FR2661070A1 - INSECTICIDE COMPOSITIONS BASED ON 2,4-DIOXO-1- (2-PROPYNYL) IMIDAZOLIDINE-3-YLMETHYL CHRYSANTHEMATE. - Google Patents

Abstract

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 consisting of 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 .

Description

The present invention relates to an insecticidal composition.

  2,4-dioxo-l- (2- chrysanthemate)

  propynyl) imidazolidine-3-ylmethyl of formula (hereinafter compound A)

0 O

3 t I 1

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

0 CH 3 CH 3

  is a compound described in US-A-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 it is

used alone.

  The present inventors have studied extensively how to enhance 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) & (b) is 3: 1 to 1: 100, the insecticidal activity of compound A is remarkably enhanced The present invention results

of this discovery.

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

  (a) 2,4-dioxo-1- (2-) chrysanthemum

  propynyl) imidazolidine-3-ylmethyl (compound A), (b) at least one compound 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 3: 1 to 1: 100, and optionally

(c) at least one inert support.

  Compound A comprises various optical and geometric isomers. Among the isomers, it is possible to incorporate into the insecticidal composition of the present invention an isomer exhibiting insecticidal activity and its mixtures. The content of compound A in the composition of the present invention is generally 0.001%. at 75%

in 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 phthalate, isopropyl palmitate, isopropyl myristate, hexyl laurate, etc. These compounds can also be used as a mixture One or more compounds chosen from among them are generally mixed in the composition of the present invention in an amount of 0.0003%

at 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:

  (l RS) -cis, trans-chrysanthemate from (RS) -3-allyl-2-

  methyl-4-oxocyclopent-2-enyl lallethrin;

  (l RS) -cis, trans-chrysanthemate of 3,4,5,6-tetrahydro-

  phthalimidomethyl Etetramethrin;

  (1 R) -cis, trans-chrysanthemate of (S) -2-methyl-4-oxo-

  3- (2-propynyl) cyclopent-2-enyl lprallethrin; (1 RS) -cis, 3-phenoxybenzyl phenothrinel transchrysanthemate;

  (1 RS) -cis, 5-benzyl-3- trans-chrysanthemate

furylmethyl lresmethrin;

  <l R) -cis, trans-chrysanthemate of t RS) -c-cyano-3-

phenoxybenzyl Ecyphenothrinel;

  (1 RS) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethyl-

  3-phenoxybenzyl cyclomanecarboxylate lpernmethrin;

  (i RS) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethyl-

  (RS) -c-cyano-3-phenoxybenzyl cyclopropanecarboxylate cypermethrin 3;

  (i R) -cis-3- (2,2-dibromovinyl) -2,2-dimethylcyclo-

  (S) - "- cycano-3-phenoxybenzyl ldeltamethrin prcpanecarboxylate;

  (1 RS) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethyl-

  (RS) -a-cyano-4-fluoro-3- cyclopropanecarboxylate

phenoxybenzyl Ccyfluthrinel;

  (IRS) -cis, 5- (2-propynyl) trans-chrysanthemate -

furfuryle Efuramethrin;

  2- (4-ethoxyphenyl) -2-methylpropyl and 3- oxide

  phenoxybenzyl Eéthofenproxl; 2,2-dichlorovinyl and dimethyl phosphate Edichlorvosl;

  O, O-dinmethyl phosphorothioate and O- (3-methyl-

  4-nitrophenyl Efenitrothionl; 2- (1-methylethoxy) phenyl methylcarbamate lpropoxurl;

  4-phenoxyphenyl oxide and (RS) -2- (2-

pyridyloxy) propyl lpyriproxyfenl;

  (2 E, 4 E> -ll-methoxy-3,7,11-trimethyl-2,4-dodeca-

  isopropyl dienate Emethoprenal; (2 E, 4 E) -3,7,11-trimethyldodeca-2,4-ethyl dienoate ú hydroprenel; 1- (4-chlorophenyl) -3- (2,6difluorobenzoyl) urea Ediflubenzuronl; and N-cyclopropyl-1,3,5-triazine-2,4,6-triamine E cyromazinel Specific examples of synergists are

