SI9110736A - Insecticidal compositions - Google Patents

Abstract

The insecticidal composition of the present invention comprises (a) 2,4-dioxo-1- (2-propynyl) -imidazolidin-3-ylmethyl chrysanthemum! and (b) at least one carboxylic acid ester, which is selected from the group consisting of monocarboxyl esters acids having 16-29 carbon atoms and esters dicarboxylic acids having from 16 to 19 atoms carbon having a weight ratio of (a) to (b) from 3: 1 to 1: 100.

Description

INSECTICIDES

COMPOSITIONS

The subject of the present invention is an insecticidal composition.

2,4-dioxo-1- (2-propynyl) imidazoidin-3-ylmethyl chrysanthemum of the formula (hereinafter mixture A)

0

Λ And!

CH = CCH ₂ N NCH ₂ OC - \ - · - -CH = C (CH ₃ ) ₂

M, o CH ₃ ch ₃ is a compound found in USP 4,176.189 known to be useful as an active ingredient of insecticides, but the mixture does not show satisfactorily high insecticidal activity when used alone.

The present inventors have extensively studied how to increase the insecticidal activity of mixture A, and as a result have found that when (a) mixture A is added (b) at least one carboxylic acid ester selected from the group consisting of monocarboxylic acid esters having 16 to 19 carbon atoms, and dicarboxylic acid esters having 16 to 19 carbon atoms such that the mass ratio (a) to (b) is from 3: 1 to 1: 100, the insecticidal activity of mixture A is greatly increased. The present inventors have thus come to the present invention.

The present invention provides an insecticidal mixture comprising (a) 2,4-dioxo-1- (2-propynyl) imidazolidin-3i having 1 chrysanthemum (mixture A), (b) at least one ingredient selected from the group consisting of monocarboxyl esters acids having 16-19 carbon atoms and dicarboxylic acid esters having 16-19 carbon atoms and a weight ratio (a) to (b) of 3: 1 to 1: 100, and optional (c) at least one an inert carrier.

Mixture A contains various optical and geometric isomers. Of these isomers, any isomer that exhibits insecticidal activity and mixtures thereof may be incorporated into the insecticidal composition of the present invention. The content of mixture A in the composition of the present invention is typically 0.001 to 75 parts by weight.

Specific examples of monocarboxylic acid esters having 16 to 19 carbon atoms and dicarboxylic acid esters having 16 to 19 carbon atoms are dibutyl phthalate, isopropynyl palmitate, isopropyl myristate, hexyl laurate, etc. These mixtures can also be used as admixtures. One or more of the mixtures selected from these mixtures are typically blended into the composition of the present invention in an amount of 0.0003 to 75 weight percent.

One or more other insecticides, synergetics, fragrances, fungicides, solvents, propellants, solid carriers, etc., may be included in the composition of the present invention.

Specific examples of other insecticides are:

(RS) -3-α1,11-methyl-4-oxocyclopent-2-ene1 (1RS) -c and s, trans-chrysanthemum (alethrin);

3,4,5,6-tetrahydrophthalimidomethyl (1RS) -cis, transcryanthemate (tetramethrin);

(S) -2-methyl-4-oxo-3- (2-propynyl) ccyclopent-2-ene1 (IR) cis, trans-chrysanthemum (pralethrin);

3-phenoxybenzyl (1RS) -cis, trans-chrysanthemum (phenothrin);

5-Benzi1-3-furie Have 1 (IRS) -cis, trans-chrysanthemum (resmethrin);

(RS) -a-cyano-3-phenoxybenzyl (1RS) -cis, transcryanthemate (cyphenothrin);

3-phenoxybenzyl (1RS) -cis, trans-3- (2,2-dichlorovinyl) 2,2-dimethylcyclopropanecarboxylate (permethrin); (RS) -α-cyano-3-phenoxybenzyl (1RS) -cis, trans-3- (2,2dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate (cypermethrin);

(S) -α-cyano-3-phenoxybenzyl (1R) -cis-3- (2,2dibromovinyl) -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) furufuryl (1RS) -cis, trans-chrysanthemum (furamethrin);

2- (4-ethoxyphenyl) -2-methylpropyl 3-phenoxybenzyl ether (ethofenprox);

2.2-dichlorovinyl dimethyl phosphate (dichlorvos);

O, 0-dimethyl O- <3-methyl-4-nitrophenyl) -phosphorothioate (phenitrothion);

2- (1-methoxy) phenyl methylcarbamate (propoxur);

4- phenoxyphenyl (RS) -2- (2-pyridyloxy) propyl ether (pyriproxyfen);

isopropyl (2E, 4E) -11-methoxy-3,7,11-trimethyl-1,2,4-dodecadienoate (methoprene);

ethyl (2E, 4E) -3,7,11-trimethyldodeca-2,4-dienoate (hydroprene);

1- (4-chlorophenes 1) -3- (2,6-di fluorobenzoyl) urea (diflubenzuron) and

N-cyclopropyl-1,3,5-triazine-2,4,6-triamine (cyromazine).

