Novel sulfonate benzamide compounds for controlling invertebrate pests - Patents.com

Abstract

Disclosed are compounds of formula (I), including all geometric and stereoisomers, N-oxides, and salts thereof: [Formula 1] TIFF2025512361000078.tif55170 formula, Q is (Q 1 ) or (Q 2 ) and R 1 , R 2 , R 3 , R 10 , R 11 , R 12 , A 1 and A 2 is as defined in the present disclosure. Also disclosed are compositions comprising a compound of formula (I) and methods for controlling invertebrate pests comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound or composition of the present disclosure.

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of U.S. Provisional Patent Application No. 63 / 330,809, filed April 14, 2022.

[0002] The present disclosure relates to certain sulfonate benzamide compounds, their N-oxides, salts and compositions suitable for agronomic or non-agronomic use, and methods of their use for controlling invertebrate pests, such as arthropods, in both agricultural and non-agronomic environments. [Background technology]

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

[0004] The present disclosure relates to compounds of formula 1, including all geometric and stereoisomers, N-oxides, and salts thereof, and compositions containing them and their use for controlling invertebrate pests: [ka] During the ceremony, R 1is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C6 cycloalkyl, where each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more R 6 or R 1 However, 1 to 3 R 6 or a 5-membered aromatic heterocycle containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from one oxygen, one sulfur, and up to 3 nitrogen atoms, or a 6-membered aromatic heterocycle containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each 5- to 6-membered aromatic heterocycle is selected from one or more R 6 optionally replaced with; However, R 1 is C1-C6 alkyl, R 6 is other than C1-C6 alkyl; R 2 is hydrogen, halogen, cyano, nitro; or R 2 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, where each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more R 6 optionally substituted with; or R 2 is a phenyl, or a 5-membered aromatic heterocycle containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from one oxygen, one sulfur, and up to 3 nitrogen atoms, or a 6-membered aromatic heterocycle containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or aromatic heterocycle is selected from one or more R 6 optionally substituted with; or R 2 But, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , OR 7 , NHC(O)NR 7 R8 , O.C.(O)R 7 , O.C.(O)O.R. 7 , S(O) p R 7 , SO2NR 7 R 8 , or OS(O)2R 9 and; R 3 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C6 cycloalkyl, where each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more R 6 optionally substituted with; or R 3 But, C(O)R 7 , C(O)OR 7 , N.R. 7 R 8 , OR 7 , S(O)pR 7 or SO2NR 7 R 8 and; R 4 is H, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C6 cycloalkyl, where each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more of R 6 optionally replaced with; R 5 is hydrogen or C1-C4 alkyl; or R 4 and R 5 can be taken together to form a 3- to 6-membered carbocyclic ring; R 6 is halogen, cyano, nitro; or R 6 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, where each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more X 1 optionally substituted with; or R 6is phenyl, or a 5-membered aromatic heterocycle containing carbon atoms and 1 to 3 heteroatoms independently selected from one oxygen, one sulfur, and up to 3 nitrogen atoms, or a 6-membered aromatic heterocycle containing carbon atoms and 1 to 2 nitrogen atoms, or a 3- to 6-membered non-aromatic heterocycle containing carbon atoms and 1 to 5 heteroatoms independently selected from two oxygen atoms, two sulfur atoms, and up to 2 nitrogen atoms, wherein each phenyl, 5- to 6-membered aromatic heterocycle, or 3- to 6-membered non-aromatic heterocycle is selected from one or more X 1 optionally substituted with; or R 6 But, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , OR 7 , NHC(O)NR 7 R 8 , O.C.(O)R 7 , O.C.(O)O.R. 7 , S(O)pR 7 , SO2NR 7 R 8 , or OS(O)2R 9 and; R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, where each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more R 6 optionally substituted with; or R 7 is a phenyl, or a 5-membered aromatic heterocycle containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from one oxygen, one sulfur, and up to 3 nitrogen atoms, or a 6-membered aromatic heterocycle containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or 5- to 6-membered aromatic heterocycle is selected from one or more R 6 optionally replaced with; R 8is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl, where each alkyl, alkenyl, or alkynyl is selected from one or more R 6 optionally replaced with; R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, where each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more R 6 optionally substituted with; or R 9 is a phenyl, or a 5-membered aromatic heterocycle containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from one oxygen, one sulfur, and 1 to 3 nitrogen atoms, or a 6-membered aromatic heterocycle containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or 5- to 6-membered aromatic heterocycle is selected from one or more R 6 optionally replaced with; n is 0 to 4; p is 0 to 2; Q, Q 1 Or Q 2 and; [ka] A 1 and A 2 is a 5-membered aromatic heterocycle containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from one oxygen, one sulfur, and 1 to 3 nitrogen atoms, or a 6-membered aromatic heterocycle containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each 5- to 6-membered aromatic heterocycle is selected from one or more R 6 optionally replaced with; R 10 , R 11 and R 12 is hydrogen, halogen, cyano, nitro; or R 10 , R 11 and R 12is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, where each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more R 6 optionally substituted with; or R 10 , R 11 and R 12 However, 1 to 3 R 6 or a 5-membered aromatic heterocycle containing carbon atoms and 1-3 ring members selected from one oxygen, one sulfur, and 1-3 nitrogen heteroatoms, or a 6-membered aromatic heterocycle containing carbon atoms and 1-2 nitrogen atoms, wherein each 5- to 6-membered aromatic heterocycle is selected from one or more R 6 optionally replaced with; or R 10 , R 11 and R 12 But, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , OR 7 , NHC(O)NR 7 R 8 , O.C.(O)R 7 , O.C.(O)O.R. 7 , S(O) p R 7 , SO2N p R 7 R 8 , or OS(O)2R 9 and; X 1is hydrogen, halogen, cyano, nitro, OH, CHO, CO2H, CO(C1-C4 alkyl), CO2(C1-C4 alkyl), C(O)NH(C1-C4 alkyl), C(O)N(C1-C4 alkyl)2, NH(C1-C4 alkyl), N(C1-C4 alkyl)2, O(C1-C4 alkyl), O(C1-C4 haloalkyl), NHC(O)NH(C1-C4 alkyl), NHC(O)N(C1-C4 alkyl)2, OC(O)(C1-C4 alkyl), OCO2(C1-C4 alkyl), S(O) p (C1-C4 alkyl), S(O) p (C1-C4 haloalkyl), SO2NH(C1-C4 alkyl), SO2N(C1-C4 alkyl)2, OS(O)2(C1-C4 alkyl), OS(O)2(C1-C4 haloalkyl); or X 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl or C4-C8 cycloalkylalkyl; wherein each alkyl, alkenyl, alkynyl or cycloalkyl is selected from the group consisting of one or more of halogen, cyano, nitro, OH, CHO, CO2H, CO(C1-C4 alkyl), CO2(C1-C4 alkyl), C(O)NH(C1-C4 alkyl), C(O)N(C1-C4 alkyl)2, NH(C1-C4 alkyl), N(C1-C4 alkyl)2, O(C1-C4 alkyl), O(C1-C4 haloalkyl), NHC(O)NH(C1-C4 alkyl), NHC(O)N(C1-C4 alkyl)2, OC(O)(C1-C4 alkyl), OCO2(C1-C4 alkyl), S(O) p (C1-C4 alkyl), S(O) p (C1-C4 haloalkyl), SO2NH(C1-C4 alkyl), SO2N(C1-C4 alkyl)2, or OS(O)2(C1-C4 alkyl), OS(O)2(C1-C4 haloalkyl); or X 1is a phenyl or a 5-membered aromatic heterocycle containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen, 1 sulfur, and 1 to 3 nitrogen atoms, or a 6-membered aromatic heterocycle containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein each phenyl or 5- to 6-membered aromatic heterocycle is selected from one or more of halogen, cyano, nitro, OH, CHO, COH, CO(C1-C4 aryl), , CO2(C1-C4 alkyl), C(O)NH(C1-C4 alkyl), C(O)N(C1-C4 alkyl)2, NH(C1-C4 alkyl), N(C1-C4 alkyl)2, O(C1-C4 alkyl), O(C1-C4 haloalkyl), NHC(O)NH(C1-C4 alkyl), NHC(O)N(C1-C4 alkyl)2, OC(O)(C1-C4 alkyl), OCO2(C1-C4 alkyl), S(O) p (C1-C4 alkyl), S(O) p (C1-C4 haloalkyl), SO2NH(C1-C4 alkyl), SO2N(C1-C4 alkyl)2, or OS(O)2(C1-C4 alkyl), OS(O)2(C1-C4 haloalkyl).

[0005] The present disclosure also provides a composition comprising a compound of formula 1, an N-oxide or salt thereof, and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent. In one embodiment, the present disclosure also provides a composition for controlling invertebrate pests comprising a compound of formula 1, an N-oxide or salt thereof, and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, optionally further comprising at least one additional biologically active compound or agent.

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

[0007] The disclosure also provides a method for controlling 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.

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

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

[0010] The present disclosure also provides a method for protecting seeds from invertebrate pests, comprising contacting the seeds with a biologically effective amount of a compound of Formula 1, its N-oxide or salt, (e.g., as a composition described herein). The present disclosure also relates to treated seeds (i.e., seeds contacted with a compound of Formula 1).

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

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

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

[0014] The transitional phrase "consisting of" excludes any unspecified element, step, or ingredient. In the case of a claim, such would close the claim to the inclusion of materials other than those recited, apart from impurities ordinarily associated therewith. When the phrase "consisting of" appears in a clause in the body of a claim rather than immediately following a preamble, it limits only the elements set forth in that clause; other elements are not excluded from the claim as a whole.

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

[0016] It should be readily understood that where the applicant has defined an embodiment or portion thereof with open-ended terms such as, for example, "comprising," the description should be construed as also describing such embodiments using the terms "consisting essentially of" or "consisting of" (unless stated to the contrary).

[0017] Further, unless expressly stated to the contrary, "or" refers to an inclusive "or" and not an exclusive "or." For example, a condition "A or B" is satisfied by any one of the following: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), and both A and B are true (or exist).

[0018] Furthermore, the indefinite articles "a" and "an" preceding an element or component of the present disclosure are intended to be open ended with regard to the number of instances (i.e., occurrences) of that element or component. Thus, "a" or "an" should be read to include one or at least one, and the singular form of that element or component also includes the plural, unless it is clear that the number is intended to be singular.

[0019] As referred to in this disclosure, the term "invertebrate pests" includes arthropods, gastropods, nematodes and helminth parasites that are economically important as pests. The term "arthropods" includes insects, mites, spiders, scorpions, centipedes, millipedes, pillbugs and symphylans. The term "gastropods" includes snails, slugs and other Stylommatophora. The term "nematodes" includes members of the phylum Nematoda, e.g., phytophagous nematodes and helminth parasites. The term "parasitic helminths" includes all parasites, such as roundworms (Nematoda), heartworms (Nematoda, Secernentea), trematodes (Platyhelminthes, Tematoda), hookworms (Acanthocephala), and tapeworms (Platyhelminthes, Cestoda).

[0020] For purposes of this disclosure, "invertebrate pest control" means the inhibition of invertebrate pest development (including mortality, reduced feeding, and / or mating disruption), and related expressions are similarly defined.

[0021] The term "agronomic" refers to the production of agricultural crops such as food and fiber, and includes the growing of corn or corn, soybeans and other legumes, rice, grains (e.g., wheat, oats, barley, rye and rice), leafy vegetables (e.g., lettuce, cabbage and other greens), fruit vegetables (e.g., tomatoes, peppers, eggplant, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, fruit trees (e.g., pome fruits, stone fruits and citrus fruits), small fruit trees (e.g., berries and cherries) and other specialty crops (e.g., canola, sunflowers and olives).

[0022] The term "non-agricultural" refers to non-crop crops such as horticultural crops (e.g., greenhouse, nursery or ornamental plants not grown in a field), residential, agricultural, commercial and industrial structures, turf (e.g., turf farms, pastures, golf courses, lawns, athletic fields, etc.), wood products, storage products, silviculture and vegetation management, public health (i.e., humans) and animal health (e.g., domesticated animals, non-domesticated animals such as pets, livestock and poultry, wildlife) uses.

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

[0024] The term "biologically effective amount" refers to an amount of a bioactive compound (e.g., a compound of Formula 1) sufficient to produce a desired biological effect upon application (i.e., contact) to the invertebrate pest to be controlled or its environment or to the plant, seed or locus of the plant in which the plant grows (e.g., growth medium) for protecting the plant from damage by the invertebrate pest or for other desired effect (e.g., increased plant vigor).

[0025] Nonagronomic applications include protecting animals from invertebrate parasitic pests by administering a parasitically effective (i.e., biologically effective) amount of the disclosed compounds to the animal to be protected, typically in the form of a composition formulated for the animal. As referred to in this disclosure and claims, the terms "parasiticidal" and "parasitocidally" refer to an observable effect on an invertebrate parasitic pest to provide protection for the animal from the pest. A parasiticidal effect typically relates to reducing the occurrence or activity of the target invertebrate parasitic pest. Such effects on pests include necrosis, death, growth retardation, reduced motility or reduced ability to persist on or within the host animal, reduced feeding, and inhibition of reproduction. These effects on invertebrate parasitic pests provide control (including prevention, reduction, or elimination) of parasitic reproduction or infection of the animal.

[0026] A wavy line in a structural fragment indicates the point of attachment of the fragment to the remainder of the molecule. For example, if the variable Q in Formula 1 is defined as Q-1, then a wavy line bisecting the bond in Q-1 means that Q-1 is attached to the remainder of the structure of Formula 1 at that position.

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

[0028] "Alkylamino" contains an NH group substituted with a straight-chain or branched alkyl. Examples of "alkylamino" include CH3CH2NH, CH3CH2CH2NH, and (CH3)2CHNH. Examples of "dialkylamino" include (CH3)2N, (CH3CH2)2N, and CH3CH2(CH3)N. "Alkenylamine" contains an NH group substituted with a straight-chain or branched alkene. Examples of "alkenylamine" include CH2=CHNH, CH3CH=C(CH3)CH2NH, (CH3)2CHCH=CHNH, and the various butenylamine, pentenylamine, and hexenylamine isomers. "Alkynylamine" contains an NH group substituted with a straight-chain or branched alkyne. Examples of "alkynylamines" include HC≡CNH, CH3C≡CCH2NH, (CH3)2CHC≡CNH, and the various butynylamine, pentynylamine, and hexynylamine isomers.

[0029] "Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy, and the various butoxy, pentoxy, and hexyloxy isomers. "Alkoxyalkyl" denotes alkoxy substitution on alkyl. Examples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2OCH2, and CH3CH2OCH2CH2.

[0030] "Alkylthio" includes branched or straight chain alkylthio residues, such as methylthio, ethylthio, and the various propylthio, butylthio, pentylthio, and hexylthio isomers. "Alkylsulfinyl" includes both enantiomers of alkylsulfinyl groups. Examples of "alkylsulfinyl" include CH3S(O)-, CH3CH2S(O)-, CH3CH2CH2S(O)-, (CH3)2CHS(O)-, and the various butylsulfinyl, pentylsulfinyl, and hexylsulfinyl isomers. Examples of "alkylsulfonyl" include CH3S(O)2-, CH3CH2S(O)2-, CH3CH2CH2S(O)2-, (CH3)2CHS(O)2-, and the various butylsulfonyl, pentylsulfonyl, and hexylsulfonyl isomers. "Alkylthioalkyl" denotes an alkylthio substitution on an alkyl. Examples of "alkylthioalkyl" include CH3SCH2, CH3SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and CH3CH2SCH2CH2.

[0031] "Alkylcarbonyl" means a straight or branched alkyl moiety attached to a C(=O) moiety. Examples of "alkylcarbonyl" include CH3C(=O)-, CH3CH2CH2C(=O)-, and (CH3)2CHC(=O)-. Examples of "alkoxycarbonyl" include CH3OC(=O)-, CH3CH2OC(=O)-, CH3CH2CH2OC(=O)-, (CH3)2CHOC(=O)-, as well as the various butoxycarbonyl, pentoxycarbonyl, and hexoxycarbonyl isomers.

[0032] The term "alkylaminocarbonyl" refers to a straight or branched chain alkylamino bonded to and linked through a C(=O) group. Examples of "alkylaminocarbonyl" include CHNHC(=O), CHCHNHC(=O), CHCHCHNHC(=O) and (CH)CHNHC(=O). Examples of "dialkylaminocarbonyl" include (CH)NC(=O), (CHCH)NC(=O), CHCH(CH)NC(=O) and (CH)CH(CH)NC(=O). The term "alkenylaminocarbonyl" refers to a straight or branched chain alkenylamino bonded to and linked through a C(=O) group. Examples of "alkenylaminocarbonyl" include CH2=CHNHC(=O), CH3CH=C(CH3)CH2NHC(=O) and (CH3)2CHCH=CHNHC(=O). The term "alkynylaminocarbonyl" refers to a straight or branched alkynylamino bonded to and linked through a C(=O) group. Examples of "alkynylaminocarbonyl" include HC≡CNHC(=O), CH3CH≡CCH2NHC(=O) and (CH3)2CHC≡CNHC(=O).

[0033] "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The term "alkylcycloalkyl" denotes alkyl substitution on a cycloalkyl residue, including, for example, ethylcyclopropyl, i-propylcyclobutyl, 3-methylcyclopentyl, and 4-methylcyclohexyl. The term "cycloalkylalkyl" denotes cycloalkyl substitution on an alkyl moiety. Examples of "cycloalkylalkyl" include cyclopropylmethyl, cyclopentylethyl, cyclohexylmethyl, and other cycloalkyl moieties attached to straight-chain or branched alkyl groups. The term "cycloalkoxy" denotes a cycloalkyl attached through an oxygen atom, such as cyclopentyloxy and cyclohexyloxy. "Cycloalkylamino" denotes an NH group substituted with a cycloalkyl. Examples of "cycloalkylamino" include cyclopropylamino and cyclohexylamino. "Cycloalkylaminocarbonyl" denotes a cycloalkylamino attached to a C(=O) group, including, for example, cyclopentylaminocarbonyl and cyclohexylaminocarbonyl.

[0034] The term "halogen", when used alone or in compound terms such as "haloalkyl" or in descriptions such as "alkyl substituted with halogen", includes fluorine, chlorine, bromine or iodine. Furthermore, when used in compound terms such as "haloalkyl" or in descriptions such as "alkyl substituted with halogen", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of "haloalkyl" or "alkyl substituted with halogen" are F3C-, ClCH2-, CF3CH 2-and CF3CCl2-. The terms "halocycloalkyl", "haloalkoxy", "haloalkylthio", "haloalkylcarbonyl", "haloalkoxycarbonyl", "haloalkylaminocarbonyl", "halodialkylaminocarbonyl" and the like are defined analogously to the term "haloalkyl". Examples of "haloalkoxy" include CF3O-, CCl3CHO-, HCF2CH2CH2O-, and CF3CHO-. 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-.

[0035] The chemical abbreviations S(O) and S(=O) used herein represent a sulfinyl moiety. The chemical abbreviations SO2, S(O)2, and S(=O)2 used herein represent a sulfonyl moiety. The chemical abbreviations C(O) and C(=O) used herein represent a carbonyl moiety. The chemical abbreviations C(S) and C(=S) used herein represent a thiocarbonyl moiety. The chemical abbreviations CO2, C(O)O, and C(=O)O used herein represent an oxycarbonyl moiety. "CHO" means formyl.

[0036] "Oxiranylalkyl" refers to an oxirane substitution on a straight or branched alkyl group. Examples of "oxiranylalkyl" include, but are not limited to, the following: [ka]

[0037] "Oxetanylalkyl" refers to an oxetane substitution on a straight or branched alkyl group. Examples of "oxetanylalkyl" include, but are not limited to, the following: [ka]

[0038] "Thietanylalkyl" denotes a thietane substitution on a straight or branched alkyl group. Examples of "thietanylalkyl" include, but are not limited to, the following: [ka]

[0039] The total number of carbon atoms in the substituent is "C i ~C j " where i and j are numbers from 1 to 9. For example, C1-C4 alkylsulfonyl refers to methylsulfonyl to butylsulfonyl; C2 alkoxyalkyl refers to CH3OCH2-; C3 alkoxyalkyl refers to, for example, CH3CH(OCH3)-, CH3OCH2CH2-, or CH3CHOCH2-; C4 alkoxyalkyl refers to the various isomers of an alkyl group substituted with an alkoxy group containing a total of 4 carbon atoms, examples of which include CH3CH2CH2OCH2-, and CH3CHOCH2CH2-.

[0040] When a compound is substituted with a substituent bearing a subscript indicating that the number of said substituents can be more than one, said substituents (if they are more than one) can be independently selected from a defined group of substituents, e.g., ([(R 3 ) m ], m is selected from 0, 1, or 2. A group may have a substituent that can be hydrogen, such as (R 2 or R 12 ), i.e., when the substituent is considered to be hydrogen, it is recognized that this is equivalent to the group being unsubstituted. When a variable group is shown to be optionally attached at a position, for example, m can be 0 (R 3 ) mi.e., a hydrogen can be at a position even if it is not recited in the definition of a variable. When one or more positions on a group are described as "unsubstituted" or "unsubstituted," a hydrogen atom is bonded to occupy any free valence.

[0041] Unless otherwise specified, a "ring" or "ring system" (e.g., Q) as a component of Formula 1 1 ) is carbocyclic or heterocyclic. The term "ring system" refers to two or more fused 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 "spiro-bicyclic". An "ortho-fused bicyclic ring system" refers to a ring system in which the two constituent rings have two adjacent atoms in common. A "bridged bicyclic ring system" is formed by bonding one or more segments of atoms to non-adjacent ring members of a ring. A "spiro-bicyclic ring system" is formed by bonding two or more segments of atoms to the same ring member of a ring. The term "fused heterobicyclic ring system" refers to a fused bicyclic ring system in which at least one ring atom is not carbon. The term "ring member" refers to atoms or other moieties (e.g., C(=O), C(=S), S(O) or S(O)2) that form the backbone of a ring or ring system.

[0042] The term "carbocyclic ring", "carbocycle" or "carbocyclic ring system" refers to a ring or ring system in which the atoms forming the ring backbone are selected from carbon only. The term "heterocyclic ring", "heterocycle" or "heterocyclic ring system" refers to a ring or ring system in which at least one atom forming the ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur. Typically, a heterocyclic ring contains up to four nitrogens, up to two oxygens and up to two sulfurs. Unless otherwise specified, a carbocyclic or heterocyclic ring may be a saturated or unsaturated ring. "Saturated" refers to a ring having a backbone made of carbon atoms connected together by single bonds, and the remaining valences are occupied by hydrogen atoms, unless otherwise specified. Unless otherwise specified, an "unsaturated ring" may be partially unsaturated or fully unsaturated. The expression "fully unsaturated ring" refers to a ring of atoms in which the bonds between atoms in the ring are single or double bonds according to valence bond law, and further, the bonds between atoms in the ring include as many double bonds as possible without overlapping double bonds (i.e., without C=C=C or C=C=N). The term "partially unsaturated ring" refers to a ring that includes at least one ring member that is bonded to an adjacent ring member via a double bond, and that conceptually potentially accommodates several non-overlapping double bonds between adjacent ring members (i.e., in its fully unsaturated corresponding form) beyond the number of double bonds that exist (i.e., in its partially unsaturated form).

[0043] Unless otherwise specified, heterocycles and ring systems may be attached by any available carbon or nitrogen by replacement of a hydrogen on the carbon or nitrogen.

[0044] "Aromatic" indicates that each ring atom is essentially coplanar, has p orbitals perpendicular to the plane of the ring, and has (4n+2) pi electrons associated with the ring according to Huckel's rule, where n is a positive integer. The term "aromatic ring system" refers to a carbocyclic or heterocyclic ring system in which at least one ring of the ring system is aromatic. When a fully unsaturated carbocyclic ring satisfies the Huckel's rule, said ring is also referred to as an "aromatic ring" or aromatic carbocyclic ring. The term "aromatic carbocyclic ring system" refers to 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, said ring is also called an "aromatic heterocycle" or aromatic heterocyclic ring. The term "aromatic heterocyclic ring system" refers to a heterocyclic ring system in which at least one ring of the ring system is aromatic. The term "non-aromatic ring system" refers to a carbocyclic or heterocyclic ring system that may be fully saturated and / or fully unsaturated, provided that none of the rings of the ring system are aromatic. The term "non-aromatic carbocyclic ring system" refers to a carbocyclic ring in which none of the rings in the ring system are aromatic. The term "non-aromatic heterocyclic ring system" refers to a heterocyclic ring system in which none of the rings in the ring system are aromatic.

[0045] The term "optionally substituted" in relation to a heterocyclic ring refers to a group that is unsubstituted or has at least one non-hydrogen substituent that does not destroy the biological activity retained by the unsubstituted analog. As used herein, the following definitions shall apply unless otherwise specified. The term "optionally substituted" is used synonymously with the phrase "substituted or unsubstituted" or the term "(un)substituted". Unless otherwise specified, an optionally substituted group may have a substituent at each substitutable position of the group, and each substitution is independent of each other.

[0046] For example, R 1 When a substituent such as R is a 5- or 6-membered nitrogen-containing heterocyclic ring, it may be attached to the remainder of Formula 1 through any available carbon or nitrogen ring atom, unless otherwise noted. 1 may be (among others) phenyl optionally substituted with 1 to 3 substituents selected from the group of substituents defined in the Summary. An example of a phenyl optionally substituted with 1 to 3 substituents is the ring shown as U-1 in Exhibit 1, where R v But R 1 About X as defined in the overview 1 and r is an integer from 0 to 5.

[0047] As mentioned above, R 1 may be (among other things) a 5- or 6-membered heterocyclic ring which may be saturated or unsaturated and optionally substituted with one or more substituents selected from the group of substituents defined in the Summary. Examples of 5- or 6-membered unsaturated aromatic heterocyclic rings optionally substituted with one or more substituents are R v But R 1 and r is an integer from 0 to 4, including rings U-2 to U-61 shown in Exhibit 1, limited by the number of available positions for each U group. U-29, U-30, U-36, U-37, U-38, U-39, U-40, U-41, U-42, and U-43 have only one available position, and for these U groups, r is limited to the integer 0 or 1, with r being 0 meaning that the U group is unsubstituted and hydrogen is (R v ) r This means that the molecule is present at the position indicated by [ka] [ka] [ka]

[0048] For example, R 1 Substituents such as R 1 It should be noted that in the case of a 5- or 6-membered saturated or unsaturated non-aromatic heterocycle optionally substituted with one or more substituents selected from the group of substituents defined in the Summary for, one or two carbon ring members of the heterocycle may optionally be in the oxidized form of a carbonyl moiety.

