JPS5931702A - Repellent composition against noxious insect and acarid - Google Patents

Abstract

PURPOSE:A repellent composition against noxious insects and acarids, having extremely improved effects, capable of preventing almost securely the noxious insects and acarids from entering, containing a specific maleimide derivative such as N-(n-hexyl)-2-chloromaleimide. CONSTITUTION:A repellent composition against noxious insects and acarids containing a compound [e.g. N-(n-hexyl)-2-chloro-3-methylmaleimide, etc.] shown by the formula I [X and Y are H, halogen, alkyl, or X and Y are linked to form -S-alkylene-S- (with the proviso that X and Y are neither H nor halogen at the same time); R is H, alkyl, alkenyl, alkynyl, or cycloalkyl] as an active ingredient. The compound shown by the formula I , for example, is obtained by reacting a maleic anhydride derivative shown by the formula II with an amine shown by the formula RNH2. Preferably the repellent is blended with a proper carrier, or other compounding agents, processed into various kinds of forms suitable for application area, method, etc. and used.

Description

[Detailed description of the invention] The present invention relates to a new pest and mite repellent composition.

Conventionally, methods for exterminating various sanitary pests such as cockroaches include methods of spraying insecticides such as pyrethroid insecticides and methods of using various insect traps. These methods aim to kill pests by killing or trapping insects, and can prevent damage such as feeding damage and blood sucking caused by the pests to some extent, but they do not harm the inside of furniture such as kitchens, livestock sheds, water sheds, chests of drawers, etc., or the human body, It is not possible to avoid the flying, approaching, contact, invasion, and contamination of pests into animals and plants such as agricultural crops, and it is not possible to achieve a sufficient extermination effect.Moreover, the above methods require insecticidal or post-capture pest treatment. Therefore, it is particularly difficult to dispose of pests that die after entering furniture, etc., and this has the disadvantage of becoming a source of contamination. On the other hand, there is a known pest extermination method E that can prevent the above pests from flying or entering, and of course does not require any treatment to kill them, and uses a pest repellent. Various substances having the following properties are being researched, developed, and proposed.

However, none of the various substances proposed in Section F can exhibit a sufficiently satisfactory pest repellent effect, and only a few substances, including N,N-diethyl-meta-toluamide, have a satisfactory pest repellent effect. LM in the form of sprays, lotions, creams, etc. It is only used as a repellent for blood-sucking pests such as mosquitoes, fleas, bed bugs, and stable flies.

Furthermore, there are no known effective methods for controlling mites. Particularly in recent years, due to changes in the living environment, dust mites and other insects have become more likely to appear inside homes. C is on. Although these mites rarely show any direct harmful effects on the human body, they cause discomfort and cause allergic asthma, and there is a need for the development of a method for controlling mites.

In view of the above-mentioned current situation, the present inventors have conducted various studies with the aim of providing a repellent that exhibits excellent pest and mite repellent effects and can almost certainly prevent the invasion of pests and mites. As a result, it has been found that a specific compound represented by the following general formula (1) can exhibit pest and mite repellent effects that meet the above objectives.

The present invention was completed based on this new knowledge.

That is, the present invention is based on the general formula (wherein X and Y may be the same or different and represent a hydrogen atom, a halogen atom, or a lower alkyl group, or X and Y together represent an -S-alkylene-8- group) .

However, X and Y do not both represent a hydrogen atom or both represent a halogen atom. R represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or a cycloalkyl group) as an active ingredient.
-f pest and mite repellent compositions.

The pest and mite repellent composition of the present invention can exhibit extremely excellent pest and mite repellent effects because it contains the specific maleimide derivative represented by the above general formula (1) as an active ingredient. Its repellent effect not only protects against sanitary and blood-sucking pests and mites such as cockroaches, flies, insects, horseflies, fleas, and nano-beetles, but also against clothing pests such as burrs, carp moths, and grain storage pests such as weevils. fJiVc is also strong against ants, termites, slugs, etc.