Specific examples of synergetics include α- / 2- (2-butoxyethoxy) ethoxy and N-4,5-methylenedi oxo-2-propylthiouene (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 solvents are isopropyl alcohol, kerosene, dodecylbenzene, etc.

Specific examples of propellants are propane / butane, dimethyl ether, freon '*' ** gas (fluorocarbons), etc.

The composition of the present invention is prepared e.g. by mixing the required amount of mixture A and the prescribed amount of at least one of the carboxylic acid ester described above and, if necessary, other insecticides, synergists, fragrances, fungicides, solvents, propellants, solid carriers, etc. at room temperature or by heating.

The insects and mites affected by the mixture thus prepared according to the present invention are the following:

Lepidoptera (husk wings) fur moth (Tinea pellionella), cloth or house moth (Tineola bisselliella), etc.

Diptera (double-winged) mosquito genus (Culex) such as e.g. common mosquito (Culex_pipiens_pallens) and Culex tritaeniorhynchus; the genus Aedes as e.g. Aedes aegypti; and Aedes albopictus; the genus Anopheles as e.g. Anopheles sinensis (Chironomidae); real flies (Muscidae) such as a house fly (Musca domestica) and a squirrel house fly (Mus c i on staff1ans); Calliphoridae; Sarcophagidae; small house fly (Fannia canicularis); flower flies (Anthomyi idae) like e.g. wheat seed fly (Delia platura) and onion fly (Delia antigua); fruit flies (Tephritidae); Drosophilidae; moth flies (Psychodidae); pigeon flies (Simuliidae); Tabanidae; barn flies (Stomoxydae), etc.

Dictyoptera Schwab (Blattella germanica), Chad cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), Brown cockroach (Periplaneta brunnea), Kitchen cockroach (Blatta orientalis), etc.

Hymenoptera (skins) of ants (Formicidae), true wasps (Vespidae), Bethylidae, leaflets (Tenthredinidae), such as. green fly (Athalia rosae ruficornis), etc.

Isoptera (termites)

Reticulitermes speratus, Coptotermes formosanus, etc.

Ixodidae

Boophilus microplus, etc.

Dust mites

Acaridae as e.g. Tyrophagus putrescentiae, Pyroalyphidae as e.g. Dermatophagoides farinae, Cheyletidae as e.g. Che1acarops i s moore i, Macronyssidae as nrp. Ornithonyssus bacoti, etc.

The composition of the present invention may be used as it is for destroying an insect; however, it is commonly used formulated in the form of a preparation such as aerosols, oil sprays, etc. In the latter case, the content of mixture A in aerosols or in oil sprays is preferably 0.001 to 5 parts by weight.

The present invention is illustrated in more detail with the following examples, primary examples and test cases; however, the present invention should not be construed as limited to these.

In the cases, comparative cases and test cases, the proportions by weight are given.

Example 1

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

Table 1 lists the insecticidal mixtures obtained in the same manner as the above.

rH

Table

ethyl acetate Oh 0 ο Ο Ο Ο Ο Ο 0 ο 0 ΙΑ -P (you H p • H (you 4> φ Pl 43/3 n Oh 0 Ο Ο ο Ο ο Ο 0 ο ΙΑ ο no 1 H 4 »O * rl (ti N P. P. τ | O Ή • H p «d T) P <(you 0 0 Ο 0 ο Ο ο Ο 0 ΙΑ ο ο share) lne sour dibutyl phthalate 0 0 Ο 0 ο Ο ο ΙΑ Ο Ο ο ο Composition (oily • H n Λί o s «J M hexyl lavrat Oh 0 ο 0 ο R Ο Ο Ο ο ο P Oh 43 K w l Λ O (you p4 +> OH 43 t4 · Η · Η • h p, a Oh 0 ο Ο R Ο ο Ο Ο ο ο isopropyl myristate σ ' 0 σ \ s 0 rA Ο ο ο Ο Ο ο ο Mixture A (acid fraction: d-trans configuration) rH ο r-1 R Ο Α- ο ΙΑ ο ΙΑ ο ιΑ 100 & £ ο ΙΑ γΗ CU m ΙΑ Φ Α- r-l οι fA st Example Comparative example

Example β

0.1 parts of mixture A, 0.1 parts of isopropyl myristate and 0.3 parts of cyphenothrin were dissolved in a mixture of 20.0 parts of dodecylbenzene and 39.5 parts of kerosene. With the resulting mixture, we filled the container. We mounted a nozzle on the container. 40.0 parts of propane / butane mixture as propellant were pressurized through a nozzle into an insecticide mixture to obtain an aerosol.

