JP2000319105A - Resin preparation for controlling insect pest - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject preparation capable of containing a large amount of a chemical and freely controlling a slow releasing rate by making the preparation include a resin, an insect pest controlling component and a reaction product of a bisoxazoline compound and a long-chain alkyl group-containing compound as a slow releasing controller. SOLUTION: This preparation comprises (A) a resin, preferably an olefinic resin such as a polyethylene, etc., (B) an insect pest controlling component such as one selected from an insecticide (e.g. pyrethrin, etc.), a mothball, an insect growth regulator (e.g. methoprene, etc.), and a repellent (e.g. deet, etc.), and (C) a reaction product of a bisoxazoline compound preferably of the formula [D is a (substituted) alkylene, a cycloalkylene or the like; R1 to R3 are each H, a (substituted) alkyl or an aryl] [e.g. 1,6-bis(1,3-oxazolin-2-yl)hexane, etc.], and a long-chain alkyl group-containing compound (e.g. lauric acid, palmitic acid, etc.), as a slow releasing controller.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a resin formulation for controlling insect pests, and more particularly, to adding a specific sustained-release controlling agent to a resin to increase the amount of a component for controlling insect pests, and to reduce the amount of a component for controlling insect pests. The present invention relates to a pest control resin formulation whose release rate can be freely controlled.

[0002]

2. Description of the Related Art Sustained-release preparations comprising a resin as a matrix and various agents mixed therein are disclosed in JP-A-1-230504, JP-A-3-200704 and JP-A-6-32.
No. 5332, JP-A-7-041402, and JP-A-9-281603. For example, Japanese Patent Application Laid-Open No. 9-281603 discloses a sustained-release resin formulation in which a drug solution is mixed with a resin, and as the solvent evaporates, the drug is separated from the solution and gradually released from the resin formulation. ing. However, in this formulation,
The amount of the drug is limited by the amount dissolved in the solvent,
The sustained release rate depends on the solvent evaporation rate. Therefore, the drug content cannot be increased beyond a certain level, and the drug release period can be adjusted only in a narrow range.

[0003]

DISCLOSURE OF THE INVENTION The object of the present invention is to provide a pest-controlling resin preparation which can contain a larger amount of drug than conventional sustained-release resin preparations and which can freely control the sustained-release rate. It is.

[0004]

The object of the present invention is to provide, as a resin, a component for controlling insect pests, and a reaction product of a bisoxazoline compound and a compound having a long-chain alkyl group as a sustained-release controlling agent. It can be solved by a resin formulation for controlling insect pests.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION Each component constituting the resin formulation for controlling insect pests of the present invention will be described below. The following thermoplastic resins can be exemplified as the resin serving as the matrix of the resin preparation. 1) Olefin resin 1.1) Ethylene resin Low density polyethylene, ultra-low density polyethylene, linear low density polyethylene, high density polyethylene, ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, ethylene ionomer resin 1 .2) Propylene-based polymer polypropylene, ethylene-propylene random copolymer, ethylene-propylene block copolymer 2) polyvinyl chloride 3) thermoplastic elastomer olefin-based thermoplastic elastomer, styrene-based thermoplastic elastomer Among these, olefin-based resins are preferred.

[0006] Insect-controlling ingredients The matrix-resin-containing pest-controlling ingredients include:
Conventionally used drugs can be used. Examples of such agents are given below. Pyrethroid insecticides,
Organophosphorus insecticides, carbamate insecticides, organochlorine insecticides, insect growth regulators (IGR: Insect Growth Regula)
tors), repellents and the like, or a mixture of two or more thereof.

[0007] Specific examples of these drugs are as follows. 1. Pyrethroid insecticides pyrethrin, arethrin, tetramethrin, resmethrin, pramethrin, permethrin, cypermethrin, phenothrin, cyphenothrin, deltamethrin, tralomethrin, bifenthrin, fenvalerate, cyfluthrin, cyhalothrin, etofenproxin, promiproline, imiprothrine ,
Empentrin, pyrethrum extract, framethrin and the like. 2. Organophosphorus pesticides diazinon, DDVP, fenitrothion, malathion, chlorpyrifosmethyl, temefos, fenthion,
Trichlorfon, pyridafenthion, prothiophos,
Propetanphos, tetrachlorvinphos and the like.

