Pest control composition

Incorporating cyclic terpenoids in pest control compositions addresses solubility issues of pyrethroid compounds in aliphatic hydrocarbons, ensuring solubility and preventing precipitation.

JP7764133B2Active Publication Date: 2025-11-05EARTH CORP
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Patent Information

Application Number
JP2021031992
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Filing Date
2021-03-01
Publication Date
2025-11-05
Estimated Expiration
2041-03-01

AI Technical Summary

Technical Problem

Certain pyrethroid compounds, such as cyfluthrin and momfluorothrin, exhibit low solubility in aliphatic hydrocarbons, leading to precipitation issues in pest control compositions.

Method used

Incorporating a specific amount of cyclic terpenoids into the pest control composition, with a mass ratio of 0.6 or more relative to the pyrethroid compound, enhances solubility in aliphatic hydrocarbons.

Benefits of technology

Ensures solubility of pyrethroid compounds without precipitation, maintaining effective pest control performance.

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Abstract

To provide an insect pest control composition which sufficiently secures solubility of a pyrethroid compound in aliphatic hydrocarbon without causing precipitates even when a pyrethroid compound hardly soluble in aliphatic hydrocarbon is used.SOLUTION: An insect pest control composition contains a pyrethroid compound hardly soluble in aliphatic hydrocarbon (A), cyclic terpenoid (B), and 5-17C aliphatic hydrocarbon (C), and has a mass ratio of the pyrethroid compound hardly soluble in aliphatic hydrocarbon (A) to the cyclic terpenoid (B) of 0.6 or more.SELECTED DRAWING: None
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Description

[Technical Field]

[0001] The present invention relates to a pest control composition. [Background technology]

[0002] Pest control compositions contain, as active ingredients, pest control components that exhibit a control effect against pests, and are applied to a wide range of targets, including humans, livestock, pets, agricultural products, homes, etc. Examples of pest control components include pyrethroid compounds, carbamate compounds, and organophosphorus compounds.

[0003] Pest control compositions are used in various formulations depending on the intended use. For example, pest control compositions are used as liquid agents, aerosol agents, etc. In such cases, in order to improve the fluidity of the pest control composition and prevent crystallization, it has been conventional to dissolve the pest control component in a solvent such as an aliphatic hydrocarbon.

[0004] For example, Patent Documents 1 and 2 disclose the use of an aliphatic hydrocarbon as a solvent for a pyrethroid compound. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2014-062086 [Patent Document 2] Japanese Patent Application Publication No. 2018-095577 Summary of the Invention [Problem to be solved by the invention]

[0006] However, the inventors' investigations have revealed that certain pyrethroid compounds (e.g., cyfluthrin, momfluorothrin, pyrethrins, etc.) have low solubility in aliphatic hydrocarbons, which can cause problems such as precipitation in the pest control composition.

[0007] The present invention has been made in view of the above-mentioned conventional circumstances, and an object to be achieved by the present invention is to provide a pest control composition that does not produce precipitates and that sufficiently ensures the solubility of the pyrethroid compound in aliphatic hydrocarbons, even when the pyrethroid compound is sparingly soluble in aliphatic hydrocarbons as described above. [Means for solving the problem]

[0008] As a result of extensive research to solve the above problems, the inventors discovered that the above problems can be solved by incorporating a specific amount of cyclic terpenoid into a pest control composition, and thus completed the present invention.

[0009] That is, the present invention provides the following <1> ~ <3> It is related to. <1> The composition contains an aliphatic hydrocarbon poorly soluble pyrethroid compound (A), a cyclic terpenoid (B), and an aliphatic hydrocarbon having 5 to 17 carbon atoms (C), A pest control composition, wherein the mass ratio of the cyclic terpenoid (B) to the sparingly soluble aliphatic hydrocarbon pyrethroid compound (A) is 0.6 or more. <2> The aliphatic hydrocarbon poorly soluble pyrethroid compound (A) is at least one selected from the group consisting of cyfluthrin, momfluorothrin, and pyrethrins. <1> The pest control composition according to claim 1. <3> The cyclic terpenoid (B) is at least one selected from the group consisting of menthone, menthol, carvone, thymol, pulegone, p-menthane-3,8-diol, 1,8-cineole, pinene, and thujone. <1> or <2> The pest control composition according to claim 1. [Effects of the Invention]

[0010] Even when a pyrethroid compound that is poorly soluble in aliphatic hydrocarbons is used in the pest control composition of the present invention, no precipitate is formed and the solubility of the pyrethroid compound in aliphatic hydrocarbons can be sufficiently ensured. DETAILED DESCRIPTION OF THE INVENTION

[0011] The present invention will be described in detail below, but these are examples of preferred embodiments, and the present invention is not limited to these details.