[0049] Examples of 5- or 6-membered saturated or non-aromatic unsaturated heterocycles include rings T-1 to T-35 shown in Exhibit 2. Note that when the attachment point on the T group is shown as floating, the T group can be attached to the remainder of Formula 1 through any available carbon or nitrogen of the T group by replacement of a hydrogen atom.v can be attached to any available carbon or nitrogen by replacing a hydrogen atom. For these T rings, r is typically an integer from 0 to 4, limited by the number of available positions on each T group.

[0050] A wide variety of synthetic methods are known in the art that allow the preparation of aromatic and non-aromatic heterocyclic rings and ring systems. For detailed reviews, see the following publications: Comprehensive Heterocyclic Chemistry (A.R.Katritzky and C.W.Rees editors-in-chief, Pergamon Press, Oxford, 1984), an 8-volume set; and Comprehensive Heterocyclic Chemistry II (A.R.Katritzky, C.W.Rees, and E.F.V.Scriven editors-in-chief, Pergamon Press, Oxford, 1996), a 12-volume set.

[0051] The compounds of the present disclosure can exist as one or more stereoisomers. Stereoisomers are isomers that have the same constitution but differ in the spatial arrangement of their atoms, including enantiomers, diastereomers, cis-trans isomers (also called geometric isomers), and atropisomers. Atropisomers result from restricted rotation around a single bond, and because of the high barrier to rotation, it is possible to isolate these isomeric species. As will be appreciated by those skilled in the art, one stereoisomer may be more reactive and / or may exhibit advantageous effects when enriched or separated from other stereoisomers. Furthermore, those skilled in the art will recognize methods for separating, enriching, and / or selectively preparing said stereoisomers. For a comprehensive description of all aspects of stereoisomerism, please refer to the following reference: Ernest L. Eliel and Samuel H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, 1994.

[0052] The compounds of the present disclosure can exist as a mixture of stereoisomers or as individual stereoisomers. For example, the two possible enantiomers of Formula 1 are depicted as Formula 1' and Formula 1", which are identified by an asterisk (*) along with R 4 The compound of formula 1' contains an asymmetric center identified as a center having R 4 and the compound of formula 1" refers to the (-) enantiomer at the center having R 4 It refers to the (+) enantiomer at the center having [ka]

[0053] The depictions of molecules drawn herein follow standard conventions for showing stereochemistry. To show three-dimensional configuration, bonds rising out of the plane of the drawing, toward the viewer, are represented as solid wedges with the wider end of the wedge attached to an atom rising out of the plane of the drawing, toward the viewer. Bonds going down the plane, away from the viewer, are represented as dashed wedges with the narrower end of the wedge attached to an atom going further away from the viewer.

[0054] The present disclosure includes racemic mixtures, e.g., containing equal amounts of the enantiomers of formula 1' and 1". Additionally, the present disclosure includes compounds enriched in the enantiomers of formula 1 as compared to racemic mixtures. Substantially pure enantiomers of compounds of formula 1, e.g., formula 1' and formula 1", are also included.

[0055] When enantiomerically enriched, one enantiomer is present in greater amount than the other, and the degree of enrichment can be defined in terms of enantiomeric excess ("ee"), which is defined as (2x-1)·100%, where x is the molar fraction of the more abundant enantiomer in the mixture (e.g., 20% "ee" corresponds to a 60:40 enantiomeric ratio). The compositions of the present disclosure preferably have an enantiomeric excess of the more active isomer of at least 50%; more preferably an enantiomeric excess of at least 75%; even more preferably an enantiomeric excess of at least 90%; and most preferably an enantiomeric excess of at least 94%. Of particular note are enantiomerically pure embodiments of the more active isomer. The present disclosure includes, for example, racemic mixtures containing equal amounts of the enantiomers of formula 1' and 1". Additionally, the present disclosure includes mixtures enriched in the enantiomer of formula 1' as compared to racemic mixtures of formula 1' and 1". The present disclosure also includes substantially pure enantiomers of formula 1'.

[0056] One embodiment of the present disclosure is one in which the 1' to 1" ratio is at least 75:25 (1 i The compound of formula 1 includes a mixture of stereoisomers of the compounds of formula 1' and formula 1" which are 50% enantiomeric excess of the compound of formula 1'.

[0057] One embodiment of the present disclosure includes a mixture of stereoisomers of compounds of formula 1' and formula 1" in a ratio of 1' to 1" of at least 90:10 (80% enantiomeric excess of 1').

[0058] One embodiment of the present disclosure includes a mixture of stereoisomers of compounds of formula 1' and formula 1" in a ratio of 1' to 1" of at least 95:5 (90% enantiomeric excess of 1').

[0059] One embodiment of the present disclosure includes a mixture of stereoisomers of compounds of formula 1' and formula 1" in a ratio of 1' to 1" of at least 98:2 (96% enantiomeric excess of 1').

[0060] One embodiment of the present disclosure includes a mixture of stereoisomers of compounds of formula 1' and formula 1" in a ratio of 1' to 1" of at least 99:1 (98% enantiomeric excess of 1').

[0061] One embodiment of the present disclosure includes a mixture of stereoisomers of compounds of formula 1' and formula 1" in a 1' to 1" ratio that is substantially 100:0.

[0062] One embodiment of the present disclosure is a compound represented by formula 1 i This includes compounds of the formula:

[0063] Additionally, the present disclosure provides a compound of formula 1 compared to a racemic mixture of formulas 1″ and 1′. ii Enantiomerically enriched mixtures are included. The present disclosure also includes substantially pure enantiomers of Formula 1".

[0064] One embodiment of the disclosure includes a mixture of stereoisomers of compounds of formula 1″ and formula 1′, where the ratio of 1″ to 1′ is at least 75:25 (50% enantiomeric excess of 1″).

[0065] The 1” to 1’ ratio must be at least 90:10 (1 ii One embodiment of the present disclosure includes a mixture of stereoisomers of compounds of Formula 1″ and Formula 1′, which is 80% enantiomeric excess of the compound of Formula 1″.

[0066] 1” to 1 i is at least 95:5 (90% enantiomeric excess of 1″). One embodiment of the disclosure includes a mixture of stereoisomers of compounds of formula 1″ and formula 1′.

[0067] One embodiment of the disclosure includes a mixture of stereoisomers of compounds of formula 1″ and formula 1′, where the ratio of 1″ to 1′ is at least 98:2 (96% enantiomeric excess of 1″).

[0068] One embodiment of the disclosure includes a mixture of stereoisomers of compounds of formula 1″ and formula 1′, where the ratio of 1″ to 1′ is at least 99:1 (98% enantiomeric excess of 1″).

[0069] One embodiment of the present disclosure comprises a mixture of stereoisomers of compounds of formula 1" and formula 1', where the ratio of 1" to 1' is substantially 100:0.

[0070] One embodiment of the present disclosure includes a compound of formula 1″.

[0071] Those skilled in the art will understand that not all nitrogen-containing heterocycles can form N-oxides because the 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 the oxidation of heterocycles and tertiary amines using peroxyacids such as peracetic acid and 3-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane. These methods for preparing N-oxides have been widely described and reviewed in the literature, see for example the following references: T.L. Gilchrist, Comprehensive Organic Synthesis, vol. 7, pp 748-750 (SV Ley, Ed., Pergamon Press); M. Tisler and B. Stanovnik, Comprehensive Heterocyclic Chemistry, vol. 3, pp. 18-20, A.J. Boulton and A.McKillop, Eds., Pergamon Press; M.R. Grimmett and B.R.T. Keene, Advances in Heterocyclic Chemistry, vol. 43, pp. 149-161, A.R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik, Advances in Heterocyclic Chemistry, vol. 9, pp. 285-291, A.R. Katritzky and A.J. Boulton, Eds., Academic Press. Press; and GWHCheeseman and ESGWerstiuk, Advances in Heterocyclic Chemistry, vol. 22, pp. 390-392, ARKatritzky and AJ Boulton, Eds., Academic Press.

[0072] Those skilled in the art recognize that salts of compounds share biological utility with their non-salt forms because they are in equilibrium with their corresponding non-salt forms in the environment and under physiological conditions. Thus, a wide variety of salts of compounds of formula 1 are useful for controlling invertebrate pests. Salts of compounds of formula 1 include acid addition salts with inorganic or organic acids such as hydrobromic acid, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, acetic acid, butyric acid, fumaric acid, lactic acid, maleic acid, malonic acid, oxalic acid, propionic acid, salicylic acid, tartaric acid, 4-toluenesulfonic acid, or valeric acid. When compounds of formula 1 contain an acidic moiety such as a carboxylic acid or phenol, salts also include those formed with organic or inorganic bases such as pyridine, triethylamine, or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium, or barium. Thus, the present disclosure includes compounds selected from formula 1, their N-oxides, and suitable salts.

[0073] Compounds selected from Formula 1, their stereoisomers, tautomers, N-oxides and salts typically exist in more than one form, and thus Formula 1 includes all crystalline and amorphous forms of the compounds represented by Formula 1. Amorphous forms include solid embodiments, such as waxes and gums, as well as liquid embodiments, such as solutions and melts. Crystalline forms include embodiments that represent a substantially single crystal type and embodiments that represent a mixture of polymorphs (i.e., multiple crystalline types). The term "polymorph" refers to a particular crystalline form of a compound that can crystallize in various crystalline forms, these forms having different molecular arrangements and / or conformations in the crystal lattice. Multiple polymorphs can have the same chemical composition, but they can also differ in composition due to the presence or absence of co-crystallized water or other molecules that can be weakly or strongly bound in the lattice. Polymorphs can differ in terms of chemical, physical and biological properties, such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspendability, dissolution rate and bioavailability. Those skilled in the art will understand that a particular polymorph of the compound represented by formula 1 may exhibit advantageous effects (e.g., suitability in preparing useful formulations, improved biological performance) compared to other polymorphs or mixtures of polymorphs of the same compound represented by formula 1. Preparation and isolation of a particular polymorph of the compound represented by formula 1 can be achieved by methods known to those skilled in the art, such as, for example, crystallization using a selected solvent and temperature. Compounds of the present disclosure may exist as one or more crystalline polymorphs. The present disclosure includes both individual polymorphs and mixtures of polymorphs, including mixtures enriched in one polymorph relative to other polymorphs. For a comprehensive description of polymorphs, see R. Hilfiker, Ed., Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006.

[0074] Embodiments of the present disclosure described in the Summary include those described below. In the following embodiments, Formula 1 includes its stereoisomers, N-oxides and salts, and references to "compounds of Formula 1" include the definitions of the substituents defined in the Summary, unless further defined in the embodiments.

[0075] Embodiment 1. A compound of formula 1, wherein R 1 is C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl, where each alkyl, alkenyl, or alkynyl is selected from one or more R 6 or R 1 However, 1 to 3 R 6 or R 1 But there is one or more R 6 is a pyrimidine optionally substituted with

[0076] Embodiment 1a. R1 is C1-C6 alkyl or C2-C6 alkenyl, where each alkyl or alkenyl is selected from one or more R 6 The compound of formula 1 as described in embodiment 1, substituted with

[0077] Embodiment 1b.R 1 is C1-C6 alkyl, where each C1-C6 alkyl is selected from one or more R 6 A compound of formula 1 according to any of the above embodiments, substituted with:

[0078] Embodiment 1c.R 1 is C1-C4 alkyl, where each C1-C4 alkyl is selected from the group consisting of one or more of halogen, cyano, nitro, C3-C6 cycloalkylalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C 4 Compounds of formula 1 according to any of the above embodiments substituted with haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C1-C4 alkylsulfonate or C1-C4 haloalkylsulfonate.

[0079] Embodiment 1d.R 1is phenyl optionally substituted with one to three halogen, cyano, nitro, C3-C6 cycloalkylalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl or C1-C4 haloalkylsulfonyl.

[0080] Embodiment 1d.R 1 A compound of formula 1 according to any of the above embodiments, wherein is C1-C4 alkyl, where each C1-C4 alkyl is substituted with one or more halogens.

[0081] Embodiment 1e.R 1 A compound of formula 1 according to any one of the above embodiments, wherein is CH2 substituted with F, Cl, OCH3, CN, CO2CH3.

[0082] Embodiment 1f.R 1 The compound of formula 1 according to any one of embodiments 1 to 1d, wherein is CF3, CHF2, or CH2F.

[0083] Embodiment 1f.R 1 The compound of Formula 1 as described in any one of embodiments 1 to 1d or 1f, wherein is CF3.

[0084] Embodiment 1g.R 1 A compound of formula 1 according to any of the above embodiments, wherein is phenyl optionally substituted with phenyl optionally substituted with 1-3 halogen, cyano, CF3, OCH3 or OCF3.

[0085] Embodiment 1h. A compound of Formula 1 as in any of the previous embodiments which is phenyl optionally substituted with CH3, F, Cl, Br, OCH3, CN, NO2, CF3, or OCF3.

[0086] Embodiment 1i.R 1 A compound of formula 1 according to any of the above embodiments, wherein is pyrimidine optionally substituted with 1 to 3 halogen, cyano, CF3, OCH3 or OCF3.

[0087] Embodiment 1j.R 1 A compound of formula 1 according to any of the above embodiments, wherein is pyrimidine optionally substituted with CH3, F, Cl, Br, OCH3, CN, NO2, CF3, or OCF3.

[0088] Embodiment 2.R 2 is hydrogen, halogen, cyano, nitro; or R 2 is C1-C6 alkyl, where each C1-C6 alkyl is selected from one or more R 6 optionally substituted with; or R 2 But, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , OR 7 , S(O) p R 7 , SO2NR 7 R 8 , or OS(O)2R 9 The compound of formula 1 according to any of the above embodiments,

[0089] Embodiment 2a.R 2is halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl or C1-C4 haloalkylsulfonyl.

[0090] Embodiment 2b.R 2 The compound of formula 1 according to any one of any of the above embodiments, wherein is halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy.

[0091] Embodiment 2c.R 2 The compound of formula 1 according to any one of any of the above embodiments, wherein is H, F, Cl, Br, cyano, CF3, or OCF3.

[0092] Embodiment 2d.R 2 A compound of formula 1 according to any of the above embodiments, wherein is in the meta position.

[0093] Embodiment 3.R 3 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C6 cycloalkyl, where each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more R 6 A compound of formula 1 according to any of the above embodiments, optionally substituted with

[0094] Embodiment 3a.R 3 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 alkylcycloalkyl, where each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more R 6A compound of formula 1 according to any of the above embodiments, optionally substituted with

[0095] Embodiment 3b.R 3 The compound of formula 1 according to any of the above embodiments, wherein is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 alkylcycloalkyl.

[0096] Embodiment 3c.R 3 The compound of formula 1 according to any of the above embodiments, wherein is H, C1-C4 alkyl, C2-C6 alkylcycloalkyl.

[0097] Embodiment 3d.R 3 A compound of formula 1 according to any of the above embodiments, wherein is H.

[0098] Embodiment 4.R 4 is H or one or more R 6 The compound of formula 1 according to any of the above embodiments, wherein R is C1-C6 alkyl optionally substituted with R.

[0099] Embodiment 4a.R 4 The compound of Formula 1 according to any one of embodiments 1 to 3d, wherein is C1-C6 alkyl or C3-C6 cycloalkyl.

[0100] Embodiment 4b.R 4 The compound of formula 1 according to any one of the above embodiments, wherein is C1-C3 alkyl.

[0101] Embodiment 4c.R 4 A compound of formula 1 according to any one of the above embodiments, wherein is Me.

[0102] Embodiment 4d.R 4 A compound of formula 1 according to any one of the above embodiments, wherein is H.

[0103] Embodiment 5.R 5A compound of formula 1 according to any of the above embodiments, wherein is H.

[0104] Embodiment 6.R 6 is C1-C6 alkyl or C3-C7 cycloalkyl, where each alkyl or cycloalkyl is optionally substituted with one or more substituents selected from halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, or C1-C4 haloalkylsulfonyl.

[0105] Embodiment 6a.R 6 is C1-C6 alkyl or C3-C7 cycloalkyl, where each alkyl or cycloalkyl is optionally substituted with one or more substituents selected from halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, or C1-C4 alkylsulfonyl.

[0106] Embodiment 6b.R 6is C1-C6 alkyl, where each alkyl is optionally substituted with one or more substituents selected from halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, or C1-C4 alkylsulfonyl.

[0107] Embodiment 6b.R 6 Compounds of formula 1 according to any of embodiments 1-6a, wherein is cycloalkyl optionally substituted with one or more substituents selected from halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, or C1-C4 alkylsulfonyl.

[0108] Embodiment 7.A 1 and A 2 is halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , OR 7, NHC(O)NR 7 R 8 , O.C.(O)R 7 , O.C.(O)O.R. 7 , S(O)pR 7 , SO2NR 7 R 8 , or OS(O)2R 9 is a pyridine, pyrimidine, pyrazine or pyridazine optionally substituted with R 10 , R 11 and R 12 is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl or C1-C4 haloalkylsulfonyl.

[0109] Embodiment 7a.A 1 and A 2 is pyridine, pyrimidine, pyrazine, pyridazine, or thiazole optionally substituted with halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, or C1-C4 haloalkylsulfonyl; R 10 , R 11 and R 12is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl or C1-C4 haloalkylsulfonyl.

[0110] Embodiment 7b.A 1 and A 2 is pyridine or pyrimidine optionally substituted with halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 10 , R 11 and R 12 A compound of formula 1 according to any one of the above embodiments, wherein is hydrogen.

[0111] In embodiment 7c.Q is Q 1 The compound of formula 1 according to any one of the above embodiments,

[0112] Embodiment 7d.Q is Q 2 The compound of formula 1 according to any one of the above embodiments,

[0113] Embodiment 7e.A 1 The compound of Formula 1 according to any of embodiments 1-5c, wherein is pyridine, pyrimidine, pyrazine, pyridazine, or thiazole.

[0114] Embodiment 7f. A compound of formula 1 according to any one of embodiments 1 to 5c and 5e, wherein A1 is pyridine or pyrimidine.

[0115] Embodiment 7g.A 1 The compound of Formula 1 according to any one of embodiments 1-5c and 5e-5f, wherein is pyridine.

[0116] Embodiment 7h.A 1 A compound of Formula 1 according to any one of embodiments 1-5c and 5e-5f, wherein is pyrimidine.

[0117] Embodiment 7i.A 2 The compound of Formula 1 according to any of embodiments 1-5c, wherein is pyridine, pyrimidine, pyrazine, pyridazine, or thiazole.

[0118] Embodiment 7j.A 2 A compound of Formula 1 according to any one of embodiments 1 to 5c and 5i, wherein is pyridine or pyrimidine.

[0119] Embodiment 7k.A 2 The compound of Formula 1 according to any one of embodiments 1-5c and 5i-5j, wherein is pyridine.

[0120] Embodiment 7l.A 2 The compound of Formula 1 according to any one of embodiments 1-5c and 5i-5k, wherein is pyrimidine.

[0121] Embodiment 8. A compound of formula 1 according to any of the above embodiments, wherein the compound of formula 1 is a compound of formula 1'.

[0122] Embodiment 8a. The compound of formula 1 according to any one of embodiments 1-71, wherein the compound of formula 1 is a compound of formula 1″.

[0123] Embodiment S1. The compound of any one of embodiments 1 to 8a, wherein the compound of formula 1 is a compound of formula 1′.

[0124] Embodiment S2. The compound of any one of embodiments 1 to 8a, wherein the compound of formula 1 is a compound of formula 1″.

[0125] Embodiment S3. A composition consisting of a compound of Formula 1' and a compound of Formula 1", wherein the ratio of the compound of Formula 1' to the compound of Formula 1" is greater than 60:40.

[0126] Embodiment S3a. The composition of embodiment S3, wherein the ratio of the compound of formula 1' to the compound of formula 1" is greater than 80:20.

[0127] Embodiment S3b. The composition of embodiment S3, wherein the ratio of the compound of Formula 1' to the compound of Formula 1" is greater than 90:10.

[0128] Embodiment S3c. The composition of embodiment S3, wherein the ratio of the compound of formula 1' to the compound of formula 1" is greater than 99:1.

[0129] Embodiment S4. A composition consisting of a compound of Formula 1" and a compound of Formula 1', wherein the ratio of the compound of Formula 1" to the compound of Formula 1' is greater than 60:40.

[0130] Embodiment X. A method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula 1.

[0131] Embodiment X1. The method of claim X, wherein the environment is soil or plant foliage.

[0132] Embodiment X2. The method of embodiment X or X1, wherein the compound of formula 1 is a compound of formula 1'.

[0133] Embodiment X2. The method of embodiment X or X1, wherein the compound of formula 1 is a compound of formula 1".

[0134] The embodiments of the present disclosure, including the above embodiments 1-X2 and any other embodiments described herein, may be combined in any manner, and the explanations of the variables of the embodiments relate not only to compounds of formula 1, but also to starting compounds and intermediate compounds useful for preparing compounds of formula 1. Additionally, the embodiments of the present disclosure, including the above embodiments 1-X2 and any other embodiments described herein, and any combination thereof, relate to the compositions and methods of the present disclosure.

[0135] Combinations of embodiments A1-C are exemplified by the following:

[0136] Embodiment A1. A compound of formula 1, wherein R 1 is C1-C6 alkyl, where each alkyl is selected from one or more R 6 or R 1 However, 1 to 3 R 6 phenyl optionally substituted with R 1 But there is one or more R 6 is a pyrimidine optionally substituted with; R 2 is hydrogen, halogen, cyano, nitro; or R 2 is C1-C6 alkyl, where each C1-C6 alkyl is selected from one or more R 6 optionally substituted with; or R 2 But, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , OR 7 , S(O) p R 7 , SO2NR 7 R 8 , or OS(O)2R 9 and; R 3 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C6 cycloalkyl, where each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more R 6 optionally replaced with; R 4 is H or one or more R 6 is a C1-C6 alkyl optionally substituted with; R 5 is hydrogen; R 6 But halogen, cyano, nitro, CN, C(O)R 7, C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , OR 7 , NHC(O)NR 7 R 8 , O.C.(O)R 7 , O.C.(O)O.R. 7 , S(O) p R 7 , SO2NR 7 R 8 , OS(O)2R 9 or R 6 is C1-C6 alkyl or C3-C7 cycloalkyl, where each alkyl or cycloalkyl is optionally substituted with one or more substituents selected from halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, or C1-C4 haloalkylsulfonyl; R 7 , R 8 and R 9 is hydrogen, C1-C4 alkyl, or C1-C4 haloalkyl; Q, [ka] and A 1 and A 2is pyridine, pyrimidine, pyrazine, pyridazine, or thiazole optionally substituted with halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, or C1-C4 haloalkylsulfonyl; R 10 , R 11 and R 12 is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl or C1-C4 haloalkylsulfonyl).

[0137] Embodiment A2. R 1 is C1-C6 alkyl, where each alkyl is selected from one or more R 6 or R 1 However, 1 to 3 R 6 is phenyl optionally substituted with; R 2 is hydrogen, halogen, cyano, nitro; or R 2 is C1-C6 alkyl, where each C1-C6 alkyl is selected from one or more R 6 optionally substituted with; or R 2 But, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R8 , OR 7 , S(O) p R 7 , SO2NR 7 R 8 , or OS(O)2R 9 and; R 3 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C6 cycloalkyl, where each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more R 6 optionally replaced with; R 4 is H or one or more R 6 is a C1-C6 alkyl optionally substituted with; R 5 is hydrogen; R 6 But halogen, cyano, nitro, CN, C(O)R 7 , C(O)OR 7 , C(O)NR 7 R 8 , N.R. 7 R 8 , OR 7 , NHC(O)NR 7 R 8 , O.C.(O)R 7 , O.C.(O)O.R. 7 , S(O) p R 7 , SO2NR 7 R 8 , OS(O)2R 9 or R 6is C1-C6 alkyl or C3-C7 cycloalkyl, where each alkyl or cycloalkyl is optionally substituted with one or more substituents selected from halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, or C1-C4 haloalkylsulfonyl; R 7 , R 8 and R 9 is hydrogen, C1-C4 alkyl, or C1-C4 haloalkyl; Q, [ka] and A 1 and A 2 is pyridine, pyrimidine, pyrazine, pyridazine, or thiazole optionally substituted with halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, or C1-C4 haloalkylsulfonyl; R 10 , R 11 and R 12Compounds of formula 1 as defined in embodiment A1, wherein is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl or C1-C4 haloalkylsulfonyl.

[0138] Embodiment A3. A compound of formula 1, wherein R 1 is C1-C4 alkyl, where each alkyl is substituted with one or more halogen, cyano, nitro, C3-C6 cycloalkylalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C1-C4 alkylsulfonate or C1-C4 haloalkylsulfonate; or R 1 is phenyl optionally substituted with 1-3 halogen, cyano, nitro, C3-C6 cycloalkylalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl or C1-C4 haloalkylsulfonyl; R 2is halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl or C1-C4 haloalkylsulfonyl; R 3 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 alkylcycloalkyl, where each alkyl, alkenyl, alkynyl, or cycloalkyl is selected from one or more R 6 optionally replaced with; R 4 is H, C1-C6 alkyl or C3-C6 cycloalkyl; R 5 is hydrogen; Q, [ka] and A 1 and A 2 is pyridine, pyrimidine, pyrazine, pyridazine, or thiazole optionally substituted with halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, or C1-C4 haloalkylsulfonyl; R 10 , R 11 and R 12is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl or C1-C4 haloalkylsulfonyl).

[0139] Embodiment A4. A compound of formula 1, wherein R 1 is CF3 or phenyl optionally substituted with 1-3 halogen, cyano, CF3, OCH3, or OCF3; R 2 is halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; R 3 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 alkylcycloalkyl; R 4 is C1-C3 alkyl; R 5 is hydrogen; Q, [ka] and A 1 and A 2 is pyridine or pyrimidine optionally substituted with halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; R 10 , R 11 and R 12 is hydrogen).

[0140] Embodiment B. A compound according to any one of embodiments A through A3, wherein the compound of formula 1 is formula 1'.

[0141] Embodiment C. The compound of any one of Embodiments A through A3, wherein the compound of Formula 1 is Formula 1″.

[0142] Certain embodiments of the present disclosure include a compound selected from the group consisting of those shown in Table 1.

