Pest control composition and pest control method

Abstract

[0003] Embodiments of the present disclosure relate to pest control compositions comprising a pyrone compound in combination with a pyrethroid compound, a neonicotinoid compound, an organophosphate compound, and / or an enzyme inhibitor. The present disclosure also provides methods for producing the pest control compositions of the present disclosure, and methods for controlling pests, such as insects, arachnids, and larvae, using the pest control compositions of the present disclosure.

Description

[Technical Field]

[0001] The present disclosure relates to compositions and methods for controlling pests. More specifically, the present disclosure relates to compositions comprising a pyrone compound, a pyrethroid compound, a neonicotinoid compound, an organophosphate compound, an enzyme inhibitor, or a combination thereof, methods for making the compositions, and methods for controlling and / or killing pests, such as insects, arachnids, and larvae, using the compositions. [Background technology]

[0002] Synthetic insecticides have played a vital role in eradicating mosquito populations worldwide. Insecticide resistance was first reported scientifically in 1914 and has gradually become more widely recognized. Currently, over 500 species of insects and mites are resistant to pesticides, posing a major threat to the future success of pest control. There are several definitions of insecticide resistance. According to the World Health Organization, insecticide resistance is defined as "the development of the ability of certain strains of insects, in a normal population of the same species, to resist doses of a poison that are lethal to the majority of insects." Summary of the Invention [Means for solving the problem]

[0003] FIELD OF THE DISCLOSURE This disclosure relates generally to compositions formulated for use as pesticides to kill, control, suppress, repel or mitigate pests such as insects, arachnids, larvae, and the like.

[0004] Thus, some embodiments provided herein relate to compositions comprising a combination of at least one compound of formula (I) and at least one pesticide and / or at least one enzyme inhibitor. In some embodiments, the compound of formula (I) is represented by the following formula: [ka]

[0005] In some embodiments, V is a substituted or unsubstituted straight or branched chain C-C 12 Alkyl, substituted or unsubstituted, straight or branched chain, C2-C 12 Alkenyl, substituted or unsubstituted, straight or branched chain, C3-C 12 Alkynyl, substituted or unsubstituted, straight or branched chain, C3-C 12 Cycloalkyl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted straight or branched C-C 12 In some embodiments, W is a cycloalkenyl. In some embodiments, W is hydrogen or a substituted or unsubstituted, saturated or unsaturated C3-C6 alkane or alkene. In some embodiments, X is an oxygen or sulfur atom. In some embodiments, Y is hydroxyl, sulfhydryl, amino, halogen, or an ether with alkyl (C1-C7) of various lengths. In some embodiments, Z is a substituted or unsubstituted, straight or branched C1-C 12 Alkyl, substituted or unsubstituted, straight or branched chain, C3-C 12 Cycloalkyl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted straight or branched C-C 12 In some embodiments, W may be attached to Z via a substituted or unsubstituted, saturated or unsaturated C3-C6 alkane or alkene.

[0006] In some embodiments, the at least one insecticide is a pyrethroid, a neonicotinoid, or an organophosphate. In some embodiments, the pyrethroid comprises allethrin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, d-fenothrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, permethrin, fenothrin, resmethrin, sumithrin, taufluvalinate, tefluthrin, tetramethrin, or tralomethrin. In some embodiments, the neonicotinoid comprises acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, or thiamethoxam. In some embodiments, the organophosphate is selected from the group consisting of acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famflur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyaphos, isofenphos, O-(methoxyaminothiazolinone), methylisothiazolinone, ... (ophosphoryl) isopropyl salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton methyl, parathion, parathion methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon or vamidothion.

[0007] In some embodiments, the at least one enzyme inhibitor is a glutathione-S-transferase inhibitor, a mixed function oxidase inhibitor, or an esterase inhibitor. In some embodiments, the glutathione-S-transferase inhibitor comprises diethyl maleate, quercetin, or tannic acid. In some embodiments, the mixed function oxidase inhibitor comprises piperonyl butoxide, isoniazid, SKF 525A, or MGK 264. In some embodiments, the esterase inhibitor comprises S,S,S-tributyl phosphorotrithioate, iprobenfos, or triphenyl phosphate.

[0008] In some embodiments, the compositions of the present disclosure exhibit insecticidal, paralyzing, repellent, or disruptive effects on invertebrate feeding and growth and / or the activity of their larvae without affecting mammals, fish, or poultry. In some embodiments, the compositions of the present disclosure are formulated as pesticide formulations. In some embodiments, the pesticide formulations are wettable powders, granules, emulsifiable concentrates, sprays, atomized concentrates, liquids, or ultra-low volume formulations that can form emulsions or suspensions by adding water. In some embodiments, the at least one compound of Formula (I) acts as a synergist by significantly enhancing the toxicity of the pesticide. In some embodiments, the at least one compound of Formula (I) may be administered in a sublethal dose. In some embodiments, the at least one compound of Formula (I) comprises pogostone.

[0009] Some embodiments provided herein relate to a method for killing, controlling, paralyzing, repelling, knocking down, or hindering pests. In some embodiments, the method comprises applying any of the compositions provided herein to an environment or pest in need of pest control. In some embodiments, the pest is an insect, arachnid, or their larvae. [Brief explanation of the drawings]

[0010] [Figure 1]1 shows the evaluation of topically applied pogostone on female Aedes aegypti mosquitoes to determine sublethal doses for synergist experiments.

[0011] [Figure 2] Figure 1 shows an evaluation of the spatial repellency of pogostone against pyrethroid-susceptible (Orlando) and pyrethroid-resistant (Puerto Rico) strains of adult female Aedes aegypti mosquitoes. DETAILED DESCRIPTION OF THE INVENTION

[0012] In the following detailed description, the present invention will be described with reference to the accompanying drawings, which form a part hereof. Unless otherwise specified, like symbols in the drawings generally refer to like elements. The embodiments set forth in the detailed description, drawings, and claims are for illustrative purposes only and are not intended to limit the present invention in any way. Other embodiments may be employed, and other changes may be made, without departing from the spirit or scope of the subject matter described herein. It will be readily understood that the aspects of the present disclosure as outlined herein and illustrated in the drawings can be arranged, substituted, combined, separated, and designed in various configurations, and all such aspects are expressly encompassed herein.

[0013] Embodiments of the present disclosure relate to compositions used to control, kill, suppress, repel, or mitigate pests. Specifically, the present disclosure relates to compositions comprising a pyrone compound, a pyrethroid compound, a neonicotinoid compound, an organophosphate compound, an enzyme inhibitor, or a combination thereof. Some embodiments relate to methods of making the compositions of the present disclosure. Some embodiments relate to methods of controlling, killing, suppressing, repelling, or mitigate pests by applying a composition described herein to an environment or area in need of pest control.

