GB2243297A

GB2243297A - Insecticidal compositions

Info

Publication number: GB2243297A
Application number: GB9107920A
Authority: GB
Inventors: Hazunobu Dohara; Mitsuyasa Makita; Yasuo Abe
Original assignee: Sumitomo Chemical Co Ltd
Current assignee: Sumitomo Chemical Co Ltd
Priority date: 1990-04-24
Filing date: 1991-04-15
Publication date: 1991-10-30
Anticipated expiration: 2011-04-15
Also published as: GB2243297B; HU209631B; DE4113383A1; IT1244979B; CH682706A5; GB9107920D0; ITRM910273A0; JPH0764687B2; DE4113383C2; FR2661070A1; AU7420191A; AU636471B2; FR2661070B1; JPH049306A; BE1004726A3; SG156894G; ITRM910273A1; NL9100673A

Abstract

An insecticidal composition comprises (a) 2, 4-dioxo-1-(2-propynyl)-imidazolidin-3-ylmethyl chrysanthemate and (b) at least one mono- or di-carboxylic acid ester having 16 to 19 carbon atoms, the weight ratio of (a) to (b) being from 3:1 to 1:100. The ester strengthens the activity of (a).

Description

1 11 1 INSECTICIDAL COMPOSITIONS 1 "'he present invention relates to an

insecticidal composition.

1 .,4-Dioxo-l-(2-propynyl)imidazolidin-3- ylmethyl chrysanthemate having the formula (hereinafter Compound A.), 0 0 JL C, CCH2N 12W 0 CH3 CH3 C11:C (CR3) 2 is a compound disclosed in US-A-4176189, and is known to be useftil-as an active ingredient for insecticides.

ie compound does not exhibit a satisfactorily However,. t4 high insecticidal activity when used alone.

Tle have made extensive studies in an attempt.

to strengthen the insecticidal activity of Compound A, and as a r,sult have found that when (b) at.'lea;t one carp, oxylic acid ester-selected from ..-t.-c, -- moxfocarboxylic acid esters having 16 to 19 carbon ti IX li_15 zCtoms.,d dicarboxylic acid esters having 16 to 19 1;. '- -- I- r caxbori.-e.'to,;t.s is added to (a) Compound A so that the weiglitlrat..-o of (a) to (b) is from 3:1 to 1:100, the insecticidal activity of Compound A is remarkably ."..,..itrengthentd.

2 t,.ccording to the present invention, there is provided an insecticidal composition comprising:

(a) 2,4-dioxo-l-(2-propynyl)imidazolidin-3- ylmethyl chrysanthemate (Compound A), (b) at least one member selected from monocarboxylic acid esters having 16 to 19 carbon atoms and dicarboxylic acid esters having 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 carrier.

Compound A includes various optical and geometrical isomers. Of the isomers, an isomer exhibiting an insecticidal activity and the mixtures be incorporated in the insecticidal thereof caid composition of the present invention. The content of Compound P. in the composition of the present invention is usually 0.001% to 75% by weight.

-Specific examples of the monocarboxylic acid esters having 16 to 19 carbon atoms and the dicarboxylic acid ester's having 16 to 19 carbon atoms are dibutyl phthalate, isopropyl palmitate, isopropyl myristate and hexyl laurate. 'These compounds may also be used in admj.x,t;ure thereof. One or more compounds selected from these compounds are usually blended in the compo sition of the present invention in an amount of 0.0003% to 75% by weight.

Into the composition of the present invention may be incorporated one or more of other insecticides, j 1 t 11 1 synergists, perfumes, fungicides, solvents, propellants, solid carriers, etc.

Specific examples of the other insecticides are:

RS)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (lRS)-cis,::ranschrysanthemate [allethrin]; 4,5,6-tetrahydrophthalimidomethy1 (lRS)cis,trans-chrysanthemate [tetramethrin]; (S)-2-methyl-4-oxo-3-(2-propynyl)cyclopent-210 enyl (lR)-cis,transchrysanthemate [prallethrin); 3-phenoxybenzyl (lRS)-cis,trans-chrysanthemate [phenothrin]; 5-benzyl-3-furylmethyl (lRS)-cis,transchrysanthemate (resmethrin];.