[0143] [Table 1]

[0144] [Table 2]

[0145] [Table 3]

[0146] [Table 4]

[0147] [Table 5]

[0148] [Table 6]

[0149] Embodiment Y1. A composition comprising a compound of Formula 1 as described in any one of the above embodiments and at least one additional component selected from the group consisting of surfactants, solid diluents, and liquid diluents, optionally further comprising at least one additional biologically active compound or agent.

[0150] Embodiment Y2. The at least one further biologically active compound or agent is abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, afidopiropen, amidoflumet, amitraz, avermectin, azadirachtin, azinphos-methyl, benfuracarb, bensultap, bifenthrin, bifenazate, bistrifluron, borate, bromantraniliprole, buprofezin, carbaryl, carbofuran, cartap, carsol, chlorantraniliprole, chlorfenapyr, chlorfluazuron. , Chlorpyrifos, Chlorpyrifos-methyl, Chromafenozide, Clofentezine, Clothianidin, Cyantraniliprole, Cyclaniliprole, Cycloprothrin, Cycloxapride, Cyflumetofen, Cyfluthrin, Beta-Cyfluthrin, Cyhalodiamide, Cyhalothrin, Gamma-Cyhalothrin, Lambda-Cyhalothrin, Cypermethrin, Alpha-Cypermethrin, Zeta-Cypermethrin, Cyromazine, Deltamethrin, Diafenthiuron, Diazinon, Dichloranthraniliprole, Dieldrin, Difulve Nsuron, dimefluthrin, dimehypo, dimethoate, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flometoquin, flonicamid, flubendiamide, flucythrinate, flufenerim, flufenoxuron, flufenoxystrobin, fluensulfone, fluopyram, flupyradif lon, fluvalinate, tau-fluvalinate, fonofos, formetanate, fosthiazate, halofenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, indoxacarb, insecticidal soap, isofenphos, lufenuron, malathion, meperfluthrin, metaflumizone, metaldehyde, methamidophos, methidathion, methiocarb, methomyl, methoprene, methoxychlor, methoxyfenozide, metofluthrin, monocrotophos, monofluorothrin, nicotine, N-[1,1-Dimethyl-2-(methylthio)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1,1-dimethyl-2-(methylsulfinyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1,1-dimethyl-2-(methylsulfonyl)ethyl]-7-fluoro-2-(3-pyridinyl)-2H-indazole-4-carboxamide amide, N-(1-methylcyclopropyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide, N-[1-(difluoromethyl)cyclopropyl]-2-(3-pyridinyl)-2H-indazole-4-carboxamide, nitenpyram, nithiazine, novaluron, noviflumuron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, propargite, protrifenbute, piflubumid, pymetrozine, pyrafluprole, pyrethrin, pyridaben, pyridalyl, pyrifluquinazon, pyriminostrobin, pyriprole, pyriproxyfen, rotenone, ryanodine, silafluofen, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulprofos, sulfoxaflor, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, tetrachlorantraniliprole, tetrachlorvinphos, tetramethrin, tetramethylfluthrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, thioxazaphen, tolfenpyrad, tralomethrin, triazamate, trichlorfon, triflumezopyrim, triflumuron, Bacillus thuringiensis (Bacillus The composition of embodiment Y1, wherein the insect pathogenic bacteria is selected from the group consisting of: Bacillus thuringiensis delta-endotoxin, entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi.

[0151] Embodiment Y3. The at least one further biologically active compound or agent is selected from the group consisting of abamectin, acetamiprid, acrinathrin, afidopiropen, amitraz, avermectin, azadirachtin, benfuracarb, bensultap, bifenthrin, buprofezin, carbaryl, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyha Lothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenitrothion, fenothiocarb, fenoxycarb, fenvalerate, fipronil, flometoquin, flonicamid, flubendiamide, flufenil. Noxuron, Flufenoxystrobin, Fluensulfone, Flupiprole, Flupyradifurone, Fluvalinate, Formetanate, Hosthiazate, Heptafluthrin, Hexaflumuron, Hydramethylnon, Imidacloprid, Indoxacarb, Lufenuron, Meperfluthrin, Metaflumizone, Methiocarb, Methomyl, Methoprene, Methoxyfenozide, Metofluthrin, Monofluorothrin, Nitenpyram, Nithiazine, Novaluron, Oxamyl, Piflubumid, Pimeth The composition of embodiment Y2, wherein the compound is selected from the group consisting of rhodin, pyrethrins, pyridaben, pyridalyl, pyriminostrobin, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulfoxaflor, tebufenozide, tetramethrin, tetramethylfluthrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, triflumezopyrim, triflumuron, Bacillus thuringiensis delta endotoxin, all strains of Bacillus thuringiensis, and all strains of nuclear polyhedrosis virus.

[0152] Embodiment Y4. The composition of any one of embodiments Y1-Y3, further comprising a liquid fertilizer.

[0153] Embodiment Y5. The composition of embodiment Y4, wherein the liquid fertilizer is aqueous.

[0154] Embodiment Y6. A soil drench formulation comprising the composition of any one of embodiments Y1-Y3.

[0155] Embodiment Y7. A spray composition comprising the composition of any one of embodiments Y1-Y3 and a propellant.

[0156] Embodiment Y8. A bait composition comprising the composition of any one of embodiments Y1-Y3, one or more food ingredients, optionally an attractant, and optionally a wetting agent.

[0157] Embodiment Y9. A trapping device for controlling invertebrate pests, comprising the bait composition of embodiment Y8 and a housing configured to contain the bait composition, wherein the housing has at least one opening sized to allow passage of an invertebrate pest thereby allowing the invertebrate pest to access the bait composition from a location external to the housing, and wherein the housing is further configured to be placed at or near a location of possible or known activity for the invertebrate pest.

[0158] Embodiment Y10. A composition comprising the composition of any of embodiments Y1-Y3, wherein the composition is a solid composition selected from dusts, powders, granules, pellets, prills, lozenges, tablets, and filled films.

[0159] Embodiment Y11. The composition of embodiment Y10, wherein the composition is water-dispersible or water-soluble.

[0160] Embodiment Y12. A liquid or dry formulation comprising the composition of any one of embodiments Y1-Y3 for use in drip irrigation systems, in-furrow at planting, in a hand-held sprayer, a backpack sprayer, a boom sprayer, a ground sprayer, an aerial application, an unmanned aerial vehicle, or in a seed treatment.

[0161] Embodiment Y13. A liquid or dry formulation according to embodiment Y12, wherein the formulation is sprayed in minute amounts.

[0162] Of note, compounds of the present disclosure are characterized by favorable metabolism and / or soil persistence patterns and exhibit activity in controlling a variety of agronomic and non-agronomic invertebrate pests.

[0163] Of particular note is that due to the invertebrate pest control spectrum and economic importance, the protection of agricultural crops from damage or injury caused by invertebrate pests by controlling invertebrate pests is an embodiment of the present disclosure.The compounds of the present disclosure also protect leaves or other plant parts that are not directly contacted with the compound of formula 1 or a composition containing this compound due to their favorable translocation properties or systemicity in plants.

[0164] Also of note as an embodiment of the present disclosure are compositions comprising a compound as described in any of the above embodiments, as well as any other embodiment described herein, and any combination thereof, and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, optionally further comprising at least one additional biologically active compound or agent.

[0165] Further noteworthy embodiments of the present disclosure are compositions for controlling invertebrate pests comprising a compound as described in any of the above embodiments, as well as any other embodiment described herein, and any combination thereof, and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, and optionally further comprising at least one additional biologically active compound or agent.Embodiments of the present disclosure further include a method for controlling invertebrate pests, comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound as described in any of the above embodiments (e.g., as a composition described herein).

[0166] The present disclosure also includes a composition comprising a compound according to any of the above embodiments in the form of a soil drench liquid formulation. The present disclosure further includes a method for controlling invertebrate pests, comprising contacting soil with a biologically effective amount of a liquid composition comprising a compound according to any of the above embodiments as a soil drench.

[0167] The present disclosure also includes a spray composition for controlling invertebrate pests, the spray composition comprising a biologically effective amount of a compound according to any of the above embodiments and a propellant. The present disclosure further includes a bait composition for controlling invertebrate pests, the bait composition comprising a biologically effective amount of a compound according to any of the above embodiments, one or more food materials, optionally an attractant, and optionally a wetting agent. The present disclosure also includes a device for controlling invertebrate pests, the device comprising the bait composition and a housing configured to contain the bait composition, where the housing has at least one opening sized to allow an invertebrate pest to pass therethrough, thereby allowing the invertebrate pest to access the bait composition from a location outside the housing, and the housing is further configured to be placed at or near a location of possible or known activity of the invertebrate pest.

[0168] Embodiments of the present disclosure also include a method for protecting seeds from invertebrate pests comprising contacting the seeds with a biologically effective amount of a compound according to any of the above embodiments.

[0169] Embodiments of the present disclosure also include a method for protecting an animal from an invertebrate parasitic pest comprising administering to the animal a parasiticidally effective amount of a compound according to any of the above embodiments.

[0170] Embodiments of the present disclosure also include methods for controlling invertebrate pests, comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula 1, an N-oxide or a salt thereof (e.g., as a composition described herein), provided that the method is not a method of medical treatment of the human or animal body by therapy.

[0171] The present disclosure also relates to such methods, wherein an invertebrate pest or its environment is contacted with a composition comprising a biologically effective amount of a compound of Formula 1, an N-oxide or a salt thereof, and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, optionally further comprising a biologically effective amount of at least one additional bioactive compound or agent, with the proviso that the method is not a method of medical treatment of the human or animal body by therapy.

[0172] The embodiments of the present disclosure also include the use of unmanned aerial vehicles (UAVs) to distribute the compositions disclosed herein over a planted area. In some embodiments, the planted area is an area containing a crop. In some embodiments, the crop is selected from monocotyledonous or dicotyledonous plants. In some embodiments, the crop is selected from rice, corn, barley, buckwheat, wheat, vegetables, tobacco, tea plants, fruit trees, and sugarcane. In some embodiments, the compositions disclosed herein are formulated for spraying at very low volumes. The products applied by drones can use water or oil as the spray carrier. Typical spray volumes (including products) used for drone spraying are 5.0 liters / ha to 100 liters / ha (about 0.5 to 10 gpa) worldwide. This includes a range from ultra-low spray volumes (ULV) to low spray volumes (LV). Although not common, there may be situations where even lower spray volumes are used, such as 1.0 liters / ha (0.1 gpa).

[0173] Compounds of formula 1 can be prepared by one or more of the following methods and variations described in schemes 1-6. The definitions of the substituents in the compounds of formulas 1-13 below are as defined above in the Summary unless otherwise specified. Compounds of formulas 1a and 1b are subsets of compounds of formula 1. The substituents of each subset of formulas are as defined for its parent formula unless otherwise specified. Ambient or room temperature is defined as about 20-25°C.

[0174] Compounds of formula 1 can be prepared by the method shown in scheme 1. The values ​​of R1, R2, R3, R4, R5, n and Q are as previously defined. In the method of scheme 1, a carboxylic acid of formula 2 is reacted with an amine of formula 3 by condensation promoted by a known amide coupling reagent. Coupling reagents useful in this method include, but are not limited to, T3P (1-propanephosphonic acid cyclic anhydride), DIC / HOBt (diisopropylcarboximide / hydroxybenzotriazole), HATU (1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate), CDI (carbonyldiimidazole), and EDC (ethyl-3-(3-dimethylaminopropyl)carbodiimide). Coupling reagents are typically used in the presence of a base such as triethylamine, pyridine, 4-(dimethylamino)pyridine and N,N-diisopropylethylamine. Typical reaction conditions include an anhydrous aprotic solvent such as dichloromethane or tetrahydrofuran, and the reaction is generally carried out at a temperature between room temperature and the reflux temperature of the solvent. These reactions are well documented in the art and are demonstrated in Examples 1-3.

[0175] Scheme 1 [ka] Compounds of formula 1 can also be prepared by a two-step method as shown in scheme 2. In this method, an acid of formula 2 is converted to a compound of formula 4, where LG is a suitable leaving group, and then reacted with an amine of formula 3 to give a compound of formula 1. Compounds where LG is chloro (acid chloride) are very commonly used in this method. The coupling of the acid chloride with the amine can be carried out in a wide variety of solvents, including tetrahydrofuran, diethyl ether, and methylene chloride. The reaction is also carried out in the presence of a base, such as triethylamine, pyridine, picoline, 4-(dimethylamino)pyridine, and N,N-diisopropylethylamine. Acid chlorides are readily available from the corresponding acids by well-known methods, such as treatment with thionyl chloride or oxalyl chloride. Alternatively useful leaving groups are carboxylic acid sulfonates, which can be prepared from acids of formula 2 by treatment with alkyl or aryl sulfonyl chlorides or sulfonic anhydrides to form intermediate sulfonates which can then be reacted directly with amines of formula 3 in the presence of a base as described for the acid chlorides to give compounds of formula 1 directly.

[0176] Scheme 2 [ka] Compounds of formula 1 can be prepared by the method depicted in Scheme 3. In this method, 3-hydroxybenzamides of formula 5 are treated with a sulfonating reagent, such as a sulfonyl chloride or a sulfonic anhydride, in the presence of a base, such as triethylamine, pyridine, picoline, collidine, 4-(dimethylamino)pyridine, and N,N-diisopropylethylamine. Typical reaction conditions include anhydrous aprotic solvents, such as dichloromethane or tetrahydrofuran. The reaction is generally carried out at a temperature between 0° C. and room temperature.

[0177] Scheme 3 [ka] Compounds of formula 1a, which are a subset of formula 1, where Q contains a central triazole ring, can be prepared by the method shown in scheme 4. In this method, compounds of formula 6 are reacted with 1,1-dimethoxy-NN-dimethylmethanamine to form intermediate dimethylaminoimide of formula 7. This reaction is typically carried out in aprotic solvents such as methylene chloride, tetrahydrofuran, benzene, and toluene at temperatures up to the reflux temperature of the solvent. Compounds of formula 7 are then directly treated with hydrazines of formula 8 to obtain triazoles of formula 1a. This reaction is generally carried out in acetic acid, and may include a co-solvent at temperatures from room temperature to 100°C. This method is described in WO2017 / 192385.

[0178] Scheme 4 [ka] Compounds of formula 1b, a preferred subset of formula 1, containing products derived from S-alanine and pyridine or pyrimidine triazoles, can be prepared by the method shown in Scheme 5. The procedure for this method is the same as that described in Scheme 4, where the intermediate of formula 9 is derived from an S-alanine fragment and the hydrazine is a substituted pyridine or pyrimidine of formula 11.

[0179] Scheme 5 [ka] The intermediate of formula 2 can be prepared by the method shown in Scheme 6. In this method, the 3-hydroxybenzoate of formula 12 is treated with a sulfonyl chloride or sulfonic anhydride in the presence of a base such as triethylamine, pyridine, picoline, collidine, 4-(dimethylamino)pyridine and N,N-diisopropylethylamine. A preferred sulfonating reagent is trifluoromethanesulfonic anhydride. Typical reaction conditions include an anhydrous aprotic solvent such as dichloromethane or tetrahydrofuran. The reaction is generally carried out at a temperature between 0° C. and room temperature. The ester of formula 13 can then be hydrolyzed under standard conditions with a base such as sodium hydroxide or lithium hydroxide, which upon acidification gives the acid of formula 2.

[0180] Scheme 6 [ka] It is recognized that some of the reagents and reaction conditions described above for preparing compounds of formula 1 may be incompatible with certain functional groups present in those intermediates. In these cases, the incorporation of a sequence of protection / deprotection into the synthesis or interconversion of functional groups will aid in obtaining the desired reaction product. The use and selection of protecting groups will be apparent to those familiar with chemical synthesis (see, for example, Greene, TW; Wuts, PGM, Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). Those skilled in the art will recognize that in some cases, after the introduction of the reagents shown in the individual schemes, further routine synthetic steps not described in detail may be required to complete the synthesis of compounds of formula 1. Again, those skilled in the art will recognize that it may be necessary to combine and carry out the steps described in the above schemes in an order other than that suggested by the schemes presented to prepare compounds of formula 1.

[0181] The preparation of intermediates of formula 3 is described in WO 2017 / 192385, WO 2019 / 197468, WO 2020 / 193341, WO 2020 / 201079, WO 2021 / 083936, WO 2021 / 013720, WO 2021 / 013719, WO 2021 / 037614, WO 2021 / 165195, and WO 2021 / 068179.

[0182] It is recognized that some of the reagents and reaction conditions described above for preparing compounds of formula 1 may be incompatible with certain functional groups present in those intermediates. In these cases, the incorporation of a protection / deprotection sequence into the synthesis or functional group interconversion will aid in obtaining the desired reaction product. The use and selection of protecting groups will be apparent to those familiar with chemical synthesis (see, for example, Greene, TW; Wuts, PGM, Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). Those skilled in the art will recognize that in some cases, after the introduction of the reagents shown in the individual schemes, further routine synthetic steps not described in detail may be required to complete the synthesis of compounds of formula 1. Again, those skilled in the art will recognize that it may be necessary to combine and carry out the steps described in the above schemes in an order other than that suggested by the order presented to prepare compounds of formula 1.

[0183] As one of ordinary skill in the art will further recognize, the compounds of Formula 1 and intermediates described herein can also be subjected to a variety of electrophilic, nucleophilic, radical, organometallic, oxidative, and reductive reactions to add substituents or modify existing substituents.

[0184] Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following synthetic examples are therefore to be construed as merely illustrative and not limiting of the present disclosure in any way. The steps in the following synthetic examples are intended to describe the procedure for each step in the overall synthetic transformation, and the starting materials for each step are not necessarily prepared by the particular preparation procedure whose procedure is described in another example or step. Ambient or room temperature is defined as about 20-25°C. Percentages are by weight, except in the case of chromatographic solvent mixtures or unless otherwise specified. Parts and percentages in the case of chromatographic solvent mixtures are by volume, unless otherwise specified. 1 H NMR spectra are reported in ppm downfield from tetramethylsilane, where "s" means singlet, "d" means doublet, "t" means triplet, "q" means quartet, "m" means multiplet, "dd" means doublet of doublets, and "brs" means broad singlet.

[0185] Examples of intermediates useful in the preparation of compounds of the present disclosure are shown in Tables A1-A18. [ka]

[0186] [Table 7]

[0187] [Table 8]

[0188] [Table 9]

[0189] Tables A4 to A6 are R 2Each is constructed in the same manner as Tables A1 to A3, except that is -5-F.

[0190] Tables A7 to A9 are R 2 Each of the tables has the same structure as Tables A1 to A3, except that is 5-Cl.

[0191] Tables A10 to A12 are R 2 Each has the same structure as Tables A1 to A3, except that is 5-Br.

[0192] Tables A13 to A15 are R 2 but 5-CF3 Except for the above, each table is structured in the same manner as Tables A1 to A3.

[0193] Tables A16 to A18 are R 2 but -5-OCF3 Except for the above, each table is structured in the same manner as Tables A1 to A3.

[0194] Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present disclosure to its fullest extent. EXAMPLES

[0195] Synthesis Example 1 Preparation of 3-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazol-5-yl]ethyl]amino]carbonyl]-5-(trifluoromethyl)phenyl 1,1,1-trifluoromethanesulfonate (compound 2) Step A: Preparation of methyl 3-(trifluoromethyl)-5-(trifluoromethylsulfonyloxy)benzoate To a stirred solution of methyl 3-trifluoromethyl-5-hydroxyoxybenzoate (0.5 g, 2.27 mmol) in dichloromethane (20 ml) was added 2,4,6-collidine (0.36 ml, 2.72 mmol), 4-dimethylaminopyridine (55 mg, 0.45 mmol) and trifluoromethanesulfonic anhydride (0.45 ml, 2.72 mmol) at 0° C. and the mixture was stirred at room temperature for 1 h. The progress of the reaction was monitored by TLC (50% EtOAc / petroleum ether). The mixture was quenched with ice-cold water (50 ml) and extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with brine solution (25 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure at 35° C. to give the crude compound, which was loaded onto a silica gel column. Elution of the column with 10% ethyl acetate / petroleum ether gave the title compound (0.5 g, 62.5% yield) as a pale yellow liquid. 1H-NMR (400 MHz, CDCl3): δ = 8.35 (s, 1H), 8.13 (s, 1H), 7.72 (s, 1H), 4.00 (s, 3H). MS (EI): m / z 352.

[0196] Step B: Preparation of 3-(trifluoromethyl)-5-(trifluoromethylsulfonyloxy)benzoic acid To a stirred solution of compound from step A (0.5 g, 1.42 mmol) in tetrahydrofuran (12 ml) and water (4 ml) was added lithium hydroxide hydrate (0.089 g, 2.13 mmol) at 0° C. and the mixture was stirred at room temperature for 15 min. The progress of the reaction was monitored by TLC (100% ethyl acetate). The solvent was evaporated and the mixture was acidified with 1N HCl (about pH=2) and extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with brine (50 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the crude compound, which was purified by preparative HPLC to give the title compound (200 mg, 41.6% yield) as an off-white solid. MS (EI): m / z 337 (MH, 100).

[0197] Step C: Preparation of 3-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazol-5-yl]ethyl]amino]carbonyl]-5-(trifluoromethyl)phenyl 1,1,1-trifluoromethanesulfonate To a stirred solution of the compound from Example 1, Step B (0.150 g, 1.08 mmol) in dichloromethane (8 ml) was added 1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine (compound 4, 0.247 g, 1.30 mmol) and triethylamine (0.3 ml, 2.17 mmol) at 0° C. Then, propanephosphonic anhydride (T3P, 1.38 ml, 2.17 mmol) was added and the mixture was stirred at room temperature for 16 hours. The progress of the reaction was monitored by TLC (100% ethyl acetate). The reaction was quenched with ice water (30 ml) and extracted with dichloromethane (2×50 ml). The combined organic extracts were washed with brine (30 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the crude product, which was purified by preparative HPLC to give the title compound (50 mg, 22.6% yield). 1 H NMR (400MHz, CDCl3): δ=9.51-9.50(d,1H),8.98-8.97(d,2H),8.29(s,1H),8.24(s,1H),8.1 7(s,1H),8.15(s,1H),7.63-7.60(t,1H),6.03-6.00(t,1H),1.66-1.65(d,3H).MS(EI):m / z 511(M+1,100) The preparation of the intermediate 1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethanamine can be found in WO 2017 / 192385.

[0198] Synthesis Example 2 Preparation of 3-[[[1-[1-(5-cyano-2-pyridinyl)-1H-1,2,4-triazol-5-yl]ethyl]amino]carbonyl]-5-(trifluoromethyl)phenyl 1,1,1-trifluoromethanesulfonate (compound 19) Step A: Preparation of 3-[[[1-[1-(5-cyano-2-pyridinyl)-1H-1,2,4-triazol-5-yl]ethyl]amino]carbonyl]-5-(trifluoromethyl)phenyl 1,1,1-trifluoromethanesulfonate To a stirred solution of 3-(trifluoromethyl)-5-(trifluoromethylsulfonyloxy)benzoic acid (0.250 g, 1.16 mmol) from step B of Example 1 in dichloromethane (10 ml) was added 6-[5-(1-aminoethyl)-1H-1,2,4-triazol-1-yl]-3-pyridinecarbonitrile (0.393 g, 1.16 mmol) and triethylamine (0.48 ml, 3.50 mmol) at 0° C. Then, propanephosphonic anhydride (T3P, 1.48 ml, 2.33 mmol) was added and the mixture was stirred at room temperature for 16 hours. The progress of the reaction was monitored by TLC (70% EtOAc / petroleum ether). The reaction was quenched with ice water (50 ml) and extracted with dichloromethane (2×50 ml). The combined organic extracts were washed with brine (50 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the crude product, which was purified by preparative HPLC to give the title compound (56 mg, 10% yield). 1H NMR (400 MHz, CDCl3): δ = 8.87-8.86 (s, 1H), 8.18-8.17 (m, 2H), 8.10 (s, 1H), 8.01 (s, 1H), 7.96 (s, 1H), 7.68 (s, 1H), 7.55-7.53 (d, 1H), 6.45-6.41 (t, 1H), 1.73-1.72 (d, 3H). MS (EI): m / z 535 (M+1, 100).

[0199] Synthesis Example 3 3-[[(Cyclopropylmethyl)[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazol-5-yl]ethyl]amino]carbonyl]-5-(trifluoromethyl)phenyl 1,1,1-trifluoromethanesulfonate (Compound 11) Step A: Preparation of 3-[[(cyclopropylmethyl)[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazol-5-yl]ethyl]amino]carbonyl]-5-(trifluoromethyl)phenyl 1,1,1-trifluoromethanesulfonate To a stirred solution of 3-(trifluoromethyl)-5-(trifluoromethylsulfonyloxy)benzoic acid (0.2 g, 0.59 mmol) from Example 1, Step B in dichloromethane (10 ml) was added N-(cyclopropylmethyl)-α-methyl-1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-methanamine (0.173 g, 0.71 mmol) and triethylamine (0.24 ml, 1.77 mmol) at 0° C. Then, propanephosphonic anhydride (0.75 ml, 1.18 mmol) was added and the reaction was stirred at room temperature for 16 hours. The progress of the reaction was monitored by TLC (100% EtOAc). The reaction was quenched with ice water (100 ml) and extracted with dichloromethane (2×50 ml). The combined organic extracts were washed with brine (50 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the crude product, which was purified by Combi-flash to give the title compound (60 mg, 18% yield) as a pale yellow sticky liquid. 1H NMR (400 MHz, CDCl3): δ = 8.84 (bs, 2H), 8.12 (s, 1H), 7.53 (d, 2H), 7.36 (bs, 2H), 6.69 (bs, 1H), 3.01 (bs, 2H), 1.87-1.86 (d, 3H), 0.90-0.86 (m, 1H), 0.42-0.37 (m, 2H), 0.04-0.02 (m, 2H). MS (EI): m / z 565 (M+1, 100). The preparation of the intermediate N-(cyclopropylmethyl)-α-methyl-1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-methanamine can be found in WO 2017 / 192385.