[0014] Pyrethroid insecticides promote the continuous influx of sodium ions through the cell membranes of insect nerve cells, causing hyperexcitability in the insect nervous system, inducing spastic paralysis and leading to death. Pyrethroid insecticides easily penetrate insect cuticles and distribute uniformly throughout the insect's body, exerting toxicity within minutes of contact with the target insect. One of the key symptoms of pyrethroid poisoning is rapid lethal knockdown. Unlike slow-acting insecticides, pyrethroids' knockdown effect prevents mosquitoes from feeding on the host, making them ideal for public health vector control. Furthermore, this knockdown effect is important for agricultural pest control, preventing insects from devouring various plant parts. Furthermore, this knockdown effect contributes to insect mortality through multiple mechanisms, such as inhibiting grooming (which reduces fungal spore accumulation on insects), increasing susceptibility to predation, and dehydration. This knockdown effect is a crucial consideration for the future development of insecticide formulations containing natural products with novel modes of action.

[0015] One of the barriers to identifying new insecticide formulations is ensuring that they are fast-acting, highly lethal, and safe for application in residential areas, for example. While many synthetic insecticides have toxicity that causes rapid neurotoxicity, they are highly toxic to humans and other vertebrates and have relatively long environmental half-lives, making them ineffective tools for the search for new insecticide formulations. Identifying insecticide candidates that have low mammalian toxicity, are rapidly degraded, and can rapidly induce and kill insects by displacing them is of paramount importance. Several compounds found in plant essential oils possess these crucial properties (Isman 2011). The mechanisms of action of plant essential oils identified to date are diverse and complex, suggesting the involvement of several molecular targets. For example, patchouli oil has been shown to be effective against a variety of insects, and its active ingredient is believed to be a pyrone molecule, distinct from the terpenoids found in plant essential oils (Chen 2017). In Drosophila melanogaster, the binding affinity of selected terpenoids to heterologously expressed tyramine receptors has been reported to directly correlate with the toxicity of these terpenoids in wild-type Drosophila melanogaster (Enan 2005). Furthermore, significant specific binding of various terpenoids to the octopamine receptor in the American cockroach has been reported (Enan 2001). Plant essential oil components exert their effects through other mechanisms, such as binding to the GABAA receptor ion channel as antagonists, acetylcholinesterase inhibitors, or nicotinic acetylcholine receptor blockers (Tong and Coats 2010; Anderson and Coats 2012; Tong et al. 2012). Plant essential oils and their components, with their low potential for cross-resistance with currently available insecticides and versatile mechanisms of action, are proving to be valuable tools in pest management strategies. With resistance rapidly emerging to most currently available insecticides on the market, these plant essential oil components may be effective alternatives to future insecticide formulations.

[0016] There are three main mechanisms by which resistance develops: reduced transport of the pesticide into the pest; insecticide metabolism (thus detoxifying it); and target site insensitivity. These resistance mechanisms can occur individually in different insects, but often in combination, resulting in significantly higher overall resistance. This condition is called "multifactorial resistance."

[0017] Many insects possess detoxification systems that originally evolved to protect them from naturally occurring toxins in the environment. Metabolism of insecticides can occur before they reach the target site, and when they come into contact with detoxifying enzymes, they are converted into less toxic substances, easier to excrete, or both. The most important enzyme systems involved in insecticide resistance include a) mixed-function oxidases, b) glutathione-S-transferases, and c) esterases. Enhanced activity of one or more of these enzymes has been found to confer resistance in several insect species.

[0018] Insect detoxification enzyme systems have been investigated in vivo using conventional bioassays and in vitro using biochemical analyses. Synergists, such as DEF (S,S,S-tributyl phosphorothioate) and TPP (O,O,O-triphenyl phosphate), are widely used in conventional bioassays. These compounds significantly enhance the toxicity of insecticides, but may be virtually nontoxic when used alone. Synergists for insecticides act by inhibiting metabolic enzymes. Differences in lethality in bioassays using pesticides in the presence or absence of synergists can be used to determine whether putative metabolic enzymes are involved in resistance.

[0019] Some embodiments provided herein relate to formulations comprising a 2-pyrone-based molecule, the 2-pyrone-based molecule having the general formula (I): [ka] wherein V is a substituted or unsubstituted straight or branched chain C1-C 12 Alkyl, substituted or unsubstituted, straight or branched chain, C2-C 12 Alkenyl, substituted or unsubstituted, straight or branched chain, C3-C 12 Alkynyl, substituted or unsubstituted, straight or branched chain, C3-C 12 Cycloalkyl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted straight or branched C-C 12 is cycloalkenyl; W is hydrogen or a substituted or unsubstituted, saturated or unsaturated C3-C6 alkane or alkene; X is an oxygen or sulfur atom; Y is hydroxyl, sulfhydryl, amino, halogen, or ether with alkyl (C1-C7) of various lengths; Z is a substituted or unsubstituted straight or branched chain C1-C 12 Alkyl, substituted or unsubstituted, straight or branched chain, C3-C 12 Cycloalkyl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted straight or branched C-C 12 is cycloalkenyl; W may be attached to Z via a substituted or unsubstituted, saturated or unsaturated C3-C6 alkane or alkene. Examples of compounds include those represented by the following formula:

[0020] In some embodiments, the compositions of the present disclosure further comprise at least one insecticide and / or at least one enzyme inhibitor, which may be referred to as synergists. Some embodiments provided herein relate to methods for producing the compositions of the present disclosure. Some embodiments provided herein relate to methods for applying the compositions of the present disclosure, wherein the compositions kill invertebrates, such as insects, arachnids, and / or their larvae, while minimizing the effect on other species, such as mammals, fish, and poultry. In some embodiments, the compositions of the present disclosure are applied at relatively low concentrations and are effective for a relatively long period of time, such as at least 24 hours.

[0021] Unless otherwise defined, all technical and scientific terms used herein have the meaning commonly understood by one of ordinary skill in the art. The use of the term "including" and other forms such as "include," "includes," and "included" is not limiting. The use of the term "having" and other forms such as "have," "has," and "had" is also not limiting. As used herein, whether in transitional clauses or in the body of a claim, the terms "comprise(s)" and "comprising" are to be interpreted as having an open-ended meaning. That is, these terms are to be interpreted as synonymous with the expressions "having at least" or "including at least." For example, when the term "comprise" is used in the context of a method, it means that the method includes at least the specified steps and may include additional steps. Also, when the term "comprise" is used in the context of a compound, composition, or device, it means that the compound, composition, or device includes at least the specified features or components and may include additional features or components.

[0022] As used herein, an "R" group represents a substituent that may be bonded to the designated atom. The R groups described herein with respect to pyrone-based compounds (including compounds of Formula (I)) are defined by the symbols "V," "W," "X," "Y," and "Z." The descriptions of R groups also apply to these groups as defined in the compounds described herein. R groups may be substituted or unsubstituted. When two "R" groups are described as "together with the atoms to which they are attached" forming a ring or ring system, it is meant that the atoms, intervening bonds, and the collective unit of the two R groups form the ring.

[0023] The naming convention for a particular radical is interpreted as including a monoradical or a diradical, depending on the context. For example, if a substituent requires two bonding sites to attach to another molecule, the substituent is interpreted as a diradical. For example, substituents specified as alkyl, which require two bonding sites, include diradicals such as -CH2-, -CH2CH2-, and -CH2CH(CH3)CH2-. Other radical naming conventions clearly indicate that the radical is a diradical, such as "alkylene" or "alkenylene."

[0024] As used herein, the term "halogen" or "halo" refers to any one of the radioactive stable atoms in column 7 of the periodic table of the elements, such as fluorine, chlorine, bromine, or iodine.

