TW202506675A - Linked bicyclic compounds for controlling and combating invertebrate pests - Google Patents

Abstract

Disclosed are compounds of Formula 1, including all geometric and stereoisomers, N‑oxides, and salts thereof, wherein L, R1, m, R2, R3, and R4, are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1and methods for controlling and combating an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound or a composition of the disclosure.

Description

Linked bicyclic compounds for controlling and combating invertebrate pests

Cross-references to related applications

This application claims the benefit of priority to U.S. Provisional Application No. 63/531,348, filed on August 8, 2023, which is incorporated herein by reference.

The present disclosure relates to certain azole compounds, their N -oxides, salts and compositions suitable for agricultural and non-agricultural uses, and methods of their use for controlling and combating invertebrate pests such as arthropods in agricultural and non-agricultural settings.

Controlling and combating invertebrate pests is extremely important in achieving high crop efficiency. Damage to growing and stored crops by invertebrate pests can result in significant reductions in productivity and, therefore, increased costs to the consumer. Controlling and combating invertebrate pests in forestry, greenhouse crops, ornamental plants, nursery crops, stored food and fiber products, livestock, household, turf, wood products, and public and animal health is also important. Many products are commercially available for these purposes, but there is a continuing need for new compounds that are more effective, less costly, less toxic, safer for the environment, or have different sites of action.

WO 2022/003510 A1 discloses certain triazolopyridine compounds that can be used as pesticidal agents.

The present disclosure relates to compounds having formula 1 (including all geometric isomers and stereoisomers), N -oxides and salts thereof, and compositions containing them, and their use for controlling and combating invertebrate pests: wherein L is CR ⁵ R ⁶ , CR ⁵ R ⁶ CR ⁵ R ⁶ , OCR ⁵ R ⁶ , CR ⁵ R ⁶ O; CR ⁵ R ⁶ NR ⁷ , NR ⁷ CR ⁵ R ⁶ , C(=E)NR ⁷ , NR ⁷ C(=E), C(=E) CR ⁵ R ⁶ , CR ⁵ R ⁶ C(=E), C(=CR ⁵ R ⁶ ), CR ⁵ =CR ⁶ or C(=E); E is O, S or NR ⁸ ; m is 0, 1, 2, 3, 4 or 5; each R ¹ is independently halogen, cyano, nitro, hydroxyl, SF ₅ , C(O)NH ₂ , C(O)NR ¹⁰ R ¹¹ , C(=NR ¹³ )NR ¹⁰ R ¹¹ , C(=NR ¹³ )R ¹⁴ R , OC(O)R ¹⁴ , NR ¹⁰ R ¹¹ , NR ¹³ C(O)R ¹⁴ , C(O)R ¹⁴ , S(O) _n R ¹⁴ , OS(O) _n R ¹⁴ , Si(R ¹⁴ ) ₃ , OSi(R ¹⁴ ) ₃ or MQ ^a ; or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ cycloalkoxy, which is unsubstituted or substituted by at least one R ^x ; or two R on adjacent ring atoms ¹ substituents together with the carbon atoms to which they are attached form a 4 to 7 membered ring containing carbon atoms and up to 3 heteroatom ring members independently selected from up to 2 oxygen atoms, one sulfur atom and up to 3 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O) or S(O) ₂ , said ring being unsubstituted or substituted with at least one R ^x ; each R ² , R ³ , R ⁴ is independently hydrogen, halogen, cyano, nitro, hydroxyl, SF ₅ , C(O)H, C(O)NH 2 , C(O)NR 10 R ₁₁ , C(=NR 13 )NR ¹⁰ R ¹¹ , C(=NR ¹³ )NR ¹⁰ R ¹¹ , C(=NR or C ^{1 -C 6 alkyl} , C 3 ^-C 6 cycloalkyl, ^C 1 -C ⁶ alkoxy, ^C 3 _-C ^{6 cycloalkoxy} , C ² -C ₆ alkenyl _or C ₂ -C ₆ alkynyl, which is unsubstituted or substituted by at least _one R ^x ; or _two substituents _{on adjacent} ring atoms ⁽ R ² _{and R 3} ^, or R ³ _and R _{4 )} are substituted or replaced _by at ^least one R ^{x ;} ) together with the carbon atoms to which they are attached form a 4 to 7 membered ring containing ring members selected from carbon atoms and up to 3 heteroatoms independently selected from up to 2 oxygen atoms, one sulfur atom and up to 3 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are selected from S, S(O) or S(O) ₂ , said ring being unsubstituted or substituted with at least one R ^x ; M is a direct bond, O, S, S(O), S(O) ₂ or NR ⁹ ; R ⁵ and R ⁶ are independently hydrogen, hydroxyl, halogen, cyano, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ halogenated alkyl, C ₁ -C 6 R ₅ and R ⁶ _each attached to the same carbon atom together with the carbon atom to _which they are attached form a _{3- to 7 -membered ring containing ring members selected from carbon atoms and up to 3 heteroatoms independently} selected from one oxygen atom, ^one sulfur atom and up to 3 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are selected from S, S(O) or S(O) ₂ , said ring being unsubstituted or substituted with at least one R ^x ; or in the case of CR ⁵ R ⁶ CR ⁵ R ⁶ , each R ⁵ and R 6 ^{R 15} is attached to each of the first and second adjacent carbon atoms and can form, together with the carbon atoms to which they are attached, a 3 to 7 membered ring containing ring members selected from carbon atoms and up to 3 heteroatoms, the heteroatoms being independently selected from one oxygen atom, one sulfur atom and up to 3 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are selected from S, S(O) or S(O) ₂ , the ring being unsubstituted or substituted with at least one R ^x ; each R ⁷ is independently H, C(O)R ¹⁵ or S(O) ₂ R ¹⁵ or Q ^b ; or C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl or C ₂ -C each R ⁸ is independently NR ¹⁰ R ¹¹ , OR ¹² , C(═NR ¹³ ₎ R 14 , C(O)NR 10 R 11 , C(O)R ¹⁴ or S(O) _n R ¹⁴ ; or ^phenyl , C ¹ -C 6 alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, each of which is unsubstituted or substituted by at least one R ^x ; each R ⁹ is independently H, NR 10 R ¹¹ , OR 12 , C(═NR _{13 )} R ¹⁴ , C(O)NR ¹⁰ R ¹¹ , C(O ^{)R 14} _or S(O) n R ¹⁴ ; or phenyl, C 1 -C ⁶ alkyl, C ^{3 -C 6} cycloalkyl, C 2 -C ⁶ alkenyl or C ₂ -C ₆ alkynyl, each of which is unsubstituted or substituted _{by at} least one R x R ^x is independently halogen, cyano, nitro, hydroxyl, C ₁ -C ₆ alkyl, C ₂ ^-C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ halogenated alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halogenated cycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ halogenated alkoxy, C ₃ -C ₆ cycloalkoxy, C _{3 -C 6} halogenated cycloalkoxy, C(O)NH ₂ , _C (O)NR ₁₀ R ₁₁ , C( ^{═NR 13} ₎ R ₁₄ ^, OC(O ⁾ R ¹⁴ , NR ¹⁴ R ¹⁰ R ¹¹ , NR ¹⁴ C(O)R ¹⁴ , C(O)R ¹⁴ , S(O) _n R ¹⁴ , OS(O) _n R ¹⁴ , Si(R ¹⁴ ) ₃ , OSi(R ¹⁴ ) ₃ or Q ^b ; each R ¹⁰ is independently C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ halogenated alkyl, C ₂ -C 6 alkenyl or C ₂ -C ₆ alkynyl, C(O)R ¹⁵ or S(O) ₂ R ¹⁵ ; or phenyl or a 5- or 6-membered heterocyclic aromatic ring, each of which is unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C 3 -C 6 cycloalkyl, C 1 -C ₆ halogenated alkyl, C 2 -C 6 alkenyl or C _{2 -C 6} alkynyl, -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; each R ¹¹ is independently H, C ₁ -C ₆ alkyl or C ₁ -C ₄ haloalkyl; or R ¹⁰ and R ¹¹ together with the nitrogen atom to which they are attached form a 3 to 7 membered ring containing ring members selected from carbon atoms and up to 3 heteroatoms independently selected from one oxygen atom, one sulfur atom and up to 3 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring member is selected from S, S(O) or S(O) ₂ , the ring is unsubstituted or substituted by at least one substituent independently selected from the following group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ halogenated alkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ halogenated alkoxy; each R ¹² is independently H, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl or C ₁ -C ₄ halogenated alkyl; or phenyl, which is unsubstituted or substituted by at least one substituent independently selected from the following group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ halogenated alkyl, C ₁ -C each R ¹³ is independently H; OR ¹⁶ , S(O) _n R ¹⁷ , C(O)OR ¹⁷ , C(O)R ¹⁷ or NHR ¹⁸ ; each R ¹⁴ is independently H; or C _{1 -C 6} alkyl _, C ₃ -C ₆ cycloalkyl, _{C 2} -C ₆ alkenyl or C ₂ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ cycloalkoxy, each of which is unsubstituted or substituted by at least one halogen, cyano or nitro; or C(O)OR ¹⁷ , C(O)NR ²² R ²³ , NR ²² R ²³ , NR ²⁴ C(O)R ¹⁷ , C(O)R ¹⁷ or Q ^b ; each R ^{R 15} is independently C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy or NR ²² R ²³ ; or phenyl or a 5- or 6-membered heterocyclic aromatic ring, each of which is unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; each R ¹⁶ is independently C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C (O) R ¹⁹ , S (O) _n ^R20 or Q ^b ; each R ¹⁷ is independently C ₁ -C ₄ alkyl or C ₁ -C ₄ halogenated alkyl; R ¹⁸ is C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ halogenated alkyl, C(O)R ¹⁹ or C(O)OR ²¹ ; or phenyl, which is unsubstituted or substituted with at least one substituent independently selected from the following group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ halogenated alkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ halogenated alkoxy; each R ¹⁹ is independently C ₁ -C ₄ alkyl, C ₁ -C ₄ halogenated alkyl, C ₃ -C C 1 -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C _{6 cycloalkyl, C 3 -C 6} halocycloalkyl, C ₃ -C 6 cycloalkylalkyl or C 3 -C ₆ halocycloalkylalkyl; or phenyl which is unsubstituted or substituted by at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; each R ²⁰ is independently C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₃ -C ₆ cycloalkylalkyl or C ₃ -C 6 halocycloalkylalkyl; or phenyl, which is unsubstituted or substituted by at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C _{6 cycloalkyl} , C 1 -C ₄ halogenated alkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ halogenated alkoxy; each R ²¹ is independently C _{1 -C 4} alkyl, C ₁ -C ₄ halogenated alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halogenated cycloalkyl, C ₃ -C ₆ cycloalkylalkyl or C ₃ -C or phenyl, which is unsubstituted or substituted by at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C _{6 cycloalkyl} , C 1 -C ₄ halogenated alkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ halogenated alkoxy; each R ²² is independently H, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ halogenated alkyl, C _{2 -C 6} alkenyl or C ₂ -C ₆ alkynyl, C(O)R ²⁵ or S(O) ₂ R ²⁵ or phenyl or a 5- or 6-membered heterocyclic aromatic ring, each of which is unsubstituted or substituted by at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ halogenated alkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ halogenated alkoxy; each R ²³ is independently H, C ₁ -C ₆ alkyl or C ₁ -C ₄ halogenated alkyl; or R ²² and R ²³ together with the nitrogen atom to which they are attached form a 3 to 7 membered ring containing ring members selected from carbon atoms and up to 2 heteroatoms independently selected from one oxygen atom, one sulfur atom and up to 2 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are selected from S, S(O) or S(O) ₂ , said ring being unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ halogenated alkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ halogenated alkoxy; each R ^{R 24} is independently H or C ₁ -C ₄ alkyl; each R ²⁵ is independently C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₆ haloalkoxy; or phenyl or a 5- or 6-membered heterocyclic aromatic ring, each of which is unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; each Q ^a is independently phenyl, a 5- or 6-membered heterocyclic aromatic ring or a 3- to 6-membered heterocyclic non-aromatic ring, each ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from one oxygen atom, one sulfur atom and up to 4 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O) or S(O) ₂ , each ring being unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ halogenated alkyl, C 1 -C 4 alkoxy and C ₁ -C ₄ alkyl radicals. _each ^Qb is independently phenyl, a 5- or ₆ -membered heterocyclic aromatic ring or a 3- to 6-membered heterocyclic non-aromatic ring, each ring containing ring members selected from carbon atoms and up to 4 heteroatoms, the heteroatoms being independently selected from one oxygen atom, one sulfur atom and up to 4 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O) or S(O) ₂ , each ring being unsubstituted or substituted with at least one substituent independently selected from the following group consisting of halogen, cyano, nitro, _C1 - _C4 alkyl, _C3 - _C6 cycloalkyl, _C1 -C _and each n is independently 0, 1 or 2; provided that when R ² , R ³ and R ⁴ are H and L is CH(OH), R ₁ is not _{3 -} trifluoromethyl; and when L is C(=O) _NR ⁷ wherein the nitrogen is attached to a benzene ring, at least one of R ² , R ³ or ^{R 4} is not H.

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 and combating invertebrate pests, the 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, the composition optionally further comprising at least one additional biologically active compound or agent.

The present disclosure also provides a method for controlling and combating invertebrate pests, the method comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound having Formula 1 , an N -oxide or a salt thereof (e.g., as a composition described herein). The present disclosure also relates to such a method, wherein the invertebrate pest or its environment is contacted with a composition comprising a biologically effective amount of a compound having 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, the composition optionally further comprising a biologically effective amount of at least one additional biologically active compound or agent.

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

The present disclosure also provides a method for controlling and combating invertebrate pests, the method comprising contacting the invertebrate pests or their environment with a biologically effective amount of any one of the above compositions, wherein the environment is an animal.

The present disclosure also provides a method for controlling and combating invertebrate pests, the method comprising contacting the invertebrate pests or their environment with a biologically effective amount of any one of the above compositions, wherein the environment is a seed.

The present disclosure also provides a method for protecting seeds from invertebrate pests, the method comprising contacting the seeds 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). The present disclosure also relates to treated seeds (i.e., seeds contacted with a compound of Formula 1 ).

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

The present disclosure further provides a method for protecting an animal from invertebrate parasitic pests, the method comprising administering to the animal a parasiticidally effective amount of a compound of Formula 1 , an N -oxide or a salt thereof (e.g., as a composition described herein). The present disclosure also provides the use of a compound of Formula 1 , an N -oxide or a salt thereof (e.g., as a composition described herein) in protecting an animal from invertebrate pests.

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

The transitional phrase "consisting of" excludes any unspecified element, step, or ingredient. If in a claim, this phrase renders the claim closed, excluding materials other than those stated, except for impurities normally associated therewith. When the phrase "consisting of" appears in a clause of the body of a claim rather than in the immediate preceding clause, the phrase limits only the elements stated in that clause; the claim as a whole does not exclude other elements.

The transition phrase "consisting essentially of" is used to qualify a composition or method as including materials, steps, features, components, or elements in addition to those literally disclosed, provided that such additional materials, steps, features, components, or elements do not materially affect the basic and novel characteristics of the claimed disclosure. The term "consisting essentially of" is intermediate between "comprising" and "consisting of."

When the applicant has defined an embodiment or a portion thereof using an open term such as "comprising", it should be understood that (unless otherwise stated) the specification should be interpreted as also describing the embodiment using the term "consisting essentially of" or "consisting of".

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

Similarly, the indefinite article "a/an" before an element or component of the present disclosure is intended to be non-restrictive with respect to the number of instances (i.e., occurrences) of the element or component. Therefore, "a or an" should be understood to include one or at least one, and the singular word form of an element or component also includes the plural, unless the number obviously means the singular.

As referred to in this disclosure, the term "invertebrate pests" includes arthropods, gastropods, nematodes and worms that are economically important as pests. The term "arthropods" includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans. The term "gastropods" includes snails, slugs and other Stylommatophora. The term "nematodes" includes members of the phylum Nematoda, such as herbivorous nematodes and worms that parasitize animals. The term "helminths" includes all parasitic worms, such as roundworms (Nematoda), heartworms (Secernentea), flukes (Platyhelminthes, Tematoda), acanthocephala (Acanthocephala), and tapeworms (Platyhelminthes, Cestoda).

In the context of the present disclosure, "controlling and combating invertebrate pests" means inhibiting the development of invertebrate pests (including mortality, feeding reduction and/or mating disruption), and related expressions are similarly defined.

The term "agronomy" refers to the production of field crops; such as for food and fiber, and includes the growth of maize or corn, soybeans and other legumes, rice, cereals (e.g., wheat, oats, barley, rye, and rice), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruit vegetables (e.g., tomatoes, peppers, eggplant, crucifers, and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone, and citrus), small fruits (e.g., berries and cherries), and other specialty crops (e.g., canola, sunflower, and olives).

The term "nonagriculture" refers to applications other than field crops, such as horticultural crops (e.g., greenhouse, nursery, or ornamental plants not grown in the field), residential, agricultural, commercial, and industrial structures, turf (e.g., sod farms, pastures, golf courses, lawns, athletic fields, etc.), wood products, stored products, agroforestry and vegetation management, public health (i.e., humans), and animal health (e.g., domestic animals such as pets, livestock, and poultry, and non-domestic animals such as wildlife).

The term "crop vigour" means the growth rate or biomass accumulation of a crop plant. An "increase in vigour" means an increase in growth or biomass accumulation of a crop plant relative to untreated control crop plants. The term "crop yield" means the return in quantity and quality of crop material obtained after harvesting a crop plant. An "increase in crop yield" means an increase in crop yield relative to untreated control crop plants.

The term "biologically effective amount" refers to an amount of a biologically active compound (e.g., a compound of Formula 1) sufficient to produce a desired biological effect when applied to (i.e., contacted with) an invertebrate pest to be controlled or its environment, or a plant, a seed from which the plant grows, or a locus of the plant (e.g., a growth medium) to protect the plant from damage by the invertebrate pest or for other desired effects (e.g., increasing plant vigor).

Non-agricultural applications include protecting animals from invertebrate parasitic pests by administering to the animals to be protected a parasiticidally effective (i.e., biologically effective) amount of the disclosed compounds (typically in the form of a composition formulated for veterinary use). As referred to in the present disclosure and the scope of the patent application, the terms "parasiticidal" and "parasiticidal" refer to observable effects on invertebrate parasitic pests to protect animals from pests. Parasiticidal effects are typically associated with reducing the presence or activity of target invertebrate parasitic pests. Such effects on pests include necrosis, death, slowed growth, reduced mobility or reduced ability to remain on or in the host animal, reduced feeding, and reproductive inhibition. Such effects on invertebrate parasitic pests and combating (including preventing, reducing or eliminating) parasitic infestations or infections of animals.

In the above description, the term "alkyl", used alone or in compound words such as "alkylthio" or "haloalkyl", includes straight or branched chain alkyl groups such as methyl, ethyl, n-propyl, isopropyl, or different butyl, pentyl, or hexyl isomers. "Alkenyl" includes straight or branched chain alkenes such as vinyl, 1-propenyl, 2-propenyl, and different butenyl, pentenyl, and hexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes straight or branched chain alkynes such as ethynyl, 1-propynyl, 2-propynyl, and different butynyl, pentynyl, and hexynyl isomers. "Alkynyl" may also include moieties consisting of multiple triple bonds, such as 2,5-hexadiynyl. "Alkylene" refers to a straight or branched alkanediyl. Examples of "alkylene" include CH ₂ , CH ₂ CH ₂ , CH(CH ₃ ), CH ₂ CH ₂ CH ₂ , CH ₂ CH(CH ₃ ) and different butene isomers. "Alkenylene" refers to a straight or branched alkenediyl containing one alkene bond. Examples of "alkenylene" include CH=CH, CH ₂ CH=CH, CH=C(CH ₃ ) and different butenylene isomers. "Alkynediyl" refers to a straight or branched alkynediyl containing one triple bond. Examples of "alkynylene" include C≡C, _CH2C≡C , _C≡CCH2 and different butynylene isomers.

"Alkoxy" includes, for example, methoxy, ethoxy, n-propoxy _, isopropoxy and _different butoxy _{, pentyloxy} and hexyloxy isomers. "Alkoxyalkyl" refers _to alkoxy substitution on _an alkyl group. Examples of "alkoxyalkyl" include _{CH3OCH2 , CH3OCH2CH2 , CH3CH2OCH2 , CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2} . "Alkoxyalkoxy" refers to alkoxy substitution on an alkoxy group. "Alkenyloxy" includes straight or branched alkenyloxy moieties. Examples of "alkenyloxy" include _H2C = _{CHCH2O ,} ( _CH3 ) _2C = _CHCH2O , _{( CH3} )CH= _CHCH2O , ( _CH3 )CH=C( _{CH3 ) CH2O} and _CH2 = _CHCH2CH2O . "Alkynyloxy" includes straight or branched _alkynyloxy moieties. Examples of _" alkynyloxy" include HC≡CCH2O, _CH3C≡CCH2O , and _{CH3C≡CCH2CH2O} . "Alkylthio" includes branched or straight alkylthio moieties such as methylthio, ethylthio, and different propylthio, butylthio, pentylthio, and hexylthio isomers. "Alkylsulfinyl" includes both mirror image isomers _of alkylsulfinyl. Examples of " _{alkylsulfinyl} " include _CH3S (O)-, _CH3CH2S (O ₎ -, _CH3CH2CH2S ( _O )-, ( _CH3 ) _2CHS (O)-, and different butylsulfinyl, pentylsulfinyl, and _{hexylsulfinyl} isomers. Examples of "alkylsulfonyl" include _CH3S (O) _2- , _CH3CH2S (O) _2- , _CH3CH2CH2S (O) _2- , ( _CH3 ) _2CHS (O) _{2- ,} and different butylsulfonyl, pentylsulfonyl, and hexylsulfonyl isomers _. "Alkylthioalkyl" refers to alkylthio substitution on an alkyl group. Examples _{of " alkylthioalkyl " include CH3SCH2} , _CH3SCH2CH2 , _CH3CH2SCH2 , _{CH3CH2CH2CH2SCH2 , and CH3CH2SCH2CH2 .} " _{Alkylthioalkoxy} " refers to alkylthio substitution on _an alkoxy group. _" Alkyldisulfanyl" refers to a branched or straight chain _{alkyldisulfanyl moiety} . Examples of "alkyldisulfide" include _CH3SS- , _CH3CH2SS- , _CH3CH2CH2SS- , ( _{CH3 ) 2CHSS-} , and different butyldisulfide and pentyldisulfide isomers. "Cyanoalkyl" _refers to an alkyl group substituted with a cyano group. Examples of "cyanoalkyl" include _NCCH2 , _NCCH2CH2 , and _CH3CH (CN) _{CH2 .} "Alkylamino", "dialkylamino", "alkenylthio", "alkenylsulfinyl", "alkenylsulfonyl", "alkynylthio", "alkynylsulfinyl", "alkynylsulfonyl" _and the like are defined similarly to the above examples.

"Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The term "alkylcycloalkyl" refers to alkyl substitution on the cycloalkyl portion, and includes, for example, ethylcyclopropyl, isopropylcyclobutyl, 3-methylcyclopentyl, and 4-methylcyclohexyl. The term "cycloalkylalkyl" refers to cycloalkyl substitution on the alkyl portion. Examples of "cycloalkylalkyl" include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to a straight or branched alkyl group. The term "cycloalkoxy" refers to cycloalkyl groups attached via an oxygen atom, such as cyclopentyloxy and cyclohexyloxy. "Cycloalkylalkoxy" refers to cycloalkylalkyl groups attached via an oxygen atom attached to an alkyl chain. Examples of "cycloalkylalkoxy" include cyclopropylmethoxy, cyclopentylethoxy, and other cycloalkyl moieties bonded to a straight or branched alkoxy group. "Cyanocycloalkyl" refers to a cycloalkyl group substituted with a cyano group. Examples of "cyanocycloalkyl" include 4-cyanocyclohexyl and 3-cyanocyclopentyl. "Cycloalkenyl" includes groups such as cyclopentenyl and cyclohexenyl and groups with more than one double bond such as 1,3-cyclohexadienyl and 1,4-cyclohexadienyl.

The term "halogen", alone or in compound words such as "halogenated alkyl", or when used in descriptions such as "halogenated alkyl", includes fluorine, chlorine, bromine or iodine. In addition, when used in compound words such as "halogenated alkyl", or when used in descriptions such as "halogenated alkyl", the alkyl group may be partially or completely substituted by halogen atoms (which may be the same or different). Examples of "halogenated alkyl" or "halogenated alkyl" include F ₃ C-, ClCH ₂ -, CF ₃ CH ₂ - and CF ₃ CCl ₂ -. The terms "halogenated cycloalkyl", "halogenated alkoxy", "halogenated alkylthio", "haloalkenyl", "halogenated alkynyl" and the like are defined similarly to the term "halogenated alkyl". Examples of “halogenated alkoxy” include CF ₃ O—, CCl ₃ CH ₂ O—, HCF ₂ CH ₂ CH ₂ O— and CF ₃ CH ₂ O—. Examples of “halogenated alkylthio” include CCl ₃ S—, CF ₃ S—, CCl ₃ CH ₂ S— and ClCH ₂ CH ₂ CH ₂ S—. Examples of “halogenated alkylsulfinyl” include CF ₃ S(O)—, CCl ₃ S(O)—, CF ₃ CH ₂ S(O)— and CF ₃ CF ₂ S(O)—. Examples of “halogenated alkylsulfonyl” include CF ₃ S(O) ₂ —, CCl ₃ S(O) ₂ —, CF ₃ CH ₂ S(O) ₂ — and CF ₃ CF ₂ S(O) ₂ —. Examples of "haloalkenyl" include (Cl) _2C = _{CHCH2- and CF3CH2CH} = _CHCH2- . _Examples of "haloalkynyl" include HC≡CCHCl-, _CF3C≡C- , _{CCl3C≡C- and FCH2C≡CCH2- . Examples} of "haloalkoxyalkoxy" include _{CF3OCH2O- , ClCH2CH2OCH2CH2O-} , _{Cl3CCH2OCH2O- and} branched alkyl _derivatives .

"Alkylcarbonyl" means a straight or branched alkyl moiety bonded 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 ) - , and} different butoxy- or pentoxy-carbonyl isomers.

As used herein, the chemical abbreviations S(O) and S(=O) represent a sulfinyl moiety. As used herein, the chemical abbreviations SO ₂ , S(O) ₂ and S(=O) ₂ represent a sulfonyl moiety. As used herein, the chemical abbreviations C(O) and C(=O) represent a carbonyl moiety. As used herein, the chemical abbreviations CO ₂ , C(O)O and C(=O)O represent an oxycarbonyl moiety. “CHO” means methacryl.

When R ²⁵ is a 5- to 6-membered heterocyclic aromatic ring substituted with at least one substituent selected from the group of substituents as described in the present invention, the substituent may be attached to the remainder of the compound having Formula 1 through any available ring member of the heterocyclic ring.

When ^Qa or ^Qb is a 5 or 6 membered heterocyclic aromatic ring substituted with at least one substituent as described in the present invention, the substituent may be attached to the remainder of the compound of Formula 1 via any available ring member of the 5 or 6 membered ring.

When a variable group is shown as optionally attached to a position (e.g., ( ^R1 ) _m , where r can be 0), then a hydrogen may be present at that position even if it is not mentioned in the definition of the variable group. When one or more positions on a group are referred to as being "not substituted" or "unsubstituted," then hydrogen atoms are attached to take up any free valencies.

The total number of carbon atoms in a substituent group is indicated by a " _Ci - _Cj " prefix, where i and j are numbers from 1 to 10. For example, _C1 - _C4 alkylsulfonyl represents methylsulfonyl to butylsulfonyl; _C2 alkoxyalkyl represents _CH3OCH2- ; _C3 alkoxyalkyl represents, for example, _CH3CH ( _OCH3 )-, _CH3OCH2CH2- , or _CH3CH2OCH2- ; _{and C4} alkoxyalkyl represents different _isomers of an alkyl group substituted _with an _alkoxy group containing a total _{of four carbon} atoms, examples _{of which} include _{CH3CH2CH2OCH2- and CH3CH2OCH2CH2- .}

When a compound is substituted with substituents bearing a subscript indicating that the number of such substituents may exceed 1, the substituents (when they exceed 1) are independently selected from the defined group of substituents, (e.g., [(R ¹ ) _m ], m is 0, 1, 2, 3, 4, or 5). When a group contains a substituent that may be hydrogen, such as R ² , R ³ , or R ⁴ , then when the substituent is hydrogen, this is recognized as equivalent to the group being unsubstituted. When one or more positions on a group are referred to as being "not substituted" or "unsubstituted," hydrogen atoms are attached to take up any free valencies.

Unless otherwise indicated, a "ring" or "ring system" as a component of Formula 1 is a carbocyclic or heterocyclic ring. The term "ring system" means two or more fused rings. The terms "bicyclic system" and "fused bicyclic system" mean a ring system consisting of two fused rings, which ring system may be "ortho-fused", "bridged bicyclic" or "spirobicyclic". "Ortho-fused bicyclic system" means a ring system in which the two constituent rings have two adjacent atoms in common. "Bridged bicyclic system" is formed by bonding a chain segment of one or more atoms to non-adjacent ring members of the ring. A "spirobicyclic system" is formed by bonding a chain of two or more atoms to the same ring member of a ring. The term "fused heterobicyclic system" refers to a fused bicyclic 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.

The term "carbocyclic ring", "carbocycle" or "carbocyclic ring system" means a ring or a ring system in which the atoms forming the ring skeleton are selected only from carbon. The term "heterocyclic ring", "heterocycle" or "heterocyclic ring system" means a ring or a ring system in which at least one atom forming the ring skeleton is not carbon (e.g., nitrogen, oxygen or sulfur). Typically, a heterocycle contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, a carbocyclic ring or a heterocyclic ring may be a saturated or unsaturated ring. "Saturated" refers to a ring having a backbone consisting of atoms connected to each other by single bonds; unless otherwise specified, the remaining atomic valences are occupied by hydrogen atoms. 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 the atoms in the ring are single bonds or double bonds according to the valence bond theory and furthermore the bonds between the atoms in the ring include as many double bonds as possible but no cumulative double bonds (i.e. no C=C=C or C=C=N). The term "partially unsaturated ring" refers to a ring that comprises at least one ring member bonded to an adjacent ring member by a double bond and that conceptually could accommodate a number of non-cumulative double bonds between adjacent ring members (i.e., in its fully unsaturated counterpart) greater than the number of double bonds present (i.e., in its partially unsaturated form).

Unless otherwise indicated, heterocyclic and ring systems may be attached through any available carbon or nitrogen by replacing a hydrogen on that carbon or nitrogen.

"Aromatic" means that each ring atom is substantially in the same plane and has a p -orbital perpendicular to the plane of the ring and that (4n + 2) pi electrons (where n is a positive integer) are associated with the ring in accordance with Hückel's rule. The term "aromatic ring system" means a carbocyclic or heterocyclic ring system in which at least one ring of the ring system is aromatic. When a fully unsaturated carbon ring satisfies Hückel's rule, the ring is also referred to as an "aromatic ring" or "aromatic carbocyclic ring".

The term "aromatic carbocyclic system" means a carbocyclic system in which at least one ring in the ring system is aromatic. When a completely unsaturated heterocyclic ring satisfies Hückel's rule, the ring is also called a "heteroaromatic ring" or "aromatic heterocyclic ring". The term "aromatic heterocyclic system" means a heterocyclic system in which at least one ring in the ring system is aromatic. The term "non-aromatic ring system" means a carbocyclic or heterocyclic system that may be completely saturated, as well as partially or completely unsaturated, provided that none of the rings in the ring system is aromatic. The term "non-aromatic carbocyclic system" means a carbocyclic ring in which no ring in the ring system is aromatic. The term "non-aromatic heterocyclic system" refers to a heterocyclic system in which none of the rings in the ring system is aromatic.

The term "optionally substituted" in relation to heterocycles refers to groups that are unsubstituted or have at least one non-hydrogen substituent that does not eliminate the biological activity possessed by the unsubstituted analog. As used herein, the following definitions apply unless otherwise indicated. The term "optionally substituted" is used interchangeably with the phrase "substituted or unsubstituted" or with the term "(un)substituted". Unless otherwise indicated, an optionally substituted group may have a substituent at each substitutable position of the group, and each substitution is independent of the others.