[0200] Synthesis Example 4 Enantiomer separation 3-chloro-5-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazol-5-yl]ethyl]amino]carbonyl]phenyl 1,1,1-trifluoromethanesulfonate (compound 8; (-) enantiomer) and 3-chloro-5-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazol-5-yl]ethyl]amino]carbonyl]phenyl 1,1,1-trifluoromethanesulfonate (compound 9; (+) enantiomer) Procedure: The enantiomers of 3-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazol-5-yl]ethyl]amino]carbonyl]-5-(trifluoromethyl)phenyl 1,1,1-trifluoromethanesulfonate (compound 2) from Example 1 were separated and characterized by chiral supercritical fluid chromatography (SFC) using the following method. SFC method conditions: Column: CHIRALPAK IC(4.6 * 250mm) 5μm Co-solvent: 0.5% DEA in methanol Total flow rate: 3g / min % of co-solvent: 10 ABPR:1500si Temperature: 30℃ SFC purification gave: Peak 1 (RT value: 1.98 by chiral HPLC): 110 mg; 1H-NMR, MS and optical rotation consistent with the (-) enantiomer of 3-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazol-5-yl]ethyl]amino]carbonyl]-5-(trifluoromethyl)phenyl 1,1,1-trifluoromethanesulfonate. 1 H NMR(400MHz,CDCl3):δ= 8.93-8.92(d,2H),8.11(s,1H),8.06(s,1H),7.97(s,1H),7.67-7.65(d,2H),7.43-7.41(t,1H),6.48-6.42(m,1H),1.72-1.71(d,3H). MS(EI): m / z 511.23(M+1). [α] = -101.2 (C = 0.2%, MeOH) Peak 2 (RT value: 2.55 by chiral HPLC): 110 mg; 1H-NMR, MS and optical rotation consistent with the (+) enantiomer of 3-chloro-5-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazol-5-yl]ethyl]amino]carbonyl]phenyl 1,1,1-trifluoromethanesulfonate. 1 H NMR (400MHz, CDCl3): δ=8.93-8.92(d,2H),8.11-8.06(d,1H),7.97(s,1H) ,7.67-7.64(t,2H),7.43-7.4(t,1H),6.47-6.43(m,1H),1.72-1.7(d,3H). MS(EI): m / z 511.19(M+1). [α] = +84.32 (C = 0.2%, MeOH)

[0201] The compounds in Tables 1-120 below can be prepared by the procedures described herein and methods known in the art. The following abbreviations are used in the tables below: Me means methyl, OMe means methoxy, Et means ethyl, OEt means ethoxy, n-Pr means n-propyl, i-Pr means isopropyl, c-Pr means cyclopropyl, n-Bu means n-butyl, s-Bu means sec-butyl, t-Bu means tertiary butyl, c-Bu means cyclobutyl, Ph means phenyl, and CN means cyano. Table 1 [ka] In the formula, R 3 is H.

[0202] [Table 10]

[0203] [Table 11]

[0204] Table 2 [ka] In the formula, R 3 is Me.

[0205] [Table 12]

[0206] [Table 13]

[0207] Table 3 [ka] In the formula, R 3 is i-Pr.

[0208] [Table 14]

[0209] [Table 15]

[0210] Table 4 [ka] In the formula, R 3 is CH2(c-Pr).

[0211] [Table 16]

[0212] [Table 17]

[0213] Table 5 [ka] In the formula, R 3 is CH2Ph.

[0214] [Table 18]

[0215] [Table 19]

[0216] Table 6~Table 10 [ka] Tables 6-10 are constructed the same as Tables 1-5, respectively, except that the structures in Tables 1-5 are replaced with the structures described above for Tables 6-10.

[0217] Table 11~Table 15 [ka] Tables 11-15 are constructed the same as Tables 1-5, respectively, except that the structures in Tables 1-5 are replaced with the structures described above for Tables 11-15.

[0218] Table 16~Table 20 [ka] Tables 16-20 are constructed the same as Tables 1-5, respectively, except that the structures in Tables 1-5 are replaced with the structures described above for Tables 16-20.

[0219] Tables 21 to 40 show R 2 Each is constructed in the same manner as Tables 1 to 20, except that is 5-F.

[0220] Tables 41 to 60 show R 2 Each of the formulas is constructed in the same manner as Tables 1 to 20, except that is 5-Cl.

[0221] Tables 61 to 80 are R 2 Each is constructed in the same manner as Tables 1 to 20, except that is 5-CF3.

[0222] Tables 81 to 100 are R 2 Each of the compounds has the same structure as that of Tables 1 to 20, except that the compound is 5-OCF3.

[0223] Tables 101 to 120 are R 2 Each has the same structure as Tables 1 to 20, except that is 5-Br.

[0224] [ka] Tables 121-125 are constructed the same as Tables 1-5, respectively, except that the structures in Tables 1-5 are replaced with the structures described above for Tables 121-125.

[0225] [ka] Tables 126-130 are structured the same as Tables 1-5, respectively, except that the structures in Tables 1-5 are replaced with the structures described above for Tables 126-130.

[0226] [ka] Tables 131-135 are constructed the same as Tables 1-5, respectively, except that the structures in Tables 1-5 are replaced with the structures described above for Tables 131-135.

[0227] Tables 136 to 140 show R 2Except that is 5-F, they are constructed in the same manner as Tables 126 to 130, respectively.

[0228] Tables 141 to 145 are R 2 Each of these is constructed in the same manner as Tables 126 to 130, except that is 5-Cl.

[0229] Tables 146 to 150 show R 2 Each is constructed in the same manner as Tables 126 to 130, except that is 5-CF3.

[0230] Tables 151 to 155 are R 2 Each is configured in the same manner as Tables 126 to 130, except that is 5-OCF3.

[0231] Tables 156 to 160 show R 2 The structures are the same as those in Tables 126 to 130, respectively, except that is 5-Br.

[0232] Tables 161 to 165 are R 2 Except that is 5-F, they are constructed in the same manner as Tables 126 to 130, respectively.

[0233] Tables 166 to 170 are R 2 Each of these is constructed in the same manner as Tables 126 to 130, except that is 5-Cl.

[0234] Tables 171 to 175 are R 2 Each is constructed in the same manner as Tables 126 to 130, except that is 5-CF3.

[0235] Tables 176 to 180 are R 2 Each is configured in the same manner as Tables 126 to 130, except that is 5-OCF3.

[0236] Tables 181 to 185 are R 2 The structures are the same as those in Tables 126 to 130, respectively, except that is 5-Br.

[0237] Tables 186 to 190 are R 2 Except that is 5-F, they are constructed in the same manner as Tables 126 to 130, respectively.

[0238] Tables 191 to 195 are R 2 Each of these is constructed in the same manner as Tables 126 to 130, except that is 5-Cl.

[0239] Tables 196 to 200 are R 2 Each is constructed in the same manner as Tables 126 to 130, except that is 5-CF3.

[0240] Tables 201 to 205 are R 2 Each is configured in the same manner as Tables 126 to 130, except that is 5-OCF3.

[0241] Tables 206 to 210 are 2 The structures are the same as those in Tables 126 to 130, respectively, except that is 5-Br.

[0242] Formulation / Practical Use The compounds of the present disclosure will generally be used as invertebrate pest control active ingredients in compositions, i.e., formulations, with at least one additional ingredient selected from the group consisting of surfactants, solid diluents, and liquid diluents, which act as carriers. The ingredients of the formulation or composition are selected to suit the physical properties of the active ingredient, the application form, and environmental factors such as soil type, moisture, and temperature.

[0243] Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions, oil-in-water emulsions, flowable concentrates and / or suspoemulsions), which can optionally be thickened into gels. Common types of aqueous liquid compositions include soluble concentrates, suspension concentrates, capsule suspensions, concentrated emulsions, microemulsions, oil-in-water emulsions, flowable concentrates and suspoemulsions. Common types of non-aqueous liquid compositions are emulsifiable concentrates, microemulsifiable concentrates, dispersible concentrates and oil dispersions.

[0244] Common types of solid compositions are dusts, powders, granules, pellets, prills, lozenges, tablets, filler films (including seed coatings), etc., which may be water-dispersible ("wettable") or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly useful for seed treatment. Active ingredients can be (micro)encapsulated and further processed into suspension or solid formulations; alternatively, the entire formulation of active ingredients can be encapsulated (or "overcoated"). Encapsulation can control or delay the release of the active ingredient. Emulsifiable granules combine the advantages of both emulsifiable concentrated formulations and dry granular formulations. High-strength compositions are mainly used as intermediates for further formulation.

[0245] Sprayable formulations are typically spread in a suitable medium before spraying. Such liquid and solid formulations are formulated to be easily diluted in the spray medium, usually water, but sometimes in another suitable medium, such as aromatic or paraffinic hydrocarbons, or vegetable oils. Spray volumes can range from about one to several thousand liters per hectare, but more typically range from about 10 to several hundred liters per hectare. Sprayable formulations can be tank-mixed with water, or another suitable medium, for foliar treatment by aerial or ground application, or for application to the growing medium of plants. Liquid and dry formulations can be injected directly into drip irrigation systems or metered into the furrow at planting. Liquid and solid formulations can be applied as seed treatments on seeds of crops and other desirable vegetation before planting to protect the growing roots and other underground plant parts and / or leaves by systemic absorption.

[0246] One method of distributing the compositions disclosed herein over a target area, such as, but not limited to, a field containing a crop, is by using a drone. The use of drones or unmanned aerial vehicles (UAVs) in agricultural applications, such as for treating fields with chemical products, is rapidly expanding. A container of chemical product is coupled to the UAV and a material distribution system attached to the UAV, and the UAV is maneuvered over the area to be treated while the chemical product is distributed.

[0247] The formulations typically contain effective amounts of active ingredients, diluents, and surfactants, within the general ranges below, the total of which adds up to 100 weight percent.

[0248] [Table 20]

[0249] Examples of solid diluents include clays such as bentonite, montmorillonite, attapulgite, kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and sodium bicarbonate, and sodium sulfate. Typical solid diluents are described in the following literature: Watkins et.al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.

[0250] Examples of liquid diluents include water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), alkyl phosphates (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oil, normal paraffin, isoparaffin), alkylbenzenes, alkylnaphthalenes, glycerin, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatic alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone, and 4-hydroxy-4-methyl-2-pentanone. Examples of diluents include esters such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isobornyl acetate, other esters such as alkylated lactates, dibasic esters, alkyl and aryl benzoates, γ-butyrolactone and alcohols which 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 to C8 22 ), for example vegetable seed and fruit oils (e.g., olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel oils), fats of animal origin (e.g., beef tallow, pork fat, lard, cod liver oil, fish oils) and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated), where the fatty acids can be obtained by hydrolysis of glycerol esters from plant and animal sources and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.

[0251] The solid and liquid compositions of the present disclosure often contain one or more surfactants.Surfactants (also known as "surface active agents"), when added to a liquid, generally modify, and in most cases reduce, the surface tension of the liquid.Depending on the nature of the hydrophilic and lipophilic groups in the surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers, or antifoaming agents.

[0252] Surfactants can be classified as nonionic, anionic or cationic.Nonionic surfactants useful for the present compositions include, but are not limited to, alcohol alkoxylates, such as those based on natural and synthetic alcohols (which may be branched or linear) and prepared from alcohols and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof;amine ethoxylates, alkanolamides, and ethoxylated alkanolamides;alkoxylated triglycerides, such as ethoxylated soybean oil, castor oil, and rapeseed oil;alkylphenol alkoxylates, such as octylphenol ethoxylate, nonylphenol ethoxylate, dinonylphenol ethoxylate, and dodecylphenol ethoxylate (prepared from phenol and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof);block polymers prepared from ethylene oxide or propylene oxide, and the end blocks of which are prepared from propylene oxide. , reverse block polymers; ethoxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenols (including those prepared from ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); fatty acid esters, glycerol esters, lanolin-based derivatives, polyethoxylate esters such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters, and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives such as sorbitan esters; polymeric surfactants such as random copolymers, block copolymers, alkyd PEG (polyethylene glycol) resins, graft or comb polymers, and star polymers; polyethylene glycol (PEG); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar derivatives such as sucrose esters, alkyl polyglycosides, and alkyl polysaccharides.

[0253] Useful anionic surfactants include, but are not limited to, alkylarylsulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenylsulfonic acid derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acid or anhydrides; olefin sulfonates, phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates, and phosphate esters of styrylphenol ethoxylates; protein-based surfactants; sarcosine derivatives; styrylphenol ether sulfenes; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides such as N,N-alkyl taurates; sulfonates of benzene, cumene, toluene, xylene, and dodecyl and tridecylbenzene; sulfonates of condensed naphthalenes; sulfonates of naphthalene and alkylnaphthalenes; sulfonates of fractionated petroleum oils; sulfosuccinamates; and sulfosuccinates and their derivatives, such as dialkyl sulfosuccinate salts.

[0254] Useful cationic surfactants include, but are not limited to, amides and ethoxylated amides; amines such as N-alkylpropanediamines, tripropylenetriamine, and dipropylenetetramine; and ethoxylated amines, ethoxylated diamines, and propoxylated amines (prepared from amines and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts, and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

[0255] Also useful in the compositions of the present invention are mixtures of nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants.Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in various published references, including McCutcheon's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A.S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.

[0256] The compositions of the present disclosure may also contain formulation aids and additives known to those skilled in the art as formulation aids, some of which may also function as solid diluents, liquid diluents or surfactants. Such formulation aids and additives may control pH (buffers), foaming during processing (antifoaming agents such as polyorganosiloxanes), settling of active ingredients (suspending agents), viscosity (thixotropic thickeners), microbial growth in containers (antimicrobial agents), freezing of the product (antifreeze agents), color (dye / pigment dispersions), wash-off (film formers or spreading agents), evaporation (evaporation retardants) and other formulation properties. Film formers include, for example, polyvinyl acetate, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymers, polyvinyl alcohol, polyvinyl alcohol copolymers and waxes. Examples of formulation aids and additives include those described in McCutcheon's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03 / 024222.

[0257] The compound of formula 1 and any other active ingredients are typically incorporated into the composition by dissolving the active ingredients in a solvent or grinding in a liquid or dry diluent. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is not miscible with water, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Active ingredient slurries with particle sizes up to 2,000 μm can be wet-milled using a media mill to obtain particles with an average particle size of less than 3 μm. Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. Pat. No. 3,060,084) or can be further processed by spray drying to form water-dispersible granules. Dry formulations usually require a dry grinding process that results in an average particle size in the range of 2-10 μm. Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid energy mill). Granules and pellets can be prepared by spraying the active material onto preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp. 147-48; Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57, and WO 91 / 13546 below. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442, and German Patent No. 3,246,493. Tablets can be prepared as taught in U.S. Patent Nos. 5,180,587, 5,232,701 and 5,208,030. Films can be prepared as taught in British Patent No. 2,095,558 and U.S. Patent No. 3,299,566.

[0258] For further information regarding formulation techniques, see T. S. Woods, "The Formulator's Toolbox-Product Forms for Modern Agriculture", in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. R. Roberts, Eds, Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also the following documents: U.S. Pat. No. 3,235,361, column 6, line 16 to column 7, line 19, and Examples 10 to 41; U.S. Pat. No. 3,309,192, column 5, line 43 to column 7, line 62, and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138 to 140, 162 to 164, 166, 167, and 169 to 182; U.S. Pat. No. 2,891,855, column 3, line 66 to column 5, line 17, and Examples 1 to 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.

[0259] In the following examples, all formulations are prepared by conventional methods. Compound numbers refer to compounds in index table A. Without further elaboration, it is believed that those skilled in the art who use the above description can make the most of this disclosure. Therefore, the following examples are merely illustrative and do not limit the present disclosure in any way. Percentages are by weight unless otherwise specified.

[0260] Example A high strength concentrate Compound 2 98.5% Silica aerogel 0.5% Synthetic amorphous fine silica 1.0%

[0261] Example B Wettable Powder Compound 2 65.0% Dodecylphenol polyethylene glycol ether 2.0% Sodium lignosulfonate 4.0% Sodium silicoaluminate 6.0% Montmorillonite (calcined) 23.0%

[0262] Example C granules Compound 1 10.0% Attapulgite Granules (low volatility, 0.71 / 0.30 mm; USS No. 25-50 sieve) 90.0%

[0263] Example D Extrusion Pellets Compound 3 25.0% Anhydrous sodium sulfate 10.0% Crude calcium lignosulfonate 5.0% Sodium alkylnaphthalene sulfonate 1.0% Calcium / Magnesium Bentonite 59.0%

[0264] Example E emulsifiable concentrate Compound 2 10.0% Polyoxyethylene sorbitol hexoleate 20.0% C6-C10 fatty acid methyl esters 70.0%

[0265] Example F Microemulsion Compound 19 5.0% Polyvinylpyrrolidone-vinyl acetate copolymer 30.0% Alkyl polyglycoside 30.0% Glyceryl monooleate 15.0% Water 20.0%

[0266] Example G Seed treatment Compound 2 20.00% Polyvinylpyrrolidone-vinyl acetate copolymer 5.00% Montan Acid Wax 5.00% Calcium lignosulfonate 1.00% Polyoxyethylene / Polyoxypropylene Block Copolymer 1.00% Stearyl alcohol (POE 20) 2.00% Polyorganosilane 0.20% Coloring agent Red pigment 0.05% Water 65.75%

[0267] Example H Fertilizer stick Compound 1 2.5% Pyrrolidone-styrene copolymer 4.8% Tristyrylphenyl 16-ethoxylate 2.3% Talc 0.8% Corn starch 5.0% Slow release fertilizer 36.0% Kaolin 38.0% Water 10.6%

[0268] Example I Suspension concentrate Compound 4 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 defoamer 0.1% 1,2-Benzisothiazolin-3-one 0.1% Water 53.7%

[0269] Example J Emulsion in Water Compound 10 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 defoamer 0.1% 1,2-Benzisothiazolin-3-one 0.1% Aromatic petroleum hydrocarbons 20.0 Water 58.7%

[0270] Example K Oil Dispersion Compound 19 25% Polyoxyethylene sorbitol hexaoleate 15% Organically modified bentonite clay 2.5% Fatty acid methyl ester 57.5%

[0271] Example L Suspo Emulsion Compound 2 10.0% Imidacloprid 5.0% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone defoamer 0.1% 1,2-Benzisothiazolin-3-one 0.1% Aromatic petroleum hydrocarbons 20.0% Water 53.7%

[0272] The compounds of the present disclosure show activity against a wide range of invertebrate pests. These pests include invertebrates that live in various environments, such as, for example, plant foliage, roots, soil, harvested crops or other foods, building structures, or animal skins. These pests include invertebrates that feed, for example, on foliage (including leaves, stems, flowers, and fruits), seeds, wood, textile fibers, or animal blood or tissues, thereby causing damage or harm to, for example, growing and stored agricultural crops, forests, greenhouse crops, ornamental plants, nursery crops, stored food or fiber products, or buildings or their structures or components, or are harmful to animal health or public health. Those skilled in the art will understand that not all compounds are equally effective against all developmental stages of all pests.

[0273] Thus, these compounds and compositions are agronomically useful for protecting agricultural crops from phytophagous invertebrate pests, and non-agronomically useful for protecting other horticultural crops and plants from phytophagous invertebrate pests. This utility includes protecting crops and other plants (i.e., both agronomic and non-agronomic) that contain genetic material introduced by genetic engineering (i.e., gene transfer) or modified by mutagenesis to provide advantageous traits. Examples of such traits include resistance to herbicides, resistance to phytophagous pests (e.g., insects, mites, aphids, spiders, nematodes, snails, plant pathogenic fungi, bacteria and viruses), improved plant growth, improved tolerance to adverse growing conditions such as high or low temperatures, low or high soil moisture, and high salinity, increased flowering or fruiting, higher yields, earlier maturation, higher quality and / or nutritional value of the harvested product, or improved storage or processing properties of the harvested product. Transgenic plants can be modified to express multiple traits. Examples of plants containing traits resulting from genetic engineering or mutagenesis include varieties of corn, cotton, soybean and potato that express insecticidal Bacillus thuringiensis toxins, such as YIELD GARD®, KNOCKOUT®, STARLINK®, BOLLGARD®, NuCOTN® and NEWLEAF®, INVICTA RR2 PRO™, and herbicide-tolerant varieties of corn, cotton, soybean and canola, such as ROUNDUP READY®, LIBERTY LINK®, IMI®, STS® and CLEARFIELD®, as well as crops that express N-acetyltransferase (GAT) to provide tolerance to glyphosate herbicides, or contain the HRA gene to provide tolerance to herbicides that inhibit acetolactate synthase (ALS). The compounds and compositions may exhibit improved efficacy due to traits introduced by genetic engineering or modified by mutagenesis, thereby improving the phenotypic expression or efficacy of the trait or enhancing the invertebrate pest control efficacy of the compounds and compositions.In particular, the compounds and compositions may exhibit enhanced efficacy through the phenotypic expression of proteins or other natural products that are toxic to invertebrate pests, resulting in more than additive control of these pests.

[0274] The composition of the present disclosure may also optionally include a fertilizer composition comprising at least one plant nutrient selected from, for example, nitrogen, phosphorus, potassium, sulfur, calcium, magnesium, iron, copper, boron, manganese, zinc, and molybdenum. Of note are compositions comprising at least one fertilizer composition comprising at least one plant nutrient selected from nitrogen, phosphorus, potassium, sulfur, calcium, and magnesium. The composition of the present disclosure further comprising at least one plant nutrient may be in the form of a liquid or solid. Of note are solid formulations in the form of granules, small bars, or tablets. The solid formulations comprising fertilizer compositions may be prepared by mixing the compound or composition of the present disclosure and the fertilizer composition together with the formulation ingredients, and then preparing the formulation by a method such as granulation or extrusion. Alternatively, the solid formulations may be prepared by spraying a solution or suspension of the compound or composition 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 bars, or tablets, and then evaporating the solvent.

[0275] Non-agronomic uses refer to invertebrate pest control in areas other than the field of crop plants. Non-agronomic uses of the compounds and compositions include invertebrate pest control in stored grains, legumes and other foods, and fabrics such as clothing and carpets. Non-agronomic uses of the compounds and compositions also include invertebrate pest control in ornamental plants, forests, gardens, roadsides and railroad rights-of-way, and turf such as lawns, golf courses and pastures. Non-agronomic uses of the compounds and compositions also include invertebrate pest control in homes and other buildings that may be occupied by humans and / or companion animals, farms, ranches, zoo animals or other animals. Non-agronomic uses of the compounds and compositions also include pest control such as termites that may damage wood or other structural materials used in buildings.

[0276] Non-agronomic uses of the compounds and compositions also include protecting human and animal health by controlling invertebrate pests that are parasitic or transmit infectious diseases. Control of animal parasites includes controlling ectoparasites that infest the surface of the host animal's body (e.g., shoulders, armpits, abdomen, inner thighs) and endoparasites that infest the host animal's body (e.g., stomach, intestines, lungs, veins, subcutaneous, lymphatic tissue). Externally parasitic or disease-transmitting pests include, for example, chigger larvae, ticks, lice, mosquitoes, flies, mites, and fleas. Endoparasites include heartworms, hookworms, and parasitic helminths. The compounds and compositions of the present disclosure are suitable for systemic and / or non-systemic control of parasitic infestation or infection in animals. The compounds and compositions of the present disclosure are particularly suitable for dealing with ectoparasites or disease-transmitting pests. The compounds and compositions of the present disclosure are suitable for treating 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 household animals, such as dogs, cats, pet birds and ornamental fish; and so-called laboratory animals, such as hamsters, guinea pigs, rats and mice. Treating these parasites reduces mortality and performance loss (for meat, milk, wool, hides, eggs, honey, etc.), so that the application of compositions containing the compounds of the present disclosure allows more economical and simple husbandry of animals.

[0277] Examples of agronomic or non-agronomic invertebrate pests include the order Lepidoptera, e.g., cutworms, cutworms, and tobacco budworms of the family Noctuidae, e.g., the pink stem borer (Sesamia inferens Walker), the corn stalk borer (Sesamia nonagrioides Lefebvre), the southern armyworm (Spodoptera eridania Cramer), the fall armyworm (Spodoptera frugiperda J. E. Smith), the larvae of the beet armyworm moth (Spodoptera exigua Huebner), the cotton leafworm (Spodoptera littoralis Boisduval), Yellow stripped cutworm (Spodoptera ornithogalli Guenee), Black cutworm (Agrotis ipsilon Hufnagel), Velvet bean caterpillar (Anticarsia gemmatalis Huebner), Green fruit worm (Lithophane antennata Walker), Cabbage cutworm (Barathra brassicae Linnaeus), Soybean looper (Pseudoplusia includens Walker), Cabbage looper (Trichoplusia ni Huebner), Tobacco budworm (Heliothis virescens Fabricius) eggs, larvae and adults; borers, cocoon builders, webworms, cornworms, caterpillars and leaf-eating insects of the Pyralidae family (e.g., the European corn borer (Ostrinia nubilalis Huebner), the navel orangeworm (Amyelois transitella)transitella (Walker), corn root webworm (Crambus caliginosellus (Clemens), sod webworms (Family: Pyralidae: Crambinae), e.g. sod worm (Herpetogramma licarsisalis (Walker), sugarcane stem borer (Chilo infuscatellus (Snellen)), tomato small borer (Neoleucinodes elegantalis (Guenee)), green leafroller (Cnaphalocrocis medinalis), grape leaf folder (Desmia funeralis (Huebner)), melon worm (Diaphania nitidalis Stoll), Cabbage centre grub (Helluala hydralis Guenee), Yellow stem borer (Scirpophaga incertulas Walker), Early shoot borer (Scirpophaga infuscatellus Snellen), White stem borer (Scirpophaga innotata Walker), Top shoot borer (Scirpophaga nivella Fabricius), Dark-headed rice borer (Chilo polychrysus Meyrick), Striped rice borer (Chilo suppressalis Walker), Cabbage cluster caterpillar (Crocidolomia binotalis); Tortricidae leafrollers, budworms, seedworms, and fruitworms (e.g., the codling moth (Cydia pomonella Linnaeus), the grapeberry moth (Paralobesia viteana (Endopizaviteana Clemens), pear fruit moth (Grapholita molesta Busck), citrus false ring moth (Cryptophlebia leucotreta Meyrick), citrus borer (Ecdytolopha aurantiana Lima), red striped leafroller (Argyrotaenia velutinana Walker), diagonal striped leafroller (Choristoneura rosaceana Harris), light brown apple moth (Epiphyas postvittana Walker), European grapeberry moth (Eupoecilia ambiguella Huebner), apple bud moth (Pandemis pilsana pyrusana) Kearfott), omnivorous leafrollers (Platynota stultana) Walsingham), striped fruit tree moth (Pandemis cerasana Huebner), apple brown moth (Pandemis heparana Denis & Schiffermueller); and many other economically important Lepidoptera (e.g. diamondback moth (Plutella xylostella Linnaeus), cotton bollworm (Pectinophora gossypiella Saunders), gypsy moth (Lymantria dispar Linnaeus), peach fruit borer (Carposina niponensis Walsingham), peach twig borer (Anarsia lineatella lineatella)Zeller), potato tuber moth larvae (Pthorimaea operculella)Zeller), spotted teniform leafminer (Lithocolletis blancardella)Fabricius), Asian apple leafminer (Lithocolletis ringoniella)Matsumura), rice leafminer (Lerodea eufala)Edwards), apple leafminer (Leucoptera scitella)Zeller);The order Blattodea, which includes cockroaches of the families Blattellidae and Blattidae (e.g., the Oriental cockroach (Blatta orientalis) Linnaeus), the Asian cockroach (Blatella asahinai) Mizukubo), the German cockroach (Blattella germanica) Linnaeus), the brown banded cockroach (Supella longipalpa) Fabricius), the American cockroach (Periplaneta americana) Linnaeus), the brown brown cockroach (Periplaneta brunnea) Burmeister), the Madeira cockroach (Leucophaea maderae) eggs, nymphs and adults of the brown cockroach (Periplaneta fuliginosa Service), the American cockroach (Periplaneta australasiae Fabr.), the lobster cockroach (Nauphoeta cinerea Olivier) and the smooth cockroach (Symploce pallens Stephens);Coleoptera, including weevils from the families Anthribidae, Bruchidae, and Curculionidae (e.g., boll weevil (Anthonomus grandis) Boheman), rice water weevil (Lissorhoptrus oryzophilus Kuschel), granary grain weevil (Sitophilus granarius Linnaeus), rice weevil (Sitophilus oryzae Linnaeus)), annual grass weevil (Listronotus maculatus), maculicollis Dietz), bluegrass weevil (Sphenophorus parvulus Gyllenhal), grass weevil (Sphenophorus venatus vestitus); Eggs, folivorous, fruit-eating, root-eating, seed-eating and vesicular tissue-eating larvae and adults of the Denver weevil (Sphenophorus cicatristriatus Fahraeus); flea beetles, cucumber beetles, root beetles, leaf beetles, potato beetles and leaf miners of the family Chrysomelidae (e.g., Colorado potato beetle (Leptinotarsa ​​decemLineata) Say), Western corn rootworm (Diabrotica virgifera virgifera LeConte)); scarab beetles and other beetles of the family Scarabaeidae (e.g., Japanese beetle (Popillia japonica Newman), Japanese beetle (Anomala orientalis (Waterhouse), Exomala orientalis (Waterhouse) Baraud), Northern scarab beetle (Cyclocephala borealis Arrow), Southern scarab beetle (Cyclocephala immaculata Olivier or C. lurida Bland), dung beetles and grubs (Aphodius spp.), a species of dung beetle (Ataenius spretulus Haldeman), a species of green dung beetle (Cotinis nitida Linnaeus), red-billed scarab beetle (Maladera castanea (Arrow), cockroach beetles (Phyllophaga spp.) and European scarab beetles (Rhizotrogus majalis Razoumowsky); dermestidae beetles; elateridae click beetle larvae; Scolytidae bark beetles and Tenebrionidae red flour beetles.

