JP2001328915A - Composition for aerosol for controlling pest - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a readily usable composition for an aerosol for controlling a pest, having high pest-controlling activities. SOLUTION: This composition for the aerosol for controlling the pest contains 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 3-(2-methyl-1-propenyl)-2,2- dimethylcyclopropanecarboxylate, and a propellant.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a composition for controlling aerosols.

[0002]

2. Description of the Related Art Various pest control aerosol formulations for controlling pests such as mosquitoes are known, but they are more effective in controlling pests and can be used easily. The development of aerosol preparations for medical use is always desired.

[0003]

Means for Solving the Problems The present inventors have made intensive studies in such a situation and found that 4-methoxymethyl-
2,3,5,6-tetrafluorobenzyl 3- (2-
It has been found that a composition for a pest control aerosol containing (methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylate and a propellant can exert an excellent control effect on pests, which has led to the present invention. . That is, the present invention relates to 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 3- (2-methyl-1-propenyl).
Provided is a composition for a pest control aerosol (hereinafter, referred to as a composition of the present invention), comprising -2,2-dimethylcyclopropanecarboxylate (hereinafter, referred to as the present compound) and a propellant.

[0004]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail. This compound can be produced, for example, by the following method. Equation (1) A carboxylic acid compound or an acid halide thereof represented by the formula (2): A method of producing by reacting with an alcohol compound represented by the formula:

The reaction is usually carried out in an organic solvent, if necessary, in the presence of a reaction aid. The range of the reaction time is usually about 5 minutes to 72 hours, and the reaction temperature is usually −
80 ° C. to 200 ° C., but the boiling point of the organic solvent is 200 ° C.
If it is less than the boiling point, the freezing point of the organic solvent is -80.
When the temperature is higher than ° C, the temperature is higher than the freezing point. Equation (1)
The molar ratio of the carboxylic acid compound represented by the formula (1) or the acid halide thereof to the alcohol compound represented by the formula (2) can be determined as appropriate, but is preferably performed at a ratio of 1: 1 or close thereto.

When a carboxylic acid compound represented by the formula (1) is used as a reaction assistant, for example, dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, diethylazodicarboxylate And a reagent of diisopropylazodicarboxylate and triphenylphosphine. When an acid halide of a carboxylic acid compound represented by the formula (1) is used, for example, triethylamine, 4-dimethylaminopyridine, diisopropyl Tertiary amines such as ethylamine can be exemplified.

Examples of the solvent include hydrocarbons such as toluene and hexane, ethers such as diethyl ether and tetrahydrofuran, and halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane. Or mixed and used. The progress and completion of the reaction can be checked by analyzing the reaction solution by gas chromatography, liquid chromatography, etc., and after the reaction is completed, the reaction solution should be subjected to ordinary post-treatment operations such as washing, extraction, concentration, etc. To obtain the present compound. If necessary, it can be purified by column chromatography, distillation or the like. The alcohol compound represented by the formula (2) is disclosed in
It can be produced according to the method described in JP-A-6694.

The present compound has stereoisomers such as an optical isomer based on an asymmetric carbon and a geometric isomer based on a cyclopropane ring. The present compound includes all optical isomers having a pest control activity and mixtures thereof, and all geometric isomers having a pest control activity and mixtures thereof. The content of the present compound in the composition of the present invention is usually about 0.001 to 20% by weight.

The propellant used in the composition of the present invention has a boiling point of 25 which can be uniformly mixed with the liquid portion in the composition of the present invention.
C. or lower, for example, dimethyl ether (boiling point -2
4.8 ° C.), propane (boiling point −42.1 ° C.), n-butane (boiling point −0.5 ° C.), isobutane (boiling point −12 ° C.), and the like, alone or in combination of two or more. Can be used in mixtures. The amount of propellant in the composition of the present invention is usually 20 to 99.9999% by weight.