As described above, substituents such as ^Qa or ^Qb may be (especially) 5- or 6-membered heterocyclic aromatic rings optionally substituted with one or more substituents selected from the group of substituents defined in the present invention. Examples of 5- or 6-membered unsaturated aromatic heterocyclic rings optionally substituted with one or more substituents include rings U-2 to U-61 shown in Example 1, wherein ^Rv is any substituent as defined in the present invention, and r is an integer from 1 to 4, subject to the number of available positions on each U group. Since U-29, U-30, U-36, U-37, U-38, U-39, U-40, U-41, U-42 and U-43 have only one available position, r is limited to the integer 1 for these U groups, and when ^Rv is H and r is 1, it means that the U group is unsubstituted and hydrogen is present at the position indicated by ( ^Rv ) _r . Example 1 , , , , U-2 U-3 U-4 U-5 , , , , , U-6 U-7 U-8 U-9 U-10 , , , , , U-11 U-12 U-13 U-14 U-15 , , , , , U-16 U-17 U-18 U-19 U-20 , , , , , U-21 U-22 U-23 U-24 U-25 , , , , , U-26 U-27 U-28 U-29 U-30 , , , , , U-31 U-32 U-33 U-34 U-35 , , , , , U-36 U-37 U-38 U-39 U-40 , , , , , U-41 U-42 U-43 U-44 U-45 , , , , U-46 U-47 U-48 U-49 , , , , U-52 U-53 U-54 U-55 , , , , as well as U-56 U-57 U-58 U-59 U-60 . U-61

It should be noted that when the substituent is a 5- or 6-membered saturated or unsaturated and non-aromatic heterocyclic ring optionally substituted with one or more substituents selected from the group of substituents as defined in the present invention, one or two carbon ring members of the heterocyclic ring may optionally be an oxidized form of a carbonyl moiety.

Examples of 5- or 6-membered saturated or non-aromatic unsaturated heterocyclic rings include rings G-1 to G-35 as shown in Example 2. It should be noted that when the attachment point on the G group is shown as floating, the G group can be attached to the rest of Formula 1 through any available carbon or nitrogen of the G group by replacing a hydrogen atom. Optional substituents, hereinafter referred to as ^Rv as described in the invention, can be attached to any available carbon or nitrogen by replacing a hydrogen atom. For these G rings, s is typically an integer from 1 to 5, limited by the number of available positions on each G group.

It should be noted that when the substituent comprises a ring selected from G-28 to G-35, ^G2 is selected from O, S or N. It should be noted that when ^G2 is N, the nitrogen atom can be substituted with a substituent corresponding to ^R as defined in the present invention to complete its valence. Example 2 , , , , , G-1 G-2 G-3 G-4 G-5 , , , , , G-6 G-7 G-8 G-9 G-10 , , , , , G-11 G-12 G-13 G-14 G-15 , , , , , G-16 G-17 G-18 G-19 G-20 , , , , , G-21 G-22 G-23 G-24 G-25 , , , , , G-26 G-27 G-28 G-29 G-30 , , , and . G-31 G-32 G-33 G-34 G-35

Although ^Rv groups are shown in structures U-2 to U-61, it should be noted that they do not have to be present because they are optional substituents. It should be noted that when ^Rv is H attached to an atom, this is unsubstituted as the atom. Nitrogen atoms that need to be substituted to fill their valence are replaced by H or ^Rv . It should be noted that when the attachment point between ( ^Rv ) _r and the U ring is shown as floating, ( ^Rv ) _r can be attached to any available carbon or nitrogen atom of the U ring. It should be noted that when the attachment point on the U ring is shown as floating, the U group can be attached to the remainder of Formula 1 by replacing a hydrogen atom through any available carbon or nitrogen of the U group. It should be noted that some U rings can only be substituted with fewer than 4 ^Rv groups (e.g., U-2 to U-5, U-7 to U-49, and U-52 to U-61).

A variety of synthetic methods are known in the art that enable the preparation of aromatic and nonaromatic heterocycles and ring systems; for extensive reviews, see the eight-volume set Comprehensive Heterocyclic Chemistry, ed. AR Katritzky and CW Rees, Pergamon Press, Oxford, 1984, and the twelve-volume set Comprehensive Heterocyclic Chemistry II , ed. AR Katritzky, CW Rees and EFV Scriven, Pergamon Press, Oxford, 1996.

The compounds disclosed herein may exist as one or more stereoisomers. Stereoisomers are isomers that are identical in constitution but differ in the arrangement of their atoms in space, and include mirror image isomers, non-mirror image isomers, cis-trans isomers (also known as geometric isomers), and configurational isomers. Configurational isomers arise from restricted rotation around a single bond, where the rotational barrier is high enough to allow separation of isomeric species. Those skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when concentrated relative to one or more other stereoisomers, or when separated from one or more other stereoisomers. In addition, those skilled in the art know how to separate, enrich and/or selectively prepare the stereoisomers. For a comprehensive discussion of all aspects of stereoisomerism, see Ernest L. Eliel and Samuel H. Wilen, Stereochemistry of Organic Compounds , John Wiley & Sons, 1994.

To indicate stereochemistry, bonds that extend out of the drawing plane and toward the viewer are represented by solid wedges with the wide end of the wedge attached to an atom that extends out of the drawing plane and toward the viewer. Bonds that extend below the drawing plane and away from the viewer are represented by dashed wedges with the wide end of the wedge attached to an atom further away from the viewer. A wavy bond indicates that the stereochemistry of the bond is unknown.

Compounds having Formula 1 may contain chiral centers. For example, substituents on Formula 1 may contain chiral centers. The present disclosure includes racemic mixtures as well as enriched and substantially pure stereoconfigurations at such additional chiral centers.

The compounds of the present disclosure may exist as one or more conformational isomers due to the restricted rotation about any bond in Formula 1. The present disclosure includes mixtures of conformational isomers. Those skilled in the art will appreciate that not all nitrogen-containing heterocycles can form N- oxides, since nitrogen requires an available lone electron pair to oxidize 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 heterocyclic and tertiary amines are well known to those skilled in the art and include oxidation of heterocyclic and tertiary amines using peroxyacids such as peracetic acid and 3-chloroperoxybenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as tertiary butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane. Such methods for the preparation of N -oxides have been extensively described and reviewed in the literature, see, for example: TL Gilchrist, Comprehensive Organic Synthesis , Vol. 7, pp. 748-750, ed. SV Ley, Pergamon Press; M. Tisler and B. Stanovnik, Comprehensive Heterocyclic Chemistry, Vol. 3, pp. 18-20, ed. AJ Boulton and A. McKillop, Pergamon Press; MR Grimmett and BRT Keene, Advances in Heterocyclic Chemistry, Vol. 43, pp. 149-161, ed. AR Katritzky, Academic Press; M. Tisler and B. Stanovnik, Advances in Heterocyclic Chemistry , Vol. 43, pp. 149-161, ed. AR Katritzky, Academic Press; Advances in Heterocyclic Chemistry, vol. 9, pp. 285-291, AR Katritzky and AJ Boulton, eds., Academic Press; and GWH Cheeseman and ESG Werstiuk, Advances in Heterocyclic Chemistry, vol. 22, pp. 390-392, AR Katritzky and AJ Boulton, eds., Academic Press.

Those skilled in the art recognize that, because salts of compounds are in equilibrium with their corresponding non-salt forms in the environment and under physiological conditions, the salts share the biological utility of the non-salt forms. Therefore, a variety of salts of compounds of Formula 1 can be used to control and combat invertebrate pests. Salts of compounds of Formula 1 include acid addition salts formed 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 the compound of formula 1 contains an acidic moiety such as a carboxylic acid or a phenol, salts also include those formed with organic or inorganic bases such as pyridine, triethylamine or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium. Thus, the present disclosure includes compounds selected from formula 1 , N- oxides thereof and suitable salts.

Compounds selected from Formula 1 , stereoisomers, tautomers, N -oxides and salts thereof typically exist in more than one form, and thus Formula 1 includes all crystalline and non-crystalline forms of the compounds represented by Formula 1. Non-crystalline forms include embodiments that are solids such as waxes and resins, and embodiments that are liquids such as solutions and melts. Crystalline forms include embodiments that represent essentially single crystal types and embodiments that represent mixtures of isomorphs (i.e., different crystalline types). The term "isomorphs" refers to specific crystalline forms of a compound that can crystallize in different crystalline forms, which have different molecular arrangements and/or configurations in the crystal lattice. Although isomorphs may have the same chemical composition, they may also differ in composition due to the presence or absence of eutectic water or other molecules, which may be weakly or strongly bound within the crystal lattice. Isomorphs may differ in such chemical, physical, and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspendability, dissolution rate, and bioavailability. Those skilled in the art will appreciate that an isomorph of a compound represented by Formula 1 may exhibit beneficial effects (e.g., suitability for preparing useful formulations, improved biological properties) relative to another isomorph or mixture of isomorphs of the same compound represented by Formula 1 . The preparation and separation of specific isomorphs of the compounds represented by Formula 1 can be achieved by methods known to those skilled in the art, including, for example, crystallization using selected solvents and temperatures. The compounds of the present disclosure may exist as one or more crystalline isomorphs. The present disclosure encompasses both individual isomorphs and mixtures of isomorphs, including mixtures in which one isomorph is enriched relative to the other. For a comprehensive discussion of polymorphism, see R. Hilfiker, ed., Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006.

The embodiments of the present disclosure as described in the invention include those described below. In the following embodiments, unless further defined in the embodiments, Formula 1 includes stereoisomers, N -oxides and salts thereof, and reference to "compounds having Formula 1 " includes the definitions of substituents specified in the invention.

Embodiment 1: A compound of Formula 1 , wherein L is CR ⁵ R ⁶ , CR ⁵ R ⁶ CR ⁵ R ⁶ , OCR ⁵ R ⁶ , CR ⁵ R ⁶ O; CR ⁵ R ⁶ NR ⁷ , NR ⁷ CR ^{5 R 6 ,} C(=E)NR ⁷ , NR ⁷ C(=E), C(=E) CR ⁵ R ⁶ , CR ⁵ R ⁶ C(=E), C(=CR ⁵ R ⁶ ) or CR ⁵ =CR ⁶ .

Embodiment 1a: A compound of formula 1 , wherein L is CR ⁵ R ⁶ , CR ⁵ R ⁶ CR ⁵ R ⁶ , OCR ⁵ R ⁶ , CR ⁵ R ⁶ O; CR ⁵ R ⁶ NR ⁷ or NR ⁷ CR ⁵ R ⁶ .

Embodiment 1b: The compound of formula 1 as described in Embodiment 1, wherein L is C(=E)NR ⁷ , NR ⁷ C(=E), C(=E) CR ⁵ R ⁶ , CR ⁵ R ⁶ C(=E), C(=CR ⁵ R ⁶ ) or CR ⁵ ═CR ⁶ .

Embodiment 1c: The compound of formula 1 as described in Embodiment 1, wherein L is CR ⁵ R ⁶ .

Embodiment 1d: The compound of formula 1 as described in Embodiment 1, wherein L is CR ⁵ R ⁶ CR ⁵ R ⁶ .

Embodiment 1e: The compound of formula 1 as described in Embodiment 1, wherein L is OCR ⁵ R ⁶ .

Embodiment f: The compound of formula 1 as described in Embodiment 1a, wherein L is CR ⁵ R ⁶ O.

Embodiment 1g: The compound of formula 1 as described in embodiment 1a, wherein L is CR ⁵ R ⁶ NR ⁷ .

Embodiment 1h: The compound of formula 1 as described in Embodiment 1a, wherein L is NR ⁷ CR ⁵ R ⁶ .

Embodiment 1i: The compound of formula 1 as described in embodiment 1a, wherein L is C(=E)NR ⁷ .

Embodiment 1j: The compound of formula 1 as described in Embodiment 1a, wherein L is NR ⁷ C(=E).

Embodiment 1k: The compound of formula 1 as described in embodiment 1a, wherein L is C(=E)CR ⁵ R ⁶ .

Embodiment 11: The compound of formula 1 as described in Embodiment 1a, wherein L is CR ⁵ R ⁶ C(=E).

Embodiment 1m: The compound of formula 1 as described in embodiment 1a, wherein L is C (=CR ⁵ R ⁶ ).

Embodiment 1n: The compound of formula 1 as described in embodiment 1a, wherein L is CR ⁵ ═CR ⁶ .

Embodiment 2: The compound of formula 1 as described in any one of Embodiments 1, 1b, 1i, 1j, 1k or 11, wherein E is O or S.

Embodiment 2a: The compound of formula 1 as described in Embodiment 2, wherein E is O.

Embodiment 2b: The compound of formula 1 as described in Embodiment 2, wherein E is S.

Embodiment 2c: The compound of formula 1 as described in Embodiment 2, wherein E is NR ⁸ .

Embodiment 3: The compound of formula 1 as described in any one of the preceding embodiments, wherein R ¹ is halogen, cyano, nitro, hydroxyl, SF ₅ , C(O)NH ₂ , C(O)NR ¹⁰ R ¹¹ , C(=NR ¹³ )NR ¹⁰ R ¹¹ , C(=NR ¹³ )R ¹⁴ , OC(O)R ¹⁴ , NR ¹⁰ R ¹¹ , NR ¹³ C(O)R ¹⁴ , C(O)R ¹⁴ , S(O) _n R ¹⁴ , OS(O) _n R ¹⁴ , Si(R ¹⁴ ) ₃ , OSi(R ¹⁴ ) ₃ or MQ ^a ; or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₆ cycloalkyl, C ₁ -C 6 _{C 6} alkoxy, C ₃ -C ₆ cycloalkoxy, which is unsubstituted or substituted by at least one R ^x ;

Embodiment 3a: A compound of formula 1 as described in any of the preceding embodiments, wherein R ¹ is S(O) _n R ¹⁴ or OS(O) _n R ¹⁴ ; or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ cycloalkoxy, which is unsubstituted or substituted by at least one R ^x ;

Embodiment 3b: A compound of formula 1 as described in any of the preceding embodiments, wherein R ¹ is S(O) _n R ¹⁴ ; or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ cycloalkoxy, which is unsubstituted or substituted by at least one R ^x ;

Embodiment 3c: A compound of formula 1 as described in any of the preceding embodiments, wherein R ¹ is S(O) _n R ¹⁴ ; or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₆ cycloalkyl or C ₁ -C ₆ alkoxy, which is unsubstituted or substituted with at least one R ^x ;

Embodiment 3d: A compound of formula 1 as described in any of the preceding embodiments, wherein R ¹ is S(O) _n R ¹⁴ ; or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl or C ₁ -C ₆ alkoxy, which is unsubstituted or substituted with at least one R ^x ;

Embodiment 3e: A compound of formula 1 as described in any of the preceding embodiments, wherein R ¹ is S(O) _n R ¹⁴ ; or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₁ -C ₆ alkoxy or C ₁ -C ₆ alkoxy, which is unsubstituted or substituted with at least one R ^x ;

Embodiment 3f: A compound of formula 1 as described in any of the preceding embodiments, wherein R ¹ is S(O) _n R ¹⁴ ; or C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy, which is unsubstituted or substituted with at least one R ^x ;

Embodiment 3g: The compound of formula 1 as described in any one of Embodiments 1-2b, wherein R ¹ is MQ ^a .

Embodiment 3h: The compound of formula 1 as described in Embodiment 3e, wherein M is a direct bond, O, S, S(O), S(O) ₂ or NR ⁹ .

Embodiment 3i: The compound of formula 1 as described in Embodiment 3f, wherein M is a direct bond, O, S, S(O), S(O) ₂ or S(O) ₂ .

Embodiment 3j: The compound of formula 1 as described in Embodiment 3g, wherein M is a direct bond or S, S(O) or S(O) ₂ .

Embodiment 3k: A compound of formula 1 as described in Embodiment 3j, wherein M is a direct bond or O.

Embodiment 3i: A compound of formula 1 as described in any one of embodiments 3g to 3k, wherein each ^Qa is independently phenyl, a 5- or 6-membered heterocyclic aromatic ring or a 3- to 6-membered heterocyclic non-aromatic ring, each ring contains ring members selected from carbon atoms and up to 4 heteroatoms, the heteroatoms are independently selected from one oxygen atom, one sulfur atom and up to 4 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O) or S(O) 2, each ring is unsubstituted or substituted with at least one substituent independently selected from the following group, the group consisting of the following: halogen, cyano, nitro, C 1 -C 4 alkyl, C 3 -C 4 alkyl, C 3 -C 4 alkyl, C 3 -C 4 alkyl, C 3 -C 4 alkyl, C 3 -C 4 alkyl, C 3 -C 4 alkyl, C 3 -C ₄ alkyl, C 3 -C 4 alkyl, C 3 -C 4 alkyl, C 3 -C 4 alkyl, C 3 -C 4 alkyl, C 3 -C 4 alkyl, C 3 -C 4 alkyl, C 3 -C 4 alkyl, C 3 -C 4 alkyl, C 3 -C 4 alkyl, C ₃ -C ₄ alkyl, C 3 -C 4 alkyl, C ₃ -C 4 alkyl, C The invention _also includes a C ₁ -C ₄ cycloalkyl group, a C 1 -C 4 halogenated alkyl group, a C ₁ -C ₄ alkoxy group and a C ₁ -C ₄ halogenated alkoxy group.

Embodiment 4: The compound of formula 1 as described in any one of the preceding embodiments, wherein R ² is hydrogen, halogen, cyano, nitro, hydroxyl, SF ₅ , C(O)H, C(O)NH ₂ , C(O)NR ¹⁰ R ¹¹ , C(=NR ¹³ )NR ¹⁰ R ¹¹ , C(=NR ¹³ )R ¹⁴ , OC(O)R ¹⁴ , NR ¹⁰ R ¹¹ , NR ¹³ C(O)R ¹⁴ , C(O)R ¹⁴ , S(O) _n R ¹⁴ , OS(O) _n R ¹⁴ , Si(R ¹⁴ ) ₃ , OSi(R ¹⁴ ) ₃ or MQ ^a ; C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₃ -C 6 C ₂ -C ₆ cycloalkoxy, C 2 -C ₆ alkenyl or C ₂ -C ₆ alkynyl, which is unsubstituted or substituted by at least one R ^x ;

Embodiment 4a: A compound of formula 1 as described in any of the preceding embodiments, wherein R ² is hydrogen, halogen, cyano, nitro, hydroxyl, SF ₅ , C(O)NH ₂ , C(O)NR ¹⁰ R ¹¹ , C(=NR ¹³ )NR ¹⁰ R ¹¹ , C(=NR ¹³ )R ¹⁴ , OC(O)R ¹⁴ , NR ¹⁰ R ¹¹ , NR ¹³ C(O)R ¹⁴ , C(O)R ¹⁴ , S(O) _n R ¹⁴ , OS(O) _n R ¹⁴ , Si(R ¹⁴ ) ₃ , OSi(R ¹⁴ ) ₃ or MQ ^a ; or C ₁ -C ₆ alkyl.

Embodiment 4b: A compound of formula 1 as described in any one of the preceding embodiments, wherein R ² is hydrogen, halogen, cyano, nitro or hydroxyl; or C ₁ -C ₆ alkyl.

Embodiment 4c: The compound of formula 1 as described in any one of the preceding embodiments, wherein R ² is hydrogen or halogen; or C ₁ -C ₆ alkyl.

Embodiment 4d: A compound of formula 1 as described in any of the preceding embodiments, wherein R ² is hydrogen.

Embodiment 4e: The compound of formula 1 as described in any one of embodiments 1-4c, wherein R ² is C ₁ -C ₆ alkyl.

Embodiment 5: The compound of formula 1 as described in any one of the preceding embodiments, wherein R ³ is hydrogen, halogen, cyano, nitro, hydroxyl, SF ₅ , C(O)H, C(O)NH ₂ , C(O)NR ¹⁰ R ¹¹ , C(=NR ¹³ )NR ¹⁰ R ¹¹ , C(=NR ¹³ )R ¹⁴ , OC(O)R ¹⁴ , NR ¹⁰ R ¹¹ , NR ¹³ C(O)R ¹⁴ , C(O)R ¹⁴ , S(O) _n R ¹⁴ , OS(O) _n R ¹⁴ , Si(R ¹⁴ ) ₃ , OSi(R ¹⁴ ) ₃ or MQ ^a ; or C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₃ -C 6 C ₂ -C ₆ cycloalkoxy, C 2 -C ₆ alkenyl or C ₂ -C ₆ alkynyl, which is unsubstituted or substituted by at least one R ^x .

Embodiment 5a: The compound of formula 1 as described in any of the preceding embodiments, wherein R ³ is hydrogen, halogen, cyano, nitro, hydroxyl, SF ₅ , C(O)NH ₂ , C(O)NR ¹⁰ R ¹¹ , C(=NR ¹³ )NR ¹⁰ R ¹¹ , C(=NR ¹³ )R ¹⁴ , OC(O)R ¹⁴ , NR ¹⁰ R ¹¹ , NR ¹³ C(O)R ¹⁴ , C(O)R ¹⁴ , S(O) _n R ¹⁴ , OS(O) _n R ¹⁴ , Si(R ¹⁴ ) ₃ , OSi(R ¹⁴ ) ₃ or MQ ^a ; or C ₁ -C ₆ alkyl or C ₃ -C ₆ cycloalkyl.

Embodiment 5b: A compound of formula 1 as described in any one of the preceding embodiments, wherein R ³ is hydrogen, halogen, cyano, nitro or hydroxyl; or C ₁ -C ₆ alkyl or C ₃ -C ₆ cycloalkyl.

Embodiment 5c: A compound of formula 1 as described in any one of the preceding embodiments, wherein R ³ is hydrogen or halogen; or C ₁ -C ₆ alkyl or C ₃ -C ₆ cycloalkyl.

Embodiment 5d: The compound of formula 1 as described in any one of the preceding embodiments, wherein R ³ is H, C ₁ -C ₆ alkyl or C ₃ -C ₆ cycloalkyl.

Embodiment 5e: A compound of formula 1 as described in any of the preceding embodiments, wherein R ³ is H, Me or c -Pr.

Embodiment 5f: A compound of formula 1 as described in any of the preceding embodiments, wherein R ³ is Me or c -Pr.

Embodiment 5g: A compound of formula 1 as described in any of the preceding embodiments, wherein R ³ is Me.

Embodiment 5f: A compound of formula 1 as described in any of the preceding embodiments, wherein R ³ is c -Pr.

Embodiment 6: The compound of formula 1 as described in any one of the preceding embodiments, wherein R ⁴ is hydrogen, halogen, cyano, nitro, hydroxyl, SF ₅ , C(O)H, C(O)NH ₂ , C(O)NR ¹⁰ R ¹¹ , C(=NR ¹³ )NR ¹⁰ R ¹¹ , C(=NR ¹³ )R ¹⁴ , OC(O)R ¹⁴ , NR ¹⁰ R ¹¹ , NR ¹³ C(O)R ¹⁴ , C(O)R ¹⁴ , S(O) _n R ¹⁴ , OS(O) _n R ¹⁴ , Si(R ¹⁴ ) ₃ , OSi(R ¹⁴ ) ₃ or MQ ^a ; or C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₃ -C 6 C ₂ -C ₆ cycloalkoxy, C 2 -C ₆ alkenyl or C ₂ -C ₆ alkynyl, which is unsubstituted or substituted by at least one R ^x .

Embodiment 6a: The compound of formula 1 as described in any of the preceding embodiments, wherein R ⁴ is hydrogen, halogen, cyano, nitro, hydroxyl, SF ₅ , C(O)NH ₂ , C(O)NR ¹⁰ R ¹¹ , C(=NR ¹³ )NR ¹⁰ R ¹¹ , C(=NR ¹³ )R ¹⁴ , OC(O)R ¹⁴ , NR ¹⁰ R ¹¹ , NR ¹³ C(O)R ¹⁴ , C(O)R ¹⁴ , S(O) _n R ¹⁴ , OS(O) _n R ¹⁴ , Si(R ¹⁴ ) ₃ , OSi(R ¹⁴ ) ₃ or MQ ^a ; or C ₁ -C ₆ alkyl.

Embodiment 6b: A compound of formula 1 as described in any one of the preceding embodiments, wherein R ⁴ is hydrogen, halogen, cyano, nitro or hydroxyl; or C ₁ -C ₆ alkyl.

Embodiment 6c: The compound of formula 1 as described in any one of the preceding embodiments, wherein R ⁴ is hydrogen or halogen; or C ₁ -C ₆ alkyl.

Embodiment 6d: A compound of formula 1 as described in any of the preceding embodiments, wherein R ⁴ is hydrogen.

Embodiment 6e: The compound of formula 1 as described in any one of Embodiments 1-6c, wherein R ⁴ is Me.

Embodiment 6f: A compound of formula 1 as described in any one of Embodiments 1-6c, wherein R ⁴ is F.

Embodiment 7: A compound of formula 1 as described in any one of Embodiments 1-1e and 3-6f, wherein ^R5 and ^R6 are independently hydrogen, hydroxyl, halogen, cyano, _C1 - _C6 alkyl, _C3 -C6 cycloalkyl, _C1 - _C6 halogenated alkyl, C1- _C6 alkoxy, _C1 - _{C6 halogenated} alkoxy, _C3 - _C6 cycloalkoxy, _C1 - _{C6 alkylthio} or _C1 - _C6 halogenated alkylthio.

Embodiment 7a: A compound of formula 1 as described in any one of Embodiments 1-1e and 3-7, wherein ^R5 and ^R6 are independently hydrogen, hydroxyl, halogen, cyano, _C1 - _C6 alkyl, _C3 - _C6 cycloalkyl, _{C1 - C6} halogenated alkyl, C1- _C6 alkoxy, _C1 -C6 halogenated alkoxy, _{C3 -C6 cycloalkoxy} or _C1 - _C6 alkylthio.

Embodiment 7b: A compound of formula 1 as described in any one of Embodiments 1-1e and 3-7a, wherein ^R5 and ^R6 are independently hydrogen, hydroxyl, halogen, cyano, _C1 - _C6 alkyl, _C3 - _C6 cycloalkyl, _C1 - _C6 halogenated alkyl, _C1 - _C6 alkoxy, _C1 - _C6 halogenated alkoxy or C3- _{C6 cycloalkoxy} .

Embodiment 7c: A compound of formula 1 as described in any one of Embodiments 1-1e and 3-7b, wherein ^R5 and ^R6 are independently hydrogen, hydroxyl, halogen, cyano, _C1 - _C6 alkyl, _C3 - _C6 cycloalkyl, _C1 - _C6 halogenated alkyl, _C1 - _C6 alkoxy or _C1 - _C6 halogenated alkoxy.

Embodiment 7d: A compound of formula 1 as described in any one of embodiments 1-1e and 3-7c, wherein ^R5 and ^R6 are independently hydrogen, hydroxyl, halogen, cyano, _C1 - _C6 alkyl, _C3 - _C6 cycloalkyl, _C1 - _C6 halogenated alkyl or _C1 - _C6 alkoxy.

Embodiment 7e: The compound of formula 1 as described in any one of embodiments 1-1e and 3-7d, wherein R ⁵ and R ⁶ are independently hydrogen, hydroxyl, halogen, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy or C ₃ -C ₆ cycloalkyl.

Embodiment 7f: A compound of formula 1 as described in any one of Embodiments 1-1e and 3-7e, wherein R ⁵ and R ⁶ are independently hydrogen, hydroxyl, halogen, cyano, C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy.

Embodiment 7g: The compound of formula 1 as described in any one of embodiments 1-1e and 3-7f, wherein R ⁵ and R ⁶ are independently hydrogen, hydroxyl, halogen, C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy.

Embodiment 7h: The compound of formula 1 as described in any one of Embodiments 1-1e and 3-7g, wherein R ⁵ and R ⁶ are independently hydrogen, halogen, C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy.

Embodiment 7i: The compound of formula 1 as described in any one of embodiments 1-1e and 3-7h, wherein R ⁵ and R ⁶ are independently hydrogen, halogen or C ₁ -C ₆ alkoxy.

Embodiment 7j: A compound of formula 1 as described in any one of Embodiments 1-1e and 3-7i, wherein R ⁵ and R ⁶ are independently hydrogen, F or MeO.

Embodiment 7k: A compound of formula 1 as described in any one of Embodiments 1-1e and 3-6f, wherein R ⁵ and R ⁶ each attached to the same carbon together with the carbon atom to which they are attached form a 3- to 7-membered ring containing ring members selected from carbon atoms and up to 3 heteroatoms, the heteroatoms being independently selected from one oxygen atom, one sulfur atom and up to 3 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are selected from S, S(O) or S(O) ₂ , the ring being unsubstituted or substituted with at least one R ^x ; or in the case of CR ⁵ R ⁶ CR ⁵ R ⁶ , each R ⁵ and R ⁶ are attached to each of the first and second adjacent carbon atoms and can form, together with the carbon atoms to which they are attached, a 3 to 7 membered ring containing ring members selected from carbon atoms and up to 3 heteroatoms, the heteroatoms being independently selected from one oxygen atom, one sulfur atom and up to 3 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are selected from S, S(O) or S(O) ₂ , the ring being unsubstituted or substituted with at least one R ^x .

Embodiment 7i: A compound of formula 1 as described in any one of Embodiments 1-1e and 3-6f, wherein R ⁵ and R ⁶ each attached to the same carbon together with the carbon atom to which they are attached form a 3- to 7-membered ring containing ring members selected from carbon atoms and up to 3 heteroatoms, wherein the heteroatoms are independently selected from one oxygen atom, one sulfur atom and up to 3 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring member is selected from S, S(O) or S(O) ₂ , and the ring is unsubstituted or substituted with at least one R ^x .

Embodiment 7j: A compound of formula 1 as described in any one of Embodiments ^1-1e and 3-6f, wherein in the case of ^CR5R6CR5R6 , each ^R5 and ^R6 is attached to each of the first and second adjacent carbons and can ^form , together with the carbon atoms to which they are attached, a 3 to ⁷ membered ring containing ring members selected from carbon atoms and up to 3 heteroatoms, the heteroatoms being independently selected from one oxygen atom, one sulfur atom and up to 3 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O) ₂ , and the ring is unsubstituted or substituted with at least one ^Rx .

Embodiment 8: A compound of formula 1 as described in any one of Embodiments 1, 1f-1g and 3-6f, wherein R ⁷ is H, C(O)R ¹⁵ or S(O) ₂ R ¹⁵ or Q ^b ; or C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, which is unsubstituted or substituted by at least one R ^x .

Embodiment 8a: A compound of formula 1 as described in any one of Embodiments 1, 1f-1g, 3-6f and 8, wherein ^R7 is _C1 - _C6 alkyl, _C1 - _C6 alkoxy, _C3 - _C6 cycloalkyl, _C2 - _C6 alkenyl or _C2 - _C6 alkynyl, which is unsubstituted or substituted by at least one ^Rx .

Embodiment 8b: The compound of formula 1 as described in any one of Embodiments 1, 1f-1g, 3-6f and 8, wherein R ⁷ is H, C ₁ -C ₆ alkyl, C(O)R ¹⁵ or S(O) ₂ R ¹⁵ or Q ^b .

Embodiment 8c: The compound of formula 1 as described in Embodiment 8b, wherein R ⁷ is H, C ₁ -C ₆ alkyl, C(O)R ¹⁵ or S(O) ₂ R ¹⁵ .

Embodiment 8d: The compound of formula 1 as described in Embodiment 8c, wherein R ⁷ is H or S(O) ₂ R ¹⁵ .

Embodiment 8e: The compound of formula 1 as described in Embodiment 8b, wherein R ⁷ is H, C ₁ -C ₆ alkyl or C(O)R ¹⁵ .

Embodiment 8f: The compound of formula 1 as described in embodiment 8e, wherein R ⁷ is H or C ₁ -C ₆ alkyl.

Embodiment 8g: The compound of formula 1 as described in embodiment 8f, wherein R ⁷ is H.

Embodiment 8h: The compound of formula 1 as described in Embodiment 8f, wherein R ⁷ is C ₁ -C ₆ alkyl.

Embodiment 9: A compound of formula 1 as described in any one of Embodiments 2-8h, wherein R ⁸ is NR ¹⁰ R ¹¹ , OR ¹² , C(=NR ¹³ )R ¹⁴ , C(O)NR ¹⁰ R ¹¹ , C(O)R ¹⁴ or S(O) _n R ¹⁴ ; or phenyl, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, each of which is unsubstituted or substituted by at least one R ^x .

Embodiment 9a: The compound of formula 1 as described in any one of embodiments 2 to 9, wherein R ⁸ is NR ¹⁰ R ¹¹ , OR ¹² , C(=NR ¹³ )R ¹⁴ , C(O)NR ¹⁰ R ¹¹ , C(O)R ¹⁴ or S(O) _n R ¹⁴ .

Embodiment 9b: The compound of formula 1 as described in any one of embodiments 2-9, wherein R ⁸ is phenyl, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, each of which is unsubstituted or substituted with at least one R ^x .

Embodiment 9c: The compound of formula 1 as described in Embodiment 9b, wherein R ⁸ is phenyl, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl.

Embodiment 9d: The compound of formula 1 as described in Embodiment 9a, wherein R ⁸ is OR ¹² .

Embodiment 9e: The compound of formula 1 as described in Embodiment 9d, wherein R ¹² is C ₁ -C ₄ alkyl.

Embodiment 10: The compound of formula 1 as described in any of the preceding embodiments, wherein n is 0, 1 or 2.

Embodiment 11: The compound of formula 1 as described in any of the preceding embodiments, wherein m is 0, 1, 2 or 3.

Embodiment 11a: A compound of formula 1 as described in any of the preceding embodiments, wherein m is 0, 1 or 2.

Embodiment 11b: A compound of formula 1 as described in any of the preceding embodiments, wherein m is 1 or 2.

Embodiment 11c: The compound of formula 1 as described in any of the preceding embodiments, wherein m is 1.

