AU636471B2

AU636471B2 - Insecticidal compositions

Info

Publication number: AU636471B2
Application number: AU74201/91A
Authority: AU
Inventors: Yasuo Abe; Kazunobu Dohara; Mitsuyasu Makita
Original assignee: Sumitomo Chemical Co Ltd
Current assignee: Sumitomo Chemical Co Ltd
Priority date: 1990-04-24
Filing date: 1991-04-09
Publication date: 1993-04-29
Anticipated expiration: 2011-04-09
Also published as: GB9107920D0; GB2243297B; IT1244979B; ITRM910273A1; JPH049306A; HU209631B; NL9100673A; ITRM910273A0; DE4113383C2; SG156894G; DE4113383A1; BE1004726A3; AU7420191A; CH682706A5; GB2243297A; FR2661070B1; JPH0764687B2; FR2661070A1

Description

AWi

AUSTRALIA

636471 PATENTS ACT 1952 Form COMPLETE SPECIFICATION

(ORIGINAL)

FOR OFFICE USE Short Title: Int. Cl: Application Number: Lodged: Complete Specification-Lodged: Accepted: Lapsed: Published:

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Priority: Related Art: TO BE COMPLETED BY APPLICANT Name of Applicant: Address of Applicant: SUMITOMO CHEMICAL COMPANY,

LIMITED

5-33, KITAHAMA-4-CHOME

CHUO-KU

OSAKA

JAPAN

GRIFFITH HACK CO., 601 St. Kilda Road, Melbourne, Victoria 3004, Australia.

Actual Inventor: Address for Service: Complete Specification for the invention entitled: INSECTICIDAL COMPOSITIONS.

The following statement is a full description of this invention including the best method of performing it known to me:- 1 The present invention relates to an insecticidal composition.

2,4-Dioxo-l-(2-propynyl)imidazolidin-3ylmethyl chrysanthemate having the formula (hereinafter Compound A), 0

O

CH CCH2N NCH20C CH=C(CH3)2 O CH 3

CH

3 00 0 000 is a compound disclosed in USP 4,176,189, and is known :0.

s 0ee to be usable as an active ingredient for insecticides.

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

10 The present inventors have extensively studied to strengthen the insecticidal activity of Compound A, and as a result have found that when 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 is added to Compound A so that the weight ratio of to is from 3:1 to 1:100, the insecticidal activity of Compound A is remarkably strengthened. The present inventors have thus attained to the present invention.

1 According to the present invention, there is provided an insecticidal composition comprising: 2,4-dioxo-l-(2-propynyl)imidazolidin-3ylmethyl chrysanthemate (Compound A), at least one member 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, the weight ratio of to being from 3:1 to 1:100, and optionally at least one inert carrier.

Compound A includes various optical and .geometrical isomers. Of the isomers, an isomer *000 S. exhibiting an insecticidal activity and the mixtures 0e thereof can be incorporated in the insecticidal 15 composition of the present invention. The content of Compound A in the composition of the present invention is usually 0.001% to 75% by weight.

Specific examples of the monocarboxylic acid 4 esters having 16 to 19 carbon atoms and the dicarboxylic 20 acid esters having 16 to 19 carbon atoms are dibutyl phthalate, isopropyl palmitate, isopropyl myristate, hexyl laurate, etc. These compounds may also be used in admixture thereof. One or more compounds selected out of these compounds are usually blended in the composition 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, 2 1 synergists, perfumes, fungicides, solvents, propellants, solid carriers, etc.