[0008] 3. Carbamate insecticide propoxur, benziocarb, carbaryl, methoxadiazone, BPMC and the like. 4. Repellent Deet etc. 5. Insect growth regulator (IGR) pyriproxyfen, methoprene, cyromazine, diflubenzuron, lufenuron, phenoxycarb and the like. In addition, the pest control component is not limited to the above-mentioned chemicals, and any of those used in the art can be used.

[0009] In addition to these drugs, auxiliary ingredients such as synergists for enhancing the efficacy of the drugs can be added. Synergists include piperonyl butoxide, MG
K-264 and IBTA can be exemplified.

[0010] In the sustained-release controlling agent present invention, as a sustained release controlling agent, for use the bisoxazoline compound, the reaction products of compounds having a long chain alkyl group.

Specifically, the sustained-release controlling agent used in the present invention comprises a long-chain alkyl group and a functional group containing an active hydrogen atom (for example, a hydroxyl group, a mercapto group, a carboxyl group, an amino group, etc.). Having the compound (1) having the following formula (I)

[0012]

Embedded image (Wherein D is an alkylene group which may have a substituent,
A cycloalkylene group which may have a substituent or an arylene group which may have a substituent; R ¹ , R ² ,
R ³ and R ⁴ are the same or different and each represent a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent. ) To produce a compound having an oxazoline group.

Long-chain alkyl group-containing compound (1) The long-chain alkyl group-containing compound (1) may be a low molecular weight compound or a high molecular weight compound (polymer) as long as it has a long chain alkyl group. . The high molecular weight compound also includes a polymer in an oligomer region having a relatively small molecular weight. Here, the long-chain alkyl group means at least 4, preferably at least 6, more preferably at least 8
Means an alkyl group having 5 carbon atoms. Preferred examples of the long-chain alkyl group include butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl,
Undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and the like.

The "functionality containing an active hydrogen atom" of the compound having a long-chain alkyl group includes, for example, a hydroxyl group which may be phenolic, a mercapto group, a carboxyl group and an amino group. The long-chain alkyl group-containing compound may have a single type of functional group, or may have a plurality of different functional groups. Preferred functional groups are those having a high activity for oxazoline, for example,
Carboxyl groups and amino groups, especially carboxyl groups.

The low-molecular-weight long-chain alkyl group-containing compound (1
a) As the low-molecular-weight long-chain alkyl group-containing compound (1a),
A low-volatile compound which is liquid or solid at ordinary temperature (for example, a non-volatile compound having a boiling point of 150 ° C. or more at ordinary pressure) is generally used, and its molecular weight is usually 1,000 or less, preferably 100 to 750, and more preferably. Is about 150 to 750. Generally, the main chain of such a compound is composed of an alkyl group having 6 to 30 carbon atoms, preferably 8 to 26 carbon atoms, and more preferably about 10 to 24 carbon atoms.

Examples of the low-molecular-weight, long-chain alkyl group-containing compound having a hydroxyl group include aliphatic alcohols having about 10 to 30 carbon atoms (eg, lauryl alcohol, tetradecyl alcohol, cetyl alcohol, octadecyl alcohol, aralkyl alcohol, ceryl alcohol). alcohol,
Merisyl alcohol, oleyl alcohol, etc.), 1,
Aliphatic diols having about 4 to 10 carbon atoms such as 4-butanediol and 1,6-hexanediol, and compounds having a phenolic hydroxyl group (e.g., alkylphenols (e.g., an alkyl moiety having 4 to 20 carbon atoms, preferably And alkylphenols having about 8 to 14 carbon atoms). Preferred hydrophobic low molecular weight compounds are compounds having a phenolic hydroxyl group, such as the aforementioned alkylphenols.

Examples of the low-molecular-weight long-chain alkyl group-containing compound having a mercapto group include thioalcohols corresponding to the aliphatic alcohols.