Embodiment X. A method for controlling and combating an invertebrate pest, the method comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound having Formula 1 .

Implementation X1. The method of Implementation X, wherein the invertebrate pest is a member of the order Hemiptera.

Implementation method X2. The method as described in implementation method X1, wherein the member of the Hemiptera is a member of the Homoptera.

Embodiment X2a. The method according to embodiment X2, wherein the Homoptera includes planthoppers from the families Cicadellidae and Delphacidae.

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

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

Implementation method X3. The method as described in implementation method X2, wherein the Homoptera includes CPH, GPA, CMA, BPH and WF.

Embodiment X4. The method according to embodiment X2, wherein the Homoptera includes Aphis fabae Scopoli (black bean aphid), Aphis gossypii Glover (cotton aphid or melon aphid), Bemisia tabaci Gennadius (tobacco whitefly, sweet potato whitefly), Bemisia argentifolii Bellows & Perring (silverleaf whitefly), Dialeurodes citri Ashmead (citrus whitefly) and Trialeurodes vaporariorum Westwood (greenhouse whitefly); Empoasca fabae Harris (potato leaf worm), and Empoasca spp. leafhopper), Laodelphax striatellus Fallen (smaller brown planthopper), Macrosteles quadrilineatus Forbes (aster leafhopper), Myzus persicae (Sulzer), Nephotettix cincticeps Uhler (green rice leafhopper), Nephotettix nigropictus Stål (rice leafhopper), Nilaparvata lugens Stål (brown planthopper), Peregrinus maidis Ashmead (corn planthopper), Sogatella furcifera Horvath (white-backed planthopper), Tagosodes orizicolus Muir (rice fly) delphacid), Typhlocyba pomaria McAtee (white apple leafhopper), or Erythroneura spp. (grape leafhoppers).

Implementation X5. The method as described in Implementation X1, wherein the Hemiptera is a member of the Heteroptera.

Embodiment X5a. The method as described in Embodiment X5, wherein the Heteroptera includes Acrosternum hilare Say (green stink bug), Anasa tristis De Geer (squash bug), Blissus leucopterus leucopterus Say (chinch bug), Cimex lectularius Llinnaeus (bedbug), Corythucha gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), Dichelops melacanthus Dallas (green belly stink bug), Dysdercus suturellus (black-winged stink bug), and Dichelops melacanthus Dallas (green belly stink bug). Herrich-Schäffer (cotton stainer), Euschistus heros Fabricius (Neotropical Brown Stink Bug), Euschistus servus Say (brown stink bug), Euschistus variolarius Palisot de Beauvois (one-spotted stink bug), Graptostethus spp. (complex of seed bugs), Halyomorpha halys Stål (brown marmorated stink bug), Leptoglossus corculus Say (leaf-footed pine seed bug), Lygus lineolaris Palisot de Beauvois (tarnished plant bug) bug), Nezara viridula Linnaeus (southern green stink bug), Oebalus pugnax Fabricius (rice stink bug), Oncopeltus fasciatus Dallas (large milkweed bug), Pseudatomoscelis seriatus Reuter (cotton fleahopper).

Implementation X6. The method of Implementation X5, wherein the Heteroptera includes stink bugs from the family Pentatomidae.

Implementation method X7. The method as described in implementation method X6, wherein the Heteroptera includes Euschistus servus Say (green rice stink bug), Euschistus servus Say (green-bellied stink bug), Euschistus variolarius Palisot de Beauvois (brown stink bug), Halyomorpha halys Stål (brown marmorated stink bug), Euschistus variolarius Stål (southern green stink bug), and Euschistus variolarius Palisot de Beauvois (rice stink bug).

Embodiment X8. The method as described in Embodiment X5, wherein the Heteroptera includes pumpkin bugs, chinch bugs, bed bugs, Corythuca gossypii Fabricius (cotton lace bugs), tomato bugs, Dysdercus suturellus Herrich-Schaffer (cotton bugs), Graptosthetus spp. (bear bug complex), leaf-footed pine seed bugs, ... bug), milkweed bug (Mesutomoscelis seriatus Reuter), or cotton fleahopper (Pseudatomoscelis seriatus Reuter).

The embodiments of the present disclosure (including the above-mentioned embodiments 1-X8 and any other embodiments described herein) can be combined in any manner, and the description of the variables in the embodiments not only relates to compounds having Formula 1 , but also relates to starting compounds and intermediate compounds useful for preparing compounds having Formula 1. In addition, the embodiments of the present disclosure (including the above-mentioned embodiments 1-X8 and any other embodiments described herein) and any combination thereof relate to the compositions and methods of the present disclosure.

The combination of implementation 1-X8 is illustrated by the following implementation:

Embodiment A1. A compound of formula 1 , wherein L is CR ⁵ R ⁶ , CR ⁵ R ⁶ CR ⁵ R ⁶ , OCR ⁵ R ⁶ or CR ⁵ R ⁶ O; CR ⁵ R ⁶ NR ⁷ , NR ⁷ CR ^{5 R 6 ,} C(=E)NR ⁷ , NR ⁷ C(=E), C(=E) CR ⁵ R ⁶ , CR ⁵ R ⁶ C(=E), C(=CR ⁵ R ⁶ ), CR ⁵ =CR ⁶ or C(=E); E is O or S; n is 0, 1, or 2; m is 1, 2, or 3; R ¹ is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ cycloalkoxy, which is unsubstituted or substituted by at least one R ^x ; or MQ ^a ; R ² is hydrogen, halogen, cyano, nitro or hydroxyl; or C ₁ -C ₆ alkyl; R ³ is hydrogen, halogen, cyano, nitro or hydroxyl; or C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl; R ⁴ is hydrogen, halogen, cyano, nitro, hydroxyl, SF ₅ , C(O)NH ₂ , C(O)NR ¹⁰ R ¹¹ , C(═NR ¹³ )NR ¹⁰ R ¹¹ , C(═NR ¹³ )R ¹⁴ , OC(O)R ¹⁴ , NR ¹⁰ R ¹¹ , NR ¹³ C(O)R ¹⁴ , C(O)R ¹⁴ , S(O) _n R ^R14 , OS(O) _nR14 , Si( ^R14 ) ₃ , OSi( ^R14 ) ₃ or ^MQa ; or _C1 - _C6 alkyl ^{; R5} and ^R6 are independently hydrogen, hydroxyl, halogen, cyano, _C1 - _C6 alkyl, _C3 - _C6 cycloalkyl, _C1 - _C6 halogenated alkyl, _C1 - _C6 alkoxy, _C1 -C6 halogenated alkoxy, _C3 - _C6 cycloalkoxy, _C1 - _C6 alkylthio or _C1 - _C6 halogenated alkylthio; ^R7 is H, C(O) ^R15 or S ⁽ O) ^2R15 or _Qb ; or _C1 - _C6 alkyl, _C1 - _C6 alkoxy, _C3 - _C6 cycloalkyl, _C2 - _C R ⁸ is NR ¹⁰ R ¹¹ , OR ¹² , C(═NR ¹³ )R 14 , C(O)NR 10 R 11 , C(O)R ¹⁴ or S(O) _n R ¹⁴ ; or _phenyl , C ₁ ^-C ₆ alkyl, C _{3 -C} ⁶ cycloalkyl, C ₂ -C ⁶ alkenyl or C _{2 -C 6} alkynyl, _each of which is unsubstituted or substituted _by at ^least one R ^x .

Embodiment A2. A compound of formula 1 , wherein L is CR ⁵ R ⁶ , OCR ⁵ R ⁶ or CR ⁵ R ⁶ O; C(=E)NR ⁷ , NR ⁷ C(=E) or C(=E); E is O or S; n is 0, 1, or 2; m is 1, 2, or 3; R ¹ is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ cycloalkoxy, which is unsubstituted or substituted with at least one R ^x ; or MQ ^a ; R ² is hydrogen, halogen, cyano, nitro or hydroxyl; or C ₁ -C ₆ alkyl; R ³ is hydrogen, halogen, cyano, nitro or hydroxyl; or C ₁ -C 6 R ⁴ is _hydrogen , halogen, cyano, nitro, hydroxyl, SF ₅ , C(O ₎ NH ₂ , C(O)NR ¹⁰ R ¹¹ _, C(═NR 13 )NR 10 R ¹¹ , C(═NR ¹³ )R ¹⁴ , OC(O)R ¹⁴ , NR ^{10 R 11 ,} NR ¹³ C(O)R ^{14 ,} C(O)R ¹⁴ , S(O) _n R ¹⁴ , OS(O) _n R ¹⁴ , Si(R ¹⁴ ) ₃ , OSi(R ¹⁴ ) ₃ or MQ ^a ; or C ₁ ^-C ₆ alkyl; R ⁵ and R ⁶ are independently hydrogen, hydroxyl, halogen, cyano, C ₁ -C ₆ alkyl, C _{3 -C 6} cycloalkyl; _R7 is H, C(O)R15, S( _O ^{) 2R15} , or ^Qb ; or _C1 - _C6 alkyl, _{C1 - C6} alkoxy, _{C3 - C6} cycloalkyl, _{C2 - C6} alkenyl, or _C2 - _C6 alkynyl _, which is unsubstituted or substituted _by at least one ^Rx ; and ^R8 is ^{NR10R11 ,} _OR12 ^, C(= _{NR13 )} ^R14 , C( _O ) _NR10R11 , C( _O ) _R15 ^{, or Qb ; 14} or S(O) _n R ¹⁴ ; or phenyl, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, each of which is unsubstituted or substituted by at least one R ^x .

Embodiment A3. The compound of formula 1 as described in Embodiment 1A, wherein L is ^{CR5R6 , OCR5R6} or ^CR5R6O ; C(=E) ^NR7 , ^NR7C (=E) or C(=E); E is O; n is 0, 1, or 2; m is 1 ^, 2, or 3; ^R2 is hydrogen, halogen ^, cyano, nitro or hydroxyl; or _C1 - _C6 alkyl; ^R3 is hydrogen, halogen, cyano, nitro or hydroxyl; or _C1 - _C6 alkyl, _C3 - _C6 cycloalkyl; ^R4 is hydrogen, halogen; or _C1 - _C6 alkyl; ^R5 and ^R6 are independently hydrogen, hydroxyl, halogen, cyano, _C1 - _C6 alkyl, C3- _C6 cycloalkyl; _R7 is H, C ₍ O) _R15 , S(O ^{) 2R15} , or _Qb ; or _C1 - _C6 alkyl, _C1 - _C6 alkoxy, _C3 - _C6 cycloalkyl, _{C2 - C6} alkenyl, or _C2 - _{C6 alkynyl} , which is unsubstituted or substituted _by at least one ^Rx ; and ^R8 is _NR10R11 ^{, OR12, C(=NR13)R14 , C (} _{O )} ^NR10R11 _{, C} ( _O ) _R14 ^{, or S} ( _O ^{) n} R ¹⁴ ; or phenyl, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, each of which is unsubstituted or substituted by at least one R ^x .

Embodiment A4. ^A compound of formula I as described in Embodiment 1A, wherein L is ^{CR5R6 , OCR5R6} or ^CR5R6O ; ⁿ is 0, 1, or 2; m is 1, 2, or 3; ^R1 is _C1 - _C6 alkyl, _C2 - _C6 alkenyl, _C2 - _C6 alkynyl, _C3 - _C6 cycloalkyl, _C1 - _C6 alkoxy, _C3 - _C6 cycloalkoxy, which is unsubstituted or substituted with at least one ^Rx ; ^R2 is hydrogen, halogen, cyano, nitro or hydroxyl; or _C1 - _C6 alkyl; ^R3 is hydrogen, halogen, cyano, nitro or hydroxyl; or _C1 - _C6 alkyl, _{C3-C6 cycloalkyl} ; R ^R4 is hydrogen, halogen, cyano, nitro, hydroxyl, _SF5 , C(O)NH2, C(O) _NR10R11 , C(= ^NR13 ) ^NR10R11 , C(= ^NR13 ) ^{R14 ,} OC(O) ^R14 , ^NR10R11 , ^{NR13C (} O) ^R14 , C(O) ^R14 , S(O) ^nR14 , OS(O) ^nR14 , Si ₍ ^R14 ) ₃ , OSi( ^R14 ) ³ _, or ^MQa _; or _C1 - _C6 alkyl; ^R5 and ^R6 are independently hydrogen ^, hydroxyl, halogen, cyano, _C1 - _C6 alkyl, _C3 - _C6 cycloalkyl, _C1 -C ^R is ^NR10R11 , OR12, C(= _{NR13 ) R14} , C(O)NR10R11, ^C _{(O ) R14} or S(O) ^nR14 ; or phenyl, _C1 - _C6 ^alkyl , _C3 - _{C6 cycloalkyl} , _{C2 - C6} ^alkenyl or _{C2 -} ^C6 _alkynyl , _each of ^which is unsubstituted or _substituted ^by at least ^one _Rx ^.

Embodiment A5. The compound of formula I as described in Embodiment A1, wherein L is C(=E) ^NR7 , ^NR7C (=E) or C(=E); E is O or S; n is 0, 1, or 2; m is 1, 2, or 3; ^R1 is _C1 - _C6 alkyl, _C2 - _C6 alkenyl, _C2 - _C6 alkynyl, _C3 - _C6 cycloalkyl, _C1 - _C6 alkoxy, C3 _{- C6} cycloalkoxy, which is unsubstituted or substituted with at least one ^Rx ; ^R2 is hydrogen, halogen, cyano, nitro or hydroxyl; or _C1 - _C6 alkyl; ^R3 is hydrogen, halogen, cyano, nitro or hydroxyl; or _C1 - _C6 alkyl, _C3 - _C6 cycloalkyl; ^R4 is hydrogen, halogen, cyano, nitro, hydroxyl, _SF5 , C(O)NH2, C(O) _NR10R11 , C(= ^NR13 ) ^NR10R11 , C(= ^NR13 ) ^{R14 ,} OC(O) ^R14 , ^NR10R11 , ^{NR13C (} O) ^R14 , C(O) ^R14 , S(O) ^nR14 , OS(O) ^nR14 , Si ₍ ^{R14 )} ₃ , OSi( ^R14 ) ³ _, or ^MQa _; or _C1 - _C6 alkyl; ^R7 is H, C(O) ^R15 , or S(O) _2R15 ^, or ^Qb ; or _C1 - _C6 alkyl, _C1 - _C6 alkoxy, _C3 -C R ⁸ is NR ¹⁰ R 11 , OR ¹² , C(═NR 13 ₎ R ₁₄ , C( ^{O)NR 10 R 11 , C(O)R 14 or S} (O) _n R ¹⁴ ; or phenyl, C _{1 -C 6} alkyl, C ³ _-C ⁶ cycloalkyl, C ₂ -C ⁶ alkenyl or C ² _{-C 6 alkynyl ,} each of _which is unsubstituted or substituted _by at least one R ^x .

Embodiment A6. The compound of formula I as described in Embodiment 1A, wherein L is CR ⁵ R ⁶ , OCR ⁵ R ⁶ or CR ⁵ R ⁶ O; n is 0, 1, or 2; m is 1; R ² is hydrogen, halogen, cyano, nitro or hydroxyl; or C ₁ -C ₆ alkyl; R ³ is hydrogen, halogen, cyano, nitro or hydroxyl; or C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl; R ⁴ is hydrogen, halogen, cyano, nitro, hydroxyl, SF ₅ , C(O)NH ₂ , C(O)NR ¹⁰ R ¹¹ , C(=NR ¹³ )NR ¹⁰ R ¹¹ , C(=NR ¹³ )R ¹⁴ , OC(O)R ¹⁴ , NR ¹⁰ R ¹¹ or C ¹ -C 6 alkyl; R ⁵ and R ⁶ are ^{independently} _hydrogen , hydroxyl _, halogen, cyano, C ^{1 -C 6} _alkyl , C 3 -C ₆ ^cycloalkyl , C ₁ -C ₆ halogenated alkyl, C 1 -C ₆ alkoxy, C ¹ -C ₆ halogenated alkoxy, C ₃ -C ₆ cycloalkoxy, C ₁ -C ₆ alkylthio or C _{1 -C 6 halogenated} alkylthio; and ^{R 8 is} NR ¹⁰ R ^{11 , OR} ₁₂ ^, C _{( ＝} NR _{13 )} ^R ₁₄ , C(O)NR ¹⁰ R ¹¹ , C(O)R ¹⁴ or S(O) _n R ¹⁴ ; or phenyl, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, each of which is unsubstituted or substituted by at least one R ^x .

Embodiment A7. A compound of formula I as described in Embodiment 1A, wherein L is C(=E) ^NR7 , ^NR7C (=E) or C(=E); E is O; n is 0, 1, or 2; m is 1; ^R1 is _C1 - _C6 alkyl, _C2 - _C6 alkenyl, _C2 - _C6 alkynyl, _C3 - _C6 cycloalkyl, _C1 - _C6 alkoxy, _C3 - _C6 cycloalkoxy, which is unsubstituted or substituted with at least one ^Rx ; ^R2 is hydrogen, halogen, cyano, nitro or hydroxyl; or _C1 - _C6 alkyl; ^R3 is hydrogen, halogen, cyano, nitro or hydroxyl; or _C1 - _C6 alkyl, _C3 - _C6 cycloalkyl; ^R4 is hydrogen, halogen, cyano, nitro, hydroxyl, _SF5 , C(O)NH2, C(O) _NR10R11 , C(= ^NR13 ) ^NR10R11 , C(= ^NR13 ) ^{R14 ,} OC(O) ^R14 , ^NR10R11 , ^{NR13C (} O) ^R14 , C(O) ^R14 , S(O) ^nR14 , OS(O) ^nR14 , Si ₍ ^{R14 )} ₃ , OSi( ^R14 ) ³ _, or ^MQa _; or _C1 - _C6 alkyl; ^R7 is H, C(O) ^R15 , or S(O) _2R15 ^, or ^Qb ; or _C1 - _C6 alkyl, _C1 - _C6 alkoxy, _C3 -C R ⁸ is NR ¹⁰ R 11 , OR ¹² , C(═NR 13 ₎ R ₁₄ , C( ^{O)NR 10 R 11 , C(O)R 14 or S} (O) _n R ¹⁴ ; _or phenyl, C _{1 -C 6} alkyl, C ³ -C ⁶ cycloalkyl, C ₂ -C ⁶ alkenyl or C ² _{-C 6 alkynyl ,} each of _which is unsubstituted or substituted _by at least one R ^x .

Embodiment A8. A compound of formula 1 , wherein L is ^CR5R6 , ^CR5R6CR5R6 , ^{OCR5R6 or CR5R6O} ; C(= ^{E ) NR7 , NR7C} (=E ⁾ or C(=E); E is O; ^R1 is S(O) ^nR14 ; or _C1 -C6 alkyl, C2- _C6 alkenyl, _C2 - _{C6 alkynyl} , ^C3 - _C6 cycloalkyl, _C1 - _C6 alkoxy, _C3 - _C6 cycloalkoxy, which is unsubstituted or substituted _{with at least one Rx; R2 is hydrogen; R3 is C1-C6} ^{alkyl ; R4} _{is hydrogen ;} ^{R5 and R6} are independently hydrogen _, hydroxyl, halogen, cyano, _C1 -C6 _R7 is H, C( _O ) _R15 , S(O) ^2R15 , or Qb; or _C1 - _C6 alkyl, _{C1 - C6} alkoxy, _{C3 - C6} cycloalkyl, _{C2 - C6} alkenyl, or _C2 - _C6 alkynyl, which is unsubstituted or substituted _by at least ^{one Rx} ; ^R8 is ^{NR10R11 ,} _OR12 , C _{( = NR13 )} ^{R14 ,} C( _O ⁾ _NR10R11 , C ₍ O) _R15 ^{, or Qb ; 14} or S(O) _n R ¹⁴ ; or phenyl, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, each of which is unsubstituted or substituted with at least one R ^x ; n is 0, 1, or 2; and m is 1.

Embodiment A9. A compound of formula 1 , wherein L is ^CR5R6 , ^CR5R6CR5R6 , ^{OCR5R6 or CR5R6O} ; C(= ^{E ) NR7 , NR7C} (=E) or C(=E); E is O; ^R1 is S(O) ^nR14 ; ^or _C1 - _C6 alkyl or _C1 - _{C6 alkoxy} , which is unsubstituted or substituted ^with at least one ^Rx ; ^R2 is hydrogen; ^R3 is _C1 - _C6 alkyl; ^R4 is hydrogen; ^R5 and ^R6 are independently hydrogen, hydroxyl, halogen, cyano, _C1 - _C6 alkyl, _C3 -C6 cycloalkyl, _C1 - _C6 haloalkyl, _{C1 -C6 alkoxy} , _C1 -C6 R ₇ is H, C(O)R ¹⁵ , S(O) ₂ R ¹⁵ , or Q ^b ; or C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, or C _{2 -C 6} alkynyl, which is unsubstituted or substituted by at least one R ^x ; R ⁸ is NR ¹⁰ R ¹¹ , OR ₁₂ , C( _{═NR 13} )R ₁₄ , C ₍ ^O )NR ¹⁰ R ¹¹ , C(O)R ¹⁴ , or S(O) _n R ¹⁴ ; or phenyl, C 1 ^{-C 6 alkyl} , C ₃ -C ⁶ cycloalkyl, C ₂ -C ₆ alkenyl, or C ₂ -C ₆ alkynyl. R x is a C ₂ -C ₆ alkenyl or C 2 -C ₆ alkynyl group, each of which is unsubstituted or substituted with at least one R ^x ; n is 0, 1, or 2; and m is 1.

Specific embodiments include compounds having Formula 1 selected from the group consisting of compounds described in Table 1. [ Table 1 ] Compound (Cmp) Structure Chemical ^name1,2 1 N-(7-methyl[1,2,4]triazolo[1,5-a]pyridin-5-yl)-4-(trifluoromethyl) ^benzamide 2 7-Methyl-5-[[4-(trifluoromethyl)phenyl]methoxy][1,2,4]triazolo[1,5-a]pyridine ² 3 7-Methyl-5-((4-(trifluoromethoxy)benzyl)oxy)-[1,2,4]triazolo[1,5-a]pyridine ¹ 4 7-Methyl-5-((4-((trifluoromethyl)thio)benzyl)oxy)-[1,2,4]triazolo[1,5-a]pyridine ¹ 5 7-Methyl-5-((4-((trifluoromethyl)sulfinyl)benzyl)oxy)-[1,2,4]triazolo[1,5-a]pyridine ¹ 6 7-Methyl-5-((4-((trifluoromethyl)sulfonyl)benzyl)oxy)-[1,2,4]triazolo[1,5-a]pyridine 7 (7-methyl[1,2,4]triazolo[1,5-a]pyridin-5-yl)[4-(trifluoromethoxy)phenyl]methanone 8 5-[Fluoro[4-(trifluoromethoxy)phenyl]methyl]-7-methyl[1,2,4]triazolo[1,5-a]pyridine 2 9 5-[Methoxy[4-(trifluoromethoxy)phenyl]methyl]-7-methyl[1,2,4]triazolo[1,5-a]pyridine 2 10 7-Methyl-5-[[4-(trifluoromethoxy)phenyl]methyl][1,2,4]triazolo[1,5-a]pyridine 2 11 (7-methyl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)(4-(trifluoromethoxy)phenyl)methanone ¹ 12 7-Methyl-5-[[4-(trifluoromethyl)phenyl]methyl][1,2,4]triazolo[1,5-a]pyridine ² 13 5-(Methoxy(4-(trifluoromethyl)phenyl)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine ¹ 14 5-[Fluoro[4-(trifluoromethyl)phenyl]methyl]-7-methyl[1,2,4]triazolo[1,5-a]pyridine ² 15 (7-methyl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)(4-(trifluoromethoxy)phenyl)methanol ¹ 19 (6-cyclopropyl-3aH-inden-4-yl)(4-(trifluoromethoxy)phenyl)methanone ¹ 48 5-(Fluoro(4-(trifluoromethyl)phenyl)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine ¹ 49 5-(3-Fluoro-4-(trifluoromethyl)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine ¹ 52 5-(3-Fluoro-4-(trifluoromethoxy)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine ¹ 53 5-(Fluoro(3-fluoro-4-(trifluoromethoxy)phenyl)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine ¹ 79 1-(7-cyclopropyl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-1-(4-(trifluoromethoxy)phenyl)ethan-1-ol ¹ 33 5-(Fluoro(4-(trifluoromethoxy)phenyl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-a]pyridine ¹ 82 5-(2-Fluoro-4-(trifluoromethyl)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine ¹ 84 5-((2-fluoro-4-(trifluoromethoxy)phenyl)(methoxy)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine ¹ 86 5-(Fluoro(2-fluoro-4-(trifluoromethoxy)phenyl)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine ¹ 141 7-iodo-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine ¹ 159 7-Isopropyl-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine ¹ 160 7-(Difluoromethyl)-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine ¹ 103 7-Cyclopropyl-5-(4-(trifluoromethyl)benzyl)-[1,2,4]triazolo[1,5-a]pyridine ¹ 83 5-(2-Fluoro-4-(trifluoromethoxy)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine ¹ 128 7-Bromo-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine ¹ 130 7-Cyclopropyl-6-(2-(3-(trifluoromethyl)phenyl)cyclopropyl)-[1,2,4]triazolo[1,5-a]pyridine ¹ 226 7-Cyclopropyl-5-((3-fluoro-4-(trifluoromethyl)phenyl)(methoxy)methyl)-[1,2,4]triazolo[1,5-a]pyridine ¹ 221 7-Cyclopropyl-5-(fluoro(3-fluoro-4-(trifluoromethoxy)phenyl)methyl)-[1,2,4]triazolo[1,5-a]pyridine ¹ twenty one 7-Cyclopropyl-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine ¹ 18 7-Cyclopropyl-5-(fluoro(4-(trifluoromethoxy)phenyl)methyl)-[1,2,4]triazolo[1,5-a]pyridine ^{1 1Chemical} name automatically generated by ChemDraw Professional, Version 17.0. ^2CAS name. And any combination of the above.

More specific implementation methods include: A compound selected from the group consisting of: N-(7-methyl[1,2,4]triazolo[1,5-a]pyridin-5-yl)-4-(trifluoromethyl)benzamide, 7-methyl-5-[[4-(trifluoromethyl)phenyl]methoxy][1,2,4]triazolo[1,5-a]pyridine, (7-methyl[1,2,4]triazolo[1,5-a]pyridin-5-yl)[4-(trifluoromethoxy)phenyl]methanone, 5-[fluoro[4-(trifluoromethoxy)phenyl]methyl]-7-methyl[1,2,4]triazolo[1,5-a]pyridine, 5-[methoxy[4-(trifluoromethoxy)phenyl]methyl]-7-methyl[1,2,4]triazolo[1,5-a]pyridine, 7-methyl-5-[[4-(trifluoromethoxy)phenyl]methyl][1,2,4]triazolo[1,5-a]pyridine, 7-methyl-5-[[4-(trifluoromethyl)phenyl]methyl][1,2,4]triazolo[1,5-a]pyridine, 5-[fluoro[4-(trifluoromethyl)phenyl]methyl]-7-methyl[1,2,4]triazolo[1,5-a]pyridine, (6-cyclopropyl-3aH-inden-4-yl)(4-(trifluoromethoxy)phenyl)methanone, 5-(fluoro(4-(trifluoromethyl)phenyl)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-(3-fluoro-4-(trifluoromethyl)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-(3-fluoro-4-(trifluoromethoxy)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-(fluoro(3-fluoro-4-(trifluoromethoxy)phenyl)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 1-(7-cyclopropyl-[1,2,4]triazolo[1,5-a]pyridine-5-yl)-1-(4-(trifluoromethoxy)phenyl)ethan-1-ol, 5-(fluoro(4-(trifluoromethoxy)phenyl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-a]pyridine, 5-(2-fluoro-4-(trifluoromethyl)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-((2-fluoro-4-(trifluoromethoxy)phenyl)(methoxy)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-(fluoro(2-fluoro-4-(trifluoromethoxy)phenyl)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 7-iodo-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-isopropyl-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-(difluoromethyl)-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-cyclopropyl-5-(4-(trifluoromethyl)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 5-(2-fluoro-4-(trifluoromethoxy)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 7-bromo-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-cyclopropyl-6-(2-(3-(trifluoromethyl)phenyl)cyclopropyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-cyclopropyl-5-((3-fluoro-4-(trifluoromethyl)phenyl)(methoxy)methyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-cyclopropyl-5-(fluoro(3-fluoro-4-(trifluoromethoxy)phenyl)methyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-cyclopropyl-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, and 7-cyclopropyl-5-(fluoro(4-(trifluoromethoxy)phenyl)methyl)-[1,2,4]triazolo[1,5-a]pyridine, and any combination of the foregoing compounds.

Embodiment Y1. A composition comprising a compound of formula 1 as described in any of the preceding embodiments and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent, wherein the composition further comprises at least one additional biologically active compound or agent as needed.

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

Embodiment Y2. The composition of embodiment Y1 or Y1', wherein the at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acetothiocarb, cypermethrin, acetamiprid, acetamiprid, fluazifop, sulfamethoxam, amitraz, avermectin, azadirachtin, azoxystrobin, chlorpyrifos, propylthiocarb, chlorpyrifos, bifenthrin, bifenazate, diflunisal, borate, bromobendan, phenthiocarb, carbaryl, chlorpyrifos, chlorpyrifos, chloranil, d-trans-chlorpropthrin, chlorpyrifos , methyl chlorpyrifos, cyclohexidine, tetramid, clothianidin, bromocyanamide, cyclobromocyanamide, triflupyramide, cypermethrin, epoxyfenoxam, ethomid, butyric acid, flucythrin, high-efficiency flucythrin, chlorflucythrinate ... High-efficiency chlorflucythrinate, cypermethrin, cis-cypermethrin, ζ-cypermethrin, cyprofenamide, cypermethrin, cypermethrin, difenac, dichlorvos, dichlorobenzamide, dieldrin, fluazifop, dimethoate, tetrafluthrin, cypermethrin, dimethoate, dimethoate, dimethoate, fenpropimorph, fenpropimorph, Masamectin, endosulfan, cypermethrin, ethoprolin, ethomethrin, ethidazole, quinamoxadone, fenbutin, cypermethrin, bisthiocarb, fenoxycarb, cyfluthrin, cypermethrin, flumethrin, fluazifop, flumetol, flumetol, flufenamid, flumetol, flumetol Amine, fluchloramid, flucythrinate, flumethrin, flufenamid, flutolan, fluopyram, flufenamid, flupyrad, flupyrad, fluvalinate, fluvalinate, flutolan, flutolan, flutothion, flutothion, flutoxan, flutothion, flutothion, flutothion, flutothion, flutothion, flutothion, flutothion Cypermethrin, fluazifop, thiophanate-methyl, thiophenesulfuron, fluazifop, chloranil, pyraclostrobin, indazole (N-(1-methylcyclopropyl)-2-(3-pyridyl)-2H-indazole-4-carboxamide), indomethacin, insecticide soap, isopropylamidophos, isothiocarb, κ-tefluthrin, methoprene, cyfluthrin, marasmustine, cyfluthrin, cyfluthrin, metaldehyde, methamidophos, chlorpyrifos, methiocarb, cyfluthrin, methoprene, methoxychlor, methoxychlor, chloranil, chloranil, monocrotophos, monofluthrin, cyfluthrin, niacin, N -[1,1-dimethyl-2-(methylthio)ethyl]-7-fluoro-2-(3-pyridyl) -2H -indazole-4-carboxamide, N -[1,1-dimethyl-2-(methylsulfinyl)ethyl]-7-fluoro-2-(3-pyridyl) -2H -indazole-4-carboxamide, N -[1,1-dimethyl-2-(methylsulfonyl)ethyl]-7-fluoro-2-(3-pyridyl) -2H -indazole-4-carboxamide, N-(1-methylcyclopropyl)-2-(3-pyridyl)-2H-indazole-4-carboxamide, N -[1-(difluoromethyl)cyclopropyl]-2-(3-pyridyl) -2H -Indazole-4-carboxamide, nitenpyram, nitrobenzene, fluazifop, noviflumuron, cypermethrin, chlorpyrifos, parathion, methyl parathion, permethrin, phorate, phosphamidon, phosmet, pirimicarb, profenofos, profluthrin, cyfluthrin, pyrifos, pymetrozine, pyrifos Afenamide, pyrethrin (pyrethrin), cypermethrin, pyraclostrobin, pyrimethamine, pyraclostrobin, pyriproxyfen, rotenone, ryanodine, flucythrinate, dispirothrin, ethyl styracidin, styracidin, spirothiazolin, spirothiazolin, spiromethoxazole ... Hydrazide, pyraclostrobin, flubendiamide, tefluthrin, κ-tefluthrin, terbufos, tetrachlorvinphos, cypermethrin, tetrafluthrin, tetrazolam, thiamethoxam, thiocarb, cypermethrin, thiocarb, sulfamethoxam, thiocarb, thiosulfuron, cypermethrin, tetracycline, tralomethrin, trichlorfon, trifloxystrobin, trifloxystrobin Cyclomethicone, trifluanid, cypermethrin, chlorpyrifos, Bacillus sphaericus, Bacillus thuringiensis delta-endotoxin, insect pathogenic bacteria, insect pathogenic viruses and insect pathogenic fungi, plant essences including synthetic extracts and unrefined oils, RNA interference-mediated target inhibitors, thiocarbamide, and trifluanid.

