KR100907196B1 - Pesticidal methods and uses - Google Patents

Abstract

The present invention relates to pesticidal methods and uses. The method includes applying a tetrafluorobenzyl ester compound represented by Formula 1 to the surface of a building structure or household article:

[Wherein, R represents a methyl group or a methoxymethyl group].

Description

Insecticide Methods and Uses {PESTICIDAL METHODS AND USES}

It is well known that delayed insecticidal suppression against non-existing pests in an indoor environment can be provided by directly applying the pesticidal active compound to the emergency pest or by dispersing the pest-active compound in an indoor environment with electric appliances. When applying pest active compounds directly to non-communicating pests, it is often necessary to use pesticidal active compounds, wherein the pesticidal active compounds are applied repeatedly for all cases where non-communicating pests enter the indoor environment. When dispersing pest active ingredients, continuous operation of the electrical device is usually required.

USP 6,225,495 describes tetrafluorobenzyl ester compounds represented by the formula:

The present invention provides a method of inhibiting pests in an indoor environment and the use of a tetrafluorobenzyl ester compound represented by Formula 1:                         

[Formula 1]

[Wherein, R represents a methyl group or a methoxymethyl group].

The method includes applying a tetrafluorobenzyl ester compound represented by Formula 1 to the surface of a building structure or household article.

The method of the present invention relates to a tetrafluorobenzyl ester compound represented by the formula (1). Tetrafluorobenzyl ester compounds can be prepared according to the methods described in USP 6,225,495. Tetrafluorobenzyl ester compounds include various pesticidal isomeric forms thereof such as optical isomers or geometric isomers. Examples of such isomers of the tetrafluorobenzyl ester compounds include optical isomers based on two asymmetric carbon atoms present in the cyclopropane ring segment (R, S), C = C double bonds inside (E, Z). Geometric isomers and the like. Moreover, tetrafluorobenzyl ester compounds may include isomers that are optical isomers and geometric isomers.

In the method of the present invention, a tetrafluorobenzyl ester compound represented by the formula (1) is applied to the surface of a building structure or household article. Application typically penetrates the tetrafluorobenzyl ester compound onto the surface of a building structure or household article. After infiltration, the applied tetrafluorobenzyl ester compound is automatically evaporated at room temperature so that the evaporated pesticidal compound can inhibit non-existent pests. In the application of a tetrafluorobenzyl ester compound, either a tetrafluorobenzyl ester compound or a mixture of tetrafluorobenzyl ester compounds or an isomeric mixture of tetrafluorobenzyl ester compounds can be applied.

The building structure may typically be a fixture of a building that constitutes an interior compartment of the building. Examples of building structures include ceilings, interior walls, columns, ranma (openwork screens on sliding partitions between two rooms), windows, cabinets, floors, doors, and the like. Examples of buildings include homes, offices, apartment buildings, and the like. When the tetrafluorobenzyl ester compound is applied to the surface of a building structure, the tetrafluorobenzyl ester compound is protected against paints present in the building structure, wallpaper on the interior walls, plaster on the ceiling, floors, floor tiles, etc. It can be applied to the carpet.

The household items may be movable furniture products that are typically placed in building rooms for extended periods of time, such as one month or longer. The household items can typically be moved into or out of the building's room. Household items can be made of fabric, wood, plastic, or metal. Examples of household items include curtains, furniture (drawers, storage shelves, fluorescent lights, desks, chairs, kakemono (hangers hanging or hanging pictures), noren (store curtains), blinds, piano, vases, rugs, etc.) When applied to the surface of a household article, pesticide compounds may be applied to the paints present in the household article, to the care of wooden upholstery, and the like.