[0010] The composition of the present invention may contain a solvent.
A solvent having a boiling point of 30 to 120 ° C. is more preferable, and a solvent having a boiling point of 30 to 100 ° C. is still more preferable. Practically, the solvent has a boiling point of substantially 30 to 21.
Compositions of the present invention that contain only a 0 ° C. solvent are preferred. Here, the solvent having a boiling point of 30 to 210 ° C means that the boiling points of all components constituting the solvent are substantially in the range of 30 to 210 ° C, and specifically, in the case of a single solvent, The boiling point of the solvent, and in the case of two or more kinds of mixed solvents, means that the boiling point of 95% by weight or more of the components of the mixed solvent is in the range of 30 to 210 ° C. The same applies to a solvent having a boiling point of 30 to 120 ° C and a solvent having a boiling point of 30 to 100 ° C. Unless otherwise specified, the boiling point of the solvent means the boiling point at atmospheric pressure.

The solvent is preferably a solvent capable of keeping the entire composition of the present invention uniform. Here, the term “the entire composition is uniform” means that it is in a so-called solution state, which does not substantially show a state of being separated between an aqueous layer and an oil layer, a state where crystals are precipitated, an emulsion state, a suspension state, and the like. Means

Examples of the solvent include n-butyl alcohol (boiling point: 117.9 ° C.), sec.-butyl alcohol (boiling point: 99.5 ° C.), tert.-butyl alcohol (boiling point: 82.3 ° C.), n-butyl alcohol Propyl alcohol (boiling point 9
7.2 ° C.), isopropyl alcohol (boiling point 82.4)
° C), ethyl alcohol (boiling point 78.3 ° C), hexane (boiling point 69 ° C), heptane (boiling point 98.4 ° C), 2-methylpentane (boiling point 60 ° C), 2,2-dimethylbutane (boiling point 50 ° C) Octane (boiling point 125 ° C.), nonane (boiling point 149.5 ° C.), decane (boiling point 174 ° C.), undecane (boiling point 195.9 ° C.), IP1620 (trade name, manufactured by Idemitsu Petrochemical Co., Ltd., isoparaffin solvent, boiling point 1)
66-202 ° C), IP1016 (trade name, manufactured by Idemitsu Petrochemical Co., Ltd., isoparaffinic solvent, boiling point 73-140)
° C). In addition, water (boiling point 100
° C), but from the viewpoint of keeping the entire composition of the present invention uniform as described above, when water is used, it is compatible with water, and also compatible with the present compound and the propellant. It is preferably used as a mixed solvent having an alcohol such as isopropanol.

When a solvent is used, the amount of the solvent in the composition of the present invention is not more than 79.9999% by weight, preferably 5% by weight.
６０60% by weight.

The composition of the present invention can appropriately contain other pest-controlling compounds, repellents, synergists, stabilizers, etc., which can be expected to further improve the efficacy. Other insecticidally active compounds include, for example, arethrin, tetramethrin, praethrin, phenothrin, resmethrin, cyphenothrin, permethrin, cypermethrin, deltamethrin, tralomethrin, cyfluthrin, framethrin, imiprotrin, etofenprox, fenvalerate, fenpropathrin, silaflufen , Transfluthrin, bifenthrin, empentrin, 2-methyl-4-oxo-3- (2-propynyl) -cyclopent-2-enyl 3- (2,2-
Pyrethroid compounds such as dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate; organic phosphorus compounds such as dichlorvos, fenitrothion, tetrachlorovinphos, fenthion, chlorpyrifos, diazinon; carbamate compounds such as propoxer, carbaryl, methoxadiazon, fenobcarb, Lufenuron,
Chlorfluazuron, hexaflumuron, diflubenzuron, cyromazine, 1- (2,6-difluorobenzoyl) -3- [2-fluoro-4- (1,1,2,3,3
Chitin formation inhibitors such as [3,3-hexafluoropropoxy) phenyl] urea, juvenile hormone-like substances such as pyriproxyfen, methoprene, hydroprene and phenoxycarb, neonicotinoid compounds, N-phenylpyrazole compounds and the like Can be mentioned.

