Title of Invention

"PESTICIDAL EMULSIFIABLE CONCENTRATE"

Abstract

There is provided a pesticidal emulsifiable concentrate comprising pyridalyl, a polyoxyethylene polyoxypropylene polyarylphenol, an alkylarylsulfonate and 5 an aromatic hydrocarbon, preferably 5 to 60% by weight of pyridalyl, 2 to 15% by weight of the polyoxyethylene polyoxypropylene polyarylphenol, 2 to 15% by weight of the alkylarylsulfonate and 10 to 90% by weight of the aromatic hydrocarbon. The pesticidal emulsifiable concentrate is 10 excellent in emulsion stability.

Full Text

PESTICIDAL EMULSIFIABLE CONCENTRATE FIEDL OF THE INVENTION The present invention relates to a pesticidal emulsifiable concentrate. More specifically, it relates to a pesticidal emulsifiable concentrate comprising pyridalyl as an effective ingredient. BACKGROUND OF THE INVENTION Pyridalyl, i.e., 2,6-dichloro-4-(3,3- dichloroallyloxy)phenyl 3-[5-(trifluoromethyl)-2- pyridyloxy]propyl ether, represented by the formula (1): has been known in W096/11909 as an effective ingredient of a pesticide. Further, a pesticidal emulsifiable concentrate comprising pyridalyl as an effective ingredient has also been disclosed in W096/11909. OBJECTS OF THE INVENTION However, the pesticidal emulsifiable concentrate comprising pyridalyl as the effective ingredient disclosed in Preparation Example 1 of W096/11909 has not always sufficient emulsion stability depending upon conditions, when it is diluted with water. Then, it is desired to develop a pesticidal emulsifiable concentrate which comprises pyridalyl as an effective ingredient, and is excellent in emulsion stability. An object of the present invention is to provide a pesticidal emulsifiable concentrate which comprises pyridalyl as an effective ingredient, and is excellent in emulsion stability upon dilution with water. This object as well as other objects and advantages of the present invention will become apparent to those skilled in the art from the following description. SUMMARY OF THE INVENTION The present inventors have studied intensively to obtain a pesticidal emulsifiable concentrate which comprises pyridalyl as an effective ingredient, and is excellent in emulsion stability upon dilution with water. As a result, they have found that a pesticidal emulsifiable concentrate containing an aromatic hydrocarbon as a solvent, and a polyoxyethylene polyoxypropylene polyarylphenol and an alkylarylsulfonate as surfactants can attain the desired object. Thus, the present invention has been completed. That is, the pesticidal emulsifiable concentrate of the present invention comprises pyridalyl, a polyoxyethylene polyoxypropylene polyarylphenol, an alkylarylsulfonate and an aromatic hydrocarbon. The proportion of the respective ingredients in the pesticidal emulsifiable concentrate of the present invention is usually 5 to 60% by weight of pyridalyl, 2 to 15% by weight of the polyoxyethylene polyoxypropylene polyarylphenol, 2 to 15% by weight of the alkylarylsulfonate and 10 to 90% by weight of the aromatic hydrocarbon. The pesticidal emulsifiable concentrate of the present invention may essentially consist of pyridalyl, a polyoxyethylene polyoxypropylene polyarylphenol, an alkylarylsulfonate and an aromatic hydrocarbon. Alternatively, it may further contain other auxiliaries such as other solvents, antioxidants, preservatives, coloring agents, and the like. Examples of the other solvent include esters such as methyl oleate and dibutyl adipate; aliphatic hydrocarbons such as octane and decane; ketones such as cyclohexanone; and amides such as N, N-dimethylformamide and N- methylpyrrolidone. