CH682706A5 - Insecticidal compositions based chrysanthemate 2,4-dioxo-1- (2-propynyl) imidazolidin-3-ylmethyl. - Google Patents

Description

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CH 682 706 A5

Description

The present invention relates to an insecticidal composition.

2,4-dioxo-1- (2-propynyl) imidazolidine-3-methyl chrysanthemate of formula (hereinafter composed

AT)

JL

CH = CCH2N NCH2OC ^ 77 CH = C (CH3) 2

\ ch3 ch3

is a compound described in US Pat. No. 4,176,189 and it is known that it can be used as an active ingredient for insecticides. However, the compound does not exhibit sufficiently high insecticidal activity when used alone.

The present inventors have studied extensively the way of reinforcing the insecticidal activity of compound A and have consequently found that, when (b) at least one ester of carboxylic acid chosen from the group comprising esters of monocarboxylic acids having from 16 to 19 carbon atoms and the esters of dicarboxylic acids having from 16 to 19 carbon atoms is added (a) to compound A so that the weight ratio of (a) to (b) is 3: 1 to 1: 100, the insecticidal activity of compound A is remarkably enhanced. The present invention results from this discovery.

According to the present invention, there is provided an insecticidal composition comprising:

(a) 2,4-dioxo-1- (2-propynyl) imidazolidine-3-ylméthyIe chrysanthemate (compound A),

(b) at least one compound chosen from the group comprising the esters of monocarboxylic acids having from 16 to 19 carbon atoms and the esters of dicarboxylic acids having from 16 to 19 carbon atoms, the weight ratio of (a) to (b) being from 3: 1 to 1: 100, and optionally

(c) at least one inert support.

Compound A includes various optical and geometric isomers. Among the isomers, there may be incorporated into the insecticidal composition of the present invention an isomer having insecticidal activity and mixtures thereof. The content of compound A in the composition of the present invention is generally from 0.001% to 75% by weight.

Particular examples of the esters of monocarboxylic acids having from 16 to 19 carbon atoms and the esters of dicarboxylic acids having from 16 to 19 carbon atoms are dibutyl phtaiate, isopropyl palmitate, isopropyl myristate, hexyl laurate, etc. These compounds can also be used as a mixture. One or more compounds chosen from them are generally mixed in the composition of the present invention in an amount of 0.0003% to 75% by weight.

In the composition of the present invention, one or more other insecticides, synergists, perfumes, fungicides, solvents, propellants, solid carriers, etc. can be incorporated.

Particular examples of other insecticides are:

(1 RS) -cis, (RS) -3-allyl-2-methyl-4-oxocyclopent-2-enyl [allethrin] trans-chrysanthemate;

(1 RS) -cis, 3,4,5,6-tetrahydro-phthalimidomethyl [tetramethrin] trans-chrysanthemate;

(1 R) -cis, (S) -2-methyl-4-oxo-3- (2-propynyl) cyclopent-2-enyl trans-chrysanthemate [prallethrin];

(1 RS) -cis, 3-phenoxybenzyl trans-chrysanthemate [phenothrin];

(1 RS) -cis, 5-benzyl-3-furylmethyl trans-chrysanthemate [resmethrin];

(1 R) -cis, trans-chrysanthemate of (RS) -a-cyano-3-phenoxybenzyIe [cyphenothrin];

(1 RS) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate of 3-phenoxybenzyl [per-methrin];

(1 RS) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethyl-cyclopropanecarboxylate of (RS) -a-cyano-3-phe-noxybenzyl [cypermethrin];

(1R) -cis-3- (2,2-dibromovinyl) -2,2-dimethylcyclo-propanecarboxylate of (S) -a-cyano-3-phenoxybenzyl [deltamethrin];

(1 RS) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethyl-cyclopropanecarboxylate from (RS) -a-cyano-4-fluoro-3-phenoxybenzyl [cyfluthrin];

(1 RS) -cis, 5- (2-propynyl) -furfuryle [furamethrin] trans-chrysanthemate;

2- (4-ethoxyphenyl) -2-methylpropyl and 3-phenoxybenzyl oxide [ethofenprox];

2,2-dichlorovinyl dimethyl phosphate [dichlorvos];

0.0- dimethyl and 0- (3-methyl-4-nitrophenyl [fenitrothion] phosphorothioate;

2- (1-methylethoxy) phenyl methylcarbamate [propoxur];

4-phenoxyphenyl oxide and (RS) -2- (2-pyridyloxy) propyl oxide [pyriproxyfen];

(2E, 4E) -11-methoxy-3,7,11-trimethyl-2,4-isopropyl [methoprene] -dodecadienate;

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CH 682 706 A5

(2E, 4E) -3,7,11-trimethyldodeca-2,4-ethyl dienoate [hydroprene]; 1 - (4-chlorophenyl) -3- (2,6-difluorobenzoyl) urea [diflubenzuron]; and N-cyclopropyl-1,3,5-triazine-2,4,6-triamine [cyromazine].

