JP3008603B2 - Insecticidal composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

FIELD OF THE INVENTION The present invention relates to insecticidal aerosol compositions.

[0002]

BACKGROUND OF THE INVENTION Problems to be Solved by the Invention

Embedded image 2,4-dioxo-1- (2-propynyl) represented by
Imidazolidin-3-ylmethyl chrysanthemate (hereinafter referred to as compound A) is described in JP-B-60-9715.
It is known that these compounds can be used as an active ingredient of an insecticide, but it has been considered that the compounds are not necessarily sufficient in insecticidal efficacy.

[0003]

Means for Solving the Problems The present inventors have prepared a compound A
As a result of intensive studies on the enhancement of the insecticidal activity and the improvement of the formulation, the compound A was mixed with a monocarboxylic acid ester having 16 to 19 carbon atoms and / or a dicarboxylic acid ester having 16 to 19 carbon atoms in a weight ratio of 3: 1 to 3: 1. It was found that the insecticidal efficacy was enhanced by the addition at a ratio of 1: 100. And furthermore, kerosene and dimethyl ether,
It has been found that by adding liquefied petroleum gas as needed, an aerosol composition in which the insecticidal effect of compound A is greatly enhanced can be obtained, and the present invention has been completed. That is, the present invention provides a) a compound A 0.001 to 5% by weight, b) one or more monocarboxylic acid esters having 16 to 19 carbon atoms and / or dicarboxylic acid esters having 16 to 19 carbon atoms.
A pesticidal aerosol composition characterized in that it contains from 20 to 80% by weight of 005 to 60% by weight, c) 5 to 80% by weight of kerosene and d) 20 to 80% by weight of a propellant consisting of dimethyl ether or a mixture of dimethyl ether and liquefied petroleum gas. Less than,
It is described as the composition of the present invention. ).

Compound A has various optical isomers and geometric isomers, and any isomer having insecticidal activity among them and a mixture thereof can be used in the present invention. The content of the compound A in the composition of the present invention is 0.001 to 5% by weight,
Preferably it is 0.05 to 2% by weight. Examples of the mono- or dicarboxylic acid ester having 16 to 19 carbon atoms used in the composition of the present invention include dibutyl phthalate, isopropyl palmitate, isopropyl myristate, hexyl laurate and the like. These may be used alone or in combination of two or more, and the content in the composition of the present invention is 0.05 to 60% by weight, preferably 0.1 to 40% by weight. Kerosene used in the composition of the present invention,
Any solvent commonly used as a solvent for the insecticide aerosol can be used, for example, n-paraffin-based ones such as neothiozole (Kerosen manufactured by Chuo Kasei Co., Ltd.), Isopar G, Isopar H, Isopar M (Kerosen manufactured by Exxon Chemical Co., Ltd.) , IP-2028 (Kerocene manufactured by Idemitsu Petrochemical Co., Ltd.) or a mixture thereof. The content of kerosene in the composition of the present invention is 5 to 80% by weight, preferably 30 to 70% by weight. The propellant used in the composition of the present invention is dimethyl ether or a mixture of dimethyl ether and liquefied petroleum gas, and the mixing ratio of dimethyl ether and liquefied petroleum gas is preferably in the range of 100: 0 to 40:60 by weight. . The content of the propellant in the composition of the present invention is 20 to 80% by weight, preferably 30 to 70% by weight.

[0005] The composition of the present invention may further contain other insecticidal active ingredients, synergists, fragrances, fungicides and the like.
Other insecticidal active ingredients include, for example, (RS) -3-allyl-2-methyl-4-oxocyclopent-2-enyl (1RS) -cis, trans-chrysanthemate [aresulin] 3,4,5 6-tetrahydrophthalimidomethyl
(1RS) -cis, trans-chrysanthemate [tetramethrin] (S) -2-methyl-4-oxo-3- (2-propynyl) cyclopent-2-enyl (1R) -cis, trans-chrysanthemate [ Pralesulin] 3-phenoxybenzyl (1RS) -cis, trans-chrysanthemate [phenothrin] 5-benzyl-3-furylmethyl (1RS) -cis,
Trans-chrysanthemate [resmethrin] (RS) -α-cyano-3-phenoxybenzyl (1
R) -cis, trans-chrysanthemate [cyphenothrin] 3-phenoxybenzyl (1RS) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate [permethrin] (RS ) -Α-cyano-3-phenoxybenzyl (1
RS) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate [cypermethrin] (S) -α-cyano-3-phenoxybenzyl (1
R) -cis-3- (2,2-dibromovinyl) -2,2
-Dimethylcyclopropanecarboxylate [deltamethrin] (RS) -α-cyano-4-fluoro-3-phenoxybenzyl (1RS) -cis, trans-3- (2,2
-Dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate [cyfluthrin] 5- (2-propynyl) furfuryl (1RS) -cis, trans-chrysanthemate [flamesurin] 2- (4-ethoxyphenyl) -2- Methyl propyl
3-phenoxybenzyl ether [ethofenprox] 2,3,5,6-tetrafluorobenzyl (1R)-
Trans- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate [benfluthrin]