Embodiment Y3. The composition of embodiment Y2, wherein the at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acetamiprid, flumethrin, cypermethrin, amitraz, avermectin, azadirachtin, propylthiocarb, chlorpyrifos, bifenthrin, phenthiocarb, carbaryl, chlorpyrifos, chloranil, chlorpyrifos, clothianidin, cyanamide, cyclamoxadone, cypermethrin, fluchlorinated Cypermethrin, high-efficiency cyfluthrin, cyfluthrin, high-efficiency cyfluthrin, high-efficiency cyfluthrin, cypermethrin, cis-cypermethrin, ζ-cypermethrin, mefenamic acid, deltamethrin, dieldrin, furothiocarb, benzylchlorfen, imamitrin, endosulfan, cypermethrin, ethoprolin, ethomethrin, ethomethin, cyfluthrin, fenthiocarb, fenoxycarb, cypermethrin, flumethrin, flufenamic acid, flumetol ... Fenpyraclostrobin, flufenacet, flupiprole, flupyralidone, fluvalinate, flumethrin, thiamethoxam, tefluthrin, flufenamide, fluazifop, pyrimidine, indocarb, lufenuron, cyfluthrin, cyfluthrin, methiocarb, methomyl, methoprene, methoxyfenopyr, metoclopramide, monofluthrin, nitenpyram, nitrobenzene, fluazifop, flufenamide, pymetrozine, pyrethroid chlorpyrifos, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil, chloranil

Embodiment Y4. The composition as described in any one of Embodiments Y1-Y3, further comprising liquid fertilizer.

Implementation method Y5. A composition as described in implementation method Y4, wherein the liquid fertilizer is water-based.

Embodiment Y6. A soil soak preparation, comprising the composition as described in any one of Embodiments Y1-Y3.

Embodiment Y7. A spray composition comprising the composition as described in any one of Embodiments Y1-Y3 and a propellant.

Embodiment Y8. A feed composition comprising the composition as described in any one of Embodiments Y1-Y3, one or more food materials, an attractant as needed, and a wetting agent as needed.

Embodiment Y9. A trapping device for controlling invertebrate pests, the trapping device comprising: a bait composition as described in embodiment Y8 and a shell adapted to accommodate the bait composition, wherein the shell has at least one opening, the size of the opening is set to allow invertebrate pests to pass through the opening, so that the invertebrate pests can approach the bait composition from a position outside the shell, and wherein the shell is further adapted to be placed in or near a location where the invertebrate pests may or are known to move.

Embodiment Y10. A composition comprising the composition as described in any one of Embodiments Y1-Y3, wherein the composition is a solid composition selected from powders, powders, granules, spheres, granules, tablets, tablets and filled films.

Embodiment Y11. The composition as described in Embodiment Y10, wherein the composition is water-dispersible or water-soluble.

Embodiment Y12. A liquid or dry agent comprising a composition as described in any one of embodiments Y1-Y3, wherein the liquid or dry agent is used in a drip irrigation system, a trench during planting, a handheld sprayer, a backpack sprayer, a pole sprayer, a ground sprayer, air application, an unmanned aerial vehicle, or seed treatment.

Embodiment Y13. A liquid or dry formulation as described in Embodiment Y12, wherein the formulation is sprayed in ultra-low volume.

Notably, the compounds of the present disclosure are characterized by favorable metabolic patterns and/or soil retention patterns and exhibit activity against a broad spectrum of agricultural and non-agricultural invertebrate pests.

Of particular note is that, due to the control spectrum and economic importance of invertebrate pests, protecting crops from damage or injury caused by invertebrate pests by controlling and combating 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 in direct contact with the compound of Formula 1 or a composition comprising the compound due to their favorable transfer characteristics or systemicity in plants.

Also noteworthy as an embodiment of the present disclosure is a composition comprising a compound as described in any of the aforementioned embodiments and any other embodiments 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, wherein the composition optionally further comprises at least one additional biologically active compound or agent.

Also noteworthy as an embodiment of the present disclosure is a composition for controlling and combating invertebrate pests comprising a compound as described in any of the preceding embodiments and any other embodiments 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, the composition optionally further comprising at least one additional biologically active compound or agent. Embodiments of the present disclosure further include methods for controlling and combating invertebrate pests, the methods comprising contacting the invertebrate pests or their environment with a biologically effective amount of a compound as described in any of the preceding embodiments (e.g., as a composition described herein).

Embodiments of the present disclosure also include compositions in the form of soil soak liquid formulations comprising a compound as described in any of the preceding embodiments. Embodiments of the present disclosure further include methods for controlling and combating invertebrate pests, the methods comprising contacting soil with a liquid composition as a soil soak comprising a biologically effective amount of a compound as described in any of the preceding embodiments.

Embodiments of the present disclosure also include spray compositions for controlling and combating invertebrate pests, the spray compositions comprising a biologically effective amount of a compound as described in any of the preceding embodiments and a propellant. Embodiments of the present disclosure further include feed compositions for controlling and combating invertebrate pests, the feed compositions comprising a biologically effective amount of a compound as described in any of the preceding embodiments, one or more food materials, an attractant as needed, and a wetting agent as needed. Embodiments of the present disclosure also include a device for controlling and combating invertebrate pests, the device comprising the bait composition and a shell adapted to contain the bait composition, wherein the shell has at least one opening sized to allow invertebrate pests to pass through the opening, so that the invertebrate pests can access the bait composition from a location outside the shell, and wherein the shell is further adapted to be placed in or near a possible or known activity location of the invertebrate pests.

Embodiments of the present disclosure also include methods for protecting seeds from invertebrate pests, comprising contacting the seeds with a biologically effective amount of a compound as described in any of the preceding embodiments.

Embodiments of the present disclosure also include methods for protecting animals from invertebrate parasitic pests, comprising administering to the animal a parasiticidally effective amount of a compound as described in any of the preceding embodiments.

Embodiments of the present disclosure also include methods for controlling and combating invertebrate pests, which methods comprise 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), provided that the methods are not methods of medical treatment of the human or animal body by therapy.

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 having 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, wherein the composition optionally further comprises a biologically effective amount of at least one additional biologically active compound or agent, provided that such methods are not methods of medical treatment of the human or animal body by therapy.

One or more of the following methods and variations as described in Schemes 1-10 can be used to prepare compounds of Formula 1. Unless otherwise indicated, ^R1 , ^R2 , ^R3 , ^R4 , ^R5 , ^R6 , ^R7 , X, LG and m in the compounds of the following formulae are as defined in the disclosure above. Ambient temperature or room temperature is defined as about 20°C-25°C.

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

Triazole compounds of formula 1b (formula 1 wherein L is OCR ⁵ R ⁶ ) can be prepared by reacting a heterocyclic compound of formula 2a (wherein X is a halogen atom or a suitable ionizing group) with an alcohol of formula 3b in the presence of a base and in the presence or absence of a catalyst such as copper (I) iodide as shown in Scheme 2. Typical bases used include carbonates such as sodium carbonate or potassium carbonate, phosphates such as potassium triphosphate and amines such as triethylamine. Typical solvents include THF, dihydrogen sulfide, toluene, DMF, DMSO, acetonitrile or mixtures thereof. Typical reaction temperatures range from ambient temperature to the boiling point of the solvent. Scheme 2

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

The triazole compound of formula 1d (formula 1 wherein L is C(=O)) can be prepared by reacting a compound of formula 1c (wherein R ⁶ is a hydrogen atom) with an oxidant as shown in Scheme 4. Typical oxidants used include air, oxygen, t-BuO ₂ H, NaOCl, NBS, CrO ₃ , KMnO ₄ , DMSO/Ac ₂ O, Cl ₂ /pyridine. Typical solvents include water, THF, dioxane, toluene, DMF, DMSO, acetonitrile or mixtures thereof.

The oxidation step can be carried out over a wide range of temperatures, ranging from about -70°C to about 200°C. Of note are temperatures from about 20°C to about 100°C, which typically provide fast reaction times and high product yields. General methods and procedures for the oxidation of alcohols to form ketones are well known in the literature; see, for example, RC Larock, Comprehensive Organic Transformations, VCH, 1989 , New York City, NY. Scheme 4

Triazole compounds of Formula 1e (Formula 1 wherein L is ^CR5R6 and ^R5 is not OH) can be prepared by reacting compounds of Formula 1c with various reagents as shown in Scheme ^5. Typical solvents include water, THF, dihydrogen sulfide, toluene, DMF, DMSO, acetonitrile or mixtures thereof.

Such functional group transformations can be carried out over a wide range of temperatures, ranging from about -70°C to about 200°C. Of note are temperatures from about 0°C to about 100°C, which typically provide fast reaction times and high product yields. General methods and procedures for converting alcohols to other functional groups are well known in the literature; see, for example, RC Larock, Comprehensive Organic Transformations, VCH, 1989 , New York City, NY. Scheme 5

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

Triazole compounds of formula 2c (wherein LG is a detachable group, such as a halogen atom, a sulfonate group) can be prepared by reacting compounds of formula 2d (wherein R is typically an alkyl group) with SOCl ₂ , (COCl) 2 , POCl 3 , PCl 3 , PCl 5 and PPh 3 / BR ² (to install a halogen atom, see Yingyong Huaxue [Applied Chemistry], 1995 , 12(3), 82-84) or with MeSO ₂ Cl, TolSO ₂ Cl (to install a sulfonate group) in the presence of a base as shown in Scheme 7. Typical bases used include carbonates such as sodium carbonate or potassium carbonate, phosphates such as potassium triphosphate and organic bases such as triethylamine and pyridine. Typical solvents include DCM, THF, dihydrogen peroxide, toluene, DMF, DMSO, acetonitrile or mixtures thereof. Typical reaction temperatures range from ambient temperature to the boiling point of the solvent. Scheme 7

The triazole compound of formula 2d can be prepared by reacting a compound of formula 2e (wherein R is typically an alkyl group) with a metal hydride (such as LiAlH ₄ , NaBH ₄ , NaBH ₃ (CN)) (when R ⁵ or R ⁶ or both are hydrogen atoms) or a Grignard reagent as shown in Scheme 8. Typical solvents include DCM, THF, dihydrogen hydride, toluene, DMF, DMSO, acetonitrile, methanol or mixtures thereof. Typical reaction temperatures range from -70°C to the boiling point of the solvent. Scheme 8

Triazole compounds of formula 1g (formula 1 wherein L is CONR ⁷ ) can be prepared by reacting a heterocyclic compound of formula 2e (wherein R is typically a hydrogen atom or an alkyl group) with an amine of formula 3d as shown in Scheme 9. Typical solvents include THF, dihydrogen hydride, toluene, DMF, DMSO, acetonitrile or mixtures thereof. Typical reaction temperatures range from -70°C to the boiling point of the solvent. Scheme 9

The triazole compound of formula 2e can be prepared by catalytic carbonylation of a compound of formula 2a (wherein X is a suitable ionizing group such as a halogen) with carbon monoxide and an alcohol of formula 3e in the presence of a catalyst and a suitable ligand as shown in Scheme 10. The catalyst can be generated from a transition metal such as Pd (e.g., Pd(OAc) ₂ or Pd ₂ (dba) ₃ ) and a mono- or di-dentate ligand such as PPh ₃ , PCy ₃ , Pt-Bu ₃ , x-phos, xantphos, s-phos and dppf. Typical bases used include carbonates such as sodium carbonate or cesium carbonate, phosphates such as potassium triphosphate, amines such as ethyldiisopropylamine. Typical solvents include THF, dihydrogen hydride, toluene, ethanol, DMF or mixtures thereof. Typical reaction temperatures range from ambient temperature to the boiling point of the solvent. Scheme 10

It will be appreciated that some of the reagents and reaction conditions described above for preparing compounds of Formula 1 may not be compatible with certain functional groups present in the intermediates. In such cases, incorporating protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired product. The use and selection of protecting groups will be apparent to those skilled in the art of chemical synthesis (see, e.g., 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, following the introduction of a given reagent as described in any individual scheme, additional conventional synthetic steps not described in detail may be necessary to complete the synthesis of a compound of Formula 1 . Those skilled in the art will also recognize that it may be necessary to perform combinations of the steps shown in the above schemes in a different order than the specific sequence presented to prepare compounds of Formula 1 .

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

Without further elaboration, it is believed that one skilled in the art can utilize the present disclosure to its maximum extent using the foregoing description. Therefore, the following synthetic examples should be interpreted as being merely illustrative and not limiting the present disclosure in any way. The steps in the following synthetic examples illustrate the procedure for each step in the overall synthetic transformation, and the starting materials used in each step do not necessarily have to be prepared by specific preparative experiments whose procedures are described in other examples or steps. Ambient temperature or room temperature is defined as approximately 20°C-25°C. Percentages are by weight, except for chromatographic solvent mixtures or otherwise specified. Unless otherwise specified, the parts and percentages of chromatographic solvent mixtures are by volume. MPLC refers to medium pressure liquid chromatography on silica gel. ¹ H NMR spectra are reported in ppm downfield from tetramethylsilane; "s" means singlet, "d" means doublet, "dd" means doublet of doublet, "ddd" means doublet of doublet of doublet, "t" means triplet, "m" means multiplet, and "br s" means broad singlet. For mass spectral data, the values reported are the molecular weight of the parent molecular ion ( ^M ) formed by the addition of H ⁺ (molecular weight 1) to the molecule in order to obtain the M+1 peak observed by mass spectrometry using atmospheric pressure chemical ionization (AP + ).

Schemes 1 to 10 illustrate methods for preparing compounds of Formula 1 having a variety of substituents. Compounds of Formula 1 having substituents other than those specifically noted in Schemes 1 to 10 can be prepared by general methods known in the art of synthetic organic chemistry, including methods similar to those described in Schemes 1 to 10. Synthesis Example 1 Preparation of (7-methyl-[1,2,4]triazolo[1,5- a ]pyridin-5-yl)-[4-(trifluoromethoxy)phenyl]methanol) (Compound 15)

n-Butyl lithium (2.441 mL, 1.6 M in hexanes, 3.905 mmol) was added dropwise to a solution of 7-methyl-[1,2,4]triazolo[1,5- a ]pyridine (0.4 g, 3.004 mmol) in anhydrous tetrahydrofuran at -78°C. The reaction was stirred at -78°C for 30 min. Thereafter, 4-(trifluoromethoxy)benzaldehyde (0.742 g, 3.905 mmol) was added as a solution in anhydrous tetrahydrofuran over 3 min. The reaction mixture was stirred at -78°C for 15 min. The reaction was allowed to stir at 25°C for 45 min, then quenched with saturated NH ₄ Cl (30 mL), extracted with ethyl acetate (30 mL, 3 times), and dried over anhydrous sodium sulfate. The mixture was concentrated in vacuo and purified by normal phase column chromatography (silica column, 35%-70% ethyl acetate in hexanes) to give (7-methyl-[1,2,4]triazolo[1,5- a ]pyridin-5-yl)-[4-(trifluoromethoxy)phenyl]methanol (629 mg) (a compound of the present invention) as a solid. ¹ H NMR (600 MHz, CDCl3) δ ppm 8.31 (s, 1H), 7.55 (d, J = 9 Hz, 2H), 7.50 (s, 1H), 7.25 (m, 2H, overlapped with CDCl3), 6.58 (s, 1H), 6.32 (d, J = 5 Hz, 1H), 4.81 (s, J = 5 Hz, 1H), 2.45 (s, 3H). Synthesis Example 2 Preparation of 5-[Fluoro-[4-(trifluoromethoxy)phenyl]methyl]-7-methyl-[1,2,4]triazolo[1,5- a ]pyridine (Compound 8)

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

Table 1-6. A relates to the structure shown below. [Table 1] R ^1b、R ^1c、R ^1d、R ^1e、R ²、R ³and R ⁴It is H. R ^1a R ^1a R ^1a R ^1a R ^1a R ^1a H t -Bu NO ₂ O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF ₅ C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1c、R ^1d、R ^1e、R ²、R ³and R ⁴It is H. R ^1b R ^1b R ^1b R ^1b R ^1b R ^1b H t -Bu NO ₂ O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF ₅ C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1b、R ^1d、R ^1e、R ²、R ³and R ⁴It is H. R ^1c R ^1c R ^1c R ^1c R ^1c R ^1c H t -Bu NO ₂ O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF ₅ C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1b、R ^1c、R ^1d、R ^1e、R ³and R ⁴It is H; R ²It's Me R ^1a R ^1a R ^1a R ^1a R ^1a R ^1a H t -Bu NO ₂ O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF ₅ C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1c、R ^1d、R ^1e、R ³and R ⁴It is H; R ²It's Me R ^1b R ^1b R ^1b R ^1b R ^1b R ^1b H t -Bu NO ₂ O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF ₅ C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1b、R ^1d、R ^1e、R ³and R ⁴It is H; R ²It's Me R ^1c R ^1c R ^1c R ^1c R ^1c R ^1c H t -Bu NO ₂ O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluoro-p E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF ₅ C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1b、R ^1c、R ^1d、R ^1e、R ³and R ⁴It is H; R ²System Cl R ^1a R ^1a R ^1a R ^1a R ^1a R ^1a H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF ₅ C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1c、R ^1d、R ^1e、R ³and R ⁴It is H; R ²System Cl R ^1b R ^1b R ^1b R ^1b R ^1b R ^1b H t -Bu NO ₂ O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF ₅ C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1b、R ^1d、R ^1e、R ³and R ⁴It is H; R ²System Cl R ^1c R ^1c R ^1c R ^1c R ^1c R ^1c H t -Bu NO ₂ O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF ₅ C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1b、R ^1c、R ^1d、R ^1e、R ³and R ⁴It is H; R ²It is MeO R ^1a R ^1a R ^1a R ^1a R ^1a R ^1a H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1c、R ^1d、R ^1e、R ³and R ⁴It is H; R ²It is MeO R ^1b R ^1b R ^1b R ^1b R ^1b R ^1b H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1b、R ^1d、R ^1e、R ³and R ⁴It is H; R ²It is MeO R ^1c R ^1c R ^1c R ^1c R ^1c R ^1c H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1b、R ^1c、R ^1d、R ^1e、R ²and R ⁴It is H; R ³It's Me R ^1a R ^1a R ^1a R ^1a R ^1a R ^1a H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1c、R ^1d、R ^1e、R ²and R ⁴It is H; R ³It's Me R ^1b R ^1b R ^1b R ^1b R ^1b R ^1b H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1b、R ^1d、R ^1e、R ²and R ⁴It is H; R ³It's Me R ^1c R ^1c R ^1c R ^1c R ^1c R ^1c H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1b、R ^1c、R ^1d、R ^1e、R ²and R ⁴It is H; R ³System Cl R ^1a R ^1a R ^1a R ^1a R ^1a R ^1a H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1c、R ^1d、R ^1e、R ²and R ⁴It is H; R ³System Cl R ^1b R ^1b R ^1b R ^1b R ^1b R ^1b H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1b、R ^1d、R ^1e、R ²and R ⁴It is H; R ³System Cl R ^1c R ^1c R ^1c R ^1c R ^1c R ^1c H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1b、R ^1c、R ^1d、R ^1e、R ²and R ⁴It is H; R ³It is MeO R ^1a R ^1a R ^1a R ^1a R ^1a R ^1a H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1c、R ^1d、R ^1e、R ²and R ⁴It is H; R ³It is MeO R ^1b R ^1b R ^1b R ^1b R ^1b R ^1b H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1b、R ^1d、R ^1e、R ²and R ⁴It is H; R ³It is MeO R ^1c R ^1c R ^1c R ^1c R ^1c R ^1c H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1b、R ^1c、R ^1d、R ^1e、R ²and R ³It is H; R ⁴It's Me R ^1a R ^1a R ^1a R ^1a R ^1a R ^1a H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1c、R ^1d、R ^1e、R ²and R ³It is H; R ⁴It's Me R ^1b R ^1b R ^1b R ^1b R ^1b R ^1b H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1b、R ^1d、R ^1e、R ²and R ³It is H; R ⁴It's Me R ^1c R ^1c R ^1c R ^1c R ^1c R ^1c H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1b、R ^1c、R ^1d、R ^1e、R ²and R ³It is H; R ⁴System Cl R ^1a R ^1a R ^1a R ^1a R ^1a R ^1a H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1c、R ^1d、R ^1e、R ²and R ³It is H; R ⁴System Cl R ^1b R ^1b R ^1b R ^1b R ^1b R ^1b H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1b、R ^1d、R ^1e、R ²and R ³It is H; R ⁴System Cl R ^1c R ^1c R ^1c R ^1c R ^1c R ^1c H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1b、R ^1c、R ^1d、R ^1e、R ²and R ³It is H; R ⁴It is MeO R ^1a R ^1a R ^1a R ^1a R ^1a R ^1a H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1c、R ^1d、R ^1e、R ²and R ³It is H; R ⁴It is MeO R ^1b R ^1b R ^1b R ^1b R ^1b R ^1b H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl R ^1a、R ^1b、R ^1d、R ^1e、R ²and R ³It is H; R ⁴It is MeO R ^1c R ^1c R ^1c R ^1c R ^1c R ^1c H t -Bu NO2 O -i -Pr S(O) _CF3 2-Fluorophenyl F CF ₃ OH _OCH2CH = _CH2 SO ₂ CF ₃ 3-Fluorophenyl Cl _CH2F OCOCH _{3 OCH2C≡CH CO2Me} 4-Fluorophenyl Br CHF ₂ NHMe O- c -Pr CO ₂ Et N -Me-4-pyrazolyl I OMe NMe ₂ OCF ₃ Cyano 3-Me-5-Isoxazolyl Me OE NHCHO OCHF ₂ C(O)NHMe 4-Fluorophenoxy E O -n -Pr NHA _OCH2CF3 C(O)NMe ₂ Pr OPh NMeAc SF5 C(=NOMe)Me i -Pr CH= _CH2 COMe SCF ₃ C(=NOEt)Me c -Pr C≡CH SiMe ₃ SCHF ₂ Phenyl [Table 2]

Table 2 is the same as Table 1, except that the general structure is changed to the above structure. [Table 3]

Table 3 is the same as Table 1, except that the general structure is changed to the above structure. [Table 4]

Table 4 is the same as Table 1, except that the general structure is changed to the above structure. [Table 5]

Table 5 is the same as Table 1, except that the general structure is changed to the above structure. [Table 6]

Table 6 is the same as Table 1, except that the general structure is changed to the above structure. [Table 7]

Table 7 is the same as Table 1, except that the general structure is changed to the above structure.

The compounds disclosed herein will generally be used as invertebrate pest control active ingredients in a composition (i.e., a formulation) wherein at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent is used as a carrier. The formulation or composition components are selected to be consistent with the physical properties of the active ingredient, the mode of administration, and environmental factors such as soil type, moisture, and temperature.

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 suspension emulsions) that may be thickened into gels as desired. The general types of aqueous liquid compositions are soluble concentrates, suspension concentrates, capsule suspensions, concentrates, microemulsions, oil-in-water emulsions, flowable concentrates and suspension emulsions. The general types of non-aqueous liquid compositions are emulsifiable concentrates, microemulsifiable concentrates, dispersible concentrates and oil dispersions.

General types of solid compositions are powders, dusts, granules, pellets, granules, tablets, tablets, filled 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. The active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively, the entire formulation of the active ingredient can be encapsulated (or "coated"). Encapsulation can control or delay the release of the active ingredient. Emulsifiable granules combine the advantages of both emulsifiable concentrate formulations and dry granular formulations. High-strength compositions are mainly used as intermediates for further formulations.

Sprayable formulations are typically dispersed in a suitable medium prior to spraying. Such liquid and solid formulations are formulated to be easily diluted in a spray medium, usually water, but occasionally another suitable medium like aromatic hydrocarbons or paraffin or vegetable oil. Spray volumes may range from about one liter to several thousand liters per hectare, but are more typically in the range of about ten to several hundred liters per hectare. Sprayable formulations may be tank mixed with water or another suitable medium for foliar treatment by air or ground application, or for application to the growing medium of the plant. Liquid and dry formulations may be metered directly into a drip irrigation system, or metered into trenches during planting. Liquid and solid formulations can be administered as seed treatments to seeds of crops and other desired vegetation prior to planting to protect developing roots and other below-ground plant parts and/or foliage by systemic uptake.

The formulation will typically contain effective amounts of active ingredient, diluent and surfactant in an amount totaling up to 100 weight percent within the following approximate ranges. Weight Percent Active ingredients Diluent Surfactant Water-dispersible and water-soluble granules, tablets and powders 0.001-90 0-99.999 0-15 Oil dispersions, suspensions, emulsions, solutions (including emulsifiable concentrates) 1-50 40-99 0-50 Powder 1-25 70-99 0-5 Granules and Balls 0.001-99 5-99.999 0-15 High strength composition 90-99 0-10 0-2

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

Liquid diluents include, for example, water, N , N -dimethylalkaneamides (e.g., N , N -dimethylformamide), limonene, dimethyl sulfoxide, N -alkylpyrrolidone (e.g., N -methylpyrrolidone), alkyl phosphates (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, wax (e.g., white mineral oil, normal alkanes, isoalkanes), alkylbenzenes, alkylnaphthalenes, glycerol, triacetin, sorbitol, aromatic hydrocarbons, dearomatized aliphatic compounds, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as isoamyl acetate, hexyl acetate, and the like. esters, such as heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isobornyl acetate, other esters such as alkylated lactic acid esters, dibasic esters, alkyl and aryl benzoates, gamma-butyrolactone, and alcohols which may be linear, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecanol, isooctadecyl alcohol, cetyl alcohol, lauryl alcohol, tridecanol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, cresol and benzyl alcohol. Liquid diluents also include glycerides of saturated and unsaturated fatty acids (typically _C6 - _C22 ), such as plant seed and fruit oils (e.g., olive oil, castor oil, linseed oil, sesame oil, corn oil (maize oil), peanut oil, sunflower oil, grapeseed oil, safflower oil, cottonseed oil, soybean oil, rapeseed oil, coconut oil and palm kernel oil), animal-derived fats (e.g., tallow, lard, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated (e.g., methylated, ethylated, butylated) fatty acids, which can be obtained by hydrolysis of glycerides 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.

The solid and liquid compositions of the present disclosure often include one or more surfactants. When added to a liquid, a surfactant (also called a "surface-active agent") generally changes, most often reduces, the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in the surfactant molecule, the surfactant can be used as a wetting agent, dispersant, emulsifier, or defoaming agent.

Surfactants can be classified as nonionic, anionic or cationic. Nonionic surfactants that can be used in the compositions of the present invention include, but are not limited to: alcohol alkoxylates, such as those based on natural alcohols 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 trans-block polymers wherein the terminal blocks are prepared from propylene oxide; compounds; 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, polyethoxylated esters (such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters and polyethoxylated glycerol fatty acid esters); other sorbitan derivatives such as sorbitol 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.

Useful anionic surfactants include, but are not limited to, alkylarylsulfonic acids and salts thereof; carboxylated alcohol or alkylphenol ethoxylates; diphenylsulfonate derivatives; lignin and lignin derivatives, such as lignin sulfonates; maleic acid or succinic acid or their anhydrides; olefin sulfonates; phosphates, such as phosphates of alcohol alkoxylates, phosphates of alkylphenol alkoxylates, and phosphates of styrylphenol ethoxylates; protein-based surfactants; sarcosine derivatives; styrylphenol ether sulfates; 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 -Alkyltaurines; sulfonates of benzene, cumene, toluene, xylene and dodecylbenzene and tridecylbenzene; sulfonates of condensed naphthalene; sulfonates of naphthalene and alkylnaphthalene; sulfonates of petroleum grades; sulfosuccinates; and sulfosuccinates and their derivatives, such as dialkylsulfosuccinates.

Useful cationic surfactants include, but are not limited to, amides and ethoxylated amides; amines such as N -alkylpropylenediamine, 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 ammonium acetate 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.

Also useful in the composition 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 a number of published references, including McCutcheon's Emulsifiers and Detergents , annual American and International Editions, published by The Manufacturing Confectioner Publishing Co., McCutcheon Division; Sisely and Wood, Encyclopedia of Surface Active Agents , Chemical Publ. Co., Inc., New York, 1964; and AS Davidson and B. Milwidsky, Synthetic Detergents , Seventh Edition, John Wiley and Sons [John Wiley & Sons], New York, 1987.

The compositions of the present disclosure may also include formulation aids and additives known to those skilled in the art as auxiliary formulation agents (some of which may also be considered to function as solid diluents, liquid diluents, or surfactants). Such formulation aids and additives may control: pH (buffers), foaming during processing (defoamers, such as polysiloxanes), precipitation of active ingredients (suspending agents), viscosity (twitch thickeners), microbial growth in containers (antimicrobial agents), product freezing (antifreeze agents), color (dye/pigment dispersions), elution (film formers or adhesives), evaporation (evaporation inhibitors), and other formulation properties. Film formers include, for example, polyvinyl acetate, polyvinyl acetate copolymers, polyvinyl pyrrolidone-vinyl acetate copolymers, polyvinyl alcohol, polyvinyl alcohol copolymers, and waxes. Examples of formulation aids and additives include those listed in McCutcheon's Volume 2: Functional Materials, annual International and North American editions, published by the McCutcheon Division of Manufacturing Confectioner Publishing Company; and PCT Publication WO 03/024222.

The compound of formula 1 and any other active ingredients are typically incorporated into the composition of the invention by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent. Solutions including emulsifiable concentrates can be prepared by simply mixing the ingredients. If the solvent of the liquid composition intended for use as an emulsifiable concentrate is immiscible with water, an emulsifier is typically added to emulsify the solvent containing the active ingredient when it is diluted with water. The active ingredient slurry with a particle size of 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, US 3,060,084) or further processed by spray drying to form water-dispersible granules. Dry preparations generally require a dry milling process, resulting in an average particle size in the range of 2 to 10 μm. Powders and powders can be prepared by blending and usually by grinding (e.g. with a hammer mill or fluid energy mill). Granules and sphericals can be prepared by spraying the active substance onto a preformed granular carrier or by agglomeration techniques. See, Browning, "Agglomeration," Chemical Engineering , December 4, 1967, pp. 147-48; Perry's Chemical Engineer's Handbook, 4th ed., McGraw-Hill, New York, 1963, pp. 8-57 et seq., and WO 91/13546. Spheroids may be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules may be prepared as taught in U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442, and DE 3,246,493. Tablets may be prepared as taught in US 5,180,587, US 5,232,701 and US 5,208,030. Films may be prepared as taught in GB 2,095,558 and US 3,299,566.

For further information on the formulation area, see TS Woods, "The Formulator's Toolbox - Product Forms for Modern Agriculture, " in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, eds . T. Brooks and TR Roberts, Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also US 3,235,361, col. 6, lines 16 to col. 7, line 19, and Examples 10-41; US 3,309,192, col. 5, lines 43 to col. 7, line 62, and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167, and 169-182; US 2,891,855, col. 3, lines 66 to col. 5, line 17, and Examples 1-4; Klingman, Weed Control as a Science , John Wiley and Sons, Inc., New York, 1961, pp. 81-96; Hance et al., Weed Control as a Science. Weed Control Handbook, 8th ed., Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, UK, 2000.