When the tetrafluorobenzyl ester compound is applied to the surface of a building structure or household article, the tetrafluorobenzyl ester compound may be used in several formulation forms, such as aerosol formulations, oily formulations, water based liquid formulations, mist formulations, It can be used as a heating device formulation, a blower formulation, or the like. When using an aerosol formulation, the aerosol formulation can be sprayed directly or indirectly onto the surface of the building structure or household article. When using an oily or water based liquid formulation, the oily or water based liquid formulation can be diffused directly onto the surface of the building structure or household article, for example by coating with a brush or a comb. When using mist formulations or full release aerosol formulations, the mist formulations or total release aerosol formulations may be indirectly applied to the surface of a building structure or household article. In this case, the fog formulation or the total release aerosol is activated in a sealed room to disperse the pesticidal compound in the room space and the pesticidal compound precipitates on the surface of the building structure or household article. Typically, after activating the fog formulation or the total release aerosol formulation, 2-3 hours is sufficient time to settle the pesticidal compound on the surface of the building structure or household article. Typically, when no occupant is present in the room, mist formulations and full release aerosol formulations are used.

When applying the tetrafluorobenzyl ester compound, the tetrafluorobenzyl ester compound is usually applied so that an insecticidal effective amount of the tetrafluorobenzyl ester compound is applied to the surface of the household article or building structure. The application of the tetrafluorobenzyl ester compound may apply 0.1-1000 mg or 1-500 mg of tetrafluorobenzyl ester compound to the surface of the building structure or household article every 1 m ^{3 of the} place of application. The amount is usually sufficient to evaporate an effective amount of the tetrafluorobenzyl ester compound at room temperature in order to inhibit non-existing pests.

Formulations of tetrafluorobenzyl ester compounds typically have one or more tetrafluorobenzyl ester compounds present therein in amounts of 0.001 to 30% by weight, wherein the weight percentages are based on the total weight of the provided formulation.

Aerosol formulations typically have a propellant present therein with the tetrafluorobenzyl ester compound. In the aerosol formulations, the aerosol formulations typically have one or more tetrafluorobenzyl ester compounds present therein in an amount of 0.001-20 wt%, wherein the wt% is based on the total weight of the formulation provided.

As propellant of the aerosol composition, mention may be made of compounds having a boiling point of 25 ° C. or lower, which may give an aerosol formulation which is a homogeneous mixture. Examples of propellants include fluorocarbons such as 1,1-difluoroethane (boiling point -25.0 ° C) and 1,1,1,2-tetrafluoroethane (boiling point -26.2 ° C), dimethyl ether (boiling point -24.8 ° C). ), Propane (boiling point −42.1 ° C.), n-butane (boiling point −0.5 ° C.), isobutane (boiling point −12 ° C.), and the like, and mixtures thereof.

Propellants are usually present in an aerosol formulation in an amount that efficiently sprays at least the tetrafluorobenzyl ester compound onto the surface of a building structure or household article. The amount of propellant present in the aerosol formulation may be at least 20% by weight or 20-99.999% by weight, wherein the weight percentage is based on the total weight of the provided aerosol formulation.

If desired, a solvent may be added thereto, where the boiling point of the solvent is 30-210 ° C. at 1 atmosphere. It is preferable that the boiling point of a solvent is 30-120 degreeC, It is further more preferable that the boiling point of a solvent is 30-100 degreeC, in which the said boiling point is measured at 1 atmosphere. The boiling point of the solvent of 30 to 210 ° C means that the boiling point of all the components for preparing the solvent is substantially in the range of 30 to 210 ° C. When using a mixture of solvents in an aerosol formulation, the aerosol formulation typically has the boiling point of each solvent within the above-mentioned boiling ranges.

Moreover, the aerosol formulations preferably utilize a solvent internally which can provide an aerosol formulation of a homogeneous mixture. If the aerosol formulation is a homogeneous mixture, the aerosol formulation may be in solution, in contrast to the presence of the separated water and oil layers, the emulsion and the suspension. However, the aerosol formulation can also be in this state, in an emulsion state or in a suspension state with a separate water and oil layer.