2,2-dichlorovinyl dimethyl phosphate [dichloro boss] O, O-dimethyl O- (3-methyl-4-nitrophenyl) phosphorothioate [fenitrothion] 2- (1-methylethoxy) phenyl N -Methylcarbamate [propoxer] 4-phenoxyphenyl (RS) -2- (2-pyridyloxy) propyl ether [pyriproxifene] isopropyl (2E, 4E) -11-methoxy-3,
7,11-trimethyl-2,4-dodecadienoate [mesoprene] ethyl (2E, 4E) -3,7,11-trimethyl-
2,4-dodecadienoate [hydroprene] 1- (4-chlorophenyl) -3- (2,6-difluorobenzoyl) urea [diflubenzuron] N-cyclopropyl-1,3,5-triazine-2,
4,6-triamine [cyromazine] and the like are usually contained in the composition of the present invention in an amount of 0 to 3% by weight, preferably 0 to 2% by weight.

As the synergist, for example, α- [2- (2-butoxyethoxy) ethoxy] -4,
5-methylenedioxy-2-propyltoluene [piperonylbutoxide] N- (2-ethylhexyl) -bicyclo [2.2.1]
Hept-5-ene-2,3-dicarboximide [MG
K-264] octachlorodipropyl ether [S-421] and the like, which are usually contained in the composition of the present invention in an amount of 0 to 4% by weight, preferably 0 to 2% by weight.

The composition of the present invention comprises, for example, a predetermined amount of compound A, the above-mentioned carboxylic acid ester, and if necessary, other insecticidal active ingredients, synergists, fragrances, bactericides, etc., added to kerosene at room temperature or under heating. It can be obtained by mixing or dissolving, placing this in an aerosol container, attaching a valve portion to the container, and filling the propellant with pressure through the valve portion.

Pests effective for the composition of the present invention include the following. Lepidopteran pests, moths, moths, etc. Diptera pests, house mosquitoes such as Culex pipiens, Culex pipiens, Aedes such as Aedes aegypti, Aedes albopictus, Anopheles such as Aedes aegypti, house flies such as house flies, house flies, house flies, and a house fly
Anopheles, magpies, onions and other flies, fruit flies, Drosophila, Drosophila, tabbys, blackflies, sand flies, etc. Reticulate pests German cockroaches, black cockroaches, brown cockroaches, brown cockroaches, brown cockroaches, brown cockroaches
House cockroaches, mountain cockroaches, Japanese cockroaches, etc. Hymenoptera pests Ants, wasps, stag bees, etc., etc. Isoptera pests Yamato termites, house termites, etc. Ticks Oxodid mites Dust mites, dust mites , Mites, house dust mites, etc.

[0010] The composition of the present invention is extremely effective in controlling cockroaches, which are insects of the order of the order Aphides. In other words, although many aerosols for controlling cockroaches are currently on the market, cockroaches are quickly hidden in the shade after spraying the aerosol. The composition of the present invention is capable of knocking down a cockroach without giving time to escape due to its rapid knockdown effect, and can be used as an epoch-making cockroach controlling agent.

[0011]