Examples of the low-molecular-weight long-chain alkyl group-containing compound having a carboxyl group include carboxylic acids having 6 or more carbon atoms, for example, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid. Acid, dioxystearic acid, behenic acid, saturated fatty acid having 6 to 30 carbon atoms such as montanic acid, lindelic acid,
Palmito oleic acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, eleostearic acid, arachidonic acid, unsaturated fatty acids having 10 to 25 carbon atoms such as erucic acid,
4 to 40 carbon atoms such as malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, azelaic acid and sebacic acid
Of saturated polycarboxylic acids, maleic acid, maleic anhydride,
Examples include unsaturated polycarboxylic acids such as fumaric acid, citraconic acid, itaconic acid, and glutaconic acid, and dimer acids. These carboxylic acids can be used alone or in combination of two or more. Among these carboxylic acids, carboxylic acids having 6 or more carbon atoms, particularly aliphatic monocarboxylic acids, among them, higher fatty acids are preferably used. The carbon number of the higher fatty acid is, for example, preferably about 10 to 26 carbon atoms, particularly preferably about 12 to 24 carbon atoms. The higher fatty acid may be an unsaturated higher fatty acid, but a saturated higher fatty acid is advantageously used.

Examples of the low-molecular-weight long-chain alkyl group-containing compound having an amino group include primary amines such as caprylamine, laurylamine, myristylamine, palmitylamine, stearylamine and oleylamine;
Examples thereof include secondary amines such as didecylamine, didodecylamine, ditetradecylamine, dihexadecylamine and dioctadecylamine, and diamines such as hexamethylenediamine. Preferred amine compounds include higher amines having 10 to 26 carbon atoms, preferably 12 to 24 carbon atoms, more preferably 12 to 18 carbon atoms, particularly primary amines. These amine compounds can be used alone or in combination of two or more.

Furthermore, the compound having a long-chain alkyl group having a low molecular weight includes a compound having a different functional group, for example, a compound having a carboxyl group and an amino group, a compound having a carboxyl group and a hydroxyl group, and the like. It is. Such compounds include, for example, aminocarboxylic acids having about 6 to 18 carbon atoms, such as aminocaproic acid and aminoundecanoic acid.

Two or more of these low-molecular-weight long-chain alkyl group-containing compounds (1a) may be used in combination.

High-molecular-weight long-chain alkyl group-containing compound (polymer) (1b) The high-molecular-weight long-chain alkyl group-containing compound (1b) may be a linear or branched high-molecular compound. The type of the polymer is not particularly limited, but a preferred polymer is an olefin-based polymer.

The olefin polymer includes, for example, olefins such as ethylene, propylene, 1-butene, isobutene, 1-pentene and 4-methyl-1-pentene;
It can be obtained from ethylenically unsaturated monomers such as dienes such as 3-butadiene and isoprene.

The polymer having a long-chain alkyl group is not limited to a homopolymer or a copolymer of the above-mentioned polymerizable monomer, but may be a copolymer of the above-mentioned polymerizable monomer and a copolymerizable monomer. There may be. The polymerization form of the copolymer is not particularly limited, and may be any of a random polymer, a block copolymer, a graft copolymer, and the like. Examples of copolymerizable monomers include, for example, acrylic monomers such as acrylates, methacrylates, and acrylonitrile; vinyl acetate;
Vinyl ester monomers such as vinyl propionate; styrene, α-methylstyrene and the like. The copolymerizable monomers can be used alone or in combination of two or more.

Specific examples of the above polymer include polyethylene, polypropylene, ethylene-propylene copolymer, ethylene-propylene-diene copolymer, ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, polybutene, Olefin polymers such as polybutadiene, acrylonitrile-butadiene copolymer, polyisobutylene, polyisoprene, and polymethylpentene; styrene polymers such as styrene-butadiene copolymer, styrene-acrylonitrile-butadiene copolymer, and hydrogenated products thereof And the like.

Although the molecular weight of the high molecular compound (1b) is not particularly limited, it is advantageous that the molecular weight is relatively low in order to exert an effect by adding a small amount. Such low molecular weight polymers include low molecular weight polyethylene, low molecular weight polypropylene, liquid polypropylene, liquid polybutadiene,
Low molecular weight or liquid polyolefins such as polybutene, liquid polyisobutylene, and liquid butyl rubber; low molecular weight styrene-based polymers; and hydrogenated products thereof. Particularly preferred polymers are olefin-based polymers such as polyethylene.