In the following examples, all formulations were prepared in a conventional manner. Compound numbers refer to compounds in Index Tables AC. Without further elaboration, it is believed that one skilled in the art can utilize the present disclosure to its fullest extent using the foregoing description. Therefore, the following examples should be construed as merely illustrative and not limiting of the present disclosure in any way. Unless otherwise indicated, percentages are by weight. Example A High Strength Concentrate Compound 1 98.5% Silica Aerogel 0.5% Synthetic amorphous fine silica 1.0% Example B Wettable powder Compound 4 65.0% Dodecylphenol polyglycol ether 2.0% Sodium lignosulfonate 4.0% Sodium aluminosilicate 6.0% Montmorillonite (calcined) 23.0% Example C Granules Compound 8 10.0% Magnesium aluminum sepiolite granules (low volatile matter, 0.71/0.30 mm; USS 25-50 sieve) 90.0% Example D Squeeze out the pellets Compound 10 25.0% Anhydrous sodium sulfate 10.0% Crude calcium lignin sulfonate 5.0% Sodium alkylnaphthalene sulfonate 1.0% Calcium/Magnesium Bentonite 59.0% Example E Emulsifiable concentrates Compound 15 10.0% Polyoxyethylene sorbitan hexaoleate 20.0% C ₆ -C ₁₀ fatty acid methyl esters 70.0% Example F Microemulsion Compound 2 5.0% Polyvinylpyrrolidone-vinyl acetate copolymer 30.0% Alkyl polysaccharide 30.0% Glyceryl Monooleate 15.0% water 20.0% Example G Seed treatment Compound 7 20.00% Polyvinylpyrrolidone-vinyl acetate copolymer 5.00% Lignan acid wax 5.00% Calcium lignosulfonate 1.00% Polyoxyethylene/polyoxypropylene block copolymer 1.00% Stearyl Alcohol (POE 20) 2.00% Polysiloxane 0.20% Coloring agent red dye 0.05% water 65.75% Example H Fertilizer sticks Compound 9 2.5% Pyrrolidone-styrene copolymer 4.8% Tristyrylphenyl 16-ethoxylate 2.3% talc 0.8% Corn starch 5.0% Slow-release fertilizer 36.0% Kaolin 38.0% water 10.6% Example I Suspension concentrate Compound 13 35% Butyl polyoxyethylene/polypropylene block copolymer 4.0% Stearic acid/polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone based defoamer 0.1% 1,2-Benzisothiazoline-3-one 0.1% water 53.7% Example J Emulsion in water Compound 11 10.0% Butyl polyoxyethylene/polypropylene block copolymer 4.0% Stearic acid/polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone based defoamer 0.1% 1,2-Benzisothiazoline-3-one 0.1% Aromatic petroleum hydrocarbons 20.0 water 58.7% Example K Oil dispersion Compound 12 25% Polyoxyethylene sorbitan hexaoleate 15% Organic modified bentonite 2.5% Fatty acid methyl esters 57.5% Example L Suspension lotion Compound 3 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 based defoamer 0.1% 1,2-Benzisothiazoline-3-one 0.1% Aromatic petroleum hydrocarbons 20.0% water 53.7%

The compounds disclosed herein exhibit activity against a broad spectrum of invertebrate pests. Such pests include invertebrates that inhabit a variety of environments, such as plant foliage, roots, soil, harvested crops or other foods, building structures, or animal integuments. Such pests include, for example, invertebrates that feed on foliage (including leaves, stems, flowers, and fruits), seeds, wood, textile fibers, or animal blood or tissues and thereby cause injury or damage to, for example, growing or storing crops, forests, greenhouse crops, ornamental plants, nursery crops, stored food or fiber products, or buildings or other structures or their contents, or are harmful to animal health or public health. Those skilled in the art will appreciate that not all compounds are equally effective against all growth stages of all pests.

Therefore, the compounds and compositions of the present invention can be used agronomically to protect field crops from herbivorous invertebrate pests and can also be used non-agriculturally to protect other horticultural crops and plants from herbivorous invertebrate pests. This utility includes protecting crops and other plants (i.e., agricultural and non-agricultural) containing genetic material introduced by genetic engineering (i.e., transgenic) or modified by induced mutation to provide favorable traits. Examples of such traits include tolerance to herbicides, resistance to phytophagous pests (e.g., insects, mites, aphids, spiders, nematodes, snails, plant pathogenic fungi, bacteria, and viruses), improved plant growth, increased tolerance to adverse growing conditions (such as high or low temperatures, low or high soil moisture, and high salinity), increased flowering or fruiting, greater harvest yield, faster maturation, higher quality and/or nutritional value of the harvested product, or improved storage or processing characteristics of the harvested product. Transgenic plants can be modified to express a variety of traits. Examples of plants containing traits provided by genetic engineering or mutation include corn, cotton, soybean, and potato varieties expressing Bacillus thuringiensis insecticides, such as YIELD GARD ^® , KNOCKOUT ^® , STARLINK ^® , BOLLGARD ^® , NuCOTN ^® and NEWLEAF ^® , INVICTA RR ² PRO ^™ , and herbicide-tolerant corn, cotton, soybean, and rapeseed varieties, such as ROUNDUP READY ^® , LIBERTY LINK ^® , IMI ^® , STS ^® and CLEARFIELD ^® , as well as crops expressing N -acetyltransferase (GAT) to provide resistance to glyphosate herbicide, or crops containing the HRA gene that provides resistance to herbicides that inhibit acetolactate synthase (ALS). The compounds and compositions of the invention may exhibit an enhancement effect of a trait introduced by genetic engineering or modified by induction, thereby enhancing the phenotypic expression or effectiveness of the trait, or increasing the invertebrate pest control effectiveness of the compounds and compositions of the invention. In particular, the compounds and compositions of the invention may exhibit an enhancement effect of the phenotypic expression of proteins or other natural products toxic to invertebrate pests to provide greater than additive control of such pests.

The composition of the present disclosure may also optionally include plant nutrients, for example, a fertilizer composition comprising at least one plant nutrient selected from 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 liquid or solid form. Of note are solid preparations in the form of granules, small sticks or tablets. A solid formulation containing a fertilizer composition can be prepared by mixing the compound or composition of the present disclosure with a fertilizer composition and formulation ingredients, and then preparing the formulation by methods such as granulation or extrusion. Alternatively, a solid formulation can be prepared by spraying a solution or suspension of the compound or composition of the present disclosure in a volatile solvent onto a previously prepared fertilizer composition in the form of a size-stable mixture (e.g., granules, small rods or tablets), and then evaporating the solvent.

Non-agricultural uses refer to invertebrate pest control in areas other than fields of crop plants. Non-agricultural uses of the compounds and compositions of this invention include invertebrate pest control in stored grains, legumes, and other foods, and textiles such as clothing and carpeting. Non-agricultural uses of the compounds and compositions of this invention also include invertebrate pest control in ornamental plants, forests, gardens, roadsides and railroad lands, and turf such as lawns, golf courses, and pastures. Non-agricultural uses of the compounds and compositions of this invention also include invertebrate pest control in houses and other structures that may be occupied by humans and/or companion animals, farm animals, ranch animals, zoo animals, or other animals. Non-agricultural uses of the compounds and compositions of the present invention also include the control of pests such as termites that may damage wood or other structural materials used in buildings.

Non-agricultural uses of the compounds and compositions of the present invention also include protecting human and animal health by controlling and combating parasitic or infectious disease-transmitting invertebrate pests. Control and combating of animal parasites include controlling and combating external parasites that parasitize on the surface of the host animal (e.g., shoulders, armpits, abdomen, inner thighs) and internal parasites that parasitize in the host animal (e.g., stomach, intestines, lungs, veins, subcutaneous, lymphatic tissue). External parasitic or disease-transmitting pests include, for example, chiggers, ticks, lice, mosquitoes, flies, mites and fleas. Internal parasites include heartworms, hookworms and worms. The compounds and compositions of the present disclosure are suitable for systemic and/or non-systemic control of parasitic infestations or infections in animals. The compounds and compositions of the present disclosure are particularly suitable for combating external parasitic or disease-transmitting pests. The compounds and compositions of the present disclosure are suitable for combating parasites that infest the following animals: agricultural working animals, such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, hens, turkeys, ducks, geese and bees; pet animals and domestic animals, such as dogs, cats, pet birds and aquarium fish; and so-called experimental animals, such as hamsters, guinea pigs, rats and mice. By combating these parasites, mortality and performance decline (in meat, milk, wool, fur, eggs, honey, etc.) are reduced, thus applying a composition comprising a compound of the present disclosure allows for more economical and simple animal husbandry.

Examples of agricultural or non-agricultural invertebrate pests include eggs, larvae and adults of the order Lepidoptera, such as armyworms, cutworms, loopers and heliothines of the family Noctuidae (e.g., Sesamia inferens Walker, Sesamia nonagrioides Lefebvre, Southern Armyworm ( Spodoptera eridania Cramer), Fall Armyworm (Spodoptera frugiperda ), Beet Armyworm ( Spodoptera exigua Hübner), Cotton Leafworm ( Spodoptera littoralis Boisduval), Yellow Band Armyworm ( Spodoptera ornithogalli Guenée), Black Cutworm ( Agrotis ipsilon Hufnagel), Bean Moth ( Anticarsia gemmatalis Hübner), green fruit armyworm ( Lithophane antennata Walker), cabbage armyworm ( Barathra brassicae Linnaeus), soybean armyworm ( Pseudoplusia includens Walker), cabbage looper ( Trichoplusia ni Hübner), tobacco budworm ( Heliothis virescens Fabricius)); borers, casebearers, webworms, coneworms, cabbageworms and skeletonizers from the family Pyralidae (e.g., European corn borer ( Ostrinia nubilalis Hübner), navel orangeworm ( Amyelois transitella Walker), corn root webworm ( Crambus caliginosellus Clemens), sod webworms (Crambus caliginosellus Clemens), rice leaf borer ( Herpetogramma licarsisalis Walker), sugarcane two-spotted borer ( Chilo infuscatellus Snellen), tomato borer ( Neoleucinodes elegantalis Guenée), tuber borer ( Cnaphalocrocis medinalis Guenée), grape leaf roller ( Desmia funeralis Hübner), cucumber silkworm borer ( Diaphania nitidalis Stoll), cabbage heartworm ( Hellula hydralis Guenée), yellow stem borer ( Scirpophaga incertulas Walker), rice white borer ( Scirpophaga innotata Walker), Scirpophaga nivella Fabricius, Chilo polychrysus Meyrick, Chilo suppressalis Walker, Crocidolomia binotalis Zeller; leafrollers, budworms, seed worms and fruit worms of the family Tortricidae (e.g., Cydia pomonella Linnaeus, Paralobesia viteana Clemens, Grapholita molesta Busck, Cryptophlebia leucotreta Meyrick, Gymnandrosoma aurantianum Lima, Redbanded Roller ( Cytophlebia leucotreta Meyrick), Argyrotaenia velutinana Walker), Choristoneura rosaceana Harris, Epiphyas postvittana Walker, Eupoecilia ambiguella Hübner, Pandemis pyrusana Kearfott, Platynota stultana Walsingham, Pandemis cerasana Hübner, Pandemis heparana Denis &Schiffermüller); and many other economically important Lepidoptera (e.g., Plutella xylostella Linnaeus, Pectinophora gossypiella Saunders, Lymantria dispar Linnaeus, Peach borer ( Carposina niponensis Walsingham), peach aphid ( Anarsia lineatella Zeller), potato borer ( Phthorimaea operculella Zeller), curtain leafminer ( Phyllonorycter blancardella Fabricius), apple moth ( Lithocolletis ringoniella Matsumura), tuber borer ( Lerodea eufala Edwards), spiral leafminer ( Leucoptera scitella Zeller); eggs, nymphs and adults of the order Blattodea, including cockroaches from the families Blattellidae and Blattidae (e.g., Oriental cockroach ( Blatta orientalis Linnaeus), Asian cockroach ( Blatella asahinai Mizukubo), German cockroach ( Blettella germanica Linnaeus), Brown-banded cockroach ( Supella longipalpa Fabricius, American cockroach ( Periplaneta americana Linnaeus), brown cockroach ( Periplaneta brunnea Burmeister), Madeira cockroach ( Leucophaea maderae Fabricius), black-breasted cockroach ( Periplaneta fuliginosa Serville), Australian cockroach ( Periplaneta australasiae Fabr.), lobster cockroach ( Nauphoeta cinerea Olivier), and smooth cockroach ( Symphloce pallens Stephens); eggs, leaf-feeding, fruit-feeding, root-feeding, seed-feeding, and vesicular tissue-feeding larvae and adults of the order Coleoptera, including weevils from the families Anthribidae, Bruchidae, and Curculionidae (e.g., cotton seed weevil ( Anthonomus grandis Boheman), rice water weevil ( Lissorhoptrus oryzophilus Kuschel), grain weevil ( Sitophilus granarius Linnaeus), rice weevil ( Sitophilus oryzae Linnaeus), bluegrass weevil ( Listronotus maculicollis Dietz), bluegrass weevil ( Sphenophorus parvulus Gyllenhal), hunting long-beaked weevil ( Sphenophorus venatus vestitus Chittenden), Rocky Mountain grain weevil ( Sphenophorus cicatristriatus Fahraeus); flea beetle (Chrysomelidae), cucumber beetle (Cucumber beetle), rootworm (rootworm), leaf beetle (leaf beetle), potato beetle (potato beetle) beetles and leafminers (e.g., Colorado potato beetle ( Leptinotarsa decemlineata Say), western corn rootworm ( Diabrotica virgifera LeConte)); scarabs and other beetles from the family Scarabaeidae (e.g., Japanese scarabs ( Popillia japonica Newman), Oriental scarabs ( Anomala orientalis Waterhouse), northern rhinoceros beetles ( Cyclocephala borealis Arrow), southern rhinoceros beetles ( Cyclocephala immaculata Olivier or C. lurida Bland), dung beetles, and white grubs ( Aphodius ) species), black lawn turtle ( Ataenius spretulus Haldeman), green June turtle ( Cotinis nitida Linnaeus), Asian garden turtle ( Maladera castanea Arrow), May/June turtle ( Phyllophaga species) and European turtle ( Rhizotrogus majalis Razoumowsky); carpet beetles from the family Dermestidae; wireworms from the family Elateridae; bark beetles from the family Scolytidae and flour beetles from the family Tenebrionidae.

In addition, agricultural and non-agricultural pests include: eggs, adults and larvae of the order Dermoptera, including earwigs from the family Forficulidae (e.g., European earwig ( Forficula auricularia Linnaeus), black earwig ( Chelisoches morio Fabricius)); eggs, larvae, adults and nymphs of the order Hemiptera, such as plant bugs from the family Miridae, cicadas from the family Cicadidae, leafhoppers from the family Cicadidae (e.g., Empoasca ) species), bed bugs from the family Cimicidae (e.g., Cimex lectularius Linnaeus), planthoppers from the families Fulgoridae and Delphacidae, treehoppers from the family Membracidae, psyllids from the families Liviidae, Psyllidae, and Triozidae, whiteflies from the family Aleyrodidae, aphids from the family Aphididae, phylloxera from the family Phylloxeridae, mealybugs from the family Pseudococcidae, scales from the families Coccidae, Diaspididae, and Margarodidae, lace bugs from the family Tingidae, The family includes crickets , crickets, and stink bugs, including red bugs and cotton bugs from the family Pyrrhocoridae .

Agricultural and non-agricultural pests also include: eggs, larvae, nymphs and adults of the order Acari (worms), such as spider mites and red mites of the family Tetranychidae (e.g., Panonychus ulmi Koch, Tetranychus urticae Koch, Tetranychus mcdanieli McGregor); flat mites of the family Tenuipalpidae (e.g., citrus flat mite ( Brevipalpus lewisi McGregor)); rust mites of the family Eriophyidae (e.g., mite and bud mites, as well as other leaf-feeding mites and mites of importance to human and animal health, namely, dust mites of the family Epidermoptidae, hair follicle mites of the family Demodecidae, grain mites of the family Glycyphagidae; ticks of the family Ixodidae, commonly known as hard ticks (e.g., deer tick ( Ixodes scapularis Say), Australian paralysis tick ( Ixodes holocyclus Neumann), American dog tick ( Dermacentor variabilis Say), lone star tick ( Amblyomma americanum Linnaeus)) and ticks of the family Argasidae, commonly known as soft ticks (e.g., recurrent fever tick ( Ornithodoros turicata Duges), common chicken tick ( Argas radiatus Raillet); scab mites and itch mites of the families Psoroptidae, Pyemotidae, and Sarcoptidae; eggs, adults, and larvae of the order Orthoptera, including grasshoppers, locusts, and crickets (e.g., migratory grasshoppers (e.g., Melanoplus sanguinipes Fabricius, M. differentialis Thomas), American grasshoppers (e.g., Schistocerca americana Drury), Schistocerca gregaria Forsskål, Locusta migratoria Linnaeus, bush locusts (e.g., locust ( Zonocerus species), house crickets ( Acheta domesticus Linnaeus), mole crickets (e.g., Scapteriscus vicinus Scudder and Scapteriscus borellii Giglio-Tos); eggs, adults and larvae of the order Diptera, including leaf miners (e.g., Liriomyza species, such as Liriomyza sativae Blanchard), midges, fruit flies (Tephritidae), wheat flies (e.g., Oscinella frit Linnaeus), soil maggots ( maggots), house flies (e.g., Musca domestica Linnaeus), small 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 species, Phormia species) and other muscoid fly pests, horse flies (e.g., Tabanus species), bot flies (e.g., Gasterophilus species, Oestrus ), cattle grubs (e.g., Hypoderma species), deer flies (e.g., Chrysops species), keds (e.g., Melophagus ovinus Linnaeus) and other Brachycera, mosquitoes (e.g., Aedes species, Anopheles species, Culex species), black flies (e.g., Prosimulium species, Simulium species), biting midges, sand flies (e.g., flies, sciarids, and other Nematocera; eggs, adults, and larvae of the order Pteroptera, including onion thrips ( Thrips tabaci Lindeman), flower thrips ( Frankliniella species), and other leaf-feeding thrips; insect pests of the order Hymenoptera, including ants of the family Formicidae, including the Florida wood ant ( Camponotus floridanus Buckley), the red wood ant ( Camponotus ferrugineus Fabricius), the black wood ant ( Camponotus pennsylvanicus De Geer), the white-legged ant ( Technomyrmex albipes F. Smith), the big-headed ant ( Pheidole ) species), ghost ants ( Tapinoma melanocephalum Fabricius); Pharaoh ants ( Monomorium pharaonis Linnaeus), little fire ants ( Wasmannia auropunctata Roger), fire ants ( Solenopsis geminata Fabricius), red imported fire ants ( Solenopsis invicta Buren), Argentine ants ( Iridomyrmex humilis Mayr), crazy ants ( Pararechina longicornis Latreille), pavement ants ( Tetramorium caespitum Linnaeus), cornfield ants ( Lasius alienus Förster), and odorous house ants (Solanum alienus Förster). ant) ( Tapinoma sessile Say). Other Hymenoptera, including bees (including carpenter bees), hornets, yellow jackets, wasps and sawflies ( Neodipiron species; Cephus species); insect pests of the order Isoptera, including the families Termitidae (e.g., Macrotermes species, Odontotermes obesus Rambur ), Kalotermitidae (e.g., Cryptotermes species), and Rhinotermitidae (e.g., Reticulitermes species, Coptotermes species, Heterotermes species). tenuis Hagen), Eastern underground termites ( Reticulitermes flavipes Kollar ), Western underground termites ( Reticulitermes hesperus Bank), Taiwanese milky termites ( Coptotermes formosanus Shiraki), West Indian drywood termites ( Incisitermesimmigrans Snyder ), powdery termites ( Cryptotermes brevis Walker), drywood termites ( Incisitermes snyderi Light), Southeastern underground termites ( Reticulitermes virginicus Banks), Western drywood termites ( Incisitermes minor Hagen), arboreal termites (arboreal termites) such as elephant termites ( Nasutitermes ) species, as well as other economically important termites; insect pests of the order Lycoceridae, such as silverfish ( Lepisma saccharina Linnaeus) and firebrat ( Thermobia domestica Packard); insect pests of the orders Mallophaga and Phthiraptera, including head lice ( Pediculus humanus capitis De Geer), body lice (Pediculus humanus Linnaeus), chicken body lice ( Menacanthus stramineus Nitzsch), dog hair lice ( Trichodectes canis De Geer), velvet lice ( Goniocotes gallinae De Geer), sheep body lice ( Bovicolaovis Schrank ), short-nosed cattle lice ( Haematopinus eurysternus Nitzsch), long-nosed cattle lice ( Linognathus vituli Linnaeus, and other sucking and chewing 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 Bouché), dog flea ( Ctenocephalides canis Curtis ), chicken flea ( Ceratophyllus gallinae Schrank ), sucking flea ( Echidnophaga gallinacea Westwood), human flea ( Pulex irritans Linnaeus), and other fleas that bother mammals and birds. Other arthropod pests covered include spiders of the order Araneae, such as the brown recluse spider ( Loxosceles reclusa Gertsch & Mulaik) and the black widow spider ( Latrodectus mactans Fabricius), and centipedes of the order Scolopendra, such as the house centipede ( Scutigera coleoptrata Linnaeus).

Examples of invertebrate pests of stored grain include the truncatus borer ( Prostephanus truncatus Horn), the small grain borer ( Rhyzopertha dominica Fabricius), the rice weevil ( Sitophilus oryzae Linnaeus), the maize weevil ( Sitophilus zeamais Motschulsky), the bean weevil ( Callosobruchus maculatus Fabricius), the red grain borer ( Tribolium castaneum Herbst), the grain weevil ( Sitophilus granarius Linnaeus), the Indian grain borer ( Plodia interpunctella Hübner), the Mediterranean flour beetle ( Ephestia kuehniella Zeller) and the long-horned or rusty grain borer ( Cryptoletes ferrugineus Stephens).

The compounds of the present disclosure may be active against members of the classes Nematoda, Cestoda, Trematodes, and Acanthocephala, including members of the economically important orders Strongylida, Ascaridida, Oxyurida, Rhabditida, Spirurida, and Enoplida, such as, but not limited to, economically important agricultural pests (i.e., root knot nematodes in the genus Meloidogyne , lesion nematodes in the genus Pratylenchus , stubby root nematodes in the genus Trichodorus , nematodes, etc.) and animal and human health pests (i.e. all economically important trematodes, tapeworms and roundworms, such as Strongylus vulgaris in horses, Toxocara canis in dogs, Haemonchus contortus in sheep, Dirofilaria immitis Leidy in dogs, Anoplocephala perfoliata in horses, Fasciola hepatica Linnaeus in animals, etc.).

The compounds disclosed herein may have activity against pests in the order Lepidoptera (e.g., Alabama argillacea Hübner (cotton leafworm), Archips argyrospila Walker (fruit leaf roller), A. rosana Linnaeus (European leaf roller) and other Archips species, Chilo suppressalis Walker (rice borer), Cnaphalocrocis medinalis Guenée (rice leaf roller), Corn root borer (corn root webworm), Crambus teterrellus Zincken (bluegrass webworm), Cydia pomonella Linnaeus (codling moth), Earias insulana Boisduval (spiny stem borer), Earias vittella Fabricius (spotted stem borer), Helicoverpa armigera Hübner (old continental stem borer), Helicoverpa zea Boddie (corn earworm), Tobacco budworm (tobacco budworm), Herpetogramma licarsisalis Walker (sod webworm), Lobesia botrana Denis & Schiffermüller (grape leaf roller), Pectinophora gossypiella Saunders (pink bollworm), Phyllocnistis citrella Stainton (citrus leafminer), Pieris rapae ( Pieridae ) brassicae Linnaeus (large white cabbage butterfly), Pieris rapae Linnaeus (small white cabbage butterfly), Plutella xylostella Linnaeus (diamondback moth), Spodoptera exigua Hübner (beet armyworm), Spodoptera litura Fabricius (tobacco cutworm, cluster caterpillar), Spodoptera frugiperda (fall armyworm), Trichoplusia ni Hübner (cabbage looper), and T uta absoluta Meyrick (tomato leafminer).

The compounds disclosed herein have significant activity against members of the order Hemiptera, including: pea aphid ( Acyrthosiphon pisum Harris), cowpea aphid ( Aphis craccivora Koch), black bean aphid (Aphis pelargonis), cotton aphid ( Aphis gossypii Glover), apple aphid ( Aphis pomi De Geer), leaf roller aphid ( Aphis spiraecola Patch), foxglove aphid ( Aulacorthum solani Kaltenbach), strawberry aphid ( Chaetosiphon fragaefolii Cockerell), Russian wheat aphid ( Diuraphis noxia Kurdjumov/Mordvilko), plantain round-tailed aphid ( Dysaphis plantaginea Passerini), apple aphid ( Eriosoma lanigerum Hausmann), peach aphid ( Hyalopterus pruni Geoffroy), radish aphid ( Lipaphis pseudobrassicae Davis), wheat aphid ( Metopolophium dirrhodum Walker), potato aphid ( Macrosiphum euphorbiae Thomas), peach aphid ( Myzus persicae Sulzer), lettuce aphid ( Nasonovia ribisnigri Mosley), species of the genus Pemphigus (root aphids and gall aphids), maize aphid ( Rhopalosiphum maidis Fitch), rice aphid ( Rhopalosiphum padi Linnaeus), wheat aphid ( Schizaphis graminum Rondani), wheat aphid ( Sitobion avenae Fabricius), alfalfa aphid ( Therioaphis maculata Buckton), citrus aphid ( Toxoptera aurantii Boyer de Fonscolombe), and brown citrus aphid ( Toxoptera citricidus Kirkaldy); Adelges species (adelgids); Phylloxera devastatrix Pergande (pecanphylloxera); Bemisia tabaci Gennadius (tobacco whitefly, sweetpotato whitefly), Bemisia argentifolii Bellows & Perring (silverleaf whitefly), Dialeurodes citri Ashmead (citrus whitefly), and Trialeurodes vaporariorum Westwood (greenhouse whitefly); Empoasca fabae Harris (potato leafhopper), Laodelphax striatellus Fallén (smaller brown planthopper), and planthopper), Macrosteles quadrilineatus Forbes (aster leafhopper), Nephotettix cincticeps Uhler (green rice leafhopper), Nephotettix nigropictus Stål (rice leafhopper), Nilaparvata lugens Stål (brown planthopper), Peregrinus maidis Ashmead (corn planthopper), Sogatella furcifera Horváth (white-backed planthopper), Tagosodes orizicolus Muir (rice delphacid), Typhlocyba pomaria McAtee (white apple leafhopper), leafhopper), Erythroneura spp. (grape leafhoppers); Magicidada septendecim Linnaeus (periodical cicada); Icerya purchasi Maskell (cottony cushion scale), Quadraspidiotus perniciosus Comstock (San Jose scale); Planococcus citri Risso (citrus mealybug); Pseudococcus species (other mealybug groups); Cacopsylla pyricola Foerster (pear psylla), Trioza diospyri Ashmead (persimmon psylla).

The compounds of the present disclosure are also active against members from the order Hemiptera, including: Pseudo-green stink bug (rice green stink bug), Cucurbita serrata (squash bug), Blissus leucopterus leucopterus Say, Cimex lectularius (bed bug), Square-winged web bug (cotton web bug), Tomato stink bug ( Cyrtopeltis modesta Distant), Cotton black-winged red stink bug (cotton red stink bug), Brown stink bug ( Euschis servus Say), Single-spotted stink bug ( Euschis variolarius Palisot de Beauvois), Black-banded red-gland stink bug species (species of stink bug complex), Brown-winged stink bug (Brown marbled toon), Pine root stink bug ( Leptoglossus corculus Say), American pasture stink bug ( Lygus lineolaris Palisot de Beauvois), southern green rice stink bug, American rice stink bug, milkweed stink bug, cotton blind bug ( Pseudatomoscelis seriatus Reuter). Other insect orders controlled by the compounds of the present disclosure include the order Tenoptera (e.g., Frankliniella occidentalis Pergande, Scirtothrips citri Moulton, Scirtothrips variabilis Beach, and Onion Scirtothrips; and the order Coleoptera (e.g., Colorado potato beetle, Mexican bean beetle, and wireworms of the genera Agriotes , Athous , or Limonius ).

Of note is the use of the compounds disclosed herein for controlling and combating the western flower artichoke. Of note is the use of the compounds disclosed herein for controlling and combating the potato leaf worm. Of note is the use of the compounds disclosed herein for controlling and combating the cotton aphid. Of note is the use of the compounds disclosed herein for controlling and combating the green peach aphid. Of note is the use of the compounds disclosed herein for controlling and combating the sweet potato whitefly (whitefly).

The compounds disclosed herein can also be used to increase the vitality of crop plants. This method includes contacting the crop plants (e.g., leaves, flowers, fruits or roots) or the seeds from which the crop plants grow with a compound of formula 1 in an amount (i.e., a biologically effective amount) sufficient to achieve the desired plant vitality effect. Typically, the compound of formula 1 is administered as a formulated composition. Although the compound of formula 1 is usually administered directly to the crop plants or their seeds, the compounds can also be administered to the location of the crop plants, i.e., the environment of the crop plants, particularly to a portion of the environment that is close enough to allow the compound of formula 1 to migrate to the crop plants. The location associated with this method most commonly includes a growth medium (i.e., a medium that provides nutrients to the plants), typically the soil in which the plants are grown. Thus, treatment of crop plants to increase the vigor of crop plants comprises 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 having Formula 1 .

Increased crop vigor can result in one or more of the following observed effects: (a) optimal crop establishment as demonstrated by superior seed germination, crop emergence, and crop stand; (b) enhanced crop growth as demonstrated by rapid and vigorous leaf growth (e.g., as measured by leaf area index), plant height, tiller number (e.g., for rice), root mass, and total dry weight of the vegetative body of the crop; (c) improved crop yield as demonstrated by time to flowering, duration of flowering, number of flowers, total biomass accumulation (i.e., yield), and/or product grade marketability of fruit or grain (i.e., product quality); (d) enhanced ability of crops to tolerate or prevent infection by plant diseases and infestation by arthropod, nematode, or mollusk pests; and (e) Increased ability of crops to tolerate environmental stresses such as exposure to extreme heat, suboptimal water or phytotoxic chemicals.

The compounds of the present disclosure can increase the vigor of treated plants compared to untreated plants by killing or otherwise preventing feeding by phytophagous invertebrate pests in the plant's environment. In the absence of such control of phytophagous invertebrate pests, pests reduce plant vigor by consuming plant tissues or sap, or transmitting plant pathogens such as viruses. Even in the absence of phytophagous invertebrate pests, the compounds of the present disclosure can increase plant vigor by altering plant metabolism. Generally, if the plant is grown in a non-ideal environment, i.e., an environment that contains one or more aspects that are not conducive to the plant achieving its full genetic potential that it would perform in an ideal environment, then the vigor of the crop plant will be most significantly increased by treating the plant with the compounds of the present disclosure.

Of note is a method for increasing the vigor of a crop plant, wherein the crop plant is grown in an environment that includes phytophagous invertebrate pests. Also of note is a method for increasing the vigor of a crop plant, wherein the crop plant is grown in an environment that does not include phytophagous invertebrate pests. Also of note is a method for increasing the vigor of a crop plant, wherein the crop plant is grown in an environment that includes an amount of water that is less than an ideal amount of water to support the growth of the crop plant. Of note is a method for increasing the vigor of a crop plant, wherein the crop is rice. Also of note is a method for increasing the vigor of a crop plant, wherein the crop is maize (corn). Also of note is a method for increasing the vigor of a crop plant, wherein the crop is soybean.

The compounds of the present disclosure may also be mixed with one or more other biologically active compounds or agents, including insecticides, fungicides, nematicides, bactericides, miticides, herbicides, herbicide safeners, growth regulators such as insect bark inhibitors and rooting stimulants, chemosterilants, chemones, repellents, attractants, signalogens, feeding stimulants, other biologically active compounds or insect pathogenic bacteria, viruses or fungi to form multi-component pesticidal agents, thereby imparting an even broader spectrum of agricultural and non-agricultural effects. 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 and at least one additional biologically active compound or agent, wherein the at least one additional component is selected from the group consisting of a surfactant, a solid diluent and a liquid diluent. For the mixtures disclosed herein, the other biologically active compound or agent can be formulated with the compounds of the present invention (including compounds of Formula 1) to form a premix, or the other biologically active compound or agent can be formulated separately from the compounds of the present invention (including compounds of Formula 1) and the two formulations are combined together (e.g., in a spray tank) before application, or alternatively, the two formulations are applied sequentially.