The present invention will be described below in more detail with reference to production examples and test examples. In the following production examples, parts represent parts by weight. Production Example 1 Compound A 0.5 part, isopropyl myristate 0.
5 parts, 45 parts of neothiozole and Isopar G 14
Of a propellant (a mixture of dimethyl ether and liquefied petroleum gas in a weight ratio of 90:10) was charged through the valve portion to obtain a composition (1) of the present invention. . Production Example 2 Compound A 0.5 part, isopropyl myristate 0.
5 parts and 59 parts of neothiozole are put into an aerosol can, a valve part is attached to the can, and a propellant (a weight ratio of dimethyl ether and liquefied petroleum gas of 75:25) is passed through the valve part.
The mixture of the present invention (40 parts) was obtained to obtain a composition (2) of the present invention. Production Example 3 Compound A 0.5 part, isopropyl myristate 0.
5 parts and 59 parts of neothiozole are put into an aerosol can, and a valve part is attached to the can, and a propellant (50:50 by weight of dimethyl ether and liquefied petroleum gas) is passed through the valve part.
The mixture of the present invention (40 parts) was obtained to obtain a composition (3) of the present invention. Production Example 4 Compound A 0.5 part and isopropyl myristate 3
0.5 part and 29 parts of neothiozole are dissolved in an aerosol can, a valve portion is attached to the can, and 40 parts of a propellant (a 50:50 mixture by weight of dimethyl ether and liquefied petroleum gas) is filled through the valve portion. Thus, a composition (4) of the present invention was obtained. Production Example 5 2.0 parts of compound A and isopropyl myristate 32
Is dissolved in 26 parts of neothiozole and placed in an aerosol can. A valve is attached to the can, and the propellant (weight ratio of dimethyl ether and liquefied petroleum gas: 50:
The mixture of the present invention (40 mixtures) was filled with 40 parts to obtain a composition (5) of the present invention. Production Example 6 Compound A 0.1 part, tetramethrin 2.0 part and isopropyl myristate 30.1 part were prepared using Isopar M
Dissolved in 27.8 parts and placed in an aerosol can. A valve portion was attached to the can, and a propellant (a 50:50 mixture by weight of dimethyl ether and liquefied petroleum gas) was passed through the valve portion.
The composition was filled to obtain a composition (6) of the present invention.

Production Example 7 0.1 part of compound A, (RS) -3-allyl-2-methyl-4-oxocyclopent-2-enyl (1RS)
-Place cis, trans (c: t = 20: 80) -chrysanthemate 1.0 part, isopropyl myristate 0.1 part and Isopar H 58.8 parts in an aerosol can,
A valve portion was attached to the can, and 40 parts of a propellant (a 50:50 mixture by weight of dimethyl ether and liquefied petroleum gas) was filled through the valve portion to obtain a composition (7) of the present invention. Production Example 8 0.1 part of compound A, 0.1 part of praresulin, 0.1 part of isopropyl myristate, and Isopar M5
9.7 parts were put in an aerosol can, a valve part was attached to the can, and 40 parts of a propellant (a 50:50 mixture by weight of dimethyl ether and liquefied petroleum gas) was filled through the valve part, and the composition of the present invention (8) was obtained. I got Production Example 9 Compound A 0.1 part, d-phenothrin 0.1 part, isopropyl myristate 0.1 part and IP-2028
59.7 parts were put in an aerosol can, a valve portion was attached to the can, and 40 parts of a propellant (a 50:50 mixture by weight of dimethyl ether and liquefied petroleum gas) was filled through the valve portion, and the composition (9) of the present invention was obtained. I got Production Example 10 Compound A 0.1 part, cyfenosulin 0.3 part, isopropyl myristate 0.1 part, and Isopar M 5
9.5 parts was put in an aerosol can, a valve portion was attached to the can, and 40 parts of a propellant (a 50:50 mixture of dimethyl ether and liquefied petroleum gas) was filled through the valve portion, and the composition of the present invention (10) was obtained. I got Production Example 11 0.1 part of Compound A, 0.3 part of cypermethrin, 0.1 part of isopropyl myristate and 40 parts of dibutyl phthalate were dissolved in 19.5 parts of Isopar M, put in an aerosol can, and a valve portion was placed in the can. And 40 parts of a propellant (a 50:50 mixture by weight of dimethyl ether and liquefied petroleum gas) was charged through the valve portion, and the composition of the present invention (1
1) got. Production Example 12 0.1 part of Compound A, 0.025 part of cyfluthulin, 0.1 part of isopropyl myristate, and 40 parts of hexyl laurate were dissolved in 19.775 parts of Isopar M and placed in an aerosol can. 40 parts of a propellant (a 50:50 mixture by weight of dimethyl ether and liquefied petroleum gas) was filled through the valve part to obtain a composition (12) of the present invention.