[0278] Further agronomic and non-agronomic pests include: eggs, adults and larvae of the order Dermaptera, including earwigs of the family Forficulidae (e.g. European earwig (Forficula auricularia Linnaeus), black earwig (Chelisoches morio Fabricius)); eggs, adults and larvae of the order Hemiptera, including miridae, mirid bugs, cicadas of the family Cicadidae, leafhoppers of the family Cicadellidae (e.g. Empoasca spp.), bedbugs of the family Cimicidae (e.g., Cimex lectularius Linnaeus), planthoppers of the families Fulgoridae and Delphacidae, treehoppers of the families Membracidae, psyllids of the families Liviidae, Psyllidae, and Triozidae, whiteflies of the family Aleyrodidae, aphids of the family Aphididae, root aphids of the family Phylloxeridae, and rhinoceros beetles of the family Aleyrodidae. Mealybugs from the Pseudococcidae family, scale insects from the Coccidae, Diaspididae and Margarodidae families, Tingidae scale bugs, Pentatomidae stink bugs, Lygaeidae stink bugs (e.g. hairy stink bug (Blissus leucopterus hirtus) Eggs, larvae, adults and nymphs of the following bugs: leucopterus hirtus (Montandon) and the southern American long-horned bug (Blissus insularis (Barber)) and other seed bugs, Cercopidae (corn bugs), Coreidae (core bugs), and Pyrrhocoridae (spotted spotted bugs) and cotton stainer (cotton stainer).

[0279] Agronomic and non-agronomic pests also include: the order Acari (mites), for example the red and red spider mites of the family Tetranychidae (e.g. Panonychus ulmi Koch), Tetranychus urticae Koch, McDaniel's mites (Tetranychus mcdanieli McGregor); the soft-spotted spider mites of the family Tenuipalpidae (e.g. Brevipalpus vulgaris, Brevipalpus spp. ... lewisi (McGregor); rust and eriophyid mites and other leaf-eating mites of the family Eriophyidae, as well as mites of importance in human and animal health, i.e. dust mites of the family Epidermoptidae, Demodex mites of the family Demodex mites, and grain mites of the family Glycyphagidae; ticks of the family Ixodidae, commonly known as hard mites, such as the deer tick (Ixodes scapularis) Say, the Australian paralysis tick (Ixodes holocyclus) Neumann, the American dog tick (Dermacentor variabilis) Say, the Lone Star tick (Amblyomma americanum Linnaeus) and Argasidae ticks, commonly known as rosy mites (e.g., Ornithodoros turicata, common poultry tick (Argas radiatus)); eggs, larvae, nymphs and adults of sarcoptid and scabies mites from the families Psoroptidae, Pyemotidae and Sarcoptidae; grasshoppers, migratory locusts and crickets (e.g., migratory grasshoppers (e.g., Melanoplus sanguinipes Fabricius, M. differentialis (M.differentialis Thomas), American grasshoppers (e.g., Schistocerca americana Drury), desert locusts (Schistocerca gregaria Forskal), migratory locusts (Locusta migratoria Linnaeus), bush locusts (Zonocerus spp.), house crickets (Acheta domesticus Linnaeus), mole crickets (e.g., tawny mole crickets (Scapteriscus vicinus Scudder) and southern mole crickets (Scapteriscus borrelii eggs, adults and juveniles of Orthoptera including leafminers (e.g. Liriomyza spp., e.g. the bean leafminer (Liriomyza sativae Blanchard)), midges, fruit flies (Family Tephritidae), fruit flies (e.g. Oscinella frit Linnaeus), soil maggots, house flies (e.g. Musca domestica Linnaeus), little house flies (e.g. Fannia canicularis Linnaeus, F. femoralis Stein), stable flies (e.g. Stomoxys calcitrans Linnaeus), face flies, horn flies, blow flies (e.g. Chrysomya spp., Phormia spp.) and other blowfly pests, horse flies (e.g. Tabanus spp.), sheep flies (e.g. Gastrophilus spp., Oestrus spp.), cow flies (e.g. Hypoderma spp.), deer flies (e.g. Chrysops spp.),), sheep lice (e.g. Melophagus ovinus Linnaeus) and other Brachycera, mosquitoes (e.g. Aedes spp., Anopheles spp., Culex spp.), blackflies (e.g. Prosimulium spp., Simulium spp.), eggs of Diptera including midges, sand flies, sciarid flies, and other Nematocera. Adults and juveniles of Thysanoptera including onion thrips (Thrips tabaci Lindeman), leaf thrips (Frankliniella spp.), and other leaf-feeding thrips; Florida carpenter ant (Camponotus floridanus Buckley), red carpenter ant (Camponotus ferrugineus Fabricius), Japanese carpenter ant (Camponotus pennsylvanicus De Geer), white-legged ant (Technomyrmex albipes fr. Smith), big-headed ant (Pheidole spp.), sp.), ghost ants (Tapinoma melanocephalum Fabricius); house ants (Monomorium pharaonis Linnaeus), little fire ants (Wasmannia auropunctata Roger), red fire ants (Solenopsis geminata Fabricius), red fire ants (Solenopsis invicta Buren), Argentine ants (Iridomyrmex humilis Mayr), crazy ants (Paratrechina longicornis Latreille), pavement ants (Tetramorium caespitum Insect pests of the order Hymenoptera, including ants of the family Formicidae, including the common ant (Lasius alienus Foerster), the cornfield ant (Lasius alienus Foerster), and the odorous house ant (Tapinoma sessile Say). Bees (including carpenter bees), hornets, yellow jackets, wasps, and sawflies (Neodiprion spp.; other Hymenoptera including Cephus spp.; Termitidae (e.g. Macrotermes sp., Odontotermes obesus Rambur), Kalotermitidae (e.g. Cryptotermes sp.), and Rhinotermitidae (e.g. Reticulitermes sp., Coptotermes sp., Heterotermes tenuis Hagen), Eastern subterranean termites (Reticulitermes flavipes Kollar), Western subterranean termites (Reticulitermes hesperus), and other subterranean termites (Reticulitermes spp.). hesperus (Banks), Formosan termite (Coptotermes formosanus Shiraki), West Indian drywood termite (Incisitermes immigrans Snyder), Powder post termite (Cryptotermes brevis Walker), Drywood termite (Incisitermes snyderi Light), Southeastern subterranean termite (Reticulitermes virginicus Banks), Western drywood termite (Incisitermes minor Hagen), Arboreal termites such as Nasutitermes sp.insect pests of the order Isoptera, including the silverfish (Lepisma saccharina Linnaeus) and other termites of economic importance; insect pests of the order Thysanura, for example the silverfish (Lepisma saccharina Linnaeus) and the silverfish (Thermobia domestica Packard); insect pests of the order Mallophaga, including the head louse (Pediculus humanus capitis De Geer), the human body louse (Pediculus humanus Linnaeus), the chicken louse (Menacanthus stramineus Nitszch), the dog biting louse (Trichodectes canis De Insect pests including the sheep body louse (Bovicola ovis Schrank), the cattle louse (Haematopinus eurysternus Nitzsch), the long-legged cattle louse (Linognathus vituli Linnaeus) and other blood-sucking and biting parasitic lice that attack humans and animals; Insect pests of the order Siphonoptera, including the Oriental rat flea (Xenopsylla cheopis Rothschild), cat flea (Ctenocephalides felis Bouche), dog flea (Ctenocephalides canis Curtis), chicken flea (Ceratophyllus gallinae Schrank), sucking flea (Echidnophaga gallinacea Westwood), human flea (Pulex irritans Linnaeus) and other fleas that infest mammals and birds. Further arthropod pests encompassed include spiders from the order Araneae, such as the brown recluse spider (Loxosceles reclusa Gertsch & Mulaik) and the black widow spider (Latrodectus mactans Fabricius), and centipedes from the order Scutigeromorpha, such as the house centipede (Scutigera coleoptrata Linnaeus).

[0280] Examples of invertebrate pests of stored grain include the long-horn beetle (Prostephanus truncatus), the bark beetle (Rhyzopertha dominica), the rice weevil (Stiophilus oryzae), the corn weevil (Stiophilus zeamais), the cowpea weevil (Callosobruchus maculatus), the red flour beetle (Tribolium castaneum), the granary rice weevil (Stiophilus granarius), the Indian meal moth (Plodia interpunctella), and the rice beetle (Rhyzopertha dominica). interpunctella), the Mediterranean flour beetle (Ephestia kuhniella) and the small or rusty leaf beetle (Cryptolestis ferrugineus).

[0281] The compounds of the present disclosure may be used to combat, but are not limited to, economically important agricultural pests (i.e., Meloidogyne, Pratylenchus, Trichodorus, etc.) as well as animal and human health pests (i.e., Strongylus vulgaris in horses, Toxocara canis in dogs, Haemonchus contortus in sheep, Dirofilaria immitis Leidy in dogs, Anoplocephala perfoliata in horses, Fasciola hepatica in ruminants, and the like). In particular, the present invention may be active against members of the taxa Nematoda, Cestoda, Trematoda, and Acanthocephala, including economically important members of the orders Strongylida, Ascaridida, Oxyurida, Rhabditida, Spirurida, and Enoplida, such as all economically important trematodes, cestodes, and roundworms (e.g., Staphylococcus aureus, Staphylococcus cerevisiae, Staphylococcus aureus, Staphylococcus niger, Staphylococcus niger, and Staphylococcus niger).

[0282] The compounds of the present disclosure are effective against Lepidoptera pests such as Alabama argillacea Huebner (cotton leafworm), Archips argyrospila Walker (fruit tree leaf roller), A. rosana Linnaeus (European leaf roller) and other Archips species, Chilo suppressalis Walker (rice stem borer), Cnaphalocrosis medinalis Guenee (rice leafflorist), Crambus caliginosellus Clemens (corn root webworm), Crambus teterrellus Zincken (bluegrass webworm), Codling moth, Cydia pomonella) Linnaeus (Codling Moth), Earias insulana Boisduval (Spiny Bowl Worm), Earias vittella Fabricius (Spotted Bowl Worm), Helicoverpa armigera Huebner (Bush Moth), Helicoverpa zea Boddie (Tobacco Moth Larva), Heliothis virescens Fabricius (False Tobacco Moth), Herpetogramma licarsisalis Walker (Sod Webworm), Lobesia botrana Denis & Schiffermueller (Grape Berry Moth), Pectinophora gossipiera gossypiella) Saunders (larvae of the pink bollworm), Phyllocnistis citrella) Stainton (citrus leafminer), PierisIt is particularly active against the following insecticides: Pieris rapae Linnaeus (cabbage white), Plutella xylostella Linnaeus (diamond moth), Spodoptera exigua Huebner (beet armyworm), Spodoptera litura Fabricius (common cutworm, cluster caterpillar), Spodoptera frugiperda J. E. Smith (stalk cutworm), Trichoplusia ni Huebner (cabbage looper), and Tuta absoluta Meyrick (tomato leaf miner).

[0283] Compounds of the present disclosure may also have significant activity against members of the order Hemiptera, including Acyrthosiphon pisum Harris (pea aphid), Aphis craccivora Koch (cowpea aphid), Aphis fabae Scopoli (bean aphid), Aphis gossypii Glover (cotton aphid, melon aphid), Aphis pomi De Geer (apple aphid), Aphis spiraecola Patch (spirea aphid), Aulacorthum solani Kaltenbach (foxglove aphid), Chaetosiphon fragaefolii) Cockerell (strawberry aphid), Diuraphis noxia) Kurdjumov / Mordvilko (Russian wheat aphid), Dysaphis plantaginea) Passerini (rose apple aphid), Eriosoma lanigerum) Hausmann (apple aphid), Hyalopterus pruni) Geoffroy (mealy plum aphid), Lipaphis pseudobrassicae) Davis (false radish aphid), Metopolophium dirhodum) Walker (cereal aphid), Macrosiphum euphorbiae)Thomas (potato aphid), Myzus persicae)Sulzer (peach-potato aphid, green peach aphid), Nasonovia ribisnigri)Mosley (lettuce aphid), Pemphigus spp.) (root aphids and leaf aphids), Rhopalosiphum maidis Fitch (corn aphid), Rhopalosiphum padi Linnaeus (bird cherry-oat aphid), Schizaphis graminum Rondani (green-leaf aphid), Sitobion avenae Fabricius (English grain aphid), Therioaphis maculata Buckton (spotted alfalfa aphid), Toxoptera aurantii Boyer de Fonscolombe (black citrus aphid), and Toxoptera citricidus citricidus) Kirkaldy (brown citrus aphid); Adelges spp.)(caps aphid); Phylloxera devastatrix (Pergande); Bemisia tabaci (Bemisia tabaci); Gennadius (Tobacco whitefly, sweet potato whitefly); Silverleaf whitefly (Bemisia argentifolii); Bellows & Perring (Silverleaf whitefly); Dialeurodes citri (Ashmead); Trialeurodes vaporariorum (Trialeurodes vaporariorum); Potato leafhopper (Empoasca fabae); Harris (Potato leafhopper); Small brown planthopper (Laodelphax striatellus)Fallen(Small Brown Planthopper), Macrosteles quadrilineatus)Forbes(Aster Leafhopper), Nephotettix cincticeps)Uhler(Green Rice Leafhopper), Nephotettix nigropictus)Stal(Rice Leafhopper), Nilaparvata lugens)Stal(Brown Planthopper), Peregrinus maidis)Ashmead(Corn Planthopper), Sogatella furcifera)Horvath(White-backed Planthopper), Tagosodes orizicolus)Muir(Rice Delphacid), Typhlocyba pomarialis pomaria) McAtee (White Apple Leafhopper), Erythroneura spp.)(Grape Leafhopper);Magicidada septendecim Linnaeus(Periodic Cicada);Icerya purchasi Maskell(Cotton Scale), Quadraspidiotus perniciosus Comstock(San Jose Scale);Planococcus citri Risso(Citrella mealybug);Pseudococcus spp.(Other mealybug complex);Cacopsylla pyricola Foerster(Pear Psylla),Trioza diospyri Ashmead(Persimmon Psylla). .

[0284] Compounds of the present disclosure also have activity against members of the order Hemiptera, including Acrosternum hilare Say (green stink bug), Anasa tristis De Geer (helicopter bug), Blissus leucopterus leucopterus Say (American long-horned stink bug), Cimex lectularius Linnaeus (bed bug), Corythuca gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), Dysdercus suturellus Herrich-Schaeffer (cotton stainer), Euchistus servus Say (brown stink bug), Euchistus variolarius Palisot de Beauvois (one-spotted stink bug), Graptosthetus spp. (seed bug complex), Halymorpha halys Stal (brown marbled stink bug), Leptoglossus corculus Say (leaf-footed pine seed bug), Lygus lineolaris Palisot de Beauvois (green mistletoe bug), Nezara viridula) Linnaeus (Southern green stink bug), Oebalus pugnax) Fabricius (Rice stink bug), Oncopeltus fasciatus) Dallas (Large milkweed bug), Pseudatomoscelis seriatus) Reuter (Cotton freehopper).Other insect orders controlled by the compounds of the present disclosure include Thysanoptera (e.g., Frankliniella occidentalis Pergande (Occitrus flower thrips), Scirthothrips citri Moulton (Citrella thrips), Sericothrips variabilis Beach (Soybean thrips), and Thrips tabaci Lindeman (Onion thrips); and Coleoptera (e.g., Leptinotarsa ​​decemLineata Say (Colorado potato beetle), Epilachna varivestis (Epilachna varivestis), and the like). varivestis Mulsant (ladybugs) and click beetle larvae of the genera Agriotes, Athous or Limonius.

[0285] Of note is the use of the compounds of the present disclosure to control western flower thrips (Frankliniella occidentalis). Of note is the use of the compounds of the present disclosure to control diamondback moth (Plutella xylostella). Of note is the use of the compounds of the present disclosure to control fall armyworm (Spodoptera frugiperda).

[0286] The compounds of the present disclosure are also useful for increasing the vigor of crop plants. The method includes contacting a crop plant (e.g., leaves, flowers, fruits, or roots) or a seed from which the crop plant grows with a compound of formula 1 in an amount sufficient to achieve a desired plant vigor effect (i.e., a biologically effective amount). Typically, the compound of formula 1 is applied in a formulated composition. The compound of formula 1 is often applied directly to the crop plant or its seed, but it can also be applied to the locus of the crop plant, i.e., to a part of the environment of the crop plant, particularly in close enough proximity to the crop plant for the compound of formula 1 to be transferred to the crop plant. The locus relevant to the method most commonly includes the growth medium in which the plant is grown (i.e., the medium that provides nutrients to the plant), typically soil. Thus, treating a crop plant to increase the vigor of the crop plant includes contacting the crop plant, the seed from which the crop plant grows, or the locus of the crop plant with a biologically effective amount of a compound of formula 1.

[0287] Increased crop vigor can result in one or more of the following observed effects: (a) optimal crop growth as indicated by superior seed germination, crop emergence and crop stand; (b) improved crop growth as indicated by rapid and robust leaf growth (e.g., as measured by Leaf Area Index), plant height, number of tillers (e.g., in the case of rice), root mass and total dry weight of growing parts of the crop; (c) improved crop yield as indicated by time to flowering, flowering duration, number of flowers, total biomass accumulation (i.e., yield) and / or marketability of the fruit or grain grade of the product (i.e., yield quality); (d) improved ability of the crop to resist or prevent infection with plant diseases and infestations by arthropod, nematode or mollusc pests; and (e) improved ability of the crop to resist environmental stresses such as extreme temperatures, suboptimal moisture or exposure to phytotoxic chemicals.

[0288] The compounds of the present disclosure can increase the vigor of treated plants compared to untreated plants by killing or otherwise preventing feeding of phytophagous invertebrate pests in the plant's environment. In the absence of such control of phytophagous invertebrate pests, the pests reduce plant vigor by consuming plant tissue or sap or transmitting plant pathogens such as viruses. The compounds of the present disclosure can also increase plant vigor by modifying plant metabolism even in the absence of phytophagous invertebrate pests. In general, the vigor of crop plants will be most significantly increased by treating the plants with the compounds of the present disclosure when the plants are grown in non-ideal environments, i.e., environments that contain one or more aspects that are unfavorable to the plants achieving the full genetic potential that they would exhibit in ideal environments.

[0289] Of note is a method of the invention for increasing the vigor of a crop plant growing in an environment that includes a herbivorous invertebrate pest. Of note is a method of the invention for increasing the vigor of a crop plant growing in an environment that does not include a herbivorous invertebrate pest. Of note is a method of the invention for increasing the vigor of a crop plant growing in an environment that includes an amount of moisture that is not ideal for supporting the growth of the crop plant. Of note is a method of the invention for increasing the vigor of a crop plant, wherein the crop is rice. Of note is a method of the invention for increasing the vigor of a crop plant, wherein the crop is maize (corn). Of note is a method of the invention for increasing the vigor of a crop plant, wherein the crop is soybean.

[0290] The compounds of the present disclosure can be mixed with one or more other bioactive compounds or agents, including insecticides, fungicides, nematicides, fungicides, acaricides, herbicides, herbicide safeners, growth regulators, such as insect molting inhibitors and root promoters, chemical hemostats, semi-chemicals, repellents, attractants, pheromones, feeding stimulants, other bioactive compounds, or insect pathogenic bacteria, viruses, or fungi, to form multi-component insecticides that provide a broader spectrum of agronomic and non-agronomic utility. Thus, the present disclosure also relates to a composition comprising a biologically effective amount of a compound of formula 1, at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, and at least one additional bioactive compound or agent. With respect to the mixtures of the present disclosure, the other bioactive compounds or agents can be formulated together with the compounds of the present invention, including the compounds of Formula 1, to form a premix, or the other bioactive compounds or agents can be formulated separately from the compounds of the present invention, including the compounds of Formula 1, and the two formulations can be combined together prior to application (e.g., in a spray tank) or alternatively applied sequentially.

[0291] Examples of such biologically active compounds or agents that may be formulated with the compounds of the present disclosure include insecticides such as abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acinonapyr, afidopyropen ([(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-tetrahydro ... trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]cyclopropanecarboxylate), amidoflumet, amitraz, avermectin, azadirachtin, azinphos-methyl, benfuracarb, bensultap, benzpyrimoxane, bifenthrin, kappa-bifenthrin, bifenazate, bistrifluron, borate, broflanilide, buprofezin, cadusafos, carba aryl, carbofuran, cartap, carsol, chlorantraniliprole, chlorfenapyr, chlorfluazuron, chlorprallethrin, chlorpyrifos, chlorpyrifos-e, chlorpyrifos-methyl, chromafenozide, clofentezine, chlorprallethrin, clothianidin, cyantraniliprole (3-bromo-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-1H-pyra azole-5-carboxamide), cyclaniliprole (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), cyenopyrafen, cyflumetofen, cyfluthrin, beta-cyfluthrin, sialodiamide, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dichloromezothiaz, dieldrin, diflubenzuron, dimefluthrin, dimehypo, dimethoate, dipropylidaz, dinotefuran, diofenolan, emamectin, emamectin benzoate , endosulfan, esfenvalerate, ethiprole, etofenprox, epsilon-metofluthrin, etoxazole, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flometoquin (2-ethyl-3,7-dimethyl-6-[4-(trifluoromethoxy)phenoxy]-4-quinolinylmethyl carbonate), flonicamid, fluazaindolizine, flubendiamide, flucythrinate, flufenerim, flumetamine ... Lufenoxuron, Flufenoxystrobin (methyl(αE)-2-[[2-chloro-4-(trifluoromethyl)phenoxy]methyl]-α-(methoxymethylene)benzeneacetate), Fluensulfone (5-chloro-2-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]thiazole), Fluhexafon, Fluopyram, Flupiprole (1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(2-methyl-2-propen-1-yl)amino]-4-[(trifluoromethyl) ethyl)sulfinyl]-1H-pyrazole-3-carbonitrile), flupyradifurone (4-[[(6-chloro-3-pyridinyl)methyl](2,2-difluoroethyl)amino]-2(5H)-furanone), flupirimine, fluvalinate, tau-fluvalinate, fluxamethamide, fonofos, formetanate, fosthiazate, gamma-cyhalothrin, halofenozide, heptafluthrin ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl 2,2-dimethyl-3-[(1Z)-3,3,3-trifluoro-1-propen-1-yl]cyclopropanecarboxylate), hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, indoxacarb, insecticidal soap, isofenphos, isocycloceram, kappa-tefluthrin, lambda-cyhalothrin, lufenuron, malathion, meperfluthrin ([2,3,5.6-tetrafluoro-4-(methoxymethyl)phenyl]methyl(1R,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate), metaflumizone, metaa aldehyde, methamidophos, methidathion, methiocarb, methomyl, methoprene, methoxychlor, metofluthrin, methoxyfenozide, epsilon-metofluthrin, epsilon-momfluorothrin, monocrotophos, monofluorothrin ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl 3-(2-cyano-1-propen-1-yl)-2,2-dimethylcyclopropanecarboxylate), nicotine, nitenpyram, nithiazine, novaluron, noviflumuron, oxamyl, oxazosulfil, parathion , parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, propargite, protrifenbut, piflubumid (1,3,5-trimethyl-N-(2-methyl-1-oxopropyl)-N-[3-(2-methylpropyl)-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl]-1H-pyrazole-4-carboxamide), pymetrozine, pyrafluprole, pyrethrins, pyridaben, pyridalyl, pyrifluquinazo , pyriminostrobin (methyl(αE)-2-[[[2-[(2,4-dichlorophenyl)amino]-6-(trifluoromethyl)-4-pyrimidinyl]oxy]methyl]-α-(methoxymethylene)benzeneacetate), pyriprole, pyriproxyfen, rotenone, ryanodine, silafluofen, spinetoram, spinosad, spirodiclofen, spiromesifen, spiropydione, spirotetramat, sulprofos, sulfoxaflor (N-[methyloxy[1-[6-(trifluoromethyl)-3-pyridinyl]ethyl]-λ, 4-sulfanylidene]cyanamide), tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, kappa-tefluthrin, terbufos, tetrachlorantraniliprole, tetrachlorvinphos, tetramethrin, tetramethylfluthrin ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl 2,2,3,3-tetramethylcyclopropanecarboxylate), tetraniliprole, thiacloprid, thiamethoxam, thiodicarb, thiosulta t-sodium, thioxazaphen (3-phenyl-5-(2-thienyl)-1,2,4-oxadiazole), tolfenpyrad, tralomethrin, triazamate, trichlorfon, triflumezopyrim (2,4-dioxo-1-(5-pyrimidinylmethyl)-3-[3-(trifluoromethyl)phenyl]-2H-pyrido[1,2-a]pyrimidinium inner salt), triflumuron, cyclopyrazoflor, zeta-cypermethrin, Bacillus thuringiensis delta endotoxin, entomopathogenic bacteria, entomopathogenic viruses or entomopathogenic fungi.

