Title of Invention

AN INSECTICIDAL INCENSE COMPOSITION AND A PROCESS FOR PRODUCING THE SAME

Abstract

AN INSECTICIDAL INCENSE COMPOSITION AND A PROCESS FOR PRODUCING THE SAME An insecticidal incense composition in the form of an emulsifiable concentrate which comprises a compound represented by the formula (1): wherein R is a hydrogen atom, a methyl group, a methyl group or a methoxy group or a methoxymethyl group, X and Y are independently a chlorine atom, a methyl group or a hydrogen atom;a calcium alkylbenzene sulfonate; a polyoxyalkylene alkyl ether; and an insecticidal incense base consisting of an organic filter and a binder. The invention also relates to a process for producing the same.

Full Text

The present invention relates to an insecticidal incense composition, and a process for producing the same. wherein R is a hydrogen atom, a methyl group, a methoxy group or a methoxymethyl group, and X and Y are independently a chlorine atom, a methyl group or a hydrogen atom, is known as an insecticidal ingredient in USP-6,225,495, USP-6,294,576, USP-4,889,872 and so on. It is also known that the compound can be formulated to incense composition (mosquito coil) in USP-6,225,495 and USP-6,294,576. However, sometimes, the above-mentioned insecticidal incense composition does not exhibit sufficient efficacy. Then, it is desired to develop an insecticidal incense composition which can exhibit more superior efficacy. SUMMARY OF THE INVENTION An object of the present invention is to provide an insecticidal incense composition which is excellent in efficacy. Other objects as well as advantages of the present invention will become apparent to those skilled in the art from the following description. The present inventor have found that the efficacy of an insecticidal incense composition can be improved by compounding a calcium alkylbenzene sulfonate and a polyoxyalkylene alkyl ether in addition to an effective component, i.e., a compound represented by the following formula (1) in an insecticidal incense base, and attained to the present invention. That is, the present invention provides: 1. An insecticidal incense composition which comprises a compound represented by the formula (1): wherein R is a hydrogen atom, a methyl group, a methoxy group or a methoxymethyl group, and X and Y are independently a chlorine atom, a methyl group or a hydrogen atom (hereinafter referred to as a compound (1)); a calcium alkylbenzene sulfonate; a polyoxyalkylene alkyl ether; and an insecticidal incense base; 2. The composition according to the above 1 which comprises 0.002 to 0.05% by weight of a compound (1), 0.002 to 0.05% by weight of a calcium alkylbenzene sulfonate, and 0.002 to 0.05% by weight of a polyoxyalkylene alkyl ether based on the composition; 3. The composition according to the above 1 which further comprises an alkylbenzene; 4. The composition according to the above 3 which comprises 0.03 to 0.8% by weight of an alkylbenzene based on the composition; 5. The composition according to the above 1 which is in the shape of a stick; 6. The composition according to the above 1 which is in the shape of a coil; 7. An emulsifiable concentrate for producing an insecticidal incense composition which comprises a compound (1), a calcium alkylbenzene sulfonate, a polyoxyalkylene alkyl ether, and an alkylbenzene; 8. A process for producing an insecticidal incense composition which comprises the steps of: mixing a diluted emulsifiable concentrate for producing an insecticidal incense composition comprising a compound (1) , a calcium alkylbenzene sulfonate, a polyoxyalkylene alkyl ether, and an alkylbenzene, and an insecticidal incense base; and molding and drying the resultant mixture; and 9. An insecticidal incense composition obtained by the process according to the above 8. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS In the present invention, examples of the compound (1) include 2,3,5,6-tetrafluoro-4-methylbenzyl 3- (1-propenyl)- 2,2-dimethylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- methoxymethylbenzyl 3-(1-propenyl)-2,2- dimethylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- methoxybenzyl 3-(1-propenyl)-2,2- dimethylcyclopropanecarboxylate and 2,3,5,6- tetrafluorobenzyl 3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropanecarboxylate. These compounds are known, or can be produced according to a known method. The insecticidal incense base to be used in the present invention may be a conventional one and, usually, it is composed of a combustion-supporting agent (organic filler) and a binder. Examples of the combustion-supporting agent include dried plant meal or flour such as wood flour, pyrethrum marc, surface skin meal of citrus fruits, palm fruit shell powder, coconut shell powder, walnut shell powder, and the like, as well as carbon powders such as charcoal powder, active carbon powder, coal powder, and the like. They can be used alone or a combination of two or more thereof. Examples of the binder include tabu-no-ki tree {Machilus