[0025] In this specification, "C" is a formula in which "a" and "b" are integers. a -C b" refers to the number of carbon atoms in an alkyl, alkenyl, or alkynyl group, or the number of ring atoms in a cycloalkyl or aryl group. That is, the alkyl, alkenyl, alkynyl, cycloalkyl ring, and aryl ring as a whole may contain from "a" to "b" carbon atoms. For example, a "C1-C4 alkyl" group refers to any alkyl group having 1 to 4 carbon atoms, i.e., CH3-, CH3CH2-, CH3CH2CH2-, (CH3)2CH-, CH3CH2CH2CH2-, CH3CH2CH(CH3)-, and (CH3)3C-; a ​​C3-C4 cycloalkyl group refers to any cycloalkyl group having 3 to 4 carbon atoms, i.e., cyclopropyl and cyclobutyl. Similarly, a "4- to 6-membered heterocyclyl" group refers to any heterocyclyl group having a total of 4 to 6 ring atoms, such as azetidine, oxetane, oxazoline, pyrrolidine, piperidine, piperazine, morpholine, and the like. When "a" or "b" is not specified for an alkyl group, alkenyl group, alkynyl group, cycloalkyl group, or aryl group, the broadest range described by those definitions is assumed. Also, as used herein, the term "C1-C6" includes C1, C2, C3, C4, C5, and C6, as well as ranges bounded by any two of these numbers. For example, C1-C6 alkyl includes C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C2-C6 alkyl, C1-C3 alkyl, etc. Similarly, C2-C6 alkenyl includes C2 alkenyl, C3 alkenyl, C4 alkenyl, C5 alkenyl, C6 alkenyl, C2-C5 alkenyl, C3-C4 alkenyl, etc. C2-C6 alkynyl includes C2 alkynyl, C3 alkynyl, C4 alkynyl, C5 alkynyl, C6 alkynyl, C2-C5 alkynyl, C3-C4 alkynyl, etc. C3-C8 cycloalkyl includes hydrocarbon rings containing 3, 4, 5, 6, 7, or 8 carbon atoms, or any two of these numbers within the upper and lower limits, and examples thereof include C3-C7 cycloalkyl and C5-C6 cycloalkyl.

[0026] As used herein, "alkyl" refers to a straight or branched hydrocarbon chain that is fully saturated (i.e., contains no double or triple bonds). An alkyl group may have 1 to 20 carbon atoms. (When a numerical range such as "1 to 20" is recited herein, such a numerical range always refers to each integer within the range. For example, "1 to 20 carbon atoms" means that the alkyl group may be composed of up to 20 carbon atoms, such as 1 carbon atom, 2 carbon atoms, 3 carbon atoms, etc.; however, the definition of this disclosure also encompasses the term "alkyl" without a specified numerical range of carbon atoms.) An alkyl group may be a medium-sized alkyl having 1 to 9 carbon atoms. Alternatively, an alkyl group may be a lower alkyl having 1 to 6 carbon atoms. An alkyl group may be designated as "C1-C4 alkyl" or similar designations. As an example, "C1-C6 alkyl" indicates that there are 1 to 6 carbon atoms in the alkyl chain, i.e., the alkyl chain is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and t-butyl. Typical alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, and the like.

[0027] As used herein, "alkoxy" refers to the formula -OR, where R is alkyl as defined above, such as "C1-C9 alkoxy", including, but not limited to, methoxy, ethoxy, n-propoxy, 1-methylethoxy (isopropoxy), n-butoxy, iso-butoxy, sec-butoxy, and tert-butoxy.

[0028] As used herein, "alkenyl" refers to a straight or branched hydrocarbon chain containing one or more double bonds. An alkenyl group can have 2 to 20 carbon atoms, although the definition in this disclosure also encompasses the term "alkenyl" without a specified numerical range. An alkenyl group can also be a medium-sized alkenyl having 2 to 9 carbon atoms. Alternatively, an alkenyl group can be a lower alkenyl having 2 to 6 carbon atoms. An alkenyl group may be designated as "C2-C6 alkenyl" or similar designations. For example, "C2-C6 alkenyl" indicates that there are 2 to 6 carbon atoms in the alkenyl chain, i.e., the alkenyl chain is selected from the group consisting of ethenyl, propen-1-yl, propen-2-yl, propen-3-yl, buten-1-yl, buten-2-yl, buten-3-yl, buten-4-yl, 1-methylpropen-1-yl, 2-methylpropen-1-yl, 1-ethylethen-1-yl, 2-methylpropen-3-yl, buta-1,3-dienyl, buta-1,2-dienyl, and buta-1,2-dien-4-yl. Exemplary alkenyl groups include, but are not limited to, ethenyl, propenyl, butenyl, pentenyl, and hexenyl.

[0029] As used herein, "alkynyl" refers to a straight or branched hydrocarbon chain containing one or more triple bonds. An alkynyl group can have 2 to 20 carbon atoms, although the definition herein also encompasses the term "alkynyl" without a specified numerical range. An alkynyl group can also be a medium-sized alkynyl group having 2 to 9 carbon atoms. Alternatively, an alkynyl group can be a lower alkynyl group having 2 to 6 carbon atoms. An alkynyl group may be designated as "C2-C6 alkynyl" or similar designations. By way of example, "C2-C6 alkynyl" indicates that there are 2 to 6 carbon atoms in the alkynyl chain, i.e., the alkynyl chain is selected from the group consisting of ethynyl, propyn-1-yl, propyn-2-yl, butyn-1-yl, butyn-3-yl, butyn-4-yl, and 2-butynyl. Typical alkynyl groups include, but are not limited to, ethynyl, propynyl, butynyl, pentynyl, hexynyl, and the like.

[0030] As used herein, "heteroalkyl" refers to a linear or branched hydrocarbon chain containing one or more heteroatoms, i.e., a linear or branched hydrocarbon chain containing an element other than carbon in its backbone, such as, but not limited to, nitrogen, oxygen, or sulfur. Heteroalkyl groups can have 1 to 20 carbon atoms, although the definition herein also encompasses the term "heteroalkyl" without a specified numerical range. Heteroalkyl groups can also be medium-sized heteroalkyls containing 1 to 9 carbon atoms. Heteroalkyl groups can also be lower heteroalkyls containing 1 to 6 carbon atoms. Heteroalkyl groups can be designated "C1-C6 heteroalkyl" or similar names. Heteroalkyl groups can contain one or more heteroatoms. By way of example, "C4-C6 heteroalkyl" indicates that the heteroalkyl chain has 4 to 6 carbon atoms and one or more additional heteroatoms in the backbone.

[0031] The term "aromatic" means a ring or ring system having a conjugated π-electron system, and includes both carbocyclic aromatic groups (e.g., phenyl) and heterocyclic aromatic groups (e.g., pyridine). The term includes monocyclic or polycyclic fused ring groups (i.e., rings that share adjacent pairs of atoms), so long as the entire ring system is aromatic.