[0012] The pest control composition of the present invention contains an aliphatic hydrocarbon poorly soluble pyrethroid compound (A) (hereinafter, may be referred to as "poorly soluble pyrethroid compound (A)"), a cyclic terpenoid (B), and an aliphatic hydrocarbon having 5 to 17 carbon atoms (C).

[0013] The content of the poorly soluble pyrethroid compound (A) in the pest control composition of the present invention is preferably 0.001 w / v% or more, more preferably 0.01 w / v% or more, and even more preferably 0.1 w / v% or more, and preferably 5 w / v% or less, more preferably 3 w / v% or less, and even more preferably 1.5 w / v% or less.

[0014] When the content is 0.001 w / v% or more, a sufficient pest control effect can be obtained, and when the content is 5 w / v% or less, significant solubility can be ensured and stickiness can be suppressed.

[0015] Specific examples of the poorly soluble pyrethroid compound (A) include cyfluthrin, momfluorothrin, pyrethrins, etc. These may be used singly or in combination of two or more.

[0016] The cyclic terpenoid (B) is a cyclic compound whose constituent unit is an isoprene unit, which is a five-carbon compound. In the pest control composition of the present invention, the mass ratio of the cyclic terpenoid (B) to the poorly soluble pyrethroid compound (A) (mass of cyclic terpenoid (B) / mass of poorly soluble pyrethroid compound (A): hereinafter sometimes referred to as the "mass ratio (B) / (A)") is 0.6 or more.

[0017] When the mass ratio (B) / (A) is 0.6 or more, it is believed that the solubility of the poorly soluble pyrethroid compound (A) in the aliphatic hydrocarbon (C) is improved.

[0018] The mass ratio (B) / (A) is preferably from 0.6 to 20, more preferably from 0.8 to 10, and even more preferably from 1 to 5, from the viewpoint of the solubility of the poorly soluble pyrethroid compound (A).

[0019] Specific examples of the cyclic terpenoid (B) include menthone, menthol, carvone, thymol, pulegone, p-menthane-3,8-diol, 1,8-cineole, pinene, thujone, limonene, terpinene, terpinolene, phellandrene, camphene, 3-carene, caryophyllene, (+)-valencene, thujopsene, cedrene, longifolene, (+)-neoiso-isopulegol, isopulegol, terpineol, 1-terpinen-4-ol, ionone, irone, methylionone, isomethylionone, allylionone, pseudoionone, n-methylpseudoionone, isomethylpseudoionone, damascone, β-damascenone, nootkatone, cedryl methyl ketone, α-terpinyl acetate, nopyr acetate, and ximylic acetate. These may be used alone or in combination of two or more.

[0020] Among these, from the viewpoint of the solubility of the poorly soluble pyrethroid compound (A), menthone, menthol, carvone, thymol, pulegone, p-menthane-3,8-diol, 1,8-cineole, pinene, and thujone are preferred, and menthone, carvone, pulegone, and 1,8-cineole are more preferred.

[0021] The content of the cyclic terpenoid (B) in the pest control composition of the present invention is preferably 0.01 w / v% or more, more preferably 0.05 w / v% or more, and even more preferably 0.1 w / v% or more, and preferably 20 w / v% or less, more preferably 10 w / v% or less, and even more preferably 5 w / v% or less.

[0022] When the content is 0.01 w / v% or more, the mass ratio (B) / (A) can be 0.6 or more even when a sufficient amount of the poorly soluble pyrethroid compound (A) is used to obtain a pest control effect. Furthermore, when the content is 20 w / v% or less, the odor characteristic of the cyclic terpenoid (B) can be suppressed, making it easy to use as a pest control composition.