Examples of such biologically active compounds or agents that can be formulated with the compounds of the present disclosure are insecticides such as abatin, acetamiprid, cyfluthrin, acetamiprid, cyfluthrin, cyfluthrin ([( 3S , 4R, 4aR, 6S , 6aS , 12R, 12aS , 12bS )-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a, 12,12a ,12b - decahydro-6,12-dihydroxy-4,6a,12b-trimethyl - 11-oxo-9-(3-pyridyl) -2H , 11H -naphtho[2,1- b ]pyrano[3,4- e ]- ] pyran-4-yl] methylcyclopropane carboxylate), sulfadiazine, dimethoate, avermectin, azadirachtin, azoxystrobin, propylthiocarbamate, chloranil, bifenthrin, bifenazate, diflunisal, borate, phenthiocarb, cadastre, carbaryl, carbamate, chlorpyrifos, carzol, chloranil, chlorpyrifos, methyl chlorpyrifos, cycloheximide, tetracycline, thiamethoxam, bromocyanamide (3-bromo-1-(3-chloro-2-pyridyl)- N -[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-1 H -pyrazole-5-carboxamide), cyclobromothiolide (3-bromo- N- [2-bromo-4-chloro-6-[[(1-cyclopropylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyridyl) -1H -pyrazole-5-carboxamide), cypermethrin, cyclohexidine (( 5S , 8R )-1-[(6-chloro-3-pyridyl)methyl]-2,3,5,6,7,8-hexahydro-9-nitro-5,8-epoxy- 1H -imidazo[1,2- a ] nitrogen compound), butyric acid, flucythrin, high-efficiency flucythrin, tri-cypermethrin, high-efficiency flucythrin, high-efficiency flucythrin, cypermethrin, cis-cypermethrin, ζ-cypermethrin, cypermethrin, deltamethrin, diafenthiuron, diazepam, dieldrin, dimethoate, tetrafluthrin, dimehypo, dimethoate, dimethoate, benzyl methacrylate, emamectin, Endosulfan, cypermethrin, ethoprolin, ethomethrin, fenbutanil, cypermethrin, fenthiocarb, fenoxycarb, cypermethrin, cypermethrin, flumioxam, flutoquinone (2-ethyl-3,7-dimethyl-6-[4-(trifluoromethoxy)phenoxy]-4-quinolylmethyl carbonate), fluazifop, flufenamid, flucythrinate, flumethrin, flufenamid, flutolanil, flupyraduron (α E )-2-[[2-chloro-4-(trifluoromethyl)phenoxy]methyl]-α-(methoxymethylene)phenylacetic acid methyl ester), diflunisal (5-chloro-2-[(3,4,4-trifluoro-3-butene-1-yl)sulfonyl]thiazole), fluopyram, fluopyram, flupyrrole (1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(2-methyl-2-propen-1-yl)amino]-4-[(trifluoromethyl)sulfinyl] -1H -pyrazole-3-carbonitrile), flupyrrol (4-[[(6-chloro-3-pyridyl)methyl](2,2-difluoroethyl)amino]-2(5 H )-furanone), fluvalinate, fluvalinate, cypermethrin, formetanate, thiamethoxam, chlorfenapyr, tefluthrin ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl 2,2-dimethyl-3-[(1 Z )-3,3,3-trifluoro-1-propene-1-yl]cyclopropanecarboxylate), fluazifop, thiophanate, flufenacet, pyrimidine, indomethacin, insecticide soap, isopropylamidophos, cyfluthrin, marasmus, cyfluthrin ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl (1 R ,3 S )-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate), cyfluthrin, metaldehyde, methamidophos, chlorpyrifos, methiocarb, cypermethrin, methoprene, methoxychlor, flumethrin, chloranil, chloranil, monocrotophos, monofluthrin ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl 3-( 2-cyano-1-propene-1-yl)-2,2-dimethylcyclopropanecarboxylate), nicotine, nitram, nitrobenzamide, nitrobenzamide, fluazifop, noviflumuron, cypermethrin, parathion, methyl parathion, permethrin, phorate, phosphamidon, phosphamidon, pirimicarb, profenofos, profluthrin, cyfluthrin, pyrimethamine (1,3,5-trimethyl- N -(2-methyl-1-oxypropyl)- N -[3-(2-methylpropyl)-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl] -1H -pyrazole-4-carboxamide), pymetrozine, pyraclostrobin, pyrethrin, cypermethrin, pyraclostrobin, pyrimidine, pyraclostrobin, pyrimidine, pyraclostrobin, pyrimidine ((α E )-2-[[[2-[(2,4-dichlorophenyl)amino]-6-(trifluoromethyl)-4-pyrimidinyl]oxy]methyl]-α-(methoxymethylene)phenylacetic acid methyl ester), pyraclostrobin, pyriproxyfen, rotenone, ryanodine, flucythrin, ethyl spinetoram, spinetoram, spiroamyl, spiroamyl, spiroamyl, ethyl spinetoram, sulfaprophos, fluazifop ( N- [methyl oxide [1-[6-(trifluoromethyl)-3-pyridinyl]ethyl]-λ ⁴ -sulfenyl]cyanamide), chlorfenapyr, pyrimidine, flubenzuron, tefluthrin, terbufos, chlorpyrifos, tetramethrin, tetrafluthrin ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl 2,2,3,3-tetramethylcyclopropanecarboxylate), tetrazolylamide, thiamethoxam, thiomethoxam, thiosulfate, thiosultap-sodium, thiazolylsulfuron (3-phenyl-5-(2-thienyl)-1,2,4-oxadiazole), chlorfenapyr, tralomethrin, triazolam, triflumuron, triflumuron (2,4-dioxy-1-(5-pyrimidinylmethyl)-3-[3-(trifluoromethyl)phenyl]-2 H -pyrido[1,2- a ]pyrimidine salts), thiocarbamide, Bacillus thuringiensis delta-endotoxin, insect pathogenic bacteria, insect pathogenic viruses and insect pathogenic fungi.

It is worth noting that insecticides such as abatin, acetamiprid, flumethrin, cypermethrin, abimethrin, avermectin, azadirachtin, propylthiocarb, chlorpyrifos, cypermethrin, phenthiocarb, cadastrene, carbaryl, cypermethrin, chloranil, chlorpyrifos, clothianidin, bromocyanamide, cyclobromocyanamide, cypermethrin, cyfluthrin, beta-cypermethrin, cyhalothrin, and cypermethrin are not suitable for insecticides. High-efficiency cyhalothrin, high-efficiency cyhalothrin, cypermethrin, cis-cypermethrin, ζ-cypermethrin, mefenamic acid, deltamethrin, dieldrin, dimethoate, benzyl methoxyfen, imamitrin, endosulfan, cypermethrin, ethoprop, ethomethrin, ethomethoxazole, cypermethrin, fenthiocarb, fenoxycarb, cypermethrin, flumethrin, flufenamid, flumetolone, fluazifop-butyl, flufenamid, flufenoxuron, flutolanil, flufenamid, flufenoxuron, flutolanil, flufenoxuron ... Flumepyrrole, flupyridinone, flufenacet, fenflufenthrin, thiazophos, sevoflumethrin, fluflubenzuron, flufenhydrazone, imidacloprid, indoxacarb, lufenuron, flufluthrin, flufenacet, methiocarb , methomyl, methoprene, methoxyfenazine, metofluthrin, monofluthrin, nitenpyram, nitfenethane, flufenuron, dimethiocarb, pirflubutamide, pymetrozine, pyrethrin, pyridafen, acetamiprid Ether, pyrimidine, pyriproxyfen, ryanodine, ethyl colostrum, colostrum, spiromethanil, spiromethanil, spiromethanil, spiromethanil, fluazifop, cypermethrin, tetrathrin, thiamethoxam, thiocarb, cyfluthrin, tralomethrin, triazolam, triflumuron, cypermethrin, sphingomyelin, δ-endotoxin of Bacillus thuringiensis, all strains of Bacillus thuringiensis and all strains of nuclear polyhedrosis virus.

One embodiment of a biological agent for admixture with the compounds of the present disclosure includes insect pathogenic bacteria, such as Bacillus thuringiensis, and encapsulated delta-endotoxins of Bacillus thuringiensis prepared by the ^CellCap® process, such as ^MVP® and ^MVPII® bioinsecticides ( ^CellCap® , ^MVP® and ^MVPII® are trademarks of Mycogen Corporation, Indianapolis, Indiana, USA); insect pathogenic fungi, such as green muscardine fungi; fungus); and insect pathogenic (naturally occurring and genetically modified) viruses, including bacilliviruses, nuclear polyhedroviruses (NPVs), such as Spodoptera exigua NPV (HzNPV) and Anagrapha falcifera nucleopolyhedrovirus (AfNPV); and granuloviruses (GVs), such as Cydia pomonella granulosis virus (CpGV).

One embodiment of the biological agent for use in admixture with the compounds of the present disclosure includes one or a combination of the following: (i) Actinomycetes , Agrobacterium , Arthrobacter , Alcaligenes, Aureobacterium , Azobacter , Bacillus, Beijerinckia , Bradyrhizobium , Brevibacillus , Burkholderia , Chromobacterium , Clostridium , Clavibacter , Comorbidomyces , Comamonas , Corynebacterium , Curtobacterium , Enterobacter, Flavobacterium , Gluconobacter , Hydrogenophaga, Klebsiella , Methylobacterium , Paenibacillus , Pasteuria , Photorhabdus , Phyllobacterium , Pseudomonas , Rhizobium , Serratia ), Sphingobacterium , Stenotrophomonas , Streptomyces , Variovorax , or Xenorhabdus , such as Bacillus amyloliquefaciens , Bacillus cereus , Bacillus firmus, Bacillus licheniformis , Bacillus pumilus, Bacillus sphaericus , Bacillus subtilis ), Bacillus thuringiensis, Bradyrhizobium japonicum , Chromobacterium subtsugae , Pasteuria nishizawae, Pasteuria penetrans , Pasteuria usage , Pseudomonas fluorescens and Streptomyces lydicus ; (ii) fungi, such as mushrooms; (iii) viruses, including bacilli, nuclear polyhedrosis viruses, such as Spodoptera exigua nuclear polyhedrosis virus and Spodoptera exigua nuclear polyhedrosis virus; and granuloviruses, such as the fruit borer granulovirus.

Of particular note are combinations where the other invertebrate pest control active ingredient belongs to a different chemical class than the compound of Formula 1 or has a different site of action than the compound. In some cases, combinations with at least one other invertebrate pest control active ingredient having a similar control spectrum but a different site of action will be particularly advantageous for resistance management. Thus, the compositions of the present disclosure may further comprise a biologically effective amount of at least one additional invertebrate pest control active ingredient having a similar control spectrum but belonging to a different chemical class or having a different site of action. Such additional biologically active compounds or agents include, but are not limited to, acetylcholine esterase (AChE) inhibitors, such as carbamates such as cypermethrin, cypermethrin, thiocarb, triazolam, and organophosphates such as chlorpyrifos; GABA-gated chloride channel antagonists, such as cyclodienes such as dieldrin and endosulfan, and phenylpyrazoles such as ethoxycyanamide and flubendiamide; sodium channel modulators, such as pyrethroids such as bifenthrin, cyfluthrin, high-efficiency cyfluthrin, tri-cypermethrin, high-efficiency cyhalothrin, cypermethrin, deltamethrin, transfluthrin, esfenvalerate, metofluthrin, and profluthrin; nicotine-type acetylcholine receptors (nA ChR) agonists, such as the nicotinoids acetamiprid, clothianidin, furothiocarb, pyramemith, nitenpyram, nitrobenz, thiamethoxam, and thiamethoxam, the sulfoximines fluazifop, the butenolides flupyralidone, and the mesoionics triflufenamic acid; nicotinoid acetylcholine receptor (nAChR) allosteric activators, such as the spinosyns ethylspondin and spinosad; chloride channel activators, such as avermectin, abatin, and emamectin; juvenile hormone analogs (juvenile hormone analogs) hormone mimics, such as benzylpyridin, methoprene, fenoxycarb, and pyriproxyfen; chordotonal organ modulators, such as pymetrozine, pyrimethoxam, and fluazifop; mites growth inhibitors, such as ethidium bromide; mitochondrial ATP synthase inhibitors, such as fenfluramide; uncouplers of oxidative phosphorylation by disrupting the proton gradient, such as bromocriptine; nicotinic acetylcholine receptor (nAChR) channel blockers, such as nereistoxin analog) moulting agents; chitosan biosynthesis inhibitors, such as the benzoylurea class flufenicol, fluazifop, lufenuron, fluazifop, perflumuron, and fluazifop, and phenthiazone; dipteran mites interferons (moulting agents disrupters, such as cypermethrin; corticosteroid receptor agonists, such as diarylformylhydrazides, methoxyfenozide and chlorfenazate; octopamine receptor agonists, such as amitraz; mitochondrial complex III electron transport inhibitors, such as flufenamic acid and bifenazate; mitochondrial complex I electron transport inhibitors, such as cypermethrin; voltage-dependent sodium channel blockers, such as indoxacarb; acetyl coenzyme A carboxylase inhibitors, such as tetronic acids and tetramic acids. acids) spiromethanil, spiromethanil, and spiromethanil; mitochondrial complex II electron transport inhibitors, such as the β-ketonitriles pyrimidine and fluazifop-butyl; ryanodine receptor modulators, such as anthranilic acid diamide (anthranilic acid diamide); diamides) chloranilamide and bromocyanamide, diamides such as fluazifop, and ryanodine receptor ligands such as ryanodine; compounds for which the target site responsible for the biological activity is unknown or uncharacterized, such as azadirachtin and pyrimidine; microbial disruptors of the intestinal membrane of insects, such as Bacillus thuringiensis and the delta-endotoxin it produces, and Bacillus sphaeroides; and biological agents, including nuclear polyhedrosis (NPV) viruses and other naturally occurring or genetically modified insecticidal viruses.

Other examples of biologically active compounds or agents that can be formulated with the compounds of the present disclosure are fungicides such as acibenzolar-S-methyl, aldimorph, pyraclostrobin, aminopyrifen, indazolesulfamide, dichlorvos, azoxystrobin, benalaxyl (including benalaxyl-M), chloranil, benomyl, benthiavalicarb (including benthiavalicarb-isopropyl), benzovintriazole, bethoxazin, cypermethrin, biphenyl, triazole, biphenylpyraclostrobin, blasticidin-S, boscalid, acetamiprid ... Bupirimate, buthidazole, chloranil, cyclohexane, diflubenzuron, cardan, carbendazim, chloroneb, thiophanate-methyl, chlozolinate, copper hydroxide, copper oxychloride, copper sulfate, syringystrobin, cyazofamid, cyfluanid, cymoxanil, cyproconazole, cyproconazole, dichlobentiazox, diffluanid , diclocymet, diclomezine, dicloran, diethofencarb, fenpropimorph, diflumetorim, dimethirimol, diniconazole, diniconazole-M, fenthion, dipymetitrone, dithianon, dithiolane, dodecanol, icoconazole, ethazine, oxazolidinone, enoxastrobin (also known as enestroburin), fluazifop, ethaboxam, ethirimol, etr idiazole), oxadiazole, fenamidone, enoxadone, chlorfenapyr, fenthiocarb, furamide, fenhexamide, fenoxanil, fenpicoxamid, fenpropidine, fenpropiazole, fenamidone, triphenyltin acetate, triphenyltin hydroxide, ferram , ferimzone, flutoquinone, pyridamidine, fluoxathiapiprolin, fluazinam, fludioxonil, flutoxinamide, fluindapyr, fluopicolide, fluopicolide, fluoxapiprolin, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, fluthiazolinone (fluthiazolin) lutianil), flutolanil, flutriafol, flutolanil, fumarate, phthalide, furalaxyl, furazolidone, hexaconazole, hymexazole, guazatine, imipenem, iminoctadine albesilate, iminoctadine acetate triacetate), inpyrfluxam, thiodicarb, ipconazole, ipfentrifluconazole, ipflufenoquin, isoprene, iprobenfos, iproconazole, propionyl, isoflurane, isoflurane, isoflurane, isoprene, isopyrazam, isoprene, kasugamycin, kresoxim-methyl, lancotrione, zinc mannopyrazone, mandelin dipropamid), mandestrobin, mannaipur, mapanipyrin, clofoconazole, sulfamethoxam, meptyldinocap, metalaxyl (including metalaxyl-M/mefenoxam), metconazole, methasulfocarb, metiram, fenoxam, metyltetraprole, mefentrazone, myclobutanil, naftitine, ferric iron (ferric arsenate) methanearsonate), flufenamic acid, octhilamide, furamide, orysastrobin, oxadixyl, oxathiapiprolin, oxolinic acid, oxpoconazole, oxychlorpyrifos, oxychlorpyrifos, penconazole, pencycuron, fluopicolide, penthiopyrad, perfurazoate, phosphorous acid (including its salts, for example, fosetyl-aluminum), picoxystrobin, piperazine, piperalin, polyoxin, thiabendazole, procymidone, procymidone, propamocarb, propacyclazole, methyl zinc naipor, proquinazid, prothiocarb, prothioconazole, Adepidyn®, pyraclostrobin, pyrapropoyne, pyraclostrobin, pyraziflumid, pyrafophos, pyrafenib, pyrbutamido ibutacarb), pyridachlometyl, pyrifenox, pyriofenone, perisoxazole, pyrimethanil, pyrifenox, pyrrolnitrin, pyroquilon, fluquinazole, quinmethionate, quinofumelin, quinoxyfen, pentachloronitrobenzene, silthiopyrad, fam), sedaxane, simeconazole, spiroxanil, streptomycin, sulfur, tebuconazole, tebufloquin, teclofthalam, chloranil, tetrachloronitrobenzene, terbinafine, fluconazole, thiophanate, thiophanate-methyl, thiophanate-methyl, salamide, thiophanate-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, myclobutanil, triazoxide, tribasic copper sulfate, copper sulfate), chlorpyrifos-butyl, trifloxystrobin, trifloxystrobin, triflumizole, trimoprhamide tricyclazole, trifloxystrobin, oxadiazine, meconazole, uniconazole, effective mycin, valifenalate (also known as valifenal), vinclozoline, zinc pyruvate, kiloglobulin, zoxamide, and 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1 H -pyrazol-1-yl]ethanone; nematicides such as fluopyram, spirothiocarb, thiocarb, thiothiazolin, abatin, iprodione, flufenoxam, dimethyl disulfide, thiothiazolin, 1,3-dichloropropylene (1,3-D), metamizole (sodium and potassium), dazomet, chloropicrin, fenamiphos, fenamiphos, cadusaphos, terbufos, imidazolin , imicyafos, acarb, carbofuran, tioxazafen, Bacillus hardy and Pasteurella kaissar; fungicides such as streptomycin; miticides such as amitraz, chlorpyrifos, cyhexatin, cyfluthrin, chlorpyrifos, ethidium bromide, quinamectin, fenbuterol, cypermethrin, mefenamic acid, thiamethoxam, cypermethrin and pyridamole.

In agricultural and non-agricultural applications, invertebrate pests are controlled by applying a biologically effective amount of one or more compounds of the present disclosure, generally in the form of a composition, to the pest environment, including infested agricultural and/or non-agricultural locations, to the area to be protected, or directly to the pest to be controlled.

Thus, the present disclosure includes a method for controlling and combating invertebrate pests in agricultural and/or non-agricultural applications, the method comprising contacting the invertebrate pest or its environment with a biologically effective amount of one or more compounds of the present disclosure or with 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 particulate compositions, wherein the additional active compound is present on the same particles as the compound of the present disclosure or on particles separate from those particles of the compound of the present disclosure.

To achieve contact with the compounds or compositions of the present disclosure to protect field crops from invertebrate pests, the compounds or compositions are usually applied to crop seeds before planting, applied to the foliage (e.g., leaves, stems, flowers, fruits) of crop plants, or applied to soil or other growth media before or after planting crops.

One embodiment of the contact method is by spraying. Alternatively, the granular composition comprising the compound of the present disclosure can be applied to plant leaves or soil. The compound of the present disclosure can also be effectively delivered by plant absorption by contacting the plant with a composition comprising the compound of the present disclosure applied as a soil drench, a granular preparation into the soil, a nursery box treatment, or a transplant drench. Of note is the composition of the present disclosure in the form of a soil drench liquid preparation. Also noteworthy is a method for controlling and combating invertebrate pests, the method comprising contacting an invertebrate pest or its environment with a biologically effective amount of the compound of the present disclosure or with a composition comprising a biologically effective amount of the compound of the present disclosure. Further noteworthy is this method, wherein the environment is soil and the composition is administered into the soil as a soil drench preparation. It is further noteworthy that the compounds of the present disclosure are also effective by topical application to the site of infestation. Other contact methods include applying the compounds or compositions of the present disclosure by direct spray and residual spray, air spray, gel, seed coating, microencapsulation, systemic absorption, bait, ear tag, bolus, sprayer, fumigant, aerosol, powder and many other methods. One embodiment of the contact method is a fertilizer granule, small stick or tablet that is stable in size and contains the compounds or compositions of the present disclosure. The compounds of the present disclosure can also be impregnated into materials used to make invertebrate pest control devices (e.g., insect nets).

The compounds disclosed herein can be used to treat all plants, plant parts and seeds. Plant and seed varieties and cultivars can be obtained by conventional propagation and breeding methods or by genetic engineering methods. Genetically modified plants or seeds (transgenic plants or seeds) are those in which a heterologous gene (transgene) has been stably integrated into the plant or seed genome. The transgene defined by the specific location of the transgene in the plant genome is called a transformation or transgenic event.

Genetically modified plants and seed cultivars that can be treated according to the present disclosure include those that resist one or more biological stresses (harmful organisms, such as nematodes, insects, mites, fungi, etc.) or abiotic stresses (drought, low temperature, soil salinization, etc.), or those that contain other desired characteristics. Plants and seeds can be genetically modified to show traits, such as herbicide tolerance, insect resistance, modified oil characteristics or drought tolerance. Useful genetically modified plants and seeds including a single gene conversion event or a combination of conversion events are listed in Table Z. Additional information for the genetic modifications listed in Table Z can be obtained from the following database: OECD BioTrack Product Database [Online Database]. USDA Animal and Plant Health Inspection Service was retrieved from OECD using the Internet <https://biotrackproductdatabase.oecd.org/byidentifier.aspx> [Online Database]. Deliberate Release and Placing on the EU Market of GMOs - GMO Register was retrieved from US Department of Agriculture using the Internet <http://www.aphis.usda.gov> [Online Database]. The following abbreviations were retrieved from the European Commission Joint Research Centre using the Internet <http://gmoinfo.jrc.ec.europa.eu> and used in the following Table Z: tol. for tolerance, res. for resistance, SU for sulfonylurea, ALS for acetolactate synthase, HPPD for 4-hydroxyphenylpyruvate dioxygenase, and NA for not available. [Table Z] crop Event Name Event Code Characteristics Gene Alfalfa J101 MON-00101-8 Glyphosate tolerance cp4 epsps (aroA:CP4) Alfalfa J163 MON-ØØ163-7 Glyphosate tolerance cp4 epsps (aroA:CP4) Mustard* 23-18-17 (Event 18) CGN-89465-2 High lauric acid oil te Mustard* 23-198 (Event 23) CGN-89465-2 High lauric acid oil te Mustard* 61061 DP-Ø61Ø61-7 Glyphosate tolerance gat4621 Mustard* 73496 DP-Ø73496-4 Glyphosate tolerance gat4621 Mustard* GT200 (RT200) MON-89249-2 Glyphosate tolerance cp4 epsps (aroA:CP4); goxv247 Mustard* GT73 (RT73) MON-ØØØ73-7 Glyphosate tolerance cp4 epsps (aroA:CP4); goxv247 Mustard* HCN10 (Topas 19/2) NA Glufosinate tolerance bar Mustard* HCN28 (T45) ACS-BNØØ8-2 Glufosinate tolerance pat (syn) Mustard* HCN92 (Topas 19/2) ACS-BNØØ7-1 Glufosinate tolerance bar Mustard* MON88302 MON-883Ø2-9 Glyphosate tolerance cp4 epsps (aroA:CP4) Mustard* MPS961 NA Phytic acid decomposition phyA Mustard* MPS962 NA Phytic acid decomposition phyA Mustard* MPS963 NA Phytic acid decomposition phyA Mustard* MPS964 NA Phytic acid decomposition phyA Mustard* MPS965 NA Phytic acid decomposition phyA Mustard* MS1 (B91-4) ACS-BNØØ4-7 Glufosinate tolerance bar Mustard* MS8 ACS-BNØØ5-8 Glufosinate tolerance bar Mustard* OXY-235 ACS-BNØ11-5 Benzonitrile resistance bxn Mustard* PHY14 NA Glufosinate tolerance bar Mustard* PHY23 NA Glufosinate tolerance bar Mustard* PHY35 NA Glufosinate tolerance bar Mustard* PHY36 NA Glufosinate tolerance bar Mustard* RF1 (B93-101) ACS-BNØØ1-4 Glufosinate tolerance bar Mustard* RF2 (B94-2) ACS-BNØØ2-5 Glufosinate tolerance bar Mustard* RF3 ACS-BNØØ3-6 Glufosinate tolerance bar bean EMBRAPA 5.1 EMB-PV051-1 Disease resistance ac1 (sense and antisense) eggplant EE-1 Insect resistance cry1Ac Carnation 11 (7442) FLO-07442-4 Sulfonylurea resistance; altered flower color surB; dfr; hfl (f3'5'h) Carnation 11363 (1363A) FLO-11363-1 Sulfonylurea resistance; altered flower color surB;dfr;bp40(f3'5'h) Carnation 1226A (11226) FLO-11226-8 Sulfonylurea resistance; altered flower color surB;dfr;bp40(f3'5'h) Carnation 123.2.2 (40619) FLO-4Ø619-7 Sulfonylurea resistance; altered flower color surB; dfr; hfl (f3'5'h) Carnation 123.2.38 (40644) FLO-4Ø644-4 Sulfonylurea resistance; altered flower color surB; dfr; hfl (f3'5'h) Carnation 123.8.12 FLO-4Ø689-6 Sulfonylurea resistance; altered flower color surB;dfr;bp40(f3'5'h) Carnation 123.8.8 (40685) FLO-4Ø685-1 Sulfonylurea resistance; altered flower color surB;dfr;bp40(f3'5'h) Carnation 1351A (11351) FLO-11351-7 Sulfonylurea resistance; altered flower color surB;dfr;bp40(f3'5'h) Carnation 1400A (11400) FLO-114ØØ-2 Sulfonylurea resistance; altered flower color surB;dfr;bp40(f3'5'h) Carnation 15 FLO-ØØØ15-2 Sulfonylurea resistance; altered flower color surB; dfr; hfl (f3'5'h) Carnation 16 FLO-ØØØ16-3 Sulfonylurea resistance; altered flower color surB; dfr; hfl (f3'5'h) Carnation 4 FLO-ØØØØ4-9 Sulfonylurea resistance; altered flower color surB; dfr; hfl (f3'5'h) Carnation 66 FLO-ØØØ66-8 Sulfonylurea resistance; delayed aging surB;acc Carnation 959A (11959) FLO-11959-3 Sulfonylurea resistance; altered flower color surB;dfr;bp40(f3'5'h) Carnation 988A (11988) FLO-11988-7 Sulfonylurea resistance; altered flower color surB;dfr;bp40(f3'5'h) Carnation 26407 IFD-26497-2 Sulfonylurea resistance; altered flower color surB;dfr;bp40(f3'5'h) Carnation 25958 IFD-25958-3 Sulfonylurea resistance; altered flower color surB;dfr;bp40(f3'5'h) endive RM3-3 NA Glufosinate tolerance bar endive RM3-4 NA Glufosinate tolerance bar endive RM3-6 NA Glufosinate tolerance bar cotton 19-51a DD-Ø1951A-7 Acetolactate synthase herbicide tolerance S4-HrA cotton 281-24-236 DAS-24236-5 Glufosinate tolerance; insect resistance pat(syn);cry1F cotton 3006-210-23 DAS-21Ø23-5 Glufosinate tolerance; insect resistance pat(syn);cry1Ac cotton 31707 NA Benzonitrile tolerance; insect resistance bxn;cry1Ac cotton 31803 NA Benzonitrile tolerance; insect resistance bxn;cry1Ac cotton 31807 NA Benzonitrile tolerance; insect resistance bxn;cry1Ac cotton 31808 NA Benzonitrile tolerance; insect resistance bxn;cry1Ac cotton 42317 NA Benzonitrile tolerance; insect resistance bxn;cry1Ac cotton BNLA-601 NA Insect resistance cry1Ac cotton BXN10211 BXN10211-9 Benzonitrile resistance bxn;cry1Ac cotton BXN10215 BXN10215-4 Benzonitrile resistance bxn;cry1Ac cotton BXN10222 BXN10222-2 Benzonitrile resistance bxn;cry1Ac cotton BXN10224 BXN10224-4 Benzonitrile resistance bxn;cry1Ac cotton COT102 SYN-IR102-7 Insect resistance vip3A(a) cotton COT67B SYN-IR67B-1 Insect resistance cry1Ab cotton COT202 Insect resistance 3A cotton Event 1 NA Insect resistance cry1Ac cotton GMF Cry1A GTL-GMF311-7 Insect resistance cry1Ab-Ac cotton GHB119 BCS-GH005-8 Insect resistance cry2Ae cotton GHB614 BCS-GH002-5 Glyphosate tolerance 2mepsps cotton GK12 NA Insect resistance cry1Ab-Ac cotton LLCotton25 ACS-GH001-3 Glufosinate tolerance bar cotton MLS 9124 NA Insect resistance cry1C cotton MON1076 MON-89924-2 Insect resistance cry1Ac cotton MON1445 MON-01445-2 Glyphosate tolerance cp4 epsps (aroA:CP4) cotton MON15985 MON-15985-7 Insect resistance cry1Ac; cry2Ab2 cotton MON1698 MON-89383-1 Glyphosate tolerance cp4 epsps (aroA:CP4) cotton MON531 MON-00531-6 Insect resistance cry1Ac cotton MON757 MON-00757-7 Insect resistance cry1Ac cotton MON88913 MON-88913-8 Glyphosate tolerance cp4 epsps (aroA:CP4) cotton Nqwe Chi 6 Bt NA Insect resistance NA? cotton SKG321 NA Insect resistance cry1A; CpTI cotton T303-3 BCS-GH003-6 Insect resistance; glufosinate tolerance cry1Ab;bar cotton T304-40 BCS-GH004-7 Insect resistance; glufosinate tolerance cry1Ab;bar cotton CE43-67B Insect resistance cry1Ab cotton CE46-02A Insect resistance cry1Ab cotton CE44-69D Insect resistance cry1Ab cotton 1143-14A Insect resistance cry1Ab cotton 1143-51B Insect resistance cry1Ab cotton T342-142 Insect resistance cry1Ab cotton PV-GHGT07 (1445) Glyphosate tolerance cp4 epsps (aroA:CP4) cotton EE-GH3 Glyphosate tolerance mepsps cotton EE-GH5 Insect resistance cry1Ab cotton MON88701 MON-88701-3 Dicamba and glufosinate tolerance Modified dmo; bar cotton OsCr11 Anti-allergy Modified Cry j Creeping Bentgrass ASR ³ 68 SMG-368ØØ-2 Glyphosate tolerance cp4 epsps (aroA:CP4) Eucalyptus 20-C Salt resistance codA Eucalyptus 12-5C Salt resistance codA Eucalyptus 12-5B Salt resistance codA Eucalyptus 107-1 Salt resistance codA Eucalyptus 1/9/2001 Salt resistance codA Eucalyptus 2/1/2001 Salt resistance codA Eucalyptus Cold resistance des9 Flax FP967 CDC-FL001-2 Acetolactate synthase herbicide tolerance als Lentil RH44 Imidazolidinone resistance als corn 3272 SYN-E3272-5 Modified α-amylase amy797E corn 5307 SYN-05307-1 Insect resistance ecry3.1Ab corn 59122 DAS-59122-7 Insect resistance; glufosinate tolerance cry34Ab1; cry35Ab1; pat corn 676 PH-000676-7 Glufosinate tolerance; pollination control pat; dam corn 678 PH-000678-9 Glufosinate tolerance; pollination control pat; dam corn 680 PH-000680-2 Glufosinate tolerance; pollination control pat; dam corn 98140 DP-098140-6 Glyphosate tolerance; acetolactate synthase herbicide tolerance gat4621;zm-hra corn Bt10 NA Insect resistance; glufosinate tolerance cry1Ab;pat corn Bt176 (176) SYN-EV176-9 Insect resistance; glufosinate tolerance cry1Ab;bar corn BVLA430101 NA Phytic acid decomposition phyA2 corn CBH-351 ACS-ZM004-3 Insect resistance; glufosinate tolerance cry9C;bar corn DAS40278-9 DAS40278-9 2,4-D tolerance aad-1 corn DBT418 DKB-89614-9 Insect resistance; glufosinate tolerance cry1Ac;pinII;bar corn DLL25 (B16) DKB-89790-5 Glufosinate tolerance bar corn GA21 MON-00021-9 Glyphosate tolerance mepsps corn GG25 Glyphosate tolerance mepsps corn GJ11 Glyphosate tolerance mepsps corn Fl117 Glyphosate tolerance mepsps corn GAT-ZM1 Glufosinate tolerance Pat corn LY038 REN-00038-3 Increased lysine cordapA corn MIR162 SYN-IR162-4 Insect resistance vip3Aa20 corn MIR604 SYN-IR604-5 Insect resistance mcry3A corn MON801 (MON80100) MON801 Insect resistance; glyphosate tolerance cry1Ab; cp4 epsps (aroA:CP4); goxv247 corn MON802 MON-80200-7 Insect resistance; glyphosate tolerance cry1Ab; cp4 epsps (aroA:CP4); goxv247 corn MON809 PH-MON-809-2 Insect resistance; glyphosate tolerance cry1Ab; cp4 epsps (aroA:CP4); goxv247 corn MON810 MON-00810-6 Insect resistance; glyphosate tolerance cry1Ab; cp4 epsps (aroA:CP4); goxv247 corn MON832 NA Glyphosate tolerance cp4 epsps (aroA:CP4); goxv247 corn MON863 MON-00863-5 Insect resistance cry3Bb1 corn MON87427 MON-87427-7 Glyphosate tolerance cp4 epsps (aroA:CP4) corn MON87460 MON-87460-4 Drought tolerance cspB corn MON88017 MON-88017-3 Insect resistance; glyphosate tolerance cry3Bb1;cp4 EPSPS (aroA:CP4) corn MON89034 MON-89034-3 Insect resistance cry2Ab2; cry1A.105 corn MS3 ACS-ZM001-9 Glufosinate tolerance; pollination control bar; barnase corn MS6 ACS-ZM005-4 Glufosinate tolerance; pollination control bar; barnase corn NK603 MON-00603-6 Glyphosate tolerance cp4 epsps (aroA:CP4) corn T14 ACS-ZM002-1 Glufosinate tolerance pat (syn) corn T25 ACS-ZM003-2 Glufosinate tolerance pat (syn) corn TC1507 DAS-01507-1 Insect resistance; glufosinate tolerance cry1Fa2;pat corn TC6275 DAS-06275-8 Insect resistance; glufosinate tolerance mocry1F;bar corn VIP1034 Insect resistance; glufosinate tolerance vip3A;pat corn 43A47 DP-043A47-3 Insect resistance; glufosinate tolerance cry1F;cry34Ab1;cry35Ab1;pat corn 40416 DP-040416-8 Insect resistance; glufosinate tolerance cry1F;cry34Ab1;cry35Ab1;pat corn 32316 DP-032316-8 Insect resistance; glufosinate tolerance cry1F;cry34Ab1;cry35Ab1;pat corn 4114 DP-004114-3 Insect resistance; glufosinate tolerance cry1F;cry34Ab1;cry35Ab1;pat melon Melon A NA Delayed maturation/aging sam-k melon Melon B NA Delayed maturation/aging sam-k pawpaw 55-1 CUH-CP551-8 Disease resistance prsv cp pawpaw 63-1 CUH-CP631-7 Disease resistance prsv cp pawpaw Huanong No. 1 NA Disease resistance prsv rep pawpaw X17-2 UFL-X17CP-6 Disease resistance prsv cp Petunia Dwarf Globe-CHS NA Modified product quality CHS inhibition Plum C-5 ARS-PLMC5-6 Disease resistance ppv cp Mustard** ZSR500 NA Glyphosate tolerance cp4 epsps (aroA:CP4); goxv247 Mustard** ZSR502 NA Glyphosate tolerance cp4 epsps (aroA:CP4); goxv247 Mustard** ZSR503 NA Glyphosate tolerance cp4 epsps (aroA:CP4); goxv247 Poplar Bt Poplar NA Insect resistance cry1Ac; API Poplar Populus hybrid clone 741 NA Insect resistance cry1Ac; API Poplar trg300-1 High fiber AaXEG2 Poplar trg300-2 High fiber AaXEG2 Potatoes 1210 amk NA Insect resistance cry3A Potatoes 2904/1 kgs NA Insect resistance cry3A Mustard** ZSR500 NA Glyphosate tolerance cp4 epsps (aroA:CP4); goxv247 Mustard** ZSR502 NA Glyphosate tolerance cp4 epsps (aroA:CP4); goxv247 Potatoes ATBT04-27 NMK-89367-8 Insect resistance cry3A Potatoes ATBT04-30 NMK-89613-2 Insect resistance cry3A Potatoes ATBT04-31 NMK-89170-9 Insect resistance cry3A Potatoes ATBT04-36 NMK-89279-1 Insect resistance cry3A Potatoes ATBT04-6 NMK-89761-6 Insect resistance cry3A Potatoes BT06 NMK-89812-3 Insect resistance cry3A Potatoes BT10 NMK-89175-5 Insect resistance cry3A Potatoes BT12 NMK-89601-8 Insect resistance cry3A Potatoes BT16 NMK-89167-6 Insect resistance cry3A Potatoes BT17 NMK-89593-9 Insect resistance cry3A Potatoes BT18 NMK-89906-7 Insect resistance cry3A Potatoes BT23 NMK-89675-1 Insect resistance cry3A Potatoes EH92-527-1 BPS-25271-9 Modified Starches/Carbohydrates gbss (antonym) Potatoes HLMT15-15 NA Insect and disease resistance cry3A; pvy cp Potatoes HLMT15-3 NA Insect and disease resistance cry3A; pvy cp Potatoes HLMT15-46 NA Insect and disease resistance cry3A; pvy cp Potatoes RBMT15-101 NMK-89653-6 Insect and disease resistance cry3A; pvy cp Potatoes RBMT21-129 NMK-89684-1 Insect and disease resistance cry3A;plrv orf1;plrv orf2 Potatoes RBMT21-152 NA Insect and disease resistance cry3A;plrv orf1;plrv orf2 Potatoes RBMT21-350 NMK-89185-6 Insect and disease resistance cry3A;plrv orf1;plrv orf2 Potatoes RBMT22-082 NMK-89896-6 Insect and disease resistance; glyphosate tolerance cry3A; plrv orf1; plrv orf2; cp4 epsps (aroA:CP4) Potatoes RBMT22-186 NA Insect and disease resistance; glyphosate tolerance cry3A; plrv orf1; plrv orf2; cp4 epsps (aroA:CP4) Potatoes RBMT22-238 NA Insect and disease resistance; glyphosate tolerance cry3A; plrv orf1; plrv orf2; cp4 epsps (aroA:CP4) Potatoes RBMT22-262 NA Insect and disease resistance; glyphosate tolerance cry3A; plrv orf1; plrv orf2; cp4 epsps (aroA:CP4) Potatoes SEMT15-02 NMK-89935-9 Insect and disease resistance cry3A; pvy cp Potatoes SEMT15-07 NA Insect and disease resistance cry3A; pvy cp Potatoes SEMT15-15 NMK-89930-4 Insect and disease resistance cry3A; pvy cp Potatoes SPBT02-5 NMK-89576-1 Insect resistance cry3A Potatoes SPBT02-7 NMK-89724-5 Insect resistance cry3A rice 7Crp#242-95-7 Anti-allergy 7crp rice 7Crp#10 NA Anti-allergy 7crp rice GM Shanyou 63 NA Insect resistance cry1Ab; cry1Ac rice Huahui-1/TT51-1 NA Insect resistance cry1Ab; cry1Ac rice LLRICE06 ACS-OS001-4 Glufosinate tolerance bar rice LLRICE601 BCS-OS003-7 Glufosinate tolerance bar rice LLRICE62 ACS-OS002-5 Glufosinate tolerance bar rice Tarom molaii + cry1Ab NA Insect resistance cry1Ab (truncated) rice GAT-OS2 Glufosinate tolerance bar rice GAT-OS3 Glufosinate tolerance bar rice PE-7 Insect resistance Cry1Ac rice 7Crp#10 NA Anti-allergy 7crp rice KPD627-8 High tryptophan OASA1D rice KPD722-4 High tryptophan OASA1D rice KA317 High tryptophan OASA1D rice HW5 High tryptophan OASA1D rice HW1 High tryptophan OASA1D rice B-4-1-18 Upright leaf semi-dwarf Δ OsBRI1 rice G-3-3-22 Half-length OSGA2ox1 rice AD77 Disease resistance DEF rice AD51 Disease resistance DEF rice AD48 Disease resistance DEF rice AD41 Disease resistance DEF rice 13pNasNaatAprt1 Low iron tolerance HvNAS1; HvNAAT-A; APRT rice 13pAprt1 Low iron tolerance APRT rice gHvNAS1-gHvNAAT-1 Low iron tolerance HvNAS1; HvNAAT-A; HvNAAT-B rice gHvIDS3-1 Low iron tolerance HvIDS3 rice HvNAAT1 Low iron tolerance HvNAAT-A; HvNAAT-B rice gHvNAS1-1 Low iron tolerance HvNAS1 rice NIA-OS006-4 Disease resistance WRKY45 rice NIA-OS005-3 Disease resistance WRKY45 rice NIA-OS004-2 Disease resistance WRKY45 rice NIA-OS003-1 Disease resistance WRKY45 rice NIA-OS002-9 Disease resistance WRKY45 rice NIA-OS001-8 Disease resistance WRKY45 rice OsCr11 Anti-allergy Modified Cry j rice 17053 Glyphosate tolerance cp4 epsps (aroA:CP4) rice 17314 Glyphosate tolerance cp4 epsps (aroA:CP4) Rose WKS82/130-4-1 IFD-52401-4 Changing colors 5AT; bp40 (f3'5'h) Rose WKS92/130-9-1 IFD-52901-9 Changing colors 5AT; bp40 (f3'5'h) Soybean 260-05 (G94-1, G94-19, G168) NA Modified oils/fatty acids gm-fad2-1 (silent site) Soybean A2704-12 ACS-GM005-3 Glufosinate tolerance Pat Soybean A2704-21 ACS-GM004-2 Glufosinate tolerance Pat Soybean A5547-127 ACS-GM006-4 Glufosinate tolerance Pat Soybean A5547-35 ACS-GM008-6 Glufosinate tolerance Pat Soybean CV127 BPS-CV127-9 Imidazolidinone resistance csr1-2 Soybean DAS68416-4 DAS68416-4 Glufosinate tolerance Pat Soybean DP305423 DP-305423-1 Modified oil/fatty acid; acetolactate synthase herbicide tolerance gm-fad2-1 (silent site); gm-hra Soybean DP356043 DP-356043-5 Modified Oil/Fatty Acid; Glyphosate Tolerant gm-fad2-1 (silencing site); gat4601 Soybean FG72 MST-FG072-3 Glyphosate and HPPD tolerance 2mepsps; hppdPF W336 Soybean GTS 40-3-2 (40-3-2) MON-04032-6 Glyphosate tolerance cp4 epsps (aroA:CP4) Soybean GU262 ACS-GM003-1 Glufosinate tolerance Pat Soybean MON87701 MON-87701-2 Insect resistance cry1Ac Soybean MON87705 MON-87705-6 Modified Oil/Fatty Acid; Glyphosate Tolerant fatb1-A (sense and antisense); fad2-1A (sense and antisense); cp4 epsps (aroA:CP4) Soybean MON87708 MON-87708-9 Dicamba and glyphosate tolerance dmo;cp4 epsps (aroA:CP4) Soybean MON87769 MON-87769-7 Modified Oil/Fatty Acid; Glyphosate Tolerant Pj.D6D; Nc.Fad3; cp4 epsps (aroA:CP4) Soybean MON89788 MON-89788-1 Glyphosate tolerance cp4 epsps (aroA:CP4) Soybean W62 ACS-GM002-9 Glufosinate tolerance bar Soybean W98 ACS-GM001-8 Glufosinate tolerance bar Soybean MON87754 MON-87754-1 High oil dgat2 Soybean DAS21606 DAS-21606 Aryloxyalkanoate and glufosinate tolerance Modified aad-12; pat Soybean DAS44406 DAS-44406-6 Aryloxyalkanoates, glyphosate and glufosinate tolerance Modified aad-12;2mepsps;pat Soybean SYHT04R SYN-0004R-8 Mesotrione tolerance Modified avhppd Soybean 9582.814.19.1 Insect resistance and glufosinate tolerance cry1Ac, cry1F, PAT pumpkin CZW3 SEM-ØCZW3-2 Disease resistance cmv cp, zymv cp, wmv cp pumpkin ZW20 SEM-0ZW20-7 Disease resistance zymv cp, wmv cp beet GTSB77 (T9100152) SY-GTSB77-8 Glyphosate tolerance cp4 epsps (aroA:CP4); goxv247 beet H7-1 KM-000H71-4 Glyphosate tolerance cp4 epsps (aroA:CP4) beet T120-7 ACS-BV001-3 Glufosinate tolerance Pat beet T227-1 Glyphosate tolerance cp4 epsps (aroA:CP4) sugar cane NXI-1T Drought tolerance EcbetA sunflower X81359 Imidazolidinone resistance als Bell pepper PK-SP01 NA Disease resistance cmv cp Tobacco C/F/93/08-02 NA Benzonitrile resistance bxn Tobacco Vector 21-41 NA Reduced nicotine NtQPT1 (antisense) tomato 1345-4 NA Delayed maturation/aging acc (truncated) tomato 35-1-N NA Delayed maturation/aging sam-k tomato 5345 NA Insect resistance cry1Ac tomato 8338 CGN-89322-3 Delayed maturation/aging accd tomato B SYN-0000B-6 Delayed maturation/aging pg (sense or antisense) tomato Da SYN-0000DA-9 Delayed maturation/aging pg (sense or antisense) sunflower X81359 Imidazolidinone resistance als tomato Da Dong No 9 NA Modified products NA tomato F (1401F, h38F, 11013F, 7913F) SYN-0000F-1 Delayed maturation/aging pg (sense or antisense) tomato FLAVR SAVR™ CGN-89564-2 Delayed maturation/aging pg (sense or antisense) tomato Huafan No 1 NA Delayed maturation/aging Anti-efe tomato PK-TM8805R (8805R) NA Disease resistance cmv cp Wheat MON71800 MON-718ØØ-3 Glyphosate tolerance cp4 epsps (aroA:CP4) *Argentina, **Poland, #Eggplant