  a-E 2- (2-butoxyethoxy) ethoxyl-4,5-methylenedioxy-2-

  propyltoluene (piperonyl butylate), I- (2-

  ethylhexyl) -bicyclol 2,2, 1 l hept-5-ene-2,3-dicarboximide (NGK-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 ester of the carboxylic acid 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. Culex spp Diptera such as (Culex pipiens pallens) and Culex tritaenforhynchus; Aedes spp like Aedes aegyptf; and Aedes albopictus; Anopheles spp like Anopheles sinensis (Chironomidae); Nuscidae like Musca domestica and Muscfna stabul ans; Calliphoridae; Sarcophagids; Fannia canicularis; Anthomyiidae such as Delia platura and Delia antiqua; Tephritids; Drosophila; Psychodids; Simul-ideas; Tabanids; Stomoxyids, etc. Dictyoptera Blattella germanica, Periplaneta fuliginosa, Periplaneta americana, Periplaneta brunnea, Blatta orientalis, etc. Formicidae hymenoptera, Vespidae, Bethvlidae, Tenthredinidae such as Athalfa rosae ruficornis, etc. Isoptera Reticulitermes speratus, Coptmdermes formosanus, etc. Ixodidae Boophilus microplus, etc. House dust mites Mites like Tyrophagus putrescentiae, Pyroalyphids like Dermatophagoides farinae, Cheyletids 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% 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 as

being limited to them.

  In the examples, the comparative examples and

  the test example, the parts are by weight.

Example 1

  50.0 parts of compound A (acid part: d-trans configuration) and 50.0 parts of isopropyl myristate are mixed by heating (approximately 40-50 ° C.)

  obtaining a liquid insecticide composition.

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

TABLE 1

Example

Example

  comparative Composition (parts by weight) Compound A Carboxylic acid ester

(acid part.

  configuration Iyristate Palmitate Laurate Phthalate Adipate Stearate Acetate d-trans) isopro isopro dibuty hexyl isyl butyl diiso pyle pyle propyl o O O O o o o o o o o o o o

O O O O O O O

O O O O 50 O O

O O O O O 50 O

O O O O O O 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. 0 parts of a propellant mixture of propane and

butane 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

  isopropyl alcohol and 28.0 parts 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 get an aerosol.

Example 10

  Dissolve 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 fixed 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 l

  1.0 part of compound A and 1.0 part of dibutyl phthalate 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. container spray nozzle Compressed into the insecticide composition via the nozzle 50.0 parts of a propellant mixture of propane, butane and ether

  dimethyl 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 Petri dish 8.5 cm in diameter so that an amount of 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 / m 2 After drying of the Petri dish by evaporation of

  acetone, we release 10 cockroaches (Blattella germanica).

  We determine the effect of stupefaction (KT 50, time

  necessary to stultify 50% of cockroaches).

Table 2 shows the results

TABLE 2

KT 50 (mn) for Blatella germanica

1 0.8

2 0 y 9 Example 3 1 O

4 0.9

1.1

6 0.9

7 1.2

Example 1 3.0 Comparative 2 2.8

3 4.1

4 3.3

Claims (9)

  1. Insecticidal composition which contains:   (a) 2,4-dioxo-1- chrysanthemate (2-   propynyl) imidazolidine-3-ylmethyl, (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 esters of dicarboxylic acids having from 16 to 19 carbon atoms, and optionally c) at least one inert support, the weight ratio of (a) & (b) being 3: 1 to 1: 100.   2. The insecticidal composition according to claim 1, in which the carboxylic acid ester is chosen from the group comprising dibutyl phthalate, isopropyl palmitate, isopropyl myristate and hexyl laurate.   3. Insecticidal composition according to claim 1, in which the carboxylic acid ester is dibutyl phthalate.   4 Insecticidal composition according to claim 1, wherein the carboxylic acid ester is isopropyl palmitate.   5. Insecticidal composition according to claim 1, in which the carboxylic acid ester is isopropyl myristate.   6. An insecticidal composition according to claim 1, in which the carboxylic acid ester is hexyl laurate.   7. Method for combating insects, which consists in: applying to the insects an insecticidal composition comprising: (a) 2,4-dioxo-1- (2-propynyl) imidazolidine-3-ylmethyl chrysanthemate and (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 esters of dicarboxylic acids having from 16 to 19 carbon atoms, the weight ratio of (a) to (b) being 3: 1 to 1: 100.   8. Process for the preparation of an insecticide composition which consists in: mixing under heating   (a) 2,4-dioxo-1- chrysanthemate (2-   propynyl) imidazolidine-3-ylmethyl 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.   9 Process for preparing an insecticidal aerosol, which consists in: introducing an insecticidal composition comprising:   (a) 2,4-dioxo-1- chrysanthemate (2-   propynyl) imidazolidine-3-ylmethyl 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) of 3: 1 to 1: 100 loo, in a container, to mount a spray nozzle on the container, and to compress a propellant through the nozzle in the   insecticide composition contained in the container.