[0292] Of note are abamectin, acetamiprid, acrinathrin, acinonapyr, afidopiropen, amitraz, avermectin, azadirachtin, benfuracarb, bensultap, bifenthrin, buprofezin, brofuranilide, cadusafos, carbaryl, cartap, chlorantraniliprole, chlorprallethrin, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, and cyclopropanediol. Halothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, diofenolan, emamectin, endosulfan, epsilon-metofluthrin, esfenvalerate, ethiprole, etofenprox, etoxazole, fenitrothion, fenothiocarb, fenoxycarb, fenvalerate, fipronil, flometoquin, fluxamethamide, flonicamid, flubendiamide, fluensulfone, flufenoxuron, flufenoxystrobin , flufensulfon, flupiprole, flupirimine, flupyradifurone, fluvalinate, formetanate, hosthiazate, gamma-cyhalothrin, heptafluthrin, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, isocycloceram, kappa-tefluthrin, lambda-cyhalothrin, lufenuron, meperfluthrin, metaflumizone, methiodicarb, methomyl, methoprene, methoxyfenozide, metofluthrin, monofluorothrin, nitenpyram, nithiazine, novaluron, oxamyl, piflubumis do, pymetrozine, pyrethrins, pyridaben, pyridalyl, pyriminostrobin, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulfoxaflor, tebufenozide, tetramethrin, tetramethylfluthrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, triflumezopyrim, triflumuron, cyclopyrazoflor, zeta-cypermethrin, Bacillus thuringiensis (Bacillusthuringiensis delta-endotoxin, all strains of Bacillus thuringiensis, and all strains of nucleopolyhedrovirus.

[0293] One embodiment of a biological agent for mixing with the compounds of the present disclosure includes entomopathogenic bacteria, such as Bacillus thuringiensis and encapsulated delta-endotoxin of Bacillus thuringiensis, e.g., MVP® and MVPII® bioinsecticides prepared by the CellCap® process (CellCap®, MVP® and MVPII® are trademarks of Mycogen Corporation, Indianapolis, Indiana, USA); entomopathogenic fungi, such as green muscardine fungus; and entomopathogenic viruses (both naturally occurring and recombinant), such as baculoviruses, nucleopolyhedroviruses (NPV), e.g., Helicoverpa zea nucleopolyhedrovirus (HzNPV), Anagrapha falcifera (Anagrapha falcifera) and entomopathogenic fungi (E. coli). falcifera nucleopolyhedrovirus (AfNPV); and granulosis viruses (GV), such as codling moth (Cydia pomonella granulosis virus (CpGV).

[0294] One embodiment of a biological agent for mixing with a compound of the present disclosure is (i) a species of Actinomycetes, Agrobacterium, Arthrobacter, Alcaligenes, Aureobacterium, Azobacter, Bacillus, Beijerinckia, Bradyrhizobium, or a species of bacteria. The genera Bradyrhizobium, Brevibacillus, Burkholderia, Chromobacterium, Clostridium, Clavibacter, Comamonas, Corynebacterium, Curtobacterium, Enterobacter, robacter, Flavobacterium, Gluconobacter, Hydrogenophaga, Klebsiella, Methylobacterium, Paenibacillus, Pasteuria, Photorhabdus, Phyllobacterium Bacteria of the genera Bacillus subtilis, Bacillus cereus, Bacillus firmus, Bacillus licheniformis, Bacillus erium, Pseudomonas, Rhizobium, Serratia, Sphingobacterium, Stenotrophomonas, Streptomyces, Variovorax, or Xenorhabdus, for example Bacillus amyloliquefaciens, Bacillus cereus, Bacillus firmus, Bacillus licheniformis, Bacillus spp.licheniformis, Bacillus pumilus, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Bradyrhizobium japonicum, Chromobacterium subtsugae, Pasteuria nishizawae, Pasteuria penetrans, Pasteuria usage, Pseudomonas fluorescens, and Streptomyces rhizicus. lydicus bacteria; (ii) fungi, such as Pseudomonas monadella; (iii) viruses, including baculoviruses, nuclear polyhedrosis viruses, such as Helicoverpa zea nuclear polyhedrosis virus, Anagrapha falcifera nuclear polyhedrosis virus; granulosis viruses, such as Cydia pomonella granulosis virus.

[0295] Of particular note are such combinations, where the other invertebrate pest control active ingredient belongs to a different chemical class or has a different site of action than the compound of formula 1. In certain instances, the combination with at least one other invertebrate pest control active ingredient having a similar control spectrum but a different site of action is particularly advantageous for resistance management. Thus, the composition of the present disclosure can further comprise a biologically effective amount of at least one additional invertebrate pest control active ingredient having a similar control spectrum but belonging to a different chemical class or having a different site of action. These additional biologically active compounds or agents include, but are not limited to, acetylcholinesterase (AChE) inhibitors such as the carbamates methomyl, oxamyl, thiodicarb, triazamate, and the organophosphate chlorpyrifos; GABA-gated chloride channel antagonists such as the cyclodienedieldrin and endosulfan, and the phenylpyrazoles ethiprole and fipronil; sodium channel modulators such as the pyrethroids bifenthrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, deltamethrin, dimefluthrin, esfenvalerate, metofluthrin, and profluthrin; nicotinic acetylcholine receptor (nAChR) agonists such as the neonicotinoids acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, and thiamethoxam, and sulfoxaflor; nicotinic acetylcholine receptor (nAChR) allosteric activators such as the spinosyns spinetoram and spinosad; chloride channel activators such as the avermectins abamectin and emamectin; juvenile hormone mimetics such as diofenolan, methoprene, fenoxycarb and pyriproxyfen; selective homopteran feeding blockers such as pymetrozine and flonicamid; mite growth inhibitors such as etoxazole; inhibitors of mitochondrial ATP synthase such as propargite; uncouplers of oxidative phosphorylation by disruption of the proton gradient such as chlorfenapyr; nicotinic acetylcholine receptor (nAChR) channel blockers such as the nereistoxin analogue cartap;Inhibitors of chitin biosynthesis, such as the benzoylureas flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron and triflumuron, and buprofezin; dipteran molting disruptors, such as cyromazine; ecdysone receptor agonists, such as the diacylhydrazines methoxyfenozide and tebufenozide; octopamine receptor agonists, such as amitraz; mitochondrial complex III electron transport inhibitors, such as hydramethylnon; mitochondrial complex I electron transport inhibitors, such as pyridaben; voltage-dependent sodium channel blockers, such as indoxacarb; inhibitors of acetyl CoA carboxylase, such as tetronic acid and tetramic acid spirodichloro. fen, spiromesifen and spirotetramat; mitochondrial complex II electron transport inhibitors such as the β-ketonitriles cyenopyrafen and cyflumetofen; ryanodine receptor modulators such as the anthranilic acid diamides chlorantraniliprole, cyantraniliprole and cyantraniliprole, diamides such as flubendiamide, and ryanodine receptor ligands such as ryanodine; compounds in which the target site involved in the biological activity is unknown or uncharacterized such as azadirachtin, bifenazate, pyridalyl, pyrifluquinazone and triflumezopyrim; microbial disruptors of the insect midgut membrane such as Bacillus thuringensis and the delta endotoxins they produce and Bacillus sphaericus; and biological agents including nuclear polyhedrosis virus (NPV) and other natural or recombinant insecticidal viruses;

[0296] Further examples of biologically active compounds or agents that may be combined with the compounds of the present disclosure are: fungicides, such as acibenzolar-S-methyl, aldimorph, amethoctrazine, aminopyrifen, amisulbrom, anilazine, azaconazole, azoxystrobin, benalaxyl (including benalaxyl-M), benodanil, benomyl, benthiavalicarb (including benthiavalicarb-isopropyl), benzovindiflupyr, bethoxadin, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, boscalid, bromocobalamin ... nazole, bupirimate, buthiobate, carboxin, carpropamid, captafol, captan, carbendazim, chloroneb, chlorothalonil, chlozolinate, copper hydroxide, copper oxychloride, copper sulfate, cumoxystrobin, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, diclobenthiazox, dichlofluanid, diclocymet, diclomedine, dicloran, diethofencarb, difenoconazole, diflumetrim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole (diniconazole) (including tetracycline-M), dinocap, dipimethitron, dithianone, dithiolane, dodemorph, dodine, econazole, etaconazole, edifenphos, enoxastrobin (also known as enesterobulin), epoxiconazole, ethaboxam, ethirimol, etridiazole, famoxadone, fenamidone, phenaminestrobin, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fenpicoxamid, fenpropidin, fenpropimorph, fenpyrazamine, threonine acetate ... Triphenyltin, triphenyltin hydroxide, ferbam, ferimzone, flometoquin, florylpicoxamide, fluopimomide, fluazinam, fludioxonil, flufenoxystrobin, fluindapyr, flumorph, fluopicolide, fluopyram, fluoxapiproline, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, fthalide (also known as phthalide), fuberidazole, furalaxyl, furametpyr,Hexaconazole, Hymexazole, Guazatine, Imazalil, Imibenconazole, Iminoctadine albesilate, Iminoctadine triacetate, Impilfluxam, Iodicarb, Ipconazole, Ipfentrifluconazole, Ipflufenoquine, Isofetamide, Iprobenfos, Iprodione, Iprovalicarb, Isoflucipram, Isoprothiolane, Isopyrazam, Isotianil, Kasugamycin, Kresoxim-methyl, Lancotrione, Mancozeb, Mandipropamide, Mandestrobin, Maneb, Mapanipirin, Mefentri Fluconazole, mepronil, meptyldinocap, metalaxyl (including metalaxyl-M / mefenoxam), metconazole, methasulfocarb, metiram, metominostrobin, methyltetraprole, metrafenone, myclobutanil, naphthitine, neo-asodine (ferrous methanearsonate), nuarimol, octhilinone, ofrace, oryzastrobin, oxadixyl, oxathiapiproline, oxolinic acid, oxypoconazole, oxycarboxin, oxytetracycline, penconazole, pencycuron, penflufen, penthio Pyrad, perfurazoate, phosphorous acid (including its salts, e.g., fosetyl-aluminium), picoxystrobin, piperalin, polyoxins, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, proquinazid, prothiocarb, prothioconazole, pydiflumetofen (Adepidyn®), pyraclostrobin, pyrametostrobin, pyrapropoin, pyroxystrobin, pyraziflumid, pyrazophos, pyribencarb, pyributacarb, pyridaclomethyl, pyrifenox, Pyrrophenone, perisoxazole, pyrimethanil, pyrifenox, pyrrolnitrin, pyroquilon, quinconazole, quinomethionate, quinofumelin, quinoxyfen, quintozene, silthiofam, sedaxane, simeconazole, spiroxamine, streptomycin, sulfur, tebuconazole, tebufloquine, tecloftalam, tecloftalam, tecnazene, terbinafine, tetraconazole, thiabendazole, thifluzamide, thiophanate, thiophanate-methyl, thiram, thiadinil, tolclofos-methyl, tolprocarb,Trifluanid, triadimefon, triadimenol, triarimol, triazoxide, tribasic copper sulfate, triclopyricarb, tridemorph, trifloxystrobin, triflumizole, trimopramidotricyclazole, trifloxystrobin, triforine, triticonazole, uniconazole, validamycin, valifenalate (also known as valifenal), vinclozolin, zineb, ziram, zoxamide and 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-methyl-2-propanol. -piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone; nematocides, such as fluopyram, spirotetramat, thiodicarb, fosthiazate, abamectin, iprodione, fluensulfone, dimethyl disulfide, thioxazaphen, 1,3-dichloropropene (1,3-D), metam (sodium and potassium), dazomet, chloropicrin, fenamiphos, ethoprophos, cadusafos, terbufos, imicyafos, oxamyl, carbofuran, thioxazaphen, Bacillus firmus (Bacillus firmus and Pasteuria nishizawae; fungicides such as streptomycin; acaricides such as amitraz, quinomethionate, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad.

[0297] In certain instances, the combination of the compounds of the present disclosure with other bioactive (particularly invertebrate pest control) compounds or agents (i.e., active ingredients) can result in improved effectiveness.While ensuring effective pest control, it is always desirable to reduce the amount of active ingredient released into the environment.If enhanced invertebrate pest control occurs at an application rate that provides an agronomically satisfactory level of invertebrate pest control, such a combination can be advantageous in terms of reducing crop production costs and reducing environmental burden.

[0298] The compounds and compositions of the present disclosure may be applied to plants genetically transformed to express proteins toxic to invertebrate pests (such as Bacillus thuringiensis delta endotoxin). Such application may provide broader spectrum plant protection and may be advantageous for resistance management. Exogenously applied invertebrate pest control compounds of the present disclosure in combination with the expressed toxin protein may provide improved efficacy.

[0299] General references for these agricultural protection agents (i.e. insecticides, fungicides, nematicides, acaricides, herbicides and biological agents) include The Pesticide Manual, 13th Edition, CDS Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, UK, 2003 and The BioPesticide Manual, 2004. nd Edition, LG Copping, Ed., British Crop Protection Council, Farnham, Surrey, UK, 2001.

[0300] The compounds of the present disclosure may be combined or formulated with polynucleotides, including, but not limited to, DNA, RNA, and / or chemically modified nucleotides, that affect the abundance of specific targets by downregulating, interfering, suppressing or silencing genetically derived transcripts that confer an insecticidal effect.

[0301] For embodiments in which one or more of these various mixing partners are used, the weight ratio (total) of these various mixing partners to the compound of formula 1 is typically about 1:3000 to about 3000:1. Of note is a weight ratio of about 1:300 to about 300:1 (e.g., a ratio of about 1:30 to about 30:1). Those skilled in the art can easily determine the biologically effective amount of active ingredient required to obtain the desired spectrum of biological activity by simple experimentation. It will be apparent that the inclusion of these additional ingredients allows the spectrum of invertebrate pests to be controlled to be broader than that controlled by the compound of formula 1 alone.

[0302] Invertebrate pests are controlled in agronomic and non-agronomic applications by applying one or more compounds of the present disclosure, typically in the form of a composition, in a biologically effective amount to the pest's environment, including agronomic and / or non-agronomic loci, to the area to be protected, or directly to the pest to be controlled.

[0303] Thus, the present disclosure includes methods for controlling invertebrate pests in agricultural and / or non-agricultural applications comprising contacting the invertebrate pest or its environment with a biologically effective amount of one or more of the compounds of the present disclosure, or a composition comprising at least one such compound, or a composition comprising at least one such compound and a biologically effective amount of at least one additional biologically active compound or agent. Examples of suitable compositions comprising a compound of the present disclosure and a biologically effective amount of at least one additional biologically active compound or agent include granular compositions in which the additional active compound is present on the same granule as the compound of the present disclosure or on a separate granule from that of the compound of the present disclosure.

[0304] To achieve contact with a compound or composition of the present disclosure for protecting agricultural crops from invertebrate pests, the compound or composition is typically applied to the seed of the crop prior to planting, to the foliage (e.g., leaves, stems, flowers, fruits) of the crop plant, or to the soil or other growing medium before or after planting the crop.

[0305] One embodiment of the contact method is by spraying. Alternatively, a granular composition comprising the compound of the present disclosure can be applied to the foliage or soil of the plant. The compound of the present disclosure can also be effectively delivered via plant ingestion by contacting the plant with a composition comprising the compound of the present disclosure applied as a soil drench of a liquid formulation, a granular formulation to the soil, a nursery box treatment, or a transplant dipping. Of note is the composition of the present disclosure in the form of a soil drench liquid formulation. Also of note is a method for controlling invertebrate pests, comprising contacting the invertebrate pest or its environment with a biologically effective amount of the compound of the present disclosure or a composition comprising a biologically effective amount of the compound of the present disclosure. Of further note is the method in which the environment is soil and the composition is applied to the soil as a soil drench formulation. Of further note is that the compound of the present disclosure is also effective by localized application to the infested locus. Other contact methods include application of the compounds or compositions of the present disclosure by direct and residual sprays, aerial sprays, gels, seed dressings, microencapsulation, systemic ingestion, baits, ear tags, boluses, sprayers, fumigators, aerosols, dusts and many others. One embodiment of the contact method is a dimensionally stable fertilizer granule, bar or tablet containing the compounds or compositions of the present disclosure. The compounds of the present disclosure can also be impregnated into the materials of construction of invertebrate control devices (e.g., insect nets).

[0306] The compounds of the present disclosure are useful for treating all plants, plant parts and seeds. Plant and seed varieties and cultivars can be obtained by traditional propagation and breeding methods or by genetic engineering methods. A transgenic plant or seed (transgenic plant or seed) is one in which a heterologous gene (transgene) has been stably integrated into the genome of the plant or seed. A transgene defined by its specific location in the plant genome is called a transformation or transgenic event.

[0307] Transgenic plants and seed cultivars that can be treated according to the present disclosure include those that are tolerant to one or more biotic (pests such as nematodes, insects, mites, fungi, etc.) or abiotic (drought, low temperature, soil salinity, etc.) stresses or contain other desirable traits. Plants and seeds can be genetically modified to exhibit, for example, herbicide tolerance, insect resistance, improved oil profile, or drought tolerance traits. Useful transgenic plants and seeds containing single genetic transformation events or combinations of transformation events are listed in Table Z. Further information on the transgenics listed in Table Z can be obtained from the following databases: http: / / www2.oecd.org / biotech / byidentifier.aspx http: / / www.aphis.usda.go http: / / gmoinfo.jrc.ec.europa.eu

[0308] The following abbreviations are used in Table Z below: tol. is resistance, res. is resistance, SU is sulfonylurea, ALS is acetolactate synthase, HPPD is 4-hydroxyphenylpyruvate dioxygenase, and NA is not applicable.

[0309] [Table 21]

[0310] [Table 22]

[0311] [Table 23]

[0312] [Table 24]

[0313] [Table 25]

[0314] [Table 26]

[0315] [Table 27]

[0316] [Table 28]

[0317] [Table 29]

[0318] [Table 30]

[0319] By treating transgenic plants and seeds with the compounds of the present disclosure, improved effects can be obtained, such as reduced application rates, broadened spectrum of activity, increased resistance to biotic / abiotic stresses or improved storage stability, which may be greater than would be expected from a simple additive effect of applying the compounds of the present disclosure to transgenic plants and seeds.

[0320] The compounds of the present disclosure are also useful in seed treatments to protect the seeds from invertebrate pests. In the context of this disclosure and claims, treating the seeds means contacting the seeds with a biologically effective amount of the compounds of the present disclosure, typically formulated as a composition of the present disclosure. This seed treatment protects the seeds from invertebrate soil pests and can also protect the roots and other plant parts that typically come into contact with the soil of the seedlings that emerge from the germinated seeds. This seed treatment can also provide foliar protection by translocation of the compounds of the present disclosure or a second active ingredient within the developing plant. Seed treatments can be applied to all types of seeds, including seeds from which plants that have been genetically transformed to express special traits are germinated. Representative examples include those that express proteins toxic to invertebrate pests, such as Bacillus thuringiensis toxins, or those that express herbicide resistance, such as glyphosate acetyltransferase, which confers resistance to glyphosate. Seed treatment with the compounds of the present disclosure can also increase the vigor of plants grown from the treated seeds.

[0321] One method of seed treatment is by spraying or dusting the seed with the compound of the present disclosure (i.e., as a formulated composition) before sowing the seed. The composition formulated for seed treatment generally includes a film former or adhesive. Thus, typically, the seed coating composition of the present disclosure includes a biologically effective amount of the compound of formula 1, its N-oxide or salt, and a film former or adhesive. The seed can be coated by spraying a flowable suspension concentrate directly onto a tumbling bed of seeds and then drying the seeds. Alternatively, other formulation types such as wettable powders, solutions, suspoemulsions, emulsifiable concentrates, and emulsions in water can be sprayed onto the seeds. This process is particularly useful for applying film coatings to the seeds. A variety of coating machines and processes are available to those skilled in the art. Suitable processes include those listed in P. Kosters et al., Seed Treatment: Progress and Prospects, 1994 BCPC Mongraph No. 57 and references listed therein.

[0322] The compounds of formula 1 and compositions thereof, alone and in combination with other insecticides and fungicides, are particularly useful in seed treatment of crops including, but not limited to, corn or corn, soybeans, cotton, cereals (e.g., wheat, oats, barley, rye and rice), potatoes, vegetables and rapeseed.

[0323] Other insecticides which may be combined with the compounds of Formula 1 to provide mixtures useful for seed treatment include abamectin, acetamiprid, acrinathrin, amitraz, avermectin, azadirachtin, bensultap, bifenthrin, buprofezin, carbaryl, carbofuran, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenothiocarb, fenoxycarb, phen ... , fenvalerate, fipronil, flonicamid, flubendiamide, flufenoxuron, fluvalinate, formetanate, fosthiazate, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, lufenuron, metaflumizone, methiocarb, methomyl, methoprene, methoxyfenozide, nitenpyram, nithiazine, novaluron, oxamyl, pymetrozine, pyrethrins, pyridaben, pyridalyl, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulfoxaflor, tebufenozide, tetramethrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, triflumuron, Bacillus thuringiensis (Bacillus Examples of Bacillus thuringiensis delta-endotoxin, all strains of Bacillus thuringiensis and all strains of nuclear polyhedrosis virus.

[0324] Fungicides which may be combined with the compounds of formula 1 to provide mixtures useful for seed treatment include amisulbrome, azoxystrobin, boscalid, carbendazim, carboxin, cymoxanil, cyproconazole, difenoconazole, dimethomorph, fluazinam, fludioxonil, fluquinconazole, fluopicolide, fluoxastrobin, flutriafol, fluxapyroxad, ipconazole, iprodione, metalaxyl, mefenoxam, metconazole, myclobutanil, paclobutrazol, penflufen, picoxystrobin, prothioconazole, pyraclostrobin, sedaxane, silthiofam, tebuconazole, thiabendazole, thiophanate-methyl, thiram, trifloxystrobin and triticonazole.

[0325] Compositions containing a compound of formula 1 useful for seed treatment may further include bacteria such as Bacillus pumilus (e.g., strain GB34) and Bacillus firmus (e.g., isolate 1582), rhizobia inoculants / extenders, isoflavonoids and lipo-chitooligosaccharides.

[0326] Treated seeds typically contain a compound of the present disclosure in an amount of about 0.1 g to 1 kg per 100 kg of seed (i.e., about 0.0001 to 1% by weight of the seed before treatment). Flowable suspensions formulated for seed treatment typically contain about 0.5 to about 70% active ingredient, about 0.5 to about 30% film-forming adhesive, about 0.5 to about 20% dispersant, 0 to about 5% thickener, 0 to about 5% pigment and / or dye, 0 to about 2% defoamer, 0 to about 1% preservative, and 0 to about 75% volatile liquid diluent.

[0327] The compounds of the present disclosure may be incorporated into bait compositions that are consumed by invertebrate pests or used in devices such as traps, bait stations, etc. Such bait compositions may be in the form of granules that contain (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, and optionally (d) one or more humectants. Of note are granules or bait compositions that contain about 0.001-5% active ingredient, about 40-99% food material and / or attractant; and optionally about 0.05-10% humectant, that are effective in controlling soil invertebrate pests at very low application rates, especially at doses of active ingredient that are lethal by ingestion rather than by direct contact. Some food materials can function as both a food source and an attractant. Food materials include carbohydrates, proteins, and lipids. Examples of food materials are vegetable flour, sugar, starch, animal fat, vegetable oil, yeast extract and milk solids. Examples of attractants are fragrances and flavorings, such as fruit or plant extracts, fragrances, or other animal or plant ingredients, pheromones or other agents known to attract target invertebrate pests. Examples of humectants, i.e., moisture-retaining agents, are glycols and other polyols, glycerin and sorbitol. Of note is a bait composition (and a method of using such a bait composition) used to control at least one invertebrate pest selected from the group consisting of ants, termites and cockroaches. A device for controlling invertebrate pests can include the bait composition of the present invention and a housing configured to contain the bait composition, where the housing has at least one opening sized to allow the invertebrate pest to pass therethrough, thereby allowing the invertebrate pest to access the bait composition from a location outside the housing, and the housing is further configured to be placed at or near a location of possible or known activity of the invertebrate pest.

[0328] The compounds of the present disclosure may be applied without other adjuvants, but in most cases, application is the application of a formulation containing one or more active ingredients together with suitable carriers, diluents, and surfactants, and optionally in combination with food depending on the envisaged end use. One application method involves spraying a water dispersion or refined oil solution of the compounds of the present disclosure. Combinations with spray oils, spray oil concentrates, spreader stickers, adjuvants, other solvents, and piperonyl butoxide often improve compound efficacy. For non-agricultural use, such sprays can be applied from a spray container, such as a can, bottle, or other container, by pumping or by releasing it from a pressurized container, for example, a pressurized aerosol spray can. Such spray compositions can take various forms, such as sprays, mist, foams, fog, or mist. Thus, such spray compositions may optionally further include propellants, foaming agents, and the like. Of note are spray compositions that include a biologically effective amount of the compounds or compositions of the present disclosure and a carrier. An embodiment of such a spray composition comprises a biologically effective amount of the compound or composition of the present disclosure and a propellant. Representative propellants include, but are not limited to, methane, ethane, propane, butane, isobutane, butene, pentane, isopentane, neopentane, pentene, hydrofluorocarbons, chlorofluorocarbons, dimethyl ether, and mixtures of the above. Of note is the spray composition (and the method of using such a spray composition dispensed from a mist container) used to control at least one invertebrate pest, individually or in combination, selected from the group consisting of mosquitoes, black flies, stable flies, deer flies, horseflies, wasps, yellow jackets, hornets, ticks, spiders, ants, blackflies, etc.