Treatment of genetically modified plants and seeds with the compounds of the present disclosure may result in enhanced effects. For example, reduced dosage, expanded activity spectrum, increased tolerance to biotic/abiotic stresses, or enhanced storage stability may be greater than would be expected from the additive effects of simply administering the compounds of the present disclosure to genetically modified plants and seeds.

The compounds of the present disclosure may also be used in seed treatments to protect seeds from invertebrate pests. In the context of the present disclosure and the scope of the claims, treating seeds means contacting the seeds with a biologically effective amount of the compounds of the present disclosure, which are usually formulated into the compositions of the present disclosure. The seed treatment protects the seeds from invertebrate soil pests and generally can also protect the roots and other soil-contacted plant parts of the seedlings developed from the germinated seeds. The seed treatment may also provide protection to the leaves by translocating the compounds of the present disclosure or a second active ingredient in the developing plant. Seed treatments may be administered to seeds of all types, including those seeds of plants that will germinate to form genetic transformations to express specific traits. Representative examples include those expressing proteins toxic to invertebrate pests, such as Bacillus thuringiensis toxins, or those expressing herbicide resistance, such as glyphosate acetyltransferase that provides glyphosate resistance. Seed treatment with the compounds of the present disclosure can also increase the vigor of plants grown from the treated seeds.

One method of seed treatment is by spraying or dusting the seeds with the compounds of the present disclosure (i.e., as a formulated composition) prior to sowing the seeds. Compositions formulated for seed treatment typically include a film former or a binder. Thus, typically the seed coating composition of the present disclosure includes a biologically effective amount of a compound of formula 1 , its N -oxide or salt, and a film former or a binder. Seeds may be coated by spraying a flowable suspension concentrate directly into a tumbling bed of seeds and then drying the seeds. Alternatively, other formulation types such as wet powders, solutions, suspension emulsions, emulsifiable concentrates, and emulsions in water may be sprayed on the seeds. The method is particularly useful for applying the film coating to seeds. Various coating machines and methods are available to those skilled in the art. Suitable methods include those listed in P. Kosters et al., Seed Treatment: Progress and Prospects, 1994 BCPC Monograph No. 57 and the references listed therein.

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

Other insecticides that can be formulated with the compound of Formula 1 to provide a mixture useful for seed treatment include abatin, acetamiprid, flumethrin, amitraz, avermectin, azadirachtin, chlorpyrifos, bifenthrin, phenthiocarb, carbaryl, chlorpyrifos, chlorpyrifos, chlorthiazide ... Cypermethrin, high-efficiency cyfluthrin, tri-cyhalothrin, high-efficiency cyfluthrin, high-efficiency cyfluthrin, cypermethrin, cis-cypermethrin, ζ-cypermethrin, mefenamic acid, deltamethrin, dieldrin, dimethomorph, benzylchlorfenapyr, imamitrin, endosulfan, esfenvalerate, ethopropenil, ethomethrin, ethomethin, fenthiocarb, fenoxycarb, fenvalerate , fipronil, flufenacet, flubendiamide, flufenoxuron, flufenacet, flufenamid, thiazophos, fluflubenzuron, flufenhydrazone, imidacloprid, indoxacarb, lufenuron, cyanide Trifenzone, methiocarb, methomyl, methoprene, methoxyfenazine, nitenpyram, nitfenethane, flufenuron, dimethiocarb, pymetrozine, pyrethrin, pyridaben, acetamiprid, pyridoxime Propyl ether, ryanodine, ethyl styracid, styracid, spiromethoxam, spiromethoxam, spiromethoxam, fluazifop, cypermethrin, thiamethoxam, thiocarb, cyfluthrin, tralomethrin, triazolam, cyfluthrin, dapoxetine, dapoxetine, styrax, δ-endotoxin of Bacillus thuringiensis, all strains of Bacillus thuringiensis, and all strains of nuclear polyhedrosis virus.

Fungicides that can be formulated with the compound of Formula 1 to provide a mixture useful for seed treatment include indazolesulfuron, azoxystrobin, pyraclostrobin, carbendazim, cymoxanil, cymoxanil, cyproconazole, difenocycline, enoxadone, fluazinam, fludioxonil, fluquinconazole, fluopyram, fluoxastrobin, flutriafol, flutoxafenamide, cyproconazole, iprodione, metalaxyl, metalaxyl-M, metconazole, myclobutanil, paclobutrazol, fluopicolide, picoxystrobin, prothioconazole, pyraclostrobin, flutoxafenamide, sithiopyrad, tebuconazole, thiophanate-methyl, thiophanate-methyl, salamide, trifloxystrobin, and meconazole.

The composition comprising a compound of Formula 1 useful for seed treatment may further comprise bacteria, such as Bacillus pumilus (e.g., strain GB34) and Bacillus hardy (e.g., isolate 1582), a rhizobium inoculant/extender, isoflavones, and lipopolysaccharides.

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

The compounds of the present disclosure may be incorporated into a feed composition that is consumed by invertebrate pests or used in devices such as traps, feeding stations, etc. Such a feed composition may be in the form of a granule comprising (a) an active ingredient, i.e., a biologically effective amount of a compound of Formula 1 , an N -oxide or a salt thereof; (b) one or more food materials; optionally (c) an attractant, and optionally (d) one or more wetting agents. Of note are granules or feed compositions comprising between about 0.001%-5% active ingredient, about 40%-99% food material and/or attractant; and optionally about 0.05%-10% wetting agent, which are effective in controlling and combating soil invertebrate pests at very low application rates, particularly at doses of active ingredient that are lethal by ingestion rather than by direct contact. Some food materials can serve as both a food source and an attractant. Food materials include carbohydrates, proteins, and lipids. Examples of food materials are vegetable meals, sugars, starches, animal fats, vegetable oils, yeast extracts, and milk solids. Examples of attractants are flavor enhancers and flavors such as fruit or plant extracts, spices, or other animal or plant components, harbingers, or other agents known to attract target invertebrate pests. Examples of humectants (i.e., water retainers) are ethylene glycol and other polyols, glycerol, and sorbitol. Of note are bait compositions (and methods of using such bait compositions) for controlling and combating at least one invertebrate pest selected from the group consisting of ants, termites, and cockroaches. A device for controlling and combating invertebrate pests may comprise a feed composition of the present invention and a housing adapted to contain the feed composition, wherein the housing has at least one opening sized to allow the invertebrate pest to pass through the opening, allowing the invertebrate pest to access the feed composition from a location outside the housing, and wherein the housing is further adapted to be placed in or near a location where the invertebrate pest may or is known to move.

The compounds of the present disclosure may be administered without other adjuvants, but the most common administration is administration of a formulation comprising one or more active ingredients with suitable carriers, diluents and surfactants, and possibly in combination with food depending on the intended end use. One method of administration involves spraying an aqueous dispersion or refined oil solution of the compounds of the present disclosure. Combinations with spray oils, spray oil concentrates, viscosifiers, adjuvants, other solvents and piperonyl butoxide generally enhance the efficacy of the compound. For non-agricultural purposes, such sprays can be administered from spray containers such as cans, bottles or other containers, by means of a pump or by releasing it from a pressurized container such as a pressurized aerosol spray can. Such spray compositions can take a variety of forms, such as sprays, mists, foams, smoke or dust. Therefore, depending on the specific circumstances, such spray compositions may further include propellants, foaming agents, etc. It is worth noting that the spray composition comprises a biologically effective amount of the compound or composition disclosed herein and a carrier. One embodiment of such a spray composition comprises a biologically effective amount of the compound or composition disclosed herein and a propellant. Representative propellants include, but are not limited to, methane, ethane, propane, butane, isobutane, butene, pentane, isopentane, neopentane, pentene, hydrofluorocarbons, chlorofluorocarbons, dimethyl ether, and mixtures thereof. Of note are spray compositions for controlling and combating at least one invertebrate pest (and methods of using such spray compositions dispensed from a spray container), the at least one invertebrate pest selected from the group consisting of mosquitoes, gnats, gnats, deer flies, horse flies, wasps, wasps, hornets, ticks, spiders, ants, midges, etc., including alone or in combination.

One embodiment of the present disclosure relates to a method for controlling and combating invertebrate pests, which method comprises diluting the pesticidal composition of the present disclosure (a compound of formula 1 formulated with a surfactant, a solid diluent and a liquid diluent, or a formulated mixture of a compound of formula 1 and at least one other pesticidal agent) with water, and optionally adding an adjuvant to form a diluted composition, and contacting the invertebrate pests or their environment with an effective amount of the diluted composition.

Although the spray composition formed by diluting the pesticidal composition of the present invention at a sufficient concentration with water can provide sufficient control and efficacy against invertebrate pests, separately formulated adjuvant products can also be added to the spray tank mixture. Such additional adjuvants are generally referred to as "spray adjuvants" or "tank-mixed adjuvants" and include any material mixed in the spray tank to improve the performance of the pesticidal agent or change the physical properties of the spray mixture. The adjuvant can be a surfactant, an emulsifier, a petroleum-based crop oil, a crop-derived seed oil, an acidulant, a buffer, a thickener, or a defoamer. Adjuvants are used to enhance efficacy (e.g., bioavailability, adhesion, penetration, uniformity of coverage, and durability of protection) or to minimize or eliminate spray application problems associated with incompatibility, foaming, migration, evaporation, volatility, and degradation. For optimal performance, adjuvants are selected with respect to the characteristics of the active ingredient, the formulation, and the target (e.g., crop, insect pest).

Among spray adjuvants, oils (including crop oils, crop oil concentrates, vegetable oil concentrates, and methylated seed oil concentrates) are most commonly used to improve the efficacy of pesticidal agents, which may be achieved by promoting more uniform and consistent spray deposition. In cases where phytotoxicity that may be caused by oils or other water-immiscible liquids is important, spray compositions prepared from the compositions of the present disclosure will generally be free of oil-based spray adjuvants. However, in cases where phytotoxicity caused by oil-based spray adjuvants is not commercially important, spray compositions prepared from the compositions of the present invention may also contain oil-based spray adjuvants, which can potentially further increase control of invertebrate pests, as well as rainfastness.

Products identified as "crop oils" typically contain 95% to 98% paraffin or naphtha-based petroleum oils and 1% to 2% of one or more surfactants used as emulsifiers. Products identified as "crop oil concentrates" usually consist of 80% to 85% emulsifiable petroleum-based oils and 15% to 20% non-ionic surfactants. Products properly identified as "vegetable oil concentrates" usually consist of 80% to 85% vegetable oils (i.e., seed or fruit oils, most commonly from cotton, flaxseed, soybean or sunflower) and 15% to 20% non-ionic surfactants. Adjuvant performance can be improved by replacing vegetable oils with methyl esters of fatty acids, which are usually derived from vegetable oils. Examples of methylated seed oil concentrates include ^MSO® concentrate (UAP-Loveland Products, Inc.) and Premium MSO Methylated Spray Oil (Helena Chemical Company).

The amount of adjuvant added to the spray mixture is usually no more than about 2.5% by volume, and more usually the amount is from about 0.1% to about 1% by volume. The dosage of the adjuvant added to the spray mixture is usually between about 1 L and 5 L per hectare. Representative examples of spray adjuvants include: ^Adigor® (Syngenta) 47% methylated rapeseed oil in liquid hydrocarbons, ^Silwet® (Helena Chemical Company) polyether-modified heptamethyl trisiloxane, and ^Assist® (BASF) 17% surfactant blend in 83% paraffin-based mineral oil.

Non-agricultural applications include protecting animals from invertebrate parasitic pests by administering a parasiticidally effective (i.e., biologically effective) amount of a compound of the present disclosure (typically in the form of a composition formulated for veterinary use) to the animal to be protected, particularly a vertebrate, more particularly a warm-blooded vertebrate (e.g., a mammal or a bird) and most particularly a mammal. Therefore, of note is a method for protecting an animal comprising administering a parasiticidally effective amount of a compound of the present disclosure to the animal. As referred to in the present disclosure and claims, the terms "parasiticidal" and "parasiticidal" refer to observable effects on invertebrate parasitic pests to protect the animal from the pest. The parasiticidal effect is typically associated with reducing the presence or activity of target invertebrate parasitic pests. Such effects on pests include necrosis, death, slowed growth, reduced mobility or reduced ability to remain on or in the host animal, reduced feeding, and reproductive inhibition. Such effects on invertebrate parasitic pests control and combat (including preventing, reducing or eliminating) parasitic infestations or infections of animals. Examples of invertebrate parasitic pests that are controlled by administering a parasiticidally effective amount of the compounds disclosed herein to the protected animal include surface parasites (arthropods, acarines, etc.) and internal parasites (worms, such as nematodes, trematodes, tapeworms, acanthocephala, etc.). In particular, the compounds disclosed herein are effective against the following ectoparasites: flies, such as horn flies ( Haematobia (Lyperosia) irritans ), wall flies ( Stomoxys calcitrans ), blackflies ( Simulium species), tsetse flies ( Glossina species), head flies ( Hydrotaea irritans ), autumn house flies ( Musca autumnalis ), house flies ( Musca domestica ), Morellia simplex , horse flies (Taphidinium species), cow hide flies ( Hypoderma bovis ), vein flies ( Hypoderma lineatum ), silk green flies ( Lucilia sericata ), green-headed flies ( Lucilia cuprina ), flies ( Calliphora species), Protophormia species, Oestrus ovis , midges ( Culicoides species), Hippobosca equine , Gastrophilus instestinalis , Gastrophilus haemorrhoidalis , and Gastrophilus naslis ; lice, such as Bovicola (Damalinia) bovis , Bovicola equi , Haematopinus asini , Felicola subrostratus , Heterodoxus spiniger , Lignonathus setosus , and Trichodectes . canis ); ticks such as Psoroptes scabei ; mites such as Psoroptes scabei , Sarcoptes scabei , Chorioptes bovis , Demodex equi , Cheyletiella , Notoedres cati , Trombicula , and Otodectes cyanotis ; ticks such as Ixodes , Boophilus , Rhipicephalus , Amblyomma , Dermacentor , Hyalomma ) species and Haemaphysalis species; and fleas, such as the cat flea ( Ctenocephalides felis ) and the dog flea ( Ctenocephalides canis ).

Non-agricultural applications in the veterinary sector are by conventional means, such as enteral administration in the form of tablets, capsules, drinks, immersion products, granules, pastes, boluses, feeding procedures or suppositories; or parenteral administration such as by injection (including intramuscular injection, subcutaneous injection, intravenous injection, intraperitoneal injection) or implants; nasal administration; topical administration such as by dipping or soaking, spraying, washing, powder coating, or application to a small area of the animal and by articles containing the compounds or compositions of the present disclosure (such as collars, ear tags, tail bands, limb bands or leashes).

Typically, the parasiticidal composition according to the present disclosure comprises a mixture of a compound of Formula 1 , an N -oxide or salt thereof and one or more pharmaceutically or veterinarily acceptable carriers, the one or more pharmaceutically or veterinarily acceptable carriers comprising excipients and adjuvants selected according to standard procedures for the intended route of administration (e.g., oral, topical or parenteral administration, such as injection). In addition, a suitable carrier is selected based on compatibility with one or more active ingredients in the composition, including considerations such as stability relative to pH and moisture content. Therefore, it is noteworthy that the composition for protecting animals from invertebrate parasitic pests comprises a parasiticidally effective amount of the compound of the present disclosure and at least one carrier.

For parenteral administration including intravenous injection, intramuscular injection and subcutaneous injection, the compounds of the present disclosure can be formulated in the form of suspensions, solutions or emulsions in oily or aqueous vehicles and may contain adjuvants such as suspending agents, stabilizers and/or dispersants. Pharmaceutical compositions for injection include aqueous solutions of the active ingredient (e.g., salts of the active compound) in water-soluble form, preferably in a physiologically compatible buffer containing other excipients or adjuvants, as known in the art of pharmaceutical formulations.

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 may be formulated with binders/fillers known in the art to be suitable for oral administration compositions, such as sugars (e.g., lactose, sucrose, glycerol, The present invention relates to a kind of powdered plasticizer, for example, cellulose (e.g., cellulose glycol, sorbitol), starch (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, polyvinyl pyrrolidone). If necessary, lubricants (e.g., magnesium stearate), disintegrating agents (e.g., cross-linked polyvinyl pyrrolidone, agar, alginic acid) and dyes or pigments can be added. Pastes and gels also often contain a binder (eg, gum arabic, alginic acid, bentonite, cellulose, xanthan gum, colloidal magnesium aluminum silicate) to help keep the composition in contact with the oral cavity and prevent it from being expelled.

If 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. In addition to the parasiticidal active ingredient, such feed concentrate-containing compositions may also contain additives that promote animal health or growth, improve the quality of animal meat for slaughter or are otherwise useful for animal husbandry. Such additives may include, for example, vitamins, antibiotics, chemotherapy, bacteriostats, fungistats, anticoccidial agents and hormones.

The compounds of the present disclosure have been found to have good pharmacokinetic and pharmacodynamic properties, thereby providing systemic availability by oral administration and ingestion. Thus, after ingestion by the animal to be protected, the parasiticidally effective concentration of the compounds of the present disclosure in the bloodstream protects the treated animal from blood-sucking pests such as fleas, ticks and lice. Therefore, it is worth noting that the composition in a form for oral administration for protecting animals from invertebrate parasitic pests (i.e., in addition to a parasiticidally effective amount of the compounds of the present disclosure, also comprises one or more carriers selected from binders and fillers suitable for oral administration and feed concentrate carriers).

Formulations for topical administration typically take the form of powders, creams, suspensions, sprays, lotions, foams, pastes, aerosols, ointments, salves, or gels. More typically, topical formulations are water-soluble solutions, which may be in the form of concentrates for dilution prior to use. Parasiticide compositions suitable for topical administration typically comprise a compound of the present disclosure and one or more topically suitable carriers. When a parasiticidal composition is topically applied to the exterior of an animal as lines or dots (i.e., a "spot" treatment), the active ingredient migrates to the surface of the animal to cover most or all of its outer surface area. The treated animals are therefore particularly protected from invertebrate pests such as ticks, fleas and lice that feed on the animal's skin. Therefore, formulations for topical administration usually contain at least one organic solvent to facilitate the transport of the active ingredient across the animal's skin and/or penetration into the animal's epidermis. Solvents commonly used as carriers in such formulations include propylene glycol, wax, aromatic compounds, esters (such as isopropyl myristate), glycol ethers, and alcohols (such as ethanol and n-propanol).

The application rate required for effective control (i.e., the "biologically effective amount") will depend on factors such as the invertebrate species to be controlled, the life cycle of the pest, its life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, environmental humidity, temperature. Under normal circumstances, application rates of about 0.01 kg to 2 kg of active ingredient per hectare are sufficient for control and combating pests in agricultural ecosystems, but as low as 0.0001 kg/hectare may be sufficient, or as high as 8 kg/hectare may be required. For non-agricultural applications, effective use rates will be between about 1.0 mg/m2 and 50 mg/m2, but as low as 0.1 mg/m2 may be sufficient, or as high as 150 mg/m2 may be required. Those skilled in the art can readily determine the biologically effective amount required for a desired level of invertebrate pest control.

Typically for veterinary use, a compound of Formula 1 , its N -oxide or salt is administered in a parasiticidally effective amount to an animal to be protected from invertebrate parasitic pests. A parasiticidally 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 appreciate that the parasiticidally effective amount may vary with the various compounds and compositions disclosed herein, the desired parasiticidal effect and duration, the target invertebrate pest species, the animal to be protected, the mode of application, etc., and the amount required to achieve a particular result can be determined by simple experimentation.

For oral administration to warm-blooded animals, the daily dose of the compounds of the present disclosure is typically 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 the animal's body weight. For topical (e.g., epidermal) 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.

Recent advances in computer processing power have provided scientists with unprecedented opportunities to use computer simulation tools to predict and study potential adverse outcomes associated with xenobiotic exposures and the molecular basis of such events. Although current computational models cannot be used to completely replace all in vitro or in vivo experimental methods, they provide valuable tools to generate hypotheses, flag compounds of concern, and help prioritize and tailor chemicals for in vitro or in vivo studies.