Examples of repellents include N, N-diethyl-m-toluamide, limonene, linalool, citronellal, menthol, menthone, hinokitiol, geraniol, eucalyptol, indoxacarb, carane-3,4-diol, MGK-R-326, MGK-
R-874, BAY-KBR-3023 and the like can be mentioned. As the synergist, for example, PBO, MGK2
64, S421, IBTA, Sinepirin 500 and the like.

As the stabilizer, for example, 2,6-di-t
And phenolic antioxidants such as -butyl-4-methylphenol.

The aerosol preparation comprising the composition of the present invention can be obtained, for example, as follows. The compound,
If necessary, the aerosol container is filled with a solvent, other active compounds for controlling pests, repellents, synergists, stabilizers and the like. This is achieved by mounting an aerosol valve on the container, filling the container with a propellant through a stem, shaking, and then mounting an actuator. As the actuator, for example, a button type, a trigger type, or the like can be used. When the aerosol preparation is a so-called full injection aerosol preparation in which all contents in the container are discharged by one injection, a full injection actuator is used instead of the actuator. You. The full-injection-type actuator has a mechanism in which once pressed, the pressed state is maintained.

The aerosol formulation comprising the composition of the present invention
It is usually applied by spraying the insect body or habitat of the pest. The aerosol formulation of the present invention, which can be sprayed at 0.001 to 100 mg / sec, of the present compound contained in the composition of the present invention, depends on the type of pest to be controlled and the size of the place to be used, etc. At 0.1 seconds to 1
It is desirable to spray for about 00 seconds. In addition, in the case of a full injection aerosol preparation, it is usually desirable to apply the preparation indoors.

Examples of pests that can be controlled by the composition of the present invention include the following. Housefly (Musca domestica) and housefly (Mus
flies such as cina stabulans, and Culex pipiens (Culex pipi)
ens pallens), Culex tritaeniorh (Culex tritaeniorh)
ynchus), Aedes Culex (Culex quinquefasciatu)
s), mosquitoes such as Aedes albopictus,
German cockroach (Blattella germanica), black cockroach (Periplaneta fuliginosa), brown cockroach (Pe
cockroaches such as riplaneta americana, Tyrophagus putrescentiae, Dermatophagoides farinae (D
ermatophagoides farinae), stag beetle (Cheylet
us malaccensis), southern mites (Cheyletus moorei)
Indoor mites, such as white lice (Pediculus humanus co)
rporis).

As wood pests, Japanese termites (Reti
culitermes speratus, termite (Coptotermes f)
ormosanus) and bark beetles. Examples of unpleasant pests include midges, fly flies, ants, bees, fleas and the like.

As animal pests, cat flea (Ctenocepha
lides felis), dog flea (Ctenocephalides canis), human flea (Pulex irritans), keops flea (Xeno
fleas such as psylla cheopis, Haemaphysalis longicornis (Haem)
aphysalis longicornis), Ixodes ovatu
s), ticks such as ox tick (Boophilus microplus), and lice such as bovine lice (Haematopinus eurysternus). Agricultural pests include peach aphids (Myzu
s persicae), aphids and blue stink bugs (Ne
stink bugs such as zara antennata) and brown planthopper (La
odelphax striatellus) and whiteflies such as silver leaf whitefly (Bemisia argentifolii).