Examples of the solvent include water (boiling point 100 ° C), 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-propyl alcohol (boiling point 97.2 ° 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 (Idemitsu Petrochemical Company, isoparaffin solvent, boiling point 116-202 ° C) ), IP1016 (Idemitsu Petrochemical Company, isoparaffin solvent, boiling point 73-140 ° C.) and the like can be mentioned. When providing a water based aerosol formulation in a homogeneous mixture, alcohol can also be added thereto as a solvent such as isopropanol.

If used, the solvent is present in the aerosol formulation in an amount of up to 79.9999 wt% and preferably from 5 to 60 wt%, wherein the wt% is based on the total weight of the provided aerosol formulation.

The formulations may be prepared by the prior art. For example, an aerosol formulation can be prepared as follows: One of the tetrafluorobenzyl ester compounds is added to the aerosol container. If necessary, a solvent, another pesticidal active compound, a repellent, a conjugate and / or a stabilizer are also added to the aerosol container. After attaching the aerosol valve to the aerosol container, the propellant is filled through the valve into the aerosol container. The contents in the aerosol container are mixed by stirring the aerosol container and the actuator is secured in the aerosol container.

Oily formulations may be prepared according to the method described in Japanese Patent Laid-Open No. 6-316503.

Water-based liquid formulations can be prepared according to the method described in Japanese Patent Laid-Open No. 6-9305.

Fog preparations can be prepared according to the method described in Japanese Patent Application Laid-Open No. 5-294803.

Heating device formulations may be prepared according to the methods described in JP 2-533332 or JP 6-9305.

The blower preparation can be prepared according to the method described in Japanese Patent Laid-Open No. 11-92303.

Examples of emergency pests include nonsanitary emergency pests and unpleasant emergency pests. More specific examples of unsanitary pests include flies such as housefly ( Musca domestica ) and similar housefly (Muscina stabulans ), mosquitoes such as common mosquitoes (Culex pipiens pallens) , Culex tritaeniorhynchus , Culex quinquefasciatus , Aedes albopictus, and the like. More specific examples of unpleasant pests include the woodpecker (Chironmidae), moth fly (Psychodidae), ant (Formicidae), wasp (Vespidae), Bee, etc. may be mentioned.

Example

Preparation Example 1

1 g of 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R) -trans-3- (1-propenyl (Z / E = 8/1))-2,2-dimethyl Cyclopropanecarboxylate (hereinafter referred to as Compound A) and 69 g of IP1620 (Idemitsu Petrochemical Company, isoparaffin solvent, boiling point 166-202 ° C.) are added to the aerosol container. After attaching the aerosol valve to the aerosol container, 30 g of propellant dimethyl ether are charged into the aerosol container. Stir the contents in the aerosol container well. Aerosol formulation 1 is then prepared by attaching the actuator to the aerosol container.                     

Preparation Example 2-7

Compound A is added to the aerosol container in the amounts shown in Table 1. After attaching the aerosol valve to the aerosol container, the propellant dimethyl ether is charged to the aerosol container in the amounts shown in Table 1. Stir the contents in the aerosol container well. The actuator is then attached to an aerosol container to prepare aerosol formulations 2-7.

Aerosol Formulations # Compound A Amount (g) Dimethyl Ether Amount (g) 2 0.025 99.975 3 0.05 99.95 4 0.1 99.9 5 0.2 99.8 6 0.5 99.5 7 One 99

Preparation Example 8

5 g of Compound A is added to the aerosol container. After attaching the aerosol valve to the aerosol container, 95 g of propellant dimethyl ether are charged to the aerosol container. Stir the contents in the aerosol container well. Aerosol formulation 8 is then prepared by attaching an actuator to the aerosol container.

Preparation Example 9-36

Compound A and solvent are added to the aerosol container in the amounts shown in Tables 2 and 3. The solvent is selected from IP1620 (Idemitsu Petrochemical Company, isoparaffin solvent, boiling point 166-202 ° C.), IP1016 (Idemitsu Petrochemical Company, isoparaffin solvent, boiling point 73-140 ° C.), isopropyl alcohol and hexane. After attaching the aerosol valve to the aerosol container, the propellant dimethyl ether is charged to the aerosol container in the amounts shown in Tables 2 and 3. Stir the contents in the aerosol container well. The actuator is then attached to the aerosol container to prepare aerosol formulations 9-36.