Computational/predictive toxicology is a rapidly growing discipline that integrates information and data from multiple sources to develop mathematical and computer-based models to better understand and predict the interactions of chemical agents and biological organisms at many scales (e.g., population, individual, cellular, and molecular) and can be considered to include two broad areas: (1) First principles development and application of two-dimensional (2D) models (e.g., structural units that drive facile chemical reactivity (Wijeyesakere, SJ et al. Development of a Profiler for Facile Chemical Reactivity Using the Open-Source Konstanz Information Miner [Development of a Profiler for Facile Chemical Reactivity Using the Open-Source Konstanz Information Miner]. Appl. Vitr. Toxicol. [Applied in vitro toxicology], 4 , 202-213, 2018). Alternatively, quantitative structure-activity relationship techniques (QSAR) such as trend analysis can be performed to predict dosing for biological outcomes of interest if experimental data from similar molecules are available (e.g., predicting the choleretic potential of a series of related organophosphorus compounds (Makhaeva, GF et al. Esterase profiles of organophosphorus compounds in vitro predict their behavior in vivo). Chem. Biol. Interact. , 259 , 332-342, 2016). Makhaeva, GF et al. Kinetics and mechanism of inhibition of serine esterases by fluorinated carbethoxy 1-aminophosphonates [Kinetics and mechanisms of inhibition of serine esterase by fluorinated ethoxy-1-aminophosphonates]. Dokl. Biochem. Biophys. [Biochemical and Biophysical Reports], 451 , 203-206, 2013). (2) Use of “big data” approaches that curate all available information about a particular outcome/mode of action (e.g., predictive models for identifying mitochondrial inhibitors (Wijeyesakere, SJ et al. Hybrid Machine-Learning/SMARTS Profiling Model for Mitochondrial Inhibition]. Appl. Vitr. Toxicol. [Applied in vitro Toxicology], 5 , 196-204, 2019) or those that are likely to interact with defined neuronal receptors (Wijeyesakere, SJ et al. Prediction of cholinergic compounds by machine-learning [Prediction of cholinergic compounds by machine-learning]. Comput. Toxicol. [Comput. Toxicol.], 13 , 100119, 2020); and extending these 2D assessments to include 3D techniques such as docking and molecular dynamics (MD) simulations to further investigate the molecular basis of the interaction between toxicants and known/putative biological targets (Wang, Y. et al. Mixed inhibition of adenosine deaminase activity by 1,3-dinitrobenzene: A Model for understanding cell-selective neurotoxicity in chemically-induced energy deprivation syndromes in brain [1,3-dinitrobenzene mixed inhibition of adenosine deaminase activity: A Model for understanding cell-selective neurotoxicity in chemically-induced energy deprivation syndromes in brain]. Toxicol. Sci. [Toxicology], 125 , 509-521, 2012; Gonzalez, TL et al. Metabolites of n-Butylparaben and iso-Butylparaben Exhibit Estrogenic Properties in MCF-7 and T47D Human Breast Cancer Cell Lines. Toxicol. Sci. , 164 , 50-59018, 2018).

Specific compounds of Formula 1 prepared by the methods and variations described in Schemes 1-10 and Synthetic Examples 1-2 above are shown in Index Table A below. For mass spectrometry (MS) data, the reported values are the molecular weights of the most isotopically abundant parent ion (M+1) formed by the addition of H ⁺ (molecular weight 1) to the molecule as observed by mass spectrometry using atmospheric pressure chemical ionization (AP ⁺ ). Melting point data (MP) are reported as a temperature range. Interstellar molecular ion peaks (e.g., M+2 or M+4) that occur with compounds containing multiple halogens are not reported.

The following abbreviations are used in the Index Tables that follow: Cmpd means compound, t is tertiary, c is cyclo, Me is methyl, Et is ethyl, Pr is propyl, i -Pr is isopropyl, Bu is butyl, c -Pr is cyclopropyl, c -Pn is cyclopentyl, c -Hx is cyclohexyl, t -Bu is tertiary butyl, Ph is phenyl, OMe is methoxy, SMe is methylthio, and _SO2Me means methylsulfonyl. Wavy lines in structure fragments indicate the points of attachment of the fragment to the rest of the molecule. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which synthetic instance the compound was prepared. Index Table A Compound No. Compound structure M+1 mp (°C) 1 321.0 2 308.1 3 324.1 4 340.0 5 356.14 6 372 7 322.26 8 326.23 9 338.1 10 308.1 11 321.2 12 292.2 13 322.1 14 310.2 15 324.3 16 324.3 17 350.4 18 352.4 19 348.3 20 364.4 twenty one 334.4 twenty two 352.4 twenty three 360.4 twenty four 368.4 25 334.4 26 376.4 27 79-81 28 197-200 29 135-137 30 370.2 31 386.4 32 170-173 33 136-139 34 115-118 35 72-75 36 93-96° 37 112-115 38 107-110° 39 203-206 40 110-113 41 85-88 42 115-118 43 127-130 44 86-89 45 177-180 46 90-92 47 140-142 48 112-114°C 49 108-110°C 50 100-102°C 51 110-112°C 52 78-80°C 53 344.1 54 312.1 55 93-95 56 156-158 57 355.1 58 72-74 59 342.1 60 352.2 61 340.2 62 336.2 63 78-80 64 92-94 65 98-100 66 68-70 67 312.2 68 324.1 69 116-118 70 130-132 71 84-86 72 77-79 73 76-79 74 127-130 75 77-80 76 137-140 77 67-70 78 326.2 79 364.3 80 346.2 81 326.2 82 310.2 83 326.2 84 356.3 85 342.2 86 344.2 87 338.3 88 354.2 89 142-145 90 91-94 91 356.2 92 338.2 93 340.2 94 64-66 95 81-83 96 91-94 97 117-120 98 308.2 99 322.3 100 373.1 101 378.3 102 100-102 103 90-92 104 184-186 105 338.3 106 382.3 107 402.3 108 330.2 109 330.2 110 150-153 111 139-142 112 320.2 113 147-150°C 114 72-75°C 115 123-124°C 116 112-115°C 117 76-78°C 118 134-136°C 119 85-87°C 120 160-163°C 121 85-87°C 122 110-113°C 123 407.6 124 147-149 125 335.4 126 145-147°C 127 95-98°C 128 84-87°C 129 334.3 130 343.35 131 146-148 132 317.4 133 116-118 134 111-113 135 113-115 136 158-160 137 358.2 138 184-186 139 92-94 140 190-192 141 102-105 142 103-106 143 322.2 144 129-131 145 344.2 146 322.3 147 80-83 148 326.1 149 344.2 150 95-97 151 87-90 152 100-102 153 107-110 154 114-117 155 143-146 156 83-86 157 93-96 158 328.6 159 336.3 160 97-100 161 130-132 162 96-99 163 72-75 164 85-87 165 121-124 166 336.3 167 115-118 168 95-97 169 130-133 170 82-85 171 95-98 172 356.2 173 325.1 174 337.2 175 94-97°C 176 306.1 177 172-175 178 163-166 179 175-178 180 100-102 181 319.9 182 338 183 300 184 258.1 185 247.1 186 262.1 187 319.9 188 338 189 300.1 190 256.1 191 247.2 192 266.2 193 224.2 194 282.3 195 262.2 196 236.2 197 318 198 338 199 300 200 256.1 201 247.1 202 282.2 203 280.2 204 300.3 205 300.2 206 282.2 207 264.2 208 264.3 209 290.3 210 288.2 211 288.2 212 370.2 213 370.1 214 306.2 215 306.2 216 326.3 217 326.3 218 290.2 219 354.4 220 362.5 221 370.4 222 350.5 223 358.3 224 366.5 225 382.6 226 366.5 227 374.4 228 336.2 229 332.5 230 344.4 231 348.3 232 360.4 233 336.3 234 318.3 235 352.3

The following tests demonstrate the control efficacy of the compounds of the present disclosure against specific pests. "Control efficacy" means inhibition of development (including mortality) of invertebrate pests resulting in a significant reduction in feeding. However, the pest control protection provided by the compounds is not limited to these species. See Index Table A for compound descriptions. Biological Examples

The following tests demonstrate the control efficacy of the compounds of the present disclosure against specific pests. "Control efficacy" means inhibition of development (including mortality) of invertebrate pests resulting in a significant reduction in feeding. However, the pest control protection provided by the compounds is not limited to these species. See Index Table A for compound descriptions. Formulations and spraying methodologies for Tests A-E

The test compounds were formulated using a solution containing 10% acetone, 90% water, and 300 ppm Activator 90® nonionic surfactant (Loveland Products, Loveland, Colorado, USA). The formulated compounds were applied as 1 mL of liquid via an atomizing nozzle positioned 1.27 cm (0.5 in) above the top of each test cell. The test compounds were sprayed at the indicated rates, and each test was repeated three times. Test A

To evaluate control of corn planthoppers (Coleoptera: corn cicada) by contact and/or systemic means, the test unit consisted of small open containers with 3-4 day old corn (maize) plants inside. White sand was added to the top of the soil before application of the test compound.

The test compounds were formulated as described above and sprayed at 250, 50, 10, and 2 ppm in triplicate. After spraying the formulated test compounds, the test units were allowed to dry for 1 hour before being reinfested with approximately 15-20 nymphs (18 to 21 days old). A black screen lid was placed on top of each test unit, and the test units were maintained in a growth chamber at 22°C to 24°C and 50%-70% relative humidity for 6 days. Each test unit was then visually assessed for insect mortality.

Of the compounds of Formula 1 tested at 250 ppm, the following resulted in at least 80% mortality: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 12, 14, 18, 19, 20, 21, 29, 32, 33, 48, 49, 50, 52, 53, 54, 58, 60, 61, 62, 63, 64, 65, 66, 67, 71, 72, 79, 80 0, 82, 83, 84, 86, 94, 95, 111, 116, 117, 128, 129, 130, 141, 151, 152, 159, 160, 162, 163, 164, 183, 186, 207, 208, 213, 219, 221, 225, 226, 228, 229, 231, 233, 234, 235.

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

To evaluate control of green peach aphid by contact and/or systemic means, the test unit consisted of a small open container with 12 to 15 day old radish plants inside. Prior to compound application, each test unit was pre-infested (cut leaf method) by placing 30-40 aphids from a leaf cut from a culture plant on a leaf of the test plant. As the leaf was dehydrated, the aphids moved on the test plant. After pre-infestation, the soil of the test unit was covered with a layer of sand.

The test compounds were formulated as described above and sprayed at 250, 50 and 10 ppm, repeated three times. After spraying the formulated test compounds, each test unit was allowed to dry for 1 hour, and then a black screen cover was placed on top. The test units were kept in a growth chamber at 19°C-21°C and 50%-70% relative humidity for 6 days. Each test unit was then visually assessed for insect mortality.

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

Of the compounds of formula 1 tested at 50 ppm, the following caused at least 80% mortality: 18, 21, 83, 94, 117, 128, 129, 130, 141, 219, 228, 234. Test D

To evaluate control of cotton aphid by contact and/or systemic means, the test unit consisted of small open containers with 5-day-old okra plants inside. This was pre-infested with 30-40 insects on one leaf according to the cut leaf method, and the soil of the test unit was covered with a layer of sand.

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

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

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

To evaluate the control of sweet potato whitefly (Bevacizole tabaci) by contact and/or systemic means, the test unit consisted of small open containers with 8-9 day old soybean plants inside. Prior to spray application, the two cotyledons and the simple leaf were removed from the plants, leaving one true leaf for analysis. Adult whiteflies were allowed to lay eggs on the plants, and then they were removed from the test unit. Soybean plants infested with at least 15 eggs were submitted for spray testing.

The test compound was formulated and sprayed at 50 ppm. After spraying, the test unit was allowed to dry for 1 hour. The cylinder was then removed and the unit was placed in a growth chamber and maintained at 28°C and 50%-70% relative humidity for 13 days. Each test unit was then visually assessed for insect mortality.

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

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

For the evaluation of control of Plutella xylostella by contact and/or systemic means, each test unit consisted of a small open container with 10 to 12 day old mustard plants inside.

Test compounds were formulated as described above and sprayed at 250 ppm in three replicates. After spraying, the test units were allowed to dry for 1 hour before infesting them with 30-50 newly hatched larvae. A black screen lid was placed on top of each container. The test units were maintained in a growth chamber at 24°C-25°C and 70% relative humidity for six days. Plant feeding damage was then assessed visually based on leaves consumed, and larval mortality was assessed.

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): 3, 46, 58, 67, 75, 77, 78, 82, 83, 93, 97, 98, 99, 100, 112, 121, 142, 145, 148, 158, 160.

without

without

without

Claims (23)

A compound selected from Formula 1 , its N -oxide or salt, 1wherein L is CR ⁵ R ⁶ , CR ⁵ R ⁶ CR ⁵ R ⁶ , OCR ⁵ R ⁶ , CR ⁵ R ⁶ O; CR ⁵ R ⁶ NR ⁷ , NR ⁷ CR ⁵ R ⁶ , C(=E)NR ⁷ , NR ⁷ C(=E), C(=E) CR ⁵ R ⁶ , CR ⁵ R ⁶ C(=E), C(=CR ⁵ R ⁶ ), CR ⁵ =CR ⁶ or C(=E); ; E is O, S or NR ⁸ ; m is 0, 1, 2, 3, 4, or 5; each R ¹ is independently halogen, cyano, nitro, hydroxyl, SF ₅ , C(O)NH ₂ , C(O)NR ¹⁰ R ¹¹ , C(=NR ¹³ )NR ¹⁰ R ¹¹ , C(=NR ¹³ )R ^{R 14} , OC(O)R ¹⁴ , NR ¹⁰ R ¹¹ , NR ¹³ C(O)R ¹⁴ , C(O)R ¹⁴ , S(O) _n R ¹⁴ , OS(O) _n R ¹⁴ , Si(R ¹⁴ ) ₃ , OSi(R ¹⁴ ) ₃ or MQ ^a ; or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ cycloalkoxy, which is unsubstituted or substituted by at least one R ^x ; or two R on adjacent ring atoms ¹ substituents together with the carbon atoms to which they are attached form a 4 to 7 membered ring containing carbon atoms and up to 3 heteroatom ring members independently selected from up to 2 oxygen atoms, one sulfur atom and up to 3 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O) or S(O) ₂ , said ring being unsubstituted or substituted with at least one R ^x ; each R ² , R ³ , R ⁴ is independently hydrogen, halogen, cyano, nitro, hydroxyl, SF ₅ , C(O)H, C(O)NH 2 , C(O)NR 10 R ₁₁ , C(=NR 13 )NR ¹⁰ R ¹¹ , C(=NR ¹³ )NR ¹⁰ R ¹¹ , C(=NR or C ^{1 -C 6 alkyl} , C 3 ^-C 6 cycloalkyl, ^C 1 -C ⁶ alkoxy, ^C 3 _-C ^{6 cycloalkoxy} , C ² -C ₆ alkenyl _or C ₂ -C ₆ alkynyl, which is unsubstituted or substituted by at least _one R ^x ; or _two substituents _{on adjacent} ring atoms ^{(R 2 and R 3, or R 3 and R 4 )} _{are substituted} ^{or replaced} _{by at least one} ^{R x} _; ) together with the carbon atoms to which they are attached form a 4 to 7 membered ring containing ring members selected from carbon atoms and up to 3 heteroatoms independently selected from up to 2 oxygen atoms, one sulfur atom and up to 3 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are selected from S, S(O) or S(O) ₂ , said ring being unsubstituted or substituted with at least one R ^x ; M is a direct bond, O, S, S(O), S(O) ₂ or NR ⁹ ; R ⁵ and R ⁶ are independently hydrogen, hydroxyl, halogen, cyano, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ halogenated alkyl, C ₁ -C 6 R ₅ and R ⁶ _each attached to the same carbon atom together with the carbon atom to _which they are attached form a _{3- to 7 -membered ring containing ring members selected from carbon atoms and up to 3 heteroatoms independently} selected from one oxygen atom, ^one sulfur atom and up to 3 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are selected from S, S(O) or S(O) ₂ , said ring being unsubstituted or substituted with at least one R ^x ; or in the case of CR ⁵ R ⁶ CR ⁵ R ⁶ , each R ⁵ and R 6 ^{R 15} is attached to each of the first and second adjacent carbon atoms and can form, together with the carbon atoms to which they are attached, a 3 to 7 membered ring containing ring members selected from carbon atoms and up to 3 heteroatoms, the heteroatoms being independently selected from one oxygen atom, one sulfur atom and up to 3 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are selected from S, S(O) or S(O) ₂ , the ring being unsubstituted or substituted with at least one R ^x ; each R ⁷ is independently H, C(O)R ¹⁵ or S(O) ₂ R ¹⁵ or Q ^b ; or C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl or C ₂ -C each R ⁸ is independently NR ¹⁰ R ¹¹ , OR ¹² , C(═NR ¹³ ₎ R 14 , C(O)NR 10 R 11 , C(O)R ¹⁴ or S(O) _n R ¹⁴ ; or ^phenyl , C ¹ -C 6 alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, each of which is unsubstituted or substituted by at least one R ^x ; each R ⁹ is independently H, NR 10 R ¹¹ , OR 12 , C(═NR _{13 )} R ¹⁴ , C(O)NR ¹⁰ R ¹¹ , C(O ^{)R 14} _or S(O) n R ¹⁴ ; or phenyl, C 1 -C ⁶ alkyl, C ^{3 -C 6} cycloalkyl, C 2 -C ⁶ alkenyl or C ₂ -C ₆ alkynyl, each of which is unsubstituted or substituted _{by at} least one R x R ^x is independently halogen, cyano, nitro, hydroxyl, C ₁ -C ₆ alkyl, C ₂ ^-C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ halogenated alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halogenated cycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ halogenated alkoxy, C ₃ -C ₆ cycloalkoxy, C _{3 -C 6} halogenated cycloalkoxy, C(O)NH ₂ , _C (O)NR ₁₀ R ₁₁ , C( ^{═NR 13} ₎ R ₁₄ ^, OC(O ⁾ R ¹⁴ , NR ¹⁴ R ¹⁰ R ¹¹ , NR ¹⁴ C(O)R ¹⁴ , C(O)R ¹⁴ , S(O) _n R ¹⁴ , OS(O) _n R ¹⁴ , Si(R ¹⁴ ) ₃ , OSi(R ¹⁴ ) ₃ or Q ^b ; each R ¹⁰ is independently C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ halogenated alkyl, C 2 -C 6 alkenyl or C _{2 -C 6} alkynyl, C(O)R ¹⁵ or S(O) ₂ R ¹⁵ ; or phenyl or a 5- or 6-membered heterocyclic aromatic ring, each of which is unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C 3 -C 6 cycloalkyl, C 1 -C ₆ halogenated alkyl, C 2 -C 6 alkenyl or C _{2 -C 6} alkynyl, -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; each R ¹¹ is independently H, C ₁ -C ₆ alkyl or C ₁ -C ₄ haloalkyl; or R ¹⁰ and R ¹¹ together with the nitrogen atom to which they are attached form a 3 to 7 membered ring containing ring members selected from carbon atoms and up to 3 heteroatoms independently selected from one oxygen atom, one sulfur atom and up to 3 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring member is selected from S, S(O) or S(O) ₂ , the ring is unsubstituted or substituted by at least one substituent independently selected from the following group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ halogenated alkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ halogenated alkoxy; each R ¹² is independently H, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl or C ₁ -C ₄ halogenated alkyl; or phenyl, which is unsubstituted or substituted by at least one substituent independently selected from the following group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ halogenated alkyl, C ₁ -C each R ¹³ is independently H; OR ¹⁶ , S(O) _n R ¹⁷ , C(O)OR ¹⁷ , C(O)R ¹⁷ or NHR ¹⁸ ; each R ¹⁴ is independently H; or C _{1 -C 6} alkyl _, C ₃ -C ₆ cycloalkyl, _{C 2} -C ₆ alkenyl or C ₂ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ cycloalkoxy, each of which is unsubstituted or substituted by at least one halogen, cyano or nitro; or C(O)OR ¹⁷ , C(O)NR ²² R ²³ , NR ²² R ²³ , NR ²⁴ C(O)R ¹⁷ , C(O)R ¹⁷ or Q ^b ; each R ^{R 15} is independently C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy or NR ²² R ²³ ; or phenyl or a 5- or 6-membered heterocyclic aromatic ring, each of which is unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; each R ¹⁶ is independently C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C (O) R ¹⁹ , S (O) _n ^R20 or Q ^b ; each R ¹⁷ is independently C ₁ -C ₄ alkyl or C ₁ -C ₄ halogenated alkyl; R ¹⁸ is C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ halogenated alkyl, C(O)R ¹⁹ or C(O)OR ²¹ ; or phenyl, which is unsubstituted or substituted with at least one substituent independently selected from the following group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ halogenated alkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ halogenated alkoxy; each R ¹⁹ is independently C ₁ -C ₄ alkyl, C ₁ -C ₄ halogenated alkyl, C ₃ -C C 1 -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C _{6 cycloalkyl, C 3 -C 6} halocycloalkyl, C ₃ -C 6 cycloalkylalkyl or C 3 -C ₆ halocycloalkylalkyl; or phenyl which is unsubstituted or substituted by at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; each R ²⁰ is independently C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₃ -C ₆ cycloalkylalkyl or C ₃ -C 6 halocycloalkylalkyl; or phenyl, which is unsubstituted or substituted by at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C _{6 cycloalkyl} , C 1 -C ₄ halogenated alkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ halogenated alkoxy; each R ²¹ is independently C _{1 -C 4} alkyl, C ₁ -C ₄ halogenated alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halogenated cycloalkyl, C ₃ -C ₆ cycloalkylalkyl or C ₃ -C or phenyl, which is unsubstituted or substituted by at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C _{6 cycloalkyl} , C 1 -C ₄ halogenated alkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ halogenated alkoxy; each R ²² is independently H, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ halogenated alkyl, C _{2 -C 6} alkenyl or C ₂ -C ₆ alkynyl, C(O)R ²⁵ or S(O) ₂ R ²⁵ or phenyl or a 5- or 6-membered heterocyclic aromatic ring, each of which is unsubstituted or substituted by at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ halogenated alkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ halogenated alkoxy; each R ²³ is independently H, C ₁ -C ₆ alkyl or C ₁ -C ₄ halogenated alkyl; or R ²² and R ²³ together with the nitrogen atom to which they are attached form a 3 to 7 membered ring containing ring members selected from carbon atoms and up to 2 heteroatoms independently selected from one oxygen atom, one sulfur atom and up to 2 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are selected from S, S(O) or S(O) ₂ , said ring being unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ halogenated alkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ halogenated alkoxy; each R ^{R 24} is independently H or C ₁ -C ₄ alkyl; each R ²⁵ is independently C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₆ haloalkoxy; or phenyl or a 5- or 6-membered heterocyclic aromatic ring, each of which is unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; each Q ^a is independently phenyl, a 5- or 6-membered heterocyclic aromatic ring or a 3- to 6-membered heterocyclic non-aromatic ring, each ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from one oxygen atom, one sulfur atom and up to 4 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O) or S(O) ₂ , each ring being unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ halogenated alkyl, C 1 -C 4 alkoxy and C ₁ -C ₄ alkyl radicals. _each ^Qb is independently phenyl, a 5- or ₆ -membered heterocyclic aromatic ring or a 3- to 6-membered heterocyclic non-aromatic ring, each ring containing ring members selected from carbon atoms and up to 4 heteroatoms, the heteroatoms being independently selected from one oxygen atom, one sulfur atom and up to 4 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O) or S(O) ₂ , each ring being unsubstituted or substituted with at least one substituent independently selected from the following group consisting of halogen, cyano, nitro, _C1 - _C4 alkyl, _C3 - _C6 cycloalkyl, _C1 -C _and each n is independently 0, 1 or 2; provided that when R ² , R ³ and R ⁴ are H and L is CH(OH), R ₁ is not _{3 -} trifluoromethyl; and when L is C(=O) _NR ⁷ wherein the nitrogen is attached to a benzene ring, at least one of R ² , R ³ or ^{R 4} is not H. The compound as described in claim 1, wherein L is CR ⁵ R ⁶ . The compound as described in claim 1, wherein L is CR ⁵ R ⁶ CR ⁵ R ⁶ . The compound as described in claim 1, wherein L is OCR ⁵ R ⁶ . The compound as described in claim 1, wherein L is CR ⁵ R ⁶ O. The compound as described in claim 1, wherein L is CR ⁵ R ⁶ NR ⁷ . The compound as described in claim 1, wherein L is NR ⁷ CR ⁵ R ⁶ . The compound as described in claim 1, wherein L is C(=E)NR ⁷ . The compound as described in claim 1, wherein L is NR ⁷ C(=E). The compound as described in claim 1, wherein L is C(=E)CR ⁵ R ⁶ . The compound as described in claim 1, wherein L is CR ⁵ R ⁶ C(=E). The compound as described in claim 1, wherein L is C(=CR ⁵ R ⁶ ). The compound as described in claim 1, wherein L is CR ⁵ ═CR ⁶ . The compound as described in claim 1, wherein L is C(=E). The compound as described in any one of claims 1-14, wherein E is O or S. The compound as described in claim 1-15, wherein R ¹ is halogen, cyano, nitro, hydroxyl, SF ₅ , C(O)NH ₂ , C(O)NR ¹⁰ R ¹¹ , C(=NR ¹³ )NR ¹⁰ R ¹¹ , C(=NR ¹³ )R ¹⁴ , OC(O)R ¹⁴ , NR ¹⁰ R ¹¹ , NR ¹³ C(O)R ¹⁴ , C(O)R ¹⁴ , S(O) _n R ¹⁴ , OS(O) _n R ¹⁴ , Si(R ¹⁴ ) ₃ , OSi(R ¹⁴ ) ₃ or MQ ^a ; or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy or C ₃ -C ₆ -cycloalkoxy, which is unsubstituted or substituted with at least one R ^x . A compound as described in any one of claims 1-15, wherein m is 0, 1 or 2. A compound as described in claim 1, wherein the compound is selected from the following group, which consists of the following items: N-(7-methyl[1,2,4]triazolo[1,5-a]pyridin-5-yl)-4-(trifluoromethyl)benzamide, 7-methyl-5-[[4-(trifluoromethyl)phenyl]methoxy][1,2,4]triazolo[1,5-a]pyridine, (7-methyl[1,2,4]triazolo[1,5-a]pyridin-5-yl)[4-(trifluoromethoxy)phenyl]methanone, 5-[fluoro[4-(trifluoromethoxy)phenyl]methyl]-7-methyl[1,2,4]triazolo[1,5-a]pyridine, 5-[methoxy[4-(trifluoromethoxy)phenyl]methyl]-7-methyl[1,2,4]triazolo[1,5-a]pyridine, 7-methyl-5-[[4-(trifluoromethoxy)phenyl]methyl][1,2,4]triazolo[1,5-a]pyridine, 7-methyl-5-[[4-(trifluoromethyl)phenyl]methyl][1,2,4]triazolo[1,5-a]pyridine, 5-[fluoro[4-(trifluoromethyl)phenyl]methyl]-7-methyl[1,2,4]triazolo[1,5-a]pyridine, (6-cyclopropyl-3aH-inden-4-yl)(4-(trifluoromethoxy)phenyl)methanone, 5-(fluoro(4-(trifluoromethyl)phenyl)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-(3-fluoro-4-(trifluoromethyl)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-(3-fluoro-4-(trifluoromethoxy)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-(fluoro(3-fluoro-4-(trifluoromethoxy)phenyl)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 1-(7-cyclopropyl-[1,2,4]triazolo[1,5-a]pyridine-5-yl)-1-(4-(trifluoromethoxy)phenyl)ethan-1-ol, 5-(fluoro(4-(trifluoromethoxy)phenyl)methyl)-7-methoxy-[1,2,4]triazolo[1,5-a]pyridine, 5-(2-fluoro-4-(trifluoromethyl)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-((2-fluoro-4-(trifluoromethoxy)phenyl)(methoxy)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 5-(fluoro(2-fluoro-4-(trifluoromethoxy)phenyl)methyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 7-iodo-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-isopropyl-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-(difluoromethyl)-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-cyclopropyl-5-(4-(trifluoromethyl)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 5-(2-fluoro-4-(trifluoromethoxy)benzyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyridine, 7-bromo-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-cyclopropyl-6-(2-(3-(trifluoromethyl)phenyl)cyclopropyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-cyclopropyl-5-((3-fluoro-4-(trifluoromethyl)phenyl)(methoxy)methyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-cyclopropyl-5-(fluoro(3-fluoro-4-(trifluoromethoxy)phenyl)methyl)-[1,2,4]triazolo[1,5-a]pyridine, 7-cyclopropyl-5-(4-(trifluoromethoxy)benzyl)-[1,2,4]triazolo[1,5-a]pyridine, and 7-cyclopropyl-5-(fluoro(4-(trifluoromethoxy)phenyl)methyl)-[1,2,4]triazolo[1,5-a]pyridine, and any combination of the foregoing compounds. A composition comprising a compound as claimed in any of the preceding claims and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent, wherein the composition further comprises at least one additional biologically active compound or agent as necessary. A composition comprising α-[3-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5- a ]pyridine-5-methanol having the following structure: and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent, the composition optionally further comprising at least one additional biologically active compound or pharmaceutical agent. The composition of claim 19 or 20, wherein the at least one additional biologically active compound or agent is selected from the following group, which is composed of the following items: abamectin, acetothiocarb, cypermethrin, acetamiprid, acetamiprid, fluazifop, sulfamethoxam, amitraz, avermectin, azadirachtin, azoxystrobin, chlorfenapyr, propylthiocarb, chlorfenapyr, bifenthrin, bifenazate, diflunisal, borate, bromobendan, phenthiocarb, carbaryl, chlorpyrifos, chlorpyrifos, d-trans-chlorpropthrin, Chlorpyrifos, chlorpyrifos-methyl, cyclohexidine, tetramid, clothianidin, bromocyanamide, cyclobromocyanamide, triflupyramide, cypermethrin, epoxyfenoxam, ethozolin, butyric acid, cyfluthrin, high-efficiency cyfluthrin, cyhalothrin, cyhalothrin, high-efficiency cyhalothrin, cyhalothrin, high-efficiency cyhalothrin Permethrin, cyhalothrin, cypermethrin, cis-cypermethrin, ζ-cypermethrin, cyprofen, cyfluthrin, deltamethrin, difenac, diazofuron, dichlorobenzamide, dieldrin, fluazifop, dimethoate, tetrafluthrin, cypermethrin, dimethoate, dimethoate, dimethomorph , emamectin, endosulfan, cypermethrin, ethoprolin, ethosulfan, quinamectin, fenbutin, cypermethrin, bisthiocarb, fenoxycarb, cyfluthrin, cypermethrin, flumethrin, fluazifop, flumetol, flumetol, flumetol, flufenamid, flumetol, flumetol Dimethoate, fluchloramid, flucythrinate, flumethoate, flufluanid, flufenamid, flutolanil, flupentixol, fluopyram, flufenamid, flupyradanil, flupyradan, fluvalinate, fluvalinate, flutolanil, flutoxamide, flufenamid, fluthiophene, flutosan, flutoxanil, flutosan, flutoxamide, flutothion, flutosan, flutoxanil, flutosan, flutoxamide ... Chlorfenapyr, cefotaxime, fluazifop, thiophanate-methyl, fluazifop, methoxyfen-ethyl, pyrimidine, indazole (N-(1-methylcyclopropyl)-2-(3-pyridyl)-2H-indazole-4-carboxamide), indomethacin, insecticide soap, isopropylamine, isothiocarb , κ-tefluthrin, methoprene, cyfluthrin, marasmustine, cyfluthrin, cyfluthrin, metaldehyde, methamidophos, chlorpyrifos, methiocarb, cyfluthrin, methoprene, methoxychlor, methoxychlor, chloranil, chloranil, monocrotophos, monofluthrin, cyfluthrin, niacin, N -[1,1-dimethyl-2-(methylthio)ethyl]-7-fluoro-2-(3-pyridyl) -2H -indazole-4-carboxamide, N -[1,1-dimethyl-2-(methylsulfinyl)ethyl]-7-fluoro-2-(3-pyridyl) -2H -indazole-4-carboxamide, N -[1,1-dimethyl-2-(methylsulfonyl)ethyl]-7-fluoro-2-(3-pyridyl) -2H -indazole-4-carboxamide, N-(1-methylcyclopropyl)-2-(3-pyridyl)-2H-indazole-4-carboxamide, N -[1-(difluoromethyl)cyclopropyl]-2-(3-pyridyl) -2H -Indazole-4-carboxamide, nitenpyram, nitrobenzene, fluazifop, noviflumuron, cypermethrin, chlorpyrifos, parathion, methyl parathion, permethrin, phorate, phosphamidon, phosmet, pirimicarb, profenofos, profluthrin, cyfluthrin, pyrifos, pymetrozine, pyrifos Afenamide, pyrethrin (pyrethrin), cypermethrin, pyraclostrobin, pyrimethamine, pyraclostrobin, pyriproxyfen, rotenone, ryanodine, flucythrinate, dispirothrin, ethyl styracidin, styracidin, spirothiazolin, spirothiazolin, spiromethoxazole ... Hydrazide, pyraclostrobin, flubendiamide, tefluthrin, κ-tefluthrin, terbufos, tetrachlorvinphos, cypermethrin, tetrafluthrin, tetrazolam, thiamethoxam, thiocarb, cypermethrin, thiocarb, sulfamethoxam, thiocarb, thiosulfuron, cypermethrin, tetracycline, tralomethrin, trichlorfon, trifloxystrobin, trifloxystrobin Cyclomethicone, trifluanid, cypermethrin, chlorpyrifos, Bacillus sphaericus, Bacillus thuringiensis delta-endotoxin, insect pathogenic bacteria, insect pathogenic viruses and insect pathogenic fungi, plant essences including synthetic extracts and unrefined oils, RNA interference-mediated target inhibitors, thiocarbamide, and trifluanid. A method for controlling and combating invertebrate pests, the method comprising contacting the invertebrate pests or their environment with a biologically effective amount of a compound or composition as described in any one of claims 1 to 21. A treated seed comprising a compound or composition as described in any one of claims 1 to 21 in an amount from about 0.0001% to 1% by weight of the seed before treatment.