Such a long chain alkyl group-containing polymer compound has a functional group containing an active hydrogen atom, for example, a hydroxyl group, a mercapto group, a carboxyl group, an amino group, etc., like the low molecular weight compound described above. Have. Such a functional group is obtained by copolymerizing an ethylenically unsaturated monomer and, if necessary, a copolymerizable monomer with a monomer having a hydroxyl group, a mercapto group, a carboxyl group or an amino group. Can be introduced into the main chain of the polymer compound. Further, these functional groups can be introduced by a polymer reaction of a polymer having a long-chain alkyl group.

The monomer having a hydroxyl group includes, for example, allyl alcohol, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate and the like. In the monomer having a mercapto group,
Compounds corresponding to the above-mentioned monomers having a hydroxyl group are included.

Examples of the monomer having a carboxyl group include acrylic acid, methacrylic acid, maleic acid, itaconic acid, crotonic acid, 10-undecylenic acid, vinylbenzoic acid, 5-norbornene-2-carboxylic acid, and maleic anhydride. Includes ethylenically unsaturated carboxylic acids such as acids and their anhydrides. The monomer having an amino group includes aminostyrene, vinylamine, allylamine and the like. Preferred monomers include carboxyl and amino groups, especially carboxyl groups.

Examples of the polymer into which a carboxyl group has been introduced by a copolymerization reaction include a modified polyolefin, for example,
Ethylene- (meth) acrylic acid copolymer, propylene-
(Meth) acrylic acid copolymer, carboxyl-modified polyolefin (for example, ethylene-maleic anhydride copolymer,
Ethylene- (meth) acrylic acid-maleic anhydride copolymer).

As a method for introducing a hydroxyl group, a carboxyl group, and an amino group by a polymer reaction, a conventional method can be adopted. For example, a hydroxyl group can be introduced by a copolymerization and hydrolysis reaction of vinyl acetate or ethylene carbonate, a reduction reaction of a carbonyl group or a carboxyl group generated by an oxidation reaction of an olefin-based polymer, and the polymer has an unsaturated bond. In this case, it can be introduced by introduction of phenol by Friedel-Crafts reaction or introduction of acetic acid by Friedel-Crafts reaction and hydrolysis reaction. The carboxyl group can be introduced by an oxidation reaction, a thermal decomposition reaction, a heat treatment using a peroxide, or a reaction with maleic anhydride in the presence of a peroxide when the polymer has an unsaturated bond. The amino group can be introduced by copolymerization of N-vinylformamide and a hydrolysis reaction. Alternatively, it can be produced by converting a polymer having a carboxyl group into an acid chloride and reacting with a diamine such as p-phenylenediamine.

Although the molecular weight of the above polymer is not particularly limited, for example, the weight average molecular weight is 500 to 250,000, preferably 700 to 100,000, and more preferably 10 to 100,000.
It is about 00 to 25000. Particularly preferred polymers include those having a molecular weight of about 1,000 to 25,000 (for example, a molecular weight of 1,000 to 10,000, preferably 1,000 to 5,000).
) Of relatively low molecular weight polymers.

Bisoxazoline compound (2) Bisoxazoline compound (2) represented by the above formula (I)
In the above, as the alkylene group for D, for example, C _1-10
Alkylene groups (eg, methylene, ethylene, trimethylene, propylene, tetramethylene, pentamethylene,
A hexamethylene group). The cycloalkylene group includes, for example, a C _5-10 cycloalkylene group (eg, 1,3-cyclopentylene, 1,3-cyclohexylene, 1,4-cyclohexylene group, and the like). The arylene group includes a C _6-12 arylene group (for example,
1,3-phenylene, 1,4-phenylene, 1,5-naphthylene, a 2,5-naphthylene group, etc.).

The alkylene group, cycloalkylene group and arylene group may have at least one substituent. Examples of such a substituent include a halogen atom (eg, fluorine, chlorine, bromine atom, etc.) and an alkyl group (eg, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, etc.) And an alkoxy group (for example, an alkoxy group having about 1 to 6 carbon atoms such as methoxy, ethoxy, propoxy, isopropoxy, and butoxy).

The preferred group D includes an optionally substituted aryl group, particularly an optionally substituted phenylene group (for example, a 1,3-phenylene group or a 1,4-phenylene group, etc.). ) Is included.