Particular examples of synergists are a- [2- (2-butoxyethoxy) ethoxy] -4,5-methylene-dioxy-2-propyltoluene (piperonyl butylate), N- (2-ethylhexyl) -bicyclo [2,2,1] hept-5-ene-2,3-dicarboximide (MGK-264), octachlorodipropyl ether (S-421), etc.

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

Particular examples of the propellants are propane / butane, dimethyl ether, Freon® gases (fluorinated hydrocarbons), etc.

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

The insects and mites against which the composition of the present invention thus prepared is effective are indicated below:

Lepidoptera

Tinea pellionella, Tineola bisselliella, etc.

Diptera

Culex spp. such as (Culex pipiens pallens) and Culex tritaeniorhynchus; Aedes spp. like Aedes aegypti; and Aedes albopictus; Anopheies spp. such as Anopheles sinensis (Chironomidae); Muscids such as Musca domestica and Muscina stabulans;

Calliphoridae; Sarcophagids; Fannia canicularis; Anthomyiidae such as Delia platura and Delia antiqua; Tephritids; Drosophila; Psychodids; Simuliids; Tabanids; Stomoxyids, etc.

Dictyopters

Blattella germanica, Periplaneta fuliginosa, Periplaneta americana, Periplaneta brunnea, Blatta orien-talis, etc.

Hymenoptera

Formicidae, Vespidae, Bethylidae, Tenthredinidae such as Athalia rosae ruficornis, etc.

Isopters

Reticulitermes speratus, Coptodermes formosanus, etc.

Ixodidae

Boophilus microplus, etc.

Household dust mites

Mites like Tyrophagus putrescentiae, Pyroalyphids like Dermatophagoides farinae, Chey-letidae like Chelacaropsis moorei, Macronyssidae like Ornithonyssus bacoti, etc.

The composition of the present invention can be used as such to destroy pests; however, it is often used in the form of a preparation such as aerosols, oily sprays, etc. In the latter case, the content of compound A in aerosols or oily sprays is preferably from 0.001% to 5% by weight.

The present invention is illustrated in more detail with reference to the following examples, comparative examples and the test example; however, the present invention should not be considered to be limited thereto.

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

Example 1

When heated (about 40-50 ° C), 50.0 parts of compound A (acid part: d-trans configuration) and 50.0 parts of isopropyl myristate are mixed to obtain a liquid insecticidal composition.

Table 1 lists the insecticide compositions obtained in the same manner as above.

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CH 682 706 A5

TABLE 1

Composition (parts by weight)

Compound A Carboxyic acid ester

(acid part. ^ ristate palmitate Laurate Phtaiate Stearate adipate Acetate con igura ion ^ 'isopro- of isopro- of ethyl butyl dibu- diisopro- to "Trans pyle pyle tyle pyle

Example

1

1

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50

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0

0

0

0

0

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4

70

30

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0

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0

0

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5

50

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50

0

0

0

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0

6

50

0

0

50

0

0

0

0

7

50

0

0

0

50

0

0

0

Example

1

100

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0

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0

0

0

0

comparative

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50

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50

0

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3

50

0

0

0

0

0

50

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4

50

0

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0

0

0

0

50

Example 8

0.1 part of compound A, 0.1 part of isopropyl myristate and 0.3 part of cyphenothrin are dissolved in a mixture of 20.0 parts of dodecylbenzene and 39.5 parts of kerosene. The resulting mixture is introduced into a container. A spray nozzle is provided on the container. 40.0 parts of a propane and butane propellant mixture are compressed in the insecticide composition via the nozzle to obtain an aerosol.

Example 9

1.0 part of compound A and 1.0 part of isopropyl myristate are dissolved in a mixture of 20.0 parts of isopropyl alcohol and 28.0 parts of kerosene. The resulting mixture is introduced into a container. A spray nozzle is provided on the container. The insecticide composition is compressed via the nozzle 50.0 parts of a propellant mixture of propane, butane and dimethyl ether to obtain an aerosol.