[0022]

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto. Production Example 1 A mixed solution of 1.0 g of 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl alcohol, 0.42 g of pyridine and 10 ml of tetrahydrofuran was added to a mixed solution under ice-cooling.
-(2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylic acid chloride {ratio of stereoisomers (1R) -trans form: (1R) -cis form: (1S)-
Trans form: (1S) -cis form = 93.9: 2.5:
3.5: After adding 0.1０0.90 g, the mixture was heated to room temperature and stirred at the same temperature for 8 hours. The reaction solution was added to ice water
and extracted twice with 80 ml of ethyl acetate.
The ethyl acetate layers were combined, washed with saturated saline, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography to give 4-methoxymethyl-2,3,5, 1.40 g (yield 84%) of 6-tetrafluorobenzyl 3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylate (hereinafter referred to as compound A) was obtained. ¹ H-NMR (CDCl ₃ , TMS internal standard) δ value (pp
m): 1.13 (s, 3H), 1.26 (s, 3H), 1.3
8 (d, 1H), 1.69 (brs, 6H), 2.10
(Dd, 1H), 3.40 (s, 3H), 4.59
(S, 2H), 4.87 (d, 1H), 5.24 (d
d, 2H)

Formulation Example 1 0.025 g of compound A is put in an aerosol can, and after attaching an aerosol valve to the aerosol can, 99.975 g is prepared.
Of dimethyl ether, shaking was added, and an actuator was attached to obtain an aerosol preparation 1.

Formulation Example 2 An aerosol formulation 2 was obtained in the same manner as in Formulation Example 1, except that the amount of Compound A was 0.05 g and the amount of dimethyl ether was 99.95 g.

Formulation Example 3 An aerosol formulation 3 was obtained in the same manner as in Formulation Example 1, except that the amount of Compound A was 0.1 g and the amount of dimethyl ether was 99.9 g.

Formulation Example 4 An aerosol formulation 4 was obtained by performing the same operation as in Formulation Example 1 except that the amount of Compound A was changed to 0.2 g and the amount of dimethyl ether was changed to 99.8 g.

Formulation Example 5 An aerosol formulation 5 is obtained by performing the same operation as in Formulation Example 1 except that the amount of compound A is 0.5 g and the amount of dimethyl ether is 99.5 g.

Formulation Example 6 The amount of compound A was 1 g, and the amount of dimethyl ether was 99 g.
An aerosol preparation 6 is obtained by performing the same operation as in Preparation Example 1 except that the amount is changed to g.

Formulation Example 7 The amount of compound A was 5 g, and the amount of dimethyl ether was 95
An aerosol preparation 7 is obtained by performing the same operation as in Preparation Example 1 except that the amount is changed to g.

Formulation Example 8 0.025 g of compound A and 49.975 g of a mixed solvent of water / isopropanol (1/1 (wt / wt)) were put in an aerosol can, and an aerosol valve was attached. Then, 50 g of dimethyl ether was charged and shaken. Addition of a cap, and mounting of an actuator gave an aerosol formulation 8.

Formulation Example 9 The amount of compound A is 0.05 g, and the amount of water / isopropanol mixed solvent (1/1 (wt / wt)) is 49.95 g.
Aerosol preparation 9 was obtained by performing the same operation as in Preparation example 8 except that the above was used.

Formulation Example 10 The same operation as in Formulation Example 8 is carried out except that the amount of compound A is 0.1 g and the amount of water / isopropanol mixed solvent (1/1 (wt / wt)) is 49.9 g. Thereby, the aerosol preparation 10 was obtained.

Formulation Example 11 The same operation as in Formulation Example 8 is carried out except that the amount of compound A is 0.2 g and the amount of the water / isopropanol mixed solvent (1/1 (wt / wt)) is 49.8 g. Thereby, the aerosol preparation 11 was obtained.

Formulation Examples 12-15 Water / isopropanol mixed solvent (1/1 (wt / w)
t)) instead of IP1620 (trade name, manufactured by Idemitsu Petrochemical Co., Ltd., isoparaffinic solvent, boiling point 166 to 202)
C)) to obtain Aerosol preparations 12 to 15 by performing the same operation as in Preparation examples 8 to 11.