In the above formula (I), the alkyl groups represented by R ¹ , R ² , R ³ and R ⁴ include, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl,
Examples thereof include C _1-10 alkyl groups such as s-butyl, t-butyl, pentyl, and hexyl groups. Preferred alkyl groups include lower alkyl groups having about 1 to 6 carbon atoms, particularly 1 to 6 carbon atoms.
And 4 lower alkyl groups (for example, especially a methyl group, an ethyl group, a propyl group, an isopropyl group, etc.). The aryl group includes a phenyl, 1-naphthyl, 2-naphthyl group and the like.

These alkyl groups and aryl groups may have a substituent. In the alkyl group having a substituent,
For example, dichloromethyl, trichloromethyl, trifluoromethyl, 2,2,2-trichloroethyl, 2,2,2-
And halogenated C1-4 alkyl groups such as trifluoroethyl and pentafluoroethyl.

The aryl group having a substituent includes, for example,
A phenyl group having a halogen atom such as 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3,5-dichlorophenyl group, 2
C _1-4 alkyl such as -methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 3,5-dimethylphenyl, 4-ethylphenyl,
Phenyl group and the like - a phenyl group, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,4-dimethoxyphenyl, 3,5-dimethoxyphenyl, C _{1 -4} alkoxy, such as 4-ethoxyphenyl group Can be

Preferred R ¹ , R ² , R ³ and R ⁴ include a hydrogen atom or a C _1-4 alkyl group. In particular, at least ^one of R ¹ and R ² (particularly R ² ) is a hydrogen atom, R ³ and R ⁴
It is preferred that at least one (particularly R ⁴ ) is a hydrogen atom. More preferably, R ¹ , R ² , R ³ and R ⁴ are all hydrogen atoms.

Preferred bisoxazoline compounds include compounds represented by the following formula (Ia).

Embedded image (In the formula, R ¹ , R ² , R ³ and R ⁴ are the same or different and each represent a hydrogen atom or a C _1-4 alkyl group.) In particular, R ¹ , R ² , R ³ and R ⁴ are each a hydrogen atom The compound represented by the above formula (Ia) is preferable.

Specific examples of preferred compounds among the compounds represented by the above formula (I) are as follows: 1,6-bis (1,3-oxazoly-2-yl) hexane, 1,8- Bis (1,3-oxazoli-2-yl) octane, 1,10
-Bis (1,3-oxazoli-2-yl) decane, 1,3
-Bis (1,3-oxazoly-2-yl) cyclohexane, 1,4-bis (1,3-oxazoly-2-yl) cyclohexane, 2,2 ′-(1,3-phenylene) -bis (2- Oxazoline), 2,2 '-(1,4-phenylene) -bis (2-oxazoline), 2,2'-(1,2-
Phenylene) -bis (2-oxazoline), 2,2'-
(1,3-phenylene) -bis (4-methyl-2-oxazoline), 2,2 ′-(1,4-phenylene) -bis (4-methyl-2-oxazoline), 2,2 ′-(1 , 2
-Phenylene) -bis (5-methyl-2-oxazoline), 2,2 ′-(1,3-phenylene) -bis (5-methyl-2-oxazoline), 2,2 ′-(1,4-phenylene ) -Bis (5-methyl-2-oxazoline), 2,
2 ′-(1,3-phenylene) -bis (4-methylphenyl-2-oxazoline), 2,2 ′-(1,4-phenylene) -bis (4-methylphenyl-2-oxazoline), 2, 2 '-(1,3-phenylene) -bis (4-chlorophenyl-2-oxazoline), 2,2'-(1,4
-Phenylene) -bis (4-chlorophenyl-2-oxazoline) and the like. The bisoxazoline compounds represented by the formula (I) can be used alone or in combination of two or more.

The bisoxazoline compound (2) can be produced by a conventional method, for example, by reacting a fatty acid or its methyl ester with ethanolamine in the presence of a catalyst to form a 5-membered heterocyclic compound ("Plastic Age", 1
14, Mar. 1995), by reacting a dicarboxylic acid or a lower alkyl ester thereof corresponding to X in the above formula (I) with ethanolamine or a derivative thereof to form a 5-membered heterocyclic compound. be able to.

