CA2040370C

CA2040370C - Insecticidal compositions

Info

Publication number: CA2040370C
Application number: CA002040370A
Authority: CA
Inventors: Kazunobu Dohara; Mitsuyasu Makita; Yasuo Abe
Original assignee: Sumitomo Chemical Co Ltd
Current assignee: Sumitomo Chemical Co Ltd
Priority date: 1990-04-24
Filing date: 1991-04-12
Publication date: 2000-11-14
Anticipated expiration: 2011-04-12
Also published as: PT97450A; YU73691A; RU2035142C1; KR910017934A; LV10158A; CA2040370A1; PT97450B; YU47780B; LTIP1063A; MX172672B; KR0161534B1; ZA912907B; LV10158B; LT3606B; ES2035768B1; ES2035768A1; BR9101639A

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 monocarboxylic acid ester having 16 to 19 carbon atoms and dicarboxylic acid ester having 16 to 19 carbon atoms, the weight ratio of (a) to (b) being from 3:1 to 1:100.

Description

INSECTICIDAL COMPOSITIONS
1 The present invention relates to an insecticidal composition.

2,4-Dioxo-1-(2-propynyl)imidazolidin-3-ylmethyl chrysanthemate having the formula (hereinafter Compound A), O O
CH = CCH2~~ CH20C CH=C(CH3)2 l~\p CH3 CH3 is a compound disclosed in USP 4,176,189, and is known to be usable as an active ingredient for insecticides.
However, the compound does not exhibit a satisfactorily high insecticidal activity when used alone.
1.0 The present inventors have extensively studied to strengthen the insecticidal activity of Compound A, and as a result have found that when (b) at least one carboxylic acid ester selected from the group consisting of monocarboxylic acid esters having 16 to 19 carbon 1.5 atoms and dicarboxylic acid esters having 16 to 19 carbon atoms is added to (a) Compound A so that the weight ratio of (a) to (b) is from 3:1 to 1:100, the insecticidal activity of Compound A is remarkably strengthened. The present inventors have thus attained ~0 to the present invention.

2~4Q3~0 1 According to the present invention, there is provided an insecticidal composition comprising:
(a) 2,4-dioxo-1-(2-propynyl)imidazolidin-3-ylmethyl chrysanthemate (Compound A), (b) 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 (a) to (b) being from 3:1 to 1:100, and optionally l0 (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 thereof can be incorporated in the insecticidal 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 esters having 16 to 19 carbon atoms and the dicarboxylic , 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, 2403:~
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 (1RS)-cis,trans-chrysanthemate [allethrin];

3.4,5,6-tetrahydrophthalimidomethyl (1RS)-cis,trans-chrysanthemate [tetramethrin];
(S)-2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl (1R)-cis,trans-chrysanthemate [prallethrin];
3-phenoxybenzyl (1RS)-cis,trans-chrysanthemate [phenothrin];
5-benzyl-3-furylmethyl (1RS)-cis,trans-chrysanthemate [resmethrin];
(RS)-a-cyano-3-phenoxybenzyl (1R)-cis,trans-chrysanthemate [cyphenothrin];
3-phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecaboxylate [permethrin];
(RS)-a-cyano-3-phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-carboxylate [cypermethrin];
(S)-a-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate [deltamethrin];
(RS)-a-cyano-4-fluoro-3-phenoxybenzyl (1RS)-ci~,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclo-propanecarboxylate [cyfluthrin];
-2~~~3~~
1 5-(2-propynyl)furufuryl (1RS)-cis,trans-chrysanthemate [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 [fenitrothion];
2-(1-methyethoxy)phenyl methylcarbamate [propoxur];

4-phenoxyphenyl (RS)-2-(2-pyridyloxy)propyl ether [pyriproxyfen];
isopropyl (2E,4E)-11--methoxy-3,7,11-trimethyl-2,4-dodecadienoate [methoprene];
ethyl (2E,4E)-3,7,11-trimethyldodeca-2,4-dienoate [hydroprene];
1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea [diflubenzuron]; and N-cyclopropyl-1,3,5-triazine-2,4,6-triamine [cyromazine].
Specific examples of the synergists are a-[2-(2-butoxyethoxy)ethoxy]-4,5-methylenedioxy-2-propyltoluene (piperonyl butoxide), N-(2-ethylhexyl)-bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide (MGK-264), octachlorodipropyl ether (S-421), etc.
Specific examples of the solvents are isopropyl alcohol, kerosene, dodecylbenzene, etc.

:o~o~~o 1 Specific examples of the propellants are propane/butane, dimethyl ether, FreonTM gas ( f:luorocarbons ) , 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 20 temperature or under heating.
Insects and acarina against which the composition of the present invention thus prepared is effective are listed below:
Lepidoptera casemaking clothes moth (Tinea nellionella), webbing clothes moth (Tineola bisselliella), etc.
Diptera Culex spp. such as common mosquito (Culex pipiens pallens) and Culex tritaeniorhynchus;
Aedes spp. such as Aedes aegypti; and Aedes albopictus; Anor~heles spp. such as Anopheles sinensis midges (Chironomidae);
Muscidae such as housefly (Musca domestica) and false stablefly (Muscina stabulans);
Calliphoridae; Sarcophagidae; little housefly (Fannia canicularis);

20403'0 1 Anthomyiidae such as seedcorn maggot (Delia platura) and onion maggot (Delia antiaua);
fruit flies (Tephritidae); Drosophilidae; moth flies (Psychodidae); black flies (Simuliidae);
Tabanidae; stable flies (Stomoxyidae) etc.
Dictyoptera German cockroach (Blattella germanica), smokybrown cockroach (Periplaneta ful'_q_inosa), 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 Reticulitermes speratus, Coptotermes formosanus etc.
Ixodidae Boophilus microplus, etc.
House dust mites Acaridae such as Tyrophagus putrescentiae, Pyroalyphidae such as Dermatopha9oides farinae, Cheyletidae such as Chelacaropsis moorei, Macronyssidae such as Ornithonyssus bacoti, etc.

