each is independently a phenyl, a 5 or 6-membered heterocyclic aromatic ring, or a 3- to 6-membered heterocyclic non-aromatic ring, each ring comprising a carbon atom and a ring member selected independently from one oxygen atom, one sulfur atom, and up to four heteroatoms selected independently from up to four nitrogen atoms, up to two carbon atom ring members being independently selected from C(=O) and C(=S), and the sulfur atom ring member being S, S(O), or S(O) ２ Selected from, each ring is either unsubstituted or contains halogen, cyano, nitro, or C １ ~C ４ Alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy and C １ ~C ４ It is substituted with at least one substituent independently selected from the group consisting of haloalkoxys, and Each n is independently 0, 1, or 2. However, R ２ , R ３ and R ４ If is H and L is CH(OH), then R １ is anything other than 3-trifluoromethyl, and L is C(=O)NR ７ And when nitrogen is linked to the phenyl ring, R ２ , R ３ or R ４ (At least one of them is not H) A compound selected from, its N-oxide, or salt.

2. L is CR ５ R ６ The compound according to claim 1.

3. L is CR ５ R ６ CR ５ R ６ The compound according to claim 1.

4. L stands for OCR ５ R ６ The compound according to claim 1.

5. L is CR ５ R ６ The compound according to claim 1, wherein the compound is O.

6. L is CR ５ R ６ NR ７ The compound according to claim 1.

7. L stands for NR ７ CR ５ R ６ The compound according to claim 1.

8. L is C(=E)NR ７ The compound according to claim 1.

9. L stands for NR ７ The compound according to claim 1, wherein C (=E).

10. L is C(=E)CR ５ R ６ The compound according to claim 1.

11. L is CR ５ R ６ The compound according to claim 1, wherein C (=E).

12. L is C (=CR ５ R ６ The compound according to claim 1, which is the compound described in claim 1.

13. L is CR ５ =CR ６ The compound according to claim 1.

14. The compound according to claim 1, wherein L is C (=E).

15. The compound according to any one of claims 1 to 14, wherein E is O or S.

16. R １ These are halogens, cyano, nitro, hydroxy, and SF ５ C(O)NH ２ , C(O)NR １０ R １１ , C(=NR １３ ) NR １０ R １１ , C(=NR １３ ) R １４ OC(O)R １４ NR １０ R １１ NR １３ C(O)R １４ , C(O)R １４ , S(O) ｎ R １４ OS(O) ｎ R １４ , Si(R １４ ) ３ OSi(R) １４ ) ３ Or MQ ａ or non-substituted or at least one R ｘ C is replaced by １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy or C ３ ~C ６ A compound according to any one of claims 1 to 15, wherein it is a cycloalkoxy.

17. The compound according to any one of claims 1 to 15, wherein m is 0, 1, or 2.

18. N-(7-methyl[1,2,4]triazolo[1,5-a]pyridine-5-yl)-4-(trifluoromethyl)benzamide, 7-methyl-5-[[4-(trifluoromethyl)phenyl]methoxy][1,2,4]triazolo[1,5-a]pyridine, (7-methyl[1,2,4]triazolo[1,5-a]pyridine-5-yl)[4-(trifluoromethoxy)phenyl]methanone, 5-[fluoro[4-(trifluoromethoxy)phenyl]methyl]-7-methyl[1,2,4]triazolo[1,5-a]pyridine, 5-[methoxy[4-(trifluoromethoxy)phenyl]methyl]-7-methyl[1,2,4]triazolo[1,5-a]pyridine, 7-methyl-5-[[4-(trifluoromethoxy)phenyl]methyl][1,2,4]triazolo[1,5-a]pyridine, 7-methyl-5-[[4-(trifluoromethyl)phenyl]methyl][1,2,4]triazolo[1,5-a]pyridine, 5-[fluoro[4-(trifluoromethyl)phenyl]methyl]-7-methyl[1,2,4]triazolo[1,5-a]pyridine, (6-cyclopropyl-3aH-inden-4-yl)(4-(trifluoromethoxy)phenyl)methanone, 5-(fluoro(4-(trifluoromethyl)phenyl)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-(3-fluoro-4-(trifluoromethyl)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-(3-fluoro-4-(trifluoromethoxy)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-(fluoro(3-fluoro-4-(trifluoromethoxy)phenyl)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 1-(7-cyclopropyl-[1,2,4]triazolo[1,5-a]pyridine-5-yl)-1-(4-(trifluoromethoxy)phenyl)ethane-1-ol, 5-(fluoro(4-(trifluoromethoxy)phenyl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-a]pyridine, 5-(2-fluoro-4-(trifluoromethyl)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-((2-fluoro-4-(trifluoromethoxy)phenyl)(methoxy)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-(fluoro(2-fluoro-4-(trifluoromethoxy)phenyl)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 7-iodo-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-isopropyl-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-(difluoromethyl)-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-Cyclopropyl-5-(4-(trifluoromethyl)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 5-(2-fluoro-4-(trifluoromethoxy)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 7-Bromo-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-Cyclopropyl-6-(2-(3-(trifluoromethyl)phenyl)cyclopropyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-Cyclopropyl-5-((3-Fluoro-4-(trifluoromethyl)phenyl)(methoxy)methyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-Cyclopropyl-5-(Fluoro(3-Fluoro-4-(trifluoromethoxy)phenyl)methyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-Cyclopropyl-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, and 7-Cyclopropyl-5-(Fluoro(4-(trifluoromethoxy)phenyl)methyl)-[1,2,4]triazolo[1,5-a]pyridine, and Any combination of the above compounds A compound according to claim 1, selected from the group consisting of the following.