[0032] As used herein, "aryl" refers to an aromatic ring or ring system (i.e., two or more fused rings that share two adjacent carbon atoms) that contains only carbon in its ring backbone. When aryl is a ring system, all rings within the ring system are aromatic. An aryl group can have 6 to 18 carbon atoms, although the definition of this disclosure also encompasses the term "aryl" where no numerical range is specified. In some embodiments, an aryl group has 6 to 10 carbon atoms. An aryl group is defined as "C6-C 10 aryl," "C6 aryl or C 10 The aryl group may be designated "aryl" or similar names. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, azulenyl, and anthracenyl.

[0033] "Aralkyl" or "arylalkyl" refers to, for example, "C 7-14 An aryl group linked as a substituent via an alkylene group, such as "aralkyl," includes, but is not limited to, benzyl, 2-phenylethyl, 3-phenylpropyl, and naphthylalkyl. In some cases, the alkylene group is a lower alkylene group (e.g., C1-C6 alkylene groups, etc.).

[0034] As used herein, "heteroaryl" refers to an aromatic ring or ring system (i.e., two or more fused rings sharing two adjacent atoms) that contains one or more heteroatoms in its ring backbone, i.e., elements other than carbon, such as, but not limited to, nitrogen, oxygen, or sulfur. When heteroaryl is a ring system, all rings within the ring system are aromatic. Heteroaryl groups can have 5 to 18 ring members (e.g., the number of atoms, such as carbon atoms and heteroatoms, that make up the ring backbone), although the definition herein encompasses the term "heteroaryl" without a specified numerical range. In some embodiments, heteroaryl groups have 5 to 10 ring members or 5 to 7 ring members. Heteroaryl groups may also be designated as "5-7-membered heteroaryl," "5-10-membered heteroaryl," or similar names. Examples of heteroaryl rings include, but are not limited to, furyl, thienyl, phthalazinyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, triazolyl, thiadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, indolyl, isoindolyl, and benzothienyl.

[0035] "Heteroaralkyl" or "heteroarylalkyl" is a heteroaryl group linked as a substituent via an alkylene group. Examples include, but are not limited to, 2-thienylmethyl, 3-thienylmethyl, furanylmethyl, thienylethyl, pyrrolylalkyl, pyridylalkyl, isoxazolylalkyl, and imidazolylalkyl. In some cases, the alkylene group is a lower alkylene group (e.g., C1-C6 alkylene group).

[0036] As used herein, "carbocyclyl" refers to a non-aromatic ring or ring system containing only carbon atoms in its ring system backbone. When a carbocyclyl is a ring system, two or more rings may be connected by fused, bridged, or spiro bonds. The degree of saturation of a carbocyclyl is not particularly limited, as long as at least one ring in the ring system is aromatic. Thus, carbocyclyl includes cycloalkyl, cycloalkenyl, and cycloalkynyl. A carbocyclyl group may have 3 to 20 carbon atoms, although the definition in this disclosure also encompasses the term "carbocyclyl" without a specified numerical range. A carbocyclyl group may be a medium-sized carbocyclyl having 3 to 10 carbon atoms. A carbocyclyl group may also be a carbocyclyl having 3 to 6 carbon atoms. A carbocyclyl group may be designated as "C3-C6 carbocyclyl" or similar names. Examples of carbocyclyl rings include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl, 2,3-dihydroindene, bicyclo[2.2.2]octanyl, adamantyl, and spiro[4.4]nonanyl.

[0037] As used herein, "cycloalkyl" means a fully saturated carbocyclyl ring or ring system, examples of which include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0038] As used herein, "heterocyclyl" refers to a non-aromatic ring or ring system containing at least one heteroatom in its ring system backbone. Heterocyclyls may be fused, bridged, or spiro-linked. The degree of saturation of a heterocyclyl is not particularly limited, so long as at least one ring in the ring system is aromatic. The heteroatom may be present in either a non-aromatic or aromatic ring in the ring system. Heterocyclyl groups may have 3 to 20 ring members (i.e., the number of atoms constituting the ring backbone, such as carbon atoms and heteroatoms), although the definition in this disclosure also encompasses the term "heterocyclyl" without a specified numerical range. Heterocyclyl groups may be medium-sized heterocyclyls having 3 to 10 ring members. Heterocyclyl groups may also be heterocyclyls having 3 to 6 ring members. Heterocyclyl groups may also be designated as "3- to 6-membered heterocyclyls" or similar names. In preferred 6-membered monocyclic heterocyclyls, the heteroatoms are selected from 1 to 3 selected from O, N and S, and in preferred 5-membered monocyclic heterocyclyls, the heteroatoms are selected from 1 or 2 heteroatoms selected from O, N and S.Examples of heterocyclyl rings include azepinyl, acridinyl, carbazolyl, cinnolinyl, dioxolanyl, imidazolinyl, imidazolidinyl, morpholinyl, oxiranyl, oxepanyl, thiepanyl, piperidinyl, piperazinyl, dioxopiperazinyl, pyrrolidinyl, pyrrolidonyl, pyrrolidionyl, 4-piperidonyl, pyrazolinyl, pyrazolidinyl, 1,3-dioxinyl, 1,3-dioxanyl, 1,4-dioxinyl, 1,4-dioxanyl, 1,3-oxathianyl, 1,4-oxathiinyl, 1,4-oxathianyl, 2H-1,2-oxazinyl, trioxanyl, hexahydro-1,3 ,5-triazinyl, 1,3-dioxolyl, 1,3-dioxolanyl, 1,3-dithiolyl, 1,3-dithiolanyl, isoxazolinyl, isoxazolidinyl, oxazolinyl, oxazolidinyl, oxazolidinonyl, thiazolinyl, thiazolidinyl, 1,3-oxathiolanyl, indolinyl, isoindolinyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, tetrahydrothiopyranyl, tetrahydro-1,4-thiazinyl, thiamorpholinyl, dihydrobenzofuranyl, benzimidazolidinyl, and tetrahydroquinoline.

[0039] An "O-carboxy" group refers to an "-OC(=O)R" group, where R is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 carbocyclyl, C6-C 10 It is selected from aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclyl, as these groups are defined herein.

[0040] A "C-carboxy" group refers to a "-C(=O)OR" group, where R is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 carbocyclyl, C6-C 10and is selected from the group consisting of aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclyl, as defined herein. Examples of C-carboxy groups include, but are not limited to, carboxyl (i.e., —C(═O)OH).

[0041] An "alkyl C-carboxy" group is defined as "-(CH) n "C(=O)OR" group, where n is 1 to 6, and the C(=O)OR group is the same as defined for the "C-carboxy" group.

[0042] A "thioalkyl" group refers to an "-SR" group, where R is C-C alkyl, C-C alkenyl, C-C alkynyl, C-C carbocyclyl, C-C 10 It is selected from aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclyl, as these groups are defined herein.

[0043] A "sulfonyl" group refers to a "-SO2R" group, where R is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 carbocyclyl, C6-C7 10 It is selected from aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclyl, as these groups are defined herein.

[0044] A "sulfino" group refers to a "-S(=O)OH" group.

[0045] The "S-sulfonamide" group is "-SO2NR A R B " group, wherein R A and R B are each independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 carbocyclyl, C6-C 10 It is selected from aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclyl, as these groups are defined herein.