is (RS)-a-cyano-3-phenoxybenzyl (1R)-cis,trans- chrysanthemate [cyphenothrin]; 3-phenoxybenzyl (1RS)-cis,trans-3-(2,2dichloroviny.li.)-2r2dimethylcyclopropanecaboxylate [permethrin]; 20 (BS)-a-cyano-3-phenoxybenzyl (1RS) cis,trans3-(2,2dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate [cypermethrinj; (S)-acyano-3-phenoxybenzyl (1R)-cis-3-(2,2dibromovinyl)-2,2dimethylcyclopropanecarboxylate [deltamethrin]; (RS)-a-cyano-4-fluoro-3phenoxybenzyl (1RS)cis,trans 3-(2y2-dichlorovinyl)-2,2dimethylcyclopropanecarboxylate [cyfluthrinj; 11 1 is 4 - 1 5-(2-proiDynyl)furufuryl (1RS)-cis,trans chrysanthemate [furamethrin]; 2-(4-ethoxyphenyl)-2-methylpropyl 3 phenoxyberizyl ether [ethofenprox); 2,2-dichlorovinyl dimethyl phosphate dichlorvc:.-, 1; 3,0-dimethyl 0-(3-methyl-4-nitrophenyl) phosphorothioate Ifenitrothion]; 2-(l-methyethoxy)phenyl methylcarbamate [propoxuri; 4-phenoxyphenyl (RS)-2-(2-pyridyloxy)propyl ether [pyriproxyfen]; isopropyl (2E,4E)-11-methoxy-3,7,11-trimethyl2,4-dodecadienoate [methoprenel; ethyl (2E,4E)-3r7,11-trimethyldodeca-2,4dienoate [hydroprenel; 1-(4-chloraphenyl)-3-(2,6-difluorobenzoyl)urea Idiflubenzuron]; and N-cyclopropyl-l,3r5-triazine-2,4,6-triamine 20 [cyromazine].

Specific examples of the synergists are a-[2(2-butoxyethoxy)ethoky]-4r5methylenedioxy-2propyltoluene (piperonyl butoxide), N-(2ethylhexyl)bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide (MGK-264)t 25 octachlorodipropyl ether (S-421), etc.

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

1 - Specific examples of the propellants are propane/butane, dimethyl ether, FreonTM gas (fluorocarbons), 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.

Insects and acarina against which compositions of the present invention thus prepared are effective are listed below: Lepidoptera casemaking clothes moth (Tinea pellionella), webbing clothes moth (Tineola bisselliella), etc.

Diptera 1 25 1 Culex spp. such as common mosquito (Culex Ripiens pallens) and Culex tritaeniorhynchus; Aedes spp. such as Aedes aeqypti; and Aedes albopictus, ,.AnoDheles spp. such as Anopheles sinensis midges (Chironomidae); Muscidae such as housefly (Musca domestica) and false stablefly (Muscina stabulans); Calliphoridae; Sarcophagidae; little housefly (Fannia canicularis); - 6 1 Anthom.yiidae such as seedcorn maggot (Delia platura) and onion'maggot (Delia anticrua); fruit flies (Tephritidae); Drosophilidae; moth flies (Psychodidae); black flies (Simuliidae); Tabanidae; stable flies (Stomoxyidae) etc.

Dictyoptera German cockroach (Blattella qermanica), c.mokybrown cockroach (Periplaneta fuliqinosa), American cockroach (Periplaneta americana), brown cockroach (Periplaneta brunnea), oriental cockroach (Blatta orientalis), etc.

Hymenoptera ants (Formicidae), hornets (Vespidae), Bethylidae, sawflies (Tenthredinidae) such as cabbage sawfly (Athalia rosae ruficornis), etc.

Isoptera Ixodidae Reticulitermes speratus, Coptotermes formosanus etc.

Boophilus microplust etc.

House dust mites h i Acaridae such as Tyrophaqus putrescentiae, Pyroalyphidae such as Dermatophagoides farinae, Cheyletidae such as Chelacaropsis moorei, Macronyssidae such as Ornithonyssus bacotir et 1 c 7 i 1 The composition of the present invention can be used as it is for killing the insect pests; however, it is usually used formulated into the form of preparatior, such as aerosols, oil sprays, etc. In the latter case, the content of Compound A in the aerosols or in the:kil sprays is preferably 0.001% to 5% by weight.

The present invention is illustrated in more detail with reference to the following Examples, Comparative Examples and Test Example; however, the present invention should not be interpreted as being limited thereto.

In Examples, Comparative Examples and Test Example, parts are by weight.

Example 1

50.0 Parts of Compound A (acid moiety: d trans configuration) and 50.0 parts of isopropyl myristate were mixed under heating (about 40 to 500C) to obtain a liquid insecticidal composition.

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

j 1 Table 1

Composition (part by weight) Compound A Carboxylic acid ester (acid moiety: ISO- ISO- Hexyl Dibutyl Diiso-. 13tity', EP h v d-trans configurapropyl propyl laurate phtha- propyl stearate acetate tion) myris- palmilate adipate tate tate 1 1 99 0 0 0 0 0 0 2 10 90 0 0 0 0 0 0 3 50 50 0 0 0 0 0 0 Example 4 70 30 0 0 0 0 0 0 50 0 50 0 0 0 0 0 6 50 0 0 50 0 0 0 0 7 50 0 0 0 50 0 0 0 1 100 0 0 0 0 0 0 0 Comparative 2 50 0 0 0 0 50 0 0 Example 3 50 0 0 0 0 0 50 0 4 50 0 0 0 0 0 0 50 1 1 1 CO 1 1 Example 8 (---1Part of Compound A, 0.1 part of isopropyl myristate and 0.3 part of:cyphenothrin were dissolved in a mixture ef 20.0 parts of dodecylbenzene and 39.5 parts of kerosene. The resulting mixture was charged into a container. A nozzle was provided on the container. 40.0 Parts of a propellant mixture of propane and butane was compressed through the nozzle into the insecticidal compositic.r.' to obtain an aerosol.

