JPH024201B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a tick repellent. There are many types of mites, such as the citrus spider mite and the two-spotted spider mite, which parasitize plants and cause great damage to agricultural crops, while the house dust mite, the black-spotted mite, and the like parasitize animals and transmit infectious diseases. Although many proposals have been made as control agents for these mites, there is a desire to develop new mite control agents due to problems such as insufficient control effects or the development of drug resistance. On the other hand, due to changes in the living environment in recent years, dust mites, dust mites, etc. have been occurring inside homes, causing problems such as not only causing discomfort but also causing allergic asthma. It has been demanded. In view of the above-mentioned current situation, the present inventors have conducted various studies, and as a result, have discovered that a specific maleimide derivative represented by the following general formula () exhibits an excellent repellent effect against mites, and has achieved the present invention. That is, the gist of the present invention is that the general formula (In the formula, X and Y may be the same or different and represent a halogen atom. R represents a _C5 - _C6 alkyl group.) The present invention relates to a tick repellent containing a maleimide derivative represented by the following formula as an active ingredient. The tick repellent of the present invention exhibits an extremely excellent tick repellent effect by containing the specific maleimide derivative represented by the above general formula () as its active ingredient. The target mites are, for example,
Examples include spider mites such as citrus spider mite, apple spider mite, two-spotted spider mite, and false red spider mite; plant-parasitic mites such as red mite; animal-parasitic mites such as house dust mite and common dust mite; and furthermore, white mite and dust mite. As for the maleimide derivative which is the active ingredient of the tick repellent of the present invention, in the general formula (), X and Y are hydrogen atom, chlorine atom, bromine atom, fluorine atom, or iodine atom, and R has 5 to 8 carbon atoms. Examples include compounds that are alkyl groups having a straight chain or a branched chain. Specifically, N- (n-, i- or neo-)
Pentyl-2,3-dibromaleimide, N-
(n- or i-)hexyl-2,3-dibromaleimide, N-(1- or 2-)methylpentyl-2,3-dibromaleimide, N-heptyl-
2,3-dibromaleimide, N-octyl-
2,3-dibromaleimide, N-(2-ethylhexyl)-2,3-dibromaleimide, N-
(n-, i- or neo-)pentyl-2,3-difluoromaleimide, N-(n- or i-)hexyl-2,3-difluoromaleimide, N-(1
- or 2-) methylpentyl-2,3-difluoromaleimide, N-heptyl-2,3-difluoromaleimide, N-octyl-2,3-difluoromaleimide, N-(2-ethylhexyl)-2,
3-difluoromaleimide, N-(n-, i- or neo-)pentyl-2,3-diiodomaleimide, N-(n- or i-)hexyl-2,3-diiodomaleimide, N-(1 - or 2-) Methylpentyl-2,3-diiodomaleimide, N-heptyl-2,3-diiodomaleimide, N-octyl-2,3-diiodomaleimide, N-(2-
ethylhexyl)-2,3-diiodomaleimide,
N-(n-, i- or neo-)pentyl-2,3
-dichlormaleimide, N-(n- or i-)hexyl-2,3-dichlormaleimide, N-(1
- or 2-) methylpentyl-2,3-dichloromaleimide, N-heptyl-2,3-dichloromaleimide, N-octyl-2,3-dichloromaleimide, N-(2-ethylhexyl)-2, 3-dichloromaleimide, N-(n-, i- or neo-)
pentyl-2-chloro-3-iodomaleimide,
N-hexyl-2-chloro-3-iodomaleimide, N-(1 or 2-)methylpentyl-2-chloro-3-iodomaleimide, N-heptyl-2
-Chlor-3-iodomaleimide, N-octyl-2-chloro-3-iodomaleimide, N-(2
-ethylhexyl)-2-chloro-3-iodomaleimide, N-(n-, i- or neo-)pentyl-2-bromo-3-iodomaleimide, N-hexyl-2-bromo-3-iodomaleimide, N
-(1- or 2-)methylpentyl-2-bromo-3-iodomaleimide, N-heptyl-2-bromo-3-iodomaleimide, N-octyl-2
-Bromo-3-iodomaleimide, N-(2-ethylhexyl)-2-bromo-3-iodomaleimide, N-(n-, i- or neo-)pentyl-
2-iodo-3-fluoromaleimide, N-hexyl-2-iodo-3-fluoromaleimide, N
-(1- or 2-)methylpentyl-2-iodo-3-fluoromaleimide, N-heptyl-2-
Iodo-3-fluoromaleimide, N-octyl-2-iodo-3-fluoromaleimide, N-
(2-ethylhexyl)-2-iodo-3-fluoromaleimide, N-(n-, i- or neo-)pentyl-2-chloro-3-fluoromaleimide,
N-hexyl-2-chloro-3-fluoromaleimide, N-(1- or 2-)methylpentyl-2
-Chlor-3-fluoromaleimide, N-heptyl-2-chloro-3-fluoromaleimide, N-
Octyl-2-chloro-3-fluoromaleimide, N-(2-ethylhexyl)-2-chloro-3
-fluoromaleimide, N-(n-, i- or
neo-)pentyl-2-fluoro-3-bromaleimide, N-hexyl-2-fluoro-3-bromaleimide, N-(1- or 2-)methylpentyl-2-fluoro-3-bromaleimide,
N-heptyl-2-fluoro-3-bromaleimide, N-octyl-2-fluoro-3-bromaleimide, N-(2-ethylhexyl)-2-fluoro-3-bromaleimide, N-(n-,i
- or neo-) pentyl-2-bromo-3-chloromaleimide, N-hexyl-2-bromo-3-
Chlormaleimide, N-(1- or 2-)methylpentyl-2-bromo-3-chlormaleimide,
Examples include N-heptyl-2-bromo-3-chloromaleimide, N-octyl-2-bromo-3-chloromaleimide, and N-(2-ethylhexyl)-2-bromo-3-chloromaleimide. In particular,
Preferred is a compound in which both X and Y are a chlorine atom or a bromine atom. These compounds are e.g.