thunbergii) powder, starches (e.g., tapioca starch, corn starch, wheat starch), casein, Siam glue, methyl cellulose, carboxymethylcellulose, high molecular weight compounds such as polyvinyl alcohol, and the like. They can be used alone or a combination of two or more thereof. Usually, the calcium alkylbenzene sulfonate to be used in the present invention is calcium (C8-Ci4) alkylbenzene sulfonate. As the polyoxyalkylene alkyl ether, there is, for example, polyoxy (C2-C3) alkylene alkyl ether such as polyoxyethylene (Ci2-Cie) alkyl ether. The insecticidal incense composition of the present invention is composed of an insecticidal base containing a compound (1) , a calcium alkylbenzene sulfonate, and a polyoxyalkylene alkyl ether. Usually, the insecticidal incense composition of the present invention contains 0.002 to 0.05% by weight of a compound (1) , 0.002 to 0.05% by weight of a calcium alkylbenzene sulfonate, and 0.002 to 0.05% by weight of a polyoxyalkylene alkyl ether based on the composition. The insecticidal incense composition of the present invention may further contain an alkylbenzene. Examples of the alkylbenzene include a benzene substituted with a Ci0-C14 alkyl group. Specifically, there are, for example, decylbenzene, undecylbenzene, dodecylbenzene and tridecyclbenzene. When the insecticidal incense composition of the present invention contains a alkylbenzene, the content thereof is usually 0.03 to 0.8% by weight based on the composition. The insecticidal incense composition may further contain a colorant, a preservative, etc., if necessary. Examples of the colorant include organic pigments such as malachite green, etc. Examples of the preservative include acids such as benzoic acid, sorbic acid, dehydroacetic acid, p-hydroxybenzoic acid, o-phenylphenol, etc., as well as salts and esters thereof. The insecticidal incense composition of the present invention may contain each of them in an amount of 1% by weight or less. The insecticidal incense composition of the present invention can be produced, for example, by mixing a diluted EC for producing an insecticidal incense composition comprising a compound (1), a calcium alkylbenzene sulfonate, a polyoxyalkylene alkyl ether, and an alkylbenzene; an insecticidal incense base (combustion-supporting agent, binder, etc.); and further, if necessary, water. After kneading, the resultant mixture is molded with a molder such as a pressing machine, an extruder, an embossing machine, a stamping machine, etc., into an appropriate shape such as a stick, a coil, etc., followed by drying the molded mixture to obtain the insecticidal incense composition of the present invention. The diluted EC for producing an insecticidal incense composition is prepared by diluting the EC for producing the insecticidal incense composition of the present invention which comprises a compound (1), a calcium alkylbenzene sulfonate, a polyoxyalkylene alkyl ether, and an alkylbenzene, with water. Usually, the emulsion of the present invention is diluted with 10 to 1000 parts by weight of water per 1 part by weight of the EC. For producing the insecticidal incense composition of the present invention, usually, 0.1 to 1.2 parts by weight of the diluted EC is mixed with 1 part by weight of the insecticidal incense base. The EC for producing the insecticidal incense composition of the present invention contains a compound (1) , a calcium alkylbenzene sulfonate, a polyoxyalkylene alkyl ether, and an alkylbenzene. Usually, the above EC contains 2.5 to 20% by weight of a compound (1), 2.5 to 20% by weight of a calcium alkylbenzene . sulfonate, 2.5 to 20% by weight of a polyoxyalkylene alkyl ether, and 40 to 92.5% by weight of an alkylbenzene. The EC can be produced, for example, by mixing a given amount of a compound (1); an emulsifier mixture containing a given amount of a calcium alkylbenzene sulfonate and a given amount of a polyoxyalkylene alkyl ether; and a given amount of an alkylbenzene. The insecticidal incense composition of the present invention thus obtained can be used according to a conventional manner. That is, the insecticidal incense composition of the present invention can be smoked at a habitat of noxious insects (e.g., mosquitoes, flies, etc.) or in the vicinity thereof such as inside a room, etc. As burning the insecticidal incense composition, the effective component, a compound, (1), is volatilized and scattered, thereby controlling noxious insects. The following Production Example, Comparative Example and Test Example further illustrate the present invention in detail but are not to be construed to limit the scope of the present invention. In the following Examples, all "parts" are by weight unless otherwise stated. Production Example (1) An EC for producing an insecticidal incense composition (hereinafter referred to as the emulsion A) was obtained by mixing 5 parts of 2,3,5,6-tetrafluoro-4~ methoxymethylbenzyl (1R)-trans-3-(1-propenyl)-2,2- dimethylcyclopropanecarboxylate (the ratio of geometric isomers of 1-propenyl group: Z/E=about 