Specific examples of the other insecticides are: (RSN-3-allyl-2-methyl-4-oxocyclopent-2-enyl (lRS)-cis,trans-chrysanthemate [allethrin]; 3,4,5,6-tetrahydrophthalimidomethyl (iRS)cis,trans-chrysanthemate [tetramethrin]; -2-methyl-4-oxo-3- (2-propynyl )cyclopent-2enyl (lR)-cis,trans-chrysanthemate Iprallethrin]; 3-phenoxybenzyl (lRS) -cis, trans-chrysanthemate 0060 [phenothrin]; 5-benzyl-3-furylmethyl (lRS) -cis ,trans- 0:90 chrysanthemate (resmethrin]; 15 (RS)-c-cyano-3-phenoxybenzyl (lR)-cis,transchrysanthemate tcyphenothrin]; 3-phenoxybenzyl (lRS)-cis,trans-3-(2,2dichiorovinyl ,2-dimethy'Lcyclopropanecaboxylate [permethrin]; (RS)-c-cyano-3-phenoxybenzyl (lRS)-cis,trans- 3- 2-dichlorovinyl) 2-dimethylcyclopropane- Ccarboxylate tcypermethrin]; (S)-c-cyano-3-phenoxybenzyi (lR)-cis-3-( 2,2dibromovinyl 2-diniethylcyclopropanecarboxylate [deltamethrin]; (RS -c-cyano-4-fiuoro-3-phenoxybenzyl (lRS) cis, trans-3- 2-dichiorovinyl 2-dimethylcyclopropanecarboxylate [cyfluthr in]; -3 1 5- (2-propynyl) furufury. (lRS) -cis, transchrysarithemate £furamethrin); 2- (4-ethoxyphenyl) -2-rnethylpropy. 3phenoxybenzyl ether [ethofenprox]; 2,2-dichiorovinyl dirnethyl phosphate [dichlorvos); 0,0-dimethyl 0- (3-methyl-4-nitrophenyl) phosphorothioate [fenitrothion]; 2-(l-methyethoxy)phenyl methylcarbainate [propoxur]; 4-phenoxyphenyl 2-pyridyloxy)prc-py1 ether [pyriproxyfen]; 0.9 isopropyl (2E,4E)-l1-methoxy-3,7,1l-trimethyl- 2,4-dodecadienoate [methoprene]; 15 ethyl (2E,4E)-3,7,ll-trimethyldodeca-2,4- 0 age dienoate [hydroprene]; 1- (4-chiLorophenyl (2 ,6-difluorobenzoyl )urea [diflubenzuron]; and N-cyclopropyl-l, 3, 5-triazine-2, 4, 6-triamine [cyromazine).

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

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

4- 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 the &see composition of the present invention thus prepared is effective are listed below: Lepidoptera 15 casemaking clothes moth (Tinea pellionella), *e webbing clothes moth (Tineola bisselliella), etc.

Diptera Culex spp. such as common mosquito (Culex 20 pipiens pallens) and Culex tritaeniorhynchus; Aedes spp. such as Aedes aegypti; and Aedes albopictus; Anopheles spp. such as Anopheles sinensis midges (Chironomidae); Muscidae such as housefly (Musca domestica) and false stablefly (Muscina stabulans); Calliphoridae; Sarcophagidae; little housefly (Fannia canicularis); 5 1 Anthomyiidae such as seedcorn maggot (Delia platura) and onion maggot (Delia antictua); fruit flies (Tephritidae); Drosophilidae; moth flies (Psychodidae); black flies (Simuliidae); Tabanidae; stable flies (Stc'moxyidae) etc.

Dictyoptera German cockroach (Blattella, germanica.), smokybrown cockroach (Periplaneta fuligqgosa), American cockroach (Periplaneta americana), brown cockroach (Periplaneta brunnea), oriental cockroach (Blatta orientalis), etc.

Hymenoptera 0*0~ ants (Formicidae), hornets (Vespidae), Bethylidae, sawflies (Tenthredinidae) such as cabbage sawfly (Athalia rosae ruficornis), etc.

Is opt era Reticulitermes speratus, Coptotermes formosanus etc.

0:0 20 Ixodidae *000ef Boophilus microplua, etc.

House dust mites Acaridae such as Tyrophagus putrescentiae, Pyroalyphidae such as Dermatophagoides farinae, Cheyletidae, such as hlcrpi moorei, Macronyssidae such as Ornithonyssus bacoti, etc.

-6 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 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% 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 e 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: do. trans configuration) and 50.0 parts of isopropyl myristate were mixed under heating (about 40 to 50 0 C) to obtain a liquid insecticidal composition.

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

@0 0 7 S S SO S S 03 5 a 30 0 0.e0 Table 1 ___________Composition (part by weight) Compound A Carboxylic acid ester7 (acid moiety:iT d-trans Zxso- ISO- Hexy. Dibutyll Di iso- Butyl Ethyl configura- propyl propyl laurate phtha-I pr opyl stearate acetate tion) myris- palmi- late adipate tate tate 11 99 0 0 0 0 0 0 2 1~0 9 3 5090 0 0 0 0 0 0 Example3505000000 50 30 50 0 0 0 0 0 4 70 30 50 0 0 0 0 0 6 50 0 0 50 0 0 0 0 7 50 0 0 0 50 0 0 0 Compara.$ve Example 3 4 100 50 50 50 0 0 0 0 0 0 0 0 0 50 0 0 0 0 50 01 0 -0 0 1 Example 8 0.1 Part of Compound A, 0.1 part of isopropyl myristate and 0.3 part of cyphenothrin were dissolved in a mixture of 20.0 parts of dodecylbenzene and 39.5 parts of kerosene. The resulting mixture was charged in a container. A nozzle was provided to the container.