It can be produced by reacting maleic anhydride represented by the formula with amines represented by RNH ₂ . Although the above-mentioned active ingredient compound of the tick repellent of the present invention can be applied as it is to areas where tick repellency is required, it is usually preferable to use a suitable carrier or other compounding agent to adjust the application area, application method, etc. It is prepared and used in various suitable forms, such as liquids and solids. Examples of carriers used in preparing liquid preparations include water, alcohols such as methyl alcohol and ethyl alcohol, ketones such as acetone and methyl ethyl ketone, ethers such as tetrahydrofuran and dioxane, hexane, kerosene, paraffin, Examples include aliphatic hydrocarbons such as petroleum benzene, aromatic hydrocarbons such as benzene and toluene, esters such as ethyl acetate, and halogenated hydrocarbons such as dichloroethane. The mite repellent of the present invention in the form of a liquid may further contain additives such as a film forming agent, an emulsifier, a dispersing agent, a spreading agent, a wetting agent, a stabilizer, a propellant, etc. form, adhesive form, emulsion, dispersant,
It can be used in the form of suspensions, lotions, creams, sprays, aerosols, and the like. Examples of such additives include nitrocellulose, acetylcellulose, acetylbutyrylcellulose,
Cellulose derivatives such as methylcellulose, vinyl resins such as vinyl acetate resin, alkyd resins,
Film forming agents such as urea resin, epoxy resin, polyester resin, urethane resin, silicone resin, acrylic resin, chlorinated rubber, and polyvinyl alcohol, soaps, and polyoxyethylene fats such as polyoxyethylene oleyl ether Alcohol ether, polyoxyethylene alkyl allyl ether such as polyoxyethylene nonyl phenyl ether, polyoxyethylene fatty acid ester, fatty acid glyceride, sorpitan fatty acid ester, higher alcohol sulfate ester, alkyl allyl sulfonate such as sodium dodecylbenzenesulfonate surfactants such as, liquefied petroleum gas, dimethyl ether, propellants such as fluorocarbons,
Examples include casein, gelatin, alginic acid, and CMC. In addition, examples of carriers used for preparation in solid form include silicic acid, kaolin, activated carbon,
Examples include mineral powders such as bentonite, diatomaceous earth, talc, clay, calcium carbonate, and ceramic powder, vegetable powders such as wood flour, soybean flour, wheat flour, and starch, and clathrate compounds such as cyclodextrin. Furthermore, when preparing the solid agent form, for example, tricyclodecane, cyclododecane, 2,4,6-
triisopropyl-1,3,5-trioxane,
A sublimable solid agent can also be obtained by melt-mixing or crushing the above-mentioned active ingredient compounds and molding them using a sublimable carrier such as trimethylene norbornene or a sublimable insect repellent such as paradichlorobenzene, naphthalene, or camphor. The above-mentioned solid agent also includes the form of a resin molded product in which the active ingredient compound is kneaded into plastic. In addition, the tick repellent of the present invention can be applied, for example, by spray drying using polyvinyl alcohol, CMC, etc.
Prepared in microencapsulated form using gelatin, polyvinyl alcohol, alginate sugar, in-liquid curing method, coacervation method, etc.
It can also be prepared in the form of a gel using a gelling agent such as benzylidene-D-sorbitol or carrageenan. Furthermore, the mite repellent of the present invention includes known pest repellents, efficacy enhancers, antioxidants, insecticides, acaricides, rodent control and repellents, fungicides, fungicides, and herbicides. Agents, fertilizers, flavoring agents, coloring agents, etc. can be added. Other pest repellents that can be blended include N,N-diethyl-meta-toluamide, 2,3,4,5-bis( _A2 -butylene)-tetrahydrofurfural, di-n-propylisocincomeronate, di-n-butyl succinate, 2-hydroxyethyl octylsulfide, etc., and N-(2-ethylhexyl)-bicyclo-[2,2,1]-5-heptene-2,3-di Carboximide, 6-(propylpiperonyl)-butyl carbityl ether, etc.
Antioxidants include butylated hydroxyanisole, dibutylated hydroxytoluene, tocopherol, γ-oryzanol, etc. As insecticides, pyrethroids such as the common name allethrin and its geometric and/or optical isomers are used for rodent control and α-naphthylthiourea, cycloheximide, etc. are used as repellents, and salicylic acid, p-
Chloro-m-xylenol, 2-(4'-thiazoyl)benzimidazole, etc. are used as antifungal agents.
Examples include -bromocinnamic aldehyde, N-dimethyl-N-phenyl-N'-(fluorodichloromethyl)thiosulfamide, and the like. The mite repellent of the present invention in various forms thus prepared can be used in areas infested with mites where a repellent effect is required, such as agricultural fields, orchards, general households, grain warehouses, cafeteria kitchens, furniture,
It can be applied by placing, scattering, spraying, coating, pasting, etc. on a carpet, folding room, closet, entrance, washroom, etc., or by scattering, spraying, coating, etc. on animals and plants themselves. Furthermore, the tick repellent of the present invention can be applied to a suitable sheet-like base material in advance by applying it, impregnating it, dropping it, kneading it, etc., and then placing it on the desired location in the form that it is retained on the base material. It can also be used by pasting them together. Examples of sheet-like substrates used in this case include synthetic resin sheets such as polyethylene, polypropylene, nylon, polyvinyl chloride, polyvinylidene chloride, and polyester, animal and vegetable or inorganic fiber sheets (paper, cloth, nonwoven fabric, leather, etc.) , mixed sheets or blended fabrics of synthetic resins and inorganic fibers or powders, blended fabrics or nonwoven fabrics of the above synthetic resins and animal and plant fibers, aluminum,
Examples include metal foils or films such as stainless steel and zinc, and laminated sheets of the above various sheets. Furthermore, the mite repellent of the present invention can be used as a furniture member such as natural wood such as awn, pencil fern, oak, etc., plastics such as vinyl chloride resin, chlorinated polyethylene, polyethylene, polypropylene, etc., tatami mats, carpets, etc. pre-coated, impregnated, dripped,
It is also possible to use it by retaining it by kneading or the like. The amount of the active ingredient compound in the tick repellent of the present invention and the amount of the repellent to be applied may be appropriately determined depending on the dosage form, application method, application location, etc., and are not limited to the above. When used in the form of a liquid such as a wettable powder, the active ingredient compound may be contained in an amount of 1 to 80% by weight, preferably 5 to 40% by weight, and when used in the form of a solid such as a powder, it may be contained in an amount of 1 to 50% by weight. , preferably 2 to 20% by weight, and when it is held in a sheet-like base material or furniture member,
It is sufficient to maintain approximately 1/2 of the saturated impregnation amount of the base material, etc. In addition, as for the application amount of the pest repellent of the present invention, for example, in the case of application, the area to be applied is 1 cm ²
It is recommended that the active ingredient compound be present in an amount of about 0.001 mg or more, preferably about 0.01 to 0.5 mg per product, and when used in solid form or other forms, it is appropriate that the active ingredient compound be present in an amount of about 100 mg or more per 1 m ² of application space. It is. Examples will be given below to explain the present invention in more detail. In addition, the compounds shown in Table 1 were used in the experiment. The test compound numbers in each example correspond to the compound numbers in Table 1.