Example 10

Is dissolved in 18.0 parts of kerosene 1.0 part of compound A and 31.0 parts of isopropyl myristate. The resulting mixture is introduced into a container. A spray nozzle is attached to the container. The insecticide composition is compressed via the nozzle 50.0 parts of a propellant mixture of propane, butane and dimethyl ether to obtain an aerosol.

Example 11

1.0 part of compound A and 1.0 part of dibutyl phtaiate are dissolved in a mixture of 2.5 parts of isopropyl alcohol and 45.5 parts of dodecylbenzene. The resulting mixture is introduced into a container. A spray nozzle is provided on the container. The insecticide composition is compressed via the nozzle 50.0 parts of a propellant mixture of propane, butane and dimethyl ether to obtain an aerosol.

Test example

Each of the insecticidal compositions obtained in Examples 1 to 7 and Comparative Examples 1 to 4 is diluted with acetone to obtain a solution containing 0.189 g / l of compound A. 0.3 ml of the solution is deposited in a box 8.5 cm diameter petri dish such that 0.0567 mg of compound A is attached to the petri dish. Therefore, compound A is attached to the petri dish at a rate of 10 mg / m2. After drying the Petri dish by evaporation of the acetone,

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CH 682 706 A5

10 cockroaches (Blattella germanica) are released there. The dulling effect is determined (KT50, time required to dumb 50% of cockroaches).

Table 2 shows the results

TABLE 2

Example

Comparative example

KT50 (mn) for Blattella germanica

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1.1

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3.0

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2.8

3

4.1

4

3.3

Claims (10)

Claims 1. Insecticidal composition which contains: (a) 2,4-dioxo-1- (2-propynyl) imidazolidine-3-ylmethy! e chrysanthemate, and (b) at least one carboxylic acid ester chosen from the group comprising esters of monocarboxylic acids having from 16 to 19 carbon atoms and esters of dicarboxylic acids having from 16 to 19 carbon atoms, the weight ratio of (a) to (b) being from 3: 1 to 1: 100. 2. Insecticidal composition according to claim 1, in which the carboxylic acid ester is chosen from the group comprising dibutyl phtaiate, isopropyl palmitate, isopropyl myristate and hexyl laurate. 3. The insecticidal composition according to claim 1, wherein the carboxylic acid ester is dibutyl phtaiate. 4. The insecticidal composition according to claim 1, wherein the carboxylic acid ester is isopropyl palmitate. 5. An insecticidal composition according to claim 1, wherein the carboxylic acid ester is isopropyl myristate. 6. An insecticidal composition according to claim 1, wherein the carboxylic acid ester is hexyl laurate. 7. Insecticidal composition according to one of claims 1 to 6, characterized in that it also contains at least one inert support. 8. Method for combating insects, which consists in: applying to the insects an insecticidal composition comprising: (a) 2,4-dioxo-1- (2-propynyl) imidazolidine-3-ylmethy! e chrysanthemate and (b) at least one carboxylic acid ester chosen from the group comprising esters of monocarboxylic acids having from 16 to 19 carbon atoms and esters of dicarboxylic acids having from 16 to 19 carbon atoms, the weight ratio of (a) to (b) being from 3: 1 to 1: 100. 9. Process for the preparation of an insecticide composition which consists in: mixing under heating (a) 2,4-dioxo-1- (2-propynyl) imidazolidine-3-ylmethyl chrysanthemate and (b) at least one carboxylic ester chosen from the group comprising esters of monocarboxylic acids having from 16 to 19 carbon atoms and esters of dicarboxylic acids having from 16 to 19 carbon atoms, in a weight ratio of (a ) to (b) from 3: 1 to 1: 100. 10. Process for the preparation of an insecticidal aerosol, which consists in: introducing an insecticidal composition comprising: (a) 2,4-dioxo-1- (2-propynyl) imidazolidine-3-ylmethyl chrysanthemate and (b) at least one carboxylic ester chosen from the group comprising esters of monocarboxylic acids having from 16 to 19 carbon atoms and esters of dicarboxylic acids having from 16 to 19 carbon atoms, with a weight ratio of (a ) to (b) from 3: 1 to 1: 100, in a container, mounting a spray nozzle on the container, and compressing a propellant through the nozzle into the insecticide composition contained in the container. 5