[0329] One embodiment of the present disclosure relates to a method for controlling invertebrate pests, comprising diluting a pesticidal composition of the present disclosure (a compound of Formula 1 formulated with a surfactant, a solid diluent, and a liquid diluent, or a combined mixture of a compound of Formula 1 and at least one other pesticide) with water, optionally adding an adjuvant to form a diluted composition, and contacting an invertebrate pest or its environment with an effective amount of the diluted composition.

[0330] Although the spray composition formed by diluting a sufficient concentration of the pesticidal composition of the present invention with water is fully effective in controlling invertebrate pests, it is also possible to add a separately formulated adjuvant product to the spray tank mix. These additional adjuvants are generally known as "spray adjuvants" or "tank mix adjuvants" and include any material mixed in the spray tank to improve the performance of the pesticide or to change the physical properties of the spray mixture. The adjuvants may be surfactants, emulsifiers, petroleum-based crop oils, crop-derived seed oils, acidifiers, buffers, thickeners or antifoaming agents. Adjuvants are used to improve efficacy (e.g., bioavailability, adhesion, penetration, uniformity of coverage and durability of protection) or to minimize or eliminate spray application problems related to incompatibility, foaming, drift, evaporation, volatilization and decomposition. To obtain optimal performance, adjuvants are selected with respect to the properties of the active ingredient, the formulation and the target (e.g., crop, insect pest).

[0331] Among the spray adjuvants, oils including crop oils, crop oil concentrates, vegetable oil concentrates and methylated seed oil concentrates are most commonly used to improve the effectiveness of pesticides, in some cases by promoting more uniform and homogeneous spray deposits.In situations where the plant toxicity potentially caused by oil or other water-immiscible liquids is a concern, the spray composition prepared from the composition of the present disclosure will generally not contain oil-based spray adjuvants.However, in situations where the plant toxicity caused by oil-based spray adjuvants is not commercially significant, the spray composition prepared from the composition of the present invention may also contain oil-based spray adjuvants, which can potentially further increase the control of invertebrate pests, as well as rain resistance.

[0332] Products identified as "crop oil" typically contain 95-98% paraffin or naphtha-based petroleum and 1-2% of one or more surfactants that function as emulsifiers. Products identified as "crop oil concentrates" typically consist of 80-85% emulsifiable petroleum-based oil and 15-20% nonionic surfactants. Products correctly identified as "vegetable oil concentrates" typically consist of 80-85% vegetable oil (i.e., seed or fruit oil, most commonly from cotton, linseed, soybean or sunflower) and 15-20% nonionic surfactants. Adjuvant performance can be improved by replacing the vegetable oil with methyl esters of fatty acids typically derived from the vegetable oil. Examples of methylated seed oil concentrates include MSO® Concentrate (UAP-Loveland Products, Inc.) and Premium MSO Methylated Spray Oil (Helena Chemical Company).

[0333] The amount of adjuvant added to the spray mixture generally does not exceed about 2.5% by volume, and more typically the amount is about 0.1 to about 1% by volume. The application rate of the adjuvant added to the spray mixture is generally about 1 to 5 L per hectare. Representative examples of spray adjuvants include Adigor® (Syngenta) 47% methylated rapeseed oil liquid hydrocarbon, Silwet® (Helena Chemical Company) polyalkylene oxide modified heptamethyltrisiloxane, and Assist® (BASF) 17% surfactant blend in 83% paraffin-based mineral oil.

[0334] Nonagronomic applications include protecting animals, particularly vertebrates, more particularly warm-blooded vertebrates (e.g., mammals or birds) and most particularly mammals, from invertebrate parasitic pests by administering to the animal to be protected a parasiticidally effective (i.e., biologically effective) amount of a compound of the present disclosure, typically in the form of a composition formulated for the animal. Of note, therefore, is a method for protecting an animal, comprising administering to the animal a parasiticidally effective amount of a compound of the present disclosure. As referred to in this disclosure and claims, the terms "parasiticidal" and "parasitically" refer to an observable effect on an invertebrate parasitic pest to provide protection for the animal from the pest. A parasiticidal effect typically relates to reducing the occurrence or activity of the target invertebrate parasitic pest. Such effects on the pest include necrosis, death, growth retardation, reduced motility or reduced ability to persist on or within the host animal, reduced feeding, and inhibited reproduction. These effects on invertebrate parasitic pests provide control (including prevention, reduction or elimination) of parasitic proliferation or infection in animals. Examples of invertebrate parasitic pests that may be controlled by administering a parasitically effective amount of a compound of the present disclosure to a protected animal include ectoparasites (arthropods, acarines, etc.) and endoparasites (parasitic helminths, e.g., nematodes, trematodes, cestodes, thorny headed worms, etc.). In particular, the compounds of the present disclosure are effective against ectoparasites including: flies, such as Haematobia (Lyperosia) irritans (horn fly), Stomoxys calcitrans (stable fly), Simulium spp. (gnats), Glossina spp. (tsetse flies), Hydrotaea irritans (head fly), Musca autumnalis (face fly), Musca domestica (house fly), Morellia simplex (sweat fly), Tabanus spp.) (horse flies), Hypoderma bovis, Hypoderma lineatum, Lucilia sericata, Lucilia cuprina (green blowflies), Calliphora spp. (blowflies), Protophormia spp., Oestrus ovis (sheep flies), Culicoides spp. (midgets), Hippobosca equine, Gastrophilus instestinalis, Gastrophilus haemorrhoidalis and Gastrophilus naslis; lice, for example, Bovicola (Damalinia) bovis, Bovicola equi, Haematopinus asini, Felicola subrostratus, Heterodoxus spiniger, Lignonathus setosus and Trichodectes canis; sheep lice, for example, Melophagus ovinus; mites, for example, Psoroptes spp., Sarcoptes scabei, Chorioptes bovis, Demodex equi, equi, Cheyletiella spp., Notoedres cati, Trombicula spp. and Otodectes cyanotis (ear mites); Ticks, e.g. Ixodes spp., Boophilus spp.), Rhipicephalus spp., Amblyomma spp., Dermacentor spp., Hyalomma spp. and Haemaphysalis spp.; and fleas, for example Ctenocephalides felis (cat flea) and Ctenocephalides canis (dog flea).

[0335] Non-agricultural applications in the veterinary field can be by conventional means, for example, enteral administration in the form of tablets, capsules, drinks, douche preparations, granules, pastes, boluses, feed-through procedures, or suppositories; or parenteral administration, for example, by injection (including intramuscular, subcutaneous, intravenous, intraperitoneal) or implant; by nasal administration; by topical administration, for example in the form of a dip or immersion, spray, wash, coating with a powder, or application to a small area of ​​an animal, and via an article comprising a compound or composition of the present disclosure, for example, a collar, ear tag, tail band, leg band, or halter.

[0336] Typically, a parasiticidal composition according to the present disclosure comprises a mixture of a compound of formula 1, its N-oxide or salt, and one or more pharma- ceutically or veterinarily acceptable carriers, including excipients and auxiliaries, selected with respect to the intended route of administration (e.g., oral, topical or parenteral administration, e.g., injection), and according to standard practice. Furthermore, a suitable carrier is selected based on compatibility with one or more active ingredients in the composition, including considerations such as stability to pH and moisture content. Thus, of note is a composition for protecting animals from invertebrate parasitic pests, comprising a parasitically effective amount of a compound of the present disclosure and at least one carrier.

[0337] For parenteral administration, including intravenous, intramuscular and subcutaneous injection, the compounds of the present disclosure may be formulated in suspension, solution or emulsion in oily or aqueous vehicles and may contain auxiliary agents such as suspending, stabilizing and / or dispersing agents. Pharmaceutical compositions for injection preferably comprise aqueous solutions of a water-soluble form of the active ingredient (e.g., a salt of the active compound) in a physiologically compatible buffer containing other excipients or auxiliary agents as are known in the art of pharmaceutical formulation.

[0338] For oral administration in the form of solutions (the most readily available form for absorption), emulsions, suspensions, pastes, gels, capsules, tablets, boluses, powders, granules, rumen-retention and feed / water / lick blocks, the compounds of the present disclosure can be formulated with binders / fillers known in the art to be suitable for oral administration compositions, such as sugars (e.g., lactose, sucrose, mannitol, sorbitol), starches (e.g., corn starch, wheat starch, rice starch, potato starch), cellulose and derivatives (e.g., methylcellulose, carboxymethylcellulose, ethylhydroxycellulose), protein derivatives (e.g., zein, gelatin), and synthetic polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone). Lubricants (e.g., magnesium stearate), disintegrants (e.g., cross-linked polyvinylpyrrolidinone, agar, alginic acid) and dyes or pigments can be added as needed. Pastes and gels also often contain adhesives (e.g., acacia, alginate, bentonite, cellulose, xanthan gum, colloidal magnesium aluminum silicate) that help the composition maintain contact with the oral cavity and not be easily expelled.

[0339] When the parasiticidal 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 parasiticidal active ingredient, additives that promote animal health or growth, improve meat quality from animals for slaughter, or are otherwise useful for animal husbandry. These additives may include, for example, vitamins, antibiotics, chemotherapeutic agents, bacteriostatic agents, fungistatic agents, coccidiostatic agents, and hormones.

[0340] It has been discovered that the compounds of the present disclosure have favorable pharmacokinetic and pharmacodynamic properties that allow for systemic availability from oral administration and ingestion.Therefore, after ingestion by the animal to be protected, the parasiticidal concentration of the compounds of the present disclosure in the bloodstream protects the treated animal from blood-sucking pests, such as fleas, ticks and lice.Therefore, of note is a composition for protecting animals from invertebrate parasitic pests, in a form for oral administration (i.e., comprising a parasiticidal amount of the compounds of the present disclosure, in addition to one or more carriers selected from binders and fillers suitable for oral administration, and feed concentrate carriers).

[0341] Formulations for topical administration are typically in the form of powders, creams, suspensions, sprays, emulsions, foams, pastes, aerosols, ointments, salves or gels. More typically, topical formulations are aqueous solutions that may be in the form of concentrates that are diluted before use. Parasiticidal compositions suitable for topical administration typically include the compounds of the present disclosure and one or more topically suitable carriers. In topical application of parasiticidal compositions to the exterior of an animal as a line or spot (i.e., "spot-on" treatment), the active ingredient migrates across the surface of the animal to cover most or all of its exterior surface area. As a result, the treated animal is particularly protected from invertebrate pests that infest the animal's epidermis, such as ticks, fleas and lice. Thus, formulations for topical administration often include at least one organic solvent that facilitates the transport of the active ingredient across the skin and / or penetration into the epidermis of the animal. Solvents commonly used as carriers in such formulations include propylene glycol, paraffins, aromatics, esters such as isopropyl myristate, glycol ethers, and alcohols such as ethanol and n-propanol.

[0342] The application rate required for effective control (i.e., "biologically effective amount") depends on factors such as the species of invertebrate to be controlled, the life cycle of the pest, its life stage, its size, location, time of year, host crop or animal, feeding behavior, reproductive behavior, ambient humidity, temperature, etc. Under normal circumstances, an application rate of about 0.01 to 2 kg of active ingredient per hectare is sufficient to control pests in agricultural ecosystems, although as little as 0.0001 kg / hectare may be sufficient, or as much as 8 kg / hectare may be required. For non-agricultural applications, effective application rates range from about 1.0 to 50 mg / m2, although as little as 0.1 mg / m2 may be sufficient, or as much as 150 mg / m2 may be required. Those skilled in the art can readily determine the biologically effective amount required for the desired level of invertebrate pest control.

[0343] In general, for use in veterinary medicine, the compound of formula 1, its N-oxide or salt is administered to the animal to be protected from the invertebrate parasitic pest in a parasitically effective amount. A parasitically effective amount is the amount of active ingredient required to achieve an observable effect, reducing the appearance or activity of the target invertebrate parasitic pest. Those skilled in the art will understand that the parasitically effective dose may vary for various compounds and compositions of the present disclosure, the desired parasitic effect and duration, the target invertebrate pest species, the animal to be protected, the method of application, etc., and the amount required to achieve a particular result can be determined by simple experimentation.

[0344] For oral administration to warm-blooded animals, the daily dosage of the compounds of the present disclosure typically ranges from about 0.01 mg / kg to about 100 mg / kg, more typically from about 0.5 mg / kg to about 100 mg / kg of animal body weight. For topical (e.g., skin) administration, dips and sprays typically contain from about 0.5 ppm to about 5000 ppm, more typically from about 1 ppm to about 3000 ppm, of the compounds of the present disclosure.

[0345] Compounds of the disclosure prepared by the methods described herein are shown in Index Table A. Me means methyl, Et means ethyl, and c-Pr means cyclo-propyl. The abbreviation "Cmpd.No." stands for "Compound Number," and "Ex." stands for "Example," followed by a number indicating in which example the compound was prepared. The abbreviation "mp" stands for "melting point." A wavy line or "-" in a structural fragment indicates the attachment point of the fragment to the remainder of the molecule. The values ​​reported in the "MS" column are those with the highest isotopic abundance H in the molecule. + The most abundant positively charged parent ion (M+1) formed by the addition of (molecular weight 1) or H + is the molecular weight of the most abundant negatively charged ion (M-1) formed by the loss of one or more isotopes of lower abundance (e.g., 37 Cl, 81The presence of molecular ions containing Br is not reported. The reported MS peaks were observed by mass spectrometry using electrospray ionization (ESI) or atmospheric pressure chemical ionization (APCI).

[0346] index table A [ka]

[0347] [Table 31]

[0348] [Table 32]

[0349] Index table B [ka]

[0350] [Table 33]

[0351] index table C [ka]

[0352] [Table 34]

[0353] The following tests demonstrate the control efficacy of the compounds of the present disclosure against certain pests. "Control efficacy" refers to the inhibition of the development (including mortality) of invertebrate pests, resulting in significantly reduced feeding. However, the pest control provided by the compounds of the present invention is not limited to these species. For compound descriptions, see Index Table A.

[0354] Biological Examples Mixture and spray method for tests A to H Test compounds were formulated using a solution containing 10% acetone, 90% water, and 300 ppm Activator 90® non-ionic surfactant (Loveland Products, Loveland, Colorado, USA). The formulated compounds were applied in 1 mL of liquid through an atomizing nozzle positioned 0.5 inches above the top of each test unit. Test compounds were sprayed at the indicated amounts, and each test was repeated three times.

[0355] Test A To evaluate control of diamondback moth (Plutella xylostella L.) by contact and / or systemic means, each test unit consisted of a small open container with a 10-12 day old mustard plant inside.

[0356] Test compounds were formulated and sprayed at 250, 50, 10 and 2 ppm in triplicate as described above. After spraying, the test units were allowed to dry for 1 hour and then infested with 30-50 nymphs. A black obscuring cap was placed on top of each container. The test units were kept in a growth box at 24-25°C and 70% relative humidity for 6 days. Feeding damage was then visually assessed based on ingested stems and larvae were assessed for mortality.

[0357] Of the compounds of Formula 1 tested at 250 ppm, the following provided very good to excellent levels of control efficacy (20% or less feeding damage): 2, 3, 4, 5, 6, 7, 8, 9, 12, 13, 14, 15, 16, 17, 18, 19, 20, 22, 23, 27, 29, 30, 32, 33, 45, 46, 47, 48, 49, 50, 51, 52, 54, 56, 58, 59, 61, 62, 67, 68, 69, 70, and 72.

[0358] Of the compounds of Formula 1 tested at 50 ppm, the following provided very good to excellent levels of control efficacy (20% or less feeding damage): 2, 3, 4, 5, 6, 9, 10, 11, 13, 14, 15, 17, 18, 19, 20, 23, 27, 29, 30, 33, 34, 35, 36, 37, 38, 39, 48, 50, 51, 56, 58, 59, 61, 63, 64, 67, 68, 69, and 72.

[0359] Of the compounds of Formula 1 tested at 10 ppm, the following provided very good to excellent levels of control efficacy (20% or less feeding damage): 2, 3, 4, 5, 9, 10, 11, 13, 14, 15, 18, 19, 20, 23, 27, 29, 33, 38, 50, 56, 63, 64, 67, and 72.

[0360] Of the compounds of Formula 1 tested at 2 ppm, the following provided very good to excellent levels of control efficacy (20% or less feeding damage): 2, 4, 9, 10, 11, 13, 15, 19, 27, 29, 50, 56, 67, and 72.

[0361] Test B To evaluate control of fall armyworm (Spodoptera frugiperda (J.E. Smith)), the test unit consisted of a small open container with a 4- to 5-day-old corn (maize) plant inside, which was pre-infested with 10- to 15-day-old larvae on a piece of insect food.

[0362] Test compounds were formulated and sprayed at 250, 50, 10, and 2 ppm in triplicate as described above. After spraying of the formulated test compounds, the test units were maintained in a growth box at 25° C. and 70% relative humidity for 6 days. Feeding damage was then visually assessed based on ingested stems and larvae were assessed for mortality.

[0363] Of the compounds of Formula 1 tested at 250 ppm, the following provided very good to excellent levels of control efficacy (20% or less feeding damage): 2, 3, 4, 5, 6, 9, 13, 14, 15, 16, 17, 18, 19, 20, 27, 33, 48, 50, 51, 56, 67, and 72.

[0364] Of the compounds of Formula 1 tested at 50 ppm, the following provided very good to excellent levels of control efficacy (20% or less feeding damage): 2, 4, 5, 9, 10, 11, 13, 14, 15, 17, 18, 19, 27, 33, 37, 38, 39, 48, 50, 56, 61, 62, 63, 67, and 72.

[0365] Of the compounds of Formula 1 tested at 10 ppm, the following provided very good to excellent levels of control efficacy (20% or less feeding damage): 2, 4, 9, 10, 11, 13, 15, 18, 19, 27, 50, 67, and 72.

[0366] Of the compounds of Formula 1 tested at 2 ppm, the following provided very good to excellent levels of control efficacy (20% or less feeding damage): 2, 13, and 19.

[0367] Test C To evaluate control of the corn planthopper (Peregrinus maidis (Ashmead)) by contact and / or systemic means, the test unit consisted of a small open container with a 3-4 day old corn (maize) plant inside. White sand was added on top of the soil prior to application of the test compound.

[0368] Test compounds were formulated and sprayed at 250 and 50 ppm in triplicate as described above. After spraying of the formulated test compounds, the test units were allowed to dry for 1 hour, after which they were post-infested with approximately 15-20 nymphs (18-21 days old). A black obscuring cap was placed on top of each test unit, and the test units were kept in a growth box at 22-24°C and 50-70% relative humidity for 6 days. Each test unit was then visually assessed for insect mortality.

[0369] Of the compounds of Formula 1 tested at 250 ppm, the following produced at least 80% mortality: 3, 4, 9, 10, 11, 13, 27, 50, and 72.

[0370] Of the compounds of Formula 1 tested at 50 ppm, the following produced at least 80% mortality: 9, 10, 11, 13, and 72.

[0371] Test D To evaluate control of the green peach aphid (Myzus persicae (Sulzer)) by contact and / or systemic means, the test units consisted of small open containers with 12-15 day old radish plants inside. Prior to compound application, each test unit was pre-infested by placing 30-40 aphids on leaf pieces excised from cultured plants onto the leaves of the test plants (cut leaf method). As the leaf pieces dried the aphids migrated onto the test plants. After pre-infestation the soil in the test units was covered with a layer of sand.

[0372] Test compounds were formulated and sprayed at 250 and 50 ppm in triplicate as described above. After spraying with the formulated test compounds, each test unit was allowed to dry for 1 hour and then a black obscuring cap was placed on top. The test units were kept in a growth box at 19-21°C and 50-70% relative humidity for 6 days. Each test unit was then visually assessed for insect mortality.

[0373] Of the compounds of Formula 1 tested at 250 ppm, the following produced at least 80% mortality: 4, 9, 11, 13, 50, and 72.

[0374] Of the compounds of formula 1 tested at 50 ppm, the following produced at least 80% mortality: 4.

[0375] Test E To evaluate control of cotton aphid (Aphis gossypii (Glover)) by contact and / or systemic means, the test units consisted of small open containers with 5-day-old okra plants inside, which were pre-infested with 30-40 insects on a single leaf according to the cut-leaf method, and the soil in the test units was covered with a layer of sand.

[0376] Test compounds were formulated and sprayed at 250, 50, 10, and 2 ppm in triplicate as described above. After spraying, the test units were maintained in a growth box at 19° C. and 70% relative humidity for 6 days. Each test unit was then visually assessed for insect mortality.

[0377] Of the compounds of Formula 1 tested at 250 ppm, the following caused at least 80% mortality: 2, 3, 4, 6, 7, 9, 10, 11, 12, 13, 14, 15, 20, 23, 27, 28, 29, 30, 32, 33, 38, 39, 46, 47, 48, 50, 51, 52, 68, 69, and 72.

[0378] Of the compounds of Formula 1 tested at 50 ppm, the following caused at least 80% mortality: 2, 3, 4, 7, 9, 10, 11, 13, 14, 15, 20, 27, 29, 30, 33, 46, 48, 50, 51, 69, and 72.

[0379] Of the compounds of formula 1 tested at 10 ppm, the following produced at least 80% mortality: 2, 4, 10, 11, 13, and 72.

[0380] Of the compounds of formula 1 tested at 2 ppm, the following produced at least 80% mortality: 2, 4, 10, 11, 13, and 72.

[0381] Test F To evaluate control of western flower thrips (Frankliniella occidentalis Pergande) by contact and / or systemic means, each test unit consisted of a small open container with a 5- to 7-day-old Soleil bean plant inside.

[0382] Test compounds were formulated and sprayed at 250 and 50 ppm in triplicate as described above. After spraying, the test units were allowed to dry for 1 hour, then 22-27 adult thrips were added to each unit, which was then covered with a screened lid. The test units were held at 25°C and 45-55% relative humidity for 7 days. Each test unit was then visually assessed for plant damage and insect mortality.

[0383] Of the compounds of Formula 1 tested at 250 ppm, the following provided very good to excellent levels of control efficacy (20% or less feeding damage): 2, 3, 4, 9, 11, 13, 14, 20, 23, 27, 29, 33, 46, 50, 51, 59, and 72.

[0384] Of the compounds of Formula 1 tested at 50 ppm, the following provided very good to excellent levels of control efficacy (20% or less feeding damage): 2, 4, 9, 11, 13, 27, 33, and 50.

[0385] Test G To evaluate control of the Neotropical brown stink bug (Euschistus heros Pergande) by contact and / or systemic means, each test unit consisted of a Petri dish with a 1 cm piece of fresh green bean.

[0386] Test compounds were formulated and sprayed at 250 and 50 ppm in triplicate as described above. Prior to application, each unit was infested with 10 immature insects, and after spraying, the test units were allowed to dry for 1 hour and held at 25° C. and 45-55% relative humidity for 5 days. Each test unit was then visually assessed for insect mortality.

[0387] Of the compounds of Formula 1 tested at 250 ppm, the following provided very good to excellent levels of control efficacy (20% or less feeding damage): 2, 3, 4 and 13.

[0388] Of the compounds of Formula 1 tested at 50 ppm, the following provided very good to excellent levels of control efficacy (20% or less feeding damage): 2, 4 and 13.