[0046] The "N-sulfonamide" group is "-N(R A )SO2R B " group, wherein R A and R b are each independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 carbocyclyl, C6-C 10 It is selected from aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclyl, as these groups are defined herein.

[0047] The "C-amide" group is "-C(=O)NR A R B " group, wherein R A and R B are each independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 carbocyclyl, C6-C 10 It is selected from aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclyl, as these groups are defined herein.

[0048] The "N-amide" group is "-N(R A )C(=O)R B " group, wherein R A and R B are each independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 carbocyclyl, C6-C 10 It is selected from aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclyl, as these groups are defined herein.

[0049] The "amino" group is "-NR A R B " group, wherein R A and R B are each independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 carbocyclyl, C6-C 10and selected from aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclyl, as defined herein. Examples of amino groups include, but are not limited to, free amino (i.e., -NH).

[0050] An "aminoalkyl" group refers to an amino group linked via an alkylene group.

[0051] An "alkoxyalkyl" group refers to an alkoxy group linked via an alkylene group, such as "C2-C8 alkoxyalkyl".

[0052] "Aralkoxy" or "arylalkoxy" refers to, for example, "C 7-14 An aryl group linked as a substituent via an alkoxy group, such as "arylalkoxy," includes, but is not limited to, benzyl, 2-phenylethyl, 3-phenylpropyl, and naphthylalkyl. In some cases, the alkoxy group is a lower alkoxy group (i.e., a C1-C3 alkoxy group).

[0053] As used herein, a substituted group is a group derived from an unsubstituted parent group by replacing one or more hydrogen atoms with another atom or group. Unless otherwise specified, when a group is described as "substituted," this means that the group is substituted with one or more substituents, and the one or more substituents are selected from the group consisting of C1-C6 alkyl, C1-C6 alkenyl, C1-C6 alkynyl, C1-C6 heteroalkyl, C3-C7 carbocyclyl (optionally substituted with halo, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, or C1-C6 haloalkoxy), C3-C7 carbocyclylC1-C6 alkyl (halo, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, or C1-C6 haloalkoxy), 3-10 membered heterocyclyl (optionally substituted with halo, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, or C1-C6 haloalkoxy), 3-10 membered heterocyclylC1-C6 alkyl (optionally substituted with halo, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, or C1-C6 haloalkoxy), aryl (halo, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, or C1-C6 haloalkoxy), aryl(C1-C6)alkyl (optionally substituted with halo, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, or C1-C6 haloalkoxy), 5-10 membered heteroaryl (optionally substituted with halo, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, or C1-C6 haloalkoxy), 5-10 membered heteroaryl aryl(C1-C6)alkyl (optionally substituted with halo, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, or C1-C6 haloalkoxy), halo, -CN, hydroxy, C1-C6 alkoxy, C1-C6 alkoxy(C1-C6)alkyl (i.e., ether), aryloxy, sulfhydryl (mercapto), halo(C1-C6)alkyl (e.g., -CF3), halo(C1-C6)alkoxy (e.g., -OCF3), C1-C6 alkylthio, arylthio, amino,Amino (C1-C6) alkyl, nitro, O-carbamyl, N-carbamyl, O-thiocarbamyl, N-thiocarbamyl, C-amido, N-amido, S-sulfonamido, N-sulfonamido, C-carboxy, O-carboxy, acyl, cyanato, isocyanato, thiocyanato, isothiocyanato, sulfinyl, sulfonyl, -SO3H, sulfino, -OSO2C, 1-4 alkyl, and oxo (=O). Additionally, when a group is described as being "optionally substituted," that group can be substituted with those substituents.

[0054] As used herein, the term "hydroxy" refers to an --OH group.

[0055] As used herein, the term "cyano" group refers to a "-CN" group.

[0056] As used herein, the term "diazo" refers to the group -N2.

[0057] composition Some embodiments provided herein relate to compositions used for pest control. In some embodiments, the compositions of the present disclosure comprise a combination of a compound of formula (I) and at least one pesticide and / or at least one enzyme inhibitor. In some embodiments, the compound of formula (I) is represented by the following formula: [ka]

[0058] In some embodiments, V is a substituted or unsubstituted straight or branched chain C-C 12 Alkyl, substituted or unsubstituted, straight or branched chain, C2-C 12 Alkenyl, substituted or unsubstituted, straight or branched chain, C3-C 12 Alkynyl, substituted or unsubstituted, straight or branched chain, C3-C 12Cycloalkyl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted straight or branched C-C 12 In some embodiments, W is a cycloalkenyl. In some embodiments, W is hydrogen or a substituted or unsubstituted, saturated or unsaturated C3-C6 alkane or alkene. In some embodiments, X is an oxygen or sulfur atom. In some embodiments, Y is hydroxyl, sulfhydryl, amino, halogen, or an ether with alkyl (C1-C7) of various lengths. In some embodiments, Z is a substituted or unsubstituted, straight or branched C1-C 12 Alkyl, substituted or unsubstituted, straight or branched chain, C3-C 12 Cycloalkyl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted straight or branched C-C 12 In some embodiments, W may be attached to Z via a substituted or unsubstituted, saturated or unsaturated C3-C6 alkane or alkene.

[0059] In some embodiments, the at least one insecticide is a pyrethroid, a neonicotinoid, or an organophosphate. In some embodiments, the pyrethroid comprises allethrin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, d-fenothrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, permethrin, fenothrin, resmethrin, sumithrin, taufluvalinate, tefluthrin, tetramethrin, or tralomethrin. In some embodiments, the neonicotinoid comprises acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, or thiamethoxam. In some embodiments, the organophosphate is selected from the group consisting of acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famflur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyaphos, isofenphos, O-(methoxyaminothiazolinone), methylisothiazolinone, ... (ophosphoryl) isopropyl salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton methyl, parathion, parathion methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon or vamidothion.

[0060] In some embodiments, the content of the compound of formula (I) in the composition of the present disclosure is in the range of about 0.01 ng to about 1 mg per unit volume, e.g., 0.01 ng, 0.1 ng, 1 ng, or 10 ng, 0.1 μg, 1 μg, or 10 μg, or 0.1 mg or 1 mg per unit volume, or an amount within a range defined by any two of these numerical values, and the unit volume is in the range of 0.1 mL to 1 L, e.g., 0.1 mL, 1 mL, 10 mL, 100 mL, or 1000 mL, or a volume within a range defined by any two of these numerical values. In some embodiments, the content of the insecticide in the composition of the present disclosure is in the range of about 0.01 ng to about 1 mg per unit volume, e.g., 0.01 ng, 0.1 ng, 1 ng, or 10 ng, 0.1 μg, 1 μg, or 10 μg, or 0.1 mg or 1 mg per unit volume, or an amount within a range defined by any two of these values, and the unit volume is in the range of 0.1 mL to 1 L, e.g., 0.1 mL, 1 mL, 10 mL, 100 mL, or 1000 mL, or an amount within a range defined by any two of these values. In some embodiments, the content of the enzyme inhibitor in the composition of the present disclosure is in the range of about 0.01 ng to about 1 mg per unit volume, e.g., 0.01 ng, 0.1 ng, 1 ng, or 10 ng, 0.1 μg, 1 μg, or 10 μg, or 0.1 mg or 1 mg per unit volume, or an amount within a range of any two of these values, and the unit volume is in the range of 0.1 mL to 1 L, e.g., 0.1 mL, 1 mL, 10 mL, 100 mL, or 1000 mL, or a volume within a range of any two of these values. In some embodiments, each component of the compound of Formula (I), insecticide, or enzyme inhibitor is contained in a solid formulation, and the amount of each component is expressed as mass relative to the total mass (mass / mass) rather than mass / volume.