Production Example 13 Compound A 0.1 part, Etofenprox 0.3 part,
0.1 part of isopropyl myristate and 40 parts of isopropyl palmitate are dissolved in 19.5 parts of Isopar M and placed in an aerosol can. A valve is attached to the can, and a propellant (weight of dimethyl ether and liquefied petroleum gas is passed through the valve). The mixture was charged with 40 parts of a 50:50 mixture (ratio 50:50) to obtain a composition (13) of the invention. Production Example 14 Compound A 0.1 part, dichloroboss 0.5 part and isopropyl myristate 30.1 part were prepared by isopar M 2
Dissolve in 9.3 parts, put in an aerosol can, attach a valve part to the can, fill 40 parts of propellant (50:50 mixture by weight of dimethyl ether and liquefied petroleum gas) through the valve part and the composition of the present invention (14) was obtained. Production Example 15 0.1 part of Compound A, 0.5 part of fenitrothion and 30.1 parts of isopropyl myristate are dissolved in 29.3 parts of Isopar M and placed in an aerosol can. A valve is attached to the can, and the can is injected through the valve. Agent (50:50 mixture by weight of dimethyl ether and liquefied petroleum gas) 4
0 part was filled to obtain the composition (15) of the present invention. Production Example 16 Compound A 0.1 part, propoxer 0.5 part and isopropyl myristate 30.1 part were prepared using Isopar M 2
Dissolve in 9.3 parts, put in an aerosol can, attach a valve part to the can, fill 40 parts of propellant (50:50 mixture by weight of dimethyl ether and liquefied petroleum gas) through the valve part and the composition of the present invention (16) obtained. Production Example 17 0.1 part of Compound A, 0.1 part of pyriproxyfen and 30.1 parts of isopropyl myristate are dissolved in 29.7 parts of Isopar M and placed in an aerosol can, and a valve part is attached to the can and the valve part is attached. Propellant (50:50 mixture by weight of dimethyl ether and liquefied petroleum gas)
The composition of the present invention (17) was obtained by charging 40 parts. Production Example 18 Compound A 0.1 part, mesoprene 0.1 part and isopropyl myristate 30.1 part were prepared by isopar M 3
The composition of the present invention was dissolved in 9.7 parts and placed in an aerosol can. A valve was attached to the can and 30 parts of a propellant (a 50:50 mixture by weight of dimethyl ether and liquefied petroleum gas) was filled through the valve. (18) was obtained.

Production Example 19 0.1 part of Compound A, 0.1 part of diflubenzuron and 30.1 parts of isopropyl myristate are dissolved in 39.7 parts of Isopar H, and the mixture is placed in an aerosol can. 30 parts of a propellant (dimethyl ether) was charged through the portion to obtain a composition (19) of the present invention. Production Example 20 Compound A 0.1 part, cyromazine 0.1 part and isopropyl myristate 30.1 part were converted to Isopar H 3
The mixture was dissolved in 9.7 parts and placed in an aerosol can. A valve was attached to the can, and 30 parts of a propellant (dimethyl ether) was filled through the valve to obtain a composition (20) of the present invention. Production Example 21 Compound A 0.1 part, piperonyl butoxide 0.5
Parts, 0.1 part of isopropyl myristate and 29.3 parts of neothiozole are placed in an aerosol can, a valve part is attached to the can, and a propellant (a 75:25 mixture by weight of dimethyl ether and liquefied petroleum gas) is passed through the valve part.
The composition was filled to obtain a composition (21) of the present invention. Production Example 22 Compound A 0.1 part, S-421 0.5 part, isopropyl myristate 0.1 part and neothiozole 2
9.3 parts were put in an aerosol can, a valve portion was attached to the can, and 70 parts of a propellant (a mixture of dimethyl ether and liquefied petroleum gas in a weight ratio of 75:25) was filled through the valve portion, and the composition of the present invention (22) was obtained. I got Production Example 23 Compound A 0.1 part, MGK-264 2 parts, isopropyl myristate 0.1 part, and neothiozole 2
7.8 parts are placed in an aerosol can, a valve part is attached to the can, and 70 parts of a propellant (a mixture of dimethyl ether and liquefied petroleum gas at a weight ratio of 75:25) is filled through the valve part to obtain the composition (23) of the present invention. I got Production Example 24 Compound A 0.1 part, benfluthrine 0.1 part and isopropyl myristate 30.1 part were prepared using Isopar M.
Dissolved in 29.7 parts and placed in an aerosol can. A valve was attached to the can, and a propellant (50:50 mixture by weight of dimethyl ether and liquefied petroleum gas) was passed through the valve.
The composition was filled to obtain a composition (17) of the present invention.

Next, the insecticidal efficacy of the composition of the present invention will be shown by test examples. Test Example 1 A cylindrical test container having a diameter of 13 cm and a height of 10 cm (the bottom was 4 cm)
It is a 0-mesh wire mesh and floats about 1 cm above the floor.)
10 cockroaches (5 males and 5 females) were released. Next, the test container was placed in a glass cylinder having a diameter of 20 cm and a height of 60 cm, and a predetermined amount (0.4 g) of aerosol was sprayed from above onto the German cockroach, and the glass cylinder was immediately covered with a lid. Thirty seconds later, the test container was taken out, and after spraying, the number of knockdown insects was counted at 1, 2, 3, 5, 7, 10, 15 and 20 minutes, respectively, and the KT ₅₀ value was measured by the Probit method of Bries. (Time required for 50% of German cockroaches to knock down) was determined. The KT ₅₀ values thus determined are shown in Table 1 below.