Formulation Example 16 The amount of compound A was 0.5 g, and IP1620 (trade name, manufactured by Idemitsu Petrochemical Co., Ltd., isoparaffin-based) was used instead of 49.975 g of a mixed solvent of water / isopropanol (1/1 (wt / wt)). Solvent, boiling point 166-202 ° C) 49.5 g
An aerosol formulation 16 is obtained by performing the same operation as in Formulation Example 8 except that

Formulation Example 17 The amount of Compound A was 1 g, and IP1620 (trade name, manufactured by Idemitsu Petrochemical Co., Ltd., isoparaffinic solvent, boiling point 166)
Aerosol formulation 17 is obtained by performing the same operation as in Formulation Example 16 except that the amount is set to 49 g.

Formulation Example 18 The amount of Compound A was adjusted to 5 g, and IP1620 (trade name, manufactured by Idemitsu Petrochemical Co., Ltd., isoparaffinic solvent, boiling point 166)
The aerosol preparation 18 is obtained by performing the same operation as in Preparation Example 16 except that the amount of the mixture is adjusted to 45 g.

Formulation Examples 19 to 25 IP 1620 (trade name, manufactured by Idemitsu Petrochemical Co., Ltd., isoparaffinic solvent, boiling point: 166 to 202 ° C.)
Aerosol preparations 19 to 25 are obtained by performing the same operations as in Preparation examples 12 to 18 except that 1016 (trade name, manufactured by Idemitsu Petrochemical Co., Ltd., isoparaffin-based solvent, boiling point: 73 to 140 ° C.) is used.

Formulation Examples 26 to 32 The same operations as in Formulation Examples 12 to 18 are performed except that ethyl alcohol is used instead of IP1620 (trade name, manufactured by Idemitsu Petrochemical Co., Ltd., isoparaffinic solvent, boiling point: 166 to 202 ° C.). To obtain aerosol preparations 26 to 32.

Formulation Examples 33 to 39 By performing the same operations as in Formulation Examples 12 to 18 except that hexane is used instead of IP1620 (trade name, manufactured by Idemitsu Petrochemical Co., Ltd., isoparaffin solvent, boiling point: 166 to 202 ° C.). Aerosol preparations 33-39 are obtained.

Formulation Examples 40 to 78 Aerosol formulations 39 to 78 are obtained by performing the same operations as in Formulation Examples 1 to 39 except that a total release actuator is used instead of the actuator.

Formulation Examples 79 to 92 Aerosol formulations 79 to 92 are obtained by performing the same operations as in Formulation Examples 12 to 25 except that LPG is used instead of dimethyl ether.

Test Example 1 (mosquito efficacy test) Approximately 50 adult female Culex pipiens pallens were released into a cubic test chamber (5.8 m ³ ) of 1.8 m on a side, on which imitation paper was laid on the floor. The aerosol preparation 3 was sprayed once from the small windows provided on each of the four side surfaces of the chamber so that the total spray amount was about 0.65 g, a total of four times. After spraying, 2, 3, 5, 7, 10 and 15 minutes later, the number of Culex pipiens knocked down was counted, and KT50 (the time required for 50% of the test insects to be knocked down) was determined from the obtained data. Was. Further, the same test was performed on the aerosol preparation 10. Table 1 shows the results.

[0044]

[Table 1]

[0045]

According to the present invention, a pest control aerosol composition having a high pest control effect can be provided.

Continued on the front page F term (reference) 4H006 AA01 AA03 AB02 BJ50 BM30 BN10 BP10 4H011 AC01 AC02 AC03 BA01 BB15 BC03 DA21 DE15

Claims (5)

[Claims] 1. A pest control comprising 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylate and a propellant. Aerosol compositions. 2. The pest controlling aerosol composition according to claim 1, further comprising a solvent having a boiling point of 30 to 210 ° C. 3. The pest controlling aerosol composition according to claim 2, wherein the solvent has a boiling point of 30 to 120 ° C. 4. The pest controlling aerosol composition according to claim 2, wherein the solvent has a boiling point of 30 to 100 ° C. 5. The composition for controlling insect pests according to claim 4, wherein the solvent contains an alcohol.