40.0 Parts of a propellant mixture of propane and butane was compressed through the nozzle into the insecticidal composition to obtain an aerosol.

Example 9 6 *0 1.0 Part of Compound A and 1.0 part of 0. isopropyl myristate were dissolved in a mixture of 20.0

I.

parts of isopropyl alcohol and 28.0 parts of kerosene.

0 The resulting mixture was charged in a container. A nozzle was provided to 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 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 charged in a container. A nozzle was provided to 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.

9 1 Example 11 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 in a container. A nozzle was provided to 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 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 attached to 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 mgim 2 After the petri dish had been dried by evaporation of acetone, German cockroaches (Blattella germanical were released therein. The knock-down effect, KT50 (a time required S S" for knocking down 50% of the cockroaches) was determined. Table 2 shows the results.

10 Table 2 (min) to German cockroach 1i 0.8 2 0.9 Example 31.

4 0.9 1.1 6 0.9 7 1.2 1. Comparative 2 2.8 Example 3 4.1 4 3.3

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CE OR h 0 a 0e*C C. 0 05 4.

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e.g.

C.

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C CCC 00 a 0460 00 11

Claims

1. An insecticidal composition which comprises: 2,4-dioxo-l-(2-propynyl)imi.dazolidin-3-ylmethyl chrysanthenate, and at least one carboxylic acid ester selected from amoeea..a Am acid esters having 16-19 carbon atoms or dicarboxylic acid esters having 16-19 carbon atoms wherein the weight ratio of to is from 3:1 to 1:100.

2. An insecticidal composition according to Claim 1, wherein the carboxylic acid ester is dibutyl phthalate, isopropyl palmitte, isopropyl myristate or hexyl laurate. 15 3. An insecticidal composition according to Claim 1, wherein the carboxylic acid eater is dibutyl phthalate.

4. IAn 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. S: 6. An insecticidal composition according to Claim 1, 25 wherein the carboxylic acid ester is hexyl laurate.

7. An insecticidal composition according to any preceding claim further comprising at least one inert carrier.

8. A method for controlling insects which comprises: applying to insects an insecticidal composition comprising: 12 i-0 y^w^. 2,4-dioxo-l-(2-propynyl)imidazolidin-3-ylmethyl chrysanthemate and at least one carboxylic acid ester selected from monocarboxylic acid esters having 16-19 carbon atoms or dicarboxylic acid esters having 16-19 carbon atoms, in which the weight ratio of to is from 3:1 to 1:100.

9. A method of controlling insects which comprises applying to insects an insecticidal composition according to any one of claims 1 to 7. A process for preparing an insecticidal 15 composi'tion which comprises: mixing S(a) 2,4-dioxo-l-(2-propynyl)imidazolidin-3-ylmethyl chrysanthemate and at least one carboxylic acid ester selected from monocarboxylic acid esters having 16-19 carbo. atoms or dicarboxylic acid esters having 16-19 carbon atoms, in a weight ratio of to of from 3:1 to 1:100, under heat. 25 11. A process according to claim 10 for preparing an insecticidal composition according to any one of claims 1 to 7.

12. A process for preparing an insecticidal aerosol which comprises: charging an insecticidal composition comprising: 2,4-dioxo-l-(2-propynyl)imidazolidin-3-ylmethyl chrysanthemate and at least one carboxylic acid ester selected from monocarboxylic acid esters having 16-19 carbon atoms or dicarboxylic acid esters having 16-19 carbon atoms, wherein the weight ratio of to is from 3:1 to 1:100, into a container, providing a nozzle to the container, and compressing a propellant through the nozzle into the insecticidal composition in the container.

13. A process for preparing an insecticidal aerosol according to Claim 12 using an insecticidal composition according to any one of claims 1 to 7.

14. An insecticidal composition substantially as hereinbefore described with reference to any one of the foregoing examples apart from the test example. A method for controlling insects substantially as hereinbefore described with reference to any oLe of the foregoing examples apart from the test example.

16. A process for preparing an insecticidal composition substantially as hereinbefore described with reference to any one of the foregoing examples apart from the test example. 25 17. A process for preparing an insecticidal aerosol substantially as hereinbefore described with reference to any one of the foregoing examples apart from the test example. C Dated this 26th day of January 1993 SUMITOMO CHEMICAL COMPANY, LIMITED By its Patent Atcerneys: GRIFFITH HACK CO. Fellows Institute of Patent Attorneys of Australia.