[0023] The aliphatic hydrocarbon (C) has 5 to 17 carbon atoms, preferably 8 to 16 carbon atoms, and more preferably 9 to 15 carbon atoms.

[0024] When the aliphatic hydrocarbon (C) has 5 to 17 carbon atoms, the aliphatic hydrocarbon (C) becomes liquid at room temperature and normal pressure (25°C, 1 atmosphere) and is suitable as a solvent in the pest control composition.

[0025] Examples of the aliphatic hydrocarbon (C) include normal paraffin and isoparaffin.

[0026] Specific examples of normal paraffins include normal pentane, normal hexane, normal heptane, normal octane, normal nonane, normal decane, normal undecane, normal dodecane, normal tridecane, normal tetradecane, normal pentadecane, normal hexadecane, and normal heptadecane.

[0027] Specific examples of isoparaffins include isopentane, 2-methylpentane, 3-methylpentane, 2,2-dimethylbutane, 2-methylhexane, 3-ethylpentane, 2,2-dimethylpentane, 2,3-dimethylpentane, 2-methylheptane, 2-methyloctane, 2,3,4-trimethylpentane, 2-methylnonane, 2-methyldecane, 2-methylundecane, 2-methyldodecane, 2-methyltridecane, 2-methyltetradecane, 2-methylpentadecane, and 2-methylhexadecane.

[0028] The aliphatic hydrocarbon (C) may be any of a single normal paraffin, a single isoparaffin, a mixture of multiple normal paraffins, a mixture of multiple isoparaffins, a mixture of multiple normal paraffins and a single isoparaffin, a mixture of a single normal paraffin and multiple isoparaffins, and a mixture of multiple normal paraffins and multiple isoparaffins. When the aliphatic hydrocarbon (C) is a mixture, the mixing ratio of each paraffin is not particularly limited.

[0029] The content of the aliphatic hydrocarbon (C) in the pest control composition of the present invention is preferably 50 w / v % or more, more preferably 60 w / v % or more, and even more preferably 65 w / v % or more.

[0030] When the content is 50 w / v % or more, the solubility of the poorly soluble pyrethroid compound (A) can be improved.

[0031] Preferably, the pest control composition of the present invention further contains a solubilizing agent. Examples of the solubilizing agent include carbonate esters such as propylene carbonate, ethylene carbonate, and butylene carbonate; alcohols such as ethanol, isopropyl alcohol, lauryl alcohol, cetanol, 2-hexyldecanol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, and lanolin alcohol; and higher fatty acid esters such as isopropyl myristate, butyl myristate, hexyl laurate, and isopropyl palmitate.

[0032] The content of the solubilizing agent in the pest control composition of the present invention is preferably 0.01 to 20 w / v%, more preferably 0.05 to 10 w / v%, and even more preferably 0.1 to 5 w / v%, from the viewpoint of the solubility of the poorly soluble pyrethroid compound (A).

[0033] The pest control composition of the present invention may contain other ingredients as long as the effects of the present invention are achieved.

[0034] Other ingredients that can be used include disinfectants, antifungals, preservatives, deodorizers, ultraviolet absorbers, ultraviolet scattering agents, dispersants, antioxidants, thickeners, fragrances, colorants, stabilizers, and the like.

[0035] The pest control composition of the present invention can be obtained, for example, by mixing and stirring the above-mentioned components, and may be heated, etc., if desired. The contents of the above-mentioned components can be appropriately adjusted.

[0036] The pest control composition of the present invention can be used in various formulations such as pump formulations, aerosol formulations, lotions, wet tissue formulations, roll-ons, liniments, gel formulations, and cream formulations.

[0037] To prepare these formulations, for example, a pest control composition is prepared using the above-mentioned components, and then, if necessary, combined with a pump device, aerosol device, nonwoven fabric, applicator, etc. to form the desired formulation.

[0038] The target pests in the present invention are not particularly limited as long as the effects of the invention are achieved, but examples include mosquitoes, black flies, horseflies, fleas, house mites, ticks, flies, bedbugs, leeches, cockroaches, centipedes, millipedes, house centipedes, pill bugs, woodlice, ants, spiders, wasps, moths, midges, leafhoppers, stink bugs, caterpillars, termites, fruit flies, and moth flies. [Example]

[0039] The present invention will be specifically explained below with reference to examples, but the present invention is not limited to these examples in any way.

