NL9100673A - INSECTICIDE COMPOSITIONS. - Google Patents

Description

EXTRACT

The insecticidal composition of the present invention contains (a) 2,4-dioxo-1- (2-propynyl) -imidazolidin-3-ylmethyl chrysanthemate and (b) at least one carboxylic acid ester selected from the group of monocarboxylic acid esters of 16-19 carbon atoms and dicarboxylic acid ester with 16-19 carbon atoms, the weight ratio of (a) to (b) being from 3: 1 to 1: 100. The addition of (b) remarkably enhances the insecticidal activity of (a).

Insecticide compositions.

The invention relates to an insecticidal composition.

2,4-Dioxo-1- (2-propynyl) imidazolidin-3-ylmethyl-chrysanthemate of the formula (hereinafter referred to as Compound A), is a compound disclosed in U.S. Patent 4,176,189, and is known as being useful as an active ingredient for insecticides. However, the compound does not show satisfactorily high insecticidal activity when used alone.

The present invention is now based on extensive studies to enhance the insecticidal activity of Compound A, and as a result, it has been found that when (b) at least one carboxylic acid ester is selected from the group of monocarboxylic acid esters of 16 to 19 carbon atoms and dicarboxylic acid esters with 16 to 19 carbon atoms, are added to (a) compound A, such that the weight ratio of (a) to (b) is from 3: 3 to 1: 100, the insecticidal activity of compound A is remarkably enhanced .

Accordingly, according to the invention, an insecticide composition is provided, characterized in that it comprises: a) 2,4-dioxo-1- (2-propynyl) imidazolidin-3-ylmethyl-chrysanthemate (compound A), b) at least one member selected from the group of mono-carboxylic acid esters with 16 to 19 carbon atoms and dicarboxylic acid esters with 16 to 19 carbon atoms, the weight ratio of (a) to (b) being from 3: 1 to 1: 100, and optionally c) ten at least one inert carrier.

Compound A has various optical and geometric isomers. Of these isomers, an isomer exhibiting insecticidal activity, as well as mixtures thereof, can be incorporated into the insecticidal composition of the invention. The content of compound A in the composition of the invention is usually 0.001 to 75 wt. %.

Specific examples of the monocarboxylic acid esters of 16 to 19 carbon atoms and the dicarboxylic acid esters of 16 to 19 carbon atoms are dibutyl phthalate, isopropyl palmitate, isopropyl myristate, hexyl laurate, etc. These compounds can also be used in admixture thereto. One or more compounds selected from these compounds are usually mixed in the composition of the present invention in an amount of 0.0003 to 75 wt. %.

One or more other insecticides, synergists, perfumes, fungicides, solvents, propellants, solid carriers, etc., may be incorporated into the composition of the invention.

Specific examples of these other insecticides are: (RS) -3-allyl-2-methyl-4-oxocyclopent-2-enzyl (1RS) -cis, trans-chrysanthemate [allethrin]; 3,4,5,6-tetrahydrofthalimidomethyl (1RS) -cis, trans-chrysanthemate [tetramethrine]; (S) -2-methyl-4-oxo-3- (2-propynyl) cyclopent-2-enyl (IR) -cis, trans-chrysanthemate [prallethrine]; 3-phenoxybenzyl (1RS) -cis, trans-chrysanthemate [phenothrine]; 5-benzyl-3-furylmethyl (1RS) -cis, trans-cryshemate [resmethrine]; (RS) -a-cyano-3-phenoxybenzyl (IR) -cis, trans-chrysanthemate [cyphenotrhine]; 3-phenoxybenzyl (1RS) -cis, trans-3- (2,2) -dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate [permethrin]; (RS) -a-cyano-3-phenoxybenzyl (1RS) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate [cypermethrin]; (S) -a-cyano-3-phenoxybenzyl (1R) -cis-3- (2,2) -dibromovinyl) -2,2-dimethylcyclopropanecarboxylate [deltamethrine]; (RS) -a-cyano-4-fluoro-3-phenoxybenzyl (1RS) -cis, trans-3- (2,2) -dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate [cyfluthrine]; 5- (2-propynyl) furufuryl (IRS) cis, trans-chrysanthemate [furamethrine]; 2- (4-ethoxyphenyl) -2-methylpropyl-3-phenoxybenzylether [ethophenprox]; 2,2-dichlorovinyl dimethyl phosphate [dichlorvos]; 0, O-dimethyl 0- (3-methyl-4-nitrophenyl) -phosphororthioate [fenitrothion]? 2- (1-methylethoxy) phenylmethyl carbamate [propoxur), 4-phenoxyphenyl (RS) -2- (2-pyridyloxy) propyl ether [pyriproxyphen]; isopropyl (2E, 4E) -1-methoxy-3,7,11-trimethyl-2,4-dodecadienoate [methoprene]; ethyl (2E, 4E) -3,7,11-trimethyldodeca-2,4-dienoate [hydroprene]; 1- (4-chlorophenyl) -3- (2,6-difluorobenzoyl) urea [diflubenzuron]; and N-cyclopropyl-1,3,5-triazine-2,4,6-triamine [cyromazine].