The active ingredients of the repellent composition of the present invention include, in the above formula (1), x and y are hydrogen atoms; lower alkyl groups such as methyl and ethyl; halogen atoms such as chlorine and bromine; or -8 -CH, -C)I, -8- group, etc., where R is a hydrogen atom, carbon number/-/co such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, etc. Alkyl group, allyl group, butenyl group, butenyl group having a moderately straight or branched chain 4
= Compounds that are alkenyl groups such as lopargyl group and ethynyl group or cycloalkyl groups such as t2furkynyl group, cyclopentyl group and cyclohexyl group are used. Specifically, X is a methyl group, Y is a hydrogen atom, R is an alkyl group with a carbon number of /-/2 and a thyl group, Y is a chlorine atom, and B is a carbon number /-
A compound in which X is a hydrogen atom, Y is a chlorine atom, and R is an alkyl group with a carbon number of /-/; X and Y together form -8CH, CH, -8- R at t
is preferably an alkyl group having /-/2 carbon atoms. Particularly preferred are compounds in which KX is a hydrogen atom, Y is a methyl group, and R is an alkyl group, or compounds in which both X and Y are a methyl group and R is an alkyl group, in particular, R is an n-pentyl group, and H = a hexyl group. , n-heptyl group exhibits particularly excellent effects.

These compounds are, for example,
' It can be produced by reacting a maleic anhydride derivative represented by RNH2 with an amine represented by RNH2.

(X, Y, and R have the same meanings as in formula (1)) The repellent of the present invention can be applied as it is to areas where pest or mite repellency is required. Generally, it is preferable to use suitable carriers and other compounding agents to prepare various forms suitable for the application area, application method, etc., such as liquid or solid preparations. Examples of carriers used in preparing liquid preparations include water, alcohols such as methyl alcohol and ethyl alcohol, acetone,
Ketones such as methyl ethyl ketone, ethers such as tetrahydrofuran and dioxane, aliphatic hydrocarbons such as hexane, kerosene, paraffin, and petroleum benzine, aromatic hydrocarbons such as benzene and toluene, esters such as ethyl acetate, dichloroethane, etc. Examples include halogenated hydrocarbons. The repellent of the present invention in the form of a second liquid agent contains the usual film-forming agents on the thighs, 1- emulsifiers, dispersants, spreaders, wetting agents, stabilizers, in the form of spray creams, sprays, aerosols, etc. can be used. Examples of such additives include evannitrocellulose,
Cellulose derivatives such as acetyl cellulose, acetyl butyryl cellulose, and methyl cellulose, vinyl resins such as vinyl acetate resin, alkyd resins, urea resins,
Epoxy resins, polyester resins, urethane resins, silicone resins, acrylic resins, chlorinated rubber, coating film forming agents such as polyvinyl alcohol, soaps, polyoxyethylene fatty alcohol ethers such as polyoxyethylene oleyl ether, Surfactants such as polyoxyethylene alkylaryl ether of oxyethylene nonyl phenyl ether, polyoxyethylene fatty acid ester, fatty acid glyceride, sorbitan fatty acid ester, sulfuric acid ester of higher alcohol, alkylaryl sulfonate such as sodium dodecylbenzenesulfonate ,
Examples include propellants such as liquefied petroleum gas, dimethyl ether, and fluorocarbon, casein, gelatin, alginic acid, and CMC.

In addition, examples of carriers used for preparation in solid form include silicic acid, kaolin, activated carbon, bentonite,
Mineral powders such as diatomaceous earth, talc, clay, calcium carbonate, and ceramic powder can be used. Furthermore, in preparing the solid form, for example, tricyclodecane, cyclododecane, 2. d, one triisopropyl, 3. s-)
A sublimable solid agent may be obtained by melt-mixing or grinding the above active ingredient compounds using a sublimable carrier such as dioxane or trimethylenenorbornene, or a sublimable insect repellent such as paradichlorobenzene, naphthalene, or camphor. can.

In addition, the repellent of the present invention can be microencapsulated according to, for example, a spray drying method using polyvinyl alcohol or CMC, an in-liquid curing method using gelatin, polyvinyl alcohol, 7-ruky acid, etc., a coacervation method, etc. benzylidene
mVCH can also be prepared in the form of a gel using a gelling agent such as D-sorbitol or Karakeen.