[0040] As normal paraffin, "Neothiozol" (carbon number: 11 to 15) manufactured by Sanko Chemical Industry Co., Ltd. was used, and as isoparaffin, "IP Clean LX" (carbon number: 10 to 13) manufactured by Idemitsu Kosan Co., Ltd. was used.

[0041] [Test Example 1] <Examples 1-1 to 1-12, Comparative Examples 1-1 to 1-5> A cyclic terpenoid was dissolved in a pyrethroid compound according to the formulation shown in Table 1. Then, the other ingredients shown in Table 1 (solubilizer, aliphatic hydrocarbon) were added and dissolved to prepare 100 mL of a pest control composition.

[0042] The cyfluthrin used was preheated to 60°C. Since menthol and thymol are solids, they were partially dissolved in normal paraffin before use. (Amount of normal paraffin used beforehand: 0.5 g in Example 1-2, 0.75 g in Example 1-3, 1 g in Example 1-4, 10 g in Example 1-6, 0.05 g in Comparative Example 1-2, 0.1 g in Comparative Example 1-3, and 0.25 g in Comparative Example 1-4)

[0043] The resulting pest control compositions were left to stand in an environment of 25° C. for 24 hours and then visually evaluated according to the following criteria. The results are shown in Table 1. ◯: No precipitate was found in the pest control composition. ×: Sediment was found in the pest control composition.

[0044] [Table 1]

[0045] [Test Example 2] <Examples 2-1 to 2-3, Comparative Examples 2-1 to 2-2> A cyclic terpenoid was dissolved in an amount of "Sumifreeze" (manufactured by Sumitomo Chemical Co., Ltd.) containing 0.25 g of momfluorotrin according to the formulation shown in Table 2. Then, the other ingredients (solubilizer, aliphatic hydrocarbon) shown in Table 2 were added and dissolved to prepare 100 mL of a pest control composition. The obtained pest control composition was evaluated in the same manner as in Test Example 1. The results are shown in Table 2.

[0046] [Table 2]

[0047] [Test Example 3] <Examples 3-1 to 3-3, Comparative Examples 3-1 to 3-2> According to the method described in Test Example 1, 100 mL of a pest control composition was prepared according to the formulation shown in Table 3. The obtained pest control composition was evaluated in the same manner as in Test Example 1. The results are shown in Table 3.

[0048] [Table 3]

[0049] [Test Example 4] <Reference example 1-1~1-2> According to the method described in Test Example 1, 100 mL of a pest control composition was prepared according to the formulation shown in Table 4. The obtained pest control composition was evaluated in the same manner as in Test Example 1. The results are shown in Table 4.

[0050] [Table 4]

[0051] The results in Tables 1 to 3 show that by using a cyclic terpenoid in an amount such that the mass ratio to the pyrethroid compound poorly soluble in aliphatic hydrocarbons is 0.6 or more, the pyrethroid compound dissolves in the aliphatic hydrocarbons without forming any precipitate.

[0052] On the other hand, the results in Table 4 show that imiprothrin also has low solubility in aliphatic hydrocarbons. However, even when cyclic terpenoids were used in an amount in which the mass ratio to imiprothrin was 0.6 or more, imiprothrin did not dissolve in aliphatic hydrocarbons, and a precipitate formed.

Claims

1. The composition contains an aliphatic hydrocarbon poorly soluble pyrethroid compound (A), a cyclic terpenoid (B), and an aliphatic hydrocarbon having 5 to 17 carbon atoms (C), a mass ratio of the cyclic terpenoid (B) to the poorly soluble aliphatic hydrocarbon pyrethroid compound (A) is 0.6 to 20; the poorly soluble aliphatic hydrocarbon pyrethroid compound (A) is at least one selected from the group consisting of cyfluthrin, momfluorothrin, and pyrethrins, The pest control composition, wherein the aliphatic hydrocarbon (C) having 5 to 17 carbon atoms is normal paraffin or isoparaffin.

2. The pest control composition according to claim 1, wherein the cyclic terpenoid (B) is at least one selected from the group consisting of menthone, menthol, carvone, thymol, pulegone, p-menthane-3,8-diol, 1,8-cineole, pinene, and thujone.

Citation Information

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