Specific examples of the synergists are α- [2- (2-butoxyethoxy) ethoxy] -4,5-methylenedioxy-2-propyltoluene (piperonyl butoxide), N- (2-ethylhexyl) bicyclo [2,2,1] hept -5-en-2,3-dicarboximide (MGK-264), octachlorodipropyl ether (S-421), etc.

Specific examples of the solvents are isopropyl alcohol, kerosene, dodecylbenzene, etc.

Specific examples of the propellants are propane / butane, dimethyl ether, Freon GAS (fluorocarbons), etc.

The composition of the invention is prepared, for example, by mixing a prescribed amount of compound A and a prescribed amount of at least one carboxylic acid ester as described above, and, if necessary, other insecticides, synergists, perfumes, fungicides, solvents, propellants, solid carriers, etc. at room temperature or under heating.

Insects and acarina, against which the composition of the invention thus prepared is active, are stated below:

Lepidoptera

Cocoon-making clothes moth (Tinea pellionellat,

Weaving clothes moth (Tineola bisselliellat f etc.

Diptera

Culex species such as common mosquito (Culex pipiens pallens) and Culex tritaeniorhynchus: Aedes species such as Aedes aegypti; and Aedes albopictus; Anopheles species such as Anopheles sinensis mosquitoes (Chironomedae),

Muscidae such as house fly (Museums domestical and false stable fly (Muscina stabulanst; Calliphoridae; Sarcophagidae; small house fly (Fannia canicularis1; Anthomyiidae such as corn worm (Delia platura) and onion worm (Delia antiaual; fruit flies (Tephritidea); Drosophilidae); Drosophilidae) (Simuliidae); Tabanidae; stable flies (Stomoxyidae) etc.

Dictyoptera

German cockroach (Blattella crermanicat, smoky brown cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americanal, brown cockroach (Periplaneta brunnea), oriental cockroach (Blatta orientalist, etc.)

Hymenoptera ants (Formicidae), hornets (Vespidae), Bethylidae, wasps (Tenthredinidae) such as the cabbage wasp (Anthalia rosae ruficornist. Etc.

Isoptera

Reticulitermes speratusf Coptotermes formosanus. etc. Ixodidae

Boophilus microplusf etc. dust lice

Acaridae such as Tvrophaaus putrescentiae f Pyroalyphidae such as Dermatophaaoides farinae. Cheyletidae such as Chelacaropsis moorei, Macronyssidae such as Ornithonyssus bacoti. etc.

The composition of the invention can be used as is to kill the insect pests; however, it is usually used formulated in the form of a preparation such as aerosols, oil sprays, etc.

In the latter case, the content of compound A in the aerosols or in the oil sprays is preferably 0.001 wt. % to 5 wt. %.

The invention is illustrated in more detail with reference to the following examples, comparative examples and a test example; however, the invention is not to be understood as being limited thereto.

In the examples, comparative examples and the test example, all parts are parts by weight.

Example I

50.0 parts of compound A (acid part: d-trans configuration) and 50.0 parts of isopropyl myristate were mixed under heating (about 40 to 50 ° C) to obtain a liquid insecticide composition.

Table A lists the insecticidal compositions obtained in the same manner as above.

TABLE A

Example VIII

0.1 parts of compound A, 0.1 parts of isopropyl myristate and 0.3 parts of cyphenothrine were dissolved in a mixture of 20 parts of dodecylbenzene and 39.5 parts of kerosene. The resulting mixture was placed in a container. A mouthpiece was placed on the container. 40.01 parts of a propane-butane propellant mixture was pressed through the nozzle into the insecticide composition to obtain an aerosol.