19. A composition comprising a compound according to any one of claims 1 to 18 and at least one further component selected from the group consisting of surfactants, solid diluents, and liquid diluents, wherein the composition optionally further comprises at least one further biologically active compound or agent.

20. The following structure: 【Chemistry 2】 A composition comprising α-[3-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyridine-5-methanol having and at least one further component selected from the group consisting of surfactants, solid diluents and liquid diluents, wherein the composition optionally further comprises at least one further biologically active compound or agent.

21. The aforementioned at least one further bioactive compound or agent is abamectin, acephate, acekinosyl, acetamiprid, acrinatrin, afidopiropene, amidoflumet, amitraz, avermectin, azadirachtin, azinphosmethyl, benziocarb, benfuracarb, bensultap, bifenthrin, bifenazate, bistriflurone, borate, bromantraniliprole, buprofezin, carbaryl, carbofuran, cartap, chlorantraniliprole, chlorfenapyr, chlorfluazurone, Loloprallethrin, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezine, clothianidin, cyantraniliprole, cyclaniliprole, cyclobutrifluram, cycloprothrin, cycloxapride, cyetopyrafen, cyflumetofen, cyfluthrin, β-cyfluthrin, cyhalodiamid, cyhalotrin, γ-cyhalotrin, λ-cyhalotrin, cypermethrin, α-cypermethrin, ζ-cypermethrin, cyprofuranilide, cyromazine, deltamethrin, diafenthiurone, diazinon Dichlorantraniliprole, Dierdrin, Diflovidazine, Diflubenzuron, Dimefluthrin, Dimehypo, Dimethoate, Dinotefuran, Diophenolane, Emamectin, Endosulfan, Esfenvalerate, Ethiprole, Etofenprox, Ethoxazole, Phenazaquin, Fenbutatine Oxide, Fenitrothion, Fenmezodithiaz, Phenothiocarb, Phenoxycarb, Fenpyroximate, Fenpropathrin, Fenvalerate, Fipronil, Flometquin, Flonicamide, Fluacripy Limu, fluazandinidine, flubendiamide, fluchlordiniliprole, flucitrinate, fluphenelim, flufenoxuron, fluphenoxystrobin, fluensulfone, fluhexaphon, flupentiophenox, fluopyram, flupyrimin, flupyradiflon, fluvalinate, taufluvalinate, fluxamethamide, phonophos, formetanate, fothiazate, halofenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, hydroprene, imidacloprid,Indazapiroxamet (N-(1-methylcyclopropyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide), indoxacarb, insecticide soap, isofenphos, isocycloceram, cappatefluthrin, quinoprene, lufenuron, malathion, meperfluthrin, metaflumizone, metaldehyde, methamidophos, methidathion, methiocarb, methomyl, methoprene, methoxychlor, methoxyphenozide, metofluthrin, monoclotophos, monofluorothrin, nicofluprole, nicotine, N-[1,1-dimethyl N-[1,1-dimethyl-2-(methylsulfinyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1,1-dimethyl-2-(methylsulfonyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-(1-methylcyclopropyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1-(diflu Oromethyl)cyclopropyl]-2-(3-pyridinyl)-2H-indazole-4-carboxamide, nitenpyram, nithiazine, novaron, nobiflumulon, oxamyl, oxazosulfyl, parathion, parathion-methyl, permethrin, phorate, fosalon, fosmet, phosphamidone, pyrimicarb, profenofos, profluthrin, propargit, protrefenbute, piflubamide, pymetrozine, pyrafluprole, pyrethrin (pyrethrum), pyridaben, pyridaryl, pyrifluquinazon, pyrimidifen, pyriminostrobin Pyriprole, pyriproxyfen, rotenone, ryanodine, silafluofen, spidoxamato, spinetoram, spinosad, spirobudifen, spirodiclofen, spiromesifen, spirotetramato, sulprofos, sulfoxaflor, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, kappatefluthrin, terbufos, tetrachlorantraniliprole, tetrachlorvinfos, tetramethrin, tetramethylfluthrin, tetraniliprole, thiacloprid, thiamethoxam, thiodicarb, thiosultap,The composition according to claim 19 or 20, selected from the group consisting of thiosultap-sodium, thiolantraniliprole, thioxazafen, tolfenpyrad, tralomethrin, trizamate, trichlorphon, trifluenfronate, triflumezopyrim, triflumulon, ticlopyrazoflor, Bacillus sphaericus, Bacillus thuringiensis δ-endotoxin, entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi, plant essences including synthetic extracts and unrefined oils, RNA interference-mediated target suppressors, thiolantraniliprole, and trifluenfronate.

22. A method for controlling and eradicating invertebrate pests, comprising contacting the invertebrate pest or its environment with a biologically effective amount of the compound or composition described in any one of claims 1 to 21.

23. Treated seeds comprising a compound or composition according to any one of claims 1 to 21 in an amount of about 0.0001 to 1% by weight of the seeds before treatment.

Images