Aerosol Formulations # Compound A Amount (g) Solvent Stimulant type Volume (g) type Volume (g) 9 0.025 IP1620 49.975 Dimethyl ether 50 10 0.05 IP1620 49.95 Dimethyl ether 50 11 0.1 IP1620 49.9 Dimethyl ether 50 12 0.2 IP1620 49.8 Dimethyl ether 50 13 0.5 IP1620 49.5 Dimethyl ether 50 14 One IP1620 49 Dimethyl ether 50 15 5 IP1620 45 Dimethyl ether 50 16 0.025 IP1016 49.975 Dimethyl ether 50 17 0.05 IP1016 49.95 Dimethyl ether 50 18 0.1 IP1016 49.9 Dimethyl ether 50 19 0.2 IP1016 49.8 Dimethyl ether 50 20 0.5 IP1016 49.5 Dimethyl ether 50 21 One IP1016 49 Dimethyl ether 50 22 5 IP1016 45 Dimethyl ether 50 23 0.025 Isopropyl Alcohol 49.975 Dimethyl ether 50 24 0.05 Isopropyl Alcohol 49.95 Dimethyl ether 50 25 0.1 Isopropyl Alcohol 49.9 Dimethyl ether 50 26 0.2 Isopropyl Alcohol 49.8 Dimethyl ether 50 27 0.5 Isopropyl Alcohol 49.5 Dimethyl ether 50 28 One Isopropyl Alcohol 49 Dimethyl ether 50 29 5 Isopropyl Alcohol 45 Dimethyl ether 50

Aerosol Formulations # Compound A Amount (g) Solvent Stimulant type Volume (g) type Volume (g) 30 0.025 Hexane 49.975 Dimethyl ether 50 31 0.05 Hexane 49.95 Dimethyl ether 50 32 0.1 Hexane 49.9 Dimethyl ether 50 33 0.2 Hexane 49.8 Dimethyl ether 50 34 0.5 Hexane 49.5 Dimethyl ether 50 35 One Hexane 49 Dimethyl ether 50 36 5 Hexane 45 Dimethyl ether 50

Preparations 37-73

Using LPG instead of dimethyl ether, aerosol formulations 37-73 are prepared analogously to preparations 9-36.

Preparation Example 74

An oily formulation is prepared by dissolving 2.67 g of Compound A in 97.33 g of IP1620 (Idemitsu Petrochemical Company, isoparaffin solvent, boiling point 166-202 ° C.). 3.6 g of oily formulation is added to the aerosol container. After attaching the aerosol valve to the aerosol container, 8.4 g of the liquefied propellant gas mixture of LPG and dimethyl ether are charged to the aerosol container. Stir the contents in the aerosol container well. Aerosol formulation 74 is then prepared by attaching the actuator to the aerosol container.

Preparation 75

0.025 g of Compound A and 49.975 g of a solvent mixture of water and isopropanol, where the weight to weight ratio is 1: 1, are added to the aerosol container. After attaching the aerosol valve to the aerosol container, 50 g of dimethyl ether is charged to the aerosol container. Stir the contents in the aerosol container well. The actuator is then attached to an aerosol container to prepare aerosol formulation 75.

Preparation Example 76

1 g of 2,3,5,6-tetrafluoro-4-methylbenzyl (1R) -trans-3- (1-propenyl (Z / E = 8/1))-2,2-dimethylcyclopropane Carboxylate (hereinafter referred to as compound B) and 69 g of IP1620 (Idemitsu Petrochemical Company, isoparaffin solvent, boiling point 166-202 ° C) are added to the aerosol container. After attaching the aerosol valve to the aerosol container, 30 g of propellant dimethyl ether are charged to the aerosol container. Stir the contents in the aerosol container well. The actuator is then attached to the aerosol container to prepare aerosol formulation 76.