The ratio of the long-chain alkyl group-containing compound (1) to the bisoxazoline compound (2) depends on the type of the long-chain alkyl group-containing compound and its functional group, etc. The bisoxazoline compound (2) is used in an amount of 0.1 mol per mol of the functional group having an active hydrogen atom.
To 5 mol, preferably 0.5 to 3 mol, more preferably about 0.7 to 2 mol. Usually, an amount of an oxazoline group in excess of a functional group having an active hydrogen atom, for example, a long-chain alkyl group-containing compound (1)
Of the bisoxazoline compound (2) in an amount of 0.7 to 1.5 mol, preferably 0.8 to 1.3 mol, more preferably 0.9 to 1 mol, per 1 mol of the functional group having an active hydrogen atom.
It is about 2 mol.

Immediately after the preparation, the resin formulation for controlling insect pests of the present invention, based on 100 parts by weight of the resin, 1 to 50 parts by weight, preferably 2 to 25 parts by weight of the pest controlling component, and 0.1 parts by weight of the sustained release controlling agent 10 to 10 parts by weight, preferably 0.2 to 5 parts
Including parts by weight. When the amount of the sustained-release controlling agent is less than the above lower limit, the content of the pest controlling component may be reduced, and the controlled-release rate may not be able to be effectively controlled. On the other hand, when the amount of the sustained-release controlling agent exceeds the above upper limit, there may be a problem that the sustained-release controlling agent itself oozes out of the resin formulation and inhibits the expression of the efficacy of the pest controlling component.

The resin composition for controlling insect pests of the present invention is obtained by mixing a resin, a component for controlling insect pests, and a sustained-release controlling agent at an appropriate ratio.
It can be easily prepared by kneading and molding into a desired shape. The dosage form of the preparation is not particularly limited, and may be the same as that of a conventional sustained-release resin preparation.

[0046]

EXAMPLES Hereinafter, the present invention will be described specifically with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples. Example 1 Lauric acid (manufactured by Nacalai Tesque, Inc .; molecular weight 200.
3) 480 g and 2,2 ′-(1,3-phenylene) -bis (2-oxazoline) (“1,3” manufactured by Takeda Pharmaceutical Co., Ltd.)
-BPO "; 420 g of a molecular weight of 216.2) was reacted at 150 ° C. for 15 minutes, and the sustained-release control agent No. 1 was obtained. Polyethylene resin (VL80 manufactured by Sumitomo Chemical Co., Ltd.)
0) 100 parts by weight of the controlled release agent No. 1 to 1,
3 or 5 parts by weight and 8 parts by weight of phenothrin (Smithulin manufactured by Sumitomo Chemical Co., Ltd.) as an insecticide were melt-kneaded at 180 ° C. by an extrusion kneader and molded to obtain a resin preparation. The resulting resin preparation was cut into small pieces, and phenothrin was extracted with acetone and analyzed by gas chromatography. The content of phenothrin in the molded product was 4.4, 5.3, and 7.3 weight, respectively. %Met.

Comparative Example 1 Without using 1, the amount of phenothrin was 8
A resin preparation was obtained in the same manner as in Example 1 except that the amount was changed to parts by weight. The content of phenothrin in the molded product was 1.3% by weight. Table 1 summarizes the results of Example 1 and Comparative Example 1.

[0048]

[Table 1] Comparison between Comparative Example 1 and Example 1 shows that the addition of the sustained-release control agent can increase the drug content immediately after molding. Further, it can be seen that the initial drug content increases as the added amount of the sustained-release control agent increases.

Sustained Release Test The change over time in the amount of drug released from the resin preparations produced in Example 1 and Comparative Example 1 (the weight of drug released per unit surface area of the resin preparation per day) was quantitatively analyzed. The shape of the resin preparation used was a strand having a diameter of 1 mm. Table 2 shows the results.

[0050]

[Table 2]

The drug of Example 1 releases the drug better than the drug of Comparative Example 1, and it can be seen that the release of the drug is improved by the addition of the sustained release controlling agent.
It can be seen that as the added amount of the sustained-release controlling agent increases, the drug is released over a long period of time, and the sustained-release property is good.