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Pyridalyl to be used in the present invention can be produced, for example, by the process disclosed in W096/11909. As described above, usually, the pesticidal emulsifiable concentrate can contain 5 to 60% by weight of pyridalyl. In the present invention, the polyoxyethylene polyoxypropylene polyarylphenol is a nonionic surfactant wherein ethylene oxides and propylene oxides are addition- polymerized to the hydroxy moieties of a polymerized phenol compound having two or more aromatic rings, and is also called as a polyoxyethylene polyoxypropylene polyarylphenyl ether. Examples thereof include polyoxyethylene polyoxypropylene polystyrylphenol (or polyoxyethylene polyoxypropylene polystyrylphenyl ether) such as polyoxyethylene polyoxypropylene distyrylphenol and polyoxyethylene polyoxypropylene tristyrylphenol. In the present invention, polyoxyethylene polyoxypropylene tristyrylphenol is preferably used. In the present invention, a commercially available polyoxyethylene polyoxypropylene polyarylphenol as such can be used, and examples the polyoxyethylene polyoxypropylene polyarylphenol include Soprophor 796/P (trade name of polyoxyethylene polyoxypropylene tristyrylphenol manufactured by Rhodia Nicca Co., Ltd.), and Soprophor TSP/461 (trade name of polyoxyethylene polyoxypropylene tristyrylphenol manufactured by Rhodia Nicca Co., Ltd.). Usually, the pesticidal emulsifiable concentrate of the present invention contains 2 to 15% by weight of the polyoxyethylene polyoxypropylene polyarylphenol. The alkyl group of the alkylarylsulfonate to be used in the present invention usually has 8 to 15 carbon atoms. Further, examples of the salt of the alkylarylsulfonate include alkali metal salts such as sodium salt, potassium salt, etc.; and alkaline earth metal salts such as calcium salt, magnesium salt, etc.; amine salts such as aklylamine salts, alkanol amine salts, cyclohexylamine salt, etc.; and ammonium salt. Examples of the alkylarylsulfonate to be used in the present invention include alkylbenzenesulfonate. As specific examples thereof, there are sodium dodecylbenzenesulfonate and calcium dodecylbenzenesulfonate. The pesticidal emulsifiable concentrate of the present invention usually contains 2 to 15% by weight of the alkylarylsulfonate. Examples of the aromatic hydrocarbon to be used in the present invention include liquid aromatic hydrocarbon solvents such as alkylbenzenes (e.g., toluene, etc.), dialylbenzenes (e.g., xylene, etc.), trialkylbenzenes (e.g., trimethylbenzene, etc.), alkylnaphthalenes (e.g., methylnaphthalene, etc.), dialkylnaphthalenes (e.g., dimethylnephthalene, etc.), trialkylnaphthalenes (e.g., dimethyl-monopropylnaphthalene, etc.), phenylxylylethane, and the like. In the present invention, as the aromatic hydrocarbon, a commercially available solvent as such can be used. Examples commercially available solvents include Hisol SAS- 296 (trade name of a mixture of 1-phenyl-l-xylylethane and 1-phenyl-l-ethylphenylethane manufactured by Nippon Oil Corporation) , Cactus Solvent HP-MN (trade name of methylnaphthalene 80% manufactured by Nikko Petrochemical Company), Cactus Solvent HP-DMN (dimethylnaphthalene 80% manufactured by Nikko Petrochemical Company), Cactus Solvent P-100 (trade name of C9-10 alkylbenzene manufactured by Nikko Petrochemical Company), Cactus Solvent P-150 (trade name of alkylbenzene manufactured by Nikko Petrochemical Company), Cactus Solvent P-180 (trade name of a mixture of methylnaphthalene and dimethylnaphthalene manufactured by Nikko Petrochemical Company), Cactus Solvent P-200 (trade name of a mixture of methylnaphthalene and dimethylnaphthalene manufactured by Nikko Petrochemical Company), Cactus Solvent P-220 (trade name of a mixture methylnaphthalene and dimethylnaphthalene manufactured by Nikko Petrochemical Company), Cactus Solvent PAD-1 (dimethyl-monoisopropylnaphthalene manufactured by Nikko Petrochemical Company), Solvesso 100 (trade name of aromatic hydrocarbon manufactured by Exxon Chemical Company), Solvesso 150 (trade name of aromatic hydrocarbon manufactured by Exxon Chemical Company), Solvesso 200 (trade name of aromatic hydrocarbon manufactured by Exxon Chemical Company), Solvesso 150 ND (manufactured by ExxonMobil Chemical Company), Solvesso 200 ND (manufactured by ExxonMobil Chemical Company) , ULTRA LOW NAPHTHALENE AROMATIC 150 (manufactured by ExxonMobil Chemical Company), ULTRA LAW NAPHTHALENE AROMATIC 200 (manufactured by ExxonMobil Chemical Company), Swasol 100 (trade name of toluene manufactured by Maruzen Petrochemical Company, Limited) and Swasol 200 (trade name of xylene manufactured by Maruzen Petrochemical Company, Limited). The pesticidal emulsifiable concentrate of the present invention usually