[0061] In some embodiments, the compositions of the present disclosure are formulated as pesticide formulations, which in some embodiments are granules, dusts, concentrates, ready-to-use formulations, sprays, liquids, or aerosols.

[0062] In some embodiments, a pest control composition comprising pogostone and an insecticide is provided. In some embodiments, a composition comprising pogostone and a pyrethroid insecticide is provided. In some embodiments, the pyrethroid insecticide can be permethrin. In some embodiments, a composition comprising pogostone and a neonicotinoid insecticide is provided. In some embodiments, the neonicotinoid insecticide can be dinotefuran. In some embodiments, pogostone can act as a synergist by significantly enhancing the toxicity of the insecticide. In some embodiments, enhanced toxicity can be measured by increased knockdown and / or increased mortality. In some embodiments, pogostone can be included in a sublethal dose. In some embodiments, compositions of the present disclosure comprising pogostone are equally effective in controlling pests susceptible to pyrethroid insecticides and pests resistant to pyrethroid insecticides.

[0063] In some embodiments, a method for controlling pests is provided, comprising applying a composition comprising pogostone and an insecticide. In some embodiments, a composition comprising pogostone and a pyrethroid insecticide is provided. In some embodiments, the pyrethroid insecticide can be permethrin. In some embodiments, a composition comprising pogostone and a neonicotinoid insecticide is provided. In some embodiments, the neonicotinoid insecticide can be dinotefuran. In some embodiments, pogostone can act as a synergist by significantly enhancing the toxicity of the insecticide. In some embodiments, enhanced toxicity can be measured by increased knockdown and / or increased mortality. In some embodiments, pogostone can be included in a sublethal dose. In some embodiments, the compositions of the present disclosure comprising pogostone are equally effective in controlling pests susceptible to pyrethroid insecticides and pests resistant to pyrethroid insecticides.

[0064] Manufacturing method Some embodiments provided herein relate to methods for producing the compositions of the present disclosure. In some embodiments, the methods of the present disclosure include synthesizing a compound of Formula (I) and adding the compound of Formula (I) to one or more insecticides and / or one or more enzyme inhibitors. In some embodiments, the compositions of the present disclosure are formulated so that the composition of the compound of Formula (I), the composition of the insecticide, and / or the composition of the enzyme inhibitor are stored separately and mixed immediately before application to an environment or pest in need of pest control. In some embodiments, the separately stored compositions are automatically mixed during or immediately before application. In some embodiments, the formulation is prepared by mixing the separately stored compositions.

[0065] Pest control methods Some embodiments provided herein relate to methods for pest control. As used herein, the term "control" has its ordinary meaning as understood herein, meaning to prevent, reduce, or eliminate the presence of pests in an environment where pest control is desired. In some embodiments, controlling pests includes killing, suppressing, repelling, deterring, reducing, or eliminating the presence of pests. In some embodiments, controlling pests includes disrupting pest activity (e.g., feeding, mating, etc.), paralyzing pests, or otherwise preventing the growth, spread, survival, or reproduction of pests in an environment where pest control is desired. In some embodiments, the methods of the present disclosure comprise applying a composition described herein to pests, pest colonies, or an environment where pest control is desired. Application can be by spraying, atomizing, dusting, dipping, dripping, dropping, covering, sowing, or directly placing or otherwise applying a composition of the present disclosure to the pest, pest colony, or target environment, hi some embodiments, the pest is an insect, arachnid, or their larvae.

[0066] Some embodiments provided herein are illustrated by the following listed embodiments.

[0067] 1. A composition comprising: at least one compound of formula (I): at least one insecticide and / or at least one enzyme inhibitor; Including, [ka] During the ceremony, V is a substituted or unsubstituted straight or branched chain C1-C 12 Alkyl, substituted or unsubstituted, straight or branched chain, C2-C 12 Alkenyl, substituted or unsubstituted, straight or branched chain, C3-C 12 Alkynyl, substituted or unsubstituted, straight or branched chain, C3-C 12 Cycloalkyl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted straight or branched C-C 12 is cycloalkenyl; W is hydrogen or a substituted or unsubstituted, saturated or unsaturated C3-C6 alkane or alkene; X is an oxygen or sulfur atom; Y is hydroxyl, sulfhydryl, amino, halogen, or ether with alkyl (C1-C7) of various lengths; Z is a substituted or unsubstituted straight or branched chain C1-C 12 Alkyl, substituted or unsubstituted, straight or branched chain, C3-C 12 Cycloalkyl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted straight or branched C-C 12 is cycloalkenyl; W may be attached to Z via a substituted or unsubstituted saturated or unsaturated C3-C6 alkane or alkene; composition.

[0068] 2. The composition of embodiment 1, wherein the at least one insecticide is a pyrethroid, a neonicotinoid, or an organophosphate.

[0069] 3. The composition of embodiment 2, wherein the pyrethroid comprises allethrin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, d-phenothrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, permethrin, fenothrin, resmethrin, sumithrin, taufluvalinate, tefluthrin, tetramethrin, or tralomethrin.

[0070] 4. The composition of embodiment 2, wherein the neonicotinoid comprises acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, or thiamethoxam.

[0071] 5. The organophosphates are acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famfur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyaphos, isofenphos, O-(methoxyaminothiophosphoryl)salicylate isoform The composition of embodiment 2, comprising isopropyl, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton methyl, parathion, parathion methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimphos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, or vamidothion.

[0072] 6. The composition of any one of embodiments 1 to 5, wherein the at least one enzyme inhibitor is a glutathione-S-transferase inhibitor, a mixed function oxidase inhibitor, or an esterase inhibitor.

[0073] 7. The composition of embodiment 6, wherein the glutathione-S-transferase inhibitor comprises diethyl maleate, quercetin, or tannic acid.

[0074] 8. The composition of embodiment 6, wherein the mixed function oxidase inhibitor comprises piperonyl butoxide, isoniazid, SKF 525A, or MGK 264.

[0075] 9. The composition of embodiment 6, wherein the esterase inhibitor comprises S,S,S-tributyl phosphorotrithioate, iprobenfos, or triphenyl phosphate.

[0076] 10. The composition of any one of embodiments 1-9, which exhibits killing, paralyzing, repelling or disruption to the feeding and growth of invertebrates and / or the activity of their larvae, without affecting mammals, fish or poultry.

[0077] 11. The composition of any one of embodiments 1-10, formulated as an agrochemical formulation.

[0078] 12. The composition of embodiment 11, wherein the pesticide formulation is a wettable powder, granules, emulsifiable concentrate, spray, atomized powder, liquid, aerosol, or a micro-volume formulation that can form an emulsion or suspension by adding water.