1 The composition of the present invention can b~e 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 ef 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 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 50°C) to obtain a liquid insecticidal composition.
Table 1 lists the insecticidal compositions obtained in the same manner as above.

2040~'~0 ~

W U

ro U

r-I

~ro H O O O O O O O O O O
O

ro u1 W v 1~

N

v 0 0 0 0 0 0 m ~ O
' .
~ rl b r-I
v ~

rorov N

",e'~ ~
, r~i ., x a p v ro o 0 0 0 0 0 0 0 0 0 rox sr U 'J' Clv N

O
rl rl .-I '--I
I

~ ~~~ O O O O O O O O O A
.aJ O

~' H

ro O W W ' H U

~-~I
I

I ~r N v p1 O O O O O O O O O
a.,~ O
.~.7 N O ov o w,M
>a ro H a 9~f .i.~

I

ro ~'dN

H
rl 0 0 0 0 0 0 0 0 0 ~ ri tf1t~tf1lf1tl1O Lf1 tf1 LT l U'1 O

r1 r ~

rob ~

U

r-1N M d~tff1GC~ rl N
M
d' v U rl v ro s~

W ~W

O

U

~0~03~0 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 1.0 Part of Compound A and 1.0 part of isopropyl myristate were disso'_ved in a mixture ef 20.0 parts of isopropyl alcohol and 28.0 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.
Example 10 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.
_ g _ zo~o3~0 1 Example 11 1.0 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 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 g/~ 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 isr 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 acetone, 10 German cockroaches (Blattella aermanica) were released therein. The knock-down effect, KT50 (a time required for knocking down 50~ of the cockroaches) was determined. Table 2 shows the results.

2U403'~~
Table 2 KZ50 (min) to German cockroach 1 0.8 2 0.9 3 1.0 Example 4 0.9 5 7..1 6 0.9 '7 1.2 1 3.0 Comparative2 2.8 Example 3 4.1 4 3.3

Claims

1. An insecticidal composition which comprises:
(a) 2,4-dioxo-1-(2-propynyl)imidazolidin-3-ylmethyl chrysanthemate;
(b) at least one carboxylic acid ester selected from the group consisting of 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;
wherein the weight ratio of (a) to (b) is from 3:1 to 1:100.

2. The insecticidal composition according to claim 1, wherein the carboxylic acid ester is selected from the group consisting of dibutyl phthalate, isopropyl palmitate, isopropyl myristate, and hexyl laurate.

3. The insecticidal composition according to claim 1 or 2, further comprising a propellant to form an aerosol.

4. The insecticidal composition according to claim 3, wherein the propellant is selected from the group consisting of dimethyl ether, and a mixture of dimethyl ether and liquefied petroleum gas.

5. An insecticidal aerosol composition which comprises:
(a) 2,4-dioxo-1-(2-propynyl)imidazolidin-3-ylmethyl chrysanthemate;
(b) at least one carboxylic acid ester selected from the group consisting of monocarboxylic acid esters having 16-19 carbon atoms and dicarboxylic acid esters having 16-19 carbon atoms;
(c) kerosene; and (d) a propellant selected from the group consisting of dimethyl ether and a mixture of dimethyl ether and liquefied petroleum gas;
wherein the weight ratio of (a) to (b) is from 3:1 to 1:100.

6. The insecticidal aerosol composition according to claim 5, wherein the contents of (a), (b), (c) and (d) are 0.001 to 5% by weight, 0.005 to 60%
by weight, 5 to 80% by weight and 20 to 80% by weight, respectively.

7. The insecticidal aerosol composition according to claim 6, wherein the propellant is a mixture of dimethyl ether and liquefied petroleum gas and the weight ratio of dimethyl ether to liquefied petroleum gas is 100:0 to 40:60.

8. The insecticidal aerosol composition according to claim 5, 6 or 7, wherein the carboxylic acid ester is selected from the group consisting of dibutyl phthalate, isopropyl palmitate, isopropyl myristate, and hexyl laurate.

9. A method for controlling insects which comprises:
applying to insects an insecticidal composition comprising:
(a) 2,4-dioxo-1-(2-propynyl)imidazolidin-3-ylmethyl chrysanthemate; and (b) at least one carboxylic ester selected from the group consisting of monocarboxylic acid esters 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.

10. A method for controlling insects which comprises:
applying to insects an insecticidal aerosol composition comprising:
(a) 2,4-dioxo-1-(2-propynyl)imidazolidin-3-ylmethyl chrysanthemate;
(b) at least one carboxylic acid ester selected from the group consisting of monocarboxylic acid esters having 16-19 carbon atoms and dicarboxylic acid esters having 16-19 carbon atoms;
(c) kerosene; and (d) a propellant selected from the group consisting of dimethyl ether, and a mixture of dimethyl ether and liquefied petroleum gas;
wherein the weight ratio of (a) to (b) is from 3:1 to 1:100.

11. The method according to claim 9 or 10, wherein the insects are cockroaches.