contains 10 to 90% by weight of the aromatic hydrocarbon. The pesticidal emulsifiable concentrate of the present invention can be produced, for example, by stirring pyridalyl, a polyoxyethylene polyoxypropylene polyarylphenol, an alkylarylsulfonate and an aromatic hydrocarbon, if necessary, with heating (80°C of lower) to obtain a uniform mixture and, if necessary, filtering the resultant mixture. The pesticidal emulsifiable concentrate of the present invention is usually applied to pests or pest inhabiting places after water dilution. That is, for example, the pesticidal emulsifiable concentrate is applied by diluting the concentrate about 10 to 5,000 times with water and spraying the diluted solution on pest inhabiting plants and/or soil. Further, the pesticidal emulsifiable concentrate of the present invention can be applied by aerial spraying such as by a helicopter, etc. The application amount of the pesticidal emulsifiable concentrate of the present invention is usually 0.1 to 100 g/10 a in terms of pyridalyl. The present invention will hereinafter be further illustrated by the following production examples, comparative production examples and test example; however, the present invention is not limited to these examples. Production Example 1 Ten parts by weight of pyridalyl, 14.0 parts by weight of polyoxyethylene polyoxypropylene tristyrylphenol (Soprophor 796/P manufactured by Rhodia Nicca Co., Ltd.), 6.0 parts by weight of calcium dodecylbenzenesulfonate, 35.0 parts by weight of xylene and 35.0 parts by weight of N,N-dimethylformamide were mixed at room temperature to obtain the pesticidal emulsifiable concentrate of the present invention (hereinafter referred to as the present invention emulsifiable concentrate 1). Production Example 2 Ten parts by weight of pyridalyl, 14.0 parts by weight of polyoxyethylene polyoxypropylene tristyrylphenol (Soprophor TSP/724 manufactured by Rhodia Nicca Co., Ltd.), 6.0 parts by weight of calcium dodecylbenzenesulfonate, 35.0 parts by weight of xylene and 35.0 parts by weight of N, N-dimethylformamide were mixed at room temperature to obtain the pesticidal emulsifiable concentrate of the present invention (hereinafter referred to as the present invention emulsifiable concentrate 2). Production Example 3 Fifty parts by weight of pyridalyl, 9.3 parts by weight of polyoxyethylene polyoxypropylene tristyrylphenol (Soprophor 796/P manufactured by Rhodia Nicca Co., Ltd.), 4.0 parts by weight of calcium dodecylbenzenesulfonate, 18.35 parts by weight of xylene and 18.35 parts by weight of N,N-dimethylformamide were mixed at room temperature to obtain the pesticidal emulsifiable concentrate of the present invention. Production Example 4 Fifty parts by weight of pyridalyl, 9.3 parts by weight of polyoxyethylene polyoxypropylene tristyrylphenol (Soprophor TSP/724 manufactured by Rhodia Nicca Co., Ltd.), 4.0 parts by weight of calcium dodecylbenzenesulfonate, 18.35 parts by weight of xylene and 18.35 parts by weight of N,N-dimethylformamide were mixed at room temperature to obtain the pesticidal emulsifiable concentrate of the present invention. Production Example 5 Ten parts by weight of pyridalyl, 14.0 parts by weight of polyoxyethylene polyoxypropylene tristyrylphenol (Soprophor 796/P manufactured by Rhodia Nicca Co., Ltd.), 6.0 parts by weight of calcium dodecylbenzenesulfonate and 70.0 parts by weight of xylene were mixed at room temperature to obtain the pesticidal emulsifiable concentrate of the present invention. Comparative Production Example 1 Ten parts by weight of pyridalyl, 14.0 parts by weight of polyoxyethylene tristyrylphenol (Soprophor TS10 manufactured by Rhodia Nicca Co., Ltd.), 6.0 parts by weight of calcium dodecylbenzenesulfonate, 35.0 parts by weight of xylene and 35.0 parts by weight of N,N- dimethylformamide were mixed at room temperature to obtain a pesticidal emulsifiable concentrate (hereinafter referred to as the comparative emulsifiable concentrate 1). Comparative Production Example 2 Ten parts by weight of pyridalyl, 14.0 parts by weight i of polyoxyethylene polyoxypropylene tristyrylphenol (Soprophor BSU manufactured by Rhodia Nicca Co., Ltd.), 6.0 parts by weight of