Example IX

1.0 parts of compound A and 1.0 parts of isopropyl myristate were dissolved in a mixture of 20.0 parts of isopropyl alcohol and 28.0 parts of kerosene. The resulting mixture was placed in a container. A mouthpiece was placed on the container. 50.0 parts of a propane, butane and dimethyl ether propellant mixture was forced through the nozzle into the insecticide composition to obtain an aerosol.

Example X.

1.0 parts of compound A and 31.0 parts of isopropyl myristate were dissolved in 18.0 parts of kerosene. The resulting mixture was placed in a container. A mouthpiece was placed on the container. 50.0 parts of a propellant mixture of propane, butane and dimethyl ether were passed through the; nozzle pressed into the insecticide composition to obtain an aerosol.

Example XI

1.0 parts of compound A and 1.0 parts of dibutyl phthalate were dissolved in a mixture of 2.5 parts of isopropyl alcohol and 45.5 parts of dodecylbenzene. The resulting mixture was placed in a container. A mouthpiece was placed on the container. 50.0 parts of a propane, butane and dimethyl ether propellant mixture was forced through the nozzle into the insecticide composition to obtain an aerosol.

Sample example.

Each of the insecticidal compositions obtained in Examples I to VII and Comparative Examples 1 to 4 was diluted with acetone to obtain a solution containing 0.189 g / l of compound A. 0.3 ml of a solution was applied to a 8.5 cm diameter petri dish so that compound A adhered to the petri dish in an amount of 0.0567 mg. That is, compound A was attached to the petri dish at a ratio of 10 mg / m2. After the Petri dish was dried by evaporation of acetone, 10 German cockroaches (Blattella germanicaΊ were released therein. The precipitate effect, KT50 (time needed to precipitate 50% of the cockroaches) was determined. Table B shows the results.

TABLE B

- conclusions -

Claims (9)

Insecticidal composition, characterized in that it contains: a) 2,4-dioxo-1- (2-propynyl) imidazolidin-3-ylmethyl-chrysanthemate, b) at least one carboxylic acid ester selected from the group of monocarboxylic acid esters containing 16 -19 carbon atoms and dicarboxylic acid ester with 16-19 carbon atoms, and optionally c) at least one inert carrier, wherein the weight ratio of (a) to (b) is from 3: 1 to 1: 100. 2. Insecticidal composition according to claim 1, characterized in that the carboxylic acid ester is selected from the group consisting of dibutyl phthalate, isopropyl palmitate, isopropyl myristate and hexyl laurate. Insecticide composition according to claim 2, characterized in that the carboxylic acid ester is dibutyl phthalate. Insecticide composition according to claim 2, characterized in that the carboxylic acid ester is isopropyl palmitate. Insecticide composition according to claim 2, characterized in that the carboxylic acid ester is isopropyl myristate. Insecticide composition according to claim 2, characterized in that the carboxylic acid ester is hexyl laurate. A method of controlling insects, characterized by administering to insects an insecticidal composition containing: a) 2,4-dioxo-1- (2-propynyl) imidazolidin-3-ylraethyl-chrysanthemate and b) at least one carboxylic acid ester selected from the group of monocarboxylic acid esters of 16-19 carbon atoms and dicarboxylic acid ester of 16-19 carbon atoms, the weight ratio of (a) to (b) being from 3: 1 to 1: 100. A method of preparing an insecticidal composition, characterized by mixing a) 2,4-dioxo-1- (2-propynyl) imidazolidin-3-ylmethyl-chrysanthemate and b) at least one carboxylic acid ester selected from the group of monocarboxylic acid esters with 16-19 carbon atoms and dicarboxylic acid ester with 16-19 carbon atoms, in a weight ratio of (a) to (b) from 3: 1 to 1: 100 under heating. A method of preparing an insecticidal aerosol, characterized by: applying an insecticidal composition containing: a) 2,4-dioxo-1- (2-propynyl) imidazolidin-3-ylmethyl-chrysanthemate and b) ten at least one carboxylic acid ester selected from the group of monocarboxylic acid esters of 16-19 carbon atoms and dicarboxylic acid ester of 16-19 carbon atoms, the weight ratio of (a) to (b) being from 3: 1 to 1: 100 in a container, applying a nozzle to the container, and forcing a propellant through the nozzle into the insecticide composition into the container.