[0079] 13. The composition of any one of embodiments 1 to 12, wherein said at least one compound of formula (I) acts as a synergist by significantly enhancing the toxicity of said insecticide.

[0080] 14. The composition of any one of embodiments 1-13, wherein said at least one compound of formula (I) is in a sublethal dose.

[0081] 15. The composition of any one of embodiments 1-14, wherein said at least one compound of formula (I) comprises pogostone.

[0082] 16. A method for killing, controlling, paralyzing, repelling, knocking down and / or hindering pests, comprising: A method comprising applying to an environment or pest in need of pest control any of the compositions described herein, including the compositions of embodiments 1-15.

[0083] 17. The method of embodiment 16, wherein the pest is an insect, an arachnid, or a larva thereof. [Example]

[0084] The following examples further detail some aspects of the embodiments of the present disclosure described above, but are not intended to limit the scope of the disclosure in any way. Those skilled in the art will appreciate that many other embodiments are within the scope of the present invention, as described and claimed herein.

[0085] Example 1 - Composition A pesticide composition containing a compound of Formula (I) in combination with an insecticide and / or enzyme inhibitor is prepared. The content of each component is in the range of about 0.01 ng to about 1 mg per unit volume, e.g., 0.01 ng, 0.1 ng, 1 ng, or 10 ng, 0.1 μg, 1 μg, or 10 μg, or 0.1 mg or 1 mg per unit volume, or within a range of any two of these values. The unit volume is in the range of 0.1 mL to 1 L, e.g., 0.1 mL, 1 mL, 10 mL, 100 mL, or 1000 mL, or within a range of any two of these values. The pesticide composition is formulated as a spray, atomizer, liquid, concentrate, dust, granule, ready-to-use formulation, or aerosol.

[0086] 1 shows the knockdown rate after 1 hour and the mortality rate after 24 hours of topical application of pogostone to female Aedes aegypti mosquitoes. The dashed line indicates the sublethal dose of pogostone used in the synergist experiment in Example 2.

[0087] Example 2 - Pest control method The following examples demonstrate the use of the composition of Example 1 in controlling pests.

[0088] The composition of Example 1 is applied directly to the environment and / or pests in need of pest control, and controls the pests at the locus of application by eradicating the pests from the environment, repelling the pests from the environment, inhibiting the growth and / or reproduction of the pests, paralyzing the pests, reducing the presence of the pests in the environment, disrupting the feeding, social behavior and / or reproduction of the pests, and / or killing the pests.

[0089] Table 1 shows the LD values ​​for adult female Aedes aegypti when each insecticide was applied alone or in combination with a sublethal dose of pogostone. 50 The synergistic ratio is the LD 50 LD of each insecticide applied in combination with pogostone 50 In all treatments with pogostone, the insecticidal effect of pogostone alone is corrected using Abbott's formula (Equation 1).

[0090] Formula 1 Correction % = (1-n T / n Co ) x 100 (where n = insect population; T = treated; Co = control) [Table 1]

[0091] Permethrin is a typical example of a pyrethroid insecticide, and dinotefuran is a typical example of a neonicotinoid insecticide.

[0092] Example 3 The KD of each compound was measured by topical application of pogostone, DDT, veratrine, or natural pyrethrin (Ceratitis graminearum) to pyrethroid-susceptible (Table 2) and pyrethroid-resistant (Table 3) strains of Aedes aegypti. 50 Value and LD 50 The value was calculated.

[0093] KD 50 = the dose required to knock down half of the individuals in the test population after a given test time.

[0094] LD 50 = the dose required to kill half of the individuals in the test population after a given test time. [Table 2] [Table 3]

[0095] Example 4 The 24-hour LD50 values ​​of pogostone and permethrin were determined for three strains of house flies and one strain of stable flies. The KS17 resistant strain shown below exhibits simultaneous resistance to organophosphates, carbamates, and synthetic pyrethroids. [Table 4]

[0096] Example 5 The 48-hour LD50 of pogostone and permethrin was determined in three strains of houseflies. The KS17-resistant strain shown below exhibits simultaneous resistance to organophosphates, carbamates, and synthetic pyrethroids. [Table 5]

[0097] Example 6 The spatial repellency of pogostone against pyrethroid-susceptible (Orlando) and pyrethroid-resistant (Puerto Rico) strains of adult female Aedes aegypti mosquitoes was evaluated. Repellency bioassays were performed using a previously described static-air repellency chamber (Schultz, 2006; Peterson, 2018). Briefly, the repellency chamber consisted of a clear glass cylindrical tube, 600 mm long and approximately 85 mm in inner diameter, placed on its side. One end of the cylindrical tube was capped with a 90 mm inner diameter glass Petri dish containing untreated 90 mm filter paper (Whatman No. 1), sealed with tape to keep it closed. The other end of the cylindrical tube was treated with 1 mL of a 0.5% (w / v) solution of monoterpenoid esters in acetone, resulting in a repellent concentration of 78.6 μg / cm on the filter paper. 2 The lid was closed in the same manner. The repellent solution was evenly applied to the filter paper at a rate that prevented the repellent from dripping off the filter paper due to acetone evaporation. The repellent solution was then left at room temperature for an additional 10 minutes to allow the acetone to evaporate before use in short-term repellency assays. For long-term repellency tests, the repellent solution was left in open air at ambient conditions for an additional 5 hours before use in the repellency assays. Immediately after attaching the filter paper to one end of the cylindrical tube, 20 (unfed) female Culex pipiens mosquitoes were anesthetized with carbon dioxide and introduced into the tube through a 20 mm hole located halfway along the length of the cylindrical tube. The hole was then sealed. This treatment was performed with minimal disruption of the air within the tube. Mosquito distribution between the treated and untreated surfaces was then observed 15, 30, 60, 90, 120, and 150 minutes after the mosquitoes were placed in the tube. The repellency ratio for Orlando or Puerto Rico strain mosquitoes was recorded as the ratio of the number of mosquitoes resting on the treated surface of the tube to the total number of mosquitoes in the tube 1 hour after the treated filter paper was placed (number of mosquitoes resting on the treated surface / total number of mosquitoes in the tube).

[0098] As shown in Figure 2, pogostone showed a significant repellent effect against both strains in this experimental assay. 50is 3.6 μg / cm 2 and EC for Puerto Rican strains. 50 is 2.5 μg / cm 2 There was no statistically significant difference in the reactivity to pogostone between these two strains. For reference, the EC50 of DEET for the Orlando strain was 50 is approximately 10 μg / cm 2 is.

[0099] Headings are provided herein for reference purposes and to facilitate locating the various sections. These headings do not limit the scope of the concepts described therein. The concepts described in each section may have applicability throughout the entire specification.

[0100] Each patent, patent application, publication, and document cited herein is incorporated by reference in its entirety. Citation of said patents, patent applications, publications, and documents is not an admission that such publications or documents are pertinent prior art, nor does it constitute an admission as to the disclosure or publication date of such publications or documents. Citation of such publications or documents does not indicate a search for the relevant disclosure. Any statements as to the publication dates or disclosure of such documents are based on available information and do not constitute an admission as to their truthfulness or accuracy.

[0101] In the foregoing description, specific details are provided for the purpose of understanding the examples. However, one skilled in the art will recognize that these examples may be practiced without the specific details.