calcium dodecylbenzenesulfonate, 35.0 parts by weight of xylene and 35.0 parts by weight of N,N- dimethylformamide were mixed at room temperature to obtain i a pesticidal emulsifiable concentrate (hereinafter referred to as the comparative emulsifiable concentrate 2). The following Test Example illustrates emulsion stability of the pesticidal emulsifiable concentrate of the present invention. Test Example In water, 3.04 g of potassium chloride and 1.39 g of magnesium chloride 6 hydrate were dissolved, and the solution was made up to 100 ml with water to prepare a hard water stock. One ml of the hard water stock was diluted and made up to 1, 000 ml with water to prepare a test hard water having the water hardness of 34.2 ppm. Likewise, 14.6 ml of the hard water stock was diluted and made up to 1,000 ml with water to prepare a test hard water having the water hardness of 500 ppm. Ninety five ml of the above test hard water having the water hardness of 34.2 ppm was placed in a 100 ml-measuring cylinder with a stopper and the measuring cylinder was allowed to stand in a constant temperature water bath at 20°C for a while to adjust the water temperature to 20°C. Then, 5 ml of the present invention emulsifiable concentrate obtained in the above Production Example was added to the measuring cylinder, and the measuring cylinder was repeatedly turned upside down 30 times at a rate of once per 2 seconds. After that, the measuring cylinder was allowed to stand again in a constant temperature water bath at 20°C for 1 hour. When the state of the emulsion in the measuring cylinder was observed after standing, both of the present invention emulsifiable concentrates 1 and 2 maintained uniform emulsion states. When the same test was conducted by using the pesticidal emulsifiable concentrate obtained in the above Comparative Production Example, a small amount of creamy separation was observed in case of using the comparative emulsifiable concentrate 1, and a trace amount of creamy separation was observed in case of using the comparative emulsifiable concentrate 2. When the same test was conducted by using the above test hard water having the water hardness of 50 0 ppm to observe the state of the emulsion, both of the present invention emulsifiable concentrates 1 and 2 maintained uniform emulsion states. However, 0.5 cc of creamy separation was observed in case of using the comparative emulsifiable concentrate 1, and a small amount of creamy separation was observed in case of using the comparative emulsifiable concentrate 2. As described hereinabove, the pesticidal emulsifiable concentrate of the present invention is excellent in emulsion stability upon water dilution, and is useful as a pesticide. WHAT IS CLAIMED IS: 1. A pesticidal emulsifiable concentrate which comprises pyridalyl, a polyoxyethylene polyoxypropylene polyarylphenol, an alkylarylsulfonate and an aromatic hydrocarbon. 2. The pesticidal emulsifiable concentrate according to claim 1, which comprises 5 to 60% by weight of pyridalyl, 2 to 15% by weight of the polyoxyethylene polyoxypropylene polyarylphenol, 2 to 15% by weight of the alkylarylsulfonate and 10 to 90% by weight of the aromatic hydrocarbon. 3. The pesticidal emulsifiable concentrate according to claim 1 or 2, wherein the polyoxyethylene polyoxypropylene polyarylphenol is polyoxyethylene polyoxypropylene tristyrylphenol. 4. The pesticidal emulsifiable concentrate according to claim 3, wherein the alkylarylsulfonate is a dodecylbenzenesulfonate. 5. The pesticidal emulsifiable concentrate according to claim 3, wherein the alkylarylsulfonate is calcium dodecylbenzenesulfonate.

Documents:

1508-CHE-2005 AMENDED CLAIMS 19-08-2013.pdf

1508-CHE-2005 CORRESPONDENCE OTHERS 19-08-2013.pdf

1508-CHE-2005 AMENDED CLAIMS 29-07-2013.pdf

1508-CHE-2005 AMENDED PAGES OF SPECIFICATION 29-07-2013.pdf

1508-CHE-2005 CORRESPONDENCE OTHERS 31-08-2012.pdf

1508-CHE-2005 EXAMINATION REPORT REPLY RECEIVED 29-07-2013.pdf

1508-CHE-2005 POWER OF ATTORNEY 29-07-2013.pdf

1508-CHE-2005 CORRESPONDENCE OTHERS 05-02-2013.pdf

1508-CHE-2005 CORRESPONDENCE OTHERS 12-08-2013.pdf

1508-CHE-2005 FORM-3 05-02-2013.pdf

1508-CHE-2005 OTHER PATENT DOCUMENT 05-02-2013.pdf