Example 9

1.0 part of mixture A and 1.0 part of isopropyl myristate were dissolved in a mixture of 20.0 parts of isopropyl alcohol and 28.0 parts of kerosene. With the resulting mixture, we filled the container. We mounted a nozzle on the container. 50.0 parts of a mixture of propane, butane and dimethyl ether as propellant were pressurized through a nozzle into an insecticide mixture to obtain an aerosol.

Example 10

1.0 parts of mixture A and 31.0 parts of isopropyl myristate were dissolved in 18.0 parts of kerosene. With the resulting mixture, we filled the container. We mounted a nozzle on the container. 50.0 parts of a mixture of propane, butane and dimethyl ether as propellant were pressurized through a nozzle into an insecticide mixture to obtain an aerosol.

Example 11

1.0 part of mixture A and 1.0 part of dibutyl phthalate were dissolved in a mixture of 2.5 parts of isopropyl alcohol and

45.5 parts of dodecylbenzene. With the resulting mixture, we filled the container. We mounted a nozzle on the container. 50.0 parts of a mixture of propane, butane and dimethyl ether as propellant were pressurized through a nozzle into an insecticide mixture to obtain an aerosol.

Test case

Each of the insecticidal mixtures obtained in Examples 1 to 7 and Comparative Examples 1 to 4 was diluted with acetone to give a solution containing 0.189 g / l of mixture A. With a 0.3 ml solution, a 8.5 cm diameter evaporator was coated. so that 0.0567 mg of mixture A. was applied to the evaporator, i.e., mixture A was applied to the evaporator at a ratio of 10 mg / m ² . After evaporation of the acetone evaporator, 10 Blubs (Blattella germanica) were dropped. We determined the lethal dose of LDgQ (time required to kill 50 percent of cockroaches). The results are listed in Tables 1 and 2.

Table 2

LDc ₀ (min) ² at Swabs 1 0.8 2 0.9 Example 3 1.0 4 0.9 5 1.1 6 0.9 7 1,2 1 3.0 Comparative 2 2.8 example 3 4,1 4 3.5

For Summit Chemical Co., Ltd.:

Claims (9)

Patent claims 1. An insecticidal composition comprising: (a) 2,4-dioxo-1- (2-propynyl) imidazolidin-3yl having 1 chrysanthemum, (b) at least one carboxylic acid ester selected from the group consisting of monocarboxylic acid esters having from 16 to 19 carbon atoms and dicarboxylic acid esters having from 1619 carbon atoms and optionally (c) at least one inert carrier, and having a weight ratio (a) to (b) of from 3: 1 to 1: 100. An 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. An insecticidal composition according to claim 1, characterized in that the carboxylic acid ester is dibutyl phthalate. An insecticidal composition according to claim 1, characterized in that the carboxylic acid ester is isopropyl pyrimidate. An insecticidal composition according to claim 1, characterized in that the carboxylic acid ester is isopropyl myristate. An insecticidal composition according to claim 1, characterized in that the carboxylic acid ester is hexyl laurate. 7. An insect control method comprising: an insecticide insecticide application comprising: (a) 2,4-dioxo-1- (2-propynyl) imidazolidin-3-ylmethyl 1 chrysanthemum and (b) at least one carboxylic acid ester selected from the group consisting of monocarboxylic acid esters having from 16- 19 carbon atoms and dicarboxylic acid esters having from 16-19 carbon atoms, wherein the weight ratio (a) to (b) is 3: 1 to 1: 100. 8. A process for the production of an insecticidal composition comprising mixing (a) 2,4-dioxo-1- (2-propynyl) imidazolidin-3Imethyl 1 chrysanthemum and (b) at least one carboxylic acid ester selected from the group consisting of it is formed by monocarboxylic acid esters having from 16-19 carbon atoms and dicarboxylic acid esters having from 16-19 carbon atoms by weight (a) to (b) from 3: 1 to 1: 100 by heating. 9. A process for the production of an insecticidal aerosol, characterized in that it comprises: filling the container with an insecticide mixture comprising: (a) 2,4-dioxo-1- (2-propynyl) imidazolidin-3yl having 1 chrysanthemum; and (b) at least one carboxylic acid ester selected from the group consisting of monocarboxylic acid esters having from 16-19 carbon atoms and dicarboxylic acid esters having from 16 to 19 carbon atoms, the weight ratio of (a) to (b) being 3: 1 to 1: 100, in order to provide said container with a spray tube and to pass through it the tube injects reactive fuel into said insecticide mixture under pressure.