8/1); a mixture of 4.5 parts of calcium alkylbenzene sulfonate, 4.5 parts of polyoxyalkylene alkyl ether and 6 parts of an aromatic solvent (mixture of Newkalgen 155A manufactured by Takemoto Oil & Fat Co., Ltd./Newkalgen 155F manufactured by Takemoto Oil & Fat Co., Ltd. = 2/1); and 80 parts of an alkylbenzene (Mitsubishi Soft Alkylbenzene SAB-G manufactured by Mitsubishi Chemical Corporation). (2) A diluted EC for producing an insecticidal incense composition was prepared by mixing 0.1 part of the EC A with 49.9 pars of water. Fifty parts of the diluted EC was mixed with 15 parts of pyre thrum marc, 15 parts of wood flour, 2 0 parts of tabu-no-ki tree powder and 10 parts of water. The resultant mixture was thoroughly kneaded, followed by molding and drying (at 4 0 °C for 6 hours) to obtain the desired insecticidal incense composition (hereinafter referred to as the composition 1 of the present invention). Comparative Example An insecticidal incense composition (hereinafter referred to as the comparative composition) was obtained by mixing 10 mL of a 0.05% (w/v) solution of 2,3,5,6- tetrafluoro-4-methoxymethylbenzyl (1R)-trans-3- (1- propenyl)-2,2-dimethylcyclopropanecarboxylate (the ratio of geometric isomers of 1-propenyl group: Z/E=about 8/1) in acetone, 15 g of pyrethrum marc, 15 g of wood flour, 20 g of Siam glue and 60 mL of water, and thoroughly kneading the resultant mixture, followed by molding and drying (at 40°C for 6 hours) . Test Example The efficacy of the insecticidal incense composition of the present invention will be illustrated by the following test. Ten female adult brown house mosquitoes (Cuiex pipiens pallens) were introduced into a glass tube of 4 cm inner diameter and 12 cm long. The both ends of the tube were covered with nylon nets of 16 mesh. On the other hand, a plastic transparent cylinder of 20 cm inner diameter and 30 cm high was mounted on a stainless cylinder of 20 cm inner diameter and 80 cm high. The above glass tube in which the mosquitoes were introduced was placed inside the plastic cylinder so that the lower end of the glass tube came to substantially the same level of the lower end of the plastic cylinder. Then, a composition to be tested which was stably burning was placed inside the bottom center of the stainless cylinder. After placing a composition to be tested inside the stainless cylinder, the number of knocked down mosquitoes were counted with time and, based on the results, time . required for knocking down 50% of the mosquitoes (KT50) and that required for knocking down 90% of the mosquitoes (KT90) were calculated. The results are shown in Table 1. As shown in Table 1, the composition 1 of the present invention knocked down 90% of mosquitoes in about 6 minutes. On the other hand, the comparative composition knocked down only 50% of mosquitoes even after about 7 minutes. Thus, it is clear that the insecticidal incense composition of the present invention exhibits superior efficacy. WE CLAIM: ' ' '■ 'i 1. An insecticidal incense composition in the form of an emulsifiable concentrate which comprises a compound represented by the formula (1): wherein R is a hydrogen atom, a methyl group, a methyl group or a methoxy group or a methoxymethyl group, X and Y are independently a chlorine atom, a methyl group or a hydrogen atom; a calcium alkylbenzene sulfonate; a polyoxyalkylene alkyl ether; and an insecticidal incense base consisting of an organic filter and a binder. 2. The composition according to claim 1 which comprises 0.002 to 0.05% by weight of a compound of the formula (1), 0.002 to 0.05% by weight of a calcium alkylbenzene sulfonate, and 0.002 to 0.05% by weight of a polyoxyalkylene alkyl ether based on the composition. 3. The composition according to claim 1 which comprises an alkylbenzene. 4. The composition according to claim 3 which comprises 0.03 to 0.8% by weight of an alkylbenzene based on the composition. 5. A process for producing an insecticidal incense composition which comprises the steps of: mixing a diluted emulsifiable concentrate for producing an insecticidal incense composition comprising a compound represented by the formula (1) wherein R is a hydrogen atom, a methyl group, a methoxy group or a methoxvmethyl group, X and Y are independently a chlorine atom, a methyl group or a hydrogen atom; a calcium alkylbenzene sulfonate; a polyoxyalkylene alkyl ether; and an alkylbenzene; and an insecticidal incense base; and molding and drying the resultant mixture. 6. An insecticidal incense composition obtained by the process according to claim 8.

Documents:

115-che-2004-abstract.pdf

115-che-2004-claims duplicate.pdf

115-che-2004-claims original.pdf

115-che-2004-correspondnece-others.pdf

115-che-2004-correspondnece-po.pdf

115-che-2004-description(complete) duplicate.pdf

115-che-2004-description(complete) original.pdf

115-che-2004-form 1.pdf

115-che-2004-form 18.pdf

115-che-2004-form 26.pdf

115-che-2004-form 3.pdf

115-che-2004-form 5.pdf

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