【table】

[Table] Example 1 (Test for repellent effect on woolly mites) A saturated medium for mites was prepared as shown in FIG. 1, and a cardboard box was placed on the medium. Place a piece of black high-quality paper (6 x 6cm) on top of it and leave it for a while. After confirming that the mites have migrated to the black paper, place another piece of black high-quality paper (6 cm x 6 cm) on top of the black paper that has been uniformly treated with a predetermined amount of the test compound. 5 x 5 cm) was placed gently on top of it, and then untreated black high-quality paper (4 x 4 cm) was placed on top of it. Observation is
After 48 hours, the repellent effect is determined by recording the number of mites attached to the upper and lower untreated papers. The results are shown in Table 2.

[Table] As is clear from the experimental effects in Table 2 above, an excellent repellent effect against the woolly mites was observed, and it was confirmed that sample Nos. 6, 7, 8, and 9 showed particularly excellent activity. .

[Brief explanation of drawings]

FIG. 1 shows a schematic diagram of a saturated medium for woolly mites used in Example 1. In the figure, 1 is saturated medium, 2 is untreated black wood-free paper (6 x 6 cm), and 3 is treated black wood-free paper (5 x 5 cm).
cm), 4 is untreated black high-quality paper (4 x 4 cm), and 5 is cardboard.

Claims (1)

[Claims] 1. General formula (In the formula, X and Y may be the same or different and represent a halogen atom. R represents an alkyl group having 5 to 8 carbon atoms.) A tick repellent containing a maleimide derivative represented by the following as an active ingredient.