Furthermore, the repellent of the present invention may contain known pest repellents, fertilizers, flavoring agents, coloring agents, and the like. Other pest repellents that can be blended include N,N-diethyl-meta-toluamide, 2.3. Da, S-bis(A, -7'tyrene)-
Tetrahydrofurfural, ')-n-propylisocincomeronate, di-n-butylsuccinate, co-hydroxyetheroctyl sulfide, etc., and N-(coetherhexyl)-bicyclo-[co, cot] as the potency enhancer. ] s-heptene, 3-dicarboximide, 4-(propylbimylonyl)-butelcarbityl ether, and antioxidants such as butylhydroxyanisole, dibutylhydroxytoluene, tocopherol, γ-oryzanol, etc. As an insecticide, the common name is allethrin and its geometric and (or) optical isomers, etc.
Naphtherthimeurea, cycloheximide, etc. are used as disinfectants, salicylic acid, p-chloro-m-xylenol, -
Examples of antifungal agents include α-bromosinnamic aldehyde and N-dimethyl-N-phenyl-N'-(fluorodichloromethyl)thiosulfamide.

The repellent of the present invention in various forms thus prepared can be used in areas infested by pests or mites where a repellent effect is required, such as crop cultivation fields, agricultural and horticultural greenhouses, orchards, livestock sheds, grain warehouses, etc., or homes. Indoor furniture such as kitchens, closets, entrances, washrooms or chests of drawers, costume cases, doll cases, and rugs such as rugs, tatami mats, etc. 11
- It can be applied by placing Yc on wood, etc., applying cloth, IQ mist, coating, pasting, etc.

The details of the active ingredient compound in the repellent of the present invention and the application of the repellent may be determined as appropriate depending on the formulation type, application method, application location, etc. (although not limited to, usually dispersants and When used in the form of a liquid such as a wettable powder, the active ingredient compound is l-
It is preferable to include θ% by weight or t% by weight of S-HiroO, and when it is made into a hard-cut form such as a powder /-! It is sufficient to contain 0 weight, preferably λ to 0 weight, and the active ingredient compound'f per 1 cup of coating use, per 1 coated area.
The QOI is preferably about aoi to θ3-my, and when used in a solid or other form, the application space/
Suitably, there is more than about /QQII of active ingredient compound per 71'l'.

Furthermore, the repellent composition of the present invention can be retained on a substrate and used as a repellent for pests and mites. The pest repellent material can be used as a sheet-like base material, a furniture member, etc., which has pest repellent properties by utilizing the characteristics of the base material.

Here, examples of the base material include synthetic resin sheets such as polyethylene, polypropylene, nylon, polyvinyl chloride, polyvinylidene chloride, and polyester, animal and plant material or inorganic fiber sheets (paper, cloth, nonwoven fabric, leather), secondary synthetic resins, etc. and inorganic fibers or powder, blended fabrics or nonwoven fabrics of the above synthetic resins and RJI #J vegetable fibers, foils or films of metals such as aluminum, stainless steel, and zinc, and laminated sheets of the above various sheets. I can give an example. (4) As the base material C, natural wood such as awn, pencil fern, oak, etc., and molded products of plastics such as vinyl chloride resin, chlorinated polyethylene, polyethylene, polypropylene, etc. can also be effectively used as furniture components. .

There are no particular limitations on the means for retaining the repellent composition of the present invention on the base material, for example, by coating, impregnating, dropping, blending, etc., so that the repellent composition of the present invention can be retained on the base material to achieve the desired purpose. It can be used by placing it on a spot or pasting it together.

There are no particular restrictions on retention 1, and it can be determined at your discretion, but
It is sufficient to retain approximately 172 times the amount of saturated impregnation of the base material.

In addition, by retaining the composition of the present invention in a carpet raw material, such as Vail Naga, Tank KJt, web, base fabric, etc., and then processing it into a carpet, a carpet with excellent pest and mite repellency can be obtained and can be used indoors. It is possible to prevent the occurrence of mites in the area.

Furthermore, such carpets and their materials have excellent insect repellent properties during storage. The amount of repellent retained is usually preferably about 5 to 20 θ per 1 square meter of pile yarn, fiber web, base fabric, and backing material. The backing material preferably contains θ5-is weight t% of the backing material, preferably 1 to S weight It can be effective.

17. There are particular restrictions on the means for retaining the tubeworm repellent substance on the carpet material. For example, coating, impregnation, dropping, crossing, etc. may be used. In this case, in the case of pile yarns and fiber webs, if the fibers are synthetic fibers, the repellent substance is mixed into the spinning dope during spinning, and if the fibers are natural fibers or porous fibers, the repellent substances are mixed during spinning and after the spinning process. may be impregnated with the attractant.