Example 2 Lauric acid (manufactured by Nakarai Tesque Co., Ltd .; molecular weight: 200)
3) 960 g and 2,2 ′-(1,3-phenylene) -bis (2-oxazoline) (“1,3” manufactured by Takeda Pharmaceutical Co., Ltd.)
-BPO "; 420 g of a molecular weight of 216.2) was reacted at 150 ° C. for 15 minutes, and the sustained-release control agent No. 2 was obtained. In Example 2, the affinity between the sustained-release control agent and the drug was increased by using twice as much lauric acid as in Example 1 and increasing the ratio of the long-chain alkyl group (non-polar portion) in the sustained-release control agent. Decreased. 100 parts by weight of a polyethylene resin (VL800 manufactured by Sumitomo Chemical Co., Ltd.) was added to the above-mentioned sustained-release control agent No.
2 parts by weight and 8 parts by weight of phenothrin (Smithulin manufactured by Sumitomo Chemical Co., Ltd.) as an insecticide were melt-kneaded at 180 ° C. by an extrusion kneader and molded to obtain a resin formulation.

Example 3 Lauric acid (manufactured by Nacalai Tesque Co., Ltd .; molecular weight: 200)
3) 480 g and 2,2 ′-(1,3-phenylene) -bis (2-oxazoline) (“1,3” manufactured by Takeda Pharmaceutical Co., Ltd.)
-BPO "; 840 g of a molecular weight of 216.2) was reacted at 150 ° C. for 15 minutes. 3 was obtained. In Example 3, the ratio of the oxazoline group (polar moiety) in the sustained-release control agent was increased by using twice the oxazoline compound as compared with Example 1, and the affinity between the sustained-release control agent and the drug was improved. Was. 100 parts by weight of a polyethylene resin (VL800 manufactured by Sumitomo Chemical Co., Ltd.) was added to the above-mentioned sustained-release control agent No. 3 by weight, and 8 parts by weight of phenothrin (Smithulin manufactured by Sumitomo Chemical Co., Ltd.) as an insecticide,
The mixture was melt-kneaded at 180 ° C. by an extrusion kneader and molded to obtain a resin preparation.

Slow release test In the same manner as in Example 1, the change over time in the amount of drug release from the resin preparations produced in Examples 2 and 3 was quantitatively analyzed. Table 3 shows the results of Examples 2 and 3 together with the results of Example 1 and Comparative Example 1.

[0055]

[Table 3] It can be seen that in all of the examples, the drug was released better and the sustained release was better than in Comparative Example 1.

Drug Residual Rate The residual amount of the drug in the resin preparation used in the above-mentioned sustained release test was quantitatively analyzed by the method using the above-mentioned extraction and gas chromatography. Table 4 shows the results.

[0057]

[Table 4]

Controlled release agent No. In the case of 2, since the affinity for the drug was reduced by increasing the ratio of the long-chain alkyl group (non-polar portion) in the sustained-release control agent, the release of the drug was earlier than in Example 1. Is being done. On the other hand, the sustained release controlling agent No. In the case of No. 3, the release of the drug is delayed because the ratio of the oxazoline group (polar moiety) in the sustained-release control agent is increased to improve the affinity with the drug. in this way,
By changing the ratio between the oxazoline group and the long-chain alkyl group in the sustained-release control agent, the release rate of the drug can be arbitrarily controlled.

Claims (6)

[Claims] 1. A resin formulation for controlling insect pests, comprising a resin, a pest controlling component and a reaction product of a bisoxazoline compound and a compound having a long-chain alkyl group as a sustained-release controlling agent. 2. The pest control resin preparation according to claim 1, wherein the pest control component is at least one drug selected from the group consisting of insecticides, insect repellents, insect growth regulators and repellents. 3. The resin formulation for controlling insect pests according to claim 1, further comprising a synergist. 4. The pest control resin preparation according to claim 1, wherein the compound having a long-chain alkyl group is a carboxylic acid having 6 or more carbon atoms. 5. The bisoxazoline compound is represented by the following formula: (In the formula, D represents an alkylene group, a cycloalkylene group or an arylene group which may have a substituent,
R ¹ , R ² , R ³ and R ⁴ are the same or different and represent a hydrogen atom, an alkyl group or an aryl group which may have a substituent. 2. The resin formulation for controlling insect pests according to claim 1, which is a compound represented by the formula: 6. The resin according to claim 1, wherein the resin is an olefin resin.
2. The resin formulation for controlling insect pests according to 1.).