Claims

1. Compounds selected from Formula 1, their N-oxides, and salts for controlling invertebrate pests: 【Chemistry 1】 (In the formula, R １ is C １ to C ６ alkyl, C ２ to C ６ alkenyl, C ２ to C ６ alkynyl, or C ３ to C ６ cycloalkyl, where each alkyl, alkenyl, alkynyl or cycloalkyl is substituted with one or more R ６ ; or R １ However, 1 to 3 R ６ A 5-membered aromatic heterocycle containing a ring member selected from a phenyl atom optionally substituted with a carbon atom and one oxygen atom, one sulfur atom, and one to three heteroatoms independently selected from three or fewer nitrogen atoms, or a 6-membered aromatic heterocycle containing a ring member selected from a carbon atom and one to two nitrogen atoms, where each 5-membered to 6-membered aromatic heterocycle contains one or more R ６ It is optionally replaced by; However, R １ However, C １ ~C ６ If it is alkyl, R ６ C １ ~C ６ It is not alkyl; R ２ However, these are hydrogen, halogen, cyano, nitro; or R ２ However, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, or C ３ ~C ７ It is a cycloalkyl group, where each alkyl, alkenyl, alkynyl, or cycloalkyl group comprises one or more R groups. ６ It is optionally replaced by; or R ２ However, the ring member is a 5-membered aromatic heterocycle containing phenyl or a carbon atom and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom, and 3 or fewer nitrogen atoms, or a 6-membered aromatic heterocycle containing a carbon atom and 1 to 2 nitrogen atoms, where each phenyl or aromatic heterocycle contains one or more R ６ and optional Replaced by; or R ２ However, C(O)R ７ , C(O)OR ７ , C(O)NR ７ R ８ , NR ７ R ８ , OR ７ NHC(O)NR ７ R ８ OC(O)R ７ , OC(O)OR ７ , S(O) ｐ R ７ SO ２ NR ７ R ８ , or OS(O) ２ R ９ And; R ３ However, hydrogen, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, or C ３ ~C ６ It is a cycloalkyl group, where each alkyl, alkenyl, alkynyl, or cycloalkyl group comprises one or more R groups. ６ It is optionally replaced by; or R ３ However, C(O)R ７ , C(O)OR ７ , NR ７ R ８ , OR ７ S(O)pR ７ or SO ２ NR ７ R ８ And; R ４ However, H, C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, or C ３ ~C ６ It is a cycloalkyl group, where each alkyl, alkenyl, alkynyl, or cycloalkyl group comprises one or more R groups. ６ It is optionally replaced by; R ５ However, hydrogen or C １ ~C ４ Alkyl; or R ４ and R ５ However, together they can form a 3- to 6-membered carbon-cyclic ring; R ６ However, these are halogens, cyanos, nitros; or R ６ is C １ to C ６ alkyl, C ２ to C ６ alkenyl, C ２ to C ６ alkynyl, or C ３ to C ７ cycloalkyl, where each alkyl, alkenyl, alkynyl or cycloalkyl is optionally substituted with one or more X １ ; or R ６ However, each phenyl, 5-membered-to-6-membered aromatic heterocycle or 3-membered-to-6-membered non-aromatic heterocycle contains a ring member selected from phenyl, or a carbon atom and one to three heteroatoms independently selected from one oxygen atom, one sulfur atom, and three or fewer nitrogen atoms, or a ring member selected from a carbon atom and one to two nitrogen atoms, or a ring member selected from a carbon atom and one to five heteroatoms independently selected from two or fewer oxygen atoms, two or fewer sulfur atoms, and two or fewer nitrogen atoms, wherein each phenyl, 5-membered-to-6-membered aromatic heterocycle or 3-membered-to-6-membered non-aromatic heterocycle contains one or more X １ It is optionally replaced by; or R ６ However, C(O)R ７ , C(O)OR ７ , C(O)NR ７ R ８ , NR ７ R ８ , OR ７ NHC(O)NR ７ R ８ OC(O)R ７ , OC(O)OR ７ S(O)pR ７ SO ２ NR ７ R ８ , or OS(O) ２ R ９ And; R ７ However, hydrogen, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, or C ３ ~C ７ It is a cycloalkyl group, where each alkyl, alkenyl, alkynyl, or cycloalkyl group comprises one or more R groups. ６ It is optionally replaced by; or R ７ However, the ring member is a 5-membered aromatic heterocycle containing phenyl or a carbon atom and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom, and 3 or fewer nitrogen atoms, or a 6-membered aromatic heterocycle containing a carbon atom and 1 to 2 nitrogen atoms, where each phenyl or 5- to 6-membered aromatic heterocycle contains one or more R ６ It is optionally replaced by; R ８ However, hydrogen, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, or C ２ ~C ６ It is an alkynyl, where each alkyl, alkenyl, or alkynyl is one or more R ６ It is optionally replaced by; R ９ However, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, or C ３ ~C ７ It is a cycloalkyl group, where each alkyl, alkenyl, alkynyl, or cycloalkyl group comprises one or more R groups. ６ It is optionally replaced by; or R ９ However, the ring member is a 5-membered aromatic heterocycle containing phenyl or a carbon atom and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom, and 1 to 3 nitrogen atoms, or a 6-membered aromatic heterocycle containing a carbon atom and 1 to 2 nitrogen atoms, where each phenyl or 5- to 6-membered aromatic heterocycle contains one or more R ６ It is optionally replaced by; n is between 0 and 4; p is between 0 and 2, Q is, 【Chemistry 2】 And, A １ and A ２ However, the ring member is a five-membered aromatic heterocycle containing a carbon atom and one oxygen atom, one sulfur atom, and one to three heteroatoms independently selected from one to three nitrogen atoms, or a six-membered aromatic heterocycle containing a carbon atom and one to two nitrogen atoms, where each five- to six-membered aromatic heterocycle contains one or more R ６ It is optionally replaced by; R １０ , R １１ and R １２ However, these are hydrogen, halogen, cyano, nitro; or R １０ , R １１ and R １２ However, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, or C ３ ~C ７ It is a cycloalkyl group, where each alkyl, alkenyl, alkynyl, or cycloalkyl group comprises one or more R groups. ６ It is optionally replaced by; or R １０ , R １１ and R １２ However, 1 to 3 R ６ A 5-membered aromatic heterocycle containing a ring member selected from a phenyl atom optionally substituted with a carbon atom and one oxygen atom, one sulfur atom, and one to three heteroatoms independently selected from one to three nitrogen atoms, or a 6-membered aromatic heterocycle containing a ring member selected from a carbon atom and one to two nitrogen atoms, where each 5-membered to 6-membered aromatic heterocycle contains one or more R ６ It is optionally replaced by; or R １０ , R １１ and R １２ However, C(O)R ７ , C(O)OR ７ , C(O)NR ７ R ８ , NR ７ R ８ , OR ７ NHC(O)NR ７ R ８ OC(O)R ７ , OC(O)OR ７ , S(O) ｐ R ７ SO ２ NR ７ R ８ , or OS(O) ２ R ９ And; X １ However, hydrogen, halogen, cyano, nitro, OH, CHO, CO ２ H, CO(C １ ~C ４ Alkyl), CO ２ (C １ ~C ４ Alkyl), C(O)NH(C １ ~C ４ Alkyl), C(O)N(C １ ~C ４ Alkyl) ２ NH(C １ ~C ４ Alkyl), N (C １ ~C ４ Alkyl) ２ , O(C １ ~C ４ Alkyl), O (C １ ~C ４ Haloalkyl), NHC(O)NH(C) １ ~C ４ Alkyl), NHC(O)N(C １ ~C ４ Alkyl) ２ , OC(O)(C １ ~C ４ Alkyl), OCO ２ (C １ ~C ４ Alkyl), S(O) ｐ (C １ ~C ４ Alkyl), S(O) ｐ (C １ ~C ４ Haloalkyl), SO ２ NH(C) １ ~C ４ Alkyl), SO ２ N(C) １ ~C ４ Alkyl) ２ OS(O) ２ (C １ ~C ４ Alkyl), OS(O) ２ (C １ ~C ４ (haloalkyl); or X １ However, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C ７ Cycloalkyl or C ４ ~C ８ It is a cycloalkylalkyl; where each alkyl, alkenyl, alkynyl, or cycloalkyl is one or more halogens, cyano, nitro, OH, CHO, CO ２ H, CO(C １ ~C ４ Alkyl), CO ２ (C １ ~C ４ Alkyl), C(O)NH(C １ ~C ４ Alkyl), C(O)N(C １ ~C ４ Alkyl) ２ NH(C １ ~C ４ Alkyl), N (C １ ~C ４ Alkyl) ２ , O(C １ ~C ４ Alkyl), O (C １ ~C ４ Haloalkyl), NHC(O)NH(C) １ ~C ４ Alkyl), NHC(O)N(C １ ~C ４ Alkyl) ２ , OC(O)(C １ ~C ４ Alkyl), OCO ２ (C １ ~C ４ Alkyl), S(O) ｐ (C １ ~C ４ Alkyl), S(O) ｐ (C １ ~C ４ Haloalkyl), SO ２ NH(C) １ ~C ４ Alkyl), SO ２ N(C) １ ~C ４ Alkyl) ２ , or OS(O) ２ (C １ ~C ４ Alkyl), OS(O) ２ (C １ ~C ４ Optionally substituted with a haloalkyl; or X １ However, a five-membered aromatic compound containing a ring member selected from phenyl, or a carbon atom and one to three heteroatoms independently selected from one oxygen atom, one sulfur atom, and one to three nitrogen atoms. A six-membered aromatic heterocycle containing an elementary ring or a ring member selected from a carbon atom and one or two nitrogen atoms, where each phenyl or five- to six-membered aromatic heterocycle contains one or more halogens, cyano, nitro, OH, CHO, CO ２ H, CO(C １ ~C ４ Alkyl), CO ２ (C １ ~C ４ Alkyl), C(O)NH(C １ ~C ４ Alkyl), C(O)N(C １ ~C ４ Alkyl) ２ NH(C １ ~C ４ Alkyl), N (C １ ~C ４ Alkyl) ２ , O(C １ ~C ４ Alkyl), O (C １ ~C ４ Haloalkyl), NHC(O)NH(C) １ ~C ４ Alkyl), NHC(O)N(C １ ~C ４ Alkyl) ２ , OC(O)(C １ ~C ４ Alkyl), OCO ２ (C １ ~C ４ Alkyl), S(O) ｐ (C １ ~C ４ Alkyl), S(O) ｐ (C １ ~C ４ Haloalkyl), SO ２ NH(C) １ ~C ４ Alkyl), SO ２ N(C) １ ~C ４ Alkyl) ２ , or OS(O) ２ (C １ ~C ４ Alkyl), OS(O) ２ (C １ ~C ４ (Optionally substituted with a haloalkyl group).

2. R １ However, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, or C ２ ~C ６ It is an alkynyl, where each alkyl, alkenyl, or alkynyl is one or more R ６ Replaced by; or R １ However, 1 to 3 R ６ A phenyl that is optionally substituted with R; or R １ However, one or more R ６ The compound according to claim 1, which is a pyrimidine that is optionally substituted.

3. R ２ However, these are hydrogen, halogen, cyano, nitro; or R ２ However, C １ ~C ６ It is alkyl, and here each C １ ~C ６ Alkyl is one or more R ６ It is optionally replaced by; or R ２ However, C(O)R ７ , C(O)OR ７ , C(O)NR ７ R ８ , NR ７ R ８ , OR ７ , S(O) ｐ R ７ SO ２ NR ７ R ８ , or OS(O) ２ R ９ The compound according to claim 1.

4. R ３ However, hydrogen, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, or C ３ ~C ６ It is a cycloalkyl group, where each alkyl, alkenyl, alkynyl, or cycloalkyl group comprises one or more R groups. ６ The compound according to claim 1, which is optionally substituted with

5. R ４ However, one or more R ６ C is optionally replaced by １ ~C ６ The compound according to claim 1, wherein it is alkyl.

6. R ５ The compound according to claim 1, wherein is H.

7. R ６ However, C １ ~C ６ Alkyl or C ３ ~C ７ It is a cycloalkyl group, where each alkyl or cycloalkyl group is a halogen, cyano, nitro, or C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, C １ ~C ４ Haloalkoxy, C １ ~C ４ Alkylamino, C １ ~C ４ Dialkylamino, C １ ~C ４ Alkylthio, C １ ~C ４ Haloalkylthio, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfonyl or C １ ~C ４ The compound according to claim 1, which is optionally substituted with one or more substituents selected from haloalkylsulfonyls.

8. A １ and A ２ However, halogen, cyano, nitro, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, C １ ~C ４ Haloalkoxy, C １ ~C ４ Alkylamino, C １ ~C ４ Dialkylamino, C １ ~C ４ Alkylthio, C １ ~C ４ Haloalkylthio, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfonyl, C １ ~C ４ Haloalkylsulfonyl, C(O)R ７ , C(O)OR ７ , C(O)NR ７ R ８ , NR ７ R ８ , OR ７ NHC(O)NR ７ R ８ OC(O)R ７ , OC(O ) OR ７ S(O)pR ７ SO ２ NR ７ R ８ , or OS(O) ２ R ９ Pyridine, pyrimidine, pyrazine, or pyridazine are optionally substituted; R １０ , R １１ and R １２ However, hydrogen, halogen, cyano, nitro, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, C １ ~C ４ Haloalkoxy, C １ ~C ４ Alkylamino, C １ ~C ４ Dialkylamino, C １ ~C ４ Alkylthio, C １ ~C ４ Haloalkylthio, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfonyl or C １ ~C ４ The compound according to claim 1, which is a haloalkylsulfonyl.

9. Q is Q １ The compound according to claim 1.

10. Q is Q ２ The compound according to claim 1.

11. The compound of formula 1 is, formula 1': 【Transformation 3】 The compound according to claim 1, which is a compound of formula 1'.

12. The compound of formula 1 is, formula 1'': 【Chemistry 4】 The compound according to claim 1, which is a compound of formula 1''.

13. R １ However, C １ ~C ６ It is an alkyl group, where each alkyl group has one or more R ６ Replaced by; or R １ However, 1 to 3 R ６ A phenyl that is optionally substituted with; or R １ However, one or more R ６ It is a pyrimidine that is optionally substituted; R ２ However, these are hydrogen, halogen, cyano, nitro; or R ２ However, C １ ~C ６ It is alkyl, and here each C １ ~C ６ Alkyl is one or more R ６ It is optionally replaced by; or R ２ However, C(O)R ７ , C(O)OR ７ , C(O)NR ７ R ８ , NR ７ R ８ , OR ７ , S(O) ｐ R ７ SO ２ NR ７ R ８ , or OS(O) ２ R ９ And; R ３ However, hydrogen, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, or C ３ ~C ６ It is a cycloalkyl group, where each alkyl, alkenyl, alkynyl, or cycloalkyl group comprises one or more R groups. ６ It is optionally replaced by; R ４ However, one or more R ６ C is optionally replaced by １ ~C ６ It is alkyl; R ５ is hydrogen; R ６ However, halogen, cyano, nitro, CN, C(O)R ７ , C(O)OR ７ , C(O)NR ７ R ８ , NR ７ R ８ , OR ７ NHC(O)NR ７ R ８ OC(O)R ７ , OC(O)OR ７ , S(O) ｐ R ７ SO ２ NR ７ R ８ OS(O) ２ R ９ is, or R ６ However, C １ ~C ６ Alkyl or C ３ ~C ７ It is a cycloalkyl group, where each alkyl or cycloalkyl group is a halogen, cyano, nitro, or C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, C １ ~C ４ Haloalkoxy, C １ ~C ４ Alkylamino, C １ ~C ４ Dialkylamino, C １ ~C ４ Alkylthio, C １ ~C ４ Haloalkylthio, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfonyl or C １ ~C ４ Optionally substituted with one or more substituents selected from haloalkylsulfonyls; R ７ , R ８ and R ９ However, hydrogen, C １ ~C ４ Alkyl or C １ ~C ４ It is a haloalkyl; Q is 【Transformation 5】 And, A １ and A ２ However, halogen, cyano, nitro, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C4 alkoxy, C １ ~C ４ Haloalkoxy, C １ ~C ４ Alkylamino, C １ ~C ４ Dialkylamino, C １ ~C ４ Alkylthio, C １ ~C ４ Haloalkylthio, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfonyl or C １ ~C ４ Pyridine, pyrimidine, pyrazine, pyridazine, or thiazole, optionally substituted with a haloalkylsulfonyl; R １０ , R １１ and R １２ However, hydrogen, halogen, cyano, nitro, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, C １ ~C ４ Haloalkoxy, C １ ~C ４ Alkylamino, C １ ~C ４ Dialkylamino, C １ ~C ４ Alkylthio, C １ ~C ４ Haloalkylthio, C １ ~C ４ Alkyl sulfinyl, C1-C4 haloalkyl sulfinyl, C1-C4 alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfonyl or C １ ~C ４ The compound according to claim 1, which is a haloalkylsulfonyl.

14. R １ However, C １ ~C ６ It is an alkyl group, where each alkyl group has one or more R ６ Replaced by; or R １ However, 1 to 3 R ６ It is a phenyl that is optionally substituted; R ２ However, these are hydrogen, halogen, cyano, nitro; or R ２ However, C １ ~C ６ It is alkyl, and here each C １ ~C ６ Alkyl is one or more R ６ It is optionally replaced by; or R ２ However, C(O)R ７ , C(O)OR ７ , C(O)NR ７ R ８ , NR ７ R ８ , OR ７ , S(O) ｐ R ７ SO ２ NR ７ R ８ , or OS(O) ２ R ９ And; R ３ However, hydrogen, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, or C ３ ~C ６ It is a cycloalkyl group, where each alkyl, alkenyl, alkynyl, or cycloalkyl group comprises one or more R groups. ６ It is optionally replaced by; R ４ However, one or more R ６ C is optionally replaced by １ ~C ６ It is alkyl; R ５ is hydrogen; R ６ However, halogen, cyano, nitro, CN, C(O)R ７ , C(O)OR ７ , C(O)NR ７ R ８ , NR ７ R ８ , OR ７ NHC(O)NR ７ R ８ OC(O)R ７ , OC(O)OR ７ , S(O) ｐ R ７ SO ２ NR ７ R ８ OS(O) ２ R ９ is, or R ６ However, C １ ~C ６ Alkyl or C ３ ~C ７ It is a cycloalkyl group, where each alkyl or cycloalkyl group is a halogen, cyano, nitro, or C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, C １ ~C ４ Haloalkoxy, C １ ~C ４ Alkylamino, C １ ~C ４ Dialkylamino, C １ ~C ４ Alkylthio, C １ ~C ４ Haloalkylthio, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfonyl or C １ ~C ４ Optionally substituted with one or more substituents selected from haloalkylsulfonyls; R ７ , R ８ and R ９ However, hydrogen, C １ ~C ４ Alkyl or C １ ~C ４ It is a haloalkyl; Q is 【Transformation 6】 And, A １ and A ２ However, halogen, cyano, nitro, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C4 alkoxy, C １ ~C ４ Haloalkoxy, C １ ~C ４ Alkylamino, C １ ~C ４ Dialkylamino, C １ ~C ４ Alkylthio, C １ ~C ４ Haloalkylthio, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfonyl or C １ ~C ４ Pyridine, pyrimidine, pyrazine, pyridazine, or thiazole, optionally substituted with a haloalkylsulfonyl; R １０ , R １１ and R １２ However, hydrogen, halogen, cyano, nitro, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, C １ ~C ４ Haloalkoxy, C １ ~C ４ Alkylamino, C １ ~C ４ Dialkylamino, C １ ~C ４ Alkylthio, C １ ~C ４ Haloalkylthio, C １ ~C ４ Alkyl sulfinyl, C1-C4 haloalkyl sulfinyl, C1-C4 alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfonyl or C １ ~C ４ The compound according to claim 1, which is a haloalkylsulfonyl.

15. R １ However, C １ ~C ４ It is an alkyl group, where each alkyl group is one or more halogens, cyano, nitro, or C ３ ~C ６ Cycloalkylalkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, C １ ~C ４ Haloalkoxy, C １ ~C ４ Alkylamino, C １ ~C ４ Dialkylamino, C １ ~C ４ Alkylthio, C １ ~C ４ Haloalkylthio, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfonyl, C １ ~C ４ Haloalkylsulfonyl, C １ ~C ４ Alkyl sulfonate or C １ ~C ４ Substituted with a haloalkylsulfonate; or R １ However, 1 to 3 halogens, cyano, nitro, C ３ ~C ６ Cycloalkylalkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, C １ ~C ４ Haloalkoxy, C １ ~C ４ Alkylamino, C １ ~C ４ Dialkylamino, C １ ~C ４ Alkylthio, C １ ~C ４ Haloalkylthio, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl or C １ ~C ４ A phenyl that is optionally substituted with a haloalkylsulfonyl; R ２ is halogen, cyano, nitro, C １ to C ４ alkyl, C １ to C ４ haloalkyl, C １ to C ４ alkoxy, C １ to C ４ haloalkoxy, C １ to C ４ alkylamino, C １ to C ４ dialkylamino, C １ to C ４ alkylthio, C １ to C ４ haloalkylthio, C1 - C4 alkylsulfinyl, C1 - C4 haloalkylsulfinyl, C1 - C4 alkylsulfinyl, C1 - C4 haloalkylsulfinyl, C １ to C ４ alkylsulfonyl or C １ to C ４ haloalkylsulfonyl; R ３ However, hydrogen, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C ６ Cycloalkyl, or C ４ ~C ７ It is an alkylcycloalkyl, where each alkyl, alkenyl, alkynyl, or cycloalkyl is one or more R ６ It is optionally replaced by; R ４ However, H, C １ ~C ６ Alkyl or C ３ ~C ６ It is cycloalkyl; R ５ is hydrogen; Q is, 【Transformation 7】 And, A １ and A ２ However, halogen, cyano, nitro, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, C １ ~C ４ Haloalkoxy, C １ ~C ４ Alkylamino, C １ ~C ４ Dialkylamino, C １ ~C ４ Alkylthio, C １ ~C ４ Haloalkylthio, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ Haloalkylsulfinyl, C １ ~C ４ Alkyl sulfonyl or C １ ~C ４ Pyridine, pyrimidine, pyrazine, pyridazine, or thiazole, optionally substituted with a haloalkylsulfonyl; R １０ 、 R １１ and R １２ are hydrogen, halogen, cyano, nitro, C １ to C ４ alkyl, C １ to C ４ haloalkyl, C １ to C ４ alkoxy, C １ to C ４ haloalkoxy, C １ to C ４ alkylamino, C １ to C ４ dialkylamino, C １ to C ４ alkylthio, C １ to C ４ haloalkylthio, C １ to C ４ alkylsulfinyl, C １ to C ４ haloalkylsulfinyl, C １ to C ４ alkylsulfonyl or C １ to C ４ haloalkylsulfonyl, and the compound according to claim 1. １ to C ４ is １ to C ４ haloalkylsulfonyl.

16. R １ However, CF ３ , or 1 to 3 halogens, cyanophosphates, CF ３ , OCH ３ or OCF ３ It is a phenyl that is optionally substituted; R ２ However, halogen, cyano, nitro, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy or C １ ~C ４ It is a haloalkoxy; R ３ However, hydrogen, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C ６ Cycloalkyl, or C ４ ~C ７ It is alkylcycloalkyl; R ４ However, C １ ~C ３ It is alkyl; R ５ is hydrogen; Q is, 【Transformation 8】 And, A １ and A ２ However, halogen, cyano, nitro, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy or C １ ~C ４ A pyridine or pyrimidine that is optionally substituted with a haloalkoxy; R １０ , R １１ and R １２ The compound according to claim 1, wherein the compound is hydrogen.

17. The aforementioned compound, 3-[(phenylsulfonyl)oxy]-N-[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]-5-(trifluoromethyl)benzamide; 3-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]-5-(trifluoromethyl)phenyl 1,1,1-trifluoromethanesulfonate; 3-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]phenyl 1,1,1-trifluoromethanesulfonate; 3-Chloro-5-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]phenyl 1,1,1-trifluoromethanesulfonate; 3-Chloro-5-[(phenylsulfonyl)oxy]-N-[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]benzamide; 3-[(phenylsulfonyl)oxy]-N-[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]benzamide; 3-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]phenyl 1,1-difluoromethanesulfonate; (S) 3-chloro-5-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]phenyl 1,1,1-trifluoromethanesulfonate; (-) enantiomer; (R) 3-chloro-5-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]phenyl 1,1,1-trifluoromethanesulfonate; (+) enantiomer; 3-Chloro-5-[[(Cyclopropylmethyl)[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]phenyl 1,1,1-trifluoromethanesulfonate; 3-[[(cyclopropylmethyl)[1-[1-(2-pyrimidinyl)-1H-1,2, 4-Triazole-5-ylethyl]amino]carbonyl]-5-(trifluoromethyl)phenyl 1,1,1-trifluoromethanesulfonate; (S) 3-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]-5-(trifluoromethyl)phenyl 1,1,1-trifluoromethanesulfonate; (-) enantiomer; (R) 3-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]-5-(trifluoromethyl)phenyl 1,1,1-trifluoromethanesulfonate; (+) enantiomer; 3-Fluoro-5-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]phenyl 1,1,1-trifluoromethanesulfonate; 3-bromo-5-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]phenyl 1,1,1-trifluoromethanesulfonate; 1,1'-[5-[[[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]-1,3-phenylene]bis(1,1,1-trifluoromethanesulfonate); 3-[[[1-[1-(5-cyano-2-pyridinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]phenyl 1,1-difluoromethanesulfonate; 3-Chloro-5-[[[1-[1-(5-cyano-2-pyridinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]phenyl 1,1-difluoromethanesulfonate; 3-[[[1-[1-(5-cyano-2-pyridinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]-5-(trifluoromethyl)phenyl 1,1,1-trifluoromethanesulfonate; 3-[[ethyl[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]-5-(trifluoromethyl)phenyl 1,1,1-trifluoromethanesulfonate; 3-Chloro-5-[[ethyl[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]phenyl 1,1,1-trifluoromethanesulfonate; 3-[[[(1S)-1-[1-[6-(aminocarbonyl)-4-pyrimidinyl]-1H-1,2,4-triazole-5-yl]ethyl]amino]carbonyl]-5-(trifluoromethyl)phenyl 1,1,1-trifluoromethanesulfonate; and 3-Chloro-5-[[Methyl[1-[1-(2-pyrimidinyl)-1H-1,2,4-triazole-5-yl]ethyl]amino]carbamoyl]phenyl 1,1,1-trifluoromethanesulfonate A compound according to claim 1, selected from the group consisting of the following.

18. A composition comprising the compound described in claim 1 and at least one further component selected from surfactants, solid diluents, and liquid diluents, wherein the composition optionally further comprises at least one further bioactive compound or agent.

19. The aforementioned at least one further bioactive compound or drug is abamectin, acephate, acekinosyl, acetamiprid, acrinatrin, afidopiropene, amidoflumet, amitraz, avermectin, azadirachtin, azinphos-methyl, benfuracarb, bensultap, bifenthrin, bifenazate, bistriflurone, borate, buprofezin, carbaryl, carbofuran, cartap, carzol, chlorantraniliprole, chlorfenapyr, chlorfluazurone, chlorpyrifos, chlorpyrifos - Methyl, chromafenozide, clofentidine, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin, cycloxapride, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, diafenthiurone, diazinon, dierudrin, diflubenzuron, dimefluthrin, dimehypo, dimethoate, dinotefuran, diofenolan, emamectin, en Dosulfan, Esfenvalerate, Ethiprole, Etofenprox, Ethoxazole, Fenbutasin Oxide, Fenitrothion, Phenothiocarb, Phenoxycarb, Fenpropathrin, Fenvalerate, Fipronil, Flomethoquin, Flonicamide, Flubendiamide, Flucitrinate, Fluphenerim, Flufenoxuron, Fluphenoxystrobin, Fluensulfone, Fluopyram, Flupyradiflon, Fluvalinate, Tau-Fluvalinate, Honofos, Formetanate, Fostiazate, Halophenozide, Heptaflutrin Hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, indoxacarb, insecticide soap, isofenphos, lufenuron, malathion, meperfluthrin, metaflumizone, metaldehyde, methamidophos, methidathion, methiocarb, methomyl, methoprene, methoxychlor, methoxyphenozide, metofluthrin, monoclotophos, monofluorothrin, nicotine, nitenpyram, nithiazine, novaron, nobiflumuron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalon, phosmet Phosphamidone, Pyrimicalb, Profenofos, Profluthrin, Propargit, Protrefenbuto, Piflubmid, Pymetrozine, Pyrafluprole, Pyrethrin, Pyridaben, Pyridaryl, Pyrifluquinazon, Pyriminostrobin, Pyriprole, Pyriproxyfen, Rotenone, Ryanodine, Silafluofen, Spinetoram, Spinosad, Spirodiclofen, Spiromesifen, Spirotetramato, Sulprofos, Sulfoxaflor, Tebufenozide, Tebufenpyrad, Teflubenzuron, Tefluthrin, Tetrachlorvinfos,The composition according to claim 18, selected from tetramethrin, tetramethylfluthrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, thioxazafen, tolfenpyrad, tralomethrin, triazamate, trichlorfon, triflumesopyrim, triflumulon, Bacillus thuringiensis delta-endotoxin, entomopathogenic bacteria, entomopathogenic viruses, and entomopathogenic fungi.

20. A method for controlling invertebrate pests, comprising contacting the invertebrate pest or its environment with a biologically effective amount of the compound described in claim 1.

21. Treated seeds containing the compound described in claim 1 in an amount of approximately 0.0001 to 1% by weight of the seeds before treatment.

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