The backing material is not particularly limited, but may be emulsified by conventional means, for example, by stirring together the surfactants.

In the present invention, first. There are no particular restrictions on the material of the second base fabric, but polypropylene film is generally used.
Examples include Herashan cross. In addition, the materials of the fiber web and pile yarn include natural fibers, porous fibers,
Synthetic fibers and blends thereof are optional.

There are two types of pile yarns, woven pile yarn and long pile yarn, and any of them may be used. Furthermore, as the backing material, a wide range of conventional backing materials can be used, such as styrene-butadiene copolymer, urethane handle resin, vinyl chloride resin, and vinyl acetate. However, the present invention is not limited to the following embodiments as long as they do not go beyond the gist of the invention.

Example 1/ Rectangular container (bottom/6 x 1 crn, island size g cm)
Priatomy I was bred in the research room.
llllxpungana)/0θ head was released.

Prepare two pieces of untreated filter paper of the same size as two pieces of national university filter paper, and place chemically treated paper and untreated paper in the four corners of the container. The treated papers were arranged in an alternating manner (f, that is, the treated papers were placed diagonally).Next, absorbent cotton soaked in sugar water was placed on each piece of paper, and the ants on each piece of paper were placed over time. The multiplication factor was measured.The table below shows the results of experiments conducted with different drug doses.

In addition, the numerical values in the table below show the number of dots on the treated paper in the upper row and the number of dots on the untreated paper in the first row.

-]6- Table 1 The drugs used in Table 1 are as follows.

Human', N(n-hexyl)-Euchloroma/Imi1
“R:N (n-hexyl)-nichloro-3-meth
Lumaleimito C: N-(n-hexyl)-comethylmaleimito D: N-(n-hexyl)-,2,? -Dimethylmaleimide E: N-(n-hexyl)-, ? ,
A-Dithiatetrahydrophthalimide Example Compound A' in which each of the N-substituted alkyl groups of Compounds A, B, C, D and E used in Example 1 is an n-pentyl group.
, B', C', D', E' and [compounds A'', B'', C'', +3'', I'', which are n-heptyl groups, were conducted in the same manner as in Example 1. The corresponding A,
Similar results were obtained for B, C, D, and E.

Example 3 A test similar to Example 1 was conducted using the compounds shown in Table 1. The results are shown in Table 2.

Table 1 The compounds used in Table 1 are as follows.

FAN-71 thyl-2-chloromaleimide G; N-methyl-2-chloro-3-methylmaleimide H: N-methyl-comethylmaleimide lNN-methyl-3,6-cythiatetrahydrophthalimide 19 One example implementation Compounds F', G', E' and 1' used in Example 3, in which each N-substituent of compounds F, G, H1I is an ethyl group
Test 9 similar to Example 3 was conducted using Example 4, and approximately the same effect was obtained.

Example S Tyrophagu+s putraaa@ntla being reared for generations in the laboratory
a) Saturation double of approximately py-v petri dish (diameter toc
m), and on top of that, cardboard paper (6 x 6 m), black wood-free paper (6 x base cM), drug-impregnated paper (g x 3 rm)
), black high-quality paper (3X 3ffi) for this IIL
I put it at the beginning. After 2tI hours, the number of mites on the top and bottom of the treated paper was counted. The results are shown in Table 3.

90- Table 3 Compound A-I is the same as the compound used in Table 1 and Table 3.

Compounds A', B', C', E' and A used in Example λ
When similar experiments were conducted using ", B", C", and fw, the same effects as those of the corresponding A, B, C, D, and El were obtained.

Applicant: Earth Pharmaceutical Co., Ltd. Mitsubishi Chemical Industries, Ltd. Agent: Patent Attorney Hase - 7 others

Claims (1)

[Claims] (11 General formula (in the formula, X and Y may be the same or different and represent a hydrogen atom, a halogen atom, a lower alkyl group, or
and Y together represent an -8-alkylene-8- group. However, X and Y do not both represent a hydrogen atom or both represent a halogen atom. E represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or a cycloalkyl group. ) Pest and mite repellent composition containing the compound shown as an active ingredient