Preparation 77-82

Using Compound B instead of Compound A, aerosol formulations 77-82 are prepared similarly to Preparations 2-7.

Preparation Example 83-151

Using Compound B instead of Compound A, aerosol formulations 83-151 are prepared similarly to Preparations 8-76.

Comparative Production Example 1

Using Empentrin instead of Compound A, Comparative Aerosol Formulation 1 is prepared similarly to Preparation 7.

Comparative Production Example 2                     

Using Permethrin instead of Compound A, Comparative Aerosol Formulation 2 is prepared similarly to Preparation 7.

Test Example 1

Hang a nylon curtain 1 m ² and open it from a glass window 140 cm high from the floor in the 5.8 m ³ laboratory (internal dimensions: 1.8 m wide, 1.8 m long, 1.8 m high, where 1 of the 4 surfaces of the wall is glass) . From a position 20 cm away from the curtain, aerosol 7 is sprayed uniformly directly onto the nylon curtain for 6 seconds. The amount of aerosol formulation 7 nebulized is determined by measuring the amount of reduction in the total amount of aerosol composition 7 from before and after spraying the aerosol formulation 7. The laboratory is then ventilated with an exhaust blower for 10 minutes. Stop internal closing and seal. The next day (after 1 day), the room is ventilated for a second time for 10 minutes, after which 20 adult male and female houseflies are released to the laboratory. The knockdown number of the housefly is periodically observed at a predetermined time. In addition, two days after spraying aerosol formulation 1 and three days after spraying aerosol formulation 1, the laboratory was evacuated in the lab by tertiary and quaternary ventilation respectively to empty the housefly. After the fourth ventilation, 20 adult male and female house flies are released into the laboratory a second time. The knockdown number of the housefly is periodically observed at a predetermined time. Based on the knockdown number, the time required to knock down half of the housefly is measured the next day and three days later (KT ₅₀ ).

Furthermore, the test is repeated with aerosol formulation 83, comparative aerosol formulation 1 and comparative aerosol formulation 2, respectively.

The results are shown in Table 4 below.

Spray amount (g) KT ₅₀ value (minutes) 1 day later 3 days later Aerosol Formulations 1 3.2 2.5 3.3 Aerosol Formulations 83 3.3 3.2 5.0 Comparative Aerosol Formulations 1 3.5 9.6 > 20 Comparative Aerosol Formulations 2 3.4 > 20 > 20

The results in Table 4 demonstrate that aerosol formulations 7 and 83 provide a knockdown effect after 3 days of spraying the aerosol formulations 7 and 83. Moreover, the results in Table 4 demonstrate that Comparative Aerosol Formulations 1 and 2 provide insufficient knockdown effects after 3 days of spraying of Comparative Aerosol Formulations 1 and 2.

Test Example 2

Using aerosol formulations 1, 8, 14, 15, 21, 22, 28, 29, 35, 36, 76, 82, 88, 89, 96, 97, 103, 104, 110, and 111 instead of aerosol formulation 1 or 83 , The knockdown effect can be achieved according to the method described in Test Example 1.

The present invention enables the application of tetrafluorobenzyl ester compounds to the surface of building structures or household articles, thereby suppressing non-commercial pests in indoor environments.

Claims (5)

A method of inhibiting flies or mosquitoes in an indoor environment, comprising applying a tetrafluorobenzyl ester compound represented by the following formula (1) to the surface of a building structure or household article: [Formula 1]

[Wherein, R represents a methyl group or a methoxymethyl group]. The method of claim 1 comprising spraying an aerosol composition comprising a propellant and a tetrafluorobenzyl ester compound represented by Formula 1 on the surface of a building structure or household article. The method of claim 2 wherein the aerosol composition further comprises a solvent having a boiling point of 30 to 210 ° C. The method of claim 1, wherein the building structure and household articles are selected from fixtures of the building and mobile furniture products. delete