Example 9

1.0 Part of Compound A and 1.0 part of isopropyl myristate were dissolved in a mixture of 20.0 parts of i-opropyl alcohol and 28.0 parts of kerosene. The resulting mixture was charged into a container. A nozzle was provided on the container. 50.0 Parts of a propellant mixture of propane, butane and dimethyl ether was compressed through the nozzle into the insecticidal composition to obtain an aerosol.

Example 10

1-A Parts of Compound A and 31.0 parts of isopropyl myristate were dissolved in 18.0 parts of kerosene. The resulting mixture was charged into a container.- A nozzle was provided on the container.

50.0 Partsof apropellantmixture of propaner butane and dimethyl ether was compressed through the nozzle into the insecticidal composition to obtain an aerosol.

11 .,1, n, - 1 Example 11

0 Part of Compound 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. The resulting mixture was changed into a container. A nozzle was provided on the container. 50.0 Parts of a propellant mixture of propane, butane and dimethyl ether was compressed through the nozzle into the insecticidal composition to obtain an aerosol.

Test Example

Each of the insecticidal compositions obtained in Examples 1 to 7 and Comparative Examples 1 to 4 was diluted with.acetone to obtain a solution containing 0.189 g/e of Compound A. 0.3 Milliliter of the solution was coated onto a petri dish of 8.5 cm, in diameter so that Compound A was attachedto the petri dish in an amount of 0.0567 mg. That is, Compound A was attached to the petri dish in a ratio of 10 Mg/M2. After the petri dish had been dried by evaporation of acetoner 10 German cockroaches (Blattella qermanica) were released therein. The knock-d'Own effect, KT50 (a time required for knocking down 50% of the cockroaches) was determined. . Table 2 shows the results.

11 Table 2 - KT50 (min) to German cockroach 1 0.8 2 0.9 3 1.0 Example

4 0.9 1.1 6 0.9 7 1.2 1 3.0 Comparative 2 2.8 Example 3 4.1

4 3.3 1;, 11

Claims

CLAIMS:

1. A-"! insecticidal composition which comprises:

(a) 2,4-dioxo-l-(2-propynyl)imidazolidin-3ylmethyl chrysanthemate, (b) at least one carboxylic acid ester selected from monocarboxylic acid esters having 16-19 carbon atoms and dicarboxylic acid esters having 16- 19 carbon atoms, and optionally (c) at least one inert carrier, t-.'-.ie weight ratio of (a) to (b) being from 3:1 to 1:100.

2. An insecticidal composition according to Claim 1, wherein the carboxylic acid ester is selected from dibutyl ph-iialate, isopropyl palmitate, isopropyl myristate and hexyl laurate.

3. An insecticidal composition according to Claim 2, wherein the carboxylic acid ester is dibutyl phthalate.

4. An insecticidal composition according to Claim the carboxylic acid ester is isopropyl 2r wherein t palmitate.

5. An insecticidal composition according to Claim 2j, wherein the carboxylic acid is isopropyl myristate.

6.

An insecticidal composition according to Claim 2r wherein the carboxylic acid is hexyl laurate.

7.. A method for controlling insects which comprises..

applying to insects an insecticidal j 1 composition comprising:

(a) 2,.4-dioxo-l-(2-propynyl)imidazolidin-3ylmethyl chrysanthemate and (b) a: least one carboxylic ester selected from monocarboxyl-ic acid esters having 16-1.1% carbon atoms and dicarboxylic acid esters having 16-19 carbon atoms, weight ratio of (a) to (b) being from 3:1 to 1:100.

8. A process for preparing an insecticidal composition which comprises:

(a) 2,4-dioxo-l-(2-propynyl)imidazolidin-3ylmethyl chrysanthemate and (b) at least one carboxylic ester selected from monocarbox.-11-ic acid esters having 16-19 carbon atoms and dicarboxylic acid esters having 16-1. 9 carbon atoms, An a weight ratio of (a) to (b)-of from 3:1 to 1:100, undsheat.

9. A process for preparing an insecticidal aerosol which comprises; charging an insecticidal,'composition comprising:.

1 (a) 2,4-dioxo-l-(2-propynyl)imidazolidin-3-,.

ylmethyl chrysanthemate and (b) - at least one carboxylic ester selected from monocarboxylip acid esteis z 1 having 16-19 carbon atoms and dicarboxylic acid esters having 16-19 carbon atoms, wherein the weight ratio of (a) to (b) is from 3:1 to 1:100, into a container, ---roviding the container with a nozzle, and compressing a propellant through the nozzle into the.-isecticidal composition in the container.

L House. Cardiff Road. Newport. Gwent NP9 I RH. Furthe o jes may be obtained from r cop s It Published 1991 at Ihe Patent Office, Concepi techrmulque d. St Mary Cray, Kent.

point. Cwmfelinfach, Cross Keys. Newport. NPI 7HZ. Printed by Multiplex Sales Branch. Unit 6. Nine Mile 1