[Table 1]

After 20 minutes from the spraying, all the German cockroaches were transferred to another container, and after 3 days, the mortality was determined. The compositions obtained in Production Examples 1 to 5 and 10 to 16 were all 100%. Mortality rate. In the above Test Example 1, as the compound A, an isomer having an acid side of d-cis and trans isomer (cis, trans ratio is about 20:80) was used.

Test Example 2 Compound A (d-cis, trans isomer on the acid side (cis, trans ratio is about 20:80)) 0.5 parts by weight, isopropyl myristate 30.5 parts by weight, neothiozole 29 parts by weight, dimethyl ether
Using 20 parts by weight and 20 parts by weight of liquefied petroleum gas, an aerosol was obtained in the same manner as in Production Example 4. At the center of the sheet having several concentric circles with a radius of 0.1 m to 1.4 m, a plastic ring with an inner wall buttered was placed, into which 10 German cockroaches or 6 German cockroaches were released. The above-mentioned aerosol was directly sprayed on German cockroaches for 1 second and on German cockroaches for 3 seconds. The plastic ring was removed immediately after the spraying, and the distance from the spraying point to the point where the cockroach was knocked down was measured. The cockroaches that moved 1.4 m or more were promptly collected. The test was performed five times, and the moving distance until the cockroach knocked down was determined from the average value (median). Table 2 shows the results. Table 2 also shows the results of similar tests conducted using commercially available aerosols for controlling cockroaches (proxor / dichloroboth as an active ingredient and d-phthalsulin / permethrin as an active ingredient). Show.

[0018]

[Table 2]

Next, compound A is a monocarboxylic acid ester having 16 to 19 carbon atoms and / or a compound having 16 to 19 carbon atoms.
The addition of the dicarboxylic acid ester of Example 1 shows that the insecticidal effect is enhanced by reference to Reference Examples. Reference Production Example 50 parts of compound A (acid side is d-cis, trans form (cis, trans ratio is about 20:80)) and 50 parts of isopropyl myristate are mixed and dissolved under heating to obtain Reference Composition 3. Was. Table 3 shows the reference compositions obtained in the same manner.

[0020]

[Table 3]

Reference Test Example 1 0.3 ml of an acetone diluted solution of each of the compositions shown in Table 2 was added to 8.5 cm in diameter.
Compound A was applied to a glass dish at a concentration of 10 mg / m ² , air-dried, and 10 German cockroaches were released.
It was examined T ₅₀ value (time required for knocking down 50% of the insects). Table 4 shows the results.

[Table 4]

[0022]

The insecticidal aerosol composition of the present invention comprises:
It enhances the insecticidal activity of 2,4-dioxo-1- (2-propynyl) imidazolidin-3-ylmethyl chrysanthemate, and is effective for controlling various pests.

Continuation of the front page (51) Int.Cl. ⁷ identification code FI A01N 27:00 31:14) (56) References JP-A-4-9306 (JP, A) JP-A-3-209303 (JP, A) JP-A-2-28811 (JP, A) JP-A-54-9269 (JP, A) JP-A-2-142704 (JP, A) JP-A-54-23123 (JP, A) (58) (Int.Cl. ⁷ , DB name) A01N 53/04 A01N 25/06 A01N 37/10 A01N 37/02

Claims (3)

(57) [Claims] 1. a) 0.001 to 5% by weight of 2,4-dioxo-1- (2-propynyl) imidazolidin-3-ylmethyl chrysanthemate; b) one or more C16
Propellant comprising 0.005 to 60% by weight of a monocarboxylic acid ester of -19 to 19 and / or dicarboxylic acid ester of 16 to 19 carbon atoms, c) 5-80% by weight of kerosene and d) dimethyl ether or a mixture of dimethyl ether and liquefied petroleum gas. Insecticidal aerosol composition characterized by containing 20 to 80% by weight 2. The insecticidal aerosol composition according to claim 1, wherein at least one of the carboxylic esters is dibutyl phthalate, isopropyl palmitate, isopropyl myristate or hexyl laurate. 3. The insecticidal aerosol composition according to claim 1, wherein the weight ratio of dimethyl ether to liquefied petroleum gas of the propellant is from 100: 0 to 40:60.