[0102] In at least some of the above-described embodiments, one or more components used in one embodiment may be substituted for components in another embodiment, unless technically impossible. Those skilled in the art will readily appreciate that various omissions, additions, and modifications other than those described above may be made to the methods and structures described above without departing from the scope of the claimed subject matter. All such modifications and variations are deemed to be within the scope of the inventive subject matter defined in the appended claims.

[0103] Substantially all plural or singular terms used herein will be interpreted by those skilled in the art as the plural or the singular as the plural, as appropriate for the description or application herein. The various singular / plural terms have been intentionally used to clarify the invention.

[0104] The embodiments specifically described herein may be suitably practiced in the absence of elements not specifically disclosed herein. Thus, for example, in each example herein, the terms "comprising," "essentially consisting of," and "consisting of" may be interchangeable. The terms and expressions used are used for descriptive purposes and are not intended to limit the present invention. The use of such terms and expressions does not exclude the features shown or described herein or equivalents thereof, and various modifications are possible within the scope of the claims. The articles "a" and "an" may refer to one or more elements they modify (e.g., "reagent" may refer to one or more reagents) unless the context clearly dictates otherwise. In this specification, the term "about" essentially means a numerical value within 10% of the associated parameter. When the term "about" is used at the beginning of a list of numerical values, the term modifies each of the listed values. For example, a weight of "about 100 g" may include weights of 90 g to 110 g. Furthermore, when a numerical value is recited herein (e.g., about 50%, about 60%, about 70%, about 80%, about 85%, or about 86%), such numerical value recitation includes all intermediate and subvalues ​​(e.g., 54% or 85.4%). Therefore, while the present technology has been specifically disclosed in terms of exemplary embodiments and optional features, those skilled in the art may implement improvements and modifications of the concepts disclosed herein, and such improvements and modifications are considered to be within the scope of the embodiments.

[0105] Furthermore, when features or aspects of the disclosure are described in Markush format, those skilled in the art will understand that each member or subgroup of members described in Markush format is also being described.

[0106] Those skilled in the art will understand that any ranges disclosed herein, for any purpose, including providing a detailed description, encompass all possible subranges and combinations thereof. Any ranges described herein are fully descriptive, and it will be readily apparent that the invention can be practiced within such divided ranges, including at least three, four, five, ten, etc. divisions. For example, any range described herein can be readily divided into thirds, such as a low, mid, and high range, without limitation. Furthermore, those skilled in the art will understand that terms such as "less than or equal to," "at least," "greater than," and "less than" are inclusive of the recited numerical value and also refer to ranges that can be divided into subranges, as previously described. Furthermore, those skilled in the art will understand that ranges described herein are inclusive of each member. Thus, for example, a group consisting of 1 to 3 members refers to a group consisting of 1 member, a group consisting of 2 members, or a group consisting of 3 members. Similarly, a group consisting of 1 to 5 members refers to a group consisting of 1 member, a group consisting of 2 members, a group consisting of 3 members, a group consisting of 4 members, or a group consisting of 5 members, etc.

[0107] While preferred embodiments have been shown and described herein, it will be apparent to those skilled in the art that such embodiments are provided by way of example only. Those skilled in the art may make various modifications, changes, and substitutions without departing from the teachings herein. Various alternative aspects of the embodiments described herein may also be employed in practicing the embodiments described herein. The following claims define the scope of the embodiments described herein, and methods and structures within the scope of these claims and their equivalents are intended to cover such embodiments.

Claims

1. 1. A composition comprising: a. at least one compound of formula (I): b. at least one insecticide and / or at least one enzyme inhibitor; Including, 【Chemical 1】 During the ceremony, V is a substituted or unsubstituted straight or branched chain C 1 -C 12 Alkyl, substituted or unsubstituted, straight or branched chain C 2 -C 12 Alkenyl, substituted or unsubstituted straight or branched chain C 3 -C 12 Alkynyl, substituted or unsubstituted straight or branched chain C 3 -C 12 Cycloalkyl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted straight or branched chain C 3 -C 12 is cycloalkenyl; W is hydrogen or substituted or unsubstituted saturated or unsaturated C 3 -C 6 an alkane or alkene; X is an oxygen or sulfur atom; Y can be hydroxyl, sulfhydryl, amino, halogen, or alkyl of various lengths (C 1 -C 7 ) is an ether having the formula: Z is a substituted or unsubstituted straight or branched chain C 1 -C 12 Alkyl, substituted or unsubstituted, straight or branched chain C 3 -C 12 Cycloalkyl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted straight or branched chain C 3 -C 12 is cycloalkenyl; W is a substituted or unsubstituted saturated or unsaturated C 3 -C 6 optionally linked to Z via an alkane or alkene; composition.

2. 10. The composition of claim 1, wherein the at least one insecticide is a pyrethroid, a neonicotinoid, or an organophosphate.

3. 3. The composition of claim 2, wherein the pyrethroid comprises allethrin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, d-phenothrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, permethrin, fenothrin, resmethrin, sumithrin, taufluvalinate, tefluthrin, tetramethrin, or tralomethrin.

4. 3. The composition of claim 2, wherein the neonicotinoid comprises acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, or thiamethoxam.

5. The organophosphates include acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famfur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyaphos, isofenphos, O-(methoxyaminothiophosphoryl)salicylate isoform 3. The composition of claim 2, comprising isopropyl, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton methyl, parathion, parathion methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimphos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon or vamidothion.

6. 2. The composition of claim 1, wherein the at least one enzyme inhibitor is a glutathione-S-transferase inhibitor, a mixed function oxidase inhibitor, or an esterase inhibitor.

7. 7. The composition of claim 6, wherein the glutathione-S-transferase inhibitor comprises diethyl maleate, quercetin, or tannic acid.

8. 7. The composition of claim 6, wherein the mixed function oxidase inhibitor comprises piperonyl butoxide, isoniazid, SKF 525A, or MGK 264.

9. 7. The composition of claim 6, wherein the esterase inhibitor comprises S,S,S-tributyl phosphorotrithioate, iprobenfos, or triphenyl phosphate.

10. 10. The composition of claim 1, which kills, paralyzes, repels or disrupts the feeding and growth of invertebrates and / or the activity of their larvae without affecting mammals, fish or poultry.

11. 10. The composition of claim 1 formulated as a pesticide formulation.

12. 12. The composition according to claim 11, wherein the pesticide formulation is a wettable powder, granules, emulsifiable concentrate, spray, atomized powder, liquid, aerosol, or an ultra-trace amount formulation that can form an emulsion or suspension by adding water.

13. 10. The composition of claim 1, wherein said at least one compound of formula (I) acts as a synergist by significantly enhancing the toxicity of said insecticide.

14. 10. The composition of claim 1, wherein the at least one compound of formula (I) is in a sublethal dose.

15. The composition of claim 1 , wherein the at least one compound of formula (I) comprises pogostone.

16. 1. A method for killing, controlling, paralyzing, repelling, knocking down and / or hindering pests, comprising:

10. A method comprising the step of applying the composition of claim 1 to an environment or pest in need of pest control.

17. 17. The method of claim 16, wherein the